Organic compound, and electronic element and electronic device in which same is used

Abstract

The present application relates to an organic compound, and an electronic element and an electronic device in which same is used. The organic compound has a structure represented by formula (1), and can significantly improve the performance of an organic electroluminescent device when used in the device.

Description

Organic compounds and electronic components and devices using them

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese patent application No. CN202410488984.6, filed on April 22, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application relates to the field of organic electroluminescence technology, and more specifically, to an organic compound and electronic components and devices using the same. Background Technology

[0004] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

[0005] Taking an organic light-emitting diode (OLED) device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer (serving as an energy conversion layer), an electron transport layer, and a cathode, which are stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light.

[0006] Although existing technologies disclose materials that can be used in organic electroluminescent devices, it remains necessary to continue developing new materials to further improve the performance of electronic components. Summary of the Invention

[0007] The purpose of this application is to provide an organic compound and electronic components and devices using the same, wherein using the organic compound in an organic electroluminescent device can improve the device's performance.

[0008] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0009] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2.

[0010] Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0011] L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0012] The substituents in L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

[0013] A second aspect of this application provides an electronic component 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 comprising the aforementioned organic compound.

[0014] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0015] The organic compounds in this application are triarylamine compounds with a benzene ring as the core. The nitrogen atom of the aromatic amine is directly attached to position 1, while triphenylene or other aromatic groups are attached to positions 2 and 3. The large planar conjugation of the triphenylene adjusts the spatial configuration of the molecule, increasing the glass transition temperature (Tg) of the material. Connecting the triphenylene to the aromatic amine group via a phenyl group also effectively improves the hole mobility of the molecule and lowers the barrier for carrier injection into the organic light-emitting layer, thereby improving the luminous efficiency of the device. Furthermore, the attachment of consecutive adjacent substituents to the central phenyl group increases the spatial distortion of the molecule, raising the glass transition temperature and ensuring the formation of a stable amorphous thin film during evaporation, thus extending the device's lifespan. Therefore, using the organic compound of this application as a hole transport material can significantly improve the luminous efficiency and lifespan of the device.

[0016] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0017] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0018] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0019] Figure 2 is a schematic diagram of a first electronic device according to one embodiment of this application.

[0020] Figure 3 is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0021] Figure 4 is a schematic diagram of a second electronic device according to one embodiment of this application.

[0022] Explanation of reference numerals in the attached figures: 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. Detailed Implementation

[0023] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of 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. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0024] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0025] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2.

[0026] Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0027] L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0028] The substituents in L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

[0029] In this application, the descriptive phrases "each independently selected from" and "separately independently selected from" 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.

[0030] 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, halogen groups, cyano, alkyl, trialkylsilyl, haloalkyl, cycloalkyl, aryl, heteroaryl, etc.

[0031] 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.

[0032] 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 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 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, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in this application, biphenyl, terphenyl, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0033] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiopheneyl-substituted phenyl, pyridyl-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0034] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom. The heteroatom can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner. Any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0035] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0036] In this application, the aryl group used as a substituent can have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and anthraceneyl groups. base.

[0037] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0038] 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, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, and 3,7-dimethyloctyl.

[0039] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0040] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0041] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0042] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0043] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can be connected to any position in the ring system it traverses, 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 via two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0044] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0045] In some embodiments of this application, the organic compound has the structure shown in Formula I-1, Formula I-2, or Formula I-3:

[0046] The definitions of L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 in Equation I-1, Equation I-2, or Equation I-3 are the same as those in Equation 1.

[0047] In some embodiments of this application, L1, L2, L3, and L4 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. For example, L1, L2, L3, and L4 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0048] Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms or phenyl.

[0049] In some embodiments of this application, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0050] Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0051] In some embodiments of this application, L1, L2, L3, and L4 may be the same or different, and each is independently selected from single bonds or the following groups:

[0052] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0053] In some embodiments of this application, L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0054] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2. For example, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2.

[0055] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, haloalkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, deuterylalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

[0056] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2.

[0057] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0058] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0059] And at least one of Ar1 and Ar2 is selected from

[0060] In some embodiments of this application, Ar1 is selected from the group consisting of:

[0061] And Ar2 is selected from

[0062] In some embodiments of this application, Ar2 is selected from the group consisting of:

[0063] And Ar1 is selected from

[0064] In some embodiments of this application, Ar1 is selected from the group consisting of:

[0065] And Ar2 is selected from

[0066] In some embodiments of this application, Ar2 is selected from the group consisting of:

[0067] And Ar1 is selected from

[0068] In some embodiments of this application, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0069] Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

[0070] In some embodiments of this application, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted cyclopentanespirofluorenyl, substituted or unsubstituted cyclohexanespirofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoleyl.

