Organic compound, electronic element, and electronic device
By using a novel organic compound in the luminescence adjustment layer of an organic electroluminescent device, the compound introduces specific aryl/heteroaryl and arylamine groups on the cycloalkane spirofluorene structure, the problems of easy crystallization and short service life of existing materials are solved, and higher luminescence efficiency and thermal stability are achieved.
Patent Information
- Application Number
- PCT/CN2024/117966
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-10-07
- Filing Date
- 2024-09-10
- Publication Date
- 2025-04-10
AI Technical Summary
The molecular structure of the material in the existing organic electroluminescent devices is too stretched in the luminescent adjustment layer, resulting in problems such as high evaporation temperature, easy crystallization and short service life.
A new organic compound is designed to introduce specific aryl/heteroaryl groups at the 3 or 4 position of the cycloalkane spirofluorene structure, and connect arylamine groups to the benzene ring of the fluorenyl group to form a non-linear structure connection method to improve its conjugated area and spatial distortion degree.
By using this new organic compound as the luminescence adjustment layer material, the mobility of molecules is improved, the formation of hole transport traps is avoided, the luminescence efficiency and thermal stability of organic electroluminescent devices are significantly improved, and the service life of the device is extended.
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Figure CN2024117966_10042025_PF_FP_ABST
Abstract
Description
Organic compounds, electronic components and electronic devices
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to the Chinese patent application with application number CN2023112871093 filed on October 7, 2023. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field
[0003] The present application relates to the field of organic electroluminescence, and in particular to an organic compound, an electronic component and an electronic device. Background Art
[0004] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent display devices are a type of self-luminous display device that generates excitons through the transfer and recombination of carriers between various functional layers, and relies on high-quantum-efficiency organic compounds or metal complexes to emit light. Organic electroluminescent devices (OLEDs, i.e. organic light-emitting diodes) are a type of self-luminous electronic components with the characteristics of high contrast, wide viewing angle, fast response speed, and excellent color expression. They can also be prepared on flexible substrates into rollable or bendable flexible display products. Therefore, in recent years, OLED displays have been widely used in consumer electronics such as mobile phones, tablets, and wall-mounted TVs, as well as in the field of vehicle-mounted displays.
[0005] The structure of an organic electroluminescent element typically includes an anode, a cathode, and an organic functional layer between them. To improve the efficiency and lifespan of an organic electroluminescent element, the organic layer has a multilayer structure, with each layer containing different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, which emit light when they transition back to the ground state.
[0006] Therefore, to achieve efficient organic electroluminescent devices, in addition to developing high-performance materials for the light-emitting layer, it is also crucial to develop corresponding hole-transporting materials, such as those for the luminescence-modulating layer. Therefore, designing new, higher-performing materials to enhance device performance has long been a pressing challenge for those skilled in the art.
[0007] Summary of the Invention
[0008] The purpose of the present application is to provide an organic compound, an electronic component and an electronic device. Using the organic compound in an organic electroluminescent device can improve the performance of the device.
[0009] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:
[0010] wherein one of R1 and R2 is selected from the other is selected from H or D;
[0011] n is selected from 1, 2, 3 or 4;
[0012] L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
[0013] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;
[0014] The substituents in L and Ar are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trideuterated methyl group or a phenyl group;
[0015] L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0016] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
[0017] The substituents in L1, L2, L3, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.
[0018] The second aspect of the present application provides an electronic component, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described in the first aspect.
[0019] A third aspect of the present application provides an electronic device comprising the electronic component described in the second aspect.
