Boron-nitrogen compound containing carbazole group, and OLED and organic light-emitting device comprising same

Abstract

The present invention relates to the technical field of the preparation of organic photoelectric materials, and in particular relates to a boron-nitrogen compound containing a carbazole group, and an OLED and an organic light-emitting device comprising same. According to the boron-nitrogen compound containing a carbazole group, by defining a combination of an aromatic group and a carbazole structure with a mother nucleus, the compound has an excellent light-emitting efficiency and a better thermal stability. Moreover, using the boron-nitrogen compound containing a carbazole group as a light-emitting layer material in an apparatus can effectively enable the organic light-emitting apparatus to have a lower driving voltage and maintain voltage stability. In addition, the light-emitting efficiency is improved, and the operating life is significantly extended, and thus the compound has good application prospects.

Description

A boron nitrogen compound containing a carbazole group, an OLED having the compound, and an organic light-emitting device. Technical Field

[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to a boron nitrogen compound containing a carbazole group, an OLED having the compound, and an organic light-emitting device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting devices, are a technology that converts electrical energy into light energy through organic light-emitting materials. This technology involves applying voltage to an organic light-emitting element to inject holes from the anode and electrons from the cathode into the light-emitting layer. The injected holes and electrons then recombine to form excitons, causing light to be emitted.

[0003] Existing light-emitting materials still have shortcomings in improving device performance. Even when multiple materials are used in combination, display technology still suffers from problems such as high driving voltage and short display lifespan, which seriously affects the further practical application of the technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long lifespan, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides a boron-nitrogen compound containing a carbazole group, an OLED having the compound, and a display or lighting device. The provided compound contains a carbazole structure and is complexed with an aromatic group, thereby enabling the use of this carbazole-containing boron-nitrogen compound in organic electroluminescent devices, allowing the devices to simultaneously possess high efficiency and a long operating life.

[0006] The boron-nitrogen compound containing a carbazole group provided by this invention is achieved through the following technical solution:

[0007] A boron nitrogen compound containing a carbazole group, wherein the boron nitrogen compound containing the carbazole group has the structure shown in Formula I:

[0008] In Formula I, R1 and R2 are each independently selected from C1-C24 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aromatic amino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C5-C36 heteroaryl. R1 and R2 may be fused with adjacent phenyl groups. R3 and R4 are each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C5-C36 heteroaryl. When R1–R4 contain a substituted substance, the substituted substance is one or more combinations of hydrogen, deuterium, C1-C24 alkyl, C3-C20 cycloalkyl, and C6-C30 aryl. R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, C6–C30 aryl, C5-C36 heteroaryl, and C6-C30 aromatic silyl. At least one of R1–R5 contains a carbazole group.

[0009] Preferably, the hydrogen atoms of the compound of Formula I may be partially or completely deuterated.

[0010] Preferably, Formula I can be selected from any of the following structures: Formula I-1 to Formula I-5

[0011] In Formulas I-1 to I-3, the substitutions of R2-R5 are defined as described in claim 1; in Formulas I-4 to I-5, R2 is selected from tert-butyl, phenyl, or carbazolyl, and the substitutions of R3-R5 are defined as described in claim 1.

[0012] Preferably, in Formula I, R2 is independently selected from methyl, ethyl, propyl, tert-butyl, phenyl, and carbazole.

[0013] Preferably, in Formula I, R3 and R4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted fluorenyl, and N-phenylcarbazoyl; when substituted, the substituted is selected from one or more combinations of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, and adamantyl, and at least one of R3 and R4 is selected from N-phenylcarbazoyl.

[0014] Preferably, in Formula I, R5 is independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, triphenylsilyl, and carbazole; one or more hydrogens in each substitution may be deuterated.

[0015] According to one or more embodiments, the present invention provides a boron nitrogen compound containing a carbazole group, selected from any of the following chemical structures:

[0016] The present invention also provides the application of the boron nitrogen compound containing a carbazole group as described above in organic electroluminescent devices.

