Boron-nitrogen compound, OLED (Organic Light Emitting Diode) with compound and organic light emitting device

Abstract

The invention relates to the technical field of preparation of organic photoelectric materials, in particular to a boron-nitrogen compound, an OLED with the compound and an organic light-emitting device with the compound. According to the boron-nitrogen compound disclosed by the invention, through matching of a fused heterocyclic structure and limited groups such as tert-butyl and silyl, the thermal stability of the compound can be improved, and the boron-nitrogen compound has an excellent luminescence characteristic; the boron-nitrogen compound provided by the invention is used as a light-emitting layer material, so that the organic light-emitting device can effectively have lower driving voltage and maintain the stability of the voltage, and the light-emitting efficiency is improved.

Description

Technical Field

[0001] The present invention relates to the technical field of the preparation of organic optoelectronic materials, and particularly relates to a boron nitride compound, an OLED having the compound, and an organic light-emitting device. Background Art

[0002] An organic light-emitting diode (OLED), also known as an organic light-emitting device, is a technology that applies a voltage to an organic light-emitting element, injects holes from the anode and electrons from the cathode into the light-emitting layer respectively, and the injected holes and electrons recombine to form excitons, resulting in light emission. It can convert electrical energy into light energy through organic light-emitting materials.

[0003] Most of the light-emitting layers in OLED devices use a host-guest light-emitting system, that is, a guest material is doped in a host material. Currently, green doping materials mostly focus on boron-nitrogen hetero-fused ring molecules, but the types and quantities of existing materials are still small, resulting in difficulties in the study of the structure-activity relationship; and in their applications, display technologies still have problems such as high driving voltage and short display life, seriously affecting the further practical application of this technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low-voltage driving, 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] In order to solve the above technical problems, the present invention provides a boron nitride compound, an OLED having the compound, and a display or lighting device. The boron nitride compound can improve the luminous efficiency and thermal stability through the combination of phenyl-fused heterocycles and defined groups, and the molecular structure is easy to modify. The boron nitride compound provided by the present invention, as a light-emitting layer material, can effectively make the organic light-emitting device have a lower driving voltage and maintain voltage stability, and improve the luminous efficiency.

[0006] The boron nitride compound provided by the present invention is achieved through the following technical solutions:

[0007] A boron nitride compound, the compound has the structure shown in the following formula (I):

[0008]

[0009] In formula I, Y is selected from a substituted or unsubstituted C6-C30 aryl group. When containing substituents, the substituents are selected from one or more combinations of hydrogen, deuterium, and fused tetramethylcyclohexane;

[0010] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C36 heteroaryl, substituted or unsubstituted C1-C24 silyl; when containing substituents, the substituents can be mono-substituted or multi-substituted, and the substituents are each independently selected from one or more combinations of deuterium, C1-C20 alkyl, trimethylsilyl, methyl-substituted or unsubstituted tetrahydronaphthyl, C6-C30 aryl, and C5-C36 heteroaryl; and Ar1 and Ar2 are not phenyl at the same time;

[0011] X1 and X2 are each independently selected from a single bond, O, S, Se atom or CR a R b 、SiR c R d 、NR e ,R a -R e are each independently selected from C1-C4 alkyl, C6-C12 aryl;

[0012] R1-R4 represent unsubstituted, mono-substituted or multi-substituted, and R1-R4 are each independently selected from one or more combinations of hydrogen, deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, and C1-C24 silyl.

[0013] In the compound shown by Formula I of the present invention, the hydrogen atom can be substituted by deuterium, tritium, cyano, or halogen atom.

[0014] Preferably, the structure of Formula I can be selected from any one of the following Formula I-1 to Formula I-6:

[0015]

[0016] Among them, the definitions of Ar1, Ar2, X1, X2, and R1-R4 are the same as those defined above.

[0017] More preferably, X1 and X2 are each independently selected from a single bond, O, S, Se atom or CR a R b 、SiR c R d 、NR e ;R a -R d are each independently selected from methyl or phenyl, and R e is selected from phenyl.

[0018] Preferably, the R1-R4 are each independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, trimethylsilyl, methyldiphenylsilyl, dimethylphenylsilyl, triphenylsilyl, and adamantyl.

