A boron nitride compound containing a carbazole group, an OLED having the compound, and an organic light-emitting device

Abstract

The present invention relates to the technical field of organic photoelectric material preparation, and in particular to a boron-nitrogen compound containing a carbazole group, an OLED comprising the compound, and an organic light-emitting device. The boron-nitrogen compound containing a carbazole group of the present invention, by limiting the combination of an aromatic group, a carbazole-like structure, and a parent core, has excellent luminous efficiency and good thermal stability. Furthermore, the boron-nitrogen compound containing a carbazole group provided by the present invention, when used as a light-emitting layer material in a device, can effectively lower the driving voltage of the organic light-emitting device while maintaining voltage stability, improve luminous efficiency, and significantly extend its operating life, thus having excellent application prospects.

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 containing a carbazole group, an OLED and an organic light-emitting device having the compound. Background Art

[0002] 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 organic electroluminescent elements, injecting holes from the anode and electrons from the cathode into the light-emitting layer respectively. The injected holes and electrons recombine to form excitons, resulting in light emission.

[0003] Existing luminescent materials still have shortcomings in improving device performance. Even if multiple materials are used in combination, display technology still has problems such as high driving voltage and short display life, which seriously affect the further practical 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, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems. Summary of the Invention

[0005] To address the above technical problems, the present invention provides a boron-nitrogen compound containing a carbazole group, an OLED comprising the compound, and a display or lighting device. The provided compound contains a carbazole structure and is coordinated with an aromatic group. Thus, the boron-nitrogen compound containing the carbazole group can be used in an organic electroluminescent device, enabling the device to achieve both high efficiency and a long operating life.

[0006] The present invention provides a boron nitrogen compound containing a carbazole group, which is achieved through the following technical solutions:

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

[0008] ;

[0009] In Formula I, R1 and R2 are each independently selected from a C1-C24 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C36 heteroaryl group. R1 and R2 may be fused with an adjacent phenyl group. R3 and R4 are each independently selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C5-C36 heteroaryl group. When R1-R4 are substituted, the substitution is one or more combinations of hydrogen, deuterium, a C1-C24 alkyl group, a C3-C20 cycloalkyl group, and a C6-C30 aryl group. R5 is independently selected from hydrogen, deuterium, a C1-C24 alkyl group, a C6-C30 aryl group, a C5-C36 heteroaryl group, and a C6-C30 aromatic silyl group. At least one of R1-R5 contains a carbazolyl group.

[0010] Preferably, the hydrogen atoms of the compound of formula I may be partially or fully deuterated.

[0011] Preferably, the formula I can be selected from any one of the following formulas I-1 to I-4:

[0012] ;

[0013] In formulas I-1 to I-3, the substitutions of R2-R5 are as defined above; in formulas I-4 to I-5, R2 is selected from tert-butyl, phenyl or carbazolyl, and the substitutions of R3-R5 are as defined above.

[0014] Preferably, in the formula I, R2 is independently selected from methyl, ethyl, propyl, tert-butyl, phenyl, and carbazolyl.

[0015] 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-phenylcarbazolyl; when substituted, the substitution 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-phenylcarbazolyl.

[0016] Preferably, in Formula I, R5 is independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, triphenylsilyl, and carbazolyl; and one or more hydrogens in each substitution may be deuterated.

[0017] According to one or more embodiments, the present invention provides a boron nitrogen compound containing a carbazole group, selected from any one of the chemical structures shown below:

[0018] .

[0019] The present invention also provides a use of the boron nitrogen compound containing a carbazole group in an organic electroluminescent device.

[0020] The present invention also provides an organic electroluminescent device, comprising:

[0021] substrate layer;

[0022] a first electrode, the first electrode being on the substrate;

[0023] an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode;

[0024] a second electrode, the second electrode being on the organic light-emitting functional layer;

[0025] The organic light-emitting functional layer includes a light-emitting layer; the light-emitting layer includes the boron nitrogen compound containing a carbazole group as described above.

[0026] The present invention also provides a composition comprising the boron nitrogen compound containing a carbazole group as described in Formula I.

