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

Abstract

The present invention relates to the field of organic electroluminescent devices, and in particular to an organic compound containing a condensed ring and its application, and an organic electroluminescent device. The organic compound has a structure shown by A-L-B, and A is a group shown by formula (I-1), B is a group formed by the compound shown by formula (I-2) leaving any H that can leave; 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 Hs that can leave, and the linking group optionally contains at least one substituent selected from combination A. The parent core structure of the compound of the present invention has good planarity, can improve electron mobility, and can be applied to organic electroluminescent devices to improve the efficiency of the device.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent devices, and in particular to an organic compound containing a condensed ring and an 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] In organic electroluminescent devices, the hole transfer rate in the hole layer is 2-3 orders of magnitude higher than the electron transfer rate in the electron layer, so that the recombination of electrons and holes cannot be completely located in the light-emitting layer. The holes will migrate toward the electron layer, and the excess holes will overflow into the electron layer, causing leakage, which further affects the efficiency and life of the device.

[0006] Therefore, it is of great practical significance to develop high-performance hole blocking layer materials and improve the luminous efficiency and service life of devices. Summary of the invention

[0007] The purpose of the present invention is to overcome the defects of the prior art OLED devices or screens, such as high driving voltage and low current efficiency.

[0008] In order to achieve the above object, the present invention provides an organic compound containing a fused ring, wherein the organic compound has a structure shown in ALB, and A is a group shown in formula (I-1), B is a group formed by removing any H that can leave from the compound shown in formula (I-2); L does not exist 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;

[0009]

[0010] in,

[0011] In formula (I-2), X 1 C or Si;

[0012] R 1 and R 2 Each independently selected from H, 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 3-30 At least one of the aromatic groups, or R 1 and R 2 Cyclize together to form C 6-30 An aromatic group; and the aromatic group optionally contains at least one substituent selected from combination A;

[0013] n R 3 and m R 4 Each independently selected from C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C 1-20 haloalkoxy; or any two adjacent R 3 and / or any two adjacent R 4 Cyclize together to form C 6-30 Aromatic group; n and m are each independently an integer of 0-4;

[0014] 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;

[0015] The type A heteroatom includes at least one of N, O, and S.

[0016] The second aspect of the present invention provides use of the aforementioned condensed ring-containing organic compound in an organic electroluminescent device.

[0017] 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;

[0018] 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 containing condensed rings.

[0019] The present invention has at least the following specific advantages:

[0020] The compound of the present invention has an adjustable HOMO which can reach below 6.0 eV, can well block the migration of holes, and can improve the efficiency of the device.

[0021] The parent core structure of the compound of the present invention has good planarity, can improve electron mobility, and can improve the efficiency of the device when applied to an organic electroluminescent 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 leaves two or more of the linking groups formed by any two H atoms that can leave. For example, naphthalene and benzene both leave two H atoms, and the two atoms are bonded to each other to form a linking group.

[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] “n and m are each independently an integer of 0-4”, when n or m is 0, it means that H is connected to the C at that position.

[0033] As mentioned above, the first aspect of the present invention provides an organic compound containing a fused ring, the organic compound having a structure shown in ALB, wherein A is a group shown in formula (I-1), B is a group formed by removing any H that can leave from the compound 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;

[0034]

[0035] in,

[0036] In formula (I-2), X 1 C or Si;

[0037] R 1 and R 2 Each independently selected from H, 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 3-30 At least one of the aromatic groups, or R 1 and R 2 Cyclize together to form C 6-30 An aromatic group; and the aromatic group optionally contains at least one substituent selected from combination A;

[0038] n R 3 and m R4 Each independently selected from C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C 1-20 haloalkoxy; or any two adjacent R 3 and / or any two adjacent R 4 Cyclize together to form C 6-30 Aromatic group; n and m are each independently an integer of 0-4;

[0039] 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;

[0040] The type A heteroatom includes at least one of N, O, and S.