[0017] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising:

[0018] Substrate layer;

[0019] A first electrode is located on the substrate;

[0020] An organic light-emitting functional layer is disposed on the first electrode;

[0021] The second electrode is located on the organic light-emitting functional layer;

[0022] The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes a boron nitrogen compound containing a carbazole group as described above.

[0023] The present invention also provides a composition comprising a boron nitrogen compound containing a carbazole group as described in Formula I.

[0024] This invention also provides a formulation comprising a boron nitrogen compound containing a carbazole group as shown in 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 well-known to those skilled in the art, such as unsaturated hydrocarbon solvents like toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.; halogenated unsaturated hydrocarbon solvents like chlorobenzene, dichlorobenzene, trichlorobenzene, etc.; ether solvents like tetrahydrofuran, tetrahydropyran, etc.; and ester solvents like alkyl benzoates.

[0025] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices.

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

[0027] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0028] The boron-nitrogen compounds containing carbazole groups of the present invention are limited to carbazole groups or aryl-substituted carbazole groups combined with aromatic groups to obtain compounds, thereby giving the compounds excellent luminous efficiency and good lifespan. At the same time, the boron-nitrogen compounds containing carbazole groups provided by the present invention, when used in devices, can effectively enable organic light-emitting devices to have lower driving voltages while maintaining voltage stability, and improve luminous efficiency, and the device's working life can also be better. Detailed Implementation

[0029] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0030] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl or a fused-ring aryl. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracene, phenanthryl, or pyrene, but are not limited thereto. Aryl or aromatic group – as used herein, considers both non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fen, fluorene, pyrene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylyl, 3,4-dimethylyl, 2,5-dimethylyl, mestriylyl, and m-tetraphenyl.

[0031] The heteroaryl group referred to in this invention is a general term for groups obtained by replacing one or more aromatic nucleus carbons in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl, and can have 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms. Examples include pyridyl, pyrroleyl, pyridinyl, thiophenyl, furanyl, indolyl, quinolinyl, isoquinolinyl, benzothiophenyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, etc., but are not limited thereto.

[0032] The alkyl groups described in this invention include straight-chain and branched alkyl groups. They can be alkyl groups having 1 to 24 carbon atoms, with preferred alkyl groups containing 1 to 4 carbon atoms, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, etc. Furthermore, the alkyl groups may optionally be substituted.

[0033] The term "cycloalkyl" as used in this invention refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 20 ring carbon atoms, more preferably those containing 3 to 12 ring carbon atoms, and particularly preferably those containing 3 to 6 ring carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Furthermore, the cycloalkyl group may optionally be substituted.

[0034] Throughout this specification, unless explicitly stated otherwise, the term "including" any component will be understood to imply the inclusion of other components, not to exclude any other components. 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 "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.

[0035] One object of the present invention is to provide an electroluminescent device, the organic electroluminescent device comprising: 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 comprising a light-emitting layer comprising a boron nitrogen compound having a carbazole structural segment.

[0036] In one embodiment of the present invention, the light-emitting auxiliary layer in the organic electroluminescent (OLED) device comprises one or more components of the compound represented by the above general formula (I) as a light-emitting dopant material.

[0037] 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, wherein the organic light-emitting functional layer may include a light-emitting layer, a light-emitting auxiliary layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers; wherein the light-emitting layer comprises one or more compounds represented by the above 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.

[0038] The substrate described in this invention can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.

[0039] As for the hole injection layer, hole transport layer, and electron injection layer materials, any material can be selected from known materials used in OLED devices.

[0040] The present invention will now be described in detail with reference to specific embodiments. Unless otherwise specified, all raw materials and solvents used in the synthesis embodiments are commercially available, and the solvents were used directly without further processing.

[0041] Example

[0042] Example 1: Synthesis of Compound 001

[0043] Synthesis route:

[0044] 1) In a three-necked reaction flask, compounds 001-1 (1 mmol) and 001-2 (1 mmol) were dissolved in 50 mL of toluene solution. 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 vacuum distillation, and the crude product was purified by silica gel column chromatography with an eluent of dichloromethane:petroleum ether = 1:4. The intermediate product was 001-3.

