Boron-nitrogen compound containing carbazole group, 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 containing a carbazole group, an OLED with the compound and an organic light-emitting device with the compound. According to the boron-nitrogen compound containing the carbazole group disclosed by the invention, the compound has excellent luminous efficiency and relatively good thermal stability by limiting the combination of an aromatic group, a carbazole structure and a parent nucleus; meanwhile, the boron-nitrogen compound containing the carbazole group provided by the invention is used as a luminescent layer material for a device, so that the organic luminescent device can effectively have lower driving voltage and maintain the stability of the voltage, the luminous efficiency is improved, the service life is obviously prolonged, and the boron-nitrogen compound has a very good application prospect.

Description

Technical Field

[0001] The 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 having the compound, and an organic light-emitting device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that applies voltage to organic electroluminescent elements to inject 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 luminescence. It can convert electrical energy into light energy through organic light-emitting materials.

[0003] Existing light-emitting materials are still insufficient 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 affects the further practical application of this technology.

[0004] Therefore, it is necessary to continue to work hard 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] In order to solve the above technical problems, the present 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 coordinated with an aromatic group, so that the boron nitrogen compound containing a carbazole group is used in an organic electroluminescent device, so that the device can have both high efficiency and long service life.

[0006] The boron nitrogen compound containing a carbazole group provided by the present invention is realized by the following technical scheme: 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: ; 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 arylamino, substituted or unsubstituted C6-C30 aryl, 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, substituted or unsubstituted C5-C36 heteroaryl; when R1-R4 contain substitutions, the substitutions are one or more combinations of hydrogen, deuterium, C1-C24 alkyl, C3-C20 cycloalkyl, C6-C30 aryl; R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, C6-C30 aryl, C5-C36 heteroaryl, C6-C30 aromatic silane; at least one of R1-R5 contains a carbazolyl group.

[0007] Preferably, the hydrogen atoms of the compound of formula I may be partially or fully deuterated.

[0008] Preferably, the formula I can be selected from any one of the following formulas I-1 to I-4: ; In formula I-1 to formula I-3, the substitutions of R2-R5 are as defined above; in formula I-4 to formula I-5, R2 is selected from tert-butyl, phenyl or carbazole, and the substitutions of R3-R5 are as defined above.

[0009] Preferably, in the formula I, R2 is independently selected from methyl, ethyl, propyl, tert-butyl, phenyl, and carbazolyl.

[0010] 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 containing substitution, 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.

[0011] Preferably, in the formula I, R5 is independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, triphenylsilyl, carbazole; and one or more hydrogen in each substitution may be deuterated.

[0012] 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: .

[0013] The present invention also provides a use of the boron nitrogen compound containing a carbazole group in an organic electroluminescent device.

[0014] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising: substrate layer; a first electrode, the first electrode being on the substrate; An organic light-emitting functional layer, the organic light-emitting functional layer is on the first electrode; A second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises the boron nitrogen compound containing a carbazole group as described above.

[0015] The present invention also provides a composition, which comprises the boron nitrogen compound containing a carbazole group as described in Formula I.

[0016] The present invention also provides a preparation, which comprises a boron nitrogen compound containing a carbazole group having a structure as shown in the above formula I or a composition as described above and at least one solvent. The solvent is not particularly limited, and can be used, for example, unsaturated hydrocarbon solvents 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, tetrahydropyran, ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art.

[0017] The organic electroluminescent device of the present invention can be used in an OLED lighting or display device.

[0018] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0019] In summary, compared with the prior art, the present invention has the following beneficial effects: 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 good 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 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 DESCRIPTION

[0020] The following will be described clearly and completely in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0021] The aryl group of the present invention refers to a general term for a monovalent group after removing a hydrogen atom from the aromatic core carbon of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group or a condensed 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-condensed and condensed 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.

[0022] The heteroaryl group of the present invention refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, silicon or nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and may be a heteroaryl group having 6 to 30 carbon atoms, preferably a heteroaryl group having 6 to 20 carbon atoms. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0023] The alkyl group of the present invention includes straight chain and branched chain 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.

[0024] The "cycloalkyl" of the present invention refers to and includes monocyclic, polycyclic and spiroalkyl. Preferred cycloalkyl is a cycloalkyl containing 3 to 20 ring carbon atoms, more preferably a cycloalkyl containing 3 to 12 ring carbon atoms, and particularly preferably a cycloalkyl containing 3 to 6 ring carbon atoms, and includes cyclopropyl, cyclopentyl, cyclohexyl, bicyclo [3.1.1] heptyl, spiro [4.5] decyl, spiro [5.5] undecyl, adamantyl, etc. In addition, the cycloalkyl may be optionally substituted.

