Organic compounds, electronic components and electronic devices

By using triazine compounds with a benzoxazole-fused dibenzo five-membered ring structure as electron transport host materials, the lifetime and efficiency problems of organic electroluminescent devices in large-area displays were solved, the carrier mobility and exciton generation efficiency were improved, and the luminous efficiency and lifetime of the devices were enhanced.

CN117466910BActive Publication Date: 2025-10-28SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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Patent Information

Application Number
CN202211565136.8
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-12-07
Publication Date
2025-10-28
Estimated Expiration
2042-12-07

AI Technical Summary

Technical Problem

Existing organic electroluminescent devices face issues with lifespan and efficiency in large-area displays, requiring high driving voltages and improvements in luminous and current efficiencies.

Method used

Triazine compounds with a benzoxazole-fused dibenzo five-membered ring core structure are used as electron transport host materials to enhance intermolecular forces, improve carrier mobility, and increase exciton generation and utilization efficiency.

Benefits of technology

By improving carrier balance and widening the carrier recombination region, the luminous efficiency and lifetime of the device can be improved.

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Abstract

This application relates to an organic compound and electronic components and devices comprising the same. The organic compound of this application has a general structure as shown in Formula 1. Applying this organic compound to organic electroluminescent devices can significantly improve the performance of the devices.
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Description

Technical Field

[0001] This application belongs to the field of organic materials technology, and in particular relates to an organic compound and electronic components and devices containing 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. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer serving as the energy conversion layer, an electron transport layer, and a cathode stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light.

[0003] The most significant issues with existing organic light-emitting diodes (OLEDs) are lifespan and efficiency. As displays become larger, driving voltages increase, necessitating improvements in both luminous and current efficiency. Therefore, it is essential to continue developing novel organic light-emitting layer materials to further enhance the performance of OLEDs. Summary of the Invention

[0004] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and electronic components and devices containing the same, wherein the organic compound can improve the performance of electronic components and devices, such as improving device efficiency and lifespan.

[0005] To achieve the above-mentioned objectives, this application adopts the following technical solution:

[0006] According to a first aspect of this application, an organic compound is provided having the general formula shown in Formula 1:

[0007]

[0008] Ring A is the group shown in Formula 2;

[0009] Any two adjacent * positions in Equation 2 are the same as those in Equation 1. The # positions are mutually dense;

[0010] One of X1 and X2 is O or S, and the other is -N=;

[0011] X represents C(R4R5), N(R6), O, or S;

[0012] R3 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, substituted or unsubstituted heteroaryl groups with 12-40 carbon atoms, or groups represented by Formula 3.

[0013] Each R1 and R2 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, cycloalkyl with 3-10 carbon atoms, or a group represented by Formula 3;

[0014] n1 is the number of R1s, which can be selected from 1, 2, 3 or 4; when n1 is greater than 1, any two R1s can be the same or different.

[0015] n2 is the number of R2s, selected from 1, 2, 3, 4, 5 or 6; when n2 is greater than 1, any two R2s are the same or different.

[0016] R4 and R5 are selected from alkyl groups having 1-10 carbon atoms, aryl groups having 6-20 carbon atoms, heteroaryl groups having 3-20 carbon atoms, and cycloalkyl groups having 3-10 carbon atoms;

[0017] R6 is selected from aryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, or groups represented by Formula 3.

[0018] Among them, R1, R2, R3 and R6 have exactly one group that is shown in Formula 3;

[0019] L, L1 and L2 are selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0020] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-40 carbon atoms.

[0021] The substituents in R3, L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, haloaryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, or cycloalkyl with 3-10 carbon atoms;

[0022] Optionally, in Ar1 and Ar2, any two adjacent substituents can form saturated or unsaturated 3-15 membered rings.

[0023] According to a second aspect of this application, an electronic component is provided, comprising 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.

[0024] According to a third aspect of this application, an electronic device is provided, comprising the electronic components described in the second aspect.