[0071] Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0072] In some embodiments of this application, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted groups V; wherein, the unsubstituted group V is selected from the following groups:

[0073] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0074] In some embodiments of this application, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0075] In some embodiments of this application, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0076] In some embodiments of this application, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0077] In some embodiments of this application, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0078] Specifically, the organic compound is selected from the group consisting of:

[0079] Secondly, this application provides an electronic component, 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 contains the organic compound of this application.

[0080] Optionally, the functional layer includes a hole transport layer, which contains the organic compound.

[0081] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0082] Optionally, the organic electroluminescent device is a red-light organic electroluminescent device.

[0083] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is closer to the anode than the second hole transport layer, and the second hole transport layer contains the organic compound of this application.

[0084] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200 stacked together. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0085] Optionally, the anode 100 comprises an anode material, preferably one with a high 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, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0086] Optionally, the hole transport layer includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not specify any particular type of material. For example, the material of the first hole transport layer may be selected from the group consisting of the following compounds:

[0087] In one specific embodiment, the first hole transport layer 321 is HT-1; the second hole transport layer 322 is the compound of this application.

[0088] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 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.

[0089] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special limitations on this. The host material can be a single host material or a mixture of host materials. In one embodiment of this application, the host material of the organic light-emitting layer 330 is RH.

[0090] The guest material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0091] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is Ir(piq)2(acac).

[0092] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material can be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as Bphen, NBphen, ET-20, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazo aryl groups as shown below.

[0093] In one embodiment of this application, the electron transport layer 340 is composed of ET-20 and LiQ.

[0094] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layer. 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. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0095] Optionally, as shown in Figure 1, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can 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. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0096] In one specific embodiment of this application, the hole injection layer 310 is F4-TCNQ.

[0097] Optionally, as shown in Figure 1, an electron injection layer 350 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 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes Yb.

[0098] In another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in this application.

[0099] According to one specific embodiment, as shown in FIG3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200 stacked sequentially. Optionally, the hole transport layer 320 comprises the organic compound of this application.

[0100] Optionally, the photoelectric conversion device can be a solar cell, especially an organic thin-film solar cell. For example, in one embodiment of this application, the solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked sequentially, wherein the hole transport layer contains the organic compound of this application.

[0101] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0102] According to one embodiment, as shown in FIG2, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0103] In another embodiment, as shown in FIG4, the electronic device is a second electronic device 500, which includes the aforementioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a photosensor, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0104] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0105] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0106] Synthesis example

[0107] 1. Synthesis of intermediate IM a:

[0108] 1-Bromo-3-chloro-2-iodobenzene (30 g, 94.53 mmol), triphenyl-2-boronic acid (25.72 g, 94.53 mmol), bis(triphenylphosphine) palladium dichloride (0.33 g, 0.47 mmol), and potassium carbonate (32.66 g, 236.33 mmol) were added to a flask, along with a mixed solvent of toluene (240 mL) and water (60 mL). Under nitrogen protection, the mixture was heated to 70-75 °C and stirred for 6 h until the reaction was complete. The mixture was then cooled to room temperature, stirring was stopped, the reaction solution was washed with water, extracted with dichloromethane, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain intermediate IM a (23.69 g, 60% yield) as a white solid.

[0109] Intermediate IMx (x being b to j) listed in Table 1 was prepared using the same method as intermediate IMa, except that starting material 1 was used instead of triphenyl-2-boronic acid. The main starting materials used, the intermediates synthesized, and their yields are shown in Table 1.

[0110] Table 1

[0111] 2. Synthesis of intermediate IM a':

[0112] IM a (12 g, 28.73 mmol), phenylboronic acid (3.50 g, 28.72 mmol), bis(triphenylphosphine)palladium dichloride (0.10 g, 0.14 mmol), and potassium carbonate (9.93 g, 71.82 mmol) were added to a flask, along with a mixed solvent of toluene (240 mL) and water (60 mL). Under nitrogen protection, the mixture was heated to 75-85 °C and stirred for 6 h until the reaction was complete. The mixture was then cooled to room temperature, stirring was stopped, the reaction solution was washed with water, extracted with toluene, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by recrystallization using dichloromethane / n-heptane to obtain IM a' (9.54 g, 80% yield) as a white solid.

[0113] Intermediate IMx' (x is b to s) listed in Table 2 was prepared using the same method as intermediate IMa', except that starting material 2 was used instead of IMa and starting material 3 was used instead of phenylboronic acid. The main starting materials used, the intermediates synthesized, and their yields are shown in Table 2.

