Organic compound, organic electroluminescence device, and electronic device

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescent device using the same and an electronic device. The organic compound is composed of a fused aromatic ring of tetramethylcyclohexane and an indolocarbazole connection. The organic compound is used in an organic electroluminescent device, and the performance of the organic electroluminescent device can be significantly improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and more specifically, to an organic compound and an organic electroluminescent device and electronic apparatus using the same. Background Technology

[0002] In recent years, self-emissive organic light-emitting diodes (OLEDs), which can be driven by low voltage, have attracted much attention as a next-generation display element compared to mainstream flat panel displays, namely liquid crystal displays (LCDs), due to their superior performance in viewing angle and contrast, ease of achieving thinner and lighter designs without the need for backlights, low power consumption, and wide color reproduction range. To date, many materials suitable for use in OLEDs have been disclosed. However, OLEDs using currently known materials are not easily commercialized due to their high driving voltage, low efficiency, and short lifespan. Therefore, it is necessary to develop materials with excellent properties to achieve OLEDs that can be driven by low voltage while possessing high brightness and long lifespan. Summary of the Invention

[0003] The purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device using the same, which have high luminous efficiency and long service life.

[0004] To achieve the above objectives, the first aspect of this application provides an organic compound having a structure as shown in Formula 1:

[0005]

[0006] Wherein, ring A is selected from benzene ring, dibenzofuran ring, dibenzothiophene ring or dimethylfluorene ring;

[0007] Rings C, B, and D may be the same or different, and are independently selected from aromatic rings having 6 to 14 carbon atoms;

[0008] L1 and L2 are independently selected from single bonds and substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophene groups with 6 to 30 carbon atoms, respectively.

[0009] Ar is selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophene groups, and substituted or unsubstituted carbazoyl groups with 6 to 40 carbon atoms.

[0010] R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0011] n1 represents the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, any two R1s are the same or different.

[0012] n2 represents the number of substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different.

[0013] n3 represents the number of substituents R3, and n3 is selected from 0, 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different.

[0014] The substituents in L1, L2, and Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, dibenzofuranyl, dibenzothiophenyl, carbazoyl, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0015] A second aspect of this application provides an organic electroluminescent device, including 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 the organic compound described in the first aspect of this application;

[0016] Preferably, the functional layer includes an organic light-emitting layer, the organic light-emitting layer containing the organic compound;

[0017] Preferably, the organic electroluminescent device is a red organic electroluminescent device.

[0018] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0019] The core group of the organic compound in this application consists of an aromatic ring of fused tetramethylcyclohexane linked to indobenzocarbazole. Indobenzocarbazole possesses a large conjugated area, endowing the compound with excellent hole transport properties. The fusion of the tetramethylcyclohexane structure with a benzene ring or a dibenzo five-membered ring further enhances the compound's hole transport capability through hyperconjugation. Furthermore, the four methyl groups of tetramethylcyclohexane provide steric hindrance, allowing for precise control of intermolecular packing and enabling the formation of a good amorphous thin film. When the compound of this application is used as the host material of the luminescent layer (especially as a hole transport material in a hybrid host material), it can improve carrier balance in the luminescent layer, broaden the carrier recombination region, and improve exciton generation and utilization efficiency, thereby improving the device's luminous efficiency and lifetime.

[0020] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0021] The accompanying drawings are provided to further illustrate the present application and form part of the specification. They are used together with the following detailed description to explain the present application, but do not constitute a limitation thereof. In the drawings:

[0022] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0023] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0024] Figure Labels

[0025] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0026] 320, Hole transport layer 320, First hole transport layer 330, Second hole transport layer 340, Organic light-emitting layer

[0027] 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device. Detailed Implementation

[0028] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device containing the organic compound. The organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0029] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0030]

[0031] Wherein, ring A is selected from benzene ring, dibenzofuran ring, dibenzothiophene ring or dimethylfluorene ring;

[0032] Rings C, B, and D may be the same or different, and are independently selected from aromatic rings having 6 to 14 carbon atoms;

[0033] L1 and L2 are independently selected from single bonds and substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophene groups with 6 to 30 carbon atoms, respectively.