[0025] The organic compound structure of this application contains a benzoxazole-fused dibenzo5-membered ring core structure, with a triazine compound attached to the core as an electron transport host material. The benzoxazole-fused dibenzo5-membered ring possesses a large conjugated system; attaching it to a triazine enhances intermolecular forces and improves the compound's carrier mobility. Using the organic compound of this application as the electron transport host material in a hybrid host material can improve carrier balance in the organic light-emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and ultimately enhance the device's luminous efficiency and lifetime.

[0026] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0027] 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.

[0028] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0029] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0030] Figure Labels

[0031] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0032] 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer.

[0033] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0034] 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.

[0035] In a first aspect, this application provides an organic compound having the general formula shown in Formula 1:

[0036]

[0037] Ring A is the group shown in Formula 2;

[0038] Any two adjacent * positions in Equation 2 are the same as those in Equation 1. The # positions are mutually dense;

[0039] One of X1 and X2 is O or S, and the other is -N=;

[0040] X represents C(R4R5), N(R6), O, or S;

[0041] R3 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, substituted or unsubstituted heteroaryl groups with 12-40 carbon atoms, or groups represented by Formula 3.

[0042] Each R1 and R2 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, cycloalkyl with 3-10 carbon atoms, or a group represented by Formula 3;

[0043] n1 is the number of R1s, which can be selected from 1, 2, 3 or 4; when n1 is greater than 1, any two R1s can be the same or different.

[0044] n2 is the number of R2s, selected from 1, 2, 3, 4, 5 or 6; when n2 is greater than 1, any two R2s are the same or different.

[0045] R4 and R5 are selected from alkyl groups having 1-10 carbon atoms, aryl groups having 6-20 carbon atoms, heteroaryl groups having 3-20 carbon atoms, and cycloalkyl groups having 3-10 carbon atoms;

[0046] R6 is selected from aryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, or groups represented by Formula 3.

[0047] Among them, R1, R2, R3 and R6 have exactly one group that is shown in Formula 3;

[0048] L, L1 and L2 are selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0049] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms or substituted or unsubstituted heteroaryl groups with 3-40 carbon atoms.

[0050] R3, L, L1, L2, Ar1, and Ar2 may have the same or different substituents, and each may be independently selected from deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, triphenylsilyl groups, aryl groups with 6-20 carbon atoms, haloaryl groups with 6-20 carbon atoms, deuterated aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, or cycloalkyl groups with 3-10 carbon atoms;

[0051] Optionally, in Ar1 and Ar2, any two adjacent substituents can form saturated or unsaturated 3-15 membered rings.

[0052] According to a second aspect of this application, an electronic component is provided, comprising 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.

[0053] In this application, the fluorene group can be replaced by one or two substituents. Specifically, when the fluorene group is replaced, the following substitutions can be made: etc., but not limited to this.

[0054] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each 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.

[0055] 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, heteroaryl, aryl, deuterated aryl, haloaryl, trialkylsilyl, triphenylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc.

[0056] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0057] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, triphenylene, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0058] In this application, terphenyl includes

[0059] 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 atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, 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 thereon. 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 thereon is 18.

[0060] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6, or 7 heteroatoms. The heteroatoms can be at least one 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. Each aromatic ring system can be an aromatic monocyclic ring or an aromatic fused 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. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazoyl and N-pyridylcarbazoyl are heteroaryl groups of the multiple aromatic ring type connected by carbon-carbon bonds in a conjugated manner. In this application, the hypoaryl group refers to the divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0061] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, 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.

[0062] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6-40, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40.

[0063] In this application, specific examples of aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and fluorenyl.

[0064] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 3-40, 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, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40.

[0065] In this application, specific examples of heteroaryl groups as substituents include, but are not limited to, carbazolyl, dibenzofuranyl, and dibenzothiophenel.