[0019] Preferably, each of Ar1 and Ar2 is independently selected from a substituted or unsubstituted C6-C36 aryl group, trimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenyldisilyl group, dibenzofuranyl group, substituted or unsubstituted carbazolyl group, and substituted or unsubstituted N-phenylcarbazolyl group; when having a substituent, the substituent may be mono-substituted or multi-substituted, and the substituents are independently selected from one or more combinations of deuterium, methyl group, ethyl group, propyl group, tert-butyl group, tetramethylcyclohexyl group, and trimethylsilyl group.

[0020] Preferably, each of Ar1 and Ar2 is independently selected from any one of the following, where "*" represents the connection site, "tBu" represents tert-butyl group, and "Ph" represents phenyl group:

[0021]

[0022] Among them, the hydrogen atoms in the above groups can be replaced by deuterium atoms.

[0023] According to one or more embodiments, the present invention provides a boron nitride compound, and the compound is selected from any one of the following chemical structures, where "tBu" represents tert-butyl group, "Ph" represents phenyl group, and "Ad" represents adamantyl group:

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] The present invention also provides an application of the boron nitride compound as described above in an organic electroluminescent device.

[0046] The present invention also provides an organic electroluminescent device, which comprises:

[0047] A substrate layer;

[0048] A first electrode, which is above the substrate layer;

[0049] An organic light-emitting functional layer, which is above the first electrode;

[0050] A second electrode, which is above the organic light-emitting functional layer;

[0051] The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer contains the boron nitride compound as described above.

[0052] The present invention also provides a composition, which contains the boron nitride compound as described by formula (I).

[0053] The present invention also provides a preparation, which contains the boron nitride compound with the structure shown by the above formula (I) or the composition as described above and at least one solvent. There is no particular limitation on the solvent, and unsaturated hydrocarbon solvents well known to those skilled in the art such as toluene, xylene, mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., and ester solvents such as alkyl benzoate can be used.

[0054] 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, the microdisplay field, and automotive center control screens or automotive tail lights.

[0055] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices as described above.

[0056] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0057] The boron nitride compound of the present invention, through the combination of a fused heterocyclic structure and defined groups such as tert-butyl and silyl groups, endows the structure of the boron nitride compound with good thermal stability and film-forming properties, exhibits good hole and electron transport capabilities, and can effectively improve the energy transfer performance between the host and the guest; after the boron nitride compound provided by the present invention is prepared into an organic light-emitting device, it can effectively make the organic light-emitting device have a lower driving voltage and maintain voltage stability, and the luminous efficiency is improved, and the working life of the device can also be better. Detailed Embodiments

[0058] The technical solutions of the embodiments of the present invention will be described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative efforts belong to the protection scope of the present invention.

[0059] The term "alkyl" means and includes straight-chain and branched-chain alkyls. Preferred alkyls are alkyls containing 1-20 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, etc. Additionally, the alkyl can be optionally substituted.

[0060] The term "cycloalkyl" means and includes monocyclic, polycyclic and spiroalkyls. Preferred cycloalkyls are cycloalkyls containing 3 to 20 ring carbon atoms, more preferred cycloalkyls are cycloalkyls containing 3 to 12 ring carbon atoms, particularly preferred are cycloalkyls 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, etc. Additionally, the cycloalkyl can be optionally substituted.

[0061] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycycle can have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is an aromatic hydrocarbon group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing six to thirty carbon atoms, more preferably six to twelve carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, chrysene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group can be optionally substituted. In this specification, the substituted aryl group can also include the form in which an aliphatic ring is fused to the aryl group. For example, the substituted aryl group includes tetrahydronaphthyl or indanyl.

[0062] The heteroaryl group refers to the general term of groups obtained by replacing one or more aryl nuclear carbons in the aryl group with heteroatoms, and the heteroatoms include, but are not limited to, oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group can be a monocyclic heteroaryl group or a fused-ring heteroaryl group, and can be a heteroaryl group having 5 to 36 carbon atoms, preferably 6 to 20 carbon atoms. Examples can include pyridyl, pyrrolyl, pyridinyl, thienyl, furyl, indolyl, quinolinyl, isoquinolinyl, benzothienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0063] Throughout the specification, unless explicitly described to the contrary, "including" any component will be understood to implicitly include other elements, rather than exclude any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it can be "directly on" the other element, or there can also be intermediate elements. Additionally, "on" or "above" means located above the target part, and does not necessarily mean located above in the direction of gravity.

