An organic compound and its application, an organic electroluminescent device

Abstract

The present invention relates to the field of organic electroluminescent devices, and discloses an organic compound and its application, and an organic electroluminescent device. The organic compound has a structure shown by A-L-B, wherein A is a group shown by formula (I-1), B is a group shown by formula (I-2), L does not exist or L is a C containing or not containing A-type heteroatoms. 3‑30 The aromatic compound leaves at least one of the linking groups formed by any two H atoms that can leave, and the linking group optionally contains at least one substituent selected from the group A. The organic compound of the present invention is applied to an organic electroluminescent device to reduce the driving voltage, improve the luminous efficiency and service life.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent devices, and in particular to an organic compound and application thereof, and an organic electroluminescent device. Background Art

[0002] The phenomenon of organic electroluminescence was first discovered by Pope et al. in 1963. They found that a single-layer crystal of anthracene could emit a faint blue light when driven by a voltage of more than 100 V. However, the driving voltage was high and the thickness of the single-crystalline anthracene was large, so it did not attract widespread attention.

[0003] It was not until 1987 that Dr. Qingyun Deng and others from Kodak reported that they had prepared a sandwich-type OLED device by vacuum thermal evaporation based on two organic semiconductor materials: 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport properties, and aromatic diamine with good hole transport properties. The external quantum efficiency reached 1% at a driving voltage of less than 10V, making organic electroluminescent materials and devices practical. This has greatly promoted the research on OLED materials and devices. With the continuous development of OLED technology, the performance of OLED devices has also been widely concerned. During the research process, it was found that a high-efficiency, long-life, and excellent-performance device requires excellent device materials and a combination of device layers.

[0004] 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, luminescent materials, electron transport materials, electron injection materials, etc.

[0005] Among them, electron transport materials play a vital role in the driving voltage and luminous efficiency of the device. In order to obtain high-performance electron transport materials, the material is required to have high electron mobility to improve the luminous efficiency and service life of the device.

[0006] Therefore, it is of great practical significance to develop high-performance electron transport materials to reduce the driving voltage of the device and improve the luminous efficiency of the device. Summary of the invention

[0007] The purpose of the present invention is to overcome the defects of the existing organic electroluminescent devices, such as high driving voltage and low luminous efficiency.

[0008] In order to achieve the above object, the present invention provides an organic compound having a structure shown in ALB, wherein A is a group shown in formula (I-1), B is a group shown in formula (I-2), L is absent or L is a C containing or not containing A type heteroatom. 3-30The aromatic compound leaves at least one of the linking groups formed by any two H capable of leaving, and the linking group optionally contains at least one substituent selected from the group A;

[0009]

[0010] in,

[0011] In formula (I-2), X 1 and X 2 are each independently N or CH; R 1 and R 2 Each independently selected from C containing or not containing A type heteroatom 3-30 At least one of the aromatic groups, and the aromatic group optionally contains at least one substituent selected from the group A;

[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;

[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 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 organic compounds.

[0017] The organic compound of the invention is applied to an organic electroluminescent device, which can reduce the driving voltage and improve the luminous efficiency and service life.

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

[0019] 1. The new compound formed by the mother core structure and the electron-withdrawing groups 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 be applied to OLED devices to reduce the driving voltage;

[0020] 2. The compound provided by the present invention has good planarity and high electron mobility, that is, strong electron transmission ability. The compound of the present invention is applied to organic electroluminescent devices to improve the luminous efficiency of the devices;

[0021] 3. The compound of the present invention has a relatively high glass transition temperature, which makes the thermal stability of the film good, thereby increasing the service life of the device. DETAILED DESCRIPTION

[0022] 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.

[0023] 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.

[0024] "Halogen" means fluorine, chlorine, bromine or iodine.

[0025] 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".

[0026] "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 removes two or more of the linking groups formed by any two H atoms that can leave. For example, in compound 37 of the present invention, naphthalene and benzene both remove two H atoms and bond to each other to form a linking group.

