Organic compounds, compositions, organic electroluminescent devices and electronic devices
By designing a new organic compound with a core structure connected to the triazine ring and dehydrobenzoline, the shortcomings in the performance improvement of organic electrophotographic equipment in the prior art are solved, and more efficient and stable photoelectric performance is achieved.
Patent Information
- Application Number
- JP2024563308
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-03-01
- Filing Date
- 2023-10-10
- Publication Date
- 2025-05-09
- Estimated Expiration
- 2043-10-10
AI Technical Summary
The prior art still has shortcomings in improving the performance of organic electrophotographic devices, especially in reducing driving voltages, increasing efficiency and extending life.
A new organic compound is adopted, whose core structure includes a triazine ring connected to dehydrobenzoline, extending the aromatic conjugation range and reducing molecular symmetry through a special dehydrogenation substitution group, thereby improving energy transport and crystalline properties.
This organic compound significantly improves photoelectric stability and film formation performance, and is suitable for use as the main substance of the light emitting layer in organic electrophotographic equipment, achieving lower driving voltage, higher efficiency and longer equipment life.
Smart Images

Figure 2025514860000001_ABST
Abstract
Description
[Technical field]
[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application claims priority to Chinese patent application having application number CN202310071951.7 filed on January 11, 2023, and Chinese patent application having application number CN202310184175.1 filed on March 1, 2023, the entire contents of which are hereby incorporated by reference into this application.
[0002] The present application relates to the technical field of organic compounds, and in particular to organic compounds and compositions containing such organic compounds, organic electroluminescent devices and electronic devices. [Background technology]
[0003] With the development of electronic technology and the progress of material science, the application range of electronic elements for realizing electroluminescence is becoming wider and wider. Such electronic elements generally include a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. The functional layer is made of multiple organic or inorganic film layers, and usually includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. Taking an organic electroluminescence device as an example, it usually includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode, which are stacked in order. When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, electrons on the cathode side move to the organic light-emitting layer, and holes on the anode side also move to the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy to the outside, causing the organic light-emitting layer to emit light to the outside.
[0004] The prior art discloses host materials that can be used to fabricate organic light-emitting layers in organic electroluminescent devices. However, there is still a need to continue developing new materials to further improve the performance of electronic components. Summary of the Invention [Problem to be solved by the invention]
[0005] In order to solve the above problems, the present application aims to provide an organic compound and a composition containing the organic compound, an organic electroluminescent device, and an electronic device, which can improve the performance of the organic electroluminescent device and the electronic device, for example by reducing the driving voltage of the device and improving the efficiency and lifetime of the device. [Means for solving the problem]
[0006] According to a first aspect of the present application, there is provided an organic compound having the structure shown in Formula 1: [ka]
[0007] provided that Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group; L, L1 and L2 are the same or different and each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Ar3 is [ka] and The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.
[0008] According to a second aspect of the present application, there is provided a composition comprising a first compound disclosed in the first aspect of the present application and a second compound having the structure shown in Formula 2. [ka]
[0009] According to a third aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises an organic compound disclosed in the first aspect of the present application or a composition disclosed in the second aspect of the present application.
[0010] According to a fourth aspect of the present application, there is provided an electronic apparatus, the electronic apparatus comprising an organic electroluminescent device as disclosed in the third aspect of the present application. Effect of the Invention
[0011] In the core structure of the organic compound of the present application, a triazine group is linked to phenylcarbazolyl through a nitrogen atom, one benzene ring on the carbazolyl ring is fully deuterated, and a penta-deuterated phenyl group is linked to another benzene ring. The introduction of a deuterated phenyl group as a substituent on one side of the carbazolyl group can expand the aromatic conjugation range of the molecular structure and reduce the molecular symmetry, so that the material has better energy transport properties and reduced crystallinity. The special asymmetric deuteration of the carbazolyl group can effectively improve the stability of the molecular structure and further reduce the molecular symmetry, thereby significantly improving the photoelectric stability and film formability of the material. The organic compound of the present application has good carrier transport properties, energy transfer properties and photoelectric stability, and is suitable for use as a host material for the emission layer in an organic electroluminescent device, and the organic electroluminescent device using it as a host material has obviously improved life characteristics while maintaining low driving voltage and high luminous efficiency.