[0020] The organic compound of the present application has a 3-position or 4-position of the cycloalkane spirofluorene structure. Introducing a specific set of aryl / heteroaryl groups At the same time, an aromatic amine group is connected to the benzene ring of the fluorene group, and the entire compound presents a non-linear structural connection mode. This "cycloalkyl spirofluorene + aromatic amine" type compound also has a higher conjugated area and a higher degree of spatial distortion. The organic compound of the present application, on the one hand, has a reasonable glass transition temperature (Tg) range. When it is applied to the preparation of OLED devices for evaporation, it has a better evaporation morphology, which prolongs the service life of the device; on the other hand, the aromatic / heteroaromatic and aromatic amine groups at the 3rd or 4th positions of the spirofluorene plane form a complete π-π conjugated plane with the fluorene ring of the spirofluorene structure. This structural feature effectively increases the conjugated area of the molecule, thereby increasing the molecular mobility and avoiding the formation of hole transport traps. Applying it to the luminescence adjustment layer of OLED devices can effectively improve the luminous efficiency of the device. Compared with existing hole transport materials, the organic compound of the present application can avoid the problems of high evaporation temperature and easy crystallization in traditional materials due to the overly stretched molecular structure. When the organic compound of the present application is applied as a luminescence adjustment layer to an OLED device, it can not only improve the molecular mobility of the material, but also exhibit excellent thermal stability, effectively improving the problems of traditional materials such as easy crystallization, poor film uniformity, and short service life during repeated charge and discharge use of the device. BRIEF DESCRIPTION OF THE DRAWINGS
[0021] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.
[0022] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
[0023] FIG2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
[0024] FIG3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
[0025] FIG4 is a schematic diagram of a second electronic device according to an embodiment of the present application.
[0026] Description of Reference Numerals
[0027] 100, anode 200, cathode 300, functional layer 310, hole injection layer
[0028] 320, hole transport layer 321, luminescence adjustment layer 330, organic light emitting layer 340, electron transport layer
[0029] 350, electron injection layer 360, photoelectric conversion layer 400, first electronic device 500, second electronic device DETAILED DESCRIPTION
[0030] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of 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 concepts of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a full understanding of the embodiments of the present application.
[0031] In a first aspect, the present application provides an organic compound having a structure shown in Formula 1:
[0032] wherein one of R1 and R2 is selected from the other is selected from H or D;
[0033] n is selected from 1, 2, 3 or 4;
[0034] L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group;
[0035] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;
[0036] The substituents in L and Ar are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trideuterated methyl group or a phenyl group;
[0037] L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
[0038] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
[0039] The substituents in L1, L2, L3, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.
[0040] In this application, Refers to chemical bonds to other substituents or binding sites.
[0041] In this application, the descriptions “each independently is”, “each independently selected from” and “each independently selected from” are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
[0042] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a trialkylsilyl group, an aryl group, or a heteroaryl group. The number of substituents Rc can be one or more.
[0043] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.
[0044] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, or two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl in the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, spirobifluorenyl, etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, triphenylene, Ji et al.
[0045] In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
[0046] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are replaced by a group such as deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a trialkylsilyl group, an aryl group, or a heteroaryl group. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to a total number of carbon atoms in the aryl group and the substituents.
[0047] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl , carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiphenyl, benzofuryl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, silylfluorenyl, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, spiro(fluorene-9,9'-xanthenyl) Xanthenyl etc., but not limited to these.
[0048] In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.
[0049] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by a group such as deuterium, a halogen group, a cyano group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a trialkylsilyl group, an aryl group, or a heteroaryl group. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, a phenyl-substituted dibenzofuranyl group, a phenyl-substituted dibenzothienyl group, a phenyl-substituted pyridyl group, and the like. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
[0050] In the present application, specific examples of aryl groups as substituents in L1, L2, L3, Ar1 and Ar2 include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, Ji et al.
[0051] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.
[0052] In the present application, specific examples of heteroaryl groups as substituents in L1, L2, L3, Ar1 and Ar2 include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl and the like.
[0053] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.
[0054] In this application, the structure shown in Formula 1 When n=1, for When n=2, for When n=3, for When n=4, for
[0055] In this application, D represents deuterium.
[0056] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
[0057] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
[0058] In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.
[0059] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
[0060] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.
[0061] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).
[0062] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4).
[0063] A non-positional substituent as used herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within the ring system. For example, as shown in Formula (Y) below, the substituent R' represented by Formula (Y) is connected to the quinoline ring via a non-positional bond, and its meaning includes any possible connection method shown in Formulas (Y-1) to (Y-7).
[0064] In some embodiments, R1 is selected from R2 is selected from H or D.
[0065] In some embodiments, R2 is selected from R1 is selected from H or D.
[0066] In some embodiments, the organic compound of the present application is selected from the structure shown in Formula I-1, Formula I-2, Formula I-3 or Formula I-4:
[0067] In Formulae I-1 to I-4, L, L1, L2, L3, Ar, Ar1 and Ar2 are defined the same as in Formula I.