[0066] In this application, the non-positioned linker refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0067] In this application, alkyl groups having 1-10 carbon atoms can include straight-chain alkyl groups having 1-10 carbon atoms and branched alkyl groups having 3-10 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-octyl, 2-ethylhexyl, nonyl, decyl, and 3,7-dimethyloctyl.

[0068] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0069] In this application, the number of carbon atoms in cycloalkyl groups with 3-10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl and cyclohexyl.

[0070] In this application, the deuterated alkyl group having 1-10 carbon atoms can be, for example, a trideuterated methyl group.

[0071] In this application, the deuterated aryl group having 6-20 carbon atoms can be, for example, a pentadeuterated phenyl group.

[0072] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule by two non-positional linkages that span the bicyclic ring, which means that any possible connection mode is shown as in equations (f-1) to (f-10).

[0073]

[0074] For another example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule by a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0075]

[0076] In some embodiments of this application, X1 is -N= and X2 is 0.

[0077] In other embodiments of this application, X1 is 0, X2 is -N=, that is, Equation 1 is

[0078] In some embodiments of this application, the organic compound is selected from the structures shown in Formulas 1-1 to 1-15:

[0079]

[0080]

[0081] m is the number of R2 values, which are independently selected from 1, 2, 3, 4 or 5.

[0082] In the structures shown in Formulas 1-1 to 1-14, each R1 and R2 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, or cycloalkyl with 3-10 carbon atoms.

[0083] In some embodiments of this application, each of R1 and R2 may be the same or different, and is independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0084] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12-20 carbon atoms.

[0085] Optionally, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0086] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trideuterated methyl, pentadeuterated phenyl or aryl with 6-12 carbon atoms;

[0087] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

[0088] In other embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoleyl.

[0089] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, pentadeuterated phenyl, phenyl, naphthyl, or biphenyl.

[0090] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups:

[0091]

[0092] Wherein, the substituted group W has one or more substituents, wherein the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, pentadeuterated phenyl, phenyl, naphthyl, biphenyl, and when the number of substituents is greater than 1, the substituents are the same or different.

[0093] In some embodiments of this application, Ar1 and Ar2 are each independently selected from the group consisting of:

[0094]

[0095] Specifically, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0096]

[0097]

[0098] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12-20 carbon atoms.

[0099] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1-5 carbon atoms.

[0100] Further optionally, L is selected from a single bond or a substituted or unsubstituted aryl group having 6-12 carbon atoms.

[0101] In other embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0102] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0103] Further optionally, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0104] In some embodiments of this application, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0105]

[0106] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.

[0107] Optionally, L1 and L2 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

[0108]

[0109] Specifically, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0110]

[0111] In some embodiments of this application, L is selected from the group consisting of single bonds or the following groups:

[0112]

[0113] In some embodiments of this application, Each is independently selected from the group consisting of the following groups:

[0114]

[0115] Specifically, Each is independently selected from the group consisting of the following groups:

[0116]

[0117] In some embodiments of this application, Selected from the group consisting of the following groups:

[0118]

[0119]

[0120]

[0121] In some embodiments of this application, R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl or a group represented by Formula 3.

[0122] Optionally, the substituents in R3 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, trideuterated methyl, and phenyl.

[0123] In some embodiments of this application, R4 and R5 are selected from methyl groups.

[0124] In some embodiments of this application, each R1 is selected from hydrogen or deuterium.

[0125] In some embodiments of this application, each R2 is selected from hydrogen, deuterium, or a group represented by Formula 3;

[0126] R6 is selected from phenyl, naphthyl, biphenyl or a group represented by Formula 3;

[0127] Furthermore, each of R2 and R6 has one and only one group that is represented by Formula 3.

[0128] Further optionally, one of each R2 is a group shown in Formula 3, and the remaining R2 are independently selected from hydrogen or deuterium.

[0129] Alternatively, R6 is a group shown in Formula 3, and each R2 is independently selected from hydrogen or deuterium.