[0012] Other features and advantages of the present application are described in detail in the detailed description that follows. The drawings are intended to provide a further understanding of the present application, constitute a part of the specification, and together with the following detailed description are intended to explain the present application and are not intended to be limitations thereon. [Brief description of the drawings]
[0013] [Figure 1] FIG. 1 is a structural schematic diagram of an organic electroluminescent device according to the present application. [Diagram 2] 1 is a structural schematic diagram of an electronic device according to the present application; DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0014] In view of the above problems existing in the prior art, the objective of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device comprising the organic compound, which can improve the performance of the organic electroluminescent device and the electronic device, for example, by reducing the driving voltage of the device and improving the efficiency and lifetime of the device.
[0015] According to a first aspect of the present application, there is provided an organic compound having the structure shown in Formula 1: [ka]
[0016] provided that Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group; L, L1 and L2 are the same or different and each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Ar3 is [ka] and The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.
[0017] The statements "each ... independently", "each ... independently" and "each of ... independently" used by the present application are interchangeable and should all be understood in a broad sense, and may mean that specific options with the same symbol in different groups do not affect each other, and may mean that specific options with the same symbol in the same group do not affect each other. For example, [ka] wherein each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine and chlorine" means that formula Q-1 has q substituents R" on the benzene ring, each R" may be the same or different, and the options for each R" do not affect each other, and formula Q-2 means that formula Q-2 has q substituents R" on each benzene ring of biphenyl, the number q of R" substituents on the two benzene rings may be the same or different, each R" may be the same or different, and the options for each R" do not affect each other.
[0018] In the present application, the term "substituted or unsubstituted" refers to the functional group described after the term having or not having a substituent (hereinafter, for convenience of explanation, the substituent is referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent Rc may be, for example, deuterium, cyano group, halogen group, alkyl group, halogenated alkyl group, deuterated alkyl group, aryl group, deuterated aryl group, halogenated aryl group, heteroaryl group, cycloalkyl group, etc. The number of substitutions may be one or more.
[0019] In this application, a "plurality" refers to two or more, such as 2, 3, 4, 5, 6, etc.
[0020] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, when L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms in the arylene group and the substituents therein is 12.
[0021] In the present application, aryl is any functional group or substituent derived from an aromatic carbon ring. The aryl group may be a monocyclic aryl group (e.g., a phenyl group) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked via a carbon-carbon bond, a monocyclic aryl group and a fused ring aryl group linked via a carbon-carbon bond, or two or more fused ring aryl groups linked via a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups conjugated and linked via a carbon-carbon bond may be considered as an aryl group in the present application. Here, the fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., a naphthyl group), a tricyclic fused aryl group (e.g., a phenanthrenyl group, a fluorenyl group, an anthryl group), etc. The aryl group does not include a heteroatom such as B, N, O, S, P, Se, or Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorene, anthranyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, chrysene, spirobifluorene, etc. An arylene group in the context of this application is a divalent group formed by an aryl group losing one more hydrogen atom.
[0022] In the present application, the terphenyl group is [ka] Includes.
[0023] In this application, the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group; for example, a substituted aryl group having 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.
[0024] In the present application, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
[0025] In the present application, the fluorene group may be substituted with one or more substituents, provided that any two adjacent substituents may be bonded to each other to form a ring structure. When the fluorene group is substituted, the substituted fluorene group may be: [ka] It may be, but is not limited to, the following.
[0026] In the present application, the aryl groups of the substituents of L, L1, L2, Ar1 and Ar2 include, but are not limited to, phenyl and naphthyl groups.
[0027] In this application, a heteroaryl group refers to a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, which may be one or more of B, O, N, P, Si, Se and S. A heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, a heteroaryl may be a single aromatic ring system or multiple aromatic ring systems linked via carbon-carbon bonds, and any aromatic ring system is one aromatic monocyclic or one aromatic fused ring. Exemplary heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazole, triazolyl, pyridine, bipyridyl, pyrimidine, triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinoxaline, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, and the like. In one embodiment, the aryl group may include, but is not limited to, an alkyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazole group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like.
[0028] In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.
[0029] In this application, a substituted aryl may have one or more hydrogen atoms in the aryl replaced with a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a halogenated alkyl group, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group is the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
[0030] In the present application, the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, and an n-hexyl group.
[0031] In the present application, a halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
[0032] In the present application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups, and the like.
[0033] In this application, specific examples of halogenated alkyl groups include, but are not limited to, trifluoromethyl groups.
[0034] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.
[0035] In the present application, the number of carbon atoms in a cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of cycloalkyl groups include, but are not limited to, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.