[0027] In the group represented by formula (I-1), the dotted line indicates that the site capable of connecting with other groups may be any site, for example, at least one of the 1st, 2nd, 3rd and 4th positions.

[0028] “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.

[0029] "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.

[0030] “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.

[0031] "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.

[0032] "Naphtho[2,1-b]benzofuranyl" means a radical formed by the removal of any leaving H from the compound shown below:

[0033] .

[0034] As mentioned above, the first aspect of the present invention provides an organic compound having a structure shown in ALB, wherein A is a group shown in formula (I-1), B is a group shown in formula (I-2), L is absent or L is a C containing or not containing a hetero atom of type A. 3-30 The aromatic compound leaves at least one of the linking groups formed by any two H capable of leaving, and the linking group optionally contains at least one substituent selected from the group A;

[0035]

[0036] in,

[0037] In formula (I-2), X 1 and X 2 are each independently N or CH; R 1 and R 2 Each independently selected from C containing or not containing A type heteroatom 3-30 At least one of the aromatic groups, and the aromatic group optionally contains at least one substituent selected from the group A;

[0038] 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;

[0039] The type A heteroatom includes at least one of N, O, and S.

[0040] According to a preferred embodiment 1, the optional L is a C containing or not containing A type heteroatom 3-24 The aromatic compound leaves any two H capable of leaving to form one or two of the connecting groups, the connecting group optionally containing at least one substituent selected from combination A;

[0041] In formula (I-2), X 1 and X 2 are each independently N or CH; R 1 and R 2 Each independently selected from C containing or not containing A type heteroatom 3-24 At least one of the aromatic groups, and the aromatic group optionally contains at least one substituent selected from the group A;

[0042] The combination A contains C 1-12 Alkyl, C 1-12 Alkoxy, C substituted by at least one halogen1-12 Haloalkyl, C 1-12 Haloalkoxy;

[0043] The type A heteroatom includes at least one of N, O, and S.

[0044] According to a preferred embodiment 2, the optional L is one or two of the linking groups formed by the removal of any two H capable of leaving from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, and the linking group optionally contains at least one substituent selected from combination A;

[0045] In formula (I-2), X 1 and X 2 are each independently N or CH; R 1 and R 2 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, pyridyl unsubstituted or substituted by at least one group in combination A, and naphtho[2,1-b]benzofuranyl unsubstituted or substituted by at least one group in combination A;

[0046] The combination A contains C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Halogenated alkyl.

[0047] According to a preferred embodiment 3, the optional L is one or two of the linking groups formed by the removal of any two H capable of leaving from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, and the linking group optionally contains at least one substituent selected from combination A;

[0048] In formula (I-2), X 1 and X 2 are each independently N or CH; R 1 and R 2each 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, pyridyl unsubstituted or substituted by at least one group in combination A, and naphtho[2,1-b]benzofuranyl unsubstituted or substituted by at least one group in combination A;

[0049] The combination A contains methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, and trichloromethyl.

[0050] According to a preferred embodiment 4, the organic compound is selected from any one of the following:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] .

[0064] 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.

[0065] As mentioned above, the second aspect of the present invention provides the use of the aforementioned organic compound in an organic electroluminescent device.

[0066] Preferably, the organic compound is present in an electron transport layer of the organic electroluminescent device.

[0067] Preferably, the 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.

[0068] According to a preferred 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 the organic compound of the present invention.

[0069] According to one embodiment of the present specification, the organic material layer of the organic electroluminescent device of the present specification can also form a multilayer structure of two or more organic material layers. The organic electroluminescent device of the present invention includes 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, and a charge generation layer between the organic light-emitting layers. However, the structure of the organic device is not limited thereto, and may include fewer or more organic layer materials.

[0070] 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;

[0071] 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 organic compounds.

[0072] Preferably, the organic compound is present in the electron transport layer of the organic electroluminescent device.

[0073] The organic compound is particularly preferred as an electron transport material in an electron transport layer of the organic electroluminescent device.

