Organic compound, and electronic element and electronic device using same

An organic compound with a dibenzo five-membered ring structure improves the efficiency and lifespan of organic electroluminescent devices by enhancing carrier mobility and molecular conjugation, addressing performance limitations in existing technologies.

CN119118846AActive Publication Date: 2024-12-13SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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Patent Information

Application Number
CN202310693446.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-06-12
Publication Date
2024-12-13
Estimated Expiration
2043-06-12

AI Technical Summary

Technical Problem

The efficiency, service life, and performance of organic electroluminescent devices need to be improved to meet current application requirements.

Method used

An organic compound with a specific structure, featuring a dibenzo five-membered ring with phenyl groups at positions 1 and 2 and an aromatic amine group at positions 3 or 4, is used as a hole transport material, enhancing spatial stereoscopic properties and molecular conjugation, improving carrier mobility and transmission efficiency, and preventing crystallization.

Benefits of technology

The compound improves carrier balance, widens the carrier recombination area, enhances exciton generation and utilization efficiency, and extends the device's service life.

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Abstract

The present application relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound has a structure as shown in a formula I. When the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #
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Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to an organic compound and an electronic component and an electronic device using the organic compound. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Such electronic components usually include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed 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.

[0003] Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence. When voltage is applied between the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, which are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0004] However, the efficiency, service life and other performance of organic electroluminescent devices need to be further improved compared with the application requirements of products. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0005] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0006] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0007]

[0008] Wherein, X is selected from O, S, C (R 1 R 2 ) or N(R 3 );

[0009] R 1 , R 2 and R 3 are the same or different and are each independently selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and optionally, R1 and R 2 Together with the carbon atom they are connected to, they form a saturated or unsaturated 5-13-membered ring;

[0010] L, L 1 and L 2 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;

[0011] Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] L, L 1 , L 2 ,Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl 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, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0013] Each R is 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;

[0014] n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

[0015] A second aspect of the present application provides 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; the functional layer comprises the above-mentioned organic compound.

[0016] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0017] The main structural feature of the compound of the present application is a dibenzo five-membered ring The same benzene ring is trisubstituted, wherein the substituents at positions 1 and 2 of the dibenzo pentacyclic ring are both phenyl, and the 3rd or 4th position is connected to an aromatic amine group. In this connection mode, on the one hand, the connection of phenyl groups at positions 1 and 2 of the dibenzo pentacyclic ring can enhance the spatial stereoscopic properties of the molecule and improve the carrier mobility of the compound; on the other hand, the connection of aromatic amine at positions 3 or 4 of the dibenzo pentacyclic ring increases the degree of molecular conjugation, effectively improves the transmission efficiency of the compound, and makes the compound have a high Tg, so that when the OLED device is driven, the compound can be prevented from crystallizing, thereby improving the service life of the device. When the compound of the present application is used as a hole transport material, the carrier balance in the organic light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device efficiency and life can be improved.

[0018] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] 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.

[0020] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0021] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0022] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0023] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0024] Description of Reference Numerals

[0025] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device DETAILED DESCRIPTION

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed 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, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0027] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0028]

[0029] Wherein, X is selected from O, S, C (R 1 R 2 ) or N(R 3 );

[0030] R 1 , R 2 and R 3 are the same or different and are each independently selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and optionally, R 1 and R 2 Together with the carbon atom they are connected to, they form a saturated or unsaturated 5-13-membered ring;

[0031] L, L 1 and L 2 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;

[0032] Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0033] L, L 1 , L 2 ,Ar 1 and Ar 2The substituents in are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl 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, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0034] Each R is 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;

[0035] n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

[0036] In the present application, the terms "optionally" and "optionally" mean that the event or environment described later can but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "optionally, two adjacent substituents form a ring" means that the two substituents can form a ring but do not have to form a ring, including: the situation where the two adjacent substituents form a ring and the situation where the two adjacent substituents do not form a ring.

