Organic compound, and organic electroluminescent device and electronic apparatus comprising same
By using indole[3,2,1-jk]carbazole linked to phenanthroline compounds as electron transport materials, the lifespan and efficiency issues of organic electroluminescent devices in large-area displays were solved, achieving a reduction in driving voltage and an improvement in luminous efficiency.
Patent Information
- Application Number
- PCT/CN2025/089085
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-06-17
- Filing Date
- 2025-04-15
- Publication Date
- 2025-12-26
AI Technical Summary
Existing organic electroluminescent devices suffer from lifespan and efficiency issues in large-area displays. As voltage increases, improved materials are needed to enhance performance.
Compounds with indole[3,2,1-jk]carbazole linked to phenanthroline are used as electron transport or charge generation materials. They have a large conjugated plane and high bond energy, which improves electron mobility and matches the energy levels of adjacent layers, thereby reducing the driving voltage and improving luminescence efficiency and lifetime.
It effectively reduces the driving voltage of organic electroluminescent devices, improves luminous efficiency, and extends service life.
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Figure CN2025089085_26122025_PF_FP_ABST
Abstract
Description
Organic compounds and organic electroluminescent devices and electronic devices containing them
[0001] Cross-references to related applications
[0002] This application claims priority to Chinese patent application No. 2024107810516, filed on June 17, 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 an organic electroluminescent device and electronic apparatus containing the same. Background Technology
[0004] Currently, organic electroluminescent devices (OLEDs) are considered the next generation of display and lighting technology due to their advantages such as active light emission, high current efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. OLEDs typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons, in an excited state, release energy outward, causing the electroluminescent layer to emit light.
[0005] Organic light-emitting devices (OLEDs) can have various structures, such as single-layer and multilayer structures. A single-layer OLED contains only one light-emitting unit between the anode and cathode, while a multilayer OLED consists of multiple stacked light-emitting units. A single light-emitting unit typically includes at least one light-emitting layer, a hole transport layer, and an electron transport layer. Further, the light-emitting unit can include a hole injection layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. Between adjacent light-emitting units are charge generation layers (CGLs) for charge generation and movement. CGLs are constructed in a pn configuration, containing an n-type charge generation layer (n-CGL) and a p-type charge generation layer (p-CGL). The p-type material primarily generates holes, while the n-type material is generated by doping the electron transport layer material with a low work function metal.
[0006] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the voltage also increases. Therefore, it is necessary to continue developing new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention
[0007] To address the aforementioned problems, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device comprising the same, wherein the organic compound can be used in an organic electroluminescent device to improve the device's performance.
[0008] A first aspect of this application provides an organic compound having the structure shown in Formula 1:
[0009] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and R 11 One or two of the groups are selected from the groups shown in Formula 2, and the others may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or heteroaryl with 3 to 12 carbon atoms; or, any two adjacent substituents among the others form a saturated or unsaturated 6 to 14-membered ring;
[0010] L is 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;
[0011] The substituents in L 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, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.
[0012] Each R may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms (substituted or unsubstituted), and heteroaryl with 3 to 30 carbon atoms (substituted or unsubstituted).
[0013] The substituents in each R 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, or deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.
[0014] m represents the number of R groups, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R groups are the same or different; or any two adjacent R groups form a saturated or unsaturated 3 to 15-membered ring.
[0015] A second aspect of this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the aforementioned organic compound.
[0016] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.
[0017] The purpose of this application is to provide a compound of indole[3,2,1-jk]carbazole linked to phenanthroline, which possesses a large conjugated plane, high interatomic bond energy, and is conducive to solid-state stacking of molecules, exhibiting good thermodynamic stability. Furthermore, when used as an electron transport material or charge generation material, it exhibits good energy level matching with adjacent layers, which is beneficial for electron injection and migration, effectively reducing the driving voltage of organic electroluminescent devices. Simultaneously, the compound provided in this application has a high electron mobility, thereby improving the luminous efficiency of organic electroluminescent devices. Moreover, it can effectively complex with metals, and when used as a charge generation layer material, it can improve the efficiency of charge generation, thereby reducing the driving voltage, improving luminous efficiency, and extending the lifespan of organic electroluminescent devices.
