An organic compound containing a spiro ring structure and its application, an organic electroluminescent device

Abstract

The present invention relates to the technical field of organic electroluminescence, and in particular to an organic compound containing a spirocyclic structure and its application, and an organic electroluminescent device. 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 shown in formula (I-1); the B structural unit is selected from -R 1 ,‑N(R 2 )(R 3 ) in any one; R 1 , R 2 and R 3 Each independently selected from C containing or not containing A type heteroatom 6‑30 Any one of the aromatic groups formed by the aromatic compound leaving any one of the H groups that can leave, the aromatic group optionally containing at least one substituent selected from the combination A; the L structural unit is C containing or not containing A type heteroatom 6‑30 The aromatic compound leaves at least one of the connecting groups formed by any two H atoms that can leave. The compound of the present invention can be used in an organic electroluminescent device to effectively improve the luminous efficiency.

Description

Technical Field

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

[0002] In recent years, organic electroluminescent technology has gradually entered people's field of vision as a new generation of display technology. Its broad application prospects and rapid technological progress have made organic electroluminescent technology one of the most popular research areas in the display field and scientific research product development.

[0003] The principle of organic electroluminescence is to use organic matter to convert electrical energy into light energy. Common organic light-emitting elements 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, electron blocking layer materials, luminescent materials, hole blocking layer materials, electron transport materials, electron injection materials, etc.

[0004] At present, organic electroluminescent devices or screens still have defects such as high driving voltage and low current efficiency. During the research process, it was found that the excitons in the light-emitting layer will diffuse to both sides of the light-emitting layer, resulting in reduced exciton utilization, further affecting the efficiency and life of the device.

[0005] Therefore, developing barrier layer materials with high triplet energy levels can improve the luminescence efficiency and service life of the device, which is of great practical significance. Summary of the invention

[0006] The purpose of the present invention is to overcome the defects of the existing organic electroluminescent devices, such as high driving voltage, low luminous efficiency and short service life.

[0007] In order to achieve the above object, the present invention provides an organic compound containing a spirocyclic structure, wherein 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 shown in formula (I-1); the B structural unit is selected from any one of -R1 and -N(R2)(R3); R1, R2 and R3 are each independently selected from C containing or not containing a type A heteroatom 6-30 Any one of the aromatic groups formed by the aromatic compound leaving any one of the H groups that can leave, the aromatic group optionally containing at least one substituent selected from the combination A; the L structural unit is C containing or not containing A type 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;

[0008] Mode 1: Position 10 of the A structural unit is directly bonded to the B structural unit or bonded through the L structural unit;

[0009] 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 B structural unit or bonded through the L structural unit;

[0010]

[0011] 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;

[0012] 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 Haloalkoxy, C with or without type A heteroatom 6-30 Aromatic groups;

[0013] The type A heteroatom includes at least one of N, O, and S.

[0014] The second aspect of the present invention provides use of the aforementioned organic compound containing a spiro structure 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 transport layer, the light emitting layer and the electron blocking layer of the organic electroluminescent device contains at least one of the aforementioned organic compounds containing a spiro structure.

[0017] The solution of the present invention has at least the following specific advantages:

[0018] The present invention has at least the following specific advantages:

[0019] 1. The mother core structure provided by the present invention and the new compound formed by the electron-donating group thereon have a suitable HOMO energy level, which can match the adjacent functional layer materials and reduce the hole injection barrier; the higher LUMO energy level can block electrons and prevent leakage, and can improve the driving voltage and luminous efficiency of the device;

[0020] 2. The mother core structure of the present invention is a spirocyclic structure, and the structural space presents a three-dimensional structure, has a high triplet energy level, can effectively block the diffusion of excitons, and can improve the luminous efficiency when applied to OLED devices. DETAILED DESCRIPTION

[0021] 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.

[0022] 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.

[0023] "Halogen" means fluorine, chlorine, bromine or iodine.

[0024] 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 "aromaticity".

[0025] "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 hydrogen atoms that can leave. For example, naphthalene and benzene both leave two hydrogen atoms, and the two hydrogen atoms are bonded to each other to form a linking group.

[0026] “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.

[0027] "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.

[0028] “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.

[0029] "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.