[0045] 2) Dissolve intermediate 001-3 (1 mmol) and compound 001-4 (1 mmol) in 50 mL of toluene solution. 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 with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with an eluent of dichloromethane:petroleum ether = 1:4. Intermediate product 001-5.

[0046] 3) Dissolve intermediate 001-5 (1 mmol) and compound 001-6 (1 mmol) in 50 mL of toluene solution. 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 with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with an eluent of dichloromethane:petroleum ether = 1:4. Intermediate product 001-7.

[0047] 4) Dissolve intermediate 001-7 (1 mmol) and compound 2-009-8 (1 mmol) in 50 mL of toluene solution. 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 with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography with an eluent of dichloromethane:petroleum ether = 1:4. The intermediate product is 001-9.

[0048] 5) Dissolve intermediate 001-9 (1 mmol) in 60 mL of anhydrous tert-butylbenzene. Cool the reaction system to -78 °C and slowly add BuLi (1 mL, 2 mmol, 2 M in hexane). After reacting at -78 °C for 4 hours, slowly add BBr3 (247 mg, approximately 1 mmol). After reacting at -50 °C for 1 hour, raise the temperature to room temperature, then add N,N-diisopropylethylamine (387 mg, 3 mmol), and then heat to 120 °C for 12 hours. After cooling to room temperature, add 5 mL of sodium acetate aqueous solution (1 M). Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry with sodium sulfate. Remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography using dichloromethane: petroleum ether = 1:8 as the eluent to obtain the final product 001.

[0049] The structure of the target product 001 was tested: the theoretical value was 1052.50 and the measured value was 1053.16, obtained by liquid chromatography-mass spectrometry (LC-MS) analysis.

[0050] Example 2: Synthesis of Compound 005

[0051] Following the synthesis steps and reaction conditions of Example 1, compound 005 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1120.56 and a measured value of 1121.26 (m / z).

[0052] Example 3: Synthesis of Compound 013

[0053] Following the synthesis steps and reaction conditions of Example 1, compound 013 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1133.56 and a measured value of 1134.32 (m / z).

[0054] Example 4: Synthesis of Compound 014

[0055] Following the synthesis steps and reaction conditions of Example 1, compound 014 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1187.61 and a measured value of 1188.35 (m / z).

[0056] Example 5: Synthesis of Compound 026

[0057] Following the synthesis steps and reaction conditions of Example 1, compound 026 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1263.64 and a measured value of 1264.46 (m / z).

[0058] Example 6: Synthesis of Compound 027

[0059] Following the synthesis steps and reaction conditions of Example 1, compound 027 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1229.56 and a measured value of 1230.42 (m / z).

[0060] Example 7: Synthesis of Compound 029

[0061] Following the synthesis steps and reaction conditions of Example 1, compound 029 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1225.61 and a measured value of 1226.43 (m / z).

[0062] Example 8: Synthesis of Compound 040

[0063] Following the synthesis steps and reaction conditions of Example 1, compound 040 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1267.51 and a measured value of 1268.29 (m / z).

[0064] Example 9: Synthesis of Compound 042

[0065] Following the synthesis steps and reaction conditions of Example 1, compound 042 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1181.53 and a measured value of 1182.31 (m / z).

[0066] Example 10: Synthesis of Compound 045

[0067] Following the synthesis steps and reaction conditions of Example 1, compound 045 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1243.54 and a measured value of 1244.38 (m / z).

[0068] Example 11: Synthesis of Compound 048

[0069] Following the synthesis steps and reaction conditions of Example 1, compound 048 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1037.56 and a measured value of 1038.18 (m / z).

[0070] Example 12: Synthesis of Compound 056

[0071] Following the synthesis steps and reaction conditions of Example 1, compound 056 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1111.58 and a measured value of 1112.22 (m / z).

[0072] Example 13: Synthesis of Compound 061

[0073] Following the synthesis steps and reaction conditions of Example 1, compound 061 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1263.64 and a measured value of 1264.28 (m / z).

