Organic compound, organic electroluminescent element and electronic equipment
By using organic compounds of specific structures as the luminescent auxiliary layer material in organic electroluminescent devices, the problem of insufficient device stability and lifetime in the prior art is solved, and an organic electroluminescent device with high efficiency and long life is achieved.
Patent Information
- Application Number
- CN202311602030.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2023-11-28
- Publication Date
- 2025-05-30
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
While existing organic electroluminescent devices improve luminous efficiency and color saturation, it is difficult to ensure the stability and life of the device at the same time.
A new organic compound is adopted, which has a specific structure for use as a luminescent auxiliary layer material, to improve hole mobility and transport performance by introducing aryl-substituted phenylene groups, thereby improving luminescence efficiency and device life.
It significantly improves the luminous efficiency and life of organic electroluminescent devices, improves the stability of the device, and achieves the goal of high performance.
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Figure CN120058534A_ABST
Abstract
Description
Technical Field
[0001] The present invention belongs to the technical field of organic electroluminescence, and more specifically, relates to an organic compound, an organic electroluminescent element, and an electronic device. Background Art
[0002] An organic light emitting diode is a self-luminous display device based on organic electroluminescent materials. Different from existing liquid crystal display devices, it has the characteristics of not requiring a backlight source and being thin, and is a technology suitable for flexible device devices (flexible light emitting display devices).
[0003] Organic electroluminescent materials are polymer or small molecule organic materials that can emit light under the action of an electric field. In order to improve the stability and efficiency of the organic electroluminescent materials in an organic electroluminescent device, multiple layers of organic thin films are prepared between the anode and the cathode. The above-mentioned organic thin film layers can be divided into a hole injection layer, a hole transport layer, a light-emitting layer host, a light-emitting layer dopant, an electron transport layer, and an electron injection layer.
[0004] Based on the light-emitting materials (blue, green, and red three-color light materials) used in the above-mentioned light-emitting layer, a display device with high color saturation is prepared. According to the latest technical reports, white light for large-size displays is achieved by mixing a blue light-emitting material and a yellow light-emitting material or an orange light-emitting material, and blue light-emitting materials, green light-emitting materials, and red light-emitting materials are used in small-size displays.
[0005] When an electric field is applied between the anode and the cathode of an organic electroluminescent device, holes are injected from the anode, and the injected holes move to the light-emitting layer through the hole transport layer. At the same time, electrons are injected from the cathode, and the injected electrons move to the light-emitting layer through the electron transport layer. The holes and electrons that move to the light-emitting layer combine to form excitons. When the excitons transition from the excited state to the ground state, energy is released in the form of light, realizing the light emission of the device.
[0006] The efficiency of an organic electroluminescent device can generally be divided into internal luminescence efficiency and external luminescence efficiency. The internal luminescence efficiency is related to the light conversion efficiency of generating excitons in the organic layer (such as the hole transport layer, the light-emitting layer, and the electron transport layer, etc.) between the first electrode (for example, the anode) and the second electrode (for example, the cathode). In the theoretical values of the above-mentioned light conversion efficiency, fluorescence is 25% and phosphorescence is 75%. The external luminescence efficiency is related to the light extraction efficiency of the light generated in the organic layer being emitted to the outside of the organic electroluminescent device. Generally, the external light extraction efficiency is about 20% of the internal luminescence efficiency.
[0007] In order to ensure high efficiency and high color saturation, factors such as 1) energy levels and 2) electron movement of the peripheral functional layers related to the light-emitting layer should be considered. It is most important to improve the exciton generation efficiency in the light-emitting layer by adjusting the movement of holes and electrons injected from the electrodes. In addition to improving the exciton generation efficiency, in order to prevent excitons from transferring to the adjacent layers, the energy level of the lowest unoccupied molecular orbital (LUMO) of the hole transport layer is higher than that of the light-emitting layer, or the energy level of the highest occupied molecular orbital (HOMO) of the electron transport layer is lower than that of the light-emitting layer. Recently, it has been clarified that the triplet energy levels of the peripheral functional layers also affect the light-emitting efficiency. In order to fabricate organic electroluminescent devices with high efficiency and long lifetime, materials with high triplet energy levels and high lowest unoccupied molecular orbital (LUMO) energy levels are required. Summary of the Invention
[0008] In view of the above-mentioned defects or improvement requirements of the prior art, the present invention provides an organic compound, which can be used as a high-performance light-emitting auxiliary layer material, and can significantly improve the device performance when used in an organic electroluminescent device.