[0025] Throughout the specification, unless explicitly described to the contrary, "comprising" any component will be understood to imply the inclusion of other elements, rather than excluding 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" another element, or there may be intervening elements. In addition, "on..." or "above..." means being located above the target portion, and does not necessarily mean being located above according to the direction of gravity.

[0026] 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.

[0027] In one embodiment of the present invention, the light-emitting auxiliary layer in the organic electroluminescent (OLED) device comprises one or more of the compounds represented by the above general formula (I) as light-emitting doping materials.

[0028] 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, 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 includes one or more of the compounds represented by the above general formula (I). Optionally, there is also a covering layer, a protective layer and / or an encapsulation layer on the organic light-emitting functional layer.

[0029] The substrate of the present invention can be any substrate used in a typical organic light-emitting device. 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 stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, the use direction is different.

[0030] As materials for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from known related materials used for OLED devices.

[0031] The present invention is described in detail below in conjunction with specific examples. Synthesis Examples All raw materials and solvents are commercially available unless otherwise specified, and the solvents are used directly without further treatment.

[0032] Example

[0033] Example 1: Synthesis of Compound 001 Synthesis route: ; 1) In a three-necked reaction flask, compound 001-1 (1 mmoL) and compound 001-2 (1 mmoL) were dissolved in 50 mL 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. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-3; 2) Dissolve the intermediate product 001-3 (1 mmoL) and compound 001-4 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-5; 3) Dissolve the intermediate product 001-5 (1 mmoL) and compound 001-6 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, with the eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-7; 4) Dissolve the intermediate product 001-7 (1 mmoL) and compound 2-009-8 (1 mmoL) in 50 mL toluene solution. Under nitrogen atmosphere, add sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL). After reflux for 72 hours, the reaction system is cooled to room temperature. The solvent is removed by rotary evaporation, and the residue is extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried with sodium sulfate. The solvent is removed by vacuum distillation, and the resulting crude product is separated and purified by silica gel chromatography, eluent (dichloromethane: petroleum ether) = 1:4, intermediate product 001-9; 5) The intermediate product 001-9 (1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at -78°C for 4 hours, BBr (3247 mg, 1 mmoL) was slowly added. After reacting at -50°C for 1 hour, the mixture was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting crude product was separated and purified by silica gel chromatography column, with the eluent (dichloromethane: petroleum ether = 1:8) to obtain the final product 001; The structure of the test target product 001: LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 1052.50, and the test value was 1053.16.

[0034] Example 2: Synthesis of Compound 005 Referring to the synthesis steps and reaction conditions of Example 1, compound 005 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1120.56 and the test value was 1121.26.

[0035] Example 3: Synthesis of Compound 013 Referring to the synthesis steps and reaction conditions of Example 1, compound 013 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the test value was 1134.32.

[0036] Example 4: Synthesis of Compound 014 Referring to the synthesis steps and reaction conditions of Example 1, compound 014 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1187.61 and the test value was 1188.35.

[0037] Example 5: Synthesis of Compound 026 Referring to the synthesis steps and reaction conditions of Example 1, compound 026 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1263.64 and the test value was 1264.46.

[0038] Example 6: Synthesis of Compound 027 Referring to the synthesis steps and reaction conditions of Example 1, compound 027 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1229.56 and the test value was 1230.42.

[0039] Example 7: Synthesis of Compound 029 Referring to the synthesis steps and reaction conditions of Example 1, compound 029 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1225.61 and the test value was 1226.43.

[0040] Example 8: Synthesis of Compound 040 Referring to the synthesis steps and reaction conditions of Example 1, compound 040 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1267.51 and the test value was 1268.29.

[0041] Example 9: Synthesis of Compound 042 Referring to the synthesis steps and reaction conditions of Example 1, compound 042 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1181.53 and the test value was 1182.31.

[0042] Example 10: Synthesis of Compound 045 Referring to the synthesis steps and reaction conditions of Example 1, compound 045 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1243.54 and the test value was 1244.38.

[0043] Example 11: Synthesis of Compound 048 Referring to the synthesis steps and reaction conditions of Example 1, compound 048 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1037.56 and the test value was 1038.18.

[0044] Example 12: Synthesis of Compound 056 Referring to the synthesis steps and reaction conditions of Example 1, compound 056 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1111.58 and the test value was 1112.22.

[0045] Example 13: Synthesis of Compound 061 Referring to the synthesis steps and reaction conditions of Example 1, compound 061 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1263.64 and the test value was 1264.28.

[0046] Example 14: Synthesis of Compound 062 Referring to the synthesis steps and reaction conditions of Example 1, compound 062 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1171.58 and the test value was 1172.36.

[0047] Example 15: Synthesis of Compound 063 Referring to the synthesis steps and reaction conditions of Example 1, compound 063 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1161.51 and the test value was 1162.35.