[0027] The present invention also provides a preparation comprising a boron nitrogen compound containing a carbazole group having a structure as shown in Formula I above or the composition as described above and at least one solvent. The solvent is not particularly limited and can 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, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran and tetrahydropyran, and ester solvents such as alkyl benzoates.

[0028] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices.

[0029] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0030] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0031] The boron nitrogen compound containing a carbazole group of the present invention is limited to a carbazole group, an aryl-substituted carbazole group and an aromatic group to obtain a compound, so that the compound has excellent luminous efficiency and a long service life. At the same time, the boron nitrogen compound containing a carbazole group provided by the present invention is used in a device, which can effectively enable the organic light-emitting device to have a lower driving voltage and maintain voltage stability, and the luminous efficiency is improved, and the service life of the device can also be improved. DETAILED DESCRIPTION

[0032] 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.

[0033] The aryl group of the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group or a fused ring aryl group. 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, anthracenyl, phenanthrenyl or pyrenyl, but are not limited thereto. Aryl or aromatic group - as used herein, non-fused and fused systems are considered. 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 the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene, perylene and azulene, with preference given to phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. 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-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl.

[0034] The term "heteroaryl" as used herein refers to a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, including but not limited to oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group may be a monocyclic heteroaryl or a condensed-ring heteroaryl group, and may have 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms. Examples include, but are not limited to, pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.

[0035] The alkyl group of the present invention includes straight-chain and branched alkyl groups. It can be an alkyl group having 1 to 24 carbon atoms, and preferably an alkyl group having 1 to 4 carbon atoms, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, etc. In addition, the alkyl group can be optionally substituted.

[0036] The term "cycloalkyl" as used herein refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups include those having 3 to 20 ring carbon atoms, more preferred cycloalkyl groups include those having 3 to 12 ring carbon atoms, and particularly preferred cycloalkyl groups include those having 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.

[0037] 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.

[0038] An object of the present invention is to provide an organic electroluminescent device, which includes: a substrate layer; a first electrode, which is on the substrate; 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, and the light-emitting layer includes a boron nitrogen compound having a carbazole structure fragment.

[0039] In one embodiment of the present invention, the light-emitting auxiliary layer in the organic electroluminescent (OLED) device comprises one or more compounds represented by the above general formula (I) as light-emitting doping materials.

[0040] 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 light-assisting 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 one or more 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.

[0041] 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.

[0042] 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.

[0043] The present invention will be described in detail below with reference to specific examples. Synthesis Examples All raw materials and solvents were commercially available unless otherwise specified, and the solvents were used directly without further treatment.

[0044] Example

[0045] Example 1: Synthesis of Compound 001

[0046] Synthesis route:

[0047] ;

[0048] 1) In a three-necked reaction flask, dissolve compound 001-1 (1 mmol) and compound 001-2 (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 with an eluent ratio of dichloromethane:petroleum ether (1:4) to obtain the intermediate product 001-3.

[0049] 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.

[0050] 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.

[0051] 4) Dissolve intermediate 001-7 (1 mmol) and compound 2-009-8 (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.

[0052] 5) Dissolve the intermediate product 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 BBr (3247 mg, 1 mmol). After reacting at -50°C for 1 hour, warm the mixture to room temperature, add N,N-diisopropylethylamine (387 mg, 3 mmol), and heat to 120°C for 12 hours. After cooling to room temperature, add 5 mL of 1 M sodium acetate solution. 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 using a 1:8 ratio of dichloromethane to petroleum ether as the eluent to obtain the final product 001.

[0053] The structure of the test target product 001 was analyzed by liquid chromatography-mass spectrometry (LC-MS) (m / z): the theoretical value was 1052.50 and the test value was 1053.16.

[0054] Example 2: Synthesis of Compound 005

[0055] Compound 005 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 005 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1120.56 and the measured value was 1121.26.

[0056] Example 3: Synthesis of Compound 013

[0057] Compound 013 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 013 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the measured value was 1134.32.