[0009] The technical solution adopted by the present invention to solve its technical problems is: an organic compound having the structure shown in formula (1),
[0010]
[0011] wherein, R 1 and R 2 are the same or different, and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heteroalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
[0012] L 1 and L 2 any one of them is selected from phenyl-substituted C6-C30 arylene, and the other is selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
[0013] Ar 1 is selected from substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
[0014] A is a divalent ethyl group, n is 0 or 1, and when n is 0, A and the bonds on both sides thereof do not exist;
[0015] When the substituent in the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl;
[0016] In the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl, the heteroatoms are each independently at least one of N, O, S, Si, and P.
[0017] Specifically, the divalent ethyl group is preferably -CH 2 -CH 2 -.
[0018] Furthermore, in an alternative embodiment of the present invention, the organic compound has the structure shown in formula (2) or formula (3),
[0019]
[0020] In formula (2) and formula (3), L 1 , L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
[0021] R 1 , R 2 are the same or different and are each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 heterocycloalkyl, a substituted or unsubstituted C3-C10 cycloalkenyl, a substituted or unsubstituted C3-C10 heterocycloalkenyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
[0022] Ar 1 is selected from a substituted or unsubstituted C3-C10 cycloalkenyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl;
[0023] A is a divalent ethyl group, n is 0 or 1, and when n is 0, A and the bonds on both sides thereof do not exist;
[0024] When the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl.
[0025] In the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl, the heteroatoms are each independently at least one of N, O, S, Si, and P.
[0026] Further, in an alternative embodiment of the present invention, the organic compound has the structure shown in formula (4) or formula (11).
[0027]
[0028] wherein L 1 and L 2、 R 1 and R 2、 Ar 1 are defined in the same manner as L 1 and L 2、 R 1 and R 2、 Ar 1 in the above formula (2) or (3).
[0029] Further, in an alternative embodiment of the present invention, the Ar 1 is selected from the following groups:
[0030]
[0031]
[0032] Further, in an alternative embodiment of the present invention, the L 1 and L 2 are the same or different and are each independently selected from a single bond, phenylene, phenyl-substituted phenylene, biphenylene, naphthylene, anthracene, phenanthrene, fluoranthene, pyrene, perylene, fluoranthene, terphenyl, phenylbiphenyl, dibenzofuran, dibenzothiophene, carbazole, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorene.
[0033] Further, in an alternative embodiment of the present invention, R 1 and R 2Same or different, each independently selected from hydrogen, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, phenylbiphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, and any one of combinations of two or more of the above groups.
[0034] The present invention also provides a preparation, which contains at least one of the above-mentioned organic compounds and at least one solvent.
[0035] The present invention also provides an organic electroluminescent device, comprising:
[0036] A first electrode;
[0037] A second electrode arranged to face the first electrode; and
[0038] One or more organic material layers arranged between the first electrode and the second electrode and including a light-emitting layer,
[0039] Wherein one or more of the organic material layers contain the organic compound of the present invention.
[0040] Specifically, in an embodiment of the present invention, a hole transport layer is included between the first electrode and the light-emitting layer, and a light-emitting auxiliary layer is included between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer contains the arylamine compound of the present invention.
[0041] The present invention also provides an electronic device, which includes a display device and a lighting device, and is provided with the above-mentioned organic electroluminescent device.
[0042] Generally speaking, compared with the prior art by the above technical solutions conceived by the present invention, the following beneficial effects can be achieved:
[0043] 1. For the organic compound of the present invention, by introducing an aryl-substituted phenylene into the triarylamine containing hydropyrene to increase the intermolecular distance, the hole mobility is improved, the hole transport performance is improved, and further the light-emitting efficiency of the device is improved. In addition, the stability of the thin film is particularly increased to improve the device life. The organic light-emitting device prepared from the organic compound of the present invention has good improvements in light-emitting efficiency and life. Description of the Drawings
[0044] Figure 1 It is a schematic diagram of the device structure of an organic electroluminescent device according to an embodiment of the present invention, wherein, the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the light-emitting auxiliary layer 4, the light-emitting layer 5, the electron transport layer 6, the electron injection layer 7, and the second electrode layer 8 Detailed Embodiments
[0045] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein like reference numerals always refer to like elements. In this regard, the exemplary embodiments may have different forms and should not be construed as limited to the description set forth herein. Accordingly, the exemplary embodiments are described below only by referring to the drawings for purposes of illustration. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. The phrase "at least one (s)" as used before or after a list of elements modifies the entire list of elements and not individual elements of the list.