[0018] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description
[0019] 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.
[0020] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0021] Figure 2 is a schematic diagram of the structure of an organic electroluminescent device according to another embodiment of this application.
[0022] Figure 3 is a schematic diagram of the structure of an electronic device according to one embodiment of this application.
[0023] Explanation of reference numerals: 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 321, Hole transport layer; 322, Electron blocking layer; 330, Organic light-emitting layer; 340, Electron transport layer; 350, Electron injection layer; 411, First hole transport layer; 412, First hole adjustment layer; 413, First organic light-emitting layer; 414, First electron transport layer; 421, n-type charge generation layer; 422, p-type charge generation layer; 431, Second hole transport layer; 432, Second hole adjustment layer; 433, Second organic light-emitting layer; 434, Second electron transport layer; 410, First light-emitting unit; 420, Charge generation layer; 430, Second light-emitting unit; 500, Electronic device. Detailed Implementation
[0024] 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.
[0025] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:
[0026] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and R 11 One or two of the groups are selected from the groups shown in Formula 2, and the others may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or heteroaryl with 3 to 12 carbon atoms; or, any two adjacent substituents among the others form a saturated or unsaturated 6 to 14-membered ring;
[0027] L is 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 L 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, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.
[0029] Each R may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms (substituted or unsubstituted), and heteroaryl with 3 to 30 carbon atoms (substituted or unsubstituted).
[0030] The substituents in each R 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, or deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.
[0031] m represents the number of R groups, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R groups are the same or different; or any two adjacent R groups form a saturated or unsaturated 3 to 15-membered ring.
[0032] "Any two adjacent substituents" can include two substituents on the same atom, or one substituent on each of two adjacent atoms; wherein, when two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to; when one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring.
[0033] 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.
[0034] 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. The number of substituents can be one or more.
[0035] In this application, the group can be a monovalent group or a polyvalent group formed by substitution.
[0036] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms.
[0037] 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. Base, etc.
[0038] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.
[0039] 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, 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.
[0040] 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.
[0041] 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.
[0042] 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.
[0043] 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.
[0044] 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.
[0045] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
[0046] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.
[0047] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
[0048] In this application, It refers to the chemical bond that connects with other groups.
[0049] 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.
[0050] 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.
[0051] In some embodiments of this application, in Equation 2 Selected from the group consisting of the following groups:
[0052] In some embodiments of this application, in Equation 2 Selected from the group consisting of the following groups:
[0053] In some embodiments of this application, in Equation 2 Selected from the group consisting of the following groups:
[0054] In some embodiments of this application, in Equation 2 Selected from the group consisting of the following groups:
[0055] In some embodiments of this application, each R may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, alkenyl with 2 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, substituted or unsubstituted aryl with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms. For example, each R is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl with 1, 2, 3, 4, or 5 carbon atoms. Haloalkyl groups having 1, 2, 3, 4, or 5 carbon atoms; deuteralkyl groups having 1, 2, 3, 4, or 5 carbon atoms; 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; and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0056] Optionally, the substituents in R may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, or deuteryl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms; or any two adjacent R may form an unsaturated 3 to 15-membered ring.
[0057] In some embodiments of this application, each R may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, trifluoromethyl, trideuterated methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl; or any two adjacent R form a saturated benzene ring, naphthyl ring, or phenanthyl ring.
[0058] Optionally, the substituents in R may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, or carbazolyl.
[0059] In some embodiments of this application, each R may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, trifluoromethyl, trideuterated methyl, or the following groups:
[0060] In some embodiments of this application, each R may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, or the following groups:
[0061] In some embodiments of this application, L is selected from single bonds, substituted or unsubstituted aryl groups having 6 to 16 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms. For example, L is selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
[0062] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.