[0030] "Naphtho[2,1-b]benzofuranyl" means a radical formed by the removal of any leaving H from the compound shown below:

[0031] ,

[0032] 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 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 units or bonded through the L structural unit.

[0033] As mentioned above, the first aspect of the present invention provides an organic compound containing a spirocyclic structure, wherein 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 shown in formula (I-1); the B structural unit is selected from any one of -R1, -N(R2)(R3); R1, R2 and R3 are each independently selected from C containing or not containing a type A heteroatom 6-30 Any one of the aromatic groups formed by the aromatic compound leaving any one of the H groups that can leave, the aromatic group optionally containing at least one substituent selected from the combination A; the L structural unit is C containing or not containing A type 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;

[0034] Mode 1: Position 10 of the A structural unit is directly bonded to the B structural unit or bonded through the L structural unit;

[0035] Mode 2: Any one or any two of the 11th position, 12th position, 13th position, 14th position, 21st position, 22nd position, 23rd position, and 24th position of the A structural unit are directly bonded to 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 the 10th position in formula (I-1) is substituted by phenyl, biphenyl, naphthyl, anthracenyl or phenanthryl; 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 Haloalkoxy, C with or without type A heteroatom 6-30 Aromatic group; the type A heteroatom includes at least one of N, O, and S.

[0036] According to a preferred embodiment 1, R1, R2 and R3 are each independently selected from C containing or not containing a type A heteroatom 6-24 Any one of the aromatic groups formed by the aromatic compound leaving any one of the H groups that can leave, the aromatic group optionally containing at least one substituent selected from the combination A; the L structural unit is C containing or not containing A type heteroatom 6-24At least one of the connecting groups formed by the aromatic compound leaving any two H capable of leaving, the connecting 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 or naphthyl; 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 Haloalkoxy, C with or without type A heteroatom 6-24 Aromatic group; the type A heteroatom includes at least one of N, O, and S.

[0037] According to a preferred embodiment 2, R1, R2 and R3 are each independently selected from 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, fluorenyl unsubstituted or substituted by at least one group in combination A, wherein the L structural unit is one or two of the connecting groups formed by the removal of any two Hs from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, and the connecting 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 or naphthyl; 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 Haloalkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

[0038] In the preferred embodiment 2, more preferably, the combination A contains C 1-3 Alkyl, C 1-3Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

[0039] According to a preferred embodiment 3, R1, R2 and R3 are each independently selected from 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, dibenzothiophene unsubstituted or substituted by at least one group in combination A, dibenzofuranyl unsubstituted or substituted by at least one group in combination A, substituted fluorenyl, unsubstituted or substituted carbazolyl, unsubstituted or substituted by at least one group in combination A naphtho[2,1-b]benzofuranyl; the L structural unit is one or two of the connecting groups formed by the removal of any two Hs capable of leaving from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, 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; in formula (I-1), X1 and X2 are each independently O or S; the combination A contains C 1-3 Alkyl, C 1-3 Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

[0040] In the preferred embodiment 3, more preferably, the organic compound is selected from any one of Compound 1 to Compound 72.

[0041] According to a preferred embodiment 4, R1, R2 and R3 are each independently selected from 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, fluorenyl unsubstituted or substituted by A carbazolyl group substituted with at least one group in combination A, a naphtho[2,1-b]benzofuranyl group which is unsubstituted or substituted with at least one group in combination A; the L structural unit is one or two of the connecting groups formed by the removal of any two H groups which can leave from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, 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 the mode 2; in formula (I-1), X1 and X2 are each independently O or S; the N at position 10 is substituted with phenyl, biphenyl or naphthyl; the combination A contains C 1-3 Alkyl, C 1-3 Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

[0042] In the preferred specific embodiment 4, more preferably, the connection method of the A structural unit and the B structural unit is the method 2, and any one or two of the 12th position and the 22nd position of the A structural unit are directly bonded to the B structural unit or bonded through the L structural unit.

[0043] In the preferred embodiment 4, it is particularly preferred that the organic compound is selected from any one of Compound 73 to Compound 164.

[0044] According to a preferred embodiment 5, the organic compound is selected from any one of the following:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050] 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.

[0051] As mentioned above, the second aspect of the present invention provides the use of the aforementioned organic compound containing a spiro structure in an organic electroluminescent device.