[0046] It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.
[0047] It will be further understood that the terms "comprises" or "comprising," when used in this specification, specify the presence of the stated features, regions, wholes, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or groups thereof.
[0048] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.
[0049] As used herein, "about" or "approximately" includes the stated value and means within an acceptable deviation range for a particular value as determined by one of ordinary skill in the art in view of the measurements discussed and the error associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviation ranges of the stated value, or within the ranges of ±30%, 20%, 10%, 5%.
[0050] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, departures from the shape of the figures as a result, for example, of manufacturing techniques and / or tolerances are to be expected. Accordingly, the embodiments described herein should not be construed as limited to the specific shapes of regions as illustrated herein but include deviations in shape that result, for example, from manufacturing. For example, regions illustrated or described as flat may typically have rough and / or non-linear features. In addition, sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the exact shape of the regions and are not intended to limit the scope of the claims.
[0051] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the protection scope of the present invention. In addition, it should be understood that after reading the content disclosed in the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the protection scope defined by the present invention.
[0052] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; unless otherwise specified, the reagents, materials, etc. used in the following examples can all be obtained from commercial channels.
[0053] Term Explanation
[0054] As used in the present invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.
[0055] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 10 carbon atoms, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.
[0056] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, etc.
[0057] As used in the present invention, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic group having 2 to 10 carbon atoms, and at least one heteroatom is included in the ring, and the heteroatom is selected from O, S, N, P, Si.
[0058] As used in the present invention, the term "alkoxy" refers to a straight-chain, branched-chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited herein, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, benzyloxy.
[0059] As used in the present invention, the term "cycloalkenyl" refers to an unsaturated carbocyclic ring and does not have aromaticity.
[0060] As used in the present invention, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring and does not have aromaticity.
[0061] As used in the present invention, the term "aryl having 6 to 60 carbon atoms" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl group may have a form in which two or more of the rings are simply linked to each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.
[0062] As used in the present invention, the term "arylene" refers to a divalent aryl group derived by removing one hydrogen atom from an "aryl" group. For example, removing one hydrogen atom from a phenyl group forms a phenylene group, and removing one hydrogen atom from a naphthyl group forms a naphthylene group.
[0063] As used in the present invention, the term "heteroaryl having 3 to 60 carbon atoms" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1-3 carbons, in the ring is replaced by a heteroatom such as N, O, S, P, B or Si. Further, such a heteroaryl group may have a form in which two or more of the rings are simply linked to each other or fused to each other or fused to an aryl group. Examples of such heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furyl, thienyl, benzofuryl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuryl, dibenzothienyl, etc., and the present invention is not limited thereto.
[0064] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl group derived by removing one hydrogen atom from a "heteroaryl" group. For example, removing one hydrogen atom from a pyridyl group forms a pyridylene group.
[0065] As used in the present invention, the term "silyl group" refers to a trisubstituted silyl group, such as trimethylsilyl group, triphenylsilyl group, etc.
[0066] As used in the present invention, in the expression "Z group having X - Y carbon atoms" or "Z group of C(X - Y)", "having X - Y carbon atoms" means the number of carbon atoms of the Z group when it is unsubstituted, excluding the carbon atoms of the substituents when substitution occurs. For example, an aryl group of C6 - C60 means that when unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60, that is, when unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20... 60.
[0067] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where substitution occurs can be the position where the hydrogen atom is replaced. That is, this position is not limited to a specific position as long as the hydrogen at this position can be replaced by a substituent. For example, the carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto,
[0068]
[0069] indicating the substitution position. "Unsubstituted" means retaining a hydrogen atom, and in this case, the hydrogen atom includes protium, deuterium, and tritium.
[0070] When there are two or more substituents, the two or more substituents can be the same or different.
[0071] As used in the present invention, the term "terphenyl" includes
[0072] As used in the present invention, the hydrogen atom includes protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms from natural sources, or deuterium atoms can be introduced by deuterating a part or all of the starting compounds. If deuterium atoms are introduced from the starting materials, the deuteration rate can be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate can also be 1% or more, or 5% or more, or 10% or more. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and non - deuterated compounds, or a mixture of fully deuterated compounds and incompletely deuterated compounds, or a mixture of fully deuterated compounds, non - deuterated compounds, and incompletely deuterated compounds.