[0064] An object of the present invention is to provide an electroluminescent device, and the organic electroluminescent device includes: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; a second electrode on the organic light-emitting functional layer; the organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer includes a boron nitride compound having a fused heterocyclic fragment.

[0065] In one embodiment of the present invention, the light-emitting layer in the organic electroluminescent (OLED) device contains one or more of the compounds shown in the above general formula (Ⅰ) as light-emitting doping materials.

[0066] In a preferred embodiment of the present invention, an OLED is provided, which includes 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-transporting layer, a hole-injecting layer, an electron-transporting layer, an electron-injecting layer, etc., or may only include a light-emitting layer and one or more other layers. Among them, the light-emitting layer contains a light-emitting doping material composed of one or more of the compounds represented by the above general formula (I). Optionally, there are a cover layer, a protective layer, and / or an encapsulation layer above the organic light-emitting functional layer.

[0067] The substrate described in the present invention can be any substrate used in typical organic light-emitting devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, and waterproof properties, and are used in different directions according to the properties of the substrates.

[0068] In a preferred embodiment of the present invention, the OLED device includes a hole-injecting layer, and the P-type doping material in the hole-injecting layer can be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0069]

[0070] In a preferred embodiment of the present invention, the OLED device includes a hole-transporting layer, and the hole-transporting layer can be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0071]

[0072]

[0073] In a preferred embodiment of the present invention, the OLED device includes an electron-transporting layer, and the electron-transporting layer can be selected from known or unknown materials, particularly preferably from the following structures, but this does not mean that the present invention is limited to the following structures:

[0074]

[0075] As a host material capable of generating green phosphorescent self-luminescence, or as a sensitizer capable of generating green phosphorescence and finally a host material emitting green fluorescence, it needs to have appropriate energy levels and can effectively cooperate with the guest material to excite energy for luminescence.

[0076] The present invention will be specifically described below in conjunction with specific embodiments. In the synthesis examples, all raw materials and solvents were commercially available and used directly without further treatment if not otherwise specified.

[0077] Example

[0078] Example 1: Synthesis of Compound 021

[0079] Synthesis route:

[0080]

[0081] 1) Dissolve Compound SM1 (1 mmol) and CsCO3 (2 mmol) in 50 ml of anhydrous DMF, stir for 20 min, add Compound SM2 (1 mmol) under a nitrogen atmosphere, heat to 120 °C and heat for 15 hours, then cool to room temperature to obtain a reaction solution. Remove the solvent in the above reaction solution by rotary evaporation to obtain a residue. Dissolve it in 50 ml of dichloromethane and then extract with 50 ml of distilled water to obtain an organic phase. The residue is extracted with dichloromethane (3 × 100 mL) to obtain an organic phase. The four organic phases are combined and dried over anhydrous sodium sulfate. The dried organic phase is distilled under reduced pressure to remove the solvent therein to obtain a solid. The obtained solid is separated and purified by a silica gel chromatography column, and the eluent is dichloromethane: petroleum ether = 1:4 (volume ratio) to obtain intermediate product S1.

[0082] 2) Dissolve intermediate product S1 (1 mmol) in 50 mL of THF. Under a nitrogen atmosphere at -78 °C, add a solution of n-butyllithium (2 mmol, 2.7 M), stir to dissolve, and then slowly add a THF solution of Compound SM3 (1 mmol) to obtain a reaction solution. Stir the reaction solution at room temperature for 12 hours. After the reaction is completed, add 0.5 mol / L HCl solution, H2O, and EA for extraction to obtain an organic phase. Then extract the remaining aqueous phase with EA 3 times to obtain an organic phase. The organic phases are combined, washed with anhydrous DMF, dried over sodium sulfate, and rotary evaporated and passed through a column to obtain intermediate product S2.

[0083] 3) Add Compound SM4 (1 mmol), K2CO3 (5 mmol), tricyclohexylphosphine (0.15 mmol), and palladium acetate (0.05 mmol) to 100 mL of anhydrous DMF under nitrogen protection. Stir and dissolve at room temperature, then add Compound SM5 (1 mmol), heat to 120 °C and heat for 15 hours, then cool to room temperature. The organic phase is washed with water and dried over sodium sulfate, rotary evaporated and passed through a column to obtain intermediate product S3.

