Organic compound, electronic element using same, and electronic device

Abstract

The present application relates to an organic compound, an electronic element using same, and an electronic device. The organic compound has a structure as shown in formula I. The organic compound is applied to an organic electroluminescent device, remarkably improving the performance of the device.

Description

Organic compound and electronic component and electronic device using the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202410310920.7 filed on March 18, 2024. The full text of the above Chinese patent application is hereby cited as part of this application. Technical Field

[0003] 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 same. Background Art

[0004] With the development of electronic technology and advancements in materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly widespread. Such electronic components generally include a cathode and an anode arranged in opposite directions, and a functional layer disposed between the cathode and the anode. This 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.

[0005] Taking an organic electroluminescent device as an example, it generally comprises an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode, stacked in sequence. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side migrate toward the organic light-emitting layer, and holes on the anode side also migrate toward the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, causing the organic light-emitting layer to emit light outward.

[0006] In the prior art, WO2016087017A1, KR1020110110508A, CN111094234A, etc. disclose materials that can be used in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the Invention

[0007] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same, wherein the organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0008] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0009] wherein, ring A is a naphthalene ring;

[0010] X is selected from C(R'R"), N(R), O or S;

[0011] Ar1 and Ar 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 20 carbon atoms;

[0012] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0013] The substituents in Ar1, Ar, L, L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms;

[0014] R', R", and R are the same or different and are each independently selected from 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, or an aryl group having 6 to 20 carbon atoms; or R' and R", together with the carbon atom to which they are attached, form a saturated or unsaturated 5-13 membered ring;

[0015] R1, R2, R3 and R4 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 trialkylsilyl group having 3 to 12 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0016] n1 is the number of R1, n1 is selected from 0, 1, 2, 3, 4 or 5, when n1 is greater than 1, any two R1 are the same or different;

[0017] n2 is the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different;

[0018] n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4, when n3 is greater than 1, any two R3 are the same or different;

[0019] n4 is the number of R4, and n4 is selected from 0, 1, 2 or 3. When n4 is greater than 1, any two R4 are the same or different.

[0020] A 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 above-mentioned organic compound.

[0021] A third aspect of the present application provides an electronic device comprising the electronic component described in the second aspect of the present application.

[0022] The compound of the present invention uses a large planar benzo-fused carbazole as the conjugated center, a benzene substituent connected to one side of the fused ring, and a dibenzo pentacyclic substituted aromatic amine connected to the other side. Due to the large conjugated center, the T1 energy level of the molecule is more suitable for use in red light devices. The introduction of the substituent can improve problems such as material crystallization caused by the large planar structure, thereby improving the life of the material. The dibenzo pentacyclic substituted aromatic amine group can ensure that the material has a high carrier mobility, thereby effectively regulating the transmission and injection of holes in the device. The "double-plane" structure formed with the benzocarbazole planar mother core more effectively blocks electrons, thereby improving the efficiency of the device.

[0023] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] 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.

[0025] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0026] FIG2 is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0027] FIG3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

[0028] FIG4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0029] DESCRIPTION OF NUMERALS 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

[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 I:

[0032] wherein, ring A is a naphthalene ring;

[0033] X is selected from C(R'R"), N(R), O or S;

[0034] Ar1 and Ar 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 20 carbon atoms;

[0035] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0036] The substituents in Ar1, Ar, L, L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms;

[0037] R', R' and R' are the same or different and are each independently selected from 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, or an aryl group having 6 to 20 carbon atoms; or R' and R'', together with the carbon atom to which they are attached, form a saturated or unsaturated 5-13 membered ring;

[0038] R1, R2, R3 and R4 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 trialkylsilyl group having 3 to 12 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0039] n1 is the number of R1, n1 is selected from 0, 1, 2, 3, 4 or 5, when n1 is greater than 1, any two R1 are the same or different;

[0040] n2 is the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different;

[0041] n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4, when n3 is greater than 1, any two R3 are the same or different;

[0042] n4 is the number of R4, and n4 is selected from 0, 1, 2 or 3. When n4 is greater than 1, any two R4 are the same or different.