[0034] Ar is selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophene groups, and substituted or unsubstituted carbazoyl groups with 6 to 40 carbon atoms.

[0035] R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0036] n1 represents the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, any two R1s are the same or different.

[0037] n2 represents the number of substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different.

[0038] n3 represents the number of substituents R3, and n3 is selected from 0, 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different.

[0039] The substituents in L1, L2, and Ar may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, dibenzofuranyl, dibenzothiophenyl, carbazoyl, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0040] In this application, the fluorene group can be replaced by one or two substituents. Specifically, when the fluorene group is replaced, the following substitutions can be made: etc., but not limited to this.

[0041] 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.

[0042] 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 group, alkyl, haloalkyl, deuteralkyl, trialkylsilyl, aryl, deuteralkyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, cycloalkyl, etc. The number of substituents can be one or more.

[0043] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0044] 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.

[0045] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups 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. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0046] In this application, terphenyl includes

[0047] In this application, the number of carbon atoms in the 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 with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0049] In this application, the aryl groups used as substituents for L1, L2, and Ar are, for example, but not limited to, phenyl, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, phenanthrene, etc.

[0050] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0051] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0052] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0053] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0054] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0055] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0056] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0057]

[0058] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0059]

[0060] In some embodiments of this application, ring C, ring B, and ring D may be the same or different, and are each independently selected from benzene rings or naphthalene rings.

[0061] In some embodiments of this application, the organic compound is selected from compounds represented by formulas 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, or 1-25.

[0062]

[0063]

[0064] In some embodiments of this application, R1, R2, or R3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, or phenyl.

[0065] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophene groups with 6 to 15 carbon atoms.

[0066] Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0067] In other embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or substituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0068] Optionally, the substituents in L1 and L2 may be the same or different, and may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0069] Further optionally, L1 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or substituted biphenylene, substituted or unsubstituted fluorene.

[0070] Further optionally, L2 is selected from single bonds, phenylene, or naphthylene.

[0071] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0072]

[0073] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; when the substituted group V2 contains multiple substituents, the substituents may be the same or different.

[0074] Specifically, L1 is selected from the group consisting of single bonds or the following groups:

[0075]

[0076] Specifically, L2 is selected from the group consisting of single bonds or the following groups:

[0077]

[0078] In some embodiments of this application, Selected from the group consisting of the following groups:

[0079]

[0080]

[0081] Specifically, Selected from the group consisting of the following groups:

[0082]

[0083] In some embodiments of this application, Selected from the group consisting of the following groups:

[0084]

[0085]

[0086] Specifically, Selected from the group consisting of the following groups:

[0087]

[0088]

[0089] In some embodiments of this application, Ar is selected from substituted or unsubstituted aryl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophene groups, and substituted or unsubstituted carbazole groups having 6 to 20 carbon atoms.

[0090] Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, trideuterated methyl groups, or phenyl groups.

[0091] In other embodiments of this application, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoyl.

[0092] Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.

[0093] In some embodiments of this application, Ar is selected from substituted or unsubstituted groups V1, wherein the unsubstituted groups V1 are selected from the group consisting of:

[0094]

[0095] in, The substituted group V1 contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, or phenyl; when the substituted group V1 contains multiple substituents, the substituents may be the same or different.

[0096] Alternatively, Ar is selected from the group consisting of:

[0097]

[0098] Specifically, Ar is selected from the group consisting of the following groups:

[0099]

[0100]

[0101] In some embodiments of this application, Selected from the group consisting of the following groups:

[0102]

[0103] Specifically, Selected from the group consisting of the following groups:

[0104]

[0105]

[0106] Optionally, the organic compounds in this application are selected from the group consisting of:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] A second aspect of this application provides an organic electroluminescent device, which includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the aforementioned organic compound to improve the voltage characteristics, efficiency characteristics and lifetime characteristics of the organic electroluminescent device.