[0063] In some embodiments of this application, L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted pyrene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene.
[0064] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, pyrimidinyl, pyrazinyl or pyridinyl.
[0065] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:
[0066] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:
[0067] In some embodiments of this application, Formula 2 is selected from the group consisting of:
[0068] In some embodiments of this application, Formula 2 is selected from the group consisting of:
[0069] In some embodiments of this application, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and R 11 One or two of the groups are selected from the groups shown in Formula 2, and the others may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, phenyl, naphthyl, biphenyl, triazine, pyrimidinyl, pyridinyl, dibenzofuranyl, dibenzothiophene, or any two adjacent substituents among the others form a benzene ring, a naphthyl ring or a phenanthrene ring.
[0070] Specifically, the organic compound is selected from the group consisting of:
[0071] Secondly, this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.
[0072] Optionally, the functional layer includes an electron transport layer, which contains the organic compound described in this application.
[0073] In one embodiment of this application, the structure of the organic electroluminescent device is shown in FIG1, including 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 includes a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, a light-emitting layer 330, an electron transport layer 340, and an electron injection layer 350, wherein the electron transport layer 340 contains the organic compound described in this application.
[0074] In this application, the anode 100 includes the following anode materials, preferably materials with a large work function that facilitate 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. Optionally, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.
[0075] In this application, the hole injection layer 310 can be selected from benzidine derivatives, starburst-like arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special restrictions on this. The material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof:
[0076] In one embodiment of this application, the hole injection layer 310 is composed of HT-1 and PD.
[0077] In some embodiments of this application, the hole transport material may be selected from triarylamine compounds or other types of compounds, and those skilled in the art can make such selections with reference to existing technologies. For example, the material of the hole transport layer is selected from the group consisting of the following compounds.
[0078] In one embodiment of this application, the material of the hole transport layer 321 comprises HT-1.
[0079] In one embodiment of this application, the electron blocking layer 322 comprises one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds, and this application does not specifically limit this. For example, in some embodiments of this application, the electron blocking layer 322 is compound EB-1.
[0080] Optionally, the light-emitting layer material can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, the organic light-emitting layer 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.
[0081] Optionally, the host material of the light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. The host material of the organic light-emitting layer 330 may 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 BH-1.
[0082] In one specific embodiment of this application, the guest material of the light-emitting layer 330 is BD-1.
[0083] In this application, 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 embodiment of this application, the electron injection layer 350 includes Yb.
[0084] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives, wherein the metal complex material can be selected from, for example, LiQ, Alq3, etc. In one embodiment of this application, the electron transport layer 340 is composed of the compound of this application and LiQ.
[0085] In this application, cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.
[0086] Furthermore, this application also provides another organic electroluminescent device as shown in FIG2, which includes an anode and a cathode, and a functional layer disposed between the anode and the cathode. The functional layer includes a first light-emitting unit, a second light-emitting unit, and a charge-generating layer; the charge-generating layer contains the organic compound described in this application. The organic electroluminescent device shown in FIG2 is hereinafter also referred to as a stacked organic electroluminescent device.
[0087] The stacked organic electroluminescent device shown in Figure 2 includes an anode 100, a cathode 200, a hole injection layer 310, an electron injection layer 350, a first light-emitting unit 410, a second light-emitting unit 430, and a charge-generating layer 420. The first light-emitting unit 410, the second light-emitting unit 430, and the charge-generating layer 420 are located between the cathode 100 and the anode 200. The charge-generating layer 420 is located between the first light-emitting unit 410 and the second light-emitting unit 430, and the charge-generating layer 420 contains the organic compound described in this application.
[0088] In one embodiment of this application, the first light-emitting unit 410 includes a first hole transport layer 411, a first hole adjustment layer 412, a first organic light-emitting layer 413, and a first electron transport layer 414; the second light-emitting unit 430 includes a second hole transport layer 431, a second hole adjustment layer 432, a second organic light-emitting layer 433, and a second electron transport layer 434.