[0037] In this application, the descriptions "each independently selected from" and "respectively independently selected from" are interchangeable and should be understood in a broad sense, which 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, which means: Formula Q-1 indicates 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 indicates 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.

[0038] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl having a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a deuterated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0039] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms. 1 If it is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents on the arylene group is 12.

[0040] In this application, "D" means deuterated.

[0041] 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, and two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include a dicyclic condensed aryl (e.g., naphthyl), a 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, etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0042] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, deuterated alkyl 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 in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0043] 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 may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0044] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, deuterated alkyl 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 in the heteroaryl group and the substituents on the heteroaryl group.

[0045] In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0046] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0047] 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 of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and 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.

[0048] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0049] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0050] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0051] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0052] In this application, an unpositioned connecting bond refers to a single bond extending from the ring system. 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. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0053]

[0054] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of 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 mode shown in formula (X'-1) to formula (X'-4):

[0055]

[0056] In some embodiments of the present application, the organic compound has a structure shown in the following Formula 1 to Formula 12:

[0057]

[0058]

[0059] In some embodiments of the present application, R 1 , R 2 and R3 are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, R 1 and R 2 The carbon atom to which they are connected together forms cyclopentane, cyclohexane, fluorene ring, norbornane or adamantane.

[0060] In some embodiments of the present application, each R is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0061] In some embodiments of the present application, L, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms. 1 and L 2 Each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0062] Optionally, L, L 1 and L 2 The substituents in are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0063] In some embodiments of the present application, L, L 1 and L 2 Each is 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 dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0064] Optionally, L, L 1 and L 2 The substituents in are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0065] In some embodiments of the present application, L, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0066]

[0067] In some embodiments of the present application, L is selected from a single bond or the following groups:

[0068]

[0069] In some embodiments of the present application, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0070]

[0071] In some embodiments of the present application, Ar 1 and Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. 1 and Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 10, 20, 21, 22, 23, 24 or 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0072] Optionally, Ar 1 and Ar 2 The substituents in are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

[0073] In some embodiments of the present application, Ar 1 and Ar 2 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthryl, substituted or unsubstituted cyclopentanespirofluorene, substituted or unsubstituted cyclohexanespirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.

[0074] Optionally, Ar 1 and Ar 2The substituents in are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0075] In some embodiments of the present application, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0076]

[0077] Further optionally, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0078]

[0079]

[0080] In some embodiments of the present application, and Each is independently selected from the group consisting of:

[0081]

[0082] In some embodiments of the present application, and Each is independently selected from the group consisting of:

[0083]

[0084]

[0085] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] 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 of the present application.

[0093] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound of the present application.

[0094] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device. Further optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0095] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer contains the organic compound of the present application.

[0096] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device may include a stacked anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340 and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.

[0097] Optionally, the anode 100 includes the following anode materials, which are 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0098] Optionally, the hole transport layer includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and this application does not make special provisions for this. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0099]

[0100] In a specific embodiment, the first hole transport layer 321 is compound HT-21.

[0101] Optionally, the second hole transport layer 322 is the compound of the present application.

[0102] Optionally, 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. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and 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.

[0103] 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, and the present application does not impose any special restrictions on this. The main material can be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is CBP.

[0104] 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) organic metal complex, platinum (II) organic metal complex, ruthenium (II) complex, etc. Specific examples of the guest material include, but are not limited to,

[0105]

[0106] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is Ir(piq) 2 (acac).

[0107] Optionally, the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport material may generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, LiQ, Alq 3 etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc., and specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-21, BimiBphen, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. In one embodiment of the present application, the electron transport layer 340 is composed of ET-21 and LiQ.

[0108]

[0109]

[0110] In the present application, cathode 200 may include cathode material, which is a material with 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, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.

[0111] Alternatively, if Figure 1 As shown, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any special restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0112]

[0113] In a specific embodiment of the present application, the hole injection layer 310 is HAT-CN.