[0068] In some embodiments, L is selected from the group consisting of a single bond or the following groups:
[0069] In some embodiments, L is selected from the group consisting of a single bond or the following groups:
[0070] In some embodiments, Ar is selected from the group consisting of:
[0071] In some embodiments, Ar is selected from the group consisting of:
[0072] In some preferred embodiments, Selected from the group consisting of:
[0073] In some preferred embodiments, Selected from the group consisting of:
[0074] In some embodiments, L1, L2, and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms. For example, L1, L2, and L3 are the same or different and are each independently selected from a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0075] In some embodiments, the substituents in L1, L2 and L3 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, or a phenyl group.
[0076] In some embodiments, L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted carbazolylene group.
[0077] Optionally, the substituents in L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl.
[0078] In some embodiments, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:
[0079] In some embodiments, L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:
[0080] In some embodiments, L3 is selected from the group consisting of a single bond or the following groups:
[0081] In some embodiments, L3 is selected from the group consisting of a single bond or the following groups:
[0082] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms. For example, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms.
[0083] In some embodiments, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.
[0084] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of:
[0085] The substituted group Q has one or more substituents, each substituent is the same or different, and each substituent is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
[0086] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of:
[0087] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of:
[0088] In some embodiments, Selected from the group consisting of:
[0089] Specifically, the organic compound described in the present application can be selected from the group consisting of the following compounds:
[0090] In a second aspect, the present application provides an electronic component comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described in the first aspect of the present application.
[0091] Optionally, the functional layer includes a luminescence adjustment layer, and the luminescence adjustment layer includes the organic compound of the present application.
[0092] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.
[0093] Further optionally, the organic electroluminescent device is a red organic electroluminescent device.
[0094] In one embodiment, the electronic component is an organic electroluminescent device, as shown in FIG1 , which may include a stacked anode 100 , a hole transport layer 320 , a luminescence adjustment layer 321 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 .
[0095] Optionally, the anode 100 includes the following anode materials, preferably materials 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. A transparent electrode comprising indium tin oxide (ITO) as the anode is preferred.
[0096] Optionally, the hole transport layer includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not make special provisions for this. The hole transport layer material is selected from the group consisting of the following compounds:
[0097] In one embodiment, the hole transport layer 320 is compound HT-1.
[0098] In one embodiment, the luminescence adjustment layer 321 is an organic compound of the present application.
[0099] Alternatively, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. Alternatively, the organic light-emitting layer 330 may be composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may 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.
[0100] The main material of the organic light-emitting layer 330 can be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, which are not particularly limited in this application. The main material can be a single main material or a mixed main material.
[0101] In a specific embodiment, the main material of the organic light emitting layer 330 is RH-1
[0102] The guest material of the organic light-emitting layer 330 can be selected according to the prior art, for example, it can be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include but are not limited to:
[0103] In one embodiment, the guest material of the organic light-emitting layer 330 is RD-1.
[0104] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials. The electron transport material can generally include a metal complex and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring compound with a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-1, BimiBphen, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. Specific examples of the nitrogen-containing heterocyclic derivatives used for electron transport materials include but are not limited to:
[0105] In one specific embodiment, electron transport layer 340 is composed of ET-1 and LiQ.
[0106] In the present application, cathode 200 may include a cathode material having a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode containing magnesium and silver is used as the cathode.
[0107] Optionally, as shown in FIG1 , a hole injection layer 310 is further 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 made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:
[0108] In one embodiment, the hole injection layer 310 is HT-1 and PD-1.
[0109] Optionally, as shown in FIG1 , an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic compound. For example, the electron injection layer 350 includes ytterbium (Yb).
[0110] Optionally, a cathode covering layer is further provided on the cathode 200 .
[0111] In one specific embodiment, the cathode capping layer comprises Compound CP-1.
[0112] According to a specific embodiment, as shown in Figure 3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.
[0113] Alternatively, the photoelectric conversion device may be a solar cell, in particular an organic thin-film solar cell. For example, in one embodiment of the present application, the solar cell comprises an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer comprises the organic compound of the present application.
[0114] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.
[0115] According to one embodiment, as shown in FIG2 , the electronic device is a first electronic device 400, which includes the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.