[0089] In one embodiment of this application, the charge generation layer 420 includes an n-type charge generation layer (n-CGL) 421 and a p-type charge generation layer (p-CGL) 422. The n-type charge generation layer 421 provides electrons to the first electron transport layer 414 of the first light-emitting unit 410, and the p-type charge generation layer 422 provides holes to the second hole transport layer 431 of the second light-emitting unit 430. In one embodiment of this application, the n-type charge generation layer comprises the organic compound described in this application.
[0090] In one embodiment of this application, the n-type charge generation layer is composed of the organic compound and metal doping material described in this application. Optionally, the metal doping material is Li, Ca, Ag, Cs, or Yb.
[0091] In one embodiment of this application, the p-CGL layer includes HT-2 and PD.
[0092] In this application, the anode 100 includes an anode material, optionally comprising indium tin oxide (ITO).
[0093] In one embodiment of this application, the hole injection layer 310 is composed of HT-2 and PD.
[0094] In one embodiment of this application, the materials of the first hole transport layer 411 and the second hole transport layer 431 comprise HT-2.
[0095] In one embodiment of this application, the materials of the first hole adjustment layer 412 and the second hole adjustment layer 432 include HT-1.
[0096] In this application, the first organic light-emitting layer of the first light-emitting unit and the second organic light-emitting layer of the second light-emitting unit may each include the same or different host material and the same or different guest material.
[0097] In one specific embodiment of this application, the main material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RH-1.
[0098] In one specific embodiment of this application, the guest material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RD-1.
[0099] In one specific embodiment of this application, the materials of the first electron transport layer 414 and the second electron transport layer 434 contain ET-1. And LiQ.
[0100] In one embodiment of this application, the electron injection layer 350 comprises Yb.
[0101] In one specific embodiment of this application, the cathode 200 includes a cathode material comprising magnesium (Mg) and silver (Ag).
[0102] Thirdly, this application provides an electronic device including the organic electroluminescent device of the second aspect of this application.
[0103] According to one embodiment, as shown in FIG3, the provided electronic device is electronic device 500, which includes the aforementioned organic electroluminescent device. Electronic device 500 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.
[0104] The following synthetic examples illustrate the method for synthesizing the organic compounds of this application, but this application is not limited thereto.
[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 IMA-1
[0108] 2,9-Dibromo-1,10-phenanthroline (10 g, 29.6 mmol) and phenylboronic acid (3.61 g, 29.6 mmol) were dissolved in 80 mL of toluene, followed by the addition of tetrakis(triphenylphosphine)palladium (0.17 g, 0.148 mmol), K₂CO₃ (8.17 g, 59.2 mmol), 10 mL of ethanol, and 10 mL of water. The mixture was heated under reflux for 6 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was subjected to column chromatography with ethyl acetate:n-heptane = 1:9 (v / v) to give intermediate IMA-1 (4.4 g, yield: 44%).
[0109] Intermediate IMA-X (X is 2 to 9) was prepared using the same synthesis as intermediate IMA-1, as shown in Table 1. The difference is that raw material 1 was used instead of 2,9-dibromo-1,10-phenanthroline, and raw material 2 was used instead of phenylboronic acid. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 1.
[0110] Table 1
[0111] 2. Synthesis of intermediate IMB-1
[0112] Intermediate IMA-1 (4.4 g, 13.1 mmol) and 4-chlorophenylboronic acid (2.3 g, 14.4 mmol) were dissolved in 35.2 mL of toluene, followed by the addition of tetra(triphenylphosphine)palladium (0.076 g, 0.066 mmol), K₂CO₃ (3.62 g, 26.3 mmol), 4.4 mL of ethanol, and 4.4 mL of water. The mixture was heated under reflux for 6 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was recrystallized from dichloromethane:n-heptane = 1:4 (v / v) to give intermediate IMA-1 (3.32 g, yield: 69%).
