Organic compound, and electronic element and electronic device using same
By using an organic compound with a 13H-benzo[2,3]benzofuran/benzothiophene[7,6-d]benzo[4,5]imidazole as the parent nucleus as the blue light host material, the shortcomings of organic electroluminescent devices in terms of lifetime and efficiency are solved, and the performance of the device is improved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-09-11
- Publication Date
- 2026-03-13
AI Technical Summary
Existing organic electroluminescent devices have shortcomings in terms of lifespan and efficiency, especially in large-area display devices where the driving voltage is high, and the luminous efficiency and current efficiency need to be improved.
An organic compound is used as a hybrid blue light host material, with a structure of 13H-benzo[2,3]benzofuran/benzothiophene[7,6-d]benzo[4,5]imidazole as the parent core. By connecting aryl groups, the molecules are placed in different planes, which increases the glass transition temperature. It is used in combination with an electron transport host material to avoid the spectral redshift caused by the formation of excitocomplexes.
This improves the lifetime and luminous efficiency of organic electroluminescent devices and reduces the problem of poor luminous efficiency caused by low energy transfer efficiency between the host material and the dopant material.
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Figure CN121652162A_ABST
Abstract
Description
Technical Field
[0001] This application relates to the field of organic electroluminescence technology, specifically to an organic compound and electronic components and devices using the same. Background Technology
[0002] 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 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. 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.
[0003] Generally speaking, in a host material / dopant system, the choice of host material is crucial because it significantly impacts the efficiency and lifetime of the light-emitting device. A high-performance host material should possess a suitable molecular weight, high glass transition temperature and thermal decomposition temperature, high electrochemical stability, and good interfacial contact with adjacent functional layer materials. For blue light-emitting host materials, good carrier transport capability and a suitable triplet energy level are required to ensure efficient energy transfer from the host material to the guest material during light emission, thereby achieving high device efficiency.
[0004] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention
[0005] 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.
[0006] A first aspect of this application provides an organic compound having the structure shown in Formula 1:
[0007]
[0008] Where X is selected from O or S;
[0009] Ar cSelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
[0010] Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterylaryl with 6 to 20 carbon atoms;
[0011] L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and heteroaryl groups with 3 to 30 carbon atoms;
[0012] Ar is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0013] The substituents in L and Ar may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;
[0014] R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuteratedaryl with 6 to 12 carbon atoms.
[0015] n1 is the number of R1s, and n1 is selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.
[0016] n2 is the number of R2, and n1 is selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different.
[0017] n3 is the number of R3s, which can be selected from 0, 1, 2 or 3. When n3 is greater than 1, any two R3s are the same or different.
[0018] 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.
[0019] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.
[0020] The compound structure of this application contains 13H-benzo[2,3]benzofuran / benzothiophene[7,6-d]benzo[4,5]imidazol[1,2-a]imidazol. The structure of this compound features a parent core with aryl groups attached to the benzene ring of benzofuran / benzothiophene, resulting in the entire molecule being in different planes and exhibiting high overall molecular distortion. This leads to a high glass transition temperature, thus improving device lifetime when the compound is used as a hole transport material in a hybrid blue light host material. Furthermore, due to the good steric morphology of this molecule, when used in conjunction with an electron transport host material, it avoids the spectral redshift caused by the formation of excitocomplexes, thereby preventing poor luminous efficiency due to low energy transfer efficiency in both the host and dopant materials.
[0021] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description
[0022] 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.
[0023] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0024] Figure 2 This is a schematic diagram of a first electronic device according to one embodiment of this application.
[0025] Explanation of reference numerals in the attached figures
[0026] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer 321, Hole Transport Layer
[0027] 322, Electron blocking layer; 330, Organic light-emitting layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device. Detailed Implementation
[0028] 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.
[0029] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:
[0030]
[0031] Where X is selected from O or S;
[0032] Ar c Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
[0033] Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterylaryl with 6 to 20 carbon atoms;
[0034] L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and heteroaryl groups with 3 to 30 carbon atoms;
[0035] Ar is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0036] The substituents in L and Ar may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;
[0037] R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuteratedaryl with 6 to 12 carbon atoms.