[0074] According to one embodiment of the present invention, the organic electroluminescent device of the present invention further comprises a first covering layer and / or a second covering layer, wherein the first covering layer is arranged on the outer surface of the anode, and the second covering layer is arranged on the outer surface of the cathode.

[0075] 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 organic compound provided by the present invention is applied by vapor deposition at an initial pressure of 1.5 Pa.

[0076] Further preferably, when preparing the organic electroluminescent device of the present invention, the organic compound of the present invention or other compounds are first fully mixed, and then applied in the above manner to form one or more layers. More preferably, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The compounds are applied by vapor deposition at an initial pressure of 1.3 Pa to form one or more layers.

[0077] The organic electroluminescent device of the invention is preferably coated with one or more layers by an organic vapor deposition method or by means of carrier gas sublimation. -6 The material 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 and forms a device structure.

[0078] The organic electroluminescent device of the present invention is preferably formed into a single-layer or multi-layer structure by light-induced thermal imaging or thermal transfer.

[0079] The organic electroluminescent device of the present invention preferably prepares the organic 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, and more preferably inkjet printing. However, 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 a solution, the solvent in the solution will destroy the already formed layer, which is not conducive to device production. The organic compound provided by the present invention can be replaced by structural modification, so that the organic compound of the present invention undergoes cross-linking under heating or ultraviolet exposure, thereby maintaining a complete layer without being destroyed. The organic compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in a polymer network.

[0080] Preferably, the organic electroluminescent device of the invention is produced by applying one or more layers from solution and by applying one or more layers by a sublimation method.

[0081] 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. According to some embodiments of the present invention, the material forming the hole injection layer has the ability to transport holes. Therefore, 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.

[0082] 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.

[0083] 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, dibenzoindenofluoreneamine, and spirobifluoreneamine, but are not limited thereto. According to some embodiments of the present invention, the hole injection layer and the hole transport layer can be formed, for example, using aromatic amine derivatives of the following general formula:

[0084] .

[0085] 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.

[0086] 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:

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.

[0092] 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, phosphorus-oxygen derivatives, and phenanthroline derivatives, but is not limited thereto.

[0093] In some preferred embodiments of the present invention, the anthracene derivative has the general formula shown below:

[0094]

[0095] The phosphorus-oxygen derivatives have the general formula shown below:

[0096]

[0097] In the general formulas of the anthracene derivatives and phosphorus-oxygen derivatives, R 11 , R 12 , R 13 , R 14 , R 15 and R 16 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.

[0098] According to some embodiments of the present invention, the guest material is preferably a compound that generates 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. According to some embodiments of the present invention, the guest material in the light-emitting layer may include perylene derivatives, anthracene derivatives, fluorene derivatives, distyryl aromatic derivatives, aromatic amine derivatives, organosilicon derivatives, organoboron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone derivatives, sulfone derivatives, cyano derivatives and xanthene derivatives, but is not limited thereto.

[0099] In some preferred embodiments of the present invention, the sulfone derivative has the general formula shown below:

[0100]

[0101] The ketone derivatives have the general formula shown below:

[0102]

[0103] In the general formulas of the above-mentioned sulfone derivatives and ketone derivatives, R 20 , R 21 , R 22 and R 23Each 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.

[0104] 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:

[0105] 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.

[0106] 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.

[0107] 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, and benzimidazole derivatives, but is not limited thereto.

[0108] According to some preferred embodiments of the present invention, the electron transport layer is selected from the organic compounds described in the present invention.

[0109] 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. Materials for the electron injection layer include, for example, LiF, CsF, Cs 2 CO 3 , LiQ, but not limited thereto. According to some embodiments of the present invention, the cathode material is preferably 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.

[0110] 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.

[0111] Unless otherwise specified, the room temperature mentioned below means 25±1°C.