[0036] In the present application, a non-fixed bond is a single bond extending from a ring system. [ka] It means that one end of this bond can be connected to any position of the ring system through which the bond penetrates, and the other end can be connected to another part of the compound molecule. As an example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to another position of the molecule via two non-fixed bonds penetrating the two rings, which means that any of the possible connection methods represented by formulas (f-1) to (f-10) are included. [ka]
[0037] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is linked to another position of the molecule via a non-fixed bond extending from the middle of one benzene ring, which means that any of the possible linking methods represented by formulae (X'-1) to (X'-4) is included. [ka]
[0038] In some specific embodiments of the present application, the organic compound is selected from the compounds shown in formula AA, formula BB, formula CC, or formula DD. [ka]
[0039] In some embodiments of the present application, L, L1 and L2 are the same or different and are each independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
[0040] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.
[0041] In another embodiment of the present application, L, L1 and L2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
[0042] Optionally, L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl or phenyl.
[0043] Further optionally, L, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups: [ka]
[0044] Specifically, L, L1 and L2 are the same or different and each independently represents a single bond or a group selected from the group consisting of the following groups: [ka]
[0045] In some embodiments of the present application, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.
[0046] Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or a pentadeuterophenyl group.
[0047] In another embodiment of the present application, Ar1 and Ar2 are the same or different and each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group.
[0048] Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, or pentadeuterophenyl.
[0049] In another embodiment of the present application, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group W, where the unsubstituted group W is selected from the group consisting of: [ka]
[0050] however, [ka] represents a chemical bond, the substituted group W having one or more substituents each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, or pentadeuterophenyl, and when the number of substituents on group W is greater than one, each substituent may be the same or different.
[0051] Optionally, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of: [ka]
[0052] Specifically, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following groups: [ka]
[0053] In some embodiments of the present application, [ka] are each independently selected from the group consisting of the following groups: [ka]
[0054] in particular, [ka] are each independently selected from the group consisting of the following groups: [ka]
[0055] In some embodiments of the present application, in formula 1 [ka] is selected from the group consisting of the following groups: [ka]
[0056] Specifically, in Eq. [ka] is selected from the group consisting of the following groups: [ka] TIFF2025514860000028.tif242166
[0057] In some embodiments of the present application, the organic compound is selected from the group consisting of the following compounds: [ka] TIFF2025514860000030.tif251165TIFF2025514860000031.tif242165TIFF202 5514860000032.tif242165TIFF2025514860000033.tif254165TIFF20255148600 00034.tif254165TIFF2025514860000035.tif254165TIFF2025514860000036.t if254165TIFF2025514860000037.tif254165TIFF2025514860000038.tif254165 TIFF2025514860000039.tif254165TIFF2025514860000040.tif254165TIFF202 5514860000041.tif254165TIFF2025514860000042.tif254165TIFF20255148600 00043.tif254165TIFF2025514860000044.tif254165TIFF2025514860000045.t if255164TIFF2025514860000046.tif254165TIFF2025514860000047.tif220165
[0058] A second aspect of the present application is a composition comprising a first compound and a second compound, The present invention further provides a composition wherein the first compound has the structure shown in Formula 1 and the second compound has the structure shown in Formula 2. [ka]
[0059] provided that R4, R5, R6, and R7 are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; n4 represents the number of substituents R4 and is selected from 1, 2, 3, or 4. When n4 is greater than 1, any two R4s may be the same or different; n5 represents the number of substituents R5 and is selected from 1, 2, or 3. When n5 is greater than 1, any two R5s may be the same or different; n6 represents the number of substituents R6 and is selected from 1, 2, or 3. When n6 is greater than 1, any two R6 are the same or different; n7 represents the number of substituents R7 and is selected from 1, 2, 3, or 4. When n7 is greater than 1, any two R7s may be the same or different; L4 and L5 are the same or different and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Ar4 and Ar5 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L4, L5, Ar4 and Ar5 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.
[0060] In some embodiments of the present application, the second compound has the structure shown in formula 2-3-3. [ka]
[0061] In some embodiments of the present application, in the second compound, each of R4, R5, R6, and R7 is independently selected from hydrogen, deuterium, fluorine, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, a phenyl group, a naphthyl group, a biphenyl group, or a pentadeuterophenyl group.