[0074] Example 14: Synthesis of Compound 062

[0075] Following the synthesis steps and reaction conditions of Example 1, compound 062 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1171.58 and a measured value of 1172.36 (m / z).

[0076] Example 15: Synthesis of Compound 063

[0077] Following the synthesis steps and reaction conditions of Example 1, compound 063 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1161.51 and a measured value of 1162.35 (m / z).

[0078] Example 16: Synthesis of Compound 064

[0079] Following the synthesis steps and reaction conditions of Example 1, compound 064 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1321.72 and a measured value of 1322.58 (m / z).

[0080] Example 17: Synthesis of Compound 067

[0081] Following the synthesis steps and reaction conditions of Example 1, compound 067 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1310.59 and a measured value of 1311.23 (m / z).

[0082] Example 18: Synthesis of Compound 068

[0083] Following the synthesis steps and reaction conditions of Example 1, compound 068 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1324.60 and a measured value of 1325.34 (m / z).

[0084] Example 19: Synthesis of Compound 077

[0085] Following the synthesis steps and reaction conditions of Example 1, compound 077 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1156.59 and a measured value of 1157.41 (m / z).

[0086] Example 20: Synthesis of Compound 088

[0087] Following the synthesis steps and reaction conditions of Example 1, compound 088 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1020.54 and a measured value of 1021.20 (m / z).

[0088] Example 21: Synthesis of Compound 092

[0089] Following the synthesis steps and reaction conditions of Example 1, compound 092 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1056.52 and a measured value of 1057.20 (m / z).

[0090] Example 22: Synthesis of Compound 106

[0091] Following the synthesis steps and reaction conditions of Example 1, compound 106 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 944.51 and a measured value of 945.09 (m / z).

[0092] Example 23: Synthesis of Compound 110

[0093] Following the synthesis steps and reaction conditions of Example 1, compound 110 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 933.52 and a measured value of 934.08 (m / z).

[0094] Example 24: Synthesis of Compound 113

[0095] Following the synthesis steps and reaction conditions of Example 1, compound 113 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 919.41 and a measured value of 919.99.

[0096] Example 25: Synthesis of Compound 136

[0097] Following the synthesis steps and reaction conditions of Example 1, compound 136 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1133.56 and a measured value of 1134.22 (m / z).

[0098] Example 26: Synthesis of Compound 138

[0099] Following the synthesis steps and reaction conditions of Example 1, compound 138 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1153.53 and a measured value of 1154.29 (m / z).

[0100] Example 27: Synthesis of Compound 148

[0101] Following the synthesis steps and reaction conditions of Example 1, compound 148 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1209.60 and a measured value of 1210.32 (m / z).

[0102] Example 28: Synthesis of Compound 149

[0103] Following the synthesis steps and reaction conditions of Example 1, compound 149 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1263.64 and a measured value of 1264.30 (m / z).

[0104] Example 29: Synthesis of Compound 150

[0105] Following the synthesis steps and reaction conditions of Example 1, compound 150 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1229.56 and a measured value of 1230.38 (m / z).

[0106] Example 30: Synthesis of Compound 159

[0107] Following the synthesis steps and reaction conditions of Example 1, compound 159 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1176.50 and a measured value of 1177.22 (m / z).

[0108] Example 31: Synthesis of Compound 175

[0109] Following the synthesis steps and reaction conditions of Example 1, compound 175 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1086.58 and a measured value of 1087.24 (m / z).

[0110] Example 32: Synthesis of Compound 185

[0111] Following the synthesis steps and reaction conditions of Example 1, compound 185 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1171.58 and a measured value of 1172.30 (m / z).

[0112] Example 33: Synthesis of Compound 186

[0113] Following the synthesis steps and reaction conditions of Example 1, compound 186 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1161.51 and a measured value of 1162.27 (m / z).

[0114] Example 34: Synthesis of Compound 189

[0115] Following the synthesis steps and reaction conditions of Example 1, compound 189 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1296.72 and a measured value of 1297.50 (m / z).