[0041] 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;

[0042] In formula (I-2), X 1 C or Si;

[0043] R 1 and R 2 Each independently selected from H, 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 3-24 At least one of the aromatic groups, or R 1 and R 2 Cyclize together to form C 6-24 An aromatic group; and the aromatic group optionally contains at least one substituent selected from combination A;

[0044] n R 3 and m R 4 Each independently selected from C 1-12 Alkyl, C 1-12 Alkoxy, C substituted by at least one halogen 1-12 Haloalkyl, C 1-12haloalkoxy; or any two adjacent R 3 and / or any two adjacent R 4 Cyclize together to form C 6-24 Aromatic group; n and m are each independently an integer of 0-4;

[0045] 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;

[0046] The type A heteroatom includes at least one of N, O, and S.

[0047] 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;

[0048] In formula (I-2), X 1 C or Si;

[0049] R 1 and R 2 Each independently selected from H, C 1-12 at least one of alkyl, phenyl unsubstituted or substituted with at least one group in combination A, biphenyl unsubstituted or substituted with at least one group in combination A, naphthyl unsubstituted or substituted with at least one group in combination A, anthracenyl unsubstituted or substituted with at least one group in combination A, phenanthryl unsubstituted or substituted with at least one group in combination A, dibenzothiophenyl unsubstituted or substituted with at least one group in combination A, dibenzofuranyl unsubstituted or substituted with at least one group in combination A, and fluorenyl unsubstituted or substituted with at least one group in combination A, or R 1 and R 2 Cyclize together to form C 6-24 An aromatic group; and the aromatic group optionally contains at least one substituent selected from combination A;

[0050] n R 3 and m R 4 Each independently selected from C 1-6 Alkyl; or any two adjacent R 3 and / or any two adjacent R 4 Cyclize together to form C 6-24 An aromatic group; n and m are each independently 0, 1 or 2;

[0051] The combination A contains C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Halogenated alkyl.

[0052] 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;

[0053] In formula (I-2), X 1 C or Si;

[0054] R 1 and R 2 each independently selected from at least one of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl unsubstituted or substituted by at least one group in combination A, biphenyl unsubstituted or substituted by at least one group in combination A, naphthyl unsubstituted or substituted by at least one group in combination A, anthracenyl unsubstituted or substituted by at least one group in combination A, phenanthryl unsubstituted or substituted by at least one group in combination A, dibenzothiophenyl unsubstituted or substituted by at least one group in combination A, dibenzofuranyl unsubstituted or substituted by at least one group in combination A, and fluorenyl unsubstituted or substituted by at least one group in combination A, or R 1 and R 2 Cyclize together to form C 6-24 An aromatic group; and the aromatic group optionally contains at least one substituent selected from combination A;

[0055] n R 3 and m R 4 Each independently selected from C 1-6 Alkyl; or any two adjacent R 3 and / or any two adjacent R 4 Cyclize together to form C 6-24 An aromatic group; n and m are each independently 0, 1 or 2;

[0056] 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.

[0057] According to a preferred embodiment 4, the organic compound is selected from any one of the following:

[0058]

[0059]

[0060]

[0061]

[0062] 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.

[0063] As mentioned above, the second aspect of the present invention provides the use of the aforementioned condensed ring-containing organic compound in an organic electroluminescent device.

[0064] Preferably, the condensed ring-containing organic compound is present in at least one of a hole blocking layer, a light-emitting layer and an electron transport layer of the organic electroluminescent device.

[0065] Particularly preferably, the organic compound is present in a hole-blocking layer of the organic electroluminescent device.

[0066] 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;

[0067] 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 containing condensed rings.

[0068] Preferably, the condensed ring-containing organic compound exists in a hole blocking layer of the organic electroluminescent device.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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:

[0074] ,

[0075] 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.

[0076] 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:

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.

[0082] 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.

[0083] In some preferred embodiments of the present invention, the anthracene derivative has the general formula shown below:

[0084]

[0085] The phosphorus-oxygen derivatives have the general formula shown below:

[0086]

[0087] 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.

[0088] 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.

[0089] 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.

[0090] In some preferred embodiments of the present invention, the sulfone derivative has the general formula shown below:

[0091]

[0092] The ketone derivatives have the general formula shown below:

[0093]

[0094] 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.

[0095] According to some embodiments of the present invention, the hole blocking layer is selected from the compounds described in the present invention.