[0058] Example 4: Synthesis of Compound 014

[0059] Compound 014 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. Liquid chromatography-mass spectrometry analysis gave an LC-MS (m / z) of 1187.61 and a measured value of 1188.35.

[0060] Example 5: Synthesis of Compound 026

[0061] Compound 026 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 026 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1263.64 and the measured value was 1264.46.

[0062] Example 6: Synthesis of Compound 027

[0063] Compound 027 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1229.56 and the measured value was 1230.42.

[0064] Example 7: Synthesis of Compound 029

[0065] Compound 029 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1225.61 and the measured value was 1226.43.

[0066] Example 8: Synthesis of Compound 040

[0067] Compound 040 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. Liquid chromatography-mass spectrometry analysis gave an LC-MS (m / z) of 1267.51 and a measured value of 1268.29.

[0068] Example 9: Synthesis of Compound 042

[0069] Compound 042 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 042 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1181.53 and the measured value was 1182.31.

[0070] Example 10: Synthesis of Compound 045

[0071] Compound 045 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1243.54 and the measured value was 1244.38.

[0072] Example 11: Synthesis of Compound 048

[0073] Compound 048 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 048 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1037.56 and the measured value was 1038.18.

[0074] Example 12: Synthesis of Compound 056

[0075] Compound 056 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 056 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1111.58 and the measured value was 1112.22.

[0076] Example 13: Synthesis of Compound 061

[0077] Compound 061 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1263.64 and the measured value was 1264.28.

[0078] Example 14: Synthesis of Compound 062

[0079] Compound 062 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 062 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1171.58 and the measured value was 1172.36.

[0080] Example 15: Synthesis of Compound 063

[0081] Compound 063 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 063 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1161.51 and the measured value was 1162.35.

[0082] Example 16: Synthesis of Compound 064

[0083] Compound 064 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 064 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1321.72 and the measured value was 1322.58.

[0084] Example 17: Synthesis of Compound 067

[0085] Compound 067 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 067 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1310.59 and the measured value was 1311.23.

[0086] Example 18: Synthesis of Compound 068

[0087] Compound 068 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 068 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1324.60 and the measured value was 1325.34.

[0088] Example 19: Synthesis of Compound 077

[0089] Compound 077 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1156.59 and the measured value was 1157.41.

[0090] Example 20: Synthesis of Compound 088

[0091] Compound 088 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 088 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1020.54 and the measured value was 1021.20.

[0092] Example 21: Synthesis of Compound 092

[0093] 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): the theoretical value was 1056.52 and the measured value was 1057.20.

[0094] Example 22: Synthesis of Compound 106

[0095] Compound 106 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 106 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 944.51 and the measured value was 945.09.

[0096] Example 23: Synthesis of Compound 110

[0097] Compound 110 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 110 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 933.52 and the measured value was 934.08.

[0098] Example 24: Synthesis of Compound 113

[0099] Compound 113 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 113 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): theoretical value 919.41, measured value 919.99.

[0100] Example 25: Synthesis of Compound 136

[0101] Compound 136 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 136 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the measured value was 1134.22.

[0102] Example 26: Synthesis of Compound 138

[0103] Compound 138 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 138 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1153.53 and the measured value was 1154.29.

[0104] Example 27: Synthesis of Compound 148

[0105] 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): the theoretical value was 1209.60 and the measured value was 1210.32.

[0106] Example 28: Synthesis of Compound 149

[0107] Compound 149 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The LC-MS (m / z) was analyzed by liquid chromatography-mass spectrometry: the theoretical value was 1263.64, and the measured value was 1264.30.

[0108] Example 29: Synthesis of Compound 150

[0109] Compound 150 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 150 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1229.56 and the measured value was 1230.38.

[0110] Example 30: Synthesis of Compound 159

[0111] 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): the theoretical value was 1176.50 and the measured value was 1177.22.

[0112] Example 31: Synthesis of Compound 175

[0113] Compound 175 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 175 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1086.58 and the measured value was 1087.24.

[0114] Example 32: Synthesis of Compound 185

[0115] Compound 185 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 185 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1171.58 and the measured value was 1172.30.