[0116] Example 35: Synthesis of Compound 190

[0117] Following the synthesis steps and reaction conditions of Example 1, compound 190 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1310.59 and a measured value of 1311.57 (m / z).

[0118] Example 36: Synthesis of Compound 193

[0119] Following the synthesis steps and reaction conditions of Example 1, compound 193 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1338.62 and a measured value of 1339.40 (m / z).

[0120] Example 37: Synthesis of Compound 200

[0121] Following the synthesis steps and reaction conditions of Example 1, compound 200 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1156.59 and a measured value of 1157.41 (m / z).

[0122] Example 38: Synthesis of Compound 215

[0123] Following the synthesis steps and reaction conditions of Example 1, compound 215 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1056.52 and a measured value of 1057.12 (m / z).

[0124] Example 39: Synthesis of Compound 219

[0125] Following the synthesis steps and reaction conditions of Example 1, compound 219 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1133.56 and a measured value of 1134.32 (m / z).

[0126] Example 40: Synthesis of Compound 237

[0127] Following the synthesis steps and reaction conditions of Example 1, compound 237 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1054.49 and a measured value of 1055.17 (m / z).

[0128] Example 41: Synthesis of Compound 241

[0129] Following the synthesis steps and reaction conditions of Example 1, compound 241 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1326.56 and a measured value of 1327.40 (m / z).

[0130] Example 42: Synthesis of Compound 248

[0131] Following the synthesis steps and reaction conditions of Example 1, compound 248 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1053.50 and a measured value of 1054.14 (m / z).

[0132] Example 43: Synthesis of Compound 253

[0133] Following the synthesis steps and reaction conditions of Example 1, compound 253 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1338.50 and a measured value of 1339.42 (m / z).

[0134] Example 44: Synthesis of Compound 255

[0135] Following the synthesis steps and reaction conditions of Example 1, compound 255 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 1160.44 and a measured value of 1161.24 (m / z).

[0136] The following are several examples of applications of the boron nitrogen compounds containing carbazole groups described in this invention in OLED devices to further illustrate the beneficial effects of the compounds of this invention. The materials used in the examples were either commercially available or synthesized in-house.

[0137] Manufacturing of OLED devices:

[0138] As a reference fabrication method for one embodiment of the device, this invention involves depositing a 50-500 nm ITO / Ag / ITO layer as the anode on an alkali-free glass substrate. Then, a hole injection layer (5 nm-20 nm), a hole transport layer (50-150 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 deposited on the anode. Next, Mg and Ag (weight ratio 1:9, 10-15 nm) are co-deposited to form a semi-transparent cathode, followed by the deposition of a capping compound. Finally, the light-emitting device is encapsulated using epoxy resin adhesive under a nitrogen atmosphere.

[0139] In a preferred embodiment, the OLED device provided by the present invention has the following structure: First, an alkali-free glass substrate is washed with isopropanol for 15 minutes using an ultrasonic cleaner, followed by a 30-minute UV ozone cleaning treatment in air. The treated substrate is then vacuum-deposited with ITO / Ag / ITO 100nm as the anode. Next, a hole injection layer (HT:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a light-emitting auxiliary layer (BP, 5nm), a blue light-emitting layer (body material: dopant material = BH: compound 001 (weight ratio 98:2, 30nm)), a hole blocking layer (HBL, 5nm), an electron transport layer (ET:Liq = 1:1, 30nm), and an electron injection layer (Yb, 1nm) are sequentially deposited. Finally, Mg and Ag (weight ratio 1:9, 13nm) are co-deposited to form a semi-transparent cathode, and then compound CPL (65nm) is deposited as a capping layer. Finally, the light-emitting device was encapsulated using epoxy resin adhesive under a nitrogen atmosphere, referred to as Application Example 1. The molecular structural formulas of the relevant materials are shown below (particularly preferably selected from the following structures, but this does not mean that the invention is limited to the following structures):

[0140] Application Examples 2-44 and Comparative Example 1 were prepared using the method described in Application Example 1 above, with the only difference being that compounds listed in Table 1 were used as luminescent auxiliary materials instead of compound 001 in Application Example 1. The structure of Ref-1 used in the Comparative Example is as follows:

[0141] Performance evaluation of OLED devices:

[0142] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and then the current density of the OLED device at different voltages was obtained by dividing the current by the emitting 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 current density (10 mA / cm²) at the same voltage was obtained. 2 The operating voltage (Volt) and current efficiency (cd / A) are given by BI = E / CIEy, which refers to the Blue Index in blue light and is also a parameter measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the ordinate color point obtained by substituting the wavelength of the device's emission half-width into the CIE1930 software. The test data are shown in Table 1.