[0096] According to some embodiments of the present invention, 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.

[0097] 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 to.

[0098] 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.

[0099] 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.

[0100] Unless otherwise specified, the room temperature mentioned below means 25±1°C.

[0101] Preparation Example 1: Synthesis of Compound 7

[0102]

[0103] Synthesis of intermediate 7-1: 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 7-1 was obtained by column chromatography (yield: 67%).

[0104] Synthesis of intermediate 7-2: 0.06 mol of intermediate 7-1 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 7-2 was obtained by column chromatography (yield: 81%).

[0105] Synthesis of intermediate 7-3: 0.04 mol of intermediate 7-2 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 7-3 was obtained by column chromatography (yield: 75%).

[0106] Synthesis of intermediate 7-4: 0.03 mol of intermediate 7-3 was dissolved in 100 ml of 1,4-dioxane solvent, stirred under nitrogen, and 0.03 mol of pinacol diboron, 0.06 mol of potassium acetate, and 0.09 mmol of ferrocene palladium dichloride were added in sequence. 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 7-4 (yield: 76%).

[0107] Synthesis of compound 7: 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 7-4, 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 7 (yield: 78%).

[0108] Mass spectrum: C46H28N2O, theoretical value: 624.22, measured value: 741.26. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.22~7.29 (4H, m), 7.31~7.35 (1H, 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 (2H, m).

[0109] Preparation Example 2: Synthesis of Compound 10

[0110]

[0111] Synthesis of intermediate 10-1: The synthesis method is the same as that of intermediate 7-1 to obtain intermediate 10-1 (yield: 68%).

[0112] Synthesis of intermediate 10-2: The synthesis method is the same as that of intermediate 7-2 to obtain intermediate 10-2 (yield: 78%).

[0113] Synthesis of intermediate 10-3: The synthesis method is the same as that of intermediate 7-3 to obtain intermediate 10-3 (yield: 77%).

[0114] Synthesis of intermediate 10-4: The synthesis method is the same as that of intermediate 7-4 to obtain intermediate 10-4 (yield: 76%).

[0115] Synthesis of compound 10: The synthesis method was the same as that of compound 7 to obtain compound 10 (yield: 78%).

[0116] Mass spectrum: C36H24N2O, theoretical value: 500.19, measured value: 500.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.67~1.71 (6H, s), 7.22~7.26 (1H, m), 7.32~7.36 (1H, m), 7.39~7.43 (1H, m), 7.60~7.70 (6H, m), 7.76~7.80 (1H, m), 7.88~7.91 (1H, m), 8.07~8.13 (3H, m), 8.17~8.20 (1H, m), 8.24~8.26 (1H, d), 8.96~9.00 (2H, m).

[0117] Preparation Example 3: Synthesis of Compound 13

[0118]

[0119] Synthesis of intermediate 13-1: The synthesis method is the same as that of intermediate 7-1 to obtain intermediate 13-1 (yield: 69%).

[0120] Synthesis of intermediate 13-2: The synthesis method is the same as that of intermediate 7-2 to obtain intermediate 13-2 (yield: 80%).

[0121] Synthesis of intermediate 13-3: The synthesis method is the same as that of intermediate 7-3 to obtain intermediate 13-3 (yield: 79%).

[0122] Synthesis of intermediate 13-4: The synthesis method is the same as that of intermediate 7-4 to obtain intermediate 13-4 (yield: 75%).

[0123] Synthesis of compound 13: The synthesis method was the same as that of compound 7 to obtain compound 13 (yield: 77%).

[0124] Mass spectrum: C36H24N2O, theoretical value: 500.19, measured value: 500.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.06~7.13 (2H, m), 7.14~7.30 (5H, m), 7.31~7.39 (2H, m), 7.40~7.44 (1H, m), 7.52~7.73 (6H, m), 7.86~7.94 (2H, m), 8.08~8.14 (2H, m), 8.16~8.23 (2H, m), 8.94~9.01 (2H, m).

[0125] Preparation Example 4: Synthesis of Compound 20

[0126]

[0127] Synthesis of compound 20: The synthesis method was the same as that of compound 7 to obtain compound 20 (yield: 80%).