[0112] Preparation Example 1: Synthesis of Compound 4

[0113]

[0114] Synthesis of intermediate 4-1: 0.1 mol of raw material a was dissolved in 340 ml of toluene, and 0.1 mol of raw material b, 0.25 mol of sodium tert-butoxide, 0.003 mol of tris(dibenzylideneacetone)dipalladium, and 0.003 mol of tri-tert-butylphosphine were added. The mixture was stirred under nitrogen and heated to reflux. After 4 hours, the reaction of the raw materials was detected to be complete. The reaction solution was decompressed and dried, and intermediate 4-1 was obtained by column chromatography (yield: 67%).

[0115] Synthesis of intermediate 4-2: 0.06 mol of intermediate 4-1 was dissolved in 260 ml of dichloromethane, cooled to 0°C, 0.07 mol of boron tribromide was added, and stirred at 0°C for 24 h. After the reaction was completed, sodium bicarbonate aqueous solution was added to quench, and then extracted with dichloromethane three times. After drying over anhydrous magnesium sulfate, the reaction solution was decompressed and dried, and intermediate 4-2 was obtained by column chromatography (yield: 81%).

[0116] Synthesis of intermediate 4-3: 0.04 mol of intermediate 4-2 was dissolved in 170 ml of toluene, and 0.04 mol of iodobenzene, 0.05 mol of sodium tert-butoxide, 0.0012 mol of tri-tert-butylphosphine, and 0.0012 mol of tris(dibenzylideneacetone)dipalladium were added in sequence under nitrogen protection, and the mixture was stirred and heated to reflux for reaction. After 2 hours, the reaction of the raw materials was detected to be complete, the reaction solution was decompressed and dried, and intermediate 4-3 was obtained by column chromatography (yield: 75%).

[0117] Synthesis of intermediate 4-4: 0.03 mol of intermediate 4-3 was dissolved in 100 ml of 1,4-dioxane solvent, stirred under nitrogen, 0.03 mol of pinacol diboron, 0.06 mol of potassium acetate, and 0.09 mmol of ferrocene palladium dichloride were added in sequence, and the temperature was raised to reflux for reaction. After 2 h, HPLC detected that the reaction of the raw materials was basically completed, and the reaction was stopped. The reaction solution was decompressed and dried, and the residue was subjected to column chromatography to obtain intermediate 4-4 (yield: 76%).

[0118] Synthesis of compound 4: 0.01 mol of raw material c was dissolved in 440 ml of toluene solvent, nitrogen was introduced with stirring, 0.01 mol of intermediate 4-4, 0.02 mol of potassium carbonate, and 0.3 mmol of tetrakis(triphenylphosphine)palladium were added in sequence, the temperature was raised to reflux, and after 2 h, HPLC detected that the raw material was basically reacted completely, the reaction was stopped, the temperature was lowered and filtered to obtain a crude product, which was completely soluble in toluene. The filtrate was decompressed and dried, and the residue was subjected to column chromatography to obtain compound 4 (yield: 78%).

[0119] Mass spectrum: C36H21N5O, theoretical value: 539.17, measured value: 539.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.38~7.43 (1H, m), 7.46~7.54 (6H, m), 7.59~7.71 (4H, m), 8.08~8.13 (2H, m), 8.17~8.21 (1H, m), 8.32~8.40 (4H, m), 8.64~8.68 (1H, m), 8.95~9.01 (2H, m).

[0120] Preparation Example 2: Synthesis of Compound 6

[0121]

[0122] Synthesis of compound 6: The synthesis method is the same as that of compound 4 to obtain compound 6 (yield: 74%)

[0123] Mass spectrum: C49H30N5O, theoretical value: 690.24, measured value: 690.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.36~7.54 (7H, m), 7.58~7.78 (8H, m), 7.82~7.88 (4H, m), 8.08~8.14 (2H, m), 8.16~8.24 (2H, m), 8.26~8.34 (4H, m), 8.63~8.69 (1H, m), 8.95~9.01 (2H, m).

[0124] Preparation Example 3: Synthesis of Compound 56

[0125]

[0126] Synthesis of intermediate 56-1: The synthesis method is the same as that of intermediate 4-1 to obtain intermediate 56-1 (yield: 68%).