[0114] Alternatively, if Figure 1 As shown, 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 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of alkali metals and organic matter. For example, the electron injection layer 350 includes LiQ.

[0115] According to another embodiment, the electronic component is a photoelectric conversion device. Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.

[0116] According to a specific implementation mode, Figure 3 As shown, 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 which are stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0117] Optionally, 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.

[0118] In a third aspect, the present application provides an electronic device, comprising the electronic component provided in the second aspect of the present application.

[0119] According to one embodiment, Figure 2 As shown, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0120] According to another embodiment, Figure 4 As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.

[0121] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0122] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0123] Synthesis example

[0124] 1. Synthesis of IM a-1:

[0125]

[0126] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and 2-carboxyphenylboronic acid (46.1 g, 277.82 mmol), reactant A (CAS: 2841677-13-0, 95.47 g, 277.82 mmol), bistriphenylphosphine palladium dichloride (0.975 g, 1.4 mmol), potassium carbonate (95.99 g, 694.56 mmol) were added in sequence, and a mixed solvent of ethylene glycol dimethyl ether (400 mL) and water (100 mL) was added. Stirring was started, the temperature was raised to 78°C to 80°C for reaction for 15 hours, and after the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM a-1 (72.03 g, yield 67.4%).

[0127] 2. Synthesis of IM b-1:

[0128]

[0129] Under nitrogen atmosphere, IM a-1 (48.11 g, 125 mmol) and sodium hydroxide aqueous solution (313 mL, 10 g, 250 mmol) were added to a clean 250 mL single-mouth bottle in sequence, and the system was gradually heated to reflux, and reacted overnight under reflux. After the reaction was completed, the heating was stopped and cooled to room temperature. 2 mol / L hydrochloric acid was added dropwise to the reaction solution to neutralize the system to acidity (pH = 1.0). During this period, a large amount of white solid was generated, which was collected by suction filtration and washed with water until neutral. The filter cake was dried at 80 ° C overnight to obtain a white solid. The above white solid was placed in a 1L two-mouth bottle, 250 g of polyphosphoric acid was added, mechanically stirred, gradually heated to 160 ° C, and reacted for 4 hours. After the reaction was completed, the heating was stopped, and the system was poured into a large beaker containing 1 kg of ice while stirring continuously while hot, and the system was neutralized to alkalinity with 1 mol / L sodium hydroxide solution. The solid was collected by suction filtration and washed with water until neutral. The filter cake was dried at 80°C overnight to obtain IMb-1 (29.9 g, yield 65.2%).

[0130] 3. Synthesis of IM c-1:

[0131]

[0132] Under nitrogen atmosphere, add iodine (5 g, 19.7 mmol) and glacial acetic acid (500 mL) to a three-necked flask equipped with a reflux condenser and a dropping funnel, stir to dissolve, then add hypophosphorous acid (19.5 g, 304.8 mmol), heat to 120°C, and react until the color of the system fades. Then add IM b-1 (27 g, 74 mmol) all at once, continue heating and reflux for 4 h, cool to room temperature, pour into water to precipitate a large amount of solid, and filter and collect the solid to obtain IM c-1 (21.2 g, yield 81.1%).

[0133] 4. Synthesis of IM d-1:

[0134]

[0135] Under nitrogen atmosphere, IM c-1 (21 g, 59.5 mmol) was transferred to a three-necked flask equipped with a dropping funnel, tetrahydrofuran (550 mL) was added, stirred to dissolve, and cooled with an ice-water bath. Under an ice bath, sodium tert-butoxide (21.6 g, 224.8 mmol) was added, and after stirring for 10 min, iodomethane (31.8 g, 224 mmol) was added. After the system was stirred for 30 min, the ice bath was removed, the temperature was raised to room temperature, and the reaction was continued at room temperature overnight. After the reaction was completed, the insoluble matter was removed by suction filtration, and the filtrate was concentrated to obtain a crude product, which was purified by column chromatography, and the eluent was petroleum ether: dichloromethane = 9: 1 (V / V) to obtain IM d-1 (17.8 g, yield 78.5%).