[0130] Further optionally, R3 is a group shown in Formula 3, each R2 is independently selected from hydrogen or deuterium, and R6 is selected from phenyl, naphthyl, or biphenyl.

[0131] Optionally, the organic compound is selected from the following compounds:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] 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.

[0149] In some embodiments of this application, 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 320, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200 stacked sequentially.

[0150] In some specific embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device.

[0151] Optionally, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode includes indium tin oxide (ITO) as the anode.

[0152] Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, wherein the first hole transport layer is closer to the anode than the second hole transport layer.

[0153] In this application, the hole transport layer 320 may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically selected from the compounds listed below or any combination thereof:

[0154]

[0155] In one embodiment of this application, the first hole transport layer 321 is composed of HT-1.

[0156] In one embodiment of this application, the second hole transport layer 322 is composed of HT-2.

[0157] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof:

[0158]

[0159] In some embodiments of this application, the hole injection layer 310 is composed of PD and HT-1.

[0160] 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.

[0161] The main 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.

[0162] In some embodiments of this application, the main material of the organic light-emitting layer 330 is the organic compound and RH-P of this application.

[0163] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of the red phosphorescent dopant include, but are not limited to:

[0164]

[0165] In some specific embodiments of this application, the guest material of the organic light-emitting layer 330 is RD.

[0166] 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 may be selected from, but are not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0167]

[0168] In some specific embodiments of this application, the electronic transport layer 340 is composed of ET-1 and LiQ of this application.

[0169] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0170] Optionally, an electron injection layer 350 may be 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 some embodiments of this application, the electron injection layer 350 may include ytterbium (Yb).

[0171] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0172] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0173] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0174] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0175] Synthesis Examples

[0176] I. Synthesis of intermediate Sub-aX

[0177] Synthesis of intermediate Sub-a1:

[0178]

[0179] Under nitrogen protection, 2-iodo-3-bromophenol (14.89 g, 50 mmol), benzylamine (10.71 g, 100 mmol), sodium periodate (21.59 g, 100 mmol), 2,2,6,6-tetramethylpiperidine oxide (TEMPO, 15.63 g, 100 mmol), and ethyl acetate (200 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was stirred at 50 °C for 24 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane as the mobile phase to obtain a grayish-white solid intermediate, Sub-a1 (8.37 g, yield 42%).

[0180] Following the synthetic method of intermediate Sub-a1, intermediate Sub-aX was synthesized by replacing benzylamine with reactant A shown in Table 1.

[0181] Table 1 Synthesis of intermediate Sub-aX

[0182]

[0183] II. Synthesis of intermediate Sub-bX

[0184] Synthesis of intermediate Sub-b1:

[0185]

[0186] Under nitrogen protection, 1-bromo-3-chlorodibenzofuran (19.60 g, 70 mmol) and dry tetrahydrofuran (400 mL) were added to a 1000 mL three-necked flask; the system was cooled to -78 °C, and n-butyllithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the mixture was kept at -78 °C and stirred for 1 hour; while maintaining the temperature at -78 °C, trimethyl borate (10.91 g, 105 mL) was added dropwise. After the addition of mol, the mixture was kept at -78℃ for 1 hour, and then allowed to naturally warm to room temperature. Dilute hydrochloric acid (2M, 58mL) was added dropwise to the reaction solution and stirred for 30 minutes. The mixture was extracted with dichloromethane (100mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was slurried with n-heptane and filtered to obtain the white solid intermediate Sub-b1 (10.67g, 62%).

[0187] Following the synthetic method of intermediate Sub-b1, intermediates Sub-b2 to Sub-b14 were synthesized by replacing 1-bromo-3-chlorodibenzofuran with reactant B shown in Table 2.