[0143] Table 1. Examples of Applications and Electroluminescence Properties of Luminescent Doped Materials

[0144] As shown in Table 1, compared with Comparative Example 1, Application Examples 1 to 44 exhibit lower operating voltages, higher BI luminous efficiency, and longer lifespan. The performance improvements in each application example are based on the fact that the material in this invention combines a nitrogen-containing heterocycle with a carbazole structure and aromatic groups, resulting in a large conjugated plane. This gives the compound good thermal stability, a higher glass transition temperature, and improves the device's lifespan. Simultaneously, the combination of the carbazole and aromatic groups significantly influences the compound's luminescent properties, thereby improving the device's luminous efficiency, better achieving a balance in electron and hole transport and exciton conversion, and reducing device power consumption.

[0145] This specific embodiment is merely an explanation of the present invention and is not intended to limit the invention. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they are within the scope of the claims of the present invention.

Claims

1. A boron-nitrogen compound containing a carbazole group, characterized in that, The boron nitrogen compound containing the carbazole group has the structure shown in Formula I: In Formula I, R1 and R2 are each independently selected from C1-C24 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aromatic amino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C5-C36 heteroaryl. R1 and R2 may be fused with adjacent phenyl groups. R3 and R4 are each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C5-C36 heteroaryl. When R1–R4 contain a substituted substance, the substituted substance is one or more combinations of hydrogen, deuterium, C1-C24 alkyl, C3-C20 cycloalkyl, and C6-C30 aryl. R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, C6–C30 aryl, C5-C36 heteroaryl, and C6-C30 aromatic silyl. At least one of R1–R5 contains a carbazole group.

2. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that, Formula I can be selected from any of the following structures from Formula I-1 to Formula I-5: In Formulas I-1 to I-3, the substitutions of R2-R5 are defined as described in claim 1; in Formulas I-4 to I-5, R2 is selected from tert-butyl, phenyl, or carbazolyl, and the substitutions of R3-R5 are defined as described in claim 1.

3. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that, In Formula I, R2 is independently selected from methyl, ethyl, propyl, tert-butyl, phenyl, and carbazole.

4. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that, In Formula I, R3 and R4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted fluorenyl, and N-phenylcarbazoyl; when substituted, the substituted is selected from one or more combinations of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, and adamantyl, and at least one of R3 and R4 is selected from N-phenylcarbazoyl.

5. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that, In Formula I, R5 is independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, triphenylsilyl, and carbazole; one or more hydrogens in each substitution may be deuterated.

6. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that, The boron nitrogen compound containing the carbazole group is selected from any one of the following chemical structures:

7. The use of the boron nitrogen compound containing a carbazole group according to any one of claims 1-6 in the preparation of organic electroluminescent devices.

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: Substrate layer; A first electrode is placed on the substrate; An organic light-emitting functional layer is disposed on the first electrode; The second electrode is located on the organic light-emitting functional layer. The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes a boron nitrogen compound containing a carbazole group as described in any one of claims 1-6.

9. A composition, characterized in that, The composition comprises a boron nitrogen compound containing a carbazole group as described in any one of claims 1-6.

10. A formulation, characterized in that, The formulation comprises a boron nitrogen compound containing a carbazole group as described in any one of claims 1-6 and at least one solvent.

11. The application of the organic electroluminescent device according to claim 8 in a display or lighting device.

12. A display or lighting device, characterized in that, The device includes the organic electroluminescent device as described in claim 8.

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