[0073] As used in the present invention, terms such as "first", "second", "A", "B" etc. are used. These terms are only used to distinguish the components and do not limit the nature or order of the components corresponding to the terms.
[0074] Organic electroluminescent element
[0075] The structure used in the organic electroluminescent element of the present invention is a publicly known structure, including an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound of the present invention.
[0076] The organic layer may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.
[0077] The light-emitting element of the present invention can be fluorescent light emission, phosphorescent light emission, or a combination thereof. The light-emitting element can be a single light emission or a series type of multiple light-emitting units.
[0078] As a simple light-emitting element, the following can be cited, but are not limited thereto.
[0079] (1) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer;
[0080] (2) Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer;
[0081] (3) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer;
[0082] (4) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer;
[0083] (5) Hole transport layer / Fluorescent light-emitting layer / Spacer layer / Phosphorescent light-emitting layer / Electron transport layer;
[0084] (6) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer;
[0085] (7) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer;
[0086] (8) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Electron transport layer;
[0087] (9) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Hole blocking layer / Electron transport layer;
[0088] (10) Hole injection layer / Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer / Electron injection layer;
[0089] (11) Hole injection layer / hole transport layer / fluorescent emitting layer / electron transport layer / electron injection layer;
[0090] (12) Hole injection layer / hole transport layer / electron blocking layer / phosphorescent emitting layer / electron transport layer / electron injection layer;
[0091] (13) Hole injection layer / hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer / electron injection layer;
[0092] The above-mentioned phosphorescent / fluorescent emitting layers can each emit light of different colors.
[0093] As a tandem organic electroluminescent device, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can generally also be referred to as a charge generation layer, an electron extraction layer, a connection layer, etc. For example, when stacking a fluorescent emitting layer and a phosphorescent emitting layer, in order to prevent the excitons generated in the phosphorescent emitting layer from diffusing to the fluorescent emitting layer or to adjust the carrier balance, an intermediate layer is placed between the fluorescent emitting layer and the phosphorescent emitting layer.
[0094] When the organic light-emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.
[0095] The organic electroluminescent device of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers are formed by using the compound of formula (1).
[0096] As a cathode material, a material with a low work function is usually used to facilitate electron injection into the organic material layer.
[0097] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes.
[0098] The hole transport material is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. Appropriately, the hole transport material can be a material with a high hole mobility that receives holes from the anode or the hole injection layer and transfers the holes to the light-emitting layer.
[0099] The light-emitting material can be a material that respectively receives holes and electrons from the hole transport layer and the electron transport layer and combines the holes and electrons to emit light in the visible light region. The light-emitting layer material includes a host material and a dopant material.
[0100] The electron transport material is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material can be a material with a high electron mobility that receives electrons from the cathode and transfers the electrons to the light-emitting layer.
[0101] The electron injection layer is a layer that injects electrons from the electrode.
[0102] The hole blocking layer is a layer that blocks holes from reaching the cathode.
[0103] The electron blocking layer is a layer that blocks electrons from reaching the anode.
[0104] Depending on the materials used, the organic light-emitting device of this specification can be a top-emitting device, a bottom-emitting device, or a dual-emission device.
[0105] The charge generation layer refers to the intermediate layer between the anode and the cathode in a tandem-structured device, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and efficiently transport charge carriers.
[0106] The core of the present invention is to provide an organic compound having the structure shown in Formula (2) or Formula (3).
[0107]
[0108] In Formula (2) and Formula (3), L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group.
[0109] R 1 and R 2 are the same or different and are each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.
[0110] Ar 1 is selected from a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group.
[0111] A is a divalent ethyl group, n is 0 or 1, and when n is 0, A and the bonds on both sides thereof do not exist.
[0112] The substituents in the "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, silyl, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, or a C3-C30 heteroaryl group.
[0113] Each heteroatom in the arylhetero, heterocycloalkyl, heterocycloalkenyl, or heteroaryl is independently at least one of N, O, S, Si, and P.
[0114] Specifically, the organic compound is selected from the following structures:
[0115]
[0116]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and known synthesis methods. The methods of the present invention are only exemplary, and the compounds obtained by replacing the above reactants in the general formula with commercially available raw materials or methods of the prior art are also included within the scope of this application.
