Organic compound, organic electroluminescent device, and electronic apparatus

Abstract

The present application belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescent device using same, and an electronic apparatus. The organic compound has a structure as shown in formula (1). When the organic compound is used in an organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

Organic compound, organic electroluminescent device and electronic device

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese Patent Application No. CN202410712098.7, filed on June 3, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD

[0003] The present application belongs to the technical field of organic materials, and particularly relates to an organic compound, an organic electroluminescent device and an electronic device. BACKGROUND

[0004] With the development of electronic technology and the progress of material science, the research range of electronic components and devices for electroluminescence or photoelectric conversion is becoming more and more extensive. Among them, the organic electroluminescent device, also known as organic light-emitting diode, is a phenomenon that the organic light-emitting material emits light under the excitation of electric current under the action of electric field. Such electronic components and devices generally include a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. Taking the organic electroluminescent device as an example, it generally includes an anode, a hole injection layer, a hole transport layer, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially stacked. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, the electrons on the cathode side move to the organic light-emitting layer, and the holes on the anode side also move to the organic light-emitting layer. The electrons and holes combine to form excitons in the organic light-emitting layer. The excitons in the excited state release energy to the outside, and then the organic light-emitting layer emits light.

[0005] In existing organic electroluminescent devices, the functional layer has a relatively low carrier mobility, which directly affects the driving voltage of the device, and also affects the thermal load of the light-emitting device, thereby affecting the brightness decay life of the light-emitting device. In order to improve the light-emitting performance of the organic electroluminescent device, by doping the hole injection layer with a suitable electron acceptor material (P-type doping) or / and doping the electron transport layer with an electron donor material (N-type doping), the carrier density in the light-emitting device can be significantly improved and the mobility of the carriers can be improved.

[0006] Although the prior art discloses a variety of P-type dopants, the existing P-type doping materials can solve the problem of stability to a certain extent, but their structures are complex, the preparation and use cost is high, and there is great economic pressure in actual use. Therefore, in order to improve the performance of OLED devices, obtain lower driving voltage and higher brightness decay life, it is crucial to develop more kinds of high-performance, low-cost P-type doping materials. SUMMARY

[0007] To solve the above problems, the present application aims to provide an organic compound, an organic electroluminescent device and an electronic device, which can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device, improving the device efficiency and the device lifetime.

[0008] The first aspect of the present application provides an organic compound having a structure as shown in formula 1:

[0009] wherein one of E and G is -O- or -S-, and the other is -N=;

[0010] one of Q and M is -O- or -S-, and the other is -N=;

[0011] R1and R2are the same or different, and are each independently selected from a substituted aryl group having 6 to 30 carbon atoms or a substituted heteroaryl group having 3 to 30 carbon atoms;

[0012] the substituents in R1and R2are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a deuterated aryl group having 6 to 20 carbon atoms, and the substituents in R1and R2each contain at least one of a halogen group, a cyano group and a haloalkyl group having 1 to 10 carbon atoms.

[0013] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described above.

[0014] The third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect of the present application.

[0015] The present application provides an organic compound shown in formula 1, which must contain a halogen group, a cyano group or a haloalkyl group, so that the compound has a lower LUMO energy level (Lowest Unoccupied Molecular Orbital) and better stability. When the organic compound is used as a P-type dopant for the hole injection layer of an organic electroluminescent device, the performance of the organic electroluminescent device such as the voltage and the lifetime can be greatly improved.

[0016] Other features and advantages of the present application will be described in detail in the following specific embodiments. BRIEF DESCRIPTION OF DRAWINGS

[0017] The accompanying drawings are included to provide a further understanding of the present application, and are incorporated in and constitute a part of the specification, illustrate embodiments of the present application and serve to explain the principles of the present application, but are not intended to limit the present application.

[0018] FIG. 1 is a structural schematic diagram of an organic electroluminescent device according to the present application.

[0019] FIG. 2 is a structural schematic diagram of an electronic device according to the present application.