[0188] Table 2 Synthesis of intermediates Sub-b2 to Sub-b14

[0189]

[0190]

[0191]

[0192] III. Synthesis of the intermediate Sub-cX

[0193] Synthesis of intermediate Sub-c1:

[0194]

[0195] Under nitrogen protection, Sub-a1 (19.94 g, 50 mmol), Sub-b1 (13.53 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid intermediate, Sub-c1 (15.84 g, yield 67%).

[0196] Referring to the synthesis method of intermediate Sub-c1, reactant C shown in Table 3 was used to replace Sub-a1, and reactant D was used to replace Sub-b1 to synthesize intermediates Sub-c2 to Sub-c20.

[0197] Table 3 Synthesis of intermediates Sub-c2 to Sub-c20

[0198]

[0199]

[0200]

[0201] IV. Synthesis of intermediate Sub-dX: Synthesis of intermediate Sub-d1:

[0202]

[0203] Under nitrogen protection, Sub-Cl (23.65 g, 50 mmol) and dry tetrahydrofuran (250 mL) were added to a 500 mL three-necked flask; the system was cooled to -78 °C, and n-butyllithium solution (2.0 M n-hexane solution, 27.5 mL, 55 mmol) was added dropwise. After the addition was complete, the mixture was kept at -78 °C and stirred for 1 hour; while maintaining the temperature at -78 °C, N,N-dimethylformamide (5.48 g, 75 mmol) was added dropwise. After the addition was complete... Continue to maintain the temperature (-78℃) for 1 hour, then allow the system to naturally warm to room temperature; add deionized water to quench the reaction solution and continue stirring for 30 minutes; extract with dichloromethane (100mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain crude product; use dichloromethane / n-heptane as mobile phase to purify the crude product by silica gel column chromatography to obtain pale yellow solid intermediate Sub-d1 (17.77g, yield 84%).

[0204] Following the synthesis method of intermediate Sub-d1, intermediates Sub-d2 to Sub-d20 were synthesized by replacing Sub-c1 with reactant E shown in Table 4.

[0205] Table 4 Synthesis of intermediates Sub-d2 to Sub-d20

[0206]

[0207]

[0208]

[0209] V. Synthesis of intermediate Sub-eX

[0210] Synthesis of intermediate Sub-e1:

[0211]

[0212] Under nitrogen protection, Sub-d1 (55 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol), and anhydrous tetrahydrofuran (600 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to 0 °C using an ice-water bath. Then, an anhydrous tetrahydrofuran solution of potassium tert-butoxide (1 M, 220 mL) was slowly added dropwise. After the addition was complete, the system was slowly heated to room temperature, and the reaction was stirred for 6 h. The reaction solution was poured into 1000 mL of deionized water and extracted with ethyl acetate (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (45.74 g, yield 78%).

[0213] Following the synthesis method of intermediate Sub-e1, reactant F shown in Table 5 was used to replace Sub-d1 to synthesize intermediates Sub-e2 to Sub-e20.

[0214] Table 5 Synthesis of intermediates Sub-e2 to Sub-e20

[0215]

[0216]

[0217]

[0218] VI. Synthesis of intermediate Sub-fX

[0219] Synthesis of intermediate Sub-f1:

[0220]

[0221] Under nitrogen protection, Sub-e1 (53.68 g, 119 mmol), Eaton reagent (4.5 mL), and chlorobenzene (550 mL) were added sequentially to a 2000 mL three-necked flask. The mixture was heated to reflux and stirred for 8 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid intermediate, Sub-f1 (26.43 g, yield 53%).

[0222] Referring to the synthesis of intermediate Sub-f1, intermediates Sub-f2 to Sub-f20 were synthesized by replacing Sub-e1 with reactant G as shown in Table 6.

[0223] Table 6 Synthesis of intermediates Sub-f2 to Sub-f20

[0224]

[0225]

[0226]

[0227] Synthesis of intermediate Sub-f21:

[0228]

[0229] Under nitrogen protection, Sub-f3 (10.47 g, 25 mmol) and 200 mL of benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 minutes. A saturated aqueous solution of K3PO4 was then added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid intermediate, Sub-f21 (5.17 g, yield 48%).