[0052] Preferably, the organic compound containing a spiro structure is present in at least one of a hole transport layer, a light emitting layer and an electron blocking layer of the organic electroluminescent device.

[0053] 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.

[0054] In the present invention, one of the first electrode and the second electrode is an anode, and the other is a cathode.

[0055] 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.

[0056] Particularly preferably, the present invention provides an organic electroluminescent device containing one or more of the organic compounds described in the first aspect, wherein the organic compound is present in at least one of the hole transport layer, the light-emitting layer and the electron blocking layer of the organic electroluminescent device.

[0057] 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;

[0058] At least one of the hole transport layer, the light emitting layer and the electron blocking layer of the organic electroluminescent device contains at least one of the aforementioned organic compounds containing a spiro structure.

[0059] Particularly preferably, the organic compound containing a spiro structure is present in the electron blocking layer of the organic electroluminescent device.

[0060] Preferably, the organic compound is used as an electron blocking material in an electron blocking layer of an organic electroluminescent device. The inventors of the present invention have found that when the compound of the present invention is used as a material in an electron blocking layer of an organic electroluminescent device, the driving voltage of the organic electroluminescent device can be significantly reduced and the luminous efficiency can be improved.

[0061] Preferably, 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 which are stacked in sequence.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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:

[0071] ,

[0072] 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.

[0073] According to some embodiments of the present invention, the electron blocking layer of the device contains the compound described in the first aspect of the present invention.

[0074] 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.

[0075] According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.

[0076] According to some embodiments of the present invention, the host material may include anthracene derivatives, carbazole derivatives, fluorene derivatives, aromatic amine derivatives, silicone derivatives, carbazole-triazine derivatives, and phosphorus-oxygen derivatives, but is not limited thereto.

[0077] In some preferred embodiments of the present invention, the anthracene derivative has the general formula shown below:

[0078]

[0079] The phosphorus-oxygen derivatives have the general formula shown below:

[0080]

[0081] In the general formulas of the anthracene derivatives and phosphorus-oxygen derivatives, R 11 , R 12 , R 13 , R 14 , R 15 and R 16Each 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.

[0082] 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.

[0083] 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.

[0084] In some preferred embodiments of the present invention, the sulfone derivative has the general formula shown below:

[0085]

[0086] The ketone derivatives have the general formula shown below:

[0087]

[0088] In the general formulas of the above-mentioned sulfone derivatives and ketone derivatives, R 20 , R 21 , R 22 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.

[0089] 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:

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] Intermediate Preparation Example 1

[0099]

[0100] 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%).

[0101] 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.

[0102] 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).

[0103] Intermediate Preparation Example 2

[0104]

[0105] Synthesis of intermediate A2: The synthesis method is the same as that of intermediate A1 to obtain intermediate A2 (yield: 55.4%).

[0106] 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).

[0107] Intermediate Preparation Example 3

[0108]

[0109] Synthesis of intermediate A3: The synthesis method is the same as that of intermediate A1 to obtain intermediate A3 (yield: 52.8%).

[0110] 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).

[0111] Intermediate Preparation Example 4

[0112]

[0113] 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%).

[0114] Synthesis of intermediate A4: The synthesis method is the same as that of intermediate A1 to obtain intermediate A4 (yield: 57.6%).

[0115] 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).

[0116] Intermediate Preparation Example 5

[0117]

[0118] Synthesis of intermediate A5: The synthesis method is the same as that of intermediate A1 to obtain intermediate A5 (yield: 55.6%).

[0119] 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).

[0120] Intermediate Preparation Example 6

[0121]

[0122] Synthesis of intermediate A6: The synthesis method is the same as that of intermediate A1 to obtain intermediate A6 (yield: 55.2%).

[0123] 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).

[0124] Preparation Example 1

[0125]

[0126] Synthesis of compound 4: In a 500ml three-necked flask, under nitrogen protection, intermediate A1 (50mmol), 4'-bromo-1,1',2',1''-terphenyl (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 56h. 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: 76.8%).