[0116] Example 33: Synthesis of Compound 186

[0117] Compound 186 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 186 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1161.51 and the measured value was 1162.27.

[0118] Example 34: Synthesis of Compound 189

[0119] Compound 189 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 189 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1296.72 and the measured value was 1297.50.

[0120] Example 35: Synthesis of Compound 190

[0121] Compound 190 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 190 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1310.59 and the measured value was 1311.57.

[0122] Example 36: Synthesis of Compound 193

[0123] Compound 193 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 193 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1338.62 and the measured value was 1339.40.

[0124] Example 37: Synthesis of Compound 200

[0125] Compound 200 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 200 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1156.59 and the measured value was 1157.41.

[0126] Example 38: Synthesis of Compound 215

[0127] Compound 215 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 215 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1056.52 and the measured value was 1057.12.

[0128] Example 39: Synthesis of Compound 219

[0129] Compound 219 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 219 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the measured value was 1134.32.

[0130] Example 40: Synthesis of Compound 237

[0131] Compound 237 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 237 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1054.49 and the measured value was 1055.17.

[0132] Example 41: Synthesis of Compound 241

[0133] Compound 241 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 241 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1326.56 and the measured value was 1327.40.

[0134] Example 42: Synthesis of Compound 248

[0135] Compound 248 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 248 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1053.50 and the measured value was 1054.14.

[0136] Example 43: Synthesis of Compound 253

[0137] Compound 253 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 253 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1338.50 and the measured value was 1339.42.

[0138] Example 44: Synthesis of Compound 255

[0139] Compound 255 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 255 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1160.44 and the measured value was 1161.24.

[0140] Several examples of the application of the boron nitrogen compound containing a carbazole group in OLED devices are listed below to further illustrate the beneficial effects of the compound of the present invention. The materials used in the examples were purchased commercially or synthesized by ourselves.

[0141] Fabrication of OLED devices:

[0142] 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, 10-50nm). A capping compound is then evaporated. Finally, the light-emitting device is encapsulated with an epoxy resin adhesive under a nitrogen atmosphere.

[0143] In a preferred embodiment, the OLED device provided by the present invention comprises the following: an alkali-free glass substrate is first cleaned with isopropyl alcohol in 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 (HT:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a luminescent auxiliary layer (BP, 5nm), a blue emitting layer (host 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 on the anode. Mg and Ag (weight ratio 1:9, 14nm) 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):

[0144] .

[0145] Application Examples 2 to 44 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 luminescent auxiliary materials instead of Compound 001 in Application Example 1. The structure of Ref-1 used in the Comparative Example is as follows: .

[0146] Performance evaluation of OLED devices:

[0147] 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.

[0148] Table 1 Application examples of luminescent doping materials and their electronic luminescence characteristics

[0149]

[0150] As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 44 have lower operating voltages, higher BI luminous efficiencies, and longer service lives. The performance improvements in each application example are based on the fact that the materials of the present invention combine a nitrogen-containing heterocycle with an aromatic group in a carbazole structure, resulting in a large conjugated plane. This gives the compound good thermal stability and a high glass transition temperature, thereby extending the service life of the device. Furthermore, the combination of the carbazole group and the aromatic group can significantly influence the luminescent properties of the compound, thereby improving the luminous efficiency of the device, better achieving balanced electron and hole transport and exciton conversion efficiency, and reducing device power consumption.

[0151] 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 containing a carbazole group, characterized in that: The boron nitrogen compound containing a carbazole group is selected from any one of the following chemical structures:

2. Use of the boron nitrogen compound containing a carbazole group according to claim 1 in the preparation of an organic electroluminescent device.

3. 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 light-emitting layer; the light-emitting layer comprises the boron nitrogen compound containing a carbazole group as claimed in claim 1 .

4. A composition, characterized in that The composition comprises the boron nitrogen compound containing a carbazole group as claimed in claim 1.

5. A preparation, characterized in that The preparation comprises the boron nitrogen compound containing a carbazole group as claimed in claim 1 and at least one solvent.

6. Use of the organic electroluminescent device according to claim 3 in a display or lighting device.

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

Images