[0116] According to another embodiment, as shown in FIG4 , the electronic device is a second electronic device 500, which includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.
[0117] The synthesis method of the organic compound of the present application is specifically described below with reference to synthesis examples, but the present application is not limited thereto.
[0118] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.
[0119] Synthesis example
[0120] 1. Synthesis of IM 3B2C-2:
[0121] (1) Under nitrogen protection, methyl 2,4-dibromo-5-chlorobenzoate (110.0 g, 334.98 mmol), phenylboric acid (40.8 g, 334.98 mmol), potassium carbonate (K2CO3, 101.8 g, 736.94 mmol), tetrakistriphenylphosphine palladium (Pd(PPh3)4, 7.74 g, 6.70 mmol) and tetrabutylammonium bromide (TBAB, 21.6 g, 6 7.00 mmol), then added solvents: toluene (800 mL), ethanol (400 mL) and water (200 mL), started stirring, heated to 70°C ~ 75°C and refluxed for 12 h. After the reaction was completed, cooled to room temperature and extracted with dichloromethane. After separation, the organic phase was washed with water until neutral, dried, filtered, and concentrated to obtain a crude product, which was then recrystallized from dichloromethane and petroleum ether to LC>98%, and dried to obtain IM 3B2C-1 (89.8 g, yield: 82.3%) as a white solid.
[0122] (2) Sodium hydroxide (63.4 g, 1584.82 mmol) was added to the reaction flask, and 1.2 L of deionized water was added to dissolve the sodium hydroxide. 1.2 L of methanol was then added, stirred evenly, and IM 3B2C-1 (86.0 g, 264.14 mmol) was added. The temperature was raised to 50°C to 55°C and the reaction was continued for 24 h. After the reaction, the reaction solution was concentrated under reduced pressure to remove the methanol, and then acidified to pH = 2-3 by adding dilute hydrochloric acid. The solution was extracted with dichloromethane and washed with deionized water until neutral. The organic phase was separated and dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under reduced pressure to remove the solvent to obtain IM 3B2C-2 (73.4 g, yield: 89.2%) as a white solid.
[0123] 2. Synthesis of IM 6B2C-3:
[0124] Under nitrogen protection, IM 6B2C-2 (CAS No: 1931440-55-9, 94.0 g, 301.71 mmol), oxalyl chloride (49.8 g, 392.22 mmol) and dichloromethane (700 mL) were added to the reaction flask in sequence. After stirring for 5 min, the solvent N,N-dimethylformamide (DMF, 0.66 g, 9.05 mmol) was added and stirred at room temperature for 18 h. The reaction solution was distilled under reduced pressure to remove excess oxalyl chloride and solvent to obtain IM 6B2C-3 (72.58 g, yield: 72.9%) as a yellow solid.
[0125] IM xByC-3 listed in Table 1 below was synthesized in the same manner as IM 6B2C-3, except that IM xByC-2 was used instead of IM 6B2C-2. The main raw materials used, the synthesized intermediates, and the yields are shown in Table 1.
[0126] Table 1
[0127] 3. Synthesis of IM 6B2C-4
[0128] Under nitrogen, IM 6B2C-3 (72.2 g, 218.79 mmol), anhydrous aluminum chloride (46.67 g, 350.06 mmol), and dry dichloromethane (700 mL) were added to a reaction flask and stirred at room temperature for 2 h. The reaction solution was poured into 1200 mL of cold water with stirring, extracted with dichloromethane, and washed with water several times until neutral. The mixture was then separated, dried, and filtered. The organic phase was purified by silica gel chromatography and concentrated under reduced pressure to provide IM 6B2C-4 (60.7 g, yield: 94.5%).
[0129] IM xByC-4 listed in Table 2 below was synthesized in the same manner as IM 6B2C-4, except that IM xByC-3 was used instead of IM 6B2C-3. The main raw materials used, the synthesized intermediates, and the yields are shown in Table 2.
