A nitrogen-containing organic compound and its application, an organic electroluminescent device

Abstract

This invention relates to the field of organic electroluminescence technology, specifically to a nitrogen-containing organic compound and its applications, and an organic electroluminescent device. The organic compound contains A structural units and B structural units, and optionally L structural units; the A structural unit has the structure shown in formula (I-1), the B structural unit has the structure shown in formula (I-2), and the L structural unit is a C-type heteroatom with or without A-type heteroatoms. 6‑30 An aromatic compound is formed by removing at least one of two removable hydrogen atoms to form a linking group, wherein the linking group optionally contains at least one substituent selected from combination A. When the organic compound of the present invention is used as the host material of the light-emitting layer in an organic electroluminescent device, it exhibits a lower driving voltage and higher device luminous efficiency.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to a nitrogen-containing organic compound and application thereof, and an organic electroluminescence device. Background Art

[0002] As a new generation of display technology, OLED has gradually entered people's field of vision. Its broad application prospects and rapid technological progress have made OLED one of the most popular research areas in the display field and scientific research product development. Compared with liquid crystal display technology, OLED has the advantages of active luminescence, wide viewing angle, fast response speed, high contrast, high brightness, low power consumption and flexibility.

[0003] Common OLEDs generally include a structure of anode and cathode and an organic layer therebetween. The materials of the organic layer mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and the like.

[0004] The principle of organic electroluminescence is to use the phenomenon that organic substances convert electrical energy into light energy. Under a certain current, holes and electrons migrate from the anode and cathode through the hole transport layer and electron transport layer respectively, and migrate to the light-emitting layer. The electrons and holes recombine in the light-emitting layer to emit light.

[0005] Nowadays, OLED devices or screens still have problems with high driving voltage and low luminous efficiency. In order to improve these defects, on the one hand, the device structure needs to be further optimized, and on the other hand, the performance of each functional layer and luminescent material needs to be improved. Luminescent materials play a vital role in the driving voltage and luminous efficiency of the device.

[0006] The luminescent material can be composed of a single material or a host-guest doped composition. Currently, host-guest doping is the mainstream form, in which the host material has a higher electron and hole mobility, which increases the probability of electron and hole recombination, thereby improving the photoelectric performance of the device.

[0007] Therefore, it is of great significance to develop high-performance organic electroluminescent host materials. Summary of the invention

[0008] The purpose of the present invention is to overcome the defects of the existing organic electroluminescent device, that is, high driving voltage and low current efficiency.

[0009] In order to achieve the above object, the present invention provides a nitrogen-containing organic compound, which contains an A structural unit and a B structural unit, and optionally contains an L structural unit; the A structural unit is a structure shown in formula (I-1), the B structural unit is a structure shown in formula (I-2); the L structural unit is a C containing or not containing a type A heteroatom 6-30The aromatic compound leaves at least one of the connecting groups formed by any two H capable of leaving, and the connecting group optionally contains at least one substituent selected from combination A; the connection mode of the A structural unit and the B structural unit is mode 1 or mode 2;

[0010] Mode 1: The No. 10 position of the A structural unit is directly bonded to the No. 31 position of the B structural unit or is bonded through the L structural unit;

[0011] Mode 2: Any one or any two of the 11th, 12th, 13th, 14th, 21st, 22nd, 23rd, and 24th positions of the A structural unit are directly bonded to the 31st position of the B structural unit or bonded through the L structural unit;

[0012]

[0013] In formula (I-1), X1 and X2 are each independently O or S; if the connection mode of the A structural unit and the B structural unit is mode 2, the N at position 10 in formula (I-1) is replaced by C 6-30 aromatic group substitution; in formula (I-2), at least one of X3 and X4 is N, and the remaining one which is optionally present is CH; R1 and R2 are each independently selected from C containing or not containing A type heteroatom 6-30 Aromatic group; and each of the aromatic groups optionally contains at least one substituent selected from combination A; the combination A contains C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C 1-20 The A-type heteroatom includes at least one of N, O, and S.

[0014] The second aspect of the present invention provides use of the aforementioned nitrogen-containing organic compound in an organic electroluminescent device.

[0015] The third aspect of the present invention provides an organic electroluminescent device, which comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode;

[0016] At least one of the hole blocking layer, the light-emitting layer and the electron transport layer of the organic electroluminescent device contains at least one of the aforementioned nitrogen-containing organic compounds.

[0017] The solution of the present invention has at least the following beneficial effects:

[0018] 1. The new compound formed by the mother core structure and the electron-withdrawing group thereon provided by the present invention has suitable HOMO and LUMO energy levels, can match the adjacent functional layer materials, reduce the injection barrier of electrons and holes, and can reduce the driving voltage when applied to OLED devices; at the same time, the new compound with the electron-withdrawing group has high electron and hole mobility and can balance the migration rate of electrons and holes in the device, and can obtain a wider carrier recombination area when applied to OLED devices, thereby improving the luminous efficiency;

[0019] 2. The compound of the present invention has a relatively high triplet energy level. As a main material, it can effectively prevent the energy from being transferred back to the luminescent dye and thus reduce the luminescence efficiency, and can improve the luminescence efficiency of the device. DETAILED DESCRIPTION

[0020] The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0021] In the present invention, unless otherwise specified, groups of the same type have similar explanations, and the present invention will not elaborate on them one by one.

[0022] "Halogen" means fluorine, chlorine, bromine or iodine.

[0023] The "aromatic compound" and "aromatic group" of the present invention are interpreted in a broad sense, indicating that a cyclic compound or group containing at least one delocalized bond in the molecule or group has "aromatic property".