[0113] Intermediate IMB-X (X is 2 to 15) was prepared using the same synthesis as intermediate IMB-1, as shown in Table 2. The difference is that raw material 3 was used instead of IMA-1, and raw material 4 was used instead of 4-chlorophenylboronic acid. The main raw materials used, the intermediates synthesized and their yields are shown in Table 2.
[0114] Table 2
[0115] 3. Synthesis of intermediate IMC-X
[0116] Intermediate IMC-1 (3.3 g, 9 mmol) and pinacol diboronate (3.4 g, 13.5 mmol) were dissolved in 40 mL of 1,4-dioxane, followed by the addition of Pd(dba2)3 (0.08 g, 0.09 mmol), x-phos (0.9 g, 0.18 mmol), and potassium acetate (1.7 g, 18 mmol). The mixture was heated under reflux for 5 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was recrystallized from dichloromethane:n-heptane = 1:3 (v / v) to give intermediate IMC-1 (3.4 g, yield: 82%).
[0117] Intermediate IMC-X (X is 2 to 16) was prepared using the same synthesis method as intermediate IMC-1, as shown in Table 3. The difference is that raw material 5 was used instead of intermediate IMB-1. The main raw materials used, the intermediates synthesized and their yields are shown in Table 3.
[0118] Table 3
[0119] Synthesis Example 1: Synthesis of Compound 2
[0120] 7-Bromoindole[3,2,1-jk]carbazole (2.4 g, 7.4 mmol) and IMC-1 (3.4 g, 7.4 mmol) were added to a 100 mL three-necked flask, along with 24 mL of toluene, 2.5 mL of ethanol, 2.5 mL of water, tetrakis(triphenylphosphine)palladium (0.086 g, 0.074 mmol), and K₂CO₃ (2 g, 14.8 mmol). The mixture was heated under reflux for 6 h under a nitrogen atmosphere. After cooling to room temperature, 100 mL of water was added and the mixture was stirred for 30 min. The solid was collected by suction filtration, and the filtrate was washed with 100 mL of ethanol. This process was repeated three times. The obtained solid was recrystallized from dichloromethane to give compound 2 (2.9 g, yield: 69%). Mass spectrometry (m / z) = 572.21 [M+H] + .
[0121] The compounds shown in Table 4 were prepared using the same synthesis as compound 2, except that starting material 6 was used instead of starting material 7-bromoindole[3,2,1-jk]carbazole, and starting material 7 was used instead of IMC-1. The main starting materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 4.
[0122] Table 4
[0123] NMR data for compound 2:
[0124] 1 H-NMR(CD3Cl,400MHz):8.39-8.25(m,5H),8.20-8.16(m,3H),8.13-8.10(m,2H),7.92(d,1H),7.86-7.82(m,5H),7.59-7.35(m,9H).
[0125] NMR data for compound 102:
[0126] 1 H-NMR(CD3Cl,400MHz):8.66(s,1H),8.35-8.28(m,4H),8.24-8.11(m,4H),8 .05(s,2H),7.98(d,1H),7.87-7.79(m,2H),7.65(d,1H),7.59-7.42(m,10H).
[0127] Example 1: Blue Organic Electroluminescent Device
[0128] The device is fabricated using the following process: In an ITO / Ag / ITO layer with a thickness of [missing information], On the experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.
[0129] On the experimental substrate, compound HT-1 and PD were co-deposited at a deposition rate ratio of 98%:2% to form a thickness of [missing information]. Hole injection layer.
[0130] On the hole injection layer, compound HT-1 is deposited by vapor deposition to form a thickness of [thickness value missing]. The hole transport layer.
[0131] On the hole transport layer, compound EB-1 is deposited by vapor deposition to form a thickness of [thickness value missing]. The electron blocking layer.
[0132] On the electron blocking layer, compounds BH-1 and BD-1 were co-deposited at a deposition rate ratio of 99%:1% to form a layer with a thickness of [missing information]. The blue light-emitting layer.