[0043] In this application, the descriptions “each independently selected from” and “respectively 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.

[0044] 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 the substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0045] 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.

[0046] 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 (such as 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, 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 of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as 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.

[0047] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are substituted by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in 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.

[0048] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof that includes at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic condensed ring. For 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 triazinyl 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 silafluorenyl 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.

[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 a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. 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, etc. 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, 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, and specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0051] 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, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0052] 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.

[0053] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0054] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0055] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0056] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0057] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentanyl, cyclohexanyl, and adamantyl.

[0058] In this application, a non-positioned connecting bond refers to a single bond extending from the ring system. This means that one end of the link can be connected to any position in the ring system that the link 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 via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0059] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0060] In some embodiments of the present application, the organic compound of the present application is selected from the structure shown in the following formula I-1, formula I-2 or formula I-3:

[0061] In some embodiments of the present application, R', R" and R are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, trifluoromethyl, phenyl, naphthyl or biphenyl; or R' and R" together with the carbon atom to which they are connected form a cyclopentane ring. Cyclohexane ring or fluorene ring

[0062] In some embodiments of the present application, R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0063] In some embodiments of the present application, Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. For example, Ar is selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0064] In some embodiments of the present application, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0065] In some embodiments of the present application, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0066] In some embodiments of the present application, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0067] In some embodiments of the present application, Ar is selected from the group consisting of:

[0068] In some embodiments of the present application, Ar is selected from the group consisting of:

[0069] In some embodiments of the present application, 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 3 to 18 carbon atoms. For example, L, L1 and L2 are each 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 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0070] In some embodiments of the present application, 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.

[0071] In some embodiments of the present application, 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 dibenzothiophenylene group, or a substituted or unsubstituted carbazolyl group.

[0072] In some embodiments of the present application, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0073] In some embodiments of the present application, L, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0074] In some embodiments of the present application, L and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0075] In some embodiments of the present application, L1 is selected from a single bond or the group consisting of the following groups:

[0076] In some embodiments of the present application, Ar1 is 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. For example, Ar1 is 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, or 18 carbon atoms.

[0077] In some embodiments of the present application, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0078] In some embodiments of the present application, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0079] In some embodiments of the present application, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0080] In some embodiments of the present application, Ar1 is selected from the group consisting of:

[0081] In some embodiments of the present application, Ar1 is selected from the group consisting of:

[0082] In some embodiments of the present application, Selected from the group consisting of:

[0083] In some embodiments of the present application, Selected from the group consisting of:

[0084] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0085] 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 disposed between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0086] In some embodiments of the present application, the functional layer includes an organic light-emitting layer and a hole transport layer, the organic light-emitting layer includes the organic compound and / or the hole transport layer includes the organic compound.

[0087] In some embodiments of the present application, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0088] In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device.

[0089] Furthermore, in some embodiments of the present application, 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 includes the organic compound of the present application.

[0090] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1 , 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 the hole transport layer 320.

[0091] In some embodiments of the present application, 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 alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, the transparent electrode comprising indium tin oxide (ITO) is used as the anode.

[0092] In some embodiments of the present application, 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. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0093] In a specific embodiment, the first hole transport layer 321 is HT-21; and the second hole transport layer 322 is the compound of the present application.

[0094] In some embodiments of the present application, 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. In some embodiments of the present application, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 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.

[0095] The host 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 this application does not impose any specific restrictions on this. The host material can be a single host material or a mixture of host materials. In one embodiment of the present application, the host material of the organic light-emitting layer 330 is the compound of the present application and RH-N. In another embodiment of the present application, the host material of the organic light-emitting layer 330 is RH-P1 and RH-N1.

[0096] 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,

[0097] In one embodiment of the present application, the guest material of the organic light emitting layer 330 is RD-1

[0098] In some embodiments of the present application, 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 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. 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.