[0114] Table 2

[0115] Synthesis Example 1: Synthesis of Compound 1

[0116] IM a' (12.0 g, 28.9 mmol), reactant A (10.45 g, 28.9 mmol), sodium tert-butoxide (4.17 g, 43.4 mmol), tris(dibenzylacetone)dipalladium (0.26 g, 0.29 mmol), 2-bis(dicyclohexylphosphine-2',6'-dimethoxybiphenyl) (0.27 g, 0.58 mmol), and xylene (120 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred and heated to 120-130 °C for 5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was washed with water and ethanol and dried to obtain the crude product. The crude product was purified by recrystallization from toluene to give compound 1 (11.13 g, yield 52%) as a white solid. Mass spectrometry (m / z) = 740.3 [M+H] + .

[0117] The compounds listed in Table 3 were prepared using the same method as compound 1, except that reactant 4 was used instead of IM a' and reactant 5 was used instead of reactant A. The main reactants used, the synthesized compounds, their yields, and mass spectra are shown in Table 3.

[0118] Table 3

[0119] NMR data for some compounds are shown in Table 4 below.

[0120] Table 4

[0121] Example 1: Red Organic Electroluminescent Device

[0122] The anode is prepared through the following process: A thickness of [missing information] is [missing information]. The ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). It was then prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was then treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove slag.

[0123] On the experimental substrate (anode), compound F4-TCNQ was deposited by vapor deposition to form a thickness of [missing information]. Hole injection layer.

[0124] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The first hole transport layer.

[0125] Compound 1 is deposited on the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0126] On the second hole transport layer, compounds RH and Ir(piq)₂(acac) were vapor-deposited at a thickness ratio of 95%:5% to form a film with a thickness of [missing information]. The organic light-emitting layer.

[0127] On the organic light-emitting layer, ET-20 and LiQ were vapor-deposited at a 1:1 film thickness ratio to form a film with a thickness of [missing information]. The electron transport layer.

[0128] Subsequently, LiQ was deposited onto the electron transport layer to form a thickness of [thickness value missing]. An electron-injected layer is formed, and then magnesium (Mg) and silver (Ag) are vapor-deposited onto the electron-injected layer at a thickness ratio of 1:9 to form a film with a thickness of [missing information]. The cathode.

[0129] Furthermore, compound CP-1 is deposited on the aforementioned cathode to form a thickness of [missing information]. The covering layer is used to complete the fabrication of the organic light-emitting device.

[0130] Examples 2 to 29

[0131] Except that, when preparing the second hole transport layer, the organic electroluminescent device was fabricated using the same method as in Example 1, except that the compound in Table 5 was used instead of compound 1 in Example 1.

[0132] Comparative Examples 1 to 3

[0133] Except that when preparing the second hole transport layer, compounds A, B, and C were used instead of compound 1 in Example 1, the organic electroluminescent device was fabricated using the same method as in Example 1.

[0134] The compounds used in preparing the devices of the above embodiments and comparative examples have the following structures:

[0135] The performance of the red organic electroluminescent devices prepared in Examples 1 to 29 and Comparative Examples 1 to 3 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifespan of T95 was tested under the following conditions, and the test structure is shown in Table 5 below.

[0136] Table 5

[0137] According to the results in Table 5 above, compared with the organic electroluminescent devices of Comparative Examples 1 to 3, the organic electroluminescent devices of Examples 1 to 29 have significantly improved performance, with luminous efficiency increased by at least 12.4% and T95 lifetime increased by at least 11.3%.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2. Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. The substituents in L1, L2, L3, L4, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 3 to 20 carbon atoms.

2. The organic compound according to claim 1, wherein, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms or phenyl.

3. The organic compound according to claim 1 or 2, wherein, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl. Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

4. The organic compound according to any one of claims 1 to 3, wherein, L1, L2, L3, and L4 may be the same or different, and each is independently selected from a single bond or one of the following groups:

5. The organic compound according to any one of claims 1 to 4, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, haloalkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, deuterylalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

6. The organic compound according to any one of claims 1 to 5, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, or the structure shown in Formula 2, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

7. The organic compound according to any one of claims 1 to 6, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of the following groups: And at least one of Ar1 and Ar2 is selected from 8. The organic compound according to any one of claims 1 to 7, wherein, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

9. The organic compound according to any one of claims 1 to 8, wherein, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted cyclopentanespirofluorenyl, substituted or unsubstituted cyclohexanespirofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar3 and Ar4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

10. The organic compound according to any one of claims 1 to 9, wherein, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of the following groups:

11. The organic compound according to any one of claims 1 to 10, wherein, The organic compound is selected from the group consisting of the following compounds:

12. An electronic component, characterized in that, The electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises an organic compound as described in any one of claims 1 to 11.

13. The electronic component according to claim 12, wherein, The functional layer includes a hole transport layer, and the hole transport layer contains the organic compound; Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device; Alternatively, the organic electroluminescent device may be a red-light organic electroluminescent device.

14. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 12 or 13.

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