[0084] 4) The intermediate product S3 (1 mmoL) and the intermediate product S2 (1 mmoL) were dissolved in 50 mL of toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added to obtain a reaction system. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent in the above reaction solution was removed by rotary evaporation to obtain a residue, which was dissolved in 50 ml of dichloromethane and then extracted with 50 ml of distilled water to obtain an organic phase. The residue was extracted with dichloromethane (3×100 mL) to obtain an organic phase, and the four organic phases were combined and dried with anhydrous sodium sulfate. The dried organic phase was subjected to reduced pressure distillation to remove the solvent therein to obtain a solid, and the obtained solid was separated and purified by a silica gel chromatography column, and the eluent was dichloromethane: petroleum ether = 1:4 to obtain an intermediate product S4.

[0085] 5) The intermediate product S4 (1mmoL) was dissolved in 60mL of anhydrous tert-butylbenzene to obtain a reaction system. The reaction system was cooled to -78°C, t-BuLi (1mL, 2mmoL, 2M in hexane) was slowly added to the reaction system, and after reacting at 25°C for 4 hours, BBr3 (247mg, about 1mmoL) was slowly added to the reaction system at -40°C, warmed to room temperature, and then N,N-diisopropylethylamine (387mg, 3mmoL) was added to the reaction system, followed by heating to 80°C for 12 hours, then cooled to room temperature, and 5mL of sodium acetate aqueous solution (1M) was added to quench the reaction. The solvent in the above reaction solution was removed by rotary evaporation to obtain a residue, which was dissolved in 50ml of dichloromethane and then extracted with 50ml of distilled water to obtain an organic phase. The residue was extracted with dichloromethane (3×100mL) to obtain an organic phase, and the four organic phases were combined and dried over anhydrous sodium sulfate. The dried organic phase was distilled under reduced pressure to remove the solvent therein to obtain a solid, which was separated and purified using a silica gel chromatography column with an eluent of dichloromethane:petroleum ether=1:8 to obtain the target product 021.

[0086] The target product 021 was tested and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1112.62 and the tested value was 1113.24.

[0087] Example 2: Synthesis of Compound 024

[0088] Compound 024 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 1002.60 and the test value was 1003.20.

[0089] Example 3: Synthesis of Compound 055

[0090] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 055 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 962.52, and the measured value was 963.18.

[0091] Example 4: Synthesis of Compound 084

[0092] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 084 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 1090.63, and the measured value was 1091.27.

[0093] Example 5: Synthesis of Compound 100

[0094] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 100 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 1090.63, and the measured value was 1091.25.

[0095] Example 6: Synthesis of Compound 102

[0096] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 102 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 1000.49, and the measured value was 1001.11.

[0097] Example 7: Synthesis of Compound 108

[0098] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 108 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 986.48, and the measured value was 987.12.

[0099] Example 8: Synthesis of Compound 119

[0100] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 119 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 1104.65, and the measured value was 1105.23.

[0101] Example 9: Synthesis of Compound 132

[0102] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 132 was synthesized. By liquid chromatography-mass spectrometry analysis, the LC-MS (m / z) was obtained: the theoretical value was 1018.43, and the measured value was 1019.11.

[0103] Example 10: Synthesis of Compound 141

[0104] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 141 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 950.52, measured value 951.08.

[0105] Example 11: Synthesis of Compound 159

[0106] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 159 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1248.69, measured value 1249.31.

[0107] Example 12: Synthesis of Compound 172

[0108] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 172 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1138.69, measured value 1139.31.

[0109] Example 13: Synthesis of Compound 179

[0110] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 179 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1104.65, measured value 1105.33.

[0111] Example 14: Synthesis of Compound 199

[0112] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 199 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1352.81, measured value 1353.67.

[0113] Example 15: Synthesis of Compound 209

[0114] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 209 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1242.88, measured value 1243.68.

[0115] Example 16: Synthesis of Compound 213

[0116] Referring to the synthesis steps and reaction conditions of Reference Example 1, Compound 213 was synthesized. LC-MS (m / z) obtained by liquid chromatography-mass spectrometry analysis was: theoretical value 1158.70, measured value 1159.46.

[0117] Example 17: Synthesis of Compound 215

[0118] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 215 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1108.68 and a measured value of 1109.22.

[0119] Example 18: Synthesis of Compound 219

[0120] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 219 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1340.85 and a measured value of 1341.83.

[0121] Example 19: Synthesis of Compound 222

[0122] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 222 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1154.63 and a measured value of 1155.33.