[0230] VII. Synthesis of intermediate Sub-gX

[0231] Synthesis of intermediate Sub-g1:

[0232]

[0233] Under nitrogen protection, Sub-f1 (18.44 g, 44 mmol), pinacol diborate (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol), and 1,4-dioxane (120 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and when the system reached 40 °C, tris(dibenzylacetone)palladium (0.40 g, 0.44 mmol) and (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.42 g, 0.88 mmol) were quickly added. The temperature was further increased to reflux, and the reaction was stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid intermediate Sub-g1 (15.30 g, yield 68%) was obtained.

[0234] Following the synthesis method of intermediate Sub-g1, intermediates Sub-g2 to Sub-g21 were synthesized by replacing Sub-f1 with reactant H shown in Table 7.

[0235] Table 7 Synthesis of intermediates Sub-g2 to Sub-g21

[0236]

[0237]

[0238]

[0239]

[0240] VIII. Synthesis of Compounds

[0241] Synthesis of compound 4:

[0242]

[0243] Under nitrogen protection, Sub-g1 (13.42 g, 26.25 mmol), Sm-1 (CAS: 2737218-48-1, 9.03 g, 25 mmol), tetra(triphenylphosphine)palladium (0.29 g, 0.25 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol), tetrabutylammonium bromide (0.8 g, 2.5 mmol), toluene (120 mL), tetrahydrofuran (30 mL), and deionized water (30 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give a white solid compound 4 (13.31 g, yield 75%, m / z = 711.2 [M+H)). + ).

[0244] Following the synthetic method of compound 4, reactant J was used instead of Sub-g1 and reactant K was used instead of Sm-1, as shown in Table 8, to synthesize the compounds shown in Table 8.

[0245] Table 8 Synthesis of the compounds in this application

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] NMR data for some intermediates and compounds are shown in Table 9 below:

[0258] Table 9

[0259]

[0260] Fabrication and evaluation of organic electroluminescent devices:

[0261] This application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the aforementioned organic compound of this application. The organic electroluminescent device of this application will be described in detail below through embodiments. However, the following embodiments are merely examples of this application and are not intended to limit the scope of this application.

[0262] Example 1: Fabrication of a red organic electroluminescent device

[0263] Anodizing pretreatment is performed through the following process: at thicknesses sequentially of... On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0264] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The first hole transport layer. Compound HT-2 is vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer.

[0265] Next, on the second hole transport layer, compound 4:RH-P:RD was co-deposited at a thickness ratio of 49%:49%:2% to form a film with a thickness of [missing information]. Organic light-emitting layer (EML, red light-emitting layer).

[0266] On the organic light-emitting layer, compound ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) is formed, and then magnesium (Mg) and silver (Ag) are mixed at a evaporation rate ratio of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0267] Furthermore, compound CP-1 was vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The organic coating layer (CPL) is used to complete the fabrication of the red organic electroluminescent device.

[0268] Examples 2-58:

[0269] Organic electroluminescent devices were prepared using the same method as in Example 1, except that, when preparing the organic light-emitting layer, the compound in Table 10 was used instead of compound 4 in Example 1.

[0270] Comparative Examples 1-3:

[0271] Organic electroluminescent devices were prepared using the same method as in Example 1, except that when preparing the organic light-emitting layer, compound 4 was replaced with compounds A, B, and C in the table below.

[0272] The structures of the materials used in the comparative and example studies for fabricating organic electroluminescent devices are as follows:

[0273]

[0274] The performance of the red organic electroluminescent devices prepared in Examples 1-58 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 20 mA / cm. 2 The lifespan of the T95 device was tested under the specified conditions, and the test results are shown in Table 10.