[0130] Table 2
[0131] 4. Synthesis of IM 6B2C-9H-F1
[0132] Under nitrogen, iodine (36.47 g, 144.03 mmol), hypophosphorous acid (27.16 g, 411.53 mmol), and glacial acetic acid (600 mL) were added to a reaction flask. The mixture was stirred and heated to 100°C for 30 min. IM 6B2C-4 (60.4 g, 205.76 mmol) was then added and stirred for 8 h. The reaction was stopped, cooled to 40°C, and 1 L of deionized water was added and stirred thoroughly. The mixture was then extracted with 1 L of dichloromethane. The organic phase was washed with water until neutral, separated, dried, filtered, and concentrated under reduced pressure to remove the solvent. The resulting crude yellow solid was purified by silica gel chromatography using n-heptane as the eluent to obtain IM 6B2C-9H-Fl (52.8 g, yield: 91.8%).
[0133] IM xByC-9H-Fl listed in Table 3 below was synthesized using the same method as IM 6B2C-9H-Fl, except that xByC-4 was used instead of IM 6B2C-4. The main starting materials, synthesized intermediates, and yields are shown in Table 3.
[0134] Table 3
[0135] 5. Synthesis of IM 6B2C-CyHex-SF
[0136] IM 6B2C-9H-Fl (30.0 g, 107.31 mmol), 45 mL of 50 wt% aqueous sodium hydroxide solution (containing 34.34 g, 858.49 mmol of NaOH), and dimethyl sulfoxide (DMSO, 300 mL) were added to a reaction flask. Stirring was initiated and the mixture was heated to 160°C until the raw materials dissolved and cleared. Benzyltriethylammonium chloride (BTEAC, 0.5 g, 2.15 mmol) was then added. 1,5-Dibromopentane (24.7 g, 107.31 mmol) was then slowly added dropwise to the reaction system. After the addition was complete, the reaction was heated for 4 hours. The reaction was terminated by cooling to room temperature and extracting the reaction solution with toluene and water. The organic phase was then purified by silica gel chromatography. The column extract was then distilled under reduced pressure to yield IM 6B2C-CyHex-SF (35.1 g, 94.1% yield).
[0137] IM xByC-Cyw-SF (W = Hex or Pen or Hep) in Table 4 was prepared by the same method as IM 6B2C-CyHex-SF, except that IM xByC-9H-Fl was used instead of IM 6B2C-9H-Fl, and raw material 1 was used instead of 1,5-dibromopentane. The main raw materials used, the synthesized intermediates and their yields are listed in Table 4.
[0138] Table 4
[0139] 6. Synthesis of IM A1
[0140] Under nitrogen protection, IM 5B2C-CyHex-SF (28.0 g, 80.53 mmol), phenylboronic acid (10.31 g, 84.56 mmol), potassium carbonate (24.48 g, 177.17 mmol), tetrakistriphenylphosphine palladium (1.86 g, 1.61 mmol) and tetrabutylammonium bromide (TBAB, 5.19 g, 16.11 mmol) were added to the reaction flask, and then solvents: toluene (240 mL), ethanol (120 mL) and water (60 mL) were added. Stirring was started, and the temperature was raised to 70°C to 75°C and refluxed for 12 h. After the reaction was completed, the temperature was cooled to room temperature and extracted with dichloromethane. After separation, the organic phase was washed with water until neutral, dried, filtered, and concentrated to obtain a crude product, which was recrystallized from dichloromethane and petroleum ether to LC>98%, and dried to obtain a white solid, which is IM A1 (24.1 g, yield: 86.8%).
[0141] IM Ax in Table 5 was prepared by the same method as IM A1, except that xByC-CyW-SF (W = Hex or Pen or Hep) was used instead of IM 5B2C-CyHex-SF, and starting material 2 was used instead of phenylboronic acid. The main starting materials used, the synthesized intermediates and their yields are listed in Table 5.
[0142] Table 5
[0143] 7. Synthesis of IM A23-Bp
[0144] Under nitrogen protection, IM A23 (9.86 g, 28.59 mmol), pinacol diboronate (7.62 g, 30.02 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.52 g, 0.57 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-PHOS, 0.55 g, 1.15 mmol) and potassium acetate (KOAc, 5.61 g, 57.18 mmol) were added to 1,4-dioxane (90 mL), heated to 80°C and stirred for 8 h; then cooled to room temperature, the reaction solution was washed with water until neutral, separated and washed with water until neutral, the organic phases were combined, dried, filtered, and the solvent was removed under reduced pressure; the crude product was recrystallized and purified using ethyl acetate / petroleum ether (volume ratio of 1:3) to obtain a white solid IM A23-Bp (9.18 g, yield: 73.6%).