[0024] "C with or without type A heteroatom 3-30 "At least one of the linking groups formed by the leaving of any two H atoms of the aromatic compound" means that the number of carbon atoms in the aromatic compound is 3-30 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30), and the aromatic compound may contain heteroatoms or may not contain heteroatoms; the linking group may also be selected from C containing or not containing A type heteroatoms 3-30 The aromatic compound leaves two or more of the linking groups formed by any two H atoms that can leave. For example, naphthalene and benzene both leave two H atoms, and the two atoms are bonded to each other to form a linking group.

[0025] “C 1-20"Alkyl" means a straight chain alkyl or branched chain alkyl having a total of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "C 1-10 Alkyl" "C 1~8 Alkyl", "C 1~6 Alkyl", "C 1~3 "Alkyl" and the like have similar definitions, differing only in the total number of carbon atoms.

[0026] "C substituted by at least one halogen 1-20 "Haloalkyl" means "C 1-20 At least one H atom in the "alkyl" is substituted by halogen, and the substituted halogen can be one or more. For example, trifluoromethyl, trifluoroethyl, etc. "C 1~8 "Haloalkyl", "C 1~6 "Haloalkyl", "C 1~3 "Haloalkyl" and the like have similar definitions, differing only in the total number of carbon atoms.

[0027] “C 1-20 "Alkoxy" means "C 1-20 At least one oxygen atom is inserted into the chain of the "alkyl", including straight-chain alkoxy and branched-chain alkoxy, and the oxygen atom is connected to the parent core structure. For example, methoxy, ethoxy, n-propoxy, etc. 1~8 Alkoxy", "C 1~6 Alkoxy", "C 1~3 "Alkoxy" and the like have similar definitions except for the total number of carbon atoms.

[0028] "C substituted by at least one halogen 1-20 "Haloalkoxy" means "C 1-20 At least one H atom in the "alkyl" is substituted by a halogen, which may be one or more halogens, and at least one oxygen atom is inserted into the alkyl chain, and the oxygen atom is connected to the parent core structure. For example, trifluoromethoxy, trifluoroethoxy, etc. 1~8 Haloalkoxy", "C 1~6 Haloalkoxy", "C 1~3 "Haloalkoxy" and the like have similar definitions except for the total number of carbon atoms.

[0029] In method 2, when any two of positions 11, 12, 13, 14, 21, 22, 23, and 24 of the A structural unit are directly bonded to position 31 of the B structural unit or bonded through the L structural unit, it means that two of the B structural units are bonded to one of the A structural unit or bonded through the L structural unit.

[0030] As mentioned above, the first aspect of the present invention provides a nitrogen-containing organic compound, which contains an A structural unit and a B structural unit, and optionally contains an L structural unit; the A structural unit is a structure shown in formula (I-1), the B structural unit is a structure shown in formula (I-2); the L structural unit is a C containing or not containing a type A heteroatom 6-30 The aromatic compound leaves at least one of the connecting groups formed by any two H capable of leaving, and the connecting group optionally contains at least one substituent selected from combination A; the connection mode of the A structural unit and the B structural unit is mode 1 or mode 2;

[0031] Mode 1: The No. 10 position of the A structural unit is directly bonded to the No. 31 position of the B structural unit or is bonded through the L structural unit;

[0032] Mode 2: Any one or any two of the 11th, 12th, 13th, 14th, 21st, 22nd, 23rd, and 24th positions of the A structural unit are directly bonded to the 31st position of the B structural unit or bonded through the L structural unit;

[0033] In formula (I-1), X1 and X2 are each independently O or S; if the connection mode of the A structural unit and the B structural unit is mode 2, the N at position 10 in formula (I-1) is replaced by C 6-30 aromatic group substitution; in formula (I-2), at least one of X3 and X4 is N, and the remaining one which is optionally present is CH; R1 and R2 are each independently selected from C containing or not containing A type heteroatom 6-30 Aromatic group; and each of the aromatic groups optionally contains at least one substituent selected from combination A; the combination A contains C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C 1-20 The A-type heteroatom includes at least one of N, O, and S.

[0034] According to a preferred embodiment 1, the L structural unit is C containing or not containing A type heteroatom 6-24The aromatic compound leaves any two H capable of leaving to form at least one of the connecting groups, and the connecting group optionally contains at least one substituent selected from the combination A; in formula (I-1), X1 and X2 are each independently O or S; if the connection mode of the A structural unit and the B structural unit is mode 2, the N at position 10 in formula (I-1) is replaced by C 6-24 aromatic group substitution; in formula (I-2), at least one of X3 and X4 is N, and the remaining one which is optionally present is CH; R1 and R2 are each independently selected from C containing or not containing A type heteroatom 6-24 Aromatic group; and each of the aromatic groups optionally contains at least one substituent selected from combination A; the combination A contains C 1-12 Alkyl, C 1-12 Alkoxy, C substituted by at least one halogen 1-12 Haloalkyl, C 1-12 The A-type heteroatom includes at least one of N, O, and S.

[0035] According to a preferred embodiment 2, the L structural unit is one or two of the linking groups formed by the removal of any two Hs that can leave from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, and the linking group optionally contains at least one substituent selected from combination A; in formula (I-1), X1 and X2 are each independently O or S; if the connection mode of the A structural unit and the B structural unit is mode 2, the N at position 10 in formula (I-1) is substituted by phenyl, biphenyl, naphthyl, anthracenyl or phenanthryl; in formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is is CH; R1 and R2 are each independently selected from any one of phenyl unsubstituted or substituted by at least one group in combination A, biphenyl unsubstituted or substituted by at least one group in combination A, naphthyl unsubstituted or substituted by at least one group in combination A, anthracenyl unsubstituted or substituted by at least one group in combination A, phenanthryl unsubstituted or substituted by at least one group in combination A, dibenzothiophenyl unsubstituted or substituted by at least one group in combination A, dibenzofuranyl unsubstituted or substituted by at least one group in combination A, and fluorenyl unsubstituted or substituted by at least one group in combination A; the combination A contains C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Haloalkyl, C 1-6 Halogenated alkoxy.