[0127] Synthesis of intermediate 56-2: The synthesis method is the same as that of intermediate 4-2 to obtain intermediate 56-2 (yield: 78%).

[0128] Synthesis of intermediate 56-3: The synthesis method is the same as that of intermediate 4-3 to obtain intermediate 56-3 (yield: 77%).

[0129] Synthesis of intermediate 56-4: The synthesis method is the same as that of intermediate 4-4 to obtain intermediate 56-4 (yield: 76%).

[0130] Synthesis of Compound 56: The synthesis method was the same as that of Compound 4 to obtain Compound 56 (yield: 78%).

[0131] Mass spectrum: C36H21N5O, theoretical value: 539.17, measured value: 539.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.56 (6H, m), 7.57~7.73 (4H, m), 7.99~8.03 (1H, m), 8.07~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.44 (5H, m), 8.95~9.01 (2H, m).

[0132] Preparation Example 4: Synthesis of Compound 59

[0133]

[0134] Synthesis of compound 59: The synthesis method was the same as that of compound 4 to obtain compound 59 (yield: 80%).

[0135] Mass spectrum: C48H29N5O, theoretical value: 691.24, measured value: 691.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.21~7.29 (4H, m), 7.36~7.54 (6H, m), 7.57~7.79 (8H, m), 7.91~8.03 (5H, m), 8.08~8.14 (2H, m), 8.16~8.22 (1H, m), 8.38~8.44 (1H, d), 8.94~9.01 (2H, m).

[0136] Preparation Example 5: Synthesis of Compound 61

[0137]

[0138] Synthesis of intermediate 61-1: The synthesis method is the same as that of compound 4 to obtain intermediate 61-1 (yield: 77%).

[0139] Synthesis of compound 61: The synthesis method was the same as that of compound 4 to obtain compound 61 (yield: 79%).

[0140] Mass spectrum: C49H30N4O, theoretical value: 690.24, measured value: 690.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.36~7.51 (6H, m), 7.56~7.72 (8H, m), 7.73~7.85 (4H, m), 7.91~8.03 (5H, m), 8.07~8.14 (2H, m), 8.16~8.25 (2H, m), 8.38~8.44 (1H, d), 8.94~9.01 (2H, m).

[0141] Preparation Example 6: Synthesis of Compound 66

[0142]

[0143] Synthesis of intermediate 66-1: The synthesis method is the same as that of compound 4 to obtain intermediate 66-1 (yield: 78%).

[0144] Synthesis of Compound 66: The synthesis method was the same as that of Compound 4 to obtain Compound 66 (yield: 80%).

[0145] Mass spectrum: C48H25N5OS, theoretical value: 751.15, measured value: 751.16. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.26~7.36 (2H, m), 7.51~7.73 (8H, m), 7.82~7.90 (2H, m), 7.95~8.04 (3H, m), 8.08~8.14 (2H, m), 8.16~8.22 (1H, m), 8.38~8.49 (3H, m), 8.77~8.83 (2H, d), 8.94~9.02 (2H, m).

[0146] Preparation Example 7: Synthesis of Compound 76

[0147]

[0148] Synthesis of intermediate 76-1: The synthesis method is the same as that of compound 4 to obtain intermediate 76-1 (yield: 79%).

[0149] Synthesis of Compound 76: The synthesis method was the same as that of Compound 4 to obtain Compound 76 (yield: 78%).

[0150] Mass spectrum: C42H25N5O, theoretical value: 615.21, measured value: 615.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.54 (6H, m), 7.57~7.74 (6H, m), 7.99~8.03 (1H, d), 8.08~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.45 (7H, m), 8.94~9.02 (2H, m).

[0151] Preparation Example 8: Synthesis of Compound 81

[0152]

[0153] Synthesis of intermediate 81-1: The synthesis method is the same as that of compound 4 to obtain intermediate 81-1 (yield: 76%).

[0154] Synthesis of Compound 81: The synthesis method was the same as that of Compound 4 to obtain Compound 81 (yield: 78%).