[0038] n1 is the number of R1s, and n1 is selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.
[0039] n2 is the number of R2, and n1 is selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different.
[0040] n3 is the number of R3s, which can be selected from 0, 1, 2 or 3. When n3 is greater than 1, any two R3s are the same or different.
[0041] 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.
[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, halogen groups, cyano, alkyl, trialkylsilyl, haloalkyl, triphenylsilyl, deuterated alkyl, aryl, heteroaryl, deuterated aryl, etc.
[0043] 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 L is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.
[0044] 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.
[0045] 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, haloalkyl, deuteryl, triphenylsilyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-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.
[0046] 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.
[0047] 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, haloalkyl, deuteryl, triphenylsilyl, 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.
[0048] 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.
[0049] 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.
[0050] In this application, the number of carbon atoms in alkyl groups having 1 to 10 carbon atoms 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, 3,7-dimethyloctyl, etc.
[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, triethylsilyl, etc.
[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, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects 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 traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.
[0056]
[0057] 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.
[0058]
[0059] In some embodiments of this application, L is selected from substituted or unsubstituted aryl groups with a single bond and 6 to 18 carbon atoms. For example, L is selected from substituted or unsubstituted aryl groups with a single bond and 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0060] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, alkyl, phenyl or pentadeuterated phenyl with 1 to 5 carbon atoms.
[0061] In some embodiments of this application, L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.
[0062] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
[0063] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:
[0064]
[0065] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:
[0066]
[0067] In some embodiments of this application, Ar is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
[0068] Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, haloalkyl with 1 to 5 carbon atoms, deuteryl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuteryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.
[0069] In some embodiments of this application, Ar is 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, and substituted or unsubstituted carbazoyl.
[0070] Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
[0071] In some embodiments of this application, Ar is selected from the group consisting of:
[0072]
[0073] In some embodiments of this application, Ar is selected from the group consisting of:
[0074]
[0075] In some embodiments of this application, Selected from the group consisting of the following groups:
[0076]
[0077]
[0078] In some embodiments of this application, Selected from the group consisting of the following groups:
[0079]
[0080] In some embodiments of this application, Ar c Selected from substituted or unsubstituted aryl groups having 6 to 24 carbon atoms. For example, Ar c Selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.
[0081] Optionally, Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.
[0082] In some embodiments of this application, Ar c 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 triphenylene, substituted or unsubstituted phenanthrene.
[0083] Optionally, Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
[0084] In some embodiments of this application, Ar c Selected from the group consisting of the following groups:
[0085]
[0086] In some embodiments of this application, Ar c Selected from the group consisting of the following groups:
[0087]
[0088] In some embodiments of this application, R1, R2 and R3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl or pentadeuterated phenyl.
[0089] In the organic compounds of this application, When ortho-biphenyl groups, whether substituted or unsubstituted, are used as the p-type host of organic light-emitting devices (OLEDs), the OLEDs exhibit higher efficiency and lifetime. This is because introducing ortho-biphenyl groups into the host nucleus provides better stereochemistry, reducing the formation of exciton complexes, thereby minimizing the redshift in the blue light host spectrum, improving energy transfer efficiency between the host and guest, and ultimately enhancing the device's luminous efficiency and lifetime.
[0090] In some embodiments of this application, the organic compound is selected from the group consisting of:
[0091]
[0092]
[0093]
[0094]
[0095] 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.
[0096] Optionally, the functional layer includes an organic light-emitting layer, which contains the organic compounds described in this application.
[0097] Optionally, the electronic component is an organic electroluminescent device.
[0098] In one embodiment, the electronic component is an organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200, which are stacked sequentially.
[0099] In one specific implementation, the organic electroluminescent device is a blue organic electroluminescent device.
[0100] Optionally, the anode 100 includes an anode material that is preferably a material 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.