[0036] According to a preferred embodiment 3, the L structural unit is one or two of the linking groups formed by the removal of any two H capable of leaving from benzene, biphenyl, naphthalene, anthracene or phenanthrene, and the linking group optionally contains at least one substituent selected from combination A; the combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

[0037] According to a preferred embodiment 4, the L structural unit is one or two of the linking groups formed by the leaving of any two Hs capable of leaving from benzene, biphenyl, naphthalene, anthracene or phenanthrene, and the linking group optionally contains at least one substituent selected from combination A; the connection mode of the A structural unit and the B structural unit is mode 1; in formula (I-1), X1 and X2 are each independently O or S; in formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is CH; R1 and R2 are each independently selected from unsubstituted or composed of combination A any one of phenyl substituted with at least one group in combination A, biphenyl unsubstituted or substituted with at least one group in combination A, naphthyl unsubstituted or substituted with at least one group in combination A, anthracenyl unsubstituted or substituted with at least one group in combination A, phenanthryl unsubstituted or substituted with at least one group in combination A, dibenzothiophenyl unsubstituted or substituted with at least one group in combination A, dibenzofuranyl unsubstituted or substituted with at least one group in combination A, and fluorenyl unsubstituted or substituted with at least one group in combination A; the combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

[0038] According to a preferred embodiment 5, the organic compound is selected from any one of Compound 1 to Compound 64.

[0039] According to a preferred embodiment 6, the L structural unit is one or two of the linking groups formed by the leaving of any two Hs capable of leaving from benzene, biphenyl, naphthalene, anthracene or phenanthrene, and the linking group optionally contains at least one substituent selected from combination A; the connection mode of the A structural unit and the B structural unit is mode 2; in formula (I-1), X1 and X2 are each independently O or S; the N at position 10 is substituted by phenyl, biphenyl, naphthyl, anthracene or phenanthrene; in formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is CH; R1 and R2 are each independently The present invention relates to any one of phenyl which is unsubstituted or substituted by at least one group in combination A, biphenyl which is unsubstituted or substituted by at least one group in combination A, naphthyl which is unsubstituted or substituted by at least one group in combination A, anthracenyl which is unsubstituted or substituted by at least one group in combination A, phenanthryl which is unsubstituted or substituted by at least one group in combination A, dibenzothiophenyl which is unsubstituted or substituted by at least one group in combination A, dibenzofuranyl which is unsubstituted or substituted by at least one group in combination A, and fluorenyl which is unsubstituted or substituted by at least one group in combination A; the combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

[0040] According to a preferred embodiment 7, the organic compound is selected from any one of Compound 65 to Compound 152.

[0041] According to a preferred embodiment 8, the organic compound is selected from any one of the following:

[0042]

[0043]

[0044] The present invention has no particular restrictions on the specific method for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention according to the specific structural formula provided by the present invention in combination with the conventional process route in the field of organic synthesis, and the present invention hereinafter exemplarily lists several examples to illustrate the preparation method of the compounds of the present invention. Those skilled in the art can also obtain the specific preparation method of all the remaining compounds by replacing the type of raw materials according to the preparation method of the compounds in the following text of the present invention. The present invention no longer describes the preparation methods of all compounds in detail, and those skilled in the art should not be construed as limiting the present invention.

[0045] As mentioned above, the second aspect of the present invention provides the use of the aforementioned nitrogen-containing organic compound in an organic electroluminescent device.

[0046] Preferably, the nitrogen-containing organic compound is present in at least one of a hole blocking layer, a light-emitting layer and an electron transport layer of the organic electroluminescent device.

[0047] According to a preferred specific embodiment, the present invention provides an organic electroluminescent device, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein the one or more organic material layers contain at least one of the aforementioned compounds of the present invention.

[0048] In the present invention, one of the first electrode and the second electrode is an anode, and the other is a cathode.

[0049] According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron injection layer, etc. as organic material layers.

[0050] As mentioned above, the third aspect of the present invention provides an organic electroluminescent device, which comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode;

[0051] At least one of the hole blocking layer, the light-emitting layer and the electron transport layer of the organic electroluminescent device contains at least one of the aforementioned nitrogen-containing organic compounds.

[0052] In a particularly preferred case, the nitrogen-containing organic compound is present in the light-emitting layer of the organic electroluminescent device.

[0053] Preferably, the nitrogen-containing organic compound is present as a green light host material in the light-emitting layer of the organic electroluminescent device. The inventors of the present invention have found that when the compound of the present invention is used as a green light host material in the light-emitting layer of the organic electroluminescent device, the driving voltage of the organic electroluminescent device can be significantly reduced and the luminous efficiency can be improved.

[0054] Preferably, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, a cathode and a covering layer which are stacked in sequence.

[0055] The organic electroluminescent device of the present invention is preferably coated with one or more layers by means of a sublimation method. In this case, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The compounds provided by the present invention are applied by vapor deposition at an initial pressure of 1.5 Pa.

[0056] The organic electroluminescent device of the invention is also preferably coated with one or more layers by an organic vapor deposition method or by means of carrier gas sublimation. -6 The compound is applied at a pressure of 100 Pa to 100 Pa. A particular example of this method is an organic vapor deposition printing method, in which the compound provided by the present invention is directly applied through a nozzle to form a device structure.