[0048] Example 16: Synthesis of Compound 064 Referring to the synthesis steps and reaction conditions of Example 1, compound 064 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1321.72 and the test value was 1322.58.

[0049] Example 17: Synthesis of Compound 067 Referring to the synthesis steps and reaction conditions of Example 1, compound 067 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1310.59 and the test value was 1311.23.

[0050] Example 18: Synthesis of Compound 068 Compound 068 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 1324.60 and the test value was 1325.34.

[0051] Example 19: Synthesis of Compound 077 Referring to the synthesis steps and reaction conditions of Example 1, compound 077 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1156.59 and the test value was 1157.41.

[0052] Example 20: Synthesis of Compound 088 Referring to the synthesis steps and reaction conditions of Example 1, compound 088 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1020.54 and the test value was 1021.20.

[0053] Example 21: Synthesis of Compound 092 Referring to the synthesis steps and reaction conditions of Example 1, compound 092 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1056.52 and the test value was 1057.20.

[0054] Example 22: Synthesis of Compound 106 Compound 106 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 944.51 and the test value was 945.09.

[0055] Example 23: Synthesis of Compound 110 Referring to the synthesis steps and reaction conditions of Example 1, compound 110 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 933.52 and the test value was 934.08.

[0056] Example 24: Synthesis of Compound 113 Referring to the synthesis steps and reaction conditions of Example 1, compound 113 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): theoretical value 919.41, test value 919.99.

[0057] Example 25: Synthesis of Compound 136 Referring to the synthesis steps and reaction conditions of Example 1, compound 136 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the test value was 1134.22.

[0058] Example 26: Synthesis of Compound 138 Referring to the synthesis steps and reaction conditions of Example 1, compound 138 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1153.53 and the test value was 1154.29.

[0059] Example 27: Synthesis of Compound 148 Referring to the synthesis steps and reaction conditions of Example 1, compound 148 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1209.60 and the test value was 1210.32.

[0060] Example 28: Synthesis of Compound 149 Referring to the synthesis steps and reaction conditions of Example 1, compound 149 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1263.64 and the test value was 1264.30.

[0061] Example 29: Synthesis of Compound 150 Referring to the synthesis steps and reaction conditions of Example 1, compound 150 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1229.56 and the test value was 1230.38.

[0062] Example 30: Synthesis of Compound 159 Referring to the synthesis steps and reaction conditions of Example 1, compound 159 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1176.50 and the test value was 1177.22.

[0063] Example 31: Synthesis of Compound 175 Referring to the synthesis steps and reaction conditions of Example 1, compound 175 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1086.58 and the test value was 1087.24.

[0064] Example 32: Synthesis of Compound 185 Referring to the synthesis steps and reaction conditions of Example 1, compound 185 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1171.58 and the test value was 1172.30.

[0065] Example 33: Synthesis of Compound 186 Compound 186 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 1161.51 and the test value was 1162.27.

[0066] Example 34: Synthesis of Compound 189 Referring to the synthesis steps and reaction conditions of Example 1, compound 189 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1296.72 and the test value was 1297.50.

[0067] Example 35: Synthesis of Compound 190 Referring to the synthesis steps and reaction conditions of Example 1, compound 190 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1310.59 and the test value was 1311.57.

[0068] Example 36: Synthesis of Compound 193 Referring to the synthesis steps and reaction conditions of Example 1, compound 193 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1338.62 and the test value was 1339.40.

[0069] Example 37: Synthesis of Compound 200 Referring to the synthesis steps and reaction conditions of Example 1, compound 200 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1156.59 and the test value was 1157.41.

[0070] Example 38: Synthesis of Compound 215 Compound 215 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 1056.52 and the test value was 1057.12.

[0071] Example 39: Synthesis of Compound 219 Referring to the synthesis steps and reaction conditions of Example 1, compound 219 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1133.56 and the test value was 1134.32.

[0072] Example 40: Synthesis of Compound 237 Referring to the synthesis steps and reaction conditions of Example 1, compound 237 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1054.49 and the test value was 1055.17.

[0073] Example 41: Synthesis of Compound 241 Referring to the synthesis steps and reaction conditions of Example 1, compound 241 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1326.56 and the test value was 1327.40.

[0074] Example 42: Synthesis of Compound 248 Referring to the synthesis steps and reaction conditions of Example 1, compound 248 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1053.50 and the test value was 1054.14.

[0075] Example 43: Synthesis of Compound 253 Referring to the synthesis steps and reaction conditions of Example 1, compound 253 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1338.50 and the test value was 1339.42.

[0076] Example 44: Synthesis of Compound 255 Referring to the synthesis steps and reaction conditions of Example 1, compound 255 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z): the theoretical value was 1160.44 and the test value was 1161.24.

[0077] Several examples of the application of the boron nitrogen compound containing carbazole groups in OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples are purchased from commercial sources or synthesized by the user.