[0099] 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. A metal electrode comprising magnesium and silver is preferred as the cathode.

[0100] In some embodiments of the present application, as shown in FIG1 , a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. 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:

[0101] In a specific embodiment of the present application, the hole injection layer 310 is PD and HT-21.

[0102] In some embodiments of the present application, 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 340. 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 Yb.

[0103] According to another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG3 , the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite 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 this application.

[0104] 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. In some embodiments of the present application, the hole transport layer 320 includes the organic compound of the present application.

[0105] In some embodiments of the present application, the photoelectric conversion device may be a solar cell, and in particular, may be an organic thin-film solar cell. For example, in one embodiment of the present application, the solar cell includes 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 includes the organic compound of the present application.

[0106] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0111] Synthesis example

[0112] 1. Synthesis of intermediate IN-Np-P1-Br

[0113] Under nitrogen protection, 8-bromo-1-iodonaphthalene (50.0 g, 150.16 mmol), phenyl-D5-boric acid (19.1 g, 150.45 mmol), potassium carbonate (45.7 g, 330.40 mmol), tetrakis(triphenylphosphine)palladium (3.5 g, 3.03 mmol) and tetrabutylammonium bromide (9.7 g, 30.03 mmol) were added to the reaction bottle, and then solvent toluene (500 mL) and ethanol were added. (250mL) and deionized water (150mL), start stirring, heat to 70°C ~ 75°C reflux reaction for 12h, after the reaction is completed, cool, extract with dichloromethane, separate the liquid and wash the organic phase with water until neutral, then dry, filter and concentrate to obtain a crude product, and recrystallize the crude product with ethyl acetate and cyclohexane to LC>98%, and dry to obtain the intermediate IN-Np-P1-Br (28.9g, yield 66.8%) as a white solid.

[0114] The intermediates IN-Np-Px-Br (x is 2 to 5) listed in Table 1 were synthesized with reference to the preparation method of IN-Np-P1-Br, except that raw material 1 was used instead of 8-bromo-1-iodonaphthalene, and raw material 2 was used instead of phenyl-D5-boric acid. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 1:

[0115] Table 1

[0116] 2. Synthesis of intermediate IN-Np-P1-BA

[0117] Under nitrogen protection, the intermediate IN-Np-P1-Br (28.0 g, 97.15 mmol) and tetrahydrofuran (300 mL) were added to a three-necked flask, stirred and dissolved evenly, and then cooled to -78 ° C. Then, a 2.0 M n-butyl lithium / n-hexane solution (55 mL, 110.00 mmol) was slowly added dropwise. After the dropwise addition, the mixture was kept warm and stirred for 1 h. Then, trimethyl borate (11.4 g, 110.00 mmol) was added and kept warm and stirred for 30 min. Then, the temperature was naturally raised to room temperature and stirred overnight. The pH was adjusted to 5-6 with 1 mol / L dilute hydrochloric acid, and stirring was continued for 1 h. The aqueous layer was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure. The resulting solid was washed with toluene and dried to give the intermediate IN-Np-P1-BA (15.3 g, yield 62.2%).

[0118] The intermediates IN-Np-Px-BA (x is 2 to 4) listed in Table 2 were synthesized by referring to the preparation method of IN-Np-P1-BA, except that IN-Np-Px-Br was used instead of IN-Np-P1-Br. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2:

[0119] Table 2

[0120] 3. Synthesis of intermediate IN-Cz-A1

[0121] (1) Under nitrogen protection, 4-phenyl-1-naphthaleneboronic acid (38.4 g, 154.78 mmol), 2,4-dichloronitrobenzene (29.72 g, 154.78 mmol), potassium carbonate (47.1 g, 340.52 mmol), tetrakis(triphenylphosphine)palladium (3.58 g, 3.10 mmol) and tetrabutylammonium bromide (9.98 g, 30.96 mmol) were added to the reaction flask, and then the solvent toluene (36 0mL), ethanol (180mL) and deionized water (80mL), start stirring, heat to 70°C ~ 75°C reflux reaction for 8h. After the reaction is completed, cool, extract with toluene, separate the liquids, wash the organic phase with water until neutral, and then dry, filter, and concentrate to obtain a crude product, which is then recrystallized from ethyl acetate and petroleum ether to LC>98%, and dried to obtain the intermediate IN-Cz-a1 (40.32 g, yield 72.4%) as a light yellow solid.