[0057] The organic electroluminescent device of the present invention preferably prepares the compound of the present invention into a solution, and forms a layer or a plurality of layer structures by spin coating or by means of any printing method, such as screen printing, flexographic printing, inkjet printing, lithography, more preferably light-induced thermal imaging or inkjet printing. Generally, when multiple layers are made in this way, damage between layers is likely to occur, that is, when one layer is made, when another layer is made with the solution, the solvent in the solution will destroy the already formed layer, which is not conducive to the production of the organic electroluminescent device. However, the compound provided by the present invention can undergo cross-linking under heating or ultraviolet exposure, thereby maintaining the intact layer without being destroyed. The compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in the polymer network.

[0058] The organic electroluminescent device of the invention can be produced as a hybrid system by applying one or more layers by solution and one or more other layers by vapour deposition.

[0059] According to some embodiments of the present invention, the anode material forming the anode is generally preferably a material with a large work function. For example, the anode material used in the present invention is selected from one or more of the following materials: metals, such as vanadium, chromium, copper and gold, or other alloys: metal oxides, such as zinc oxide, indium oxide, indium tin oxide, indium zinc oxide and tin dioxide, combinations of metals and oxides, such as zinc oxide: aluminum, but not limited thereto.

[0060] According to some embodiments of the present invention, the material forming the hole injection layer has the ability to transport holes, so the material of the hole injection layer has the effect of injecting holes into the anode, has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and has excellent thin film forming ability. The HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0061] According to some embodiments of the present invention, the material forming the hole transport layer is a material that can receive holes from the anode or the hole injection layer, move the holes to the light emitting layer, and has high mobility for holes.

[0062] According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of aromatic amine derivatives (such as NPB, SqMA1), hexaazatriphenylene derivatives (such as HACTN), indolecarbazole derivatives, conductive polymers (such as PEDOT / PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorene amine, and spirobifluorene amine, but are not limited thereto.

[0063] According to some embodiments of the present invention, the hole injection layer and the hole transport layer may be formed by, for example, an aromatic amine derivative of the following general formula:

[0064] .

[0065] The groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.

[0066] According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited. Generally, compounds that meet the first and / or second conditions below can be considered for use:

[0067] First: It has a shallower LUMO energy level (smaller absolute value), the purpose of which is to reduce the number of electrons leaving the light-emitting layer, thereby increasing the probability of electrons and holes recombining in the light-emitting layer.

[0068] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to luminescence.

[0069] According to some embodiments of the present invention, the materials forming the electron blocking layer include but are not limited to aromatic amine derivatives (such as NPB) and spirobifluorenamine (such as SpMA2), wherein some electron blocking materials have structures similar to those of hole injection materials and hole transport materials.

[0070] According to some embodiments of the present invention, the light-emitting material of the light-emitting layer is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes and electrons, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0071] According to some embodiments of the present invention, the light-emitting layer may include a host material and a guest material. Preferably, the aforementioned compound provided by the present invention is present in the light-emitting layer as a host material.

[0072] According to some embodiments of the present invention, the guest material is preferably a compound that produces emission via at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal to ligand charge transfer), HLCT (with hybrid CT states) and triplet-triplet annihilation methods.

[0073] According to some embodiments of the present invention, the guest material in the light-emitting layer may include derivatives of perylene, derivatives of anthracene, fluorene derivatives, distyryl aromatic derivatives, aromatic amine derivatives, silicone derivatives, boron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone derivatives, sulfone derivatives, cyano derivatives and xanthene derivatives, but are not limited thereto.

[0074] In some preferred embodiments of the present invention, the sulfone derivative has the general formula shown below:

[0075]

[0076] The ketone derivatives have the general formula shown below:

[0077]

[0078] In the general formulas of the above-mentioned sulfone derivatives and ketone derivatives, R 20 , R 21 , R22 and R 23 Each is independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, diphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and a group represented by a substituent thereof.

[0079] According to some embodiments of the present invention, the material of the hole blocking layer may also preferably be a compound having the following first and / or second conditions:

[0080] First: It has a deeper HOMO energy level (larger absolute value), the purpose of which is to reduce the number of holes leaving the light-emitting layer, thereby increasing the probability of electrons and holes recombining in the light-emitting layer.

[0081] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to luminescence.

[0082] According to some embodiments of the present invention, the material forming the hole blocking layer may include, for example, phenanthroline derivatives (eg, Bphen, BCP), triphenylene derivatives, benzimidazole derivatives, but is not limited thereto.

[0083] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer, and as the electron transport material, a material that can receive electrons from the cathode, move the electrons to the light-emitting layer, and has a high mobility for the electrons is suitable. The electron transport material includes, for example, an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic free radical compound; a hydroxyflavone-metal complex, etc., but is not limited thereto.

[0084] According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and also has excellent film forming ability. The electron injection layer material includes, for example, LiF, CsF, Cs2CO3, LiQ, but is not limited thereto.

[0085] According to some embodiments of the present invention, the cathode material is preferably formed of a material with a small work function, which can smoothly inject electrons into the organic material layer. The cathode material that can be used in the present disclosure can be selected from one or more of the following materials, one or more of Al, Mg and Ag.

[0086] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all the raw materials used are common commercial products.

[0087] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all the raw materials used are common commercial products. Unless otherwise specified, the room temperature described below means 25±1°C.