[0120] Optionally, the organic compounds provided in this application can be used to form at least one organic film layer in the functional layer.

[0121] Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.

[0122] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 320, a second hole transport layer (hole auxiliary layer) 330, an organic light-emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially.

[0123] In this application, anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials 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, anode 100 includes indium tin oxide (ITO) as a transparent electrode for the anode.

[0124] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0125]

[0126] In one embodiment of this application, the first hole transport layer 320 may be composed of HT-23.

[0127] In one embodiment of this application, the second hole transport layer 330 may be composed of HT-24.

[0128] Optionally, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof:

[0129]

[0130]

[0131] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-23.

[0132] In this application, the organic light-emitting layer 340 can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0133] The main material of the organic light-emitting layer 340 may include metal chelate compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials.

[0134] Optionally, the organic compound of this application is used as the host material (hole transport type host material) of the organic light-emitting layer 340.

[0135] In some embodiments of this application, the electron transport host material of the organic light-emitting layer 340 is... (RH-N).

[0136] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to:

[0137]

[0138] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 340 comprises the organic compound of this application and RH-N, and the guest material is RD.

[0139] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 350 includes, but is not limited to, the following compounds:

[0140]

[0141] In one embodiment of this application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0142] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials 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 multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0143] Optionally, an electron injection layer 360 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 360 may include ytterbium (Yb).

[0144] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0145] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0146] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments.

[0147] In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0148] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0149] Synthesis example

[0150] Generally, the organic compounds of this application can be prepared by the methods described herein. Unless otherwise specified, the meanings of the substituent symbols in this application are the same as those in Chemical Formula I. Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many other organic compounds of this application, and other methods for preparing the organic compounds of this application are considered to be within the scope of this application.

[0151] For example, those skilled in the art can synthesize other organic compounds of this application by referring to or appropriately modifying the preparation methods provided in this application, such as by using appropriate protecting groups, utilizing other known reagents other than those described in this application, or modifying reaction conditions.

[0152] In the synthesis examples described below, all temperatures are in degrees Celsius unless otherwise stated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company, and Alfa Chemical Company, and were used without further purification unless otherwise stated. Some common reagents were purchased from Shantou Xilong Chemical Plant, Guangdong Guanghua Chemical Reagent Plant, Guangzhou Chemical Reagent Plant, Tianjin Haoyuyu Chemical Co., Ltd., Tianjin Fuchen Chemical Reagent Plant, Wuhan Xinhuayuan Technology Development Co., Ltd., Qingdao Tenglong Chemical Reagent Co., Ltd., and Qingdao Haiyang Chemical Plant.

[0153] Unless otherwise stated, the following reactions are generally carried out under positive pressure of nitrogen or argon, or with a drying tube attached to an anhydrous solvent; reaction flasks are sealed with suitable rubber stoppers, and the substrate is injected into the reaction flasks using a syringe. All glassware is dried.

[0154] 1 H NMR spectra were recorded using a Bruker 400MHz or 600MHz NMR spectrometer. 1 ¹H NMR spectra were prepared using CDCl₃, CD₂Cl₂, D₂O, DMSO-d₆, CD₃OD, or acetone-d₆ as solvents (in ppm), with TMS (0 ppm) or chloroform (7.26 ppm) as reference standards.

[0155] Synthesis of Sub-a1:

[0156]

[0157] Under nitrogen protection, 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (13.36 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), toluene (140 mL), tetrahydrofuran (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (12.82 g, yield 86%).

[0158] Referring to the synthesis of Sub-a1, Sub-a2 and Sub-a8 were synthesized by replacing 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene with reactant A shown in Table 1 and replacing 4-chlorophenylboronic acid with reactant B.