[0062] In some embodiments of the present application, in the second compound, each R4, R5, R6, and R7 is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or the following groups: [ka]
[0063] In some embodiments of the present application, in the second compound, L4 and L5 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
[0064] Optionally, the substituents in L4 and L5 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and a phenyl group.
[0065] In another embodiment of the present application, in the second compound, L4 and L5 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolylene group.
[0066] Optionally, the substituents in L4 and L5 are each independently selected from deuterium, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, or phenyl.
[0067] In some embodiments of the present application, in the second compound, L4 and L5 are each independently selected from a single bond, a substituted or unsubstituted group U, where the unsubstituted group U is selected from the group consisting of: [ka]
[0068] however, [ka] represents a chemical bond, the substituted group U having one or more substituents each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, t-butyl, and phenyl, and when the number of substituents on U is greater than one, each substituent is the same or different.
[0069] Optionally, L4 and L5 are each independently selected from the group consisting of a single bond or the following groups: [ka]
[0070] In some embodiments of the present application, in the second compound, Ar4 and Ar5 are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
[0071] Optionally, the substituents in Ar4 and Ar5 are each independently selected from deuterium, a halogen group, an alkyl group having 1 to 5 carbon atoms, a phenyl group, or a pentadeuterophenyl group.
[0072] In another embodiment of the present application, in the second compound, Ar4 and Ar5 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted triphenylene group.
[0073] Optionally, the substituents in Ar4 and Ar5 are each independently selected from deuterium, fluorine, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, or pentadeuterophenyl.
[0074] In some embodiments of the present application, in the second compound, Ar4 and Ar5 are each independently selected from a substituted or unsubstituted group G, and the unsubstituted group G is selected from the group consisting of: [ka]
[0075] however, [ka] represents a chemical bond, the substituted group G having one or more substituents each independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, or pentadeuterophenyl, and when the number of substituents on G is greater than one, each substituent is the same or different.
[0076] Optionally, in the second compound, Ar4 and Ar5 are each independently selected from the group consisting of: [ka]
[0077] In some embodiments of the present application, [ka] are each independently selected from the group consisting of the following groups: [ka]
[0078] in particular, [ka] are each independently selected from the group consisting of the following groups: [ka]
[0079] In some embodiments of the present application, the second compound is selected from the group formed by the following compounds: [ka] TIFF2025514860000062.tif255158TIFF2025514860000063.tif226160TIFF2025514860000064.tif51160
[0080] Alternatively, the composition is a mixture of the first and second compounds. For example, the first and second compounds may be mixed uniformly by mechanical stirring to form the mixture.
[0081] In the present application, the relative content of the two compounds in the composition is not particularly limited, and can be selected according to the specific application of the organic electroluminescent device. Generally, based on the total weight of the composition, the mass percentage of the first compound may be 1% to 99%, and the mass percentage of the second compound may be 1% to 99%. For example, in the composition, the mass ratio of the first compound to the second compound may be 1:99, 20:80, 30:70, 40:60, 45:65, 50:50, 55:45, 60:40, 70:30, 80:20, 99:1, etc.
[0082] In some embodiments of the present application, the composition comprises a first compound and a second compound, and the mass percentage of the first compound is 20% to 80%, and the mass percentage of the second compound is 20% to 80%, based on the total weight of the composition.
[0083] In some preferred embodiments, the composition has a mass percentage of the first compound of 30% to 60% and a mass percentage of the second compound of 40% to 70% based on the total weight of the composition, and in this case, when the composition is used in an organic electroluminescence device, the device can have both high luminous efficiency and long service life. Preferably, the mass percentage of the first compound is 40% to 60% and the mass percentage of the second compound is 40% to 60% based on the total weight of the composition. More preferably, the mass percentage of the first compound is 40% to 50% and the mass percentage of the second compound is 50% to 60%.
[0084] The present application further provides the use of said composition as a host material in the light-emitting layer of an organic electroluminescent device.
[0085] A third aspect of the present application further provides an organic electroluminescent device comprising an anode and a cathode provided opposite to each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising an organic compound represented by formula 1 of the present application or a composition containing a first compound and a second compound.
[0086] In one embodiment of the present application, the functional layer comprises an organic light-emitting layer comprising an organic compound as shown in Formula 1 of the present application.
[0087] In one embodiment of the present application, the functional layer comprises an organic light-emitting layer comprising a composition containing a first compound and a second compound according to the present application.
[0088] In one embodiment of the present application, said organic electroluminescent device is a phosphorescent device.