[0155] Mass spectrum: C46H27N5O, theoretical value: 665.22, measured value: 665.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.30~7.44 (2H, m), 7.46~7.58 (7H, m), 7.59~7.72 (4H, m), 7.75~7.81 (1H, d), 8.00~8.03 (1H, d), 8.08~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.44 (5H, m), 8.92~9.05 (4H, m).

[0156] Preparation Example 9: Synthesis of Compound 93

[0157]

[0158] Synthesis of Compound 93: The synthesis method was the same as that of Compound 4 to obtain Compound 93 (yield: 81%).

[0159] Mass spectrum: C42H25N5O, theoretical value: 615.21, measured value: 615.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.21~7.29 (2H, m), 7.36~7.54 (6H, m), 7.57~7.79 (6H, m), 7.92~8.04 (3H, m), 8.07~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.44 (3H, m), 8.94~9.02 (2H, m).

[0160] Preparation Example 10: Synthesis of Compound 99

[0161]

[0162] Synthesis of intermediate 99-1: The synthesis method is the same as that of intermediate 4-1 to obtain intermediate 99-1 (yield: 67%).

[0163] Synthesis of intermediate 99-2: The synthesis method is the same as that of intermediate 4-2 to obtain intermediate 99-2 (yield: 77%).

[0164] Synthesis of intermediate 99-3: The synthesis method is the same as that of intermediate 4-3 to obtain intermediate 99-3 (yield: 79%).

[0165] Synthesis of intermediate 99-4: The synthesis method is the same as that of intermediate 4-4 to obtain intermediate 99-4 (yield: 78%).

[0166] Synthesis of compound 99: The synthesis method was the same as that of compound 4 to obtain compound 99 (yield: 78%).

[0167] Mass spectrum: C37H22N4O, theoretical value: 538.18, measured value: 538.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.72 (10H, m), 7.73~7.79 (1H, d), 7.90~7.98 (4H, m), 7.99~8.03 (1H, d), 8.07~8.14 (2H, m), 8.16~8.25 (2H, m), 8.94~9.02 (2H, m).

[0168] Preparation Example 11: Synthesis of Compound 104

[0169]

[0170] Synthesis of Compound 104: The synthesis method was the same as that of Compound 4 to obtain Compound 104 (yield: 80%).

[0171] Mass spectrum: C48H29N5O, theoretical value: 691.24, measured value: 691.25. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.36~7.54 (6H, m), 7.57~7.81 (13H, m), 7.99~8.03 (1H, d), 8.08~8.14 (2H, m), 8.16~8.22 (1H, m), 8.34~8.44 (4H, m), 8.94~9.02 (2H, m).

[0172] Preparation Example 12: Synthesis of Compound 107

[0173]

[0174] Synthesis of Compound 107: The synthesis method was the same as that of Compound 4 to obtain Compound 107 (yield: 77%).

[0175] Mass spectrum: C44H25N5O, theoretical value: 639.21, measured value: 639.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.52~7.72 (8H, m), 7.73~7.79 (1H, m), 7.95~8.22 (10H, m), 8.45~8.53 (2H, m), 8.94~9.01 (2H, m), 9.06~9.12 (2H, m).

[0176] Preparation Example 13: Synthesis of Compound 118

[0177]

[0178] Synthesis of Compound 118: The synthesis method was the same as that of Compound 4 to obtain Compound 118 (yield: 76%).

[0179] Mass spectrum: C42H25N5O, theoretical value: 615.21, measured value: 615.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.55 (6H, m), 7.57~7.79 (7H, m), 7.99~8.03 (1H, d), 8.07~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.41 (5H, m), 8.49~8.53 (1H, m), 8.95~9.01 (2H, m).

[0180] Preparation Example 14: Synthesis of Compound 123

[0181]

[0182] Synthesis of intermediate 123-1: The synthesis method is the same as that of compound 4 to obtain intermediate 123-1 (yield: 79%).

[0183] Synthesis of compound 123: The synthesis method was the same as that of compound 4 to obtain compound 123 (yield: 78%).