[0128] Mass spectrum: C36H24N2O, theoretical value: 500.19, measured value: 500.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.67~1.71 (6H, s), 7.20~7.28 (1H, m), 7.31~7.38 (1H, m), 7.57~7.62 (2H, m), 7.64~7.72 (3H, m), 7.76~7.80 (1H, m), 7.88~7.92 (1H, d), 8.00~8.02 (2H, m), 8.06~8.14 (4H, m), 8.17~8.21 (1H, d), 8.95~9.00 (2H, m).

[0129] Preparation Example 5: Synthesis of Compound 30

[0130]

[0131] Synthesis of compound 30: The synthesis method was the same as that of compound 7 to obtain compound 30 (yield: 79%).

[0132] Mass spectrum: C45H28N2OS, theoretical value: 640.20, measured value: 640.21. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.06~7.15 (6H, m), 7.14~7.29 (5H, m), 7.31~7.39 (2H, m), 7.40~7.44 (1H, m), 7.52~7.73 (6H, m), 7.86~7.94 (2H, m), 8.08~8.14 (2H, m), 8.16~8.22 (2H, m), 8.94~9.01 (2H, m).

[0133] Preparation Example 6: Synthesis of Compound 34

[0134]

[0135] Synthesis of intermediate 34-1: The synthesis method is the same as that of compound 7 to obtain intermediate 34-1 (yield: 79%).

[0136] Synthesis of compound 34: The synthesis method was the same as that of compound 7 to obtain compound 34 (yield: 77%).

[0137] Mass spectrum: C42H28N2O, theoretical value: 576.22, measured value: 576.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.67~1.71 (6H, s), 7.20~7.28 (5H, m), 7.31~7.38 (1H, m), 7.56~7.62 (2H, m), 7.63~7.72 (3H, m), 7.76~7.80 (1H, m), 7.88~7.92 (1H, m), 8.00~8.03 (2H, m), 8.07~8.13 (3H, m), 8.17~8.21 (1H, m), 8.39~8.43 (1H, d), 8.96~9.00 (2H, m).

[0138] Preparation Example 7: Synthesis of Compound 44

[0139]

[0140] Synthesis of intermediate 44-1: The synthesis method is the same as that of compound 7 to obtain intermediate 44-1 (yield: 77%).

[0141] Synthesis of compound 44: The synthesis method was the same as that of compound 7 to obtain compound 44 (yield: 76%).

[0142] Mass spectrum: C56H34N2O, theoretical value: 750.27, measured value: 750.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.20~7.26 (5H, m), 7.29~7.40 (3H, m), 7.52~7.56 (1H, m), 7.61~7.80 (10H, m), 7.81~7.83 (1H, m), 7.86~7.93 (3H, m), 7.96~8.03 (2H, m), 8.06~8.14 (3H, m), 8.16~8.22 (2H, m), 8.95~9.01 (4H, m).

[0143] Preparation Example 8: Synthesis of Compound 49

[0144]

[0145] Synthesis of intermediate 49-1: The synthesis method is the same as that of intermediate 7-1 to obtain intermediate 49-1 (yield: 68%).

[0146] Synthesis of intermediate 49-2: The synthesis method is the same as that of intermediate 7-2 to obtain intermediate 49-2 (yield: 81%).

[0147] Synthesis of intermediate 49-3: The synthesis method is the same as that of intermediate 7-3 to obtain intermediate 49-3 (yield: 77%).

[0148] Synthesis of intermediate 49-4: The synthesis method is the same as that of intermediate 7-4 to obtain intermediate 49-4 (yield: 76%).

[0149] Synthesis of compound 49: The synthesis method was the same as that of compound 7 to obtain compound 49 (yield: 79%).

[0150] Mass spectrum: C40H24N2O, theoretical value: 548.19, measured value: 548.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.06~7.39 (10H, m), 7.40~7.45 (1H, d), 7.52~7.73 (5H, m), 7.85~7.94 (2H, m), 8.07~8.22 (4H, m), 8.92~9.04 (2H, m).