[0133] Compound 2 and LiQ were co-deposited on the blue light-emitting layer at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. The electron transport layer.
[0134] 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.
[0135] 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.
[0136] Examples 2-6
[0137] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compound 2 was replaced with compounds in Table 5 below when forming the electron transport layer.
[0138] Comparative Example 1 - Comparative Example 2
[0139] Except that compound 2 was replaced with compounds A and B when forming the electron transport layer, the organic electroluminescent device was prepared using the same method as in Example 1.
[0140] The main material structures used in the above embodiments and comparative examples are shown below.
[0141] The performance of the blue organic electroluminescent devices prepared in Examples 1-6 and Comparative Examples 1-2 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. 95 Device lifetime is 15 mA / cm 2 The test was conducted under the specified conditions, and the results are shown in Table 5 below:
[0142] Table 5
[0143] Referring to Table 5 above, in Examples 1-6, using the compounds of this application as electron transport layer materials, the luminous efficiency was improved by at least 16.6% and the device lifetime by at least 17.81% compared to Comparative Examples 1-2. Therefore, using the organic compounds of this application as the electron transport layer of organic electroluminescent devices can improve the luminous efficiency and lifetime of the organic electroluminescent devices. 95 life.
[0144] To further illustrate the application of the compound of this application as a charge generation layer in multilayer organic electroluminescent devices, the following study investigates the properties of the material of this application by constructing a multilayer device.
[0145] Example 7: Red multilayer organic electroluminescent device
[0146] The anode is prepared through the following process: [The anode thickness is then determined sequentially to be...] The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). The substrate was then prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The substrate was then surface treated with ultraviolet light, ozone and O2:N2 plasma to increase the work function of the anode. The substrate surface was then cleaned with organic solvents to remove impurities and oil.
[0147] On the experimental substrate (anode), compound HT-2 and compound PD were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.
[0148] On the hole injection layer, compound HT-2 is deposited by vapor deposition to form a thickness of [thickness value missing]. The first hole transport layer.
[0149] On the first hole transport layer, compound HT-1 is deposited by vapor deposition to form a layer with a thickness of [missing information]. The first cavity adjustment layer.
[0150] On the first hole adjustment layer, compounds RH-1 and RD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. The first organic light-emitting layer.
[0151] On the first organic light-emitting layer, compound ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The first electron transport layer.
[0152] The above is the first light-emitting unit.
[0153] On the first electron transport layer, compound 2 and Yb were co-deposited at a deposition rate ratio of 99%:1% to form a layer with a thickness of [missing information]. An n-type charge-generating layer (n-CGL) was formed, and then compound HT-2 and compound PD were co-deposited on it at a deposition rate ratio of 95%:5% to form a layer with a thickness of [missing information]. The p-type charge generation layer (p-CGL).
[0154] The above is the charge generation layer (CGL).
[0155] On the p-type charge generation layer, compound HT-2 is deposited by vapor deposition to form a thickness of [thickness value missing]. The second hole transport layer.
[0156] On the second hole transport layer, compound HT-1 is deposited by vapor deposition to form a layer with a thickness of [missing information]. The second cavitation adjustment layer.
[0157] On the second hole adjustment layer, compounds RH-1 and RD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. The second organic light-emitting layer.
[0158] On the second organic light-emitting layer, compound ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate to form... A thick second electron transport layer.
[0159] The above is the second light-emitting unit.
[0160] Yb is deposited on the second electron transport layer to form a layer with a thickness of [missing information]. 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.
[0161] Finally, compound CP-2 is deposited on the cathode to form a thickness of [thickness missing]. The cathode capping layer is then used to complete the fabrication of the red stacked organic electroluminescent device.
[0162] Examples 8-29:
[0163] Except that when preparing the n-type charge generation layer, the organic electroluminescent device was prepared using the same method as in Example 7, except that the compound in Table 6 was used instead of compound 2 in Example 7.