[0184] Mass spectrum: C46H27N5O, theoretical value: 665.22, measured value: 665.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.30~7.44 (2H, m), 7.46~7.58 (7H, m), 7.58~7.72 (4H, m), 7.73~7.81 (2H, m), 7.99~8.03 (1H, d), 8.07~8.14 (2H, m), 8.16~8.22 (1H, m), 8.31~8.41 (4H, m), 8.92~9.05 (4H, m).

[0185] Preparation Example 15: Synthesis of Compound 131

[0186]

[0187] Synthesis of intermediate 131-1: The synthesis method is the same as that of compound 4 to obtain intermediate 131-1 (yield: 78%).

[0188] Synthesis of intermediate 131-2: The synthesis method is the same as that of compound 4 to obtain intermediate 131-2 (yield: 80%).

[0189] Synthesis of compound 131: The synthesis method was the same as that of compound 4 to obtain compound 131 (yield: 78%).

[0190] Mass spectrum: C52H31N5O, theoretical value: 741.25, measured value: 741.26. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.22~7.29 (4H, m), 7.31~7.35 (2H, s), 7.46~7.54 (6H, m), 7.59~7.71 (4H, m), 7.74~7.78 (1H, d), 7.94~7.98 (2H, d), 8.00~8.03 (1H, d), 8.09~8.13 (2H, m), 8.17~8.21 (1H, m), 8.33~8.39 (4H, m), 8.95~9.03 (4H, m).

[0191] Device Example 1

[0192] 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;

[0193] 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 TCTA as an electron blocking layer on the hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 10nm;

[0194] The light-emitting layer of the device is vacuum-evaporated on the hole transport layer. The light-emitting layer includes a host material and a guest material. The evaporation rate of the host material DIC-TRZ is adjusted to 0.1nm / s by using a multi-source co-evaporation method. The guest material Ir(ppy) 3 The evaporation rate is set to 10% of the evaporation rate of the main material, and the total evaporation film thickness is 30nm;

[0195] The electron transport layer of the device was vacuum-deposited on the light-emitting layer. The evaporation rates of ET-1 and compound 4 were adjusted to 0.1 nm / s by using a multi-source co-evaporation method, and the total evaporation film thickness was 30 nm.

[0196] 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.

[0197] Device Examples 2 to 15

[0198] Organic light-emitting devices of device examples 2 to 15 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.

[0199] The molecular structures involved are as follows:

[0200] .

[0201] Device Comparison Examples 1 to 3

[0202] Organic electroluminescent devices of Comparative Examples 1 to 3 were prepared by a method similar to that of Device Example 1, except that Compound 4 in Device Example 1 was replaced by Ref-1, Ref-2, and Ref-3, respectively.

[0203] .

[0204] Test Example 1

[0205] At brightness 10000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1-15 and device comparative examples 1-3 were measured. The results are shown in Table 1.

[0206] Table 1

[0207]

[0208] It can be seen from the experimental results shown in Table 1 that the organic electroluminescent device containing the compound of the present invention has a lower driving voltage and a higher luminous efficiency. Therefore, the compound of the present invention has better photoelectric performance when applied to the organic electroluminescent device.

[0209] 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, characterized in that The organic compound has a structure represented by ALB, and A is a group represented by formula (I-1), B is a group represented by formula (I-2), L does not exist or L is one or two of the linking groups formed by the removal of any two H capable of leaving 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, In formula (I-2), X1 and X2 are each independently N or CH; R1 and R2 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, pyridyl 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 combination A is C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Halogenated alkyl.

2. The organic compound according to claim 1, characterized in that The combination A is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, and trichloromethyl.

3. The organic compound according to claim 1 or 2, characterized in that The organic compound is selected from any one of the following:

4. Use of the organic compound according to any one of claims 1 to 3 in an organic electroluminescent device; The organic compound is present in the electron transport layer of the organic electroluminescent device.

5. 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; The electron transport layer of the organic electroluminescent device contains at least one of the organic compounds described in any one of claims 1 to 3.

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