[0151] Preparation Example 9: Synthesis of Compound 56

[0152]

[0153] Synthesis of Compound 56: The synthesis method was the same as that of Compound 7 to obtain Compound 56 (yield: 81%).

[0154] Mass spectrum: C36H24N2O, theoretical value: 500.19, measured value: 500.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.67~1.71 (6H, s), 7.22~7.26 (1H, m), 7.32~7.36 (1H, m), 7.57~7.64 (3H, m), 7.66~7.70 (2H, m), 7.75~7.79 (2H, m), 7.89~7.91 (1H, m), 8.00~8.04 (2H, m), 8.08~8.13 (3H, m), 8.18~8.20 (1H, m), 8.96~9.00 (2H, m).

[0155] Preparation Example 10: Synthesis of Compound 60

[0156]

[0157] Synthesis of compound 60: The synthesis method was the same as that of compound 7 to obtain compound 60 (yield: 78%).

[0158] Mass spectrum: C41H26N2O, theoretical value: 562.20, measured value: 562.21. 1H-NMR (400MHz, CDCl3) (ppm) δ=2.26~2.30 (3H, s), 7.18~7.30 (6H, m), 7.30~7.38 (1H, m), 7.58~7.72 (5H, m), 7.74~7.80 (2H, m), 7.87~7.93 (1H, m), 8.00~8.06 (2H, m), 8.07~8.14 (3H, m), 8.16~8.22 (1H, m), 8.95~9.01 (2H, m).

[0159] Preparation Example 11: Synthesis of Compound 65

[0160]

[0161] Synthesis of compound 65: The synthesis method was the same as that of compound 7 to obtain compound 65 (yield: 77%).

[0162] Mass spectrum: C46H28N2O, theoretical value: 624.22, measured value: 624.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 7.10~7.13 (2H, m), 7.14~7.30 (6H, m), 7.31~7.39 (2H, m), 7.40~7.44 (4H, m), 7.52~7.73 (6H, m), 7.86~7.94 (2H, m), 8.08~8.14 (2H, m), 8.16~8.23 (2H, m), 8.96~9.02 (2H, m).

[0163] Preparation Example 12: Synthesis of Compound 69

[0164]

[0165] Synthesis of intermediate 69-1: The synthesis method is the same as that of compound 7 to obtain intermediate 69-1 (yield: 78%).

[0166] Synthesis of compound 69: The synthesis method was the same as that of compound 7 to obtain compound 69 (yield: 75%).

[0167] Mass spectrum: C42H28N2O, theoretical value: 576.22, measured value: 576.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.67~1.71 (6H, s), 7.22~7.26 (1H, m), 7.32~7.36 (1H, m), 7.56~7.64 (5H, m), 7.66~7.72 (3H, m), 7.74~7.79 (2H, m), 7.89~7.91 (1H, m), 8.00~8.05 (2H, m), 8.07~8.13 (4H, m), 8.17~8.20 (1H, m), 8.96~9.00 (2H, m).

[0168] Preparation Example 13: Synthesis of Compound 82

[0169]

[0170] Synthesis of intermediate 82-1: The synthesis method is the same as that of compound 7 to obtain intermediate 82-1 (yield: 77%).

[0171] Synthesis of intermediate 82-2: The synthesis method is the same as that of intermediate 7-4 to obtain intermediate 82-2 (yield: 79%).

[0172] Synthesis of Compound 82: The synthesis method was the same as that of Compound 7 to obtain Compound 82 (yield: 80%).

[0173] Mass spectrum: C58H32N2O2, theoretical value: 788.25, measured value: 788.23. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.20~7.27 (5H, m), 7.29~7.42 (3H, m), 7.52~7.56 (1H, m), 7.59~7.80 (10H, m), 7.81~7.83 (1H, m), 7.86~7.93 (3H, m), 7.96~8.03 (2H, m), 8.06~8.14 (3H, m), 8.16~8.22 (2H, m), 8.95~9.01 (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 TCTA 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 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 at 7% of the evaporation rate of the main material, and the total evaporation film thickness is 30nm;

[0178] Compound 7 was vacuum-deposited on the light-emitting layer as the hole blocking layer of the device, with a deposition rate of 0.1 nm / s and a thickness of 5 nm. Then, the electron transport layer was evaporated, and the deposition rates of ET-1 and ET-2 were adjusted to 0.1 nm / s by using a multi-source co-evaporation method, and the total deposition film thickness was 30 nm.