[0089] In one particular embodiment according to the present application, the organic electroluminescent device is a green organic electroluminescent device.
[0090] In some embodiments of the present application, the organic electroluminescent device includes, in order, an anode (ITO substrate), a hole transport layer, a hole auxiliary layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic coating layer.
[0091] In one particular embodiment according to the present application, as shown in FIG. 1 , the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, the functional layer 300 including a hole injection layer 310, a hole transport layer 320, a hole auxiliary layer 330, an organic light-emitting layer 340, an electron transport layer 350, and an electron injection layer 360.
[0092] Optionally, the anode 100 includes the following anode materials, preferably with a large work function that favors hole injection into the functional layer. Examples of anode materials include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline. Preferably, the anode includes a transparent electrode with indium tin oxide (ITO) as the anode.
[0093] Optionally, the hole transport layer 320 may include one or more hole transport materials selected from carbazole polymers, carbazole-linked triarylamine-based compounds, or other types of compounds, although the present application is not particularly limited thereto. As an example, in some embodiments of the present application, the hole transport layer 320 is made of HT-01.
[0094] Optionally, the hole auxiliary layer 330 may include one or more hole transport materials, which may be selected from carbazolyl polymers, carbazolyl-linked triarylamine compounds, or other types of compounds, and the present application is not particularly limited thereto. As an example, in some embodiments of the present application, the hole auxiliary layer 330 is made of HT-02. The hole auxiliary layer is also called a second hole transport layer, a hole buffer layer, a hole adjustment layer, or an electron barrier layer.
[0095] Alternatively, organic light-emitting layer 340 may be composed of a single light-emitting material or may include a host material and a guest material. Optionally, organic light-emitting layer 340 is composed of a host material and a guest material, and holes and electrons injected into organic light-emitting layer 330 recombine in organic light-emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, causing the guest material to emit light.
[0096] The guest material of the organic light-emitting layer 340 may be a compound having a fused aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other material, and is not particularly limited in this application.
[0097] In some embodiments of the present application, for a green organic electroluminescent device, the organic light-emitting layer 340 includes an organic compound described in the present application, a second compound, and a guest material Ir(ppy) 3 .
[0098] The electron transport layer 350 may have a single layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not particularly limit this. As an example, in one embodiment of the present application, the electron transport layer 350 is composed of ET-01 and LiQ.
[0099] Optionally, the cathode 200 includes the following cathode materials, which are materials with small work functions that contribute to electron injection into the functional layer: Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, etc., or alloys thereof; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, BaF2 / Ca, etc. It is preferable to include a metal electrode containing silver and magnesium as the cathode.
[0100] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability of injecting holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not particularly limit the same. In one embodiment of the present application, the hole injection layer 310 may be made of CuPC and HT-01.
[0101] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability of injecting electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).
[0102] A fourth aspect of the present application further provides an electronic device, the electronic device comprising an organic electroluminescent device as described herein.
[0103] As an example, as shown in FIG. 2, the electronic device provided in the present application is a first electronic device 400 including any organic electroluminescent device described in the above-mentioned organic electroluminescent device embodiment. This electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, and can include, but are not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects and will not be mentioned again in the present application.
[0104] The present application will be described in detail below with reference to examples, but the following description is for interpreting the present application and is not intended to limit the scope of the present application in any manner.
[0105] Synthesis of intermediate IM-a-no: [ka] Under the protection of nitrogen gas, 2,3-dichloronitrobenzene (20.0 g, 104.2 mmol), d5-2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (47.9 g, 229.2 mmol), tetrakistriphenylphosphine palladium (4.8 g, 4.2 mmol), potassium carbonate (57.6 g, 416.7 mmol), tetrabutylammonium bromide (13.4 g, 41.2 mmol), toluene (320 mL), ethanol (80 mL) and deionized water (80 mL) were added to a round-bottom flask, and the mixture was heated to 75 °C-80 °C and reacted with stirring for 72 h. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography using a mixed solvent eluent of dichloromethane / n-heptane to obtain a colorless oily intermediate IM-a-no (17.7 g, yield: 60%).
[0106] The intermediates shown in Table 1 below were synthesized by referring to the synthesis method of intermediate IM-a-no and using reactant A instead of 2,3-dichloronitrobenzene.