[0123] Example 20: Synthesis of Compound 226

[0124] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 226 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1043.53 and a measured value of 1044.13.

[0125] Example 21: Synthesis of Compound 231

[0126] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 231 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1099.60 and a measured value of 1100.28.

[0127] Example 22: Synthesis of Compound 248

[0128] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 248 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1218.66 and a measured value of 1219.38.

[0129] Example 23: Synthesis of Compound 252

[0130] Referring to the synthesis steps and reaction conditions of Reference Example 1, compound 252 was synthesized. LC-MS (m / z) analysis by liquid chromatography-mass spectrometry showed a theoretical value of 1119.57 and a measured value of 1120.23.

[0131] The following are several application examples of the boron nitride compound described in the present invention in OLED devices to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples were purchased commercially or synthesized by ourselves.

[0132] Fabrication of OLED device:

[0133] As a reference preparation method for a device example, in the present invention, ITO / Ag / ITO with a thickness of 50 - 500 nm is evaporated on an alkali-free glass substrate as the anode, and a hole injection layer (5 nm - 20 nm), a hole transport layer (50 - 120 nm), a light-emitting auxiliary layer (5 - 120 nm), a light-emitting layer (20 - 50 nm), a hole blocking layer (5 - 20 nm), an electron transport layer (20 - 80 nm), and an electron injection layer (1 - 10 nm) are evaporated on the anode. Then, Mg and Ag (weight ratio 1:9, 10 - 15 nm) are co-evaporated to form a semi-transparent cathode, and then a capping layer compound is evaporated. Finally, the light-emitting device is encapsulated with an epoxy resin adhesive under a nitrogen atmosphere.

[0134] In a preferred specific embodiment, the structure of the OLED device provided by the present invention is as follows: First, an alkali-free glass substrate is washed with isopropyl alcohol for 15 minutes using an ultrasonic cleaner, and then subjected to a 30-minute UV ozone washing treatment in air. The treated substrate is evaporated with ITO / Ag / ITO 100 nm as the anode using a vacuum evaporation method. Then, a hole injection layer (HT:PD, 10 nm, 2%), a hole transport layer (HT, 130 nm), a light-emitting auxiliary layer (GP, 50 nm), a green light-emitting layer (host material; dopant = compound GH1:GH2:compound GD:compound 001 (weight ratio 66:30:3:1, 30 nm)), a hole blocking layer (compound HBL, 5 nm), an electron transport layer (compound ET:Liq = 1:1, 30 nm), and an electron injection layer (Yb, 1 nm) are sequentially evaporated and laminated. Then, Mg and Ag (weight ratio 1:9, 13 nm) are co-evaporated to form a semi-transparent cathode, and then compound CPL (65 nm) is evaporated as a capping layer. Finally, the light-emitting device is encapsulated with an epoxy resin adhesive under a nitrogen atmosphere, denoted as Application Example 1. The molecular structural formulas of the related materials are as follows (specifically preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures):

[0135]

[0136]

[0137] Referring to the method provided in Application Example 1 above, Application Examples 2 - 23 and Comparative Example 1 are prepared, with the only difference being that the compounds listed in Table 1 are respectively used as dopants to replace compound 021 in Application Example 1. The dopant in Comparative Example 1 is as follows:

[0138]

[0139] Performance evaluation of OLED devices:

[0140] Use a Keithley 2365Α digital nanovoltmeter to measure the current of the OLED device at different voltages, and then divide the current by the luminous area to obtain the current density of the OLED device at different voltages; use a Konica Minolta CS-2000 spectro-radiance meter to measure the luminance and radiant energy flux density of the OLED device at different voltages; according to the current density and luminance of the OLED device at different voltages, obtain the operating voltage Volt and current efficiency at the same current density (10 mA / cm 2 ). The test data is shown in Table 1. The following data are all based on the test data of the compound in Comparative Example 1. The data of Comparative Example 1 are: voltage 3.72 (V); luminous efficiency 211.5 (cd / A); lifetime 441 (LT95@10J, hrs).