[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 to 13

[0181] Organic light-emitting devices of device examples 2 to 13 were prepared by a method similar to that of device example 1, except that compound 7 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 Examples 1~3

[0185] Organic electroluminescent devices of Comparative Examples 1 to 3 were prepared by a method similar to that of Device Example 1, except that Compound 7 in Device Example 1 was replaced by Ref-1, Ref-2, and Ref-3, 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 embodiments 1 to 13 and device comparative examples 1 to 3 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 condensed ring, characterized in that: The organic compound has a structure represented by ALB, wherein A is a group represented by formula (I-1), B is a group formed by removing any one H that can leave from the compound represented by formula (I-2); L does not exist or L is at least one of the linking groups formed by removing any two H that can leave from benzene, biphenyl, naphthalene, anthracene, phenanthrene, dibenzothiophene, dibenzofuran or fluorene, and the linking group optionally contains at least one substituent selected from combination A; in, In formula (I-2), X1 is C or Si; R1 and R2 are each independently selected from H, C 1-20 Alkyl, C 1-20 Alkoxy, C substituted by at least one halogen 1-20 Haloalkyl, C 1-20 at least one of a halogenated alkoxy group, a phenyl group which is unsubstituted or substituted with at least one group in combination A, a biphenyl group which is unsubstituted or substituted with at least one group in combination A, a naphthyl group which is unsubstituted or substituted with at least one group in combination A, an anthracenyl group which is unsubstituted or substituted with at least one group in combination A, and a phenanthryl group which is unsubstituted or substituted with at least one group in combination A, or R1 and R2 are cyclized together to form C 6-30 Aromatic groups; n R3 and m R4 are each independently selected from C 1-6 Alkyl; n and m are each independently an integer of 0-4; 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 Halogenated alkoxy.

2. The condensed ring-containing organic compound according to claim 1, characterized in that: R1 and R2 are each independently selected from H, C 1-12 Alkyl, C 1-12 Alkoxy, C substituted by at least one halogen 1-12 Haloalkyl, C 1-12 at least one of a halogenated alkoxy group, a phenyl group which is unsubstituted or substituted with at least one group in combination A, a biphenyl group which is unsubstituted or substituted with at least one group in combination A, a naphthyl group which is unsubstituted or substituted with at least one group in combination A, an anthracenyl group which is unsubstituted or substituted with at least one group in combination A, and a phenanthryl group which is unsubstituted or substituted with at least one group in combination A, or R1 and R2 are cyclized together to form C 6-30 Aromatic groups; 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 Halogenated alkoxy.

3. The condensed ring-containing organic compound according to claim 2, characterized in that: R1 and R2 are each independently selected from H, C 1-12 at least one of alkyl, 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, and phenanthryl unsubstituted or substituted by at least one group in combination A, or R1 and R2 are cyclized together to form C 6-30 Aromatic groups; n R3 and m R4 are each independently selected from C 1-6 Alkyl; n and m are each independently 0, 1 or 2; The combination A contains C 1-6 Alkyl, C 1-6 Alkoxy, C substituted by at least one halogen 1-6 Halogenated alkyl.

4. The condensed ring-containing organic compound according to claim 3, characterized in that: R1 and R2 are each independently selected from at least one of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 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, and phenanthryl unsubstituted or substituted by at least one group in combination A, or R1 and R2 are cyclized together to form C 6-30 Aromatic groups; 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.

5. An organic compound containing a condensed ring, characterized in that: The organic compound is selected from any one of the following: 。 6. Use of the condensed ring-containing organic compound according to any one of claims 1 to 5 in an organic electroluminescent device; The condensed ring-containing organic compound exists in the hole blocking layer of the organic electroluminescent device.

7. 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 hole blocking layer of the organic electroluminescent device contains at least one of the condensed ring-containing organic compounds according to any one of claims 1 to 5.

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