[0275] Table 10

[0276]

[0277]

[0278]

[0279] As can be seen from the table above, when the organic compound of this application is used as the main material of the red organic electroluminescent device compared with the organic electroluminescent devices of Comparative Examples 1-3, the current efficiency is increased by at least 10.2% and the lifetime is increased by at least 10.4%.

[0280] The organic compound structure of this application contains a benzoxazole-fused dibenzo5-membered ring core structure, with a triazine compound attached to the core as an electron transport-type red light host material. The benzoxazole-fused dibenzo5-membered ring possesses a large conjugated system; its connection with a triazine enhances intermolecular forces and improves the compound's carrier mobility. When the organic compound of this application is used as the electron transport-type host material in a hybrid host material, it can improve carrier balance in the organic light-emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and ultimately enhance the device's luminous efficiency and lifetime.

[0281] 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 general formula shown in Formula 1: Ring A is the group shown in Formula 2; Any two adjacent * positions in Equation 2 are the same as those in Equation 1. The # positions are mutually dense; One of X1 and X2 is O or S, and the other is -N=; X represents C(R4R5), N(R6), O, or S; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl or a group represented by Formula 3. The substituents in R3 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, or phenyl. Each R1 and R2 may be the same or different, and each is independently selected from hydrogen, deuterium or the group shown in Formula 3; n1 is the number of R1s, which can be selected from 1, 2, 3 or 4; when n1 is greater than 1, any two R1s can be the same or different. n2 is the number of R2s, selected from 1, 2, 3, 4, 5 or 6; when n2 is greater than 1, any two R2s are the same or different. R4 and R5 are selected from alkyl groups having 1-10 carbon atoms and aryl groups having 6-20 carbon atoms; R6 is selected from phenyl, naphthyl, biphenyl or a group represented by Formula 3; Among them, R1, R2, R3 and R6 have exactly one group that is shown in Formula 3; L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6-20 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12-20 carbon atoms. The substituents in L, L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1-5 carbon atoms; Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms or substituted or unsubstituted heteroaryl groups with 12-20 carbon atoms. The substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trideuterated methyl, pentadeuterated phenyl or aryl with 6-12 carbon atoms.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structures shown in Formulas 1-1 to 1-15: In Equations 1-1 to 1-13, m is the number of R2, which are independently selected from 1, 2, 3, 4 or 5.

3. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazoyl.

4. The organic compound according to claim 3, characterized in that, The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, pentadeuterated phenyl, phenyl, naphthyl, or biphenyl.

5. The organic compound according to claim 1, characterized in that, L, L1, and L2 may be the same or different, and each is independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

6. The organic compound according to claim 5, characterized in that, The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

7. The organic compound according to claim 1, characterized in that, and Each is independently selected from the group consisting of the following groups:

8. The organic compound according to claim 1, characterized in that, Each R1 is selected from hydrogen or deuterium; Each R2 may be the same or different, and is independently selected from hydrogen, deuterium or the group shown in Formula 3; R6 is selected from phenyl, naphthyl, biphenyl or a group represented by Formula 3; Furthermore, each of R2 and R6 has one and only one group that is represented by Formula 3.

9. The organic compound according to claim 8, characterized in that, One of each R2 is a group shown in Formula 3, and the remaining R2 are each independently selected from hydrogen or deuterium; Alternatively, R6 is a group shown in Formula 3, and each R2 is independently selected from hydrogen or deuterium.

10. The organic compound according to claim 1, characterized in that, R3 is the group shown in Formula 3, each R2 is independently selected from hydrogen or deuterium, and R6 is selected from phenyl, naphthyl, or biphenyl.

11. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds:

12. An electronic component, comprising an anode and a cathode disposed opposite to each other, 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 1-11.

13. The electronic component according to claim 12, characterized in that, The electronic component is an organic electroluminescent device.

14. The electronic component according to claim 12 or 13, characterized in that, The functional layer includes an organic light-emitting layer, which contains the organic compound.

15. An electronic device, characterized in that, Includes the electronic components described in any one of claims 12-14.

Citation Information

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