[0020] Reference numerals 100, anode 200, cathode 300, functional layer 310, hole injection layer 320, hole transport layer 330, light-emitting adjustment layer 340, organic light-emitting layer 350, electron transport layer 360, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0021] In view of the above problems existing in the prior art, the present application aims to provide an organic compound, and an organic electroluminescent device and an electronic device comprising the same, which can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device, improving the efficiency and the lifetime of the device.

[0022] The first aspect of the present application provides an organic compound having a structure as shown in Formula 1:

[0023] wherein one of E and G is -O- or -S-, and the other is -N=;

[0024] one of Q and M is -O- or -S-, and the other is -N=;

[0025] R1and R2are the same or different, and are each independently selected from a substituted aryl group having 6 to 30 carbon atoms or a substituted heteroaryl group having 3 to 30 carbon atoms;

[0026] the substituents in R1and R2are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a deuterated aryl group having 6 to 20 carbon atoms, and the substituents in R1and R2are each selected from at least one of a halogen group, a cyano group, and a haloalkyl group having 1 to 10 carbon atoms.

[0027] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0028] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, cyano, halogen groups, alkyl, haloalkyl, aryl, deuterated aryl, cycloalkyl, etc. The number of substituents can be one or more.

[0029] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0030] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0031] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. In the present application, aryl group refers to a monovalent aromatic ring or its derivative, which contains 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25 or 30 carbon atoms. In some embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-30 carbon atoms, in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-25 carbon atoms, in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-20 carbon atoms, in other embodiments, the aryl group is a substituted or unsubstituted aryl group with 6-12 carbon atoms.

[0032] In the present application, the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent group on the aryl group, for example, the substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituent group is 18.

[0033] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group can 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 with 6-30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-20 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-12 carbon atoms.

[0034] In the present application, the aryl group as a substituent of R1and R2includes, but is not limited to, phenyl, naphthyl and the like.

[0035] In the present application, heteroaryl group refers to a monovalent aromatic ring or its derivative, which contains 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl group can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, but is not limited thereto.

[0036] In the present application, the number of carbon atoms of a substituted or unsubstituted heteroaryl group can 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.

[0037] In the present application, a substituted heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms in the heteroaryl group is replaced with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a deuterated aryl group, a halogenated aryl group, or the like. It should be understood that the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0038] In the present application, an alkyl group having 1 to 10 carbon atoms can include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of an alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0039] In the present application, a halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0040] In the present application, a halogenated alkyl group can be, for example, a trifluoromethyl group.

[0041] In the present application, a deuterated aryl group refers to an aryl group having at least one deuterium substituent, and specific examples of a deuterated aryl group include, but are not limited to, a penta-deuterated phenyl group.

[0042] In the present application, the number of carbon atoms of a cycloalkyl group having 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of a cycloalkyl group include, but are not limited to, a cyclopentyl group, a cyclohexyl group, an adamantyl group.

[0043] In the present application, an indefinite bond refers to a single bond extending from a ring system which indicates that one end of the bond can be connected to any position in the ring system through which the bond extends, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to the rest of the molecule through two indefinite bonds that extend through the bicyclic ring system, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (f-1) to (f-10).

[0044] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through an indeterminate bond extending from the middle of one of the benzene rings, and the meaning represented thereby includes any possible connection as shown in formula (X'-1) to formula (X'-4).

[0045] In some embodiments of the present application, the organic compound is selected from the group consisting of the structures represented by formula A to formula F:

[0046] In formula A to formula F, R1and R2are the same or different, and each is independently selected from a substituted aryl group having 6 to 30 carbon atoms or a substituted heteroaryl group having 3 to 30 carbon atoms;

[0047] The substituents in R1and R2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a deuterated aryl group having 6 to 20 carbon atoms, and the substituents in R1and R2each contain at least one of a halogen group, a cyano group, and a haloalkyl group having 1 to 10 carbon atoms.

[0048] In some embodiments of the present application, R1and R2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 18, 29, or 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0049] In some embodiments of the present application, R1and R2are the same, and selected from a substituted aryl group having 6 to 30 carbon atoms or a substituted heteroaryl group having 3 to 30 carbon atoms.