[0136] 5. Synthesis of IM e-1

[0137]

[0138] Nitrogen (0.100L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and the raw materials 1,3,4-tribromo-2,5-dichlorobenzene (50g, 130.3mmol), phenylboric acid (35g, 286.7mmol), tetrakis(triphenylphosphine)palladium (0.75g, 0.65mmol) and potassium carbonate (71.9g, 520.2mmol) were added in sequence, and a mixed solvent of toluene (400mL), ethanol (200ml) and water (100mL) was added. Stirring was started, the temperature was raised to 78℃~80℃ for reaction for 12h, and after the reaction was completed, it was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated, and the organic phase was dried with anhydrous magnesium sulfate. After filtering, the filtrate was decompressed and distilled to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain IM e-1 (20.7g, yield 42%).

[0139] IM e-2 listed in Table 1 was synthesized in the same manner as IM e-1, except that raw material 1 was used instead of 1,3,4-tribromo-2,5-dichlorobenzene, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 1:

[0140] Table 1

[0141]

[0142] 6. Synthesis of IM f-1

[0143]

[0144] A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was replaced with nitrogen (0.100 L / min) for 15 min, and IM e-1 (20 g, 52.9 mmol), o-hydroxyphenylboric acid (8 g, 58.0 mmol), tetrakis(triphenylphosphine)palladium (0.61 g, 0.53 mmol) and potassium carbonate (14.6 g, 105.8 mmol) were added in sequence, and a mixed solvent of toluene (160 mL), ethanol (80 ml) and water (40 mL) was added. Stirring was started, and the temperature was raised to 78°C to 80°C for reaction for 8 h. After the reaction was completed, it was cooled to room temperature. The reaction solution was washed with water, and the organic phase was separated. The organic phase was dried with anhydrous magnesium sulfate. After filtering, the filtrate was decompressed and distilled to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain IM f-1 (17 g, yield 82%).

[0145] IM fx listed in Table 2 was synthesized in the same manner as IM f-1, except that raw material 2 was used instead of IMe-1, and raw material 3 was used instead of o-hydroxyphenylboronic acid. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2:

[0146] Table 2

[0147]

[0148] 7. Synthesis of IM G-1

[0149]

[0150] Nitrogen (0.200L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and IM f-1 (17g, 43.4mmol), potassium carbonate (12g, 86.8mmol) and acetonitrile (150mL) were added in sequence, and refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature. The organic phase was extracted with dichloromethane and water, and anhydrous magnesium sulfate was added to dry the organic phase. After filtering, the filtrate was decompressed and distilled to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain IM G-1 (13.6g, yield 88%).

[0151] IM F-2 listed in Table 3 was synthesized in the same manner as IM F-1, except that IM F-2 was used instead of IM F-1, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 3:

[0152] Table 3

[0153]

[0154] 8. IM H-1

[0155]

[0156] Nitrogen (0.200 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 min, and IM f-3 (15 g, 34.3 mmol) and sulfuric acid (50 mL) were added in sequence. The reaction was refluxed for 6 h. After the reaction was completed, 500 mL of 1 mol / L NaOH solution was added and stirred for 1 h. The generated solid was filtered and recrystallized with toluene to obtain IM H-1 (11 g, yield 86%).