[0107] [Table 1]
[0108] Synthesis of intermediate IM-a-nh: [ka] Under the protection of nitrogen gas, the intermediate IM-a-no (16.0 g, 56.1 mmol), triphenylphosphine (36.8 g, 140.2 mmol), and O-dichlorobenzene (150 mL) were added to a round-bottom flask, and the mixture was heated to 175 ° C ~ 180 ° C under stirring conditions and reacted for 36 hours. The reaction solution was cooled to room temperature, deionized water was added, and the liquid was separated. The organic phase was washed with water and then dried with anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure conditions, and the obtained crude was purified by silica gel column chromatography using a mixed solvent eluent of dichloromethane / n-heptane to obtain a white solid intermediate IM-a-nh (9.2 g, yield: 65%).
[0109] Following the same procedure as for intermediate IM-a-nh, the intermediates shown in Table 2 below were synthesized using reactant B instead of intermediate IM-a-no.
[0110] [Table 2]
[0111] Synthesis of compound A5: [ka] Under the protection of nitrogen gas, the intermediate IM-a-nh (5.0 g, 19.8 mmol), 2-chloro-4-(dibenzofuranyl-3-yl)-6-phenyl-1,3,5-triazine (10.6 g, 29.7 mmol) and N,N-dimethylformamide (50 mL) were added to a round-bottom flask, the mixture was cooled to -5°C to 0°C with stirring, sodium hydride (0.6 g, 23.4 mmol) was added, and the reaction was carried out at -5°C to 0°C with stirring for 1 hour, and then heated to 20°C to 25°C and reacted for 24 hours. The reaction was stopped, the reaction solution was washed with water and then separated, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using a mixed solvent eluent of dichloromethane / n-heptane, and then recrystallized and purified using a mixed solvent of toluene / n-heptane to obtain a white solid compound A5 (8.0 g, yield: 70%).
[0112] The compounds shown in Table 3 below were synthesized by referring to the synthesis method of compound A5, using reactant C instead of intermediate IM-a-nh and reactant D instead of 2-chloro-4-(dibenzofuranyl-3-yl)-6-phenyl-1,3,5-triazine.
[0113] [Table 3] TIFF2025514860000071.tif227159TIFF2025514860000072.tif255157TIFF2025514860000073.tif243158
[0114] Synthesis of compound A45: [ka] Under the protection of nitrogen gas, the intermediate IM-a-nh (5.0 g, 19.8 mmol), 2-(biphenyl-4-yl)-4-(4-chlorobenzene)-6-phenyl-1,3,5-triazine (8.7 g, 20.8 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.4 g, 0.2 mmol), sodium tert-butoxide (2.9 g, 29.7 mmol) and xylene (50 mL) were added to a round-bottom flask, and the mixture was reacted at 135 °C-140 °C for 16 h with stirring. The reaction mixture was cooled to room temperature, washed with water and then separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of dichloromethane / n-heptane as an eluent. The product was then recrystallized and purified using a mixed solvent of toluene / n-heptane to obtain white solid compound A45 (9.4 g, yield: 75%).
[0115] The compounds shown in Table 4 below were synthesized by using a method similar to that for compound A45, but using reactant E in the following table instead of intermediate IM-a-nh, and reactant F instead of 2-(biphenyl-4-yl)-4-(4-chlorobenzene)-6-phenyl-1,3,5-triazine.
[0116] [Table 4] TIFF2025514860000076.tif229166TIFF2025514860000077.tif251166TIFF202 5514860000078.tif251166TIFF2025514860000079.tif251166TIFF2025514860 000080.tif251166TIFF2025514860000081.tif251166TIFF2025514860000082. tif255164TIFF2025514860000083.tif253166TIFF2025514860000084.tif41166
[0117] Mass spectral data for some of the compounds is shown in Table 5 below.
[0118] [Table 5] TIFF2025514860000086.tif235165
[0119] NMR data for some compounds is shown in Table 6 below.
[0120] [Table 6]
[0121] Fabrication and performance evaluation of organic electroluminescence devices Example 1 Green organic electroluminescent device First, the anode was pretreated according to the following process: ITO / Ag / ITO substrates with thicknesses of 110 Å / 1100 Å / 100 Å were surface-treated using UV ozone and O2:N2 plasma to increase the work function of the anode, and the ITO substrate surface was cleaned using an organic solvent to remove impurities and oil stains on the ITO substrate surface.
[0122] On the experimental substrate (anode), CuPC:HT-01 was co-evaporated at a deposition rate ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of 110 Å, and HT-01 was vacuum-evaporated onto the HIL to form a hole transport layer with a thickness of 1230 Å.