[0078] Fabrication of OLED devices:

[0079] As a reference preparation method for a device embodiment, the present invention evaporates 50-500nm ITO / Ag / ITO on an alkali-free glass substrate as an anode, evaporates a hole injection layer (5nm-20nm), a hole transport layer (50-150nm), a light-emitting auxiliary 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) on the anode, and then co-evaporates Mg and Ag (weight ratio 1:9, 10-50nm) to make a semi-transparent cathode, and then evaporates a cover layer compound. Finally, the light-emitting device is encapsulated using an epoxy resin adhesive in a nitrogen atmosphere.

[0080] In a preferred 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 a UV ozone cleaning treatment is performed in air for 30 minutes. The treated substrate is subjected to vacuum evaporation to deposit ITO / Ag / ITO 100nm as an anode, and then 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 (main material: doping 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 stacked and evaporated, and Mg and Ag (weight ratio 1:9, 14nm) are co-evaporated to make a semi-transparent cathode, and then a compound CPL (65nm) is evaporated as a covering layer. Finally, the light emitting device is encapsulated with epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant material is as follows (particularly preferably selected from the following structure, but it does not mean that the present invention is limited to the following structure): .

[0081] The method provided in the above-mentioned application example 1 was used to prepare application examples 2 to 44 and comparative example 1, the only difference being that the compounds listed in Table 1 were used as luminescent auxiliary materials to replace compound 001 in application example 1. The structure of Ref-1 used in the comparative example is as follows: .

[0082] Performance evaluation of OLED devices:

[0083] The current of the OLED device at different voltages was tested using a Keithley 2365A digital nanovoltmeter, and the current was then divided by the luminous area to obtain the current density of the OLED device at different voltages. The brightness and radiant energy flux density of the OLED device at different voltages were tested 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 / cm 2 ) working voltage Volt and current efficiency (cd / A), BI=E / CIEy, refers to the Blue Index in blue light, and is also a parameter for measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the vertical coordinate color point obtained by bringing the wavelength of the device's luminous half-peak width into the CIE1930 software. The test data is shown in Table 1.

[0084] Table 1 Application examples of light-emitting doping materials and their electronic luminescence characteristics

[0085] As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 44 have lower operating voltage, higher BI luminous efficiency and longer service life. The performance improvement of each application example is based on the fact that the material in the present invention combines the nitrogen-containing heterocyclic ring of the carbazole structure with the aromatic group, has a large conjugated plane, and makes the compound have good thermal stability and a higher glass transition temperature, thereby improving the service life of the device; at the same time, the carbazole group and the aromatic group can have a greater impact on the luminescent properties of the compound, thereby improving the luminous efficiency of the device, and can better achieve the balance of electron and hole transmission and the exciton conversion rate, and reduce the power consumption of the device.

[0086] This specific embodiment is merely an explanation of the present invention and is not a limitation of the present invention. After reading this specification, those skilled in the art may make non-creative modifications to the present embodiment as needed. However, 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 nitrogen compound containing a carbazole group, characterized in that: The boron nitrogen compound containing a carbazole group has a structure shown in the following 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 arylamino, substituted or unsubstituted C6-C30 aryl, 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, substituted or unsubstituted C5-C36 heteroaryl; when R1-R4 contain substitutions, the substitutions are one or more combinations of hydrogen, deuterium, C1-C24 alkyl, C3-C20 cycloalkyl, C6-C30 aryl; R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, C6-C30 aryl, C5-C36 heteroaryl, C6-C30 aromatic silane; at least one of R1-R5 contains a carbazolyl group.

2. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that: The formula I can be selected from any one of the following formulas I-1 to I-4: ； In formula I-1 to formula I-3, the substitution limits of R2-R5 are the same as those defined in claim 1; in formula I-4 to formula I-5, R2 is selected from tert-butyl, phenyl or carbazole, and the substitution limits of R3-R5 are the same as those defined in claim 1.

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

4. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that: In the 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 there is substitution, 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.

5. The boron nitrogen compound containing a carbazole group according to claim 1, characterized in that: In the formula I, R5 is independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, triphenylsilyl, and carbazole; one or more hydrogen 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 a carbazole group is selected from any one of the chemical structures shown below: 。 7. Use of the boron nitrogen compound containing a carbazole group according to any one of claims 1 to 6 in the preparation of an organic electroluminescent device.

8. 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 is on the first electrode; A second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises a boron nitrogen compound containing a carbazole group as claimed in any one of claims 1 to 6.

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

10. A preparation, characterized in that The preparation comprises the boron nitrogen compound containing a carbazole group as claimed in any one of claims 1 to 6 and at least one solvent.

11. Use 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 comprises the organic electroluminescent device as claimed in claim 8.

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