[0101] Optionally, the hole transport layer 321 includes one or more hole transport materials. The hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can select these materials by referring to existing technologies. For example, the material of the hole transport layer is selected from the group consisting of the following compounds:
[0102]
[0103] In one specific implementation, the hole transport layer 321 is HT-5.
[0104] Optionally, the electron blocking layer 322 comprises one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds; this application does not impose any special limitations on this. In one specific embodiment, the electron blocking layer 330 is EB-1.
[0105] 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 dopant material. Optionally, the organic light-emitting layer 330 is composed of a host material and a dopant 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 dopant material, thereby enabling the dopant material to emit light.
[0106] 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 restrictions on this. The host material can be a single host material or a mixture of host materials.
[0107] In one embodiment of this application, the host material of the organic light-emitting layer 330 is compound BH. And the organic compounds of this application.
[0108] The doping material for the organic light-emitting layer 330 can be selected according to existing technologies, such as iridium(III) organometallic complexes, platinum(II) organometallic complexes, ruthenium(II) complexes, etc. Specific examples of doped materials include, but are not limited to,
[0109]
[0110] In one embodiment of this application, the doping material of the organic light-emitting layer 330 is BD.
[0111] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complexes may be selected from, for example, LiQ, Alq3, Bepq2, etc. The nitrogen-containing heterocyclic derivatives may be aromatic rings with a nitrogen-containing six- or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six- or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as ET-21, Bphen, NBphen, DBimiBphen, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteronitrogenous aryl groups as shown below. In one embodiment of this application, the electron transport layer 340 is composed of ET-21 and LiQ.
[0112]
[0113] 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.
[0114] Optionally, such as Figure 1 As shown, a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. 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. For example, the compounds contained in the hole injection layer 310 may be selected from the group consisting of the following compounds:
[0115]
[0116] In one specific embodiment of this application, the hole injection layer 310 is HT-5 and P-dopant.
[0117] Optionally, such as Figure 1 As shown, 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. In one specific embodiment of this application, the electron injection layer 350 is Yb.
[0118] A third aspect of this application provides an electronic device that includes the electronic components provided in the second aspect of this application.
[0119] According to one implementation method, such as Figure 2 As shown, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first 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, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. The synthesis method of the organic compounds in this application will be specifically described below with reference to synthesis examples, but this application is not limited thereto.
[0120] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.
[0121] 1. Synthesis of intermediate Sub-a1:
[0122]
[0123] To a 2L round-bottom flask, 2-aminobenzimidazole (50.00 g, 375.51 mmol), 2-fluorobiphenyl (71.13 g, 413.06 mmol), potassium phosphate (239.12 g, 1.13 mol), and N-methylpyrrolidone (1 L) were added sequentially. The mixture was heated to approximately 160 °C and stirred until the 2-aminobenzimidazole was completely consumed. After the system cooled to room temperature, the reaction mixture was poured into 1 L of deionized water. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate (500 mL × 3). The organic phases were then combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as eluent, finally yielding the intermediate Sub-a1 (76.20 g, yield: 71%) as a white solid.
[0124] The intermediate Sub-ax (x is 2 to 4) shown in Table 1 was synthesized using the same method as intermediate Sub-a1, except that reactant A was used instead of RM-1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 1.
[0125] Table 1
[0126]
[0127]
[0128] 2. Synthesis of intermediate Sub-a5:
[0129]
[0130] Add 2-aminobenzimidazole (50.00 g, 375.51 mmol), (3-bromophenyl)triphenylsilane (171.59 g, 413.06 mmol), cesium phosphate (305.87 g, 938.76 mmol), 8-hydroxyquinoline (1.09 g, 7.51 mmol), and tert-butanol (1 L) sequentially to a 2 L round-bottom flask. Heat to approximately 80 °C and add cuprous iodide (0.72 g, 3.76 mmol). Reheat to reflux and stir until the 2-aminobenzimidazole has completely reacted. After the system cools to room temperature, pour the reaction mixture into 1 L of deionized water. Separate the organic phase and extract the aqueous phase with ethyl acetate (500 mL × 3). Combine the organic phases, dry with anhydrous sodium sulfate, filter, and remove the solvent by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as eluent, and the final product was Sub-a5 (51.60 g, yield: 48%) as a white solid.