[0088] Intermediate Preparation Example 1

[0089]

[0090] Synthesis of intermediate A1-1: In a 200 ml three-necked flask, under nitrogen protection, 3-bromo-2-iodobenzofuran (0.05 mol), benzofuran-2-amine (0.05 mol), sodium tert-butoxide (0.125 mol), tri(dibenzylideneacetone)dipalladium (0.5 mmol), tri-tert-butylphosphine (0.5 mmol) and toluene solvent (170 ml) were sequentially added, stirred under nitrogen, and the temperature was raised to reflux for 8 h. HPLC detected that the reaction of the raw materials was complete, the reaction solution was cooled to room temperature, 200 ml of deionized water was added, stirred, separated, the organic phase was washed three times with water, the organic phase was removed by rotary evaporation to remove the solvent, and the residue was separated by silica gel column chromatography to obtain intermediate A1-1 (yield: 78.5%).

[0091] Synthesis of intermediate A1: In a 200 ml three-necked flask, add anhydrous THF (70 ml) to intermediate A1-1 (39 mmol), protect with nitrogen, cool to -78 °C, add 34 ml of 2.5 mol / L n-butyl lithium dropwise, keep at -78 °C for 1 hour, warm to room temperature, add intermediate 9-fluorenone (39 mmol), warm to room temperature, quench with water after 1 hour, filter, extract the filtrate three times with chloroform, dry with anhydrous sodium sulfate, and filter the desiccant to obtain a crude product, dissolve the crude product in 1,2-dichloroethane (70 ml), cool to 0 °C, add trifluoromethanesulfonic acid (70 ml) dropwise, heat under reflux for 2 hours after the addition is complete, cool to room temperature, add NaHCO3 aqueous solution to adjust the solution to neutral, dry with anhydrous sodium sulfate, filter, and decompress the filtrate to dryness, and obtain intermediate A1 (yield: 58.3%) by column chromatography.

[0092] Mass spectrum: C29H17NO2, theoretical value: 411.13, measured value: 411.15. 1H-NMR (400MHz, CDCl3) (ppm) δ = 4.00~4.02 (1H, s), 7.19~7.31 (6H, m), 7.32~7.37 (2H, m), 7.48~7.52 (2H, m), 7.57~7.61 (2H, m), 7.88~7.92 (2H, m), 8.08~8.13 (2H, m).

[0093] Intermediate Preparation Example 2

[0094]

[0095] Synthesis of intermediate A2: The synthesis method is the same as that of intermediate A1 to obtain intermediate A2 (yield: 55.4%).

[0096] Mass spectrum: C29H16ClNO2, theoretical value: 445.09, measured value: 445.15. 1H-NMR (400MHz, CDCl3) (ppm) δ = 4.00~4.02 (1H, s), 7.20~7.31 (5H, m), 7.32~7.37 (1H, m), 7.48~7.53 (3H, m), 7.56~7.61 (2H, m), 7.82~7.86 (1H, m), 7.88~7.92 (2H, m), 8.09~8.13 (1H, m).

[0097] Intermediate Preparation Example 3

[0098]

[0099] Synthesis of intermediate A3: The synthesis method is the same as that of intermediate A1 to obtain intermediate A3 (yield: 52.8%).

[0100] Mass spectrum: C29H15Cl2NO2, theoretical value: 479.05, measured value: 479.02. 1H-NMR (400MHz, CDCl3) (ppm) δ = 4.00~4.02 (1H, s), 7.20~7.24 (2H, m), 7.26~7.30 (2H, m), 7.48~7.53 (4H, m), 7.57~7.61 (2H, m), 7.82~7.86 (2H, m), 7.88~7.91 (2H, m).

[0101] Intermediate Preparation Example 4

[0102]

[0103] Synthesis of intermediate A4-1: The synthesis method is the same as that of intermediate A1-1 to obtain intermediate A4-1 (yield: 79.3%).

[0104] Synthesis of intermediate A4: The synthesis method is the same as that of intermediate A1 to obtain intermediate A4 (yield: 57.6%).

[0105] Mass spectrum: C29H17NS2, theoretical value: 443.08, measured value: 443.03. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 4.00 ~ 4.02 (1H, s), 7.22 ~ 7.27 (2H, m), 7.28 ~ 7.37 (6H, m), 7.70 ~ 7.76 (2H, m), 7.83 ~ 7.88 (2H, m), 7.88 ~ 7.92 (2H, m), 8.08 ~ 8.12 (2H, m).

[0106] Intermediate Preparation Example 5

[0107]

[0108] Synthesis of intermediate A5: The synthesis method is the same as that of intermediate A1 to obtain intermediate A5 (yield: 55.6%).

[0109] Mass spectrum: C29H16ClNS2, theoretical value: 477.04, measured value: 477.10. 1H-NMR (400MHz, CDCl3) (ppm) δ = 4.00~4.02 (1H, s), 7.22~7.26 (1H, m), 7.29~7.37 (5H, m), 7.49~7.53 (1H, m), 7.70~7.75 (2H, m), 7.82~7.92 (5H, m), 8.08~8.12 (1H, m).

[0110] Intermediate Preparation Example 6

[0111]

[0112] Synthesis of intermediate A6: The synthesis method is the same as that of intermediate A1 to obtain intermediate A6 (yield: 55.2%).

[0113] Mass spectrum: C29H15Cl2NS2, theoretical value: 511.00, measured value: 511.05. 1H-NMR (400MHz, CDCl3) (ppm) δ = 4.00~4.02 (1H, s), 7.28~7.35 (4H, m), 7.49~7.53 (2H, m), 7.71~7.76 (2H, m), 7.82~7.87 (4H, m), 7.89~7.91 (2H, m).

[0114] Preparation Example 1

[0115]

[0116] Synthesis of compound 4: In a 500ml three-necked flask, under nitrogen protection, intermediate A1 (50mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (50mmol), activated copper powder (25mmol), 18-crown ether-6 (10mmol), potassium carbonate (125mmol) and NMP (N-methylpyrrolidone) solvent (100ml) were added in sequence, heated with stirring, and the temperature was raised to reflux for 58h. The reaction solution was cooled to room temperature, filtered, and the filtrate was dried under reduced pressure. Column chromatography was performed using petroleum ether / ethyl acetate as eluent to obtain compound 4 (yield: 75.3%).