[0050] Alternatively, the substituents in R1and R2are the same, and selected from a halogen group, a cyano group, and a haloalkyl group having 1 to 10 carbon atoms, and when the number of substituents in R1and R2is greater than 1, each substituent is the same or different.

[0051] In some embodiments of the present application, R1and R2are the same or different, and each is independently selected from a substituted aryl group having 6 to 18 carbon atoms or a substituted heteroaryl group having 3 to 18 carbon atoms.

[0052] Optionally, the substituents in R1 and R2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, phenyl or pentadeuterated phenyl, and the substituents in R1 and R2 each contain at least one of fluorine, cyano and haloalkyl with 1 to 5 carbon atoms.

[0053] In some embodiments of this application, R1 and R2 are the same and are selected from substituted aryl groups with 6 to 18 carbon atoms and substituted heteroaryl groups with 3 to 18 carbon atoms.

[0054] Optionally, the substituents in R1 and R2 are the same and are selected from halogen groups, cyano groups and haloalkyl groups having 1 to 5 carbon atoms. When the number of substituents in R1 and R2 is greater than 1, the substituents may be the same or different.

[0055] In other embodiments of this application, R1 and R2 may be the same or different, and are independently selected from substituted phenyl, substituted naphthyl, substituted biphenyl, substituted phenanthryl, substituted fluorenyl, substituted triazine, substituted pyridyl, substituted pyrimidinyl, substituted pyrazinyl, substituted dibenzofuranyl, substituted dibenzothiopheneyl, substituted carbazolyl, substituted quinolinyl, substituted isoquinolinyl, and substituted quinazolinyl.

[0056] Optionally, the substituents in R1 and R2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, phenyl or pentadeuterated phenyl, and the substituents in R1 and R2 each contain at least one of fluorine, cyano and trifluoromethyl.

[0057] In some embodiments of this application, R1 and R2 are the same and are selected from substituted phenyl, substituted naphthyl, substituted biphenyl, substituted phenanthryl, substituted fluorenyl, substituted triazine, substituted pyridyl, substituted pyrimidinyl, substituted pyrazinyl, substituted dibenzofuranyl, substituted dibenzothiopheneyl, substituted carbazolyl, substituted quinolinyl, substituted isoquinolinyl, and substituted quinazolinyl.

[0058] Optionally, the substituents in R1 and R2 are the same and are selected from fluorine, cyano, or trifluoromethyl. When the number of substituents in R1 and R2 is greater than 1, the substituents may be the same or different.

[0059] In some embodiments of this application, R1 and R2 may be the same or different, and are each independently selected from the group consisting of:

[0060] Specifically, R1 and R2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0061] In some embodiments of the present application, the organic compound is selected from the group consisting of the following compounds:

[0062] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode and a cathode oppositely arranged, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound of the present application.

[0063] Optionally, the organic electroluminescent device is a red organic electroluminescent device. As shown in FIG. 1, the organic electroluminescent device can comprise an anode 100, a hole injection layer 310, a hole transport layer 320, an emission adjustment layer 330, an organic emission layer 340, an electron transport layer 350, and a cathode 200, which are sequentially stacked.

[0064] Optionally, the anode 100 comprises an anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include 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, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is used.

[0065] Optionally, the hole transport layer 320 comprises one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can select from the prior art, which is not specifically limited in the present application. In some embodiments of the present application, the hole transport layer 320 is HT-17.

[0066] Optionally, the light-emitting adjustment layer 330 (also referred to as a hole adjustment layer, an electron blocking layer, a hole auxiliary layer, a hole buffer layer, a light-emitting auxiliary layer, or a second hole transport layer) can comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, without special limitation in the present application. For example, in some embodiments of the present application, the light-emitting adjustment layer 330 is composed of HT-18.

[0067] Optionally, a hole injection layer 310 can also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, without special limitation in the present application. The material of the hole injection layer 310 can be selected from the organic compounds of the present application, for example. In one embodiment of the present application, the hole injection layer 310 is composed of an organic compound of the present application and HT-17.