[0129] Specific synthesis examples of this application are as follows:
[0130] Example 1: Preparation of Compound 1-1
[0131]
[0132] (1) Compound 1-1-0 (6.41 g, 37.9 mmol) and 1-1-1 (10.35 g, 37.9 mmol) were completely dissolved in 110 mL of xylene. Then, NaOtBu (4.17 g, 43.38 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 3.1 mmol), the mixture was heated and stirred for 3 hours. After the reaction was terminated, the resulting mixture was cooled to room temperature and extracted with water and ethyl acetate. The organic layer was dried over MgSO 4 and filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and n-hexane as the eluent to obtain intermediate compound 1-1-2 (11.90 g, yield 87%).
[0133] LC-MS (APCI): 362.37 (M+H + )
[0134] (2) 1-1-3 (42 g, 149.4 mmol) was dissolved in ethyl acetate (500 mL). Then, Raney nickel (20 g) was added and the reaction was carried out at room temperature for 48 hours. After the reaction was completed, the catalyst was removed using diatomaceous earth. Pd / C (10 g) catalyst was added and the hydrogenation reaction was carried out again at room temperature under a hydrogen pressure of about 100 psi for 72 hours. After the reaction was completed, the solvent was removed under reduced pressure. The product was separated and purified by silica gel column chromatography to obtain pure 1-1-4 (35.7 g, yield 83%).
[0135] LC-MS (APCI): 285.82 (M+H + )
[0136] (3) 1-1-4 (5.70 g, 20 mmol) was dissolved in tetrahydrofuran (200 mL). At -40 °C, n-butyllithium (13.2 mL, 1.6 mol / L) was slowly added dropwise and the mixture was stirred for half an hour. Triisopropyl borate (3.95 g, 21 mmol) was added dropwise at low temperature. The mixture was stirred at -40 °C for 1 hour and then at room temperature for 4 hours. Then, dilute hydrochloric acid (5%) was added and the mixture was stirred for 2 hours. The mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and n-hexane as the eluent to obtain pure 1-1-5 (4.15 g, yield 83%).
[0137] LC-MS (APCI): 251.48 (M+H + )
[0138] (4) 1-1-5 (10.53 g, 42.1 mmol) and compound 1-1-6 (23.36 g, 42.1 mmol) were added to a four-necked flask, followed by the addition of toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.97 g, 8.4 mmol). After purging with nitrogen three times, the mixture was heated and stirred for 3 hours. After the reaction was terminated, the resulting product was cooled to room temperature, washed with water, and the organic layer was dried over anhydrous magnesium sulfate and then filtered and concentrated. The intermediate compound 1-1-7 (9.66 g, yield: 58%) was obtained by purification using column chromatography or distillation.
[0139] LC-MS(APCI): 395.26(M+H + )
[0140] (5) Intermediate compound 1-1-79 (12.98 g, 32.8 mmol) and 1-1-2 (11.86 g, 32.8 mmol) were completely dissolved in 105 mL of xylene, then NaOtBu (4.17 g, 43.38 mmol) was added, and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 3.1 mmol) was added. After that, the mixture was heated and stirred for 3 hours. After the reaction was terminated, the resulting product was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and n-hexane as the eluent to obtain the target compound 1-1-8 (16.55 g, yield 70%).
[0141] LC-MS(APCI): 720.61(M+H + )
[0142] (6) 1-1-8 (25.37 g, 35.2 mmol) and compound 1-1-9 (4.72 g, 38.7 mmol) were added to a three-necked flask, followed by the addition of toluene (300 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.97 g, 8.4 mmol). After purging with nitrogen twice, the mixture was heated and stirred for 3 hours. After the reaction was terminated, the resulting product was cooled to room temperature, washed with water, and the organic layer was dried over anhydrous magnesium sulfate and then filtered and concentrated. The intermediate compound 1-1 (16.70 g, yield: 86%) was obtained by purification using column chromatography or distillation.
[0143] LC-MS(APCI): 718.34(M+H + )
[0144] Example 2: Preparation of Compound 1-11
[0145]
[0146] Compound 1-11 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-0 was replaced with Compound 1-11-0 and Compound 1-1-1 was replaced with Compound 1-11-1, to obtain Compound 1-11 (16.53 g, yield 73%).