[0117] Mass spectrum: C50H30N4O2, theoretical value: 718.24, measured value: 718.28. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.17~7.30 (8H, m), 7.31~7.37 (2H, m), 7.47~7.52 (8H, m), 7.53~7.61 (3H, m), 7.88~7.96 (3H, m), 8.20~8.25 (2H, m), 8.34~8.39 (4H, m).

[0118] Preparation Example 2

[0119]

[0120] Synthesis of compound 25: The synthesis method was the same as that of compound 4 to obtain compound 25 (yield: 77.2%).

[0121] Mass spectrum: C45H27N3O2, theoretical value: 641.21, measured value: 641.15. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.18~7.38 (8H, m), 7.44~7.62 (10H, m), 7.84~7.90 (2H, m), 7.91~7.99 (5H, m), 8.15~8.20 (2H, m).

[0122] Preparation Example 3

[0123]

[0124] Synthesis of intermediate 47-1: In a 500 ml three-necked flask, under nitrogen protection, add intermediate A4 (50 mmol), 2-bromo-4-(9,9-dimethyl-9H-fluorene-2-yl)-6-phenyl-1,3,5-triazine (50 mmol), a mixed solution of toluene, ethanol, and water (toluene, ethanol, and water are mixed in a volume ratio of 3:2:1) (220 ml) in sequence, and start stirring. Then add potassium carbonate (125 mmol) and tetrakis(triphenylphosphine)palladium (0.5 mmol) in sequence, raise the temperature to reflux for 6 h, and HPLC detection shows that the raw materials have basically reacted. Add deionized water (300 ml) to the reaction solution, stir for 10 min, wash the organic phase with water three times, combine the organic phases, and dry over anhydrous magnesium sulfate. Filter the desiccant, spin dry the organic solvent, and separate the residue by silica gel chromatography to obtain intermediate 47-1 (yield: 65.8%).

[0125] Synthesis of compound 47: The synthesis method was the same as that of compound 4 to obtain compound 47 (yield: 73.7%).

[0126] Mass spectrum: C59H38N4S2, theoretical value: 866.25, measured value: 866.26. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.66~1.72 (6H, s), 7.15~7.39 (12H, m), 7.46~7.64 (5H, m), 7.68~7.97 (9H, m), 8.05~8.12 (1H, m), 8.24~8.41 (5H, m).

[0127] Preparation Example 4

[0128]

[0129] Synthesis of intermediate 65-1: The synthesis method is the same as that of compound 4 to obtain intermediate 65-1 (yield: 76.3%).

[0130] Synthesis of intermediate 65-2: In a 500 ml three-necked flask, under nitrogen protection, 1,4-dioxane solvent (160 ml), intermediate 65-1 (30 mmol), diboron pinacol ester (30 mmol), potassium acetate (75 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (0.3 mmol) were added in sequence under stirring, and the temperature was raised to reflux for reaction for 4 h. After HPLC detection, the reaction of the raw materials was completed. The reaction solution was cooled to room temperature and then vacuum-dried to obtain a crude product. The crude product was dissolved in toluene solvent, heated and stirred, and the temperature was raised to reflux. The product was decolorized by passing through a silica gel column. The filtrate was vacuum-dried to obtain a small amount of solvent. Ethanol (240 ml) was added for slurrying, and the product was recrystallized from toluene / ethanol to obtain intermediate 65-2 (yield: 90.6%).

[0131] Synthesis of compound 65: In a 500 ml three-necked flask, under nitrogen protection, intermediate 65-2 (27 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (27 mmol), toluene (165 ml), dicyclohexyl (2', 4', 6'-triisopropyl-(1,1'-biphenyl)-2-yl)phosphonic acid (1.35 mmol), PD2(DBA)3 (tri(dibenzylideneacetone)dipalladium, 0.27 mmol), and 20 ml of an aqueous solution containing potassium dihydrogen phosphate (67.5 mmol) were added. Stirring was started and heated to 90 °C for overnight reaction. After 20 h, the reaction temperature was reduced to 40 °C and then reduced to 0 °C for 3 h. The crude product was filtered to obtain a crude product. The crude product was washed with water (250 ml) and then with ethanol (250 ml) to obtain a gray solid. Ethyl acetate / petroleum ether was used as the eluent and silica gel column chromatography was used to separate compound 65 (yield: 89.7%).

[0132] Mass spectrum: C50H30N4O2, theoretical value: 718.24, measured value: 718.18. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.98 ~ 7.02 (1H, m), 7.06 ~ 7.10 (2H, m), 7.19 ~ 7.37 (8H, m), 7.47 ~ 7.53 (8H, m), 7.57 ~ 7.61 (2H, m), 7.76 ~ 7.80 (1H, m), 7.87 ~ 7.92 (1H, m), 8.07 ~ 8.11 (1H, m), 8.21 ~ 8.25 (1H, m), 8.33 ~ 8.39 (4H, m), 8.49 ~ 8.52 (1H, m).

[0133] Preparation Example 5

[0134]

[0135] Synthesis of compound 79: The synthesis method was the same as that of compound 65 to obtain compound 79 (yield: 90.3%).

[0136] Mass spectrum: C57H35N3O2, theoretical value: 793.27, measured value: 793.33. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.95~7. (3H, m), 7.17~7.35 (8H, m), 7.36~7.62 (10H, m), 7.72~7.97 (8H, m), 8.07~8.12 (1H, m), 8.18~8.25 (2H, m), 8.27~8.33 (2H, m), 8.46~8.49 (1H, m).