[0123] HT-02 was evaporated onto the hole transport layer to form a hole assisting layer having a thickness of 360 Å.
[0124] On the hole assisting layer, the composition GH-1-1 and Ir(ppy)3 were co-deposited at a deposition rate ratio of 100%:10% to form an organic light-emitting layer (green organic light-emitting layer) having a thickness of 300 Å.
[0125] ET-01 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form an electron transport layer with a thickness of 340 Å. Yb was evaporated on the electron transport layer to form an electron injection layer with a thickness of 15 Å. Magnesium and silver were co-evaporated on the electron injection layer in an evaporation ratio of 1:9 to form a cathode with a thickness of 120 Å.
[0126] In addition, CP-01 was evaporated onto the cathode to form an organic coating layer (CPL) with a thickness of 700 Å, thereby realizing the fabrication of an organic light-emitting device.
[0127] Example 2-84: When forming the organic light-emitting layer, the GH-XY host material composition shown in Table 7 was used instead of the composition GH-1-1 in Example 1, and an organic electroluminescence device was fabricated in the same manner as in Example 1.
[0128] Comparative Example 1-6: An organic electroluminescent device was fabricated using the same method as in Device Example 1, except that GH-XY was used in forming the organic light-emitting layer.
[0129] In the above examples and comparative examples, the host material composition GH-XY used was a mixture of the first compound in Table 7 below and the second compound in Table 7 below, and the specific composition was as shown in Table 7. However, the mass ratio was the ratio value between the mass percentage of the first compound shown in the table and the mass percentage of the second compound shown in the table. The composition GH-1-1 is taken as an example for explanation. As can be seen from Table 7, GH-1-1 was a mixture of compound A5 and compound 49 in a mass ratio of 40:60, and for example, the host material GH-D1-1 in Comparative Example 1 was a mixture of compound I and compound 5 in a mass ratio of 40:60.
[0130] The second compound used is shown below. Compound 5 was obtained according to the description in patent document JP3139321B2, compound 12 was obtained according to the description in patent document CN103518271B, compound 35 was obtained according to the description in patent document US9564595B2, compound 36 was obtained according to the description in patent document CN104205393B, and compound 49 was obtained according to the description in patent document KR1020220013910A. [ka]
[0131] The structural formulas of other main materials used in Examples 1 to 83 and Comparative Examples 1 to 6 are shown below. [ka]
[0132] Specifically, the organic electroluminescence device manufactured as described above was subjected to a current of 10 mA / cm 2 The IVL performance of the device was tested under the conditions of 20mA / cm and the lifetime of the T95 device was measured under the conditions of 20mA / cm 2 The test results are shown in Table 7.
[0133] [Table 7] TIFF2025514860000091.tif255166TIFF2025514860000092.tif255166TIFF2025514860000093.tif25516 6TIFF2025514860000094.tif255166TIFF2025514860000095.tif252169TIFF2025514860000096.tif99169
[0134] As can be seen from the above table, compared to Comparative Examples 1 to 6, the current efficiency of the devices of Examples 1 to 84 was increased by at least 10.1%, and the lifetime was extended by at least 16.0%.
[0135] Compared with Comparative Examples 1 and 2, when the organic compound of Formula 1 of the present application is used as a blue photoelectron host material, the device produced has a significantly extended lifespan characteristic when the driving voltage and efficiency are close. The reason for this may be that the compound of the present application is deuterized at a specific position of the phenylcarbazolyl core structure, which improves its photoelectric stability, compared with Compound I.
[0136] Compared with Comparative Examples 3 and 4, when the organic compound of Formula 1 of the present application is used as a blue photoelectron host material, the device prepared has obviously reduced driving voltage and improved luminous efficiency. The reason for this may be that, compared with the carbazolyl group with hole characteristics in Compound II, the compound of the present application uses a neutral or electron group to link to the triazine group, which gives the molecule better electron injection and transport properties, and improves the injection and combination efficiency of carriers.
[0137] The device life of the compound of the present application was significantly extended compared to that of the compound III of the comparative example, as compared to the comparative example 5. When the reason for this was investigated, it was possible that the compound of the present application was deuterized at a specific position of the carbazolyl group compared to the compound III, thereby improving its photoelectric stability.