[0122] (2) Under nitrogen protection, the intermediate IN-Cz-a1 (40.0 g, 111.17 mmol), triphenylphosphine (72.9 g, 277.94 mmol) and o-dichlorobenzene (ODCB, 350 mL) were added sequentially to a three-necked flask and stirred at 160°C for 18 h. The reaction was stopped and then the o-dichlorobenzene was removed by distillation under reduced pressure. The resulting black solid was extracted three times with cyclohexane by heating. The combined extracts were passed through a silica gel column and the solvent was removed by distillation under reduced pressure to obtain the intermediate IN-Cz-A1 (25.8 g, yield 70.8%) as a silvery white solid.

[0123] Intermediates IN-Cz-Ax (x is 2 to 14) listed in Table 3 were synthesized by referring to the preparation method of intermediate IN-Cz-A1, except that raw material 3 was used instead of 4-phenyl-1-naphthaleneboronic acid, and raw material 4 was used instead of 2,4-dichloronitrobenzene. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 3:

[0124] Table 3

[0125] 4. Synthesis of intermediate IN-Cz-B1

[0126] (1) Under nitrogen protection, 2-bromo-6-phenylnaphthalene (33.5 g, 118.30 mmol), 2,5-dichloroaniline (19.2 g, 118.54 mmol), tris(dibenzylideneacetone)dipalladium (2.17 g, 2.37 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (2.26 g, 4.74 mmol), sodium tert-butoxide (17.03 g, 177.22 mmol) and toluene (320 mL) were added to the reaction flask, stirred, heated to 108 ° C for 2 h; then cooled to room temperature, the reaction solution was washed with water and dried over anhydrous magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent to obtain a yellow solid crude product; the crude product was then recrystallized from toluene to obtain the intermediate IN-Cz-b1 (33.6 g, yield 78.0%).

[0127] (2) Under nitrogen protection, the intermediate IN-Cz-b1 (33.0 g, 90.59 mmol), cesium carbonate (35.4 g, 108.70 mmol), tricyclohexylphosphine tetrafluoroborate (6.7 g, 18.21 mmol), palladium acetate (2.1 g, 9.27 mmol) and N,N-dimethylacetamide (320 mL) were added to the reaction flask, stirring was started, and the mixture was heated to 160°C~163°C for reaction for 12 h; then the mixture was naturally cooled to 70°C, and the reaction solution was extracted with toluene and water. The organic phase was washed with deionized water until neutral, and then separated, dried, and filtered. The obtained filtrate was distilled under reduced pressure to remove the solvent to obtain a yellow solid crude product; the crude product was then recrystallized and purified using toluene / petroleum ether to obtain the intermediate IN-Cz-B1 (20.4 g, yield 68.7%).

[0128] The intermediates IN-Cz-Bx (x is 2 to 7) listed in Table 4 were synthesized by referring to the preparation method of IN-Cz-B1, except that raw material 5 was used instead of 2-bromo-6-phenylnaphthalene, and raw material 6 was used instead of 2,5-dichloroaniline. The main raw materials used, the synthesized intermediates and their yields are shown in Table 4:

[0129] Table 4

[0130] 5. Synthesis of intermediate IN-Cz-C1

[0131] Under nitrogen, IN-Cz-A1 (15.0 g, 45.76 mmol), bromobenzene (7.9 g, 50.33 mmol), cuprous iodide (0.2 g, 1.05 mmol), potassium carbonate (12.65 g, 91.52 mmol), 1,10-phenanthroline (4.12 g, 22.87 mmol), and 18-crown-6 (0.12 g, 0.46 mmol) were added to a 1L three-necked flask. Then, 150 mL of DMF was added, and the temperature was slowly raised to reflux and stirred for 24 hours. The reaction mixture was cooled to room temperature, added to 500 mL of water to remove the DMF, and extracted with dichloromethane. The mixture was dried over anhydrous magnesium sulfate for 30 minutes, and the solvent was evaporated under reduced pressure. The intermediate IN-Cz-C1 (13.82 g, 74.8%) was purified by silica gel column chromatography using dichloromethane / petroleum ether (volume ratio 1:2) to obtain the intermediate as an off-white solid.

[0132] The intermediates IN-Cz-Cx (x is 2 to 27) listed in Table 5 were synthesized by referring to the preparation method of IN-Cz-C1, except that raw material 7 was used instead of intermediate IN-Cz-A1, and raw material 8 was used instead of bromobenzene. The main raw materials used, the synthesized intermediates and their yields are shown in Table 5:

[0133] Table 5

[0134] 6. Synthesis of intermediate IN-Cz-C10-L

[0135] (1) Under nitrogen protection, the intermediate IN-Cz-C10 (10.0 g, 24.76 mmol), bipyraclostrobin (6.6 g, 25.99 mmol), tris(dibenzylideneacetone)dipalladium (0.45 g, 0.49 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.47 g, 0.99 mmol) and potassium acetate (4.86 g, 49.52 mmol) was added to 1,4-dioxane (100 mL), heated to 80°C and stirred for 8 h; then cooled to room temperature, the reaction solution was washed with water until neutral, and after separation, 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 the intermediate IN-Cz-C10-Bp (8.0 g, yield 65.2%) as a white solid.

[0136] (2) Under nitrogen protection, the intermediate IN-Cz-C10-Bp (7.8 g, 15.74 mmol), p-chlorobromobenzene (3.0 g, 15.74 mmol), potassium carbonate (4.8 g, 34.64 mmol), tetrakis(triphenylphosphine)palladium (0.4 g, 0.35 mmol), tetrabutylammonium bromide (TBAB, 1.02 g, 3.15 mmol), toluene (80 mL), ethanol (40 mL), and deionized water (20 mL) were added to the reaction flask. After the addition was complete, stirring was started and the mixture was heated to 70°C to 75°C and refluxed for 12 h. After the reaction was completed, the temperature was lowered 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 purified by recrystallization from toluene / petroleum ether and dried to obtain the intermediate IN-Cz-C10-L (5.1 g, 67.5%) as a white solid.

[0137] The intermediate IN-Cz-Cx-L (x is 18 or 26) in Table 6 was synthesized by referring to the preparation method of the intermediate IM-Cz-C10-L, except that the intermediate IN-Cz-Cx was used to replace IN-Cz-C10 to prepare IN-Cz-Cx-Bp; which was then used to replace the intermediate IN-Cz-C10-Bp, and the raw material 9 was used to replace p-chlorobromobenzene. The main raw materials used, the synthesized intermediates and their yields are shown in Table 6:

[0138] Table 6

[0139] 7. Synthesis of intermediate IN-NH-1

[0140] Under nitrogen protection, 3-bromo-dibenzothiophene (8.0 g, 30.40 mmol), 3,4-diphenylaniline (7.6 g, 31.16 mmol), tris(dibenzylideneacetone)dipalladium (0.56 g, 0.61 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.58 g, 1.22 mmol), sodium tert-butoxide (4.38 g, 45.60 mmol) and toluene (80 mL) were added to the reaction flask, and stirring was started. The mixture was heated to 108 ° C. and reacted for 2 h; then cooled to room temperature, the reaction solution was washed with water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was decompressed and the solvent was removed from the filtrate to obtain a yellow solid crude product; the crude product was then recrystallized and purified using toluene / petroleum ether to obtain the intermediate IN-NH-1 (10.2 g, yield 78.5%).