[0137] Preparation Example 6

[0138]

[0139] Synthesis of intermediate 89-1: The synthesis method is the same as that of compound 4 to obtain intermediate 89-1 (yield: 57.4%).

[0140] Synthesis of intermediate 89-2: The synthesis method is the same as that of intermediate 65-2 to obtain intermediate 89-2 (yield: 89.5%).

[0141] Synthesis of Compound 89: The synthesis method was the same as that of Compound 65 to obtain Compound 89 (yield: 90.7%).

[0142] Mass spectrum: C62H38N4S2, theoretical value: 902.25, measured value: 902.33. 1H-NMR (400MHz, CDCl3) (ppm) δ=6.96~7.11 (3H, m), 7.20~7.28 (7H, m), 7.29~7.45 (7H, m), 7.45~7.54 (4H, m), 7.69~7.81 (7H, m), 7.83~7.99 (7H, m), 8.07~8.12 (1H, m), 8.18~8.24 (1H, m), 8.54~8.56 (1H, m).

[0143] Preparation Example 7

[0144]

[0145] Synthesis of compound 105: The synthesis method was the same as that of compound 65 to obtain compound 105 (yield: 89.3%).

[0146] Mass spectrum: C56H34N4O2, theoretical value: 794.27, measured value: 794.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.96~7.11 (3H, m), 7.17~7.38 (8H, m), 7.46~7.54 (8H, m), 7.56~7.64 (3H, m), 7.67~7.80 (2H, m), 7.88~7.93 (1H, m), 8.07~8.12 (1H, m), 8.23~8.28 (1H, m), 8.32~8.41 (6H, m), 8.42~8.45 (1H, m).

[0147] Preparation Example 8

[0148]

[0149] Synthesis of intermediate 115-1: The synthesis method is the same as that of intermediate 47-1 to obtain intermediate 115-1 (yield: 68.3%).

[0150] Synthesis of compound 115: The synthesis method was the same as that of compound 65 to obtain compound 115 (yield: 89.7%).

[0151] Mass spectrum: C65H39N3O2, theoretical value: 893.30, measured value: 893.24. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.95~7.11 (3H, m), 7.18~7.38 (10H, m), 7.47~7.66 (8H, m), 7.76~7.81 (1H, m), 7.87~8.12 (14H, m), 8.21~8.25 (1H, m), 8.44~8.48 (2H, m).

[0152] Preparation Example 9

[0153]

[0154] Synthesis of compound 131: The synthesis method was the same as that of compound 65 to obtain compound 131 (yield: 90.2%).

[0155] Mass spectrum: C57H35N3S2, theoretical value: 825.23, measured value: 825.26. 1H-NMR (400MHz, CDCl3) (ppm) δ=6.96~7.11 (3H, m), 7.20~7.38 (8H, m), 7.44~7.64 (7H, m), 7.66~7.81 (4H, m), 7.83~7.98 (7H, m), 8.05~8.12 (1H, m), 8.17~8.24 (2H, m), 8.27~8.32 (1H, m), 8.35~8.42 (2H, m).

[0156] Preparation Example 10

[0157]

[0158] Synthesis of intermediate 133-1: The synthesis method is the same as that of compound 4 to obtain intermediate 133-1 (yield: 75.8%).

[0159] Synthesis of intermediate 133-2: The synthesis method is the same as that of intermediate 65-2 to obtain intermediate 133-2 (yield: 88.4%).

[0160] Synthesis of compound 133: The synthesis method was the same as that of compound 65 to obtain compound 133 (yield: 87.6%).

[0161] Mass spectrum: C65H39N7O2, theoretical value: 949.32, measured value: 949.33. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.95~7.11 (3H, m), 7.18~7.32 (6H, m), 7.46~7.54 (14H, m), 7.56~7.62 (2H, m), 7.75~7.81 (2H, m), 8.06~8.12 (2H, m), 8.31~8.41 (8H, m), 8.69~8.72 (2H, m).

[0162] Preparation Example 11

[0163]

[0164] Synthesis of intermediate 151-1: The synthesis method is the same as that of compound 4 to obtain intermediate 151-1 (yield: 74.9%).

[0165] Synthesis of intermediate 151-2: The synthesis method is the same as that of intermediate 65-2 to obtain intermediate 151-2 (yield: 88.1%).

[0166] Synthesis of compound 151: The synthesis method was the same as that of compound 65 to obtain compound 151 (yield: 88.3%).

[0167] Mass spectrum: C77H47N7S2, theoretical value: 1133.33, measured value: 1133.35. 1H-NMR (400MHz, CDCl3) (ppm) δ=6.96~7.11 (3H, m), 7.20~7.38 (6H, m), 7.39~7.54 (12H, m), 7.58~7.64 (2H, m), 7.67~7.81 (10H, m), 7.82~7.90 (2H, m), 8.06~8.12 (2H, m), 8.30~8.41 (8H, m), 9.39~9.44 (1H, m), 9.50~9.54 (1H, m).

[0168] Device Example 1

[0169] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0170] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10 -4 Pa, vacuum evaporate NPD-9 on the above anode layer as a hole injection layer, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 5nm; then evaporate NPB as a hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 60nm; vacuum evaporate TCTA on the hole transport layer as an electron blocking layer, the evaporation rate is 0.1nm / s, and the thickness is 10nm;

[0171] The light-emitting layer of the device is vacuum-evaporated on the hole transport layer. The light-emitting layer includes a main material and a guest material. The evaporation rate of the main material compound 4 is adjusted to 0.1 nm / s by a multi-source co-evaporation method. The evaporation rate of the guest material Ir(ppy)3 is set to 8% of the evaporation rate of the main material. The total evaporation film thickness is 30 nm.