[0127] Mass spectrum: C47H29NO2, theoretical value: 639.22, measured value: 639.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.18~7.39 (8H, m), 7.40~7.53 (10H, m), 7.56~7.62 (2H, m), 7.75~7.82 (4H, m), 7.87~7.95 (3H, m), 8.16~8.22 (2H, m).

[0128] Preparation Example 2

[0129]

[0130] Synthesis of compound 13: The synthesis method was the same as that of compound 4 to obtain compound 13 (yield: 76.5%).

[0131] Mass spectrum: C51H31NO2, theoretical value: 689.24, measured value: 689.18. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.18~7.45 (12H, m), 7.45~7.55 (5H, m), 7.55~7.63 (3H, m), 7.72~7.83 (4H, m), 7.87~7.93 (2H, m), 8.04~8.10 (1H, m), 8.16~8.25 (3H, m), 8.48~8.54 (1H, m).

[0132] Preparation Example 3

[0133]

[0134] Synthesis of compound 28: The synthesis method was the same as that of compound 4 to obtain compound 28 (yield: 77.8%).

[0135] Mass spectrum: C47H28N2O2, theoretical value: 652.22, measured value: 652.30. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.01~7.29 (12H, m), 7.30~7.46 (4H, m), 7.47~7.55 (3H, m), 7.56~7.62 (2H, m), 7.87~7.93 (2H, m), 7.95~7.99 (1H, m), 8.14~8.24 (3H, m), 8.52~8.58 (1H, m).

[0136] Preparation Example 4

[0137]

[0138] Synthesis of compound 37: The synthesis method was the same as that of compound 4 to obtain compound 37 (yield: 76.3%).

[0139] Mass spectrum: C47H30N2O2, theoretical value: 654.23, measured value: 654.15. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.72~6.76 (2H, m), 6.82~6.84 (1H, m), 6.98~7.03 (2H, m), 7.06~7.10 (4H, m), 7.20~7.31 (11H, 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), 8.14~8.17 (2H, m).

[0140] Preparation Example 5

[0141]

[0142] Synthesis of compound 70: The synthesis method was the same as that of compound 4 to obtain compound 70 (yield: 75.8%).

[0143] Mass spectrum: C59H38N2S2, theoretical value: 838.25, measured value: 838.29. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.71~6.76 (2H, m), 6.80~6.84 (1H, m), 7.22~7.27 (3H, m), 7.28~7.43 (12H, m), 7.46~7.51 (4H, m), 7.53~7.58 (4H, m), 7.70~7.78 (6H, m), 7.84~7.92 (4H, m), 8.14~8.19 (2H, m).

[0144] Preparation Example 6

[0145]

[0146] Synthesis of intermediate 74-1: The synthesis method is the same as that of compound 4 to obtain intermediate 74-1 (yield: 78.4%).

[0147] Synthesis of compound 74: The synthesis method was the same as that of compound 4 to obtain compound 74 (yield: 76.2%).

[0148] Mass spectrum: C53H34N2O2, theoretical value: 730.26, measured value: 730.29. 1H-NMR (400MHz, CDCl3) (ppm) δ=6.96~7.11 (6H, m), 7.17~7.44 (14H, m), 7.46~7.62 (8H, m), 7.72~7.78 (3H, m), 7.84~7.93 (2H, m), 8.14~8.20 (1H, m).

[0149] Preparation Example 7

[0150]

[0151] Synthesis of intermediate 108-1: In a 500 ml three-necked flask, under nitrogen protection, 1,4-dioxane solvent (200 ml), N-(3-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (50 mmol), diboron pinacol ester (50 mmol), potassium acetate (125 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (0.5 mmol) were added in sequence under stirring, and the temperature was raised to reflux for reaction for 5 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 (250 ml) was added for slurrying, and the product was recrystallized from toluene / ethanol to obtain intermediate 108-1 (yield: 91.5%).

[0152] Synthesis of compound 108: In a 500 ml three-necked flask, under nitrogen protection, intermediate 74-1 (45 mmol), intermediate 108-1 (45 mmol), toluene (230 ml), dicyclohexyl (2', 4', 6'-triisopropyl-(1,1'-biphenyl)-2-yl) phosphonic acid (2.25 mmol), PD2(DBA)3 (tri(dibenzylideneacetone)dipalladium, 0.45 mmol), 40 ml of an aqueous solution containing potassium dihydrogen phosphate (112.5 mmol) were added, stirring was started and heated to 90 °C for overnight reaction. After 25 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, which 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 108 (yield: 88.3%).