[0157] IM H-2 listed in Table 4 was synthesized in the same manner as IM H-1, except that IM f-4 was used instead of IM f-3, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 4:

[0158] Table 4

[0159]

[0160] 9. IM i-1

[0161]

[0162] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and the raw materials 2-nitrobenzeneboric acid (50.0 g, 277.82 mmol), reactant A (95.47 g, 277.82 mmol), bistriphenylphosphine palladium dichloride (0.975 g, 1.4 mmol) and potassium carbonate (95.99 g, 694.56 mmol) were added in sequence, and a mixed solvent of ethylene glycol dimethyl ether (400 mL) and water (100 mL) was added. Stirring was started, the temperature was raised to 78°C to 80°C for reaction for 15 hours, and after the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM i-1 (72.03 g, yield 65%).

[0163] IMj-1 listed in Table 5 was synthesized in the same manner as IM i-1, except that raw material 4 was used instead of reactant A, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 5:

[0164] Table 5

[0165]

[0166]

[0167] 10. IM i-2

[0168]

[0169] IM i-1 (72 g, 186.6 mmol), triphenylphosphine (122.35 g, 466.5 mmol) and o-dichlorobenzene (720 mL) were added to a flask, heated to 175 ° C under nitrogen protection, stirred for 18 hours and then cooled to room temperature, the reaction solution was washed with water, separated, the organic phase was washed with water and then dried over anhydrous magnesium sulfate, and the solvent was removed under high temperature and reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane system to obtain a white solid IM i-2 (56.78 g, yield 88%).

[0170] IMj-2 listed in Table 6 was synthesized in the same manner as IM i-2, except that IMj-1 was used instead of IMi-1, wherein the main raw materials used, the synthesized intermediates and their yields are shown in Table 6:

[0171] Table 6

[0172]

[0173] 11. IM I-1

[0174]

[0175] IM i-2 (50 g, 141.3 mmol), bromobenzene (22.18 g, 141.3 mmol), cuprous iodide (2.69 g, 14.1 mmol), potassium carbonate (48.8 g, 353.3 mmol), 1,10-phenanthroline (5.6 g, 28.3 mmol), 18-crown-6-ether (3.7 g, 14.1 mmol) and dimethylformamide (50 mL) were added to a flask, heated to 130°C under nitrogen protection, and stirred for 12 h. The temperature was cooled to room temperature, and dichloromethane (500 mL) and water were added to the reaction solution, and the liquid was separated. The organic phase was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system, and then recrystallized and purified using a toluene / n-heptane system to obtain a white solid IM i-1 (30.37 g, yield 50%).

[0176] IM J-1 listed in Table 7 was synthesized in the same manner as IM I-1, except that IMj-2 was used instead of IMi-2. The main raw materials used, the synthesized intermediates and their yields are shown in Table 7.

[0177] Table 7

[0178]

[0179] 12. Synthesis of Compound A-1-3

[0180]

[0181] Into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser, nitrogen (0.200 L / min) was introduced for replacement for 15 min, and 3-bromo-9,9-dimethyl-1,2-diphenyl-9H-fluorene (5 g, 11.8 mmol), di(4-biphenyl)amine (3.8 g, 11.8 mmol), tris(dibenzylideneacetone)dipalladium (0.11 g, 0.12 mmol), 2-bis(dicyclohexylphosphine)-2',6'-dimethoxybiphenyl (0.1 g, 0.24 mmol), sodium tert-butoxide (1.7 g, 17.7 mmol) and toluene (50 mL) were added in sequence. The mixture was refluxed at 105°C to 110°C for 4 h. After the reaction was completed, the mixture was cooled to room temperature. The organic phase was washed with water, and anhydrous magnesium sulfate was added to dry the organic phase. After filtering, the filtrate was distilled under reduced pressure to remove the solvent; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid product compound A-1-3 (5.4 g, yield 69%); mass spectrum (m / z) = 666.31 [M+H] + .

[0182] The compounds listed in Table 8 below were synthesized by the same method as compound A-1-3, except that raw material 5 was used instead of 3-bromo-9,9-dimethyl-1,2-diphenyl-9H-fluorene, and raw material 6 was used instead of di(4-biphenyl)amine. The main raw materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 8.