[0172] The electron transport layer of the device was vacuum-deposited on the light-emitting layer. The evaporation rate of ET-1 and ET-2 was adjusted to 0.1nm / s by using the multi-source co-evaporation method, and the total evaporation film thickness was 30nm.

[0173] LiF with a thickness of 1 nm was vacuum evaporated on the electron transport layer (ETL) as the electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[0174] Structure of the substances involved:

[0175]

[0176] Device Examples 2 to 11

[0177] Organic light-emitting devices of device examples 2 to 11 were prepared by a method similar to that of device example 1, except that compound 4 in device example 1 was replaced by the corresponding compound in Table 1.

[0178] Device Comparison Examples 1 to 2

[0179] Organic electroluminescent devices of device comparative examples 1-2 were prepared by a method similar to that of device example 1, except that compound 4 in device example 1 was replaced by Ref1 and Ref2, respectively.

[0180]

[0181] Test Example 1

[0182] At brightness 10000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in device embodiments 1 to 11 and device comparative examples 1 to 2 were measured. The results are shown in Table 1.

[0183] Table 1

[0184]

[0185] It can be seen from the experimental results shown in Table 1 that, compared with the prior art, the organic electroluminescent device containing the compound of the present invention has a lower driving voltage and a higher luminous efficiency.

[0186] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. A nitrogen-containing organic compound, characterized in that The organic compound contains an A structural unit and a B structural unit, and optionally contains an L structural unit; the A structural unit is a structure represented by formula (I-1), and the B structural unit is a structure represented by formula (I-2); the L structural unit is one or two of the connecting groups formed by benzene, biphenyl, naphthalene, anthracene, and phenanthrene with the two H atoms leaving any one of the connecting groups, and the connecting group optionally contains at least one substituent selected from combination A; the connection mode of the A structural unit and the B structural unit is mode 1 or mode 2; Mode 1: The No. 10 position of the A structural unit is directly bonded to the No. 31 position of the B structural unit or is bonded through the L structural unit; Mode 2: Any one or any two of the 12th and 22nd positions of the A structural unit are directly bonded to the 31st position of the B structural unit or bonded through the L structural unit; In formula (I-1), X1 and X2 are each independently O or S; if the connection mode of the A structural unit and the B structural unit is mode 2, the N at position 10 in formula (I-1) is substituted by phenyl, biphenyl, naphthyl, anthracenyl or phenanthryl; In formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is CH; R1 and R2 are each independently selected from any one of a phenyl group that is unsubstituted or substituted by at least one group in combination A, a biphenyl group that is unsubstituted or substituted by at least one group in combination A, a naphthyl group that is unsubstituted or substituted by at least one group in combination A, an anthracenyl group that is unsubstituted or substituted by at least one group in combination A, a phenanthrenyl group that is unsubstituted or substituted by at least one group in combination A, and a fluorenyl group that is unsubstituted or substituted by at least one group in combination A, wherein the combination A contains C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C substituted by at least one halogen 1-20 Halogenated alkoxy.

2. The organic compound according to claim 1, characterized in that The combination A contains C 1-12 Alkyl, C 1-12 Alkoxy, C substituted by at least one halogen 1-12 Haloalkyl, C substituted by at least one halogen 1-12 Halogenated alkoxy.

3. The organic compound according to claim 2, characterized in that The combination A contains C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Haloalkyl, C substituted by at least one halogen 1-6 Halogenated alkoxy.

4. The organic compound according to claim 3, characterized in that The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

5. The organic compound according to any one of claims 1 to 4, characterized in that The connection mode of the A structural unit and the B structural unit is mode 1; In formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is CH; R1 and R2 are each independently selected from any one of a phenyl group that is unsubstituted or substituted by at least one group in combination A, a biphenyl group that is unsubstituted or substituted by at least one group in combination A, a naphthyl group that is unsubstituted or substituted by at least one group in combination A, an anthracenyl group that is unsubstituted or substituted by at least one group in combination A, a phenanthrenyl group that is unsubstituted or substituted by at least one group in combination A, and a fluorenyl group that is unsubstituted or substituted by at least one group in combination A; The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

6. The organic compound according to claim 5, characterized in that The organic compound is selected from any one of the following:

7. The organic compound according to any one of claims 1 to 4, characterized in that The connection mode of the A structural unit and the B structural unit is mode 2; In formula (I-2), at least one of X3 and X4 is N, and the remaining one that is optionally present is CH; R1 and R2 are each independently selected from any one of a phenyl group that is unsubstituted or substituted by at least one group in combination A, a biphenyl group that is unsubstituted or substituted by at least one group in combination A, a naphthyl group that is unsubstituted or substituted by at least one group in combination A, an anthracenyl group that is unsubstituted or substituted by at least one group in combination A, a phenanthrenyl group that is unsubstituted or substituted by at least one group in combination A, and a fluorenyl group that is unsubstituted or substituted by at least one group in combination A; The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy.

8. The organic compound according to claim 7, characterized in that The organic compound is selected from any one of the following:

9. The organic compound according to any one of claims 1 to 4, characterized in that The organic compound is selected from any one of the following:

10. Use of the nitrogen-containing organic compound according to any one of claims 1 to 9 in an organic electroluminescent device; And / or, the nitrogen-containing organic compound is present in at least one of a hole blocking layer, a light-emitting layer and an electron transporting layer of the organic electroluminescent device.

11. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode; At least one of the hole blocking layer, the light-emitting layer and the electron transport layer of the organic electroluminescent device contains at least one of the nitrogen-containing organic compounds according to any one of claims 1 to 9.

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