[0147] LC-MS (APCI): 840.45 (M+H + )
[0148] Example 3: Preparation of Compound 1-20
[0149]
[0150] Compound 1-20 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-0 was replaced with Compound 1-20-0, Compound 1-1-1 was replaced with Compound 1-1-4, and Compound 1-1-3 was replaced with Compound 1-20-3, to obtain Compound 1-20 (14.61 g, yield 65%).
[0151] LC-MS (APCI): 892.16 (M+H + )
[0152] Example 4: Preparation of Compound 1-36
[0153]
[0154] Compound 1-36 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-1 was replaced with Compound 1-36-0 and 1-1-0 was replaced with 1-36-1, to obtain Compound 1-36 (15.48 g, yield 69%).
[0155] LC-MS (APCI): 854.74 (M+H + )
[0156] Example 5: Preparation of Compound 1-55
[0157]
[0158] Synthesize compound 1-55 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 1-55-0, 1-1-1 is replaced with 1-55-1, and 1-1-5 is replaced with 1-1-9, to obtain compound 1-55 (15.77 g, yield 72%).
[0159] LC-MS (APCI): 728.61 (M+H + )
[0160] Example 6: Preparation of Compound 2-15
[0161]
[0162] Synthesize compound 2-15 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 2-15-0 and 1-1-3 is replaced with 1-20-3, to obtain compound 2-15 (19.61 g, yield 65%).
[0163] LC-MS (APCI): 880.41 (M+H + )
[0164] Example 7: Preparation of Compound 2-44
[0165]
[0166] Synthesize compound 2-44 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 2-44-0, compound 1-1-1 is replaced with compound 2-44-1 (the synthesis of compound 2-44-1 refers to the synthesis of compound 1-20-7), and compound 1-1-5 is replaced with compound 1-1-9, to obtain compound 2-44 (15.81 g, yield 63%).
[0167] LC-MS (APCI): 768.19 (M+H + )
[0168] Example 8: Preparation of Compound 2-63
[0169]
[0170] Synthesize compound 2-63 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 2-63-0, compound 1-1-1 is replaced with compound 2-63-1, and compound 1-1-3 is replaced with compound 1-20-3, to obtain compound 2-63 (13.35 g, yield 77%).
[0171] LC-MS(APCI): 742.49 (M+H + )
[0172] Example 9: Preparation of Compound 2-64
[0173]
[0174] Compound 2-64 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-1 was replaced with Compound 2-64-1 and Compound 1-1-3 was replaced with Compound 1-20-3, to obtain Compound 2-64 (18.16 g, yield 69%).
[0175] LC-MS(APCI): 842.31 (M+H + )
[0176] Example 10: Preparation of Compound 3-20
[0177]
[0178] Compound 3-20 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-0 was replaced with Compound 1-20-0, 1-1-1 was replaced with 1-1-4, and 1-1-3 was replaced with 3-20-3, to obtain Compound 3-20 (15.49 g, yield 74%).
[0179] LC-MS(APCI): 866.79 (M+H + )
[0180] Example 11: Preparation of Compound 3-53
[0181]
[0182] Compound 3-53 was synthesized by referring to the synthesis method of Compound 1-1 in Reference Example 1, except that Compound 1-1-0 was replaced with Compound 3-53-0, Compound 1-1-1 was replaced with Compound 3-53-1 (the synthesis of Compound 3-53-1 was referred to the synthesis of Compound 3-20-7), and Compound 1-1-5 was replaced with Compound 3-53-5, to obtain Compound 3-53 (16.17 g, yield 76%).
[0183] LC-MS(APCI): 832.41 (M+H + )
[0184] Example 12: Preparation of Compound 3-62
[0185]
[0186] Synthesize compound 3-62 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 3-62-0, compound 1-1-1 is replaced with compound 3-62-1, and compound 1-1-3 is replaced with compound 3-62-3, to obtain compound 3-62 (14.51 g, yield 60%).
[0187] LC-MS (APCI): 716.37 (M+H + )
[0188] Example 13: Preparation of Compound 3-71
[0189]
[0190] Synthesize compound 3-71 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 3-71-0, compound 1-1-1 is replaced with compound 3-71-1, compound 1-1-3 is replaced with compound 3-62-3, and compound 3-62-6 is replaced with compound 3-72-6, to obtain compound 3-71 (13.96 g, yield 73%).