[0068] Optionally, the organic light-emitting layer 340 can be composed of a single light-emitting layer material, or can comprise a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material, and the holes injected into the organic light-emitting layer 340 and the electrons injected into the organic light-emitting layer 340 can recombine to form excitons in the organic light-emitting layer 340, the excitons transfer energy to the host material, the host material transfers energy to the dopant material, and the dopant material is thus able to emit light.

[0069] The host material of the organic light-emitting layer 340 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, without special limitation in the present application.

[0070] In some embodiments of the present application, the host material of the organic light-emitting layer 340 is RH-1

[0071] The guest material of the organic light-emitting layer 340 can be a compound or derivative thereof having a condensed aryl ring, a compound or derivative thereof having a heteroaryl ring, an aromatic amine derivative, or other materials, without special limitation in the present application. The guest material is also referred to as a dopant material or dopant. Specific examples of red light phosphorescent dopants for red organic electroluminescent devices include, but are not limited to:

[0072] In a more specific embodiment, the host material of the organic light-emitting layer 340 is RH-1, and the guest material is RD-1.

[0073] The electron transport layer 350 can be a single layer structure or a multi-layer structure, and can include one or more electron transport materials selected from, but not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in the present application. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0074] In some embodiments of the present application, the electron transport layer 350 is composed of ET-13 and LiQ.

[0075] Optionally, as shown in FIG. 1, an electron injection layer 360 is further 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 can include inorganic materials such as alkali metal sulfides, alkali metal halides, or can include complexes of alkali metals and organic matters. For example, the electron injection layer 360 includes ytterbium (Yb).

[0076] In some embodiments of the present application, the electron injection layer 360 can include ytterbium (Yb).

[0077] In the present application, the cathode 200 can include a cathode material which is a material with small work function that helps injecting electrons into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode including magnesium and silver is included as the cathode.

[0078] Optionally, there is an organic capping layer on the cathode 200.

[0079] The third aspect of the present application provides an electronic device including the organic electroluminescent device of the second aspect of the present application.

[0080] According to an embodiment, as shown in FIG. 2, the provided electronic device is an electronic device 400 including the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, for example, can include, but are not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0081] The synthesis method of the organic compound of the present application will be specifically described below in combination with the synthesis examples, but the present application is not limited in this way.

[0082] Synthesis Examples

[0083] Those skilled in the art will recognize that the chemical reactions described in the application can be used to prepare many of the organic compounds described in the application, and that other methods for preparing the compounds of the application are also within the scope of the application. For example, the synthesis of the non-exemplified compounds according to the application can be successfully performed by modifications apparent to those skilled in the art, e.g. by appropriately protecting interfering groups, by utilizing other known reagents and / or reaction conditions, or by making routine modifications. The compounds of the application that are not mentioned in the application are prepared by analogous methods.

[0084] Synthesis of intermediate IM A-1

[0085] First, 4,6-diamino-2,5-dibromo-1,3-benzenediol (29.80 g, 100 mmol) was added to a 1000 mL two-necked flask, and then the air in the flask was completely replaced with argon. A syringe was used to add 300 mL of o-xylene solvent and pentafluorobenzaldehyde (43.14 g, 220 mmol) to the flask, and the oil bath was heated to 120°C for 5 h. After the system solution was cooled to room temperature, the argon protection was removed, and then 4-methoxy-TEMPO (5.03 g, 27.00 mmol, 4-methoxy-TEMPO, 5 mol%) was added, and the reaction was stirred at 120°C in the presence of oxygen for 15 h. After the solvent o-xylene was removed by distillation under reduced pressure, column chromatography was used to purify to obtain intermediate IM A-1 (36.40 g, yield: 56%).

[0086] Referring to the synthesis method of intermediate IM A-1, the intermediates shown in Table 1 were synthesized, with the difference that raw material 1 in Table 1 was used instead of 4,6-diamino-2,5-dibromo-1,3-benzenediol, and raw material 2 was used instead of pentafluorobenzaldehyde, to obtain intermediates IM A-2 to IM A-24.