[0159] Table 1: Synthesis of Sub-a2 and Sub-a8

[0160]

[0161] Synthesis of Sub-b1:

[0162]

[0163] Under nitrogen protection, 9-bromo-7H-benzo[C]carbazole (14.80 g, 50 mmol), 1-(4-iodobenzyl)naphthalene (19.81 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol), and N,N-dimethylformamide (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, filtered, and the filtrate was collected. The filtrate was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid (17.94 g; yield 72%).

[0164] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b18 were synthesized by replacing 9-bromo-7H-benzo[C]carbazole with reactant C shown in Table 2 and replacing 1-(4-iodobenzyl)naphthalene with reactant D.

[0165] Table 2: Synthesis of Sub-b2 to Sub-b18

[0166]

[0167]

[0168] Synthesis of Sub-c1:

[0169]

[0170] Under nitrogen protection, Sub-b1 (24.92 g, 50 mmol), o-chloroaniline (6.38 g, 50 mmol), tris(dibenzylacetone)palladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid Sub-c1 (15.26 g; yield 56%).

[0171] Sub-c2 to Sub-c13 were synthesized by replacing Sub-b1 with reactant E as shown in Table 3 and replacing o-chloroaniline with reactant F, as in Sub-c1.

[0172] Table 3: Synthesis of Sub-c2 to Sub-c13

[0173]

[0174]

[0175] Synthesis of Sub-d1:

[0176]

[0177] Under nitrogen protection, Sub-c1 (27.25 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol), and N,N-dimethylacetamide (260 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid, Sub-d1 (13.48 g; yield 53%).

[0178] Sub-d2 to Sub-d13 were synthesized by replacing Sub-c1 with reactant G as shown in Table 4, referring to Sub-d1.

[0179] Table 4: Synthesis of Sub-d2 to Sub-d13

[0180]

[0181]

[0182] Synthesis of Sub-d14:

[0183]

[0184] Under nitrogen protection, 2-bromo-6-phenylnaphthalene (14.15 g, 50 mmol), 5,7-dihydro-indolo[2,3-B]carbazole (14.10 g, 55 mmol), tris(dibenzylacetone)palladium (0.916 g, 1 mmol), X-Phos (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid Sub-d14 (14.51 g; yield 63%).

[0185] Referring to Sub-d14, Sub-d15 to Sub-d18 were synthesized by replacing 2-bromo-6-phenylnaphthalene with reactant H as shown in Table 5 and replacing 5,7-dihydro-indolo[2,3-B]carbazole with reactant J.

[0186] Table 5: Synthesis from Sub-d15 to Sub-d18

[0187]

[0188] Synthesis of compound A1:

[0189]

[0190] Under nitrogen protection, 7,9-dihydro-7-phenyl-benzo[G]indolo[2,3-B]carbazole (9.56 g, 25 mmol), Sub-a1 (8.96 g, 30 mmol), tris(dibenzylacetone)dipalladium (0.46 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase, yielding a white solid (11.60 g; yield 72%, m / z = 645.3 [M+H]). + ).

[0191] Referring to the synthesis of compound A1, reactant K was used instead of 7,9-dihydro-7-phenyl-benzo[G]indolo[2,3-B]carbazole as shown in Table 6, and reactant L was used instead of Sub-a1 to synthesize the following compounds of this application.

[0192] Table 6: Synthesis of the compounds in this application

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] NMR data for some compounds are shown in Table 7 below.

[0199] Table 7

[0200]

[0201] Fabrication and evaluation of organic electroluminescent devices:

[0202] This application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the aforementioned organic compound of this application. The organic electroluminescent device of this application will be described in detail below through embodiments. However, the following embodiments are merely examples of this application and are not intended to limit the scope of this application.

[0203] Example 1: Red Organic Electroluminescent Device

[0204] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0205] On the experimental substrate (anode), PD:HT-23 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-23 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The hole transport layer.