[0164] Comparative Examples 3-4
[0165] Except that compounds C and D were used instead of compound 2 in Example 7 when preparing the n-type charge generation layer, the organic electroluminescent device was prepared using the same method as in Example 7.
[0166] The main material structures used in the above embodiments and comparative examples are shown below:
[0167] The performance of the red multilayer organic electroluminescent devices prepared in Examples 7-29 and Comparative Examples 3-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. 95 Device lifetime is 20 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 6 below.
[0168] Table 6
[0169] Referring to Table 6 above, in Examples 7-29, the compounds of this application were used as n-type charge generation layer materials, and compared with Comparative Examples 3-4, the luminous efficiency was improved by at least 13.4%, and the device lifetime was improved by at least 12.3%.
[0170] It is evident that using the organic compounds of this application in the n-type charge generation layer of organic electroluminescent devices can significantly improve the luminous efficiency and device lifetime of organic electroluminescent devices.
[0171] 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: Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and R 11 One or two of the groups are selected from the groups shown in Formula 2, and the others may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or heteroaryl with 3 to 12 carbon atoms; or, any two adjacent substituents among the others form a saturated or unsaturated 6 to 14-membered ring; L is 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 L 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, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms. Each R may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, alkenyl with 2 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms (substituted or unsubstituted), and heteroaryl with 3 to 30 carbon atoms (substituted or unsubstituted). The substituents in each R 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, or deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms. m represents the number of R groups, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R groups are the same or different; or any two adjacent R groups form a saturated or unsaturated 3 to 15-membered ring.
2. The organic compound according to claim 1, wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 and R 11 One or two of the groups are selected from the groups shown in Formula 2, and the others may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, phenyl, naphthyl, biphenyl, triazine, pyrimidinyl, pyridinyl, dibenzofuranyl, dibenzothiophene, or any two adjacent substituents of the others form a benzene ring, a naphthyl ring or a phenanthrene ring.
3. The organic compound according to claim 1, wherein, L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 16 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 12 carbon atoms; Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms.
4. The organic compound according to claim 1, wherein, L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted pyrene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted carbazolylene; Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, pyrimidinyl, pyrazinyl or pyridinyl.
5. The organic compound according to claim 1, wherein, Each R may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, trifluoromethyl, trideuterated methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl; or any two adjacent R form a saturated benzene ring, naphthyl ring, or phenanthyl ring; Optionally, the substituents in R may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, or carbazolyl.
6. The organic compound according to claim 1, wherein, Each R may be the same or different, and each is independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, vinyl, propenyl, allyl, trifluoromethyl, trideuterated methyl, or the group consisting of:
7. The organic compound according to claim 1, wherein, In Equation 2 Selected from the group consisting of the following groups:
8. The organic compound according to claim 1, wherein, In Equation 2 Selected from the group consisting of the following groups:
9. The organic compound according to claim 1, wherein, Formula 2 is selected from the group consisting of the following groups:
10. The organic compound according to claim 1, wherein, The organic compound is selected from the group consisting of the following compounds:
11. An organic electroluminescent device, comprising an anode and a cathode, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises the organic compound according to any one of claims 1 to 10; Optionally, the functional layer includes an electron transport layer, the electron transport layer comprising the organic compound according to any one of claims 1 to 10; Optionally, the functional layer includes a first light-emitting unit, a second light-emitting unit, and a charge-generating layer; the charge-generating layer contains an organic compound according to any one of claims 1 to 10.
12. An electronic device comprising the organic electroluminescent device of claim 11.
Citation Information
Patent Citations
Nitrogen-containing condensed cyclic compound and organic light emitting element using same
CN106661037A
Indolocarbazole-containing organic semiconductor material and application thereof to organic luminous device
CN106977520A
Compound, preparation method thereof and light-emitting diode
CN111233897A
Heterocyclic compound and organic light emitting device comprising the same
KR1020170108894A
Heterocyclic compound and organic light emitting device comprising the same
KR1020170108895A