[0087] Table 1

[0088] Synthesis of intermediate IM B-X

[0089] Malononitrile (4.86 g, 73.60 mmol) was added to THF (200 mL) under nitrogen protection, sodium hydride (3.54 g, 147.6 mmol) was added at 0 °C, and the mixture was stirred for 10 min and then allowed to warm to room temperature. Intermediate IM A-1 (19.17 g, 29.50 mmol) and tetrakis(triphenylphosphine)palladium (1.71 g, 1.48 mmol) were added under nitrogen, and the mixture was allowed to warm to 75 °C after nitrogen was bubbled for 20 min. After complete conversion, the solvent was removed, the mixture was cooled to room temperature, diluted with dilute hydrochloric acid (1 N, 400 mL), and a large amount of solid was precipitated. The solid was filtered, the filter cake was washed with water, and dried to give intermediate IM B-1, which was used in the next step without further purification.

[0090] The intermediates shown in Table 2 were synthesized according to the synthetic method of intermediate IM B-1, except that the starting material 3 in Table 2 was used instead of intermediate IM A-1 to give intermediate IM B-2 to intermediate IM B-24.

[0091] Table 2

[0092] Synthesis of Compound 1

[0093] Intermediate IM B-1 (18.00 g, 29.02 mmol) was added to 300 mL of DCM under nitrogen protection, nitrogen was bubbled for 20 min, and then PIFA (bistrifluoroacetyl iodobenzene, 10.50 g, 24.35 mmol) was added. The mixture was stirred at room temperature overnight, the solution was black, and the starting material was completely converted. The mixture was directly purified by column chromatography (eluent: PE (petroleum ether): DCM (dichloromethane) = 1:1) to give Compound 1 (15.30 g, yield: 85%). Mass (m / z) = 619.00 [M+H] + .

[0094] The compounds shown in Table 3 were synthesized according to the synthetic method of Compound 1, except that the starting material 4 in Table 3 was used instead of IM B-1; the starting material, structure, yield, and mass spectrum of the synthesized compound are shown in Table 3.

[0095] Table 3

[0096] The NMR data of some of the compounds are shown in Table 4 below

[0097] Table 4

[0098] Preparation of an organic electroluminescent device

[0099] Example 1: Preparation of a red organic electroluminescent device

[0100] The device was prepared by the following process:

[0101] On an experimental substrate with an ITO / Ag / ITO thickness of 1000 / 200 / 1500 A, surface treatment was performed using ultraviolet, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned using an organic solvent to remove impurities and oil on the surface of the experimental substrate.

[0102] On the experimental substrate, compound HT-17 and compound 1 were co-evaporated at a deposition rate ratio of 96:4% to form a hole injection layer with a thickness of 100 A.

[0103] On the hole injection layer, compound HT-17 was evaporated to form a hole transport layer with a thickness of 100 A.

[0104] On the hole transport layer, compound HT-18 was evaporated to form an emission adjustment layer with a thickness of 100 A.

[0105] On the emission adjustment layer, RH-1 and RD-1 were co-evaporated at a deposition rate ratio of 98:2% to form an organic light-emitting layer with a thickness of 100 A.

[0106] On the organic light-emitting layer, compound ET-13 and LiQ were co-evaporated at a deposition rate ratio of 60:40% to form an electron transport layer with a thickness of 100 A.

[0107] On the electron transport layer, Yb was evaporated to form an electron injection layer with a thickness of 100 A.

[0108] On the electron injection layer, magnesium (Mg) and silver (Ag) were co-evaporated at a deposition rate ratio of 10:90% to form a cathode with a thickness of 1000 A.

[0109] On the cathode, compound CP-1 was evaporated to form an organic capping layer with a thickness of 100 A, thereby completing the preparation of a red organic electroluminescent device.

[0110] Examples 2 to 24:

[0111] An organic electroluminescent device was fabricated using the same method as in Example 1, except that the compound shown in Table 5 below was used instead of compound 1 in forming the hole injection layer. ​​​​​​​​​

[0112] Comparative Example 1 to Comparative Example 2

[0113] An organic electroluminescent device was produced using the same method as in Example 1, except that Compound A and Compound B in Table 5 below were used instead of Compound 1 when forming the hole injection layer.