[0131] The intermediate Sub-ax (x is 6 to 11) shown in Table 2 was synthesized using the same method as Sub-a5, except that reactant B was used instead of RM-2. The main raw materials used, the intermediates synthesized and their yields are shown in Table 2.
[0132] Table 2
[0133]
[0134]
[0135] 3. Synthesis of intermediate Sub-b1:
[0136]
[0137] RM-3 (51.00 g, 243.73 mmol), 3-bromo-2-fluoroanisole (54.97 g, 268.10 mmol), cesium carbonate (198.53 g, 609.31 mmol), and N,N-dimethylacetamide (1 L) were added sequentially to a 2 L three-necked flask. The mixture was stirred at room temperature until RM-3 was completely consumed, and then the temperature was raised to 120 °C and the reaction was continued for approximately 16 h. After the system temperature cooled to room temperature, the reaction solution was poured into 1 L of deionized water and stirred until no more solid precipitated. The mixture was then filtered, and the crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the eluent, finally yielding Sub-b1 (53.20 g, yield: 70%) as a white solid.
[0138] The intermediate Sub-bx (x is 2 to 17) shown in Table 3 was synthesized using the same method as Sub-b1, except that reactant C was used instead of RM-3 and reactant D was used instead of RM-4. The main raw materials used, the intermediates synthesized and their yields are shown in Table 3.
[0139] Table 3
[0140]
[0141]
[0142]
[0143] 4. Synthesis of intermediate Sub-c1:
[0144]
[0145] Boron tribromide (13.00 g, 51.86 mmol) was added dropwise to a 600 mL solution of Sub-b1 (32.50 g, 103.71 mmol) in dichloromethane, and the mixture was stirred at room temperature until Sub-b1 was completely consumed. The reaction was then quenched with a saturated aqueous sodium bicarbonate solution, and the aqueous phase was extracted with DCM (200 mL × 3) after separation. The organic phases were then combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as eluent, finally yielding a white solid, Sub-c1 (27.90 g, yield: 90%).
[0146] The intermediate Sub-cx (x is 2 to 17) shown in Table 4 was prepared by referring to the synthesis method of Sub-c1, except that reactant E was used instead of Sub-b1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 4.
[0147] Table 4
[0148]
[0149]
[0150]
[0151] 5. Synthesis of intermediate Sub-d1:
[0152]
[0153] Sub-c1 (27.20 g, 90.87 mmol), RM-5 (24.80 g, 90.87 mmol), cesium carbonate (74.02 g, 227.17 mmol), 2,2,6,6-tetramethyl-3,5-heptadecyl dione (13.40 g, 72.69 mmol), and N,N-dimethylformamide (500 mL) were added sequentially to a 1 L three-necked flask. The mixture was heated to approximately 100 °C under an argon atmosphere, followed by the addition of cuprous bromide (1.30 g, 9.09 mmol). The mixture was then heated to reflux, and the reaction was stirred until Sub-c1 was completely consumed. After the system cooled to room temperature, the reaction mixture was poured into 1 L of deionized water. The aqueous phase was then extracted with ethyl acetate (500 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by filtration and distillation under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as eluent, and finally a white solid Sub-d1 (32.60 g, yield: 81%) was obtained.
[0154] The intermediate Sub-dx (x is 2 to 27) shown in Table 5 was prepared by referring to the synthesis method of Sub-d1. The difference is that reactant F was used instead of Sub-c1 and reactant G was used instead of RM-5. The main raw materials used, the intermediates synthesized and their yields are shown in Table 5.