[0145] IM Ax-Bp in Table 6 was prepared by the same method as IM A23-Bp, except that IM Ax was used instead of IM A23. The main raw materials used, the synthesized intermediates and their yields are listed in Table 6.
[0146] Table 6
[0147] 8. Synthesis of IM A23-L
[0148] Under nitrogen, a reaction flask was added with IM A23-Bp (9.00 g, 20.62 mmol), p-chlorobromobenzene (3.95 g, 20.62 mmol), potassium carbonate (6.27 g, 45.37 mmol), tetrakis(triphenylphosphine)palladium (0.48 g, 0.41 mmol), tetrabutylammonium bromide (TBAB, 1.33 g, 4.12 mmol), toluene (80 mL), ethanol (40 mL), and water (20 mL). After addition, stirring was initiated and the mixture was heated to 70-75°C and refluxed for 12 h. After completion of the reaction, the temperature was cooled and the mixture was extracted with dichloromethane. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The mixture was then recrystallized from dichloromethane / petroleum ether and dried to obtain IM A23-L (6.6 g, 76.0% yield) as a white solid.
[0149] IM Ax-L in Table 7 was prepared using the same method as IM A23-L, except that IMAx-Bp was used instead of IM A23-Bp, and raw material 3 was used instead of p-chlorobromobenzene. The main raw materials used, the synthesized intermediates and their yields are listed in Table 7.
[0150] Table 7
[0151] 9. Synthesis of IM N1
[0152] Under nitrogen protection, 1-(3-bromophenyl)naphthalene (4.2 g, 14.83 mmol), 2-amino-9,9-dimethylfluorene (3.17 g, 15.14 mmol), tris(dibenzylideneacetone)dipalladium (0.14 g, 0.15 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-PHOS, 0.14 g, 0.30 mmol), sodium tert-butoxide (t-BuONa, 2.14 g, 22.25 mmol) and toluene (Toluene, 40 mL) were added to the reaction flask, the temperature was raised to 108°C, and the reaction mixture was stirred and refluxed for 2 h; then cooled to room temperature, the reaction solution was washed with water until neutral, and then dried over magnesium sulfate. After filtering, the filtrate was decompressed and the solvent was removed to obtain a crude yellow solid; the crude product was then recrystallized from toluene / petroleum ether to obtain IM N1 (4.97 g, yield: 81.4%).
[0153] IM Ny in Table 8 was prepared using the same method as IM N1, except that starting material 4 was used instead of 1-(3-bromophenyl)naphthalene, and starting material 5 was used instead of 2-amino-9,9-dimethylfluorene. The main starting materials used, the synthesized intermediates, and their yields are listed in Table 8.
[0154] Table 8
[0155] Synthesis Example 1: Synthesis of Compound 124
[0156] Under nitrogen, a reaction flask was charged with IM Al (4.0 g, 11.60 mmol), IM N9 (CAS No: 1609484-77-6, 4.61 g, 11.60 mmol), tris(dibenzylideneacetone)dipalladium (0.11 g, 0.12 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-PHOS, 0.10 g, 0.24 mmol), sodium tert-butoxide (1.67 g, 17.40 mmol), and toluene (40 mL). The reaction mixture was heated to 108°C and stirred under reflux for 4 h. The reaction mixture was then cooled to room temperature, washed with water until neutral, and dried over magnesium sulfate. The filtrate was filtered and the solvent removed under reduced pressure to yield a crude yellow solid. This crude product was then recrystallized from a toluene / ethyl acetate mixture to afford compound 124 (4.14 g, 50.6% yield). Mass spectrum (m / z) = 706.3 [M+H] + .
[0157] Compound X in Table 9 was prepared using the same method as compound 124, except that starting material 6 was used instead of IM A1, and starting material 7 was used instead of IM N9. The main starting materials used, the synthesized compound X, its yield, and mass spectrum are listed in Table 9.
[0158] Table 9
[0159] The NMR data of some compounds are shown in Table 10:
[0160] Table 10
[0161] Fabrication and evaluation of organic electroluminescent devices
[0162] Example 1: Red organic electroluminescent device
[0163] The anode was prepared by the following process: On the ITO / Ag / ITO experimental substrate, the surface was treated with ultraviolet, ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.