[0138] Compared with Comparative Example 6, the compound of the present application has improved both the device life and efficiency compared with Comparative Example Compound IV. When the reason for this is investigated, it may be because, compared with Compound IV, in the compound of the present application, only one benzene ring of the carbazolyl group is fully deuterized, and such a deuterium form can effectively control the local symmetry of the molecular structure and reduce the intermolecular force, thereby improving the amorphous stability and film formation properties of the material.
[0139] Those skilled in the art can easily conceive of other embodiments of the present application after considering the specification and practicing the invention disclosed herein. This application is intended to cover any modifications, uses or adaptations of the present application, which modifications, uses or adaptations follow the general principles of the present application and include common sense or customary technical means known in the art that are not disclosed herein. The specification and examples are considered to be exemplary only, with a true scope and spirit of the present application being indicated by the following claims. [Explanation of symbols]
[0140] 100, anode 200, cathode 300, Functional Layer 310, hole injection layer 320, hole transport layer 330, hole auxiliary layer 340 , organic light-emitting layer 350, electron transport layer 360, electron injection layer 400, 1st electronic equipment
Claims
1. 1. An organic compound having the structure shown in Formula 1. 【Chemistry 48】 (However, Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothienyl group; L, L 1 and L 2 are the same or different and are each independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Ar 3 teeth, 【Chemistry 49】 and L, L 1 , L 2 , Ar 1 and Ar 2 The substituents in are the same or different and are each independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.
2. L, L 1 and L 2 are the same or different and are each independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; Optionally, L, L 1 and L 2 2. The organic compound according to claim 1, wherein the substituents in are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.
3. L, L 1 and L 2 are the same or different and each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; Optionally, L, L 1 and L 2 are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, or a phenyl group.
4. Ar 1 and Ar 2 are the same or different and each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group; Optionally, Ar 1 and Ar 2 The organic compound according to any one of claims 1 to 3, wherein the substituents in are the same or different and are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, a phenyl group, or a pentadeuterophenyl group. 【Request 5】 【Chemical 50】 and each of the groups independently selected from the group consisting of the following groups: 【Chemistry 51】
6. In Equation 1 【Chemistry 52】 is selected from the group consisting of the following groups: 【Chemistry 53】
7. 7. The organic compound according to claim 1, which is selected from the group consisting of the following compounds: 【Chemical 54】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】
8. A composition comprising a first compound and a second compound, The composition, characterized in that the first compound is selected from the organic compounds according to any one of claims 1 to 7, and the second compound is selected from the compounds shown in formula 2. 【Chemistry 55】 (However, each R 4 , R 5 , R 6 , R 7 are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; n 4 is a substituent R 4 is selected from 1, 2, 3, or 4; 4 If is greater than 1, then any two R 4 are the same or different, n 5 is a substituent R 5 is selected from 1, 2, or 3; 5 If is greater than 1, then any two R 5 are the same or different, n 6 is a substituent R 6 is selected from 1, 2, or 3; 6 If is greater than 1, then any two R 6 are the same or different, n 7 is a substituent R 7 is selected from 1, 2, 3, or 4; 7 If is greater than 1, then any two R 7 are the same or different, L 4 , L 5 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Ar 4 and Ar 5 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; L 4 , L 5 , Ar 4 and Ar 5 The substituents in are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
9. In the second compound, each R 4 , R 5 , R 6 , R 7 are each independently selected from hydrogen, deuterium, fluorine, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, a phenyl group, a naphthyl group, a biphenyl group, or a pentadeuterophenyl group.
10. In the second compound, L 4 and L 5 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group; Optionally, L 4 and L 5 The composition according to claim 8 or 9, wherein the substituents in are each independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, a phenyl group, or a pentadeuterophenyl group.
11. In the second compound, Ar 4 and Ar 5 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted triphenylene group; Optionally, Ar 4 and Ar 5 The composition according to any one of claims 8 to 10, wherein the substituents in are each independently selected from deuterium, fluorine, a cyano group, a halogen group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, a phenyl group, or a pentadeuterophenyl group.
12. The composition according to any one of claims 8 to 11, characterized in that the second compound is selected from the group formed by the following compounds: 【Chemistry 56】 【change】 【change】
13. An organic electroluminescence device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, The functional layer comprises an organic compound according to any one of claims 1 to 7 or a composition according to any one of claims 8 to 12, Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes an organic compound according to any one of claims 1 to 7 or a composition according to any one of claims 8 to 12; Optionally, the organic electroluminescent device is a green organic electroluminescent device.
14. 14. An electronic device comprising an organic electroluminescent device according to claim 13.
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