[0206] The compound HT-24 was vacuum-deposited on the first hole transport layer to form a thickness of [missing information]. Second hole transport layer

[0207] Next, on the second hole transport layer, compound Al:RH-N:RD was co-deposited at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer (EML)

[0208] On the light-emitting layer, compound ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0209] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP-1 was used to complete the fabrication of a red organic electroluminescent device.

[0210] Examples 2-36

[0211] Except that, when fabricating the light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compounds in Table 8 below were used instead of compound A1 in Example 1.

[0212] Comparative Examples 1-3

[0213] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound A1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0214] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0215]

[0216]

[0217] The performance of the red organic electroluminescent devices prepared in Examples 1-36 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0218] Table 8

[0219]

[0220]

[0221] Referring to Table 7 above, compared with Comparative Examples 1 to 3, using the compound of this application as the hole transport host material in the red light host material improves the luminous efficiency of the device by at least 11.0% and the lifetime by at least 18.3%.

[0222] The core group of the compound in this application consists of an aromatic ring of fused tetramethylcyclohexane linked to indolocarbazole. Indolocarbazole possesses a large conjugated area, endowing the compound with excellent hole transport properties. The fusion of the tetramethylcyclohexane structure with a benzene ring or a dibenzo5-membered ring further enhances the hole transport capability of the carbide compound through a hyperconjugation effect. Furthermore, the four methyl groups of tetramethylcyclohexane provide steric hindrance, allowing for precise control of intermolecular packing and enabling the formation of a good amorphous thin film. When the compound of this application is used as a hole transport material in the luminescent layer, it can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance the luminous efficiency and lifetime of the device. In particular, when the aromatic ring of fused tetramethylcyclohexane is directly linked to indolocarbazole, the organic electroluminescent device exhibits high luminous efficiency while maintaining a low voltage. When the aromatic ring of fused tetramethylcyclohexane is linked to indobenzocarbazole via a non-single bond, organic electroluminescence exhibits a long lifespan while maintaining a low voltage.

[0223] It should be understood that this application is not limited to the precise structure described above and shown in the accompanying drawings, and various modifications and changes can be made without departing from its scope. The scope of this application is limited only by the appended claims.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1. Formula 1 Wherein, ring A is selected from benzene ring, dibenzofuran ring, dibenzothiophene ring or dimethylfluorene ring; Ring C, ring B, and ring D may be the same or different, and are independently selected from benzene rings or naphthalene rings; L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or substituted biphenylene; The substituents in L1 and L2 may be the same or different, and are independently selected from deuterium or phenyl; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl; The substituents in Ar may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl or phenyl; If R1, R2, or R3 are the same, then deuterium is selected. n1 represents the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, any two R1s are the same or different. n2 represents the number of substituents R2, and n2 is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, any two R2s are the same or different. n3 represents the number of substituents R3, and n3 is selected from 0, 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 1-9, formula 1-10, formula 1-11, formula 1-12, formula 1-13, formula 1-14, formula 1-15, formula 1-16, formula 1-17, formula 1-18, formula 1-19, formula 1-20, formula 1-21, formula 1-22, formula 1-23, formula 1-24 or formula 1-25:

3. The organic compound according to claim 1, characterized in that, Selected from the group consisting of the following groups: 。 4. The organic compound according to claim 1, characterized in that, Selected from the group consisting of the following groups: 。 5. An organic compound, characterized in that, The organic compound is selected from the group consisting of the following compounds: 。 6. An organic electroluminescent device, characterized in that, It includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains an organic compound as described in any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The functional layer includes an organic light-emitting layer, which contains the organic compound.

8. The organic electroluminescent device according to claim 6, characterized in that, The organic electroluminescent device is a red organic electroluminescent device.

9. An electronic device, characterized in that, The organic electroluminescent device included in any one of claims 6 to 8.

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