[0164] On the anode substrate, compounds HT-1 and PD-1 were co-evaporated at an evaporation rate ratio of 97%:3% to form a film with a thickness of hole injection layer.
[0165] Compound HT-1 was evaporated on the hole injection layer to form a layer with a thickness of hole transport layer.
[0166] Compound 4 is evaporated on the hole transport layer to form a layer with a thickness of Glow adjustment layer.
[0167] On the luminescence adjustment layer, compound RH-1 and compound RD-1 were co-evaporated at an evaporation rate ratio of 98%:2% to form a film with a thickness of organic light-emitting layer.
[0168] On the organic light emitting layer, compound ET-1 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form a film with a thickness of electron transport layer;
[0169] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated on the electron injection layer at an evaporation rate ratio of 10%:90% to form a thickness of cathode.
[0170] Finally, compound CP-1 is evaporated on the cathode to form a layer with a thickness of The cathode covering layer is formed, thereby completing the preparation of the red organic electroluminescent device.
[0171] Example 2 to Example 63:
[0172] An organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 11 was used instead of Compound 4 in Example 1 when preparing the luminescence adjustment layer.
[0173] Comparative Examples 1 to 5:
[0174] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A, Compound B, Compound C, Compound D, and Compound E were used instead of Compound 4 in Example 1 when preparing the luminescence adjustment layer.
[0175] In the preparation of the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:
[0176] The performance of the organic electroluminescent devices prepared in Examples 1 to 63 and Comparative Examples 1 to 5 was tested. Specifically, the performance of the organic electroluminescent devices prepared in Examples 1 to 63 and Comparative Examples 1 to 5 was tested. 2 The IVL performance (operating voltage, current efficiency and color coordinates) of the device was tested under the conditions of T95 device life at 30mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 11 below.
[0177] Table 11
[0178] Referring to Table 11 above, it can be seen that compared with the organic electroluminescent devices of Comparative Examples 1 to 5, the comprehensive performance of the organic electroluminescent devices of Examples 1 to 63 is effectively improved, mainly manifested in that the operating voltage of the device is reduced by at least 0.19 V, the current efficiency is increased by at least 18.31%, and the T95 life is increased by at least 15.21%.
[0179] The preferred embodiments of the present application are described in detail above. However, the present application is not limited to the specific details of the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection of the present application.
Claims
1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Among them, one of R1 and R2 is selected from the other is selected from H or D; n is selected from 1, 2, 3 or 4; L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents in L and Ar are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trideuterated methyl group or a phenyl group; L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; The substituents in L1, L2, L3, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.
2. The organic compound according to claim 1, characterized in that L is selected from a single bond or the group consisting of:
3. The organic compound according to claim 1, characterized in that Ar is selected from the group consisting of:
4. The organic compound according to claim 1, characterized in that L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms; Optionally, the substituents in L1, L2 and L3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms or a phenyl group.
5. The organic compound according to claim 1, characterized in that L1, L2 and L3 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group; Optionally, the substituents in L1, L2 and L3 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl.
6. The organic compound according to claim 1, characterized in that L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:
7. The organic compound according to claim 1, characterized in that L3 is selected from a single bond or the following groups:
8. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms; Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.
9. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of the following groups: The substituted group Q has one or more substituents, each substituent is the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
10. The organic compound according to claim 1, characterized in that The compound is selected from the group consisting of the following compounds:
11. 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 contains the organic compound according to any one of claims 1 to 10.
12. The electronic component according to claim 11, characterized in that The functional layer includes a luminescence adjustment layer, and the luminescence adjustment layer includes the organic compound according to any one of claims 1 to 10; Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device; Optionally, the organic electroluminescent device is a red organic electroluminescent device.
13. An electronic device, characterized in that The electronic component comprising claim 11 or 12.
Citation Information
Patent Citations
Fluorene derivative and electronic device
CN111056960A
Fluorene derivative and electronic device
CN111057005A
Fluorene group-containing triarylamine compound and organic electroluminescent device thereof
CN113788759A
Fluorene-based triarylated amine compound and application thereof in organic electroluminescent device
CN116041243A
Amine-containing compound, and light-emitting device, electronic apparatus, and electronic device including same
CN117126061A