[0191] LC-MS (APCI): 830.82 (M+H + )
[0192] Example 14: Preparation of Compound 3-82
[0193]
[0194] Synthesize compound 3-82 according to the synthesis method of compound 1-1 in Reference Example 1, except that compound 1-1-0 is replaced with compound 3-71-0, 1-1-1 is replaced with 2-64-1, and 1-1-3 is replaced with 3-62-3, to obtain compound 3-82 (11.26 g, yield 69%).
[0195] LC-MS (APCI): 906.47 (M+H + )
[0196] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the above compounds and known synthesis methods, and other structures can also be obtained with reference to the above synthesis methods and conventional synthesis means in the art.
[0197] The following application examples further illustrate the application of the compounds described in the present invention in the preparation of organic electroluminescent devices.
[0198] Application Example 1:
[0199] This example provides an organic electroluminescent device, such asFigure 1 As shown, it includes a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting auxiliary layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a second electrode layer 8.
[0200] Comparative Example 1
[0201] HATCN was evaporated on an ITO substrate to form a first hole injection layer (HIL) with a thickness of HT was evaporated on the above first hole injection layer to form a hole transport layer (HTL) with a thickness of EB was evaporated on the above hole transport layer to form a light-emitting auxiliary layer (EBL) with a thickness of GH + GD (3 wt%) was evaporated on the light-emitting auxiliary layer to form a light-emitting layer (EML) with a thickness of An electron transport layer (ETL) with a thickness of was evaporated in sequence, and Al (with a thickness of ) was evaporated to form a cathode, thereby manufacturing an organic electroluminescent device.
[0202] The structural formulas of the materials of each layer of the device involved are as follows:
[0203]
[0204] Comparative Example 2
[0205] The organic electroluminescent device of Comparative Example 2 was prepared by the same method as the implementation scheme of Comparative Example 1 above, with the only difference being that the light-emitting auxiliary layer (EBL) was replaced from compound EB in the implementation scheme of Comparative Example 1 with compound EB-1.
[0206] Comparative Example 3
[0207] The organic electroluminescent device of Comparative Example 3 was prepared by the same method as the implementation scheme of Comparative Example 1 above, with the only difference being that the light-emitting auxiliary layer (EBL) was replaced from compound EB in the implementation scheme of Comparative Example 1 with compound EB-2.
[0208] Device Example 1
[0209] The organic electroluminescent device of Device Example 1 was prepared by the same method as the implementation scheme of Comparative Example 1 above, with the only difference being that the light-emitting auxiliary layer (EBL) was replaced from compound EB in the implementation scheme of Comparative Example 1 with compound 1-1.
[0210] Device Example 2
[0211] The organic electroluminescent device of Device Example 2 was prepared by the same method as the implementation scheme of Comparative Example 1 above, with the only difference being that the light-emitting auxiliary layer (EBL) was replaced from compound EB with compound 1-11.
[0212] Device Example 3
[0213] The organic electroluminescent device of Device Example 3 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-20 instead of EB.
[0214] Device Example 4
[0215] The organic electroluminescent device of Device Example 4 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-36 instead of Compound EB.
[0216] Device Example 5
[0217] The organic electroluminescent device of Device Example 5 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 1-55 instead of Compound EB in Comparative Example 1.
[0218] Device Example 6
[0219] The organic electroluminescent device of Device Example 6 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 2-15 instead of Compound EB.
[0220] Device Example 7
[0221] The organic electroluminescent device of Device Example 7 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 2-44 instead of Compound EB in Comparative Example 1.
[0222] Device Example 8
[0223] The organic electroluminescent device of Device Example 8 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 2-63 instead of Compound EB in Comparative Example 1.
[0224] Device Example 9
[0225] The organic electroluminescent device of Device Example 9 was prepared by the same method as that of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced by Compound 2-64 instead of Compound EB in Comparative Example 1.
[0226] Device Example 10
[0227] The organic electroluminescent device of Device Example 10 was prepared by the same method as in the implementation example of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 3-20 instead of Compound EB in the implementation example of Comparative Example 1.
[0228] Device Example 11
[0229] The organic electroluminescent device of Device Example 11 was prepared by the same method as in the implementation example of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 3-53 instead of Compound EB in the implementation example of Comparative Example 1.
[0230] Device Example 12
[0231] The organic electroluminescent device of Device Example 12 was prepared by the same method as in the implementation example of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 3-62 instead of Compound EB in the implementation example of Comparative Example 1.