[0155] Table 5
[0156]
[0157]
[0158]
[0159]
[0160] 6. Synthesis of intermediate Sub-e1:
[0161]
[0162] Sub-d1 (30.10 g, 61.58 mmol), potassium phosphate (39.22 g, 184.75 mmol), 1,3-bis(2,6-diisopropylphenyl)chloroimidazolam (2.62 g, 6.16 mmol), and N,N-dimethylacetamide (500 mL) were added sequentially to a 1 L three-necked flask. The mixture was heated to approximately 100 °C under an argon atmosphere, followed by the addition of palladium acetate (691 mg, 3.08 mmol), and the mixture was heated to reflux. The reaction mixture was stirred until Sub-d1 was completely consumed. After the system cooled to room temperature, the reaction mixture was poured into 1 L of deionized water. The aqueous phase was then extracted with ethyl acetate (500 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The mixture was filtered and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as the eluent, finally yielding a white solid, Sub-e1 (16.20 g, yield: 64%).
[0163] The intermediate Sub-ex (x is 2 to 17) shown in Table 6 was prepared by referring to the synthesis method of Sub-e1, except that reactant H was used instead of Sub-d1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 6.
[0164] Table 6
[0165]
[0166]
[0167]
[0168]
[0169] 7. Synthesis of intermediate Sub-f1:
[0170]
[0171] Sub-e3 (13.70 g, 24.34 mmol), RM-6 (4.82 g, 24.34 mmol), potassium carbonate (11.26 g, 73.02 mmol), triphenylphosphine (262 mg, 1.0 mmol), acetonitrile (150 mL), and deionized water (50 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to approximately 60 °C under an argon atmosphere, followed by the addition of palladium acetate (113 mg, 0.5 mmol), and the mixture was heated to reflux. The reaction was stirred until Sub-e1 was completely consumed. After the system cooled to room temperature, the aqueous phase was extracted with ethyl acetate (100 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation after filtration. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as the eluent, finally yielding a white solid Sub-f1 (12.60 g, yield: 81%).
[0172] The intermediate Sub-fx (x is 2 to 8) shown in Table 3 was prepared by referring to the synthesis method of Sub-f1. The difference is that reactant I was used instead of Sub-e1 and reactant J was used instead of RM-6. The main raw materials used, the intermediates synthesized and their yields are shown in Table 7.
[0173] Table 7
[0174]
[0175]
[0176] Synthesis Example 1: Synthesis of Compound 1:
[0177]
[0178] Sub-e1 (8.90 g, 21.82 mmol), RM-6 (4.32 g, 21.82 mmol), potassium carbonate (10.09 g, 65.46 mmol), triphenylphosphine (262 mg, 1.0 mmol), acetonitrile (200 mL), and deionized water (60 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to approximately 60 °C under an argon atmosphere, followed by the addition of palladium acetate (113 mg, 0.5 mmol), and the mixture was heated to reflux. The reaction was stirred until Sub-e1 was completely consumed. After the system cooled to room temperature, the aqueous phase was extracted with ethyl acetate (100 mL × 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by vacuum distillation after filtration. The crude product was purified by silica gel column chromatography using petroleum ether / ethyl acetate as the eluent, finally yielding white compound 1 (9.60 g, yield: 84%), mass spectrometry (m / z) = 526.18 [M+H]. + .
[0179] The compounds shown in Table 8 were synthesized using the same method as compound 1, except that reactant I was used instead of Sub-e1 and reactant J was used instead of RM-7. The main raw materials used, the synthesized compounds, their mass spectra, and the yields are shown in Table 8.
[0180] Table 8
[0181]
[0182]
[0183]
[0184]
[0185] NMR of Compound 7: 1 H-NMR(400MHz,Methylene Chloride-d2)δppm 8.45(d,1H),7.88-7.84(m,2H),7.75(d,1H),7.66-7.64(m,3H),7.55-7.40(m,10H),7.36-7.30(m,4H),7.29-7.20(m,2H),7.14(t,4H).
[0186] NMR of Compound 10: 1 H-NMR(400MHz,Methylene Chloride-d2)δppm 8.46(d,1H),7.87(d,1H),7.77(d,2H),7.73-7.60(m,9H),7.53-7.11(m,24H).