[0183] Table 8

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190] The NMR data of some compounds are shown in Table 9 below

[0191] Table 9

[0192]

[0193] Example 1: Preparation of red organic electroluminescent device

[0194] The anode was prepared by the following process: The ITO / Ag / ITO substrate was cut into 40 mm (length) × 40 mm (width) × 0.7 mm (thickness) dimensions and prepared into an experimental substrate with cathode and insulating layer patterns using a photolithography process. 2 :N 2 Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0195] HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of A hole injection layer of 100 mm thick was formed by vacuum evaporating HT-21 on the hole injection layer. The first hole transport layer is formed by a plurality of holes.

[0196] Compound A-1-3 is vacuum-deposited on the first hole transport layer to form a layer with a thickness of The second hole transport layer is

[0197] On the second hole transport layer, CBP and Ir(piq)2 (acac) is co-evaporated at an evaporation rate ratio of 95%:5% to form a film with a thickness of of an organic light-emitting layer.

[0198] On the organic light-emitting layer, ET-21 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of LiQ is vacuum 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 1:9 to form a layer with a thickness of cathode.

[0199] In addition, CP-1 is evaporated on the cathode to form a layer with a thickness of A cover layer (CPL) is formed on the organic light-emitting device to complete the manufacturing process.

[0200] Embodiments 2 to 35

[0201] An organic electroluminescent device was prepared by the same method as in Example 1, except that when forming the second hole transport layer, the compound shown in Table 11 was used instead of compound A-1-3.

[0202] Comparative Examples 1 to 3

[0203] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A-1-3 was replaced by compound A, B, and C when forming the second hole transport layer.

[0204] The main material structures used in the above embodiments and comparative examples are shown in Table 10 below:

[0205] Table 10

[0206]

[0207] The performance of the devices prepared in the examples and comparative examples was tested, wherein the IVL (operating voltage, current efficiency, color coordinates) data were obtained at 10 mA / cm 2 Tested under current density, T95 life is 20mA / cm 2 The results are shown in Table 11.

[0208] Table 11

[0209]

[0210]

[0211] According to the results in Table 11, the current efficiency of Examples 1 to 35 using the organic compound of the present invention as the second hole transport material in the red organic electroluminescent device is improved by at least 10.63% and the life is improved by at least 11.2% compared with Comparative Examples 1 to 4 corresponding to the known compounds.

[0212] Therefore, the compound has the characteristic of improving luminous efficiency. The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings, but the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, the technical solution of the present application can be subjected to a variety of simple modifications, and these simple modifications all belong to the protection scope of the present application.

[0213] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula I: Wherein, X is selected from O, S, C(R1R2) or N(R3); R1, R2 and R3 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and optionally, R1 and R2 form a saturated or unsaturated 5-13 membered ring with the carbon atom to which they are commonly attached; L, L1 and L2 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 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl 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, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; Each R is 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; n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

2. The organic compound according to claim 1, wherein Each R is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.

3. The organic compound according to claim 1, wherein R1, R2 and R3 are the same or different and are independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, R1 and R2 form cyclopentane, cyclohexane, fluorene ring, norbornane or adamantane with the carbon atom to which they are connected.

4. The organic compound according to claim 1, wherein L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms; The substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

5. The organic compound according to claim 1, wherein L, L1 and L2 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; The substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

6. The organic compound according to claim 1, wherein Ar1 and Ar2 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 18 carbon atoms; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

7. The organic compound according to claim 1, wherein 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 fluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthryl, substituted or unsubstituted cyclopentanespirofluorene, substituted or unsubstituted cyclohexanespirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

8. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the group consisting of:

9. The organic compound according to claim 1, wherein Each is independently selected from the group consisting of:

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

11. An electronic component, characterized in that The electronic component comprises an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 10.

12. The electronic component according to claim 11, wherein The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound; 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 device comprises the electronic component according to claim 11 or 12.

Citation Information

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