[0153] Mass spectrum: C59H38N2O2, theoretical value: 806.29, measured value: 806.33. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.98~7.03 (2H, m), 7.06~7.11 (4H, m), 7.15~7.30 (12H, m), 7.32~7.43 (4H, m), 7.46~7.52 (4H, m), 7.53~7.61 (5H, m), 7.73~7.80 (3H, m), 7.88~7.92 (1H, m), 8.07~8.11 (1H, m), 8.18~8.21 (1H, m), 8.26~8.28 (1H, m).

[0154] Preparation Example 8

[0155]

[0156] Synthesis of intermediate 130-1: The synthesis method is the same as that of intermediate 108-1 to obtain intermediate 130-1 (yield: 90.3%).

[0157] Synthesis of intermediate 130-2: The synthesis method is the same as that of compound 4 to obtain intermediate 130-2 (yield: 77.6%).

[0158] Synthesis of Compound 130: The synthesis method was the same as that of Compound 108 to obtain Compound 130 (yield: 87.9%).

[0159] Mass spectrum: C62H42N2S2, theoretical value: 878.28, measured value: 878.22. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.67 ~ 1.70 (6H, s), 6.98 ~ 7.02 (2H, m), 7.06 ~ 7.10 (4H, m), 7.22 ~ 7.28 (7H, m), 7.30 ~ 7.48 (8H, m), 7.47~7.49 (1H, m), 7.51~7.57 (3H, m), 7.71~7.75 (2H, m), 7.76~7.80 (1H, m), 7.84~7.8 8 (3H, m), 7.88~7.92 (2H, m), 8.07~8.11 (1H, m), 8.20~8.23 (1H, m), 8.25~8.27 (1H, m).

[0160] Preparation Example 9

[0161]

[0162] Synthesis of compound 135: The synthesis method was the same as that of compound 4 to obtain compound 135 (yield: 75.9%).

[0163] Mass spectrum: C47H28N2S2, theoretical value: 684.17, measured value: 684.21. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.98~7.28 (10H, m), 7.29~7.43 (6H, m), 7.49~7.55 (1H, m), 7.69~7.77 (2H, m), 7.82~7.93 (3H, m), 8.01~8.12 (2H, m), 8.16~8.28 (2H, m), 8.37~8.41 (1H, m), 8.52~8.58 (1H, m).

[0164] Preparation Example 10

[0165]

[0166] Synthesis of intermediate 137-1: The synthesis method is the same as that of compound 4 to obtain intermediate 137-1 (yield: 78.7%).

[0167] Synthesis of compound 137: The synthesis method was the same as that of compound 4 to obtain compound 137 (yield: 73.8%).

[0168] Mass spectrum: C59H39N3O2, theoretical value: 821.30, measured value: 821.33. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.96~7.04 (5H, m), 7.05~7.11 (10H, m), 7.18~7.29 (14H, m), 7.31~7.37 (2H, m), 7.47~7.53 (2H, m), 7.56~7.62 (2H, m), 7.72~7.75 (2H, m), 7.84~7.88 (2H, m).

[0169] Preparation Example 11

[0170]

[0171] Synthesis of intermediate 160-1: The synthesis method is the same as that of compound 4 to obtain intermediate 160-1 (yield: 77.4%).

[0172] Synthesis of Compound 160: The synthesis method was the same as that of Compound 4 to obtain Compound 160 (yield: 73.5%).

[0173] Mass spectrum: C83H51N3O2S2, theoretical value: 1185.34, measured value: 1185.33. 1H-NMR (400MHz, CDCl3) (ppm) δ = 6.42~6.44 (1H, m), 6.45~6.47 (1H, m), 6.96~7.11 (3H, m), 7.20~7.28 (2H, m), 7.29~7.44 (16H, m), 7.45~7.50 (3H, m), 7.51~7.58 (9H, m), 7.70~7.78 (6H, m), 7.83~7.89 (6H, m), 7.95~8.01 (2H, m), 8.02~8.04 (2H, m).