[0187] Example 1: Blue Organic Electroluminescent Device
[0188] Anodizing pretreatment is performed through the following process: The thickness is sequentially... The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (height). Surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode. The surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.
[0189] On the aforementioned experimental substrate, compounds HT-5 and P-dopant were co-deposited at a deposition rate ratio of 98%:2% to form a thickness of [missing information]. Hole injection layer.
[0190] Compound HT-5 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.
[0191] Compound EB-1 was deposited on the hole transport layer to form a thickness of [thickness value missing]. The electron blocking layer.
[0192] On the electron blocking layer, compound 1 (P-type doped host), compound BH (N-type doped host), and compound BD were co-deposited at a deposition rate ratio of 60%:30%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.
[0193] On the organic light-emitting layer, compound ET-21 and LiQ were co-deposited at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. The electron transport layer.
[0194] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed; then, magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate ratio of 10%:90% to form a layer with a thickness of [missing information]. The cathode.
[0195] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The cathode capping layer is used to complete the fabrication of the blue organic electroluminescent device.
[0196] Examples 2-28:
[0197] Except that when preparing the organic light-emitting layer, compound 1 was replaced with the compounds in Table 9 below, the organic electroluminescent device was prepared using the same method as in Example 1.
[0198] Comparative Examples 1-3
[0199] Except that compound 1 was replaced with compounds A, B, and C when preparing the organic light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1.
[0200] The compounds used in preparing the devices of the above embodiments and comparative examples are shown below.
[0201]
[0202] The performance of the blue organic electroluminescent devices prepared in Examples 1-28 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the condition of 1000 nit brightness, and the T90 lifetime was tested. The test results are shown in Table 9 below.
[0203] Table 9
[0204]
[0205]
[0206] As shown in Table 9 above, in Examples 1-28, the compounds of this application were used as P-type host materials, and compared with Comparative Examples 1-3, the luminous efficiency was improved by at least 20.7% and the device lifetime was improved by at least 17.6%.
[0207] It is evident that using the organic compounds of this application in the P-type host of organic electroluminescent devices can significantly improve the luminous efficiency and device lifespan of organic electroluminescent devices.
[0208] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.
Claims
1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Where X is selected from O or S; Ar c Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterylaryl with 6 to 20 carbon atoms; L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and heteroaryl groups with 3 to 30 carbon atoms; Ar is selected from 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 L and Ar may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms; R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuteratedaryl with 6 to 12 carbon atoms. n1 is the number of R1s, and n1 is selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different. n2 is the number of R2, and n1 is selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different. n3 is the number of R3s, which can be selected from 0, 1, 2 or 3. When n3 is greater than 1, any two R3s are the same or different.
2. In the organic compound according to claim 1, L is selected from substituted or unsubstituted aryl groups with a single bond and 6 to 18 carbon atoms; Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, alkyl, phenyl or pentadeuterated phenyl with 1 to 5 carbon atoms.
3. The organic compound according to claim 1, wherein L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
4. In the organic compound according to claim 1, Ar is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms; Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, haloalkyl with 1 to 5 carbon atoms, deuteryl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuteryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.
5. The organic compound according to claim 1, wherein Ar is 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 carbazolyl. Optionally, the substituents in Ar may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
6. In the organic compound according to claim 1, Ar is selected from the group consisting of:
7. The organic compound according to claim 1, Ar c Selected from substituted or unsubstituted aryl groups having 6 to 24 carbon atoms; Optionally, Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, triphenylsilyl, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.
8. The organic compound according to claim 1, Ar c 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 triphenylene, substituted or unsubstituted phenanthrene; Optionally, Ar c The substituents in the group may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl or naphthyl.
9. The organic compound according to claim 1, Ar c Selected from the group consisting of the following groups:
10. The organic compound according to claim 1, wherein R1, R2 and R3 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl or pentadeuterated phenyl.
11. The organic compound according to claim 1, 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 an organic light-emitting layer, and the organic light-emitting layer contains the organic compound; Optionally, the electronic component is an organic electroluminescent device.
14. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 12 or 13.