[0114] The main material structures used in the above examples and comparative examples are shown below:

[0115] The red organic electroluminescent devices prepared in Examples 1-24 and Comparative Examples 1-2 were tested for performance, specifically the IVL performance of the devices was tested at 10 mA / cm 2 The T 95 The device lifetime was tested at 30 mA / cm 2 The test results are shown in Table 5 below:

[0116] Table 5

[0117] As can be seen from Table 5, the use of the compounds of the present application as hole injection materials in Examples 1-24 resulted in a reduction in voltage of at least 0.22 V, an increase in current efficiency of at least 17.6%, and an increase in device lifetime of at least 13.7% compared to Comparative Examples 1-2. Thus, the use of the organic compounds of the present application in the injection layer of an organic electroluminescent device can reduce the device voltage and improve the luminous efficiency and T 95 lifetime of the organic electroluminescent device.

[0118] The above describes some embodiments of the present application in detail in conjunction with the drawings, but the present application is not limited to the specific details of the above-described embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. Organic compound, characterized in that, The compound has a structure shown in Formula 1: one of E and G is -O- or -S-, and the other is -N=; one of Q and M is -O- or -S-, and the other is -N=; R1 and R2 are the same or different, and are each independently selected from a substituted aryl group having 6 to 30 carbon atoms or a substituted heteroaryl group having 3 to 30 carbon atoms; the substituents in R1 and R2 are the same or different, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a deuterated aryl group having 6 to 20 carbon atoms, and the substituents in R1 and R2 each contain at least one of a halogen group, a cyano group, and a haloalkyl group having 1 to 10 carbon atoms.

2. The organic compound according to claim 1, characterized by The organic compound is selected from the group consisting of structures shown in Formula A to Formula F: In formulae A to F, R1 and R2 are as defined in claim 1.

3. The organic compound according to claim 1 or 2, characterized by R1 and R2 are the same or different, and are each independently selected from a substituted aryl group having 6 to 18 carbon atoms or a substituted heteroaryl group having 3 to 18 carbon atoms.

4. The organic compound according to any one of claims 1 to 3, characterized by the substituents in R1 and R2 are the same or different, and are each independently selected from deuterium, fluorine, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a phenyl group, or a penta-deuterated phenyl group, and the substituents in R1 and R2 each contain at least one of fluorine, a cyano group, and a haloalkyl group having 1 to 5 carbon atoms.

5. The organic compound according to any one of claims 1 to 4, characterized by R1 and R2 are the same or different, and are each independently selected from a substituted phenyl group, a substituted naphthyl group, a substituted biphenyl group, a substituted phenanthryl group, a substituted fluorenyl group, a substituted triazinyl group, a substituted pyridyl group, a substituted pyrimidinyl group, a substituted pyrazinyl group, a substituted dibenzofuranyl group, a substituted dibenzothiophenyl group, a substituted carbazolyl group, a substituted quinolyl group, a substituted isoquinolyl group, and a substituted quinazolinyl group.

6. The organic compound according to any one of claims 1 to 5, characterized by the substituents in R1 and R2 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 i-propyl group, a t-butyl group, a trifluoromethyl group, a phenyl group, or a penta-deuterated phenyl group, and the substituents in R1 and R2 each contain at least one of fluorine, a cyano group, and a trifluoromethyl group.

7. The organic compound according to any one of claims 1 to 6, characterized by R1and R2are the same or different and independently selected from the group consisting of:

8. The organic compound according to any one of claims 1 to 7, characterized by R1and R2are the same or different and independently selected from the group consisting of:

9. The organic compound according to any one of claims 1 to 8, characterized by The organic compound is selected from the group consisting of:

10. An organic electroluminescent device, characterized by comprising oppositely disposed anode and cathode, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 9; optionally, the functional layer comprises a hole injection layer; the hole injection layer comprises the organic compound; optionally, the hole injection layer further comprises a hole transport material; optionally, the organic electroluminescence device is a red organic electroluminescence device.

11. An electronic device, characterized by comprising the organic electroluminescence device according to claim 10.

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