[0141] Table 1 Organic electroluminescent device and electroluminescent characteristics table

[0142]

[0143]

[0144] It can be seen from Table 1 that compared with Comparative Examples 1-2, Application Examples 1 to 23 have comparable operating voltages, higher BI luminous efficiency, and longer service life. The performance improvement of each application example is based on the combination of fused heterocyclic structures and defined groups such as tert-butyl and silyl groups in the present invention, which makes the boron nitride compound material have better luminous efficiency. Moreover, the compatibility of the doping materials in the present invention is good, which can better achieve the balance of electron and hole transport and exciton conversion rate in the light-emitting layer, reduce the power consumption of the device, and extend the service life.

[0145] This specific embodiment is only an explanation of the present invention, and it is not a limitation of the present invention. Those skilled in the art can make modifications to this embodiment without creative contributions according to needs after reading this specification, but as long as they are within the scope of the claims of the present invention, they are protected by the patent law.

Claims

1. A boron nitride compound, characterized in that, The compound has the structure shown in Formula I as follows: In Formula I, Y is selected from a substituted or unsubstituted C6-C30 aryl group. When it contains substituents, the substituents are selected from one or more combinations of hydrogen, deuterium, and fused tetramethylcyclohexane; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, and a substituted or unsubstituted C1-C24 silyl group; when containing substituents, the substituents can be mono-substituted or multi-substituted, and the substituents are each independently selected from one or more combinations of deuterium, a C1-C20 alkyl group, a trimethylsilyl group, a methyl-substituted or unsubstituted tetrahydronaphthyl group, a C6-C30 aryl group, and a C5-C36 heteroaryl group; and Ar1 and Ar2 are not both phenyl at the same time; X1 and X2 are each independently selected from a single bond, an O, S, Se atom or CR a R b , SiR c R d , NR e , R a -R e are each independently selected from C1-C4 alkyl, C6-C12 aryl; R1-R4 represent unsubstituted, mono-substituted or multi-substituted, and R1-R4 are each independently selected from one or more combinations of hydrogen, deuterium, a C1-C24 alkyl group, a C3-C24 cycloalkyl group, and a C1-C24 silyl group.

2. The boron nitride compound according to claim 1, characterized in that, The structure of Formula I can be selected from any one of the following structures of Formula I-1 to Formula I-6: Wherein, the definitions of Ar1, Ar2, X1, X2, and R1-R4 are the same as those described in Claim 1.

3. The boron nitride compound according to claim 1, characterized in that, X1 and X2 are each independently selected from a single bond, an O, S, Se atom, or CR a R b , SiR c R d , NR e ; R a -R d are each independently selected from methyl or phenyl, and R e is selected from phenyl.

4. The boron nitride compound according to claim 1, wherein The R1-R4 are each independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, trimethylsilyl, methyldiphenylsilyl, dimethylphenylsilyl, triphenylsilyl, and adamantyl.

5. The boron nitride compound according to claim 1, characterized in that, The Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group, trimethylsilyl, triphenylsilyl, diphenylsilyl, phenyldisilyl, dibenzofuranyl, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group; when containing substituents, the substituents can be mono-substituted or multi-substituted, and the substituents are each independently selected from one or more combinations of deuterium, methyl, ethyl, propyl, tert-butyl, tetramethylcyclohexyl, and trimethylsilyl.

6. The boron nitride compound according to claim 1, wherein The Ar1 and Ar2 are each independently selected from any one of the following, where "*" represents the connection site, "tBu" represents tert-butyl, and "Ph" represents phenyl: Wherein, the hydrogen atoms in the above groups can be replaced by deuterium atoms.

7. The boron nitride compound according to claim 1, characterized in that, The compound is selected from any one of the following chemical structures shown, where "tBu" represents tert-butyl, "Ph" represents phenyl, and "Ad" represents adamantyl:

8. Use of the boron nitride compound according to any one of Claims 1-7 in the preparation of an organic electroluminescent device.

9. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: A substrate layer; A first electrode, which is on the substrate layer; An organic light-emitting functional layer, which is on the first electrode; A second electrode, which is on the organic light-emitting functional layer; The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes the boron nitride compound according to any one of Claims 1-7.

10. A composition, characterized in that, The composition contains the boron nitride compound according to any one of Claims 1-7.

11. A preparation, characterized in that, The preparation contains a boron nitride compound as described in any one of claims 1-7 or a composition as described in claim 10 and at least one solvent.

12. Application of the organic electroluminescent device according to claim 9 in a display or lighting device.

13. A display or lighting device, characterized in that, The device contains an organic electroluminescent device as described in claim 9.

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