[0174] Device Example 1

[0175] 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;

[0176] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10 -4 Pa, vacuum evaporate HAT-CN as a hole injection layer on the above anode layer film, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 5nm; then evaporate the hole transport layer NPB, the evaporation rate is 0.1nm / s, and the thickness is 60nm; vacuum evaporate compound 4 as an electron blocking layer on the hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 10nm;

[0177] 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 GH is adjusted to 0.1nm / 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 30nm.

[0178] 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.

[0179] 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.

[0180] Device Examples 2-12

[0181] Organic light-emitting devices of device examples 2 to 12 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.

[0182] The molecular structures involved are as follows:

[0183] .

[0184] Device Comparison Example 1-2

[0185] 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.

[0186]

[0187] Test Example 1

[0188] At brightness 10000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1-12 and device comparative examples 1-2 were measured. The results are shown in Table 1.

[0189] Table 1

[0190]

[0191] 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.

[0192] 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. An organic compound containing a spiro structure, 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); the B structural unit is selected from any one of -R1 and -N(R2)(R3); R1, R2 and R3 are each independently selected from 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 The present invention comprises a phenanthryl group substituted with at least one group in combination A, a dibenzothiophene group unsubstituted or substituted with at least one group in combination A, a dibenzofuran group unsubstituted or substituted with at least one group in combination A, a fluorenyl group unsubstituted or substituted with at least one group in combination A, a carbazolyl group unsubstituted or substituted with at least one group in combination A, and a naphtho[2,1-b]benzofuranyl group unsubstituted or substituted with at least one group in combination A; the L structural unit is one or two of the linking groups formed by the departure of any two H capable of leaving from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene; 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: Position 10 of the A structural unit is directly bonded to the B structural unit or bonded through the L structural unit; Mode 2: Any one or two of the 12th and 22nd positions of the A structural unit are directly bonded to 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 a phenyl group, a biphenyl group or a naphthyl group; 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 Haloalkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

2. The organic compound according to claim 1, characterized in that The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

3. The organic compound according to claim 1 or 2, characterized in that R1, R2 and R3 are each independently selected from 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, fluorenyl unsubstituted or substituted by at least one group in combination A, carbazolyl unsubstituted or substituted by at least one group in combination A, naphtho[2,1-b]benzofuranyl unsubstituted or substituted by at least one group in combination A; The L structural unit is one or two of the linking groups formed by the removal of any two H's 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 the combination A; The connection method of the A structural unit and the B structural unit is the method 1; In formula (I-1), X1 and X2 are each independently O or S; The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

4. The organic compound according to claim 3, characterized in that The organic compound is selected from any one of the following: 。 5. The organic compound according to claim 1 or 2, characterized in that R1, R2 and R3 are each independently selected from 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, fluorenyl unsubstituted or substituted by at least one group in combination A, carbazolyl unsubstituted or substituted by at least one group in combination A, naphtho[2,1-b]benzofuranyl unsubstituted or substituted by at least one group in combination A; The L structural unit is one or two of the linking groups formed by the removal of any two H's 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 the combination A; The connection method of the A structural unit and the B structural unit is the method 2; In formula (I-1), X1 and X2 are each independently O or S; N at position 10 is substituted by phenyl, biphenyl or naphthyl; The combination A contains C 1-3 Alkyl, C 1-3 Alkoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzothienyl, dibenzofuranyl, fluorenyl, carbazolyl, naphtho[2,1-b]benzofuranyl.

6. The organic compound according to claim 5, characterized in that The connection method of the A structural unit and the B structural unit is the method 2, and any one or two of the 12th and 22nd positions of the A structural unit are directly bonded to the B structural unit or bonded through the L structural unit.

7. The organic compound according to claim 6, characterized in that The organic compound is selected from any one of the following: 。 8. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from any one of the following: 。 9. Use of the organic compound containing a spiro structure according to any one of claims 1 to 8 in an organic electroluminescent device; And / or, the organic compound containing a spiro structure is present in at least one of a hole transport layer, a light emitting layer and an electron blocking layer of the organic electroluminescent device.

10. 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 transport layer, the light emitting layer and the electron blocking layer of the organic electroluminescent device contains at least one of the organic compounds containing a spiro structure according to any one of claims 1 to 8.

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