[0232] Device Example 13
[0233] The organic electroluminescent device of Device Example 13 was prepared by the same method as in the implementation example of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 3-71 instead of Compound EB in the implementation example of Comparative Example 1.
[0234] Device Example 14
[0235] The organic electroluminescent device of Device Example 14 was prepared by the same method as in the implementation example of Comparative Example 1 above, except that the emission auxiliary layer (EBL) was replaced with Compound 3-82 instead of Compound EB in the implementation example of Comparative Example 1.
[0236] Evaluation of Organic Electroluminescent Element
[0237] Lifetime test method: A voltage was applied to the obtained organic electroluminescent element so that the current density reached 30 mA / cm 2 , and the time until the luminance became 95% of the initial luminance (LT95 (unit: hour)) was measured. Taking the lifetime of Comparative Example 1 as 100%, the relative lifetime values of each comparative example and example were obtained.
[0238] The driving voltage was tested at a current density of 15 mA / cm 2 . Taking the driving voltage of Comparative Example 1 as 100%, the relative driving voltage values of each comparative example and example were obtained.
[0239] The current efficiency was tested at a current density of 15 mA / cm 2 . Taking the current efficiency of Comparative Example 1 as 100%, the relative current efficiency values of each comparative example and example were obtained. The test results are shown in Table 1.
[0240] Table 1
[0241]
[0242]
[0243] From the results shown in Table 1 above, it can be seen that when the organic compound of the present invention is applied in the light-emitting auxiliary layer, the driving voltage is reduced compared with the comparative example, and the luminous efficiency and lifespan are significantly improved. Therefore, the compound of the present invention is suitable for preparing high-performance organic electroluminescent devices.
[0244] Those skilled in the art can easily understand that the above are only preferred embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.
Claims
1. An organic compound, characterized in that, the organic compound has the structure shown in formula (1), Wherein, R 1 , R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heteroalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; L 1 、L 2 Any one of them is selected from phenyl-substituted C6-C30 arylene groups, and the other is selected from a single bond, substituted or unsubstituted C6-C30 arylene groups, and substituted or unsubstituted C3-C30 heteroarylene groups; Ar 1 selected from substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; A is a divalent ethyl group, n is 0 or 1, and when n is 0, A and the bonds on both sides thereof do not exist; when the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, the heteroatoms in the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl are each independently at least one of N, O, S, Si, and P.
2. The organic compound according to claim 1, characterized in that, the organic compound has the structure shown in formula (2) or formula (3), In Formula (2) and Formula (3), L 1 , L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; R 1 and R 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heteroalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar 1 selected from substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; A is a divalent ethyl group, n is 0 or 1, and when n is 0, A and the bonds on both sides thereof do not exist; when the "substituted or unsubstituted" is substituted, the substituents are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, the heteroatoms in the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl are each independently at least one of N, O, S, Si, and P.
3. The organic compound according to claim 2, characterized in that, the organic compound has the structure shown in formula (4) or formula (11), Among them, L 1 、L 2 、R 1 、R 2 、Ar 1 are defined as described in claim 1.
4. The organic compound according to any one of claims 1-3, characterized in that, The Ar 1 is selected from the following groups:
5. The organic compound according to any one of claims 1-3, characterized in that, The L 1 , L 2 are the same or different and each independently selected from a single bond, a phenylene group, a phenyl-substituted phenylene group, a biphenylene group, a naphthylene group, an anthracene group, a phenanthrene group, a fluoranthene group, a pyrene group, a perylene group, a fluoranthene group, a terphenyl group, a phenylbiphenyl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a 9,9-dimethylfluorene group, a 9,9-diphenylfluorene group, a spirobifluorene group.
6. The organic compound according to any one of claims 1-3, characterized in that, R 1 and R 2 are the same or different and each independently selected from hydrogen, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, phenylbiphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl and any one of combinations of two or more of the above groups.
7. The organic compound according to any one of claims 1-3, characterized in that, the organic compound is selected from the following structures: 。 8. An organic electroluminescent element, characterized in that, the organic electroluminescent element includes: a first electrode; a second electrode arranged to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode and including a light-emitting layer, wherein one or more layers of the organic material layer contain the organic compound according to any one of claims 1-6.
9. The organic electroluminescent element according to claim 8, characterized in that, the organic material layer includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer contains the organic compound according to any one of claims 1-6.
10. An electronic device, characterized in that, the electronic device includes the organic electroluminescent element according to claim 9.