[0141] The intermediates IN-NH-x (x is 2 to 19) listed in Table 7 were synthesized by referring to the preparation method of IN-NH-1, except that raw material 10 was used instead of 3-bromo-dibenzothiophene, and raw material 11 was used instead of 3,4-diphenylaniline. The main raw materials used, the synthesized intermediates and their yields are shown in Table 7:

[0142] Table 7

[0143] Synthesis Example 1: Synthesis of Compound 7

[0144] Under nitrogen, the intermediate IN-Cz-C1 (6.00 g, 14.85 mmol), the starting material Sub-NH-1 (4.6 g, 14.85 mmol), tris(dibenzylideneacetone)dipalladium (0.14 g, 0.15 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.12 g, 0.30 mmol), and sodium tert-butoxide (2.14 g, 22.28 mmol) were added to toluene (50 mL) and heated to 108°C with stirring for 4 hours. The mixture was then cooled to room temperature, washed with water until neutral, dried over magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent. The crude product was recrystallized from toluene / cyclohexane to obtain compound 7 (4.98 g, 49.6% yield) as a white solid. Mass spectrum (m / z) = 677.3 [M+H] + .

[0145] The compounds in Table 8 were synthesized by referring to the preparation method of compound 7, except that raw material 12 was used instead of IN-Cz-C1, and raw material 13 was used instead of Sub-NH-1. The main raw materials used, the synthesized compounds, their yields and mass spectra are shown in Table 8.

[0146] Table 8

[0147] Compound 7: 1 H-NMR (CD2Cl2, 400MHz) δppm: 8.09-8.01 (m, 3H), 7.98-7.74 (m, 9H), 7.67 (s, 1H), 7. 59-7.34(m,14H),7.26(s,1H),7.14(d,1H),7.03(d,1H),6.94(s,1H),6.79(d,1H).

[0148] Compound 128: 1 H-NMR (CD2Cl2, 400MHz) δppm: 8.02-7.93 (m, 4H), 7.81-7.76 (m, 2H), 7.69-7.50 (m, 12H), 7.49-7. 41(m,9H),7.40-7.34m(m,3H),7.24(s,1H),7.08(d,1H),6.92(d,2H),6.78(s,1H),6.65(d,1H).

[0149] Compound 477: 1 H-NMR (CD2Cl2, 400MHz) δppm: 8.39 (s, 1H), 8.02-7.87 (m, 6H), 7.68-7.64 (m, 3H), 7.58-7.33 (m, 16H), 7.30 (d, 2H ),7.26(s,1H),7.23(d,1H),7.19-7.14(m,3H),7.07(s,1H),7.04(d,1H),6.92(d,1H),6.78(d,1H),6.76(s,1H).

[0150] Example 1: Red organic electroluminescent device

[0151] The device was prepared by the following process

[0152] When the thickness of ITO / Ag / ITO is On the experimental substrate, ultraviolet, ozone and O2:N2 plasma are used for surface treatment to increase the work function of the anode, and organic solvents can be used to clean the surface of the experimental substrate to remove impurities and oil stains on the surface of the experimental substrate.

[0153] Compound HT-21 and PD were co-evaporated on the experimental substrate at an evaporation rate ratio of 98%:2% to form a film with a thickness of The hole injection layer is then deposited with compound HT-21 to form a hole injection layer with a thickness of Compound 7 is evaporated on the hole transport layer to form a hole transport layer with a thickness of a second hole transport layer.

[0154] Next, on the second hole transport layer, compound RH-N1, compound RH-P1 and RD-1 were co-evaporated at an evaporation rate ratio of 65%:35%:2% to form a layer with a thickness of red light emitting layer.

[0155] On the red light emitting layer, compound ET-21 and LiQ were co-evaporated at an evaporation rate ratio of 50%:50% to form a layer with a thickness of electron transport layer;

[0156] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were co-evaporated on the electron injection layer at an evaporation rate ratio of 10%:90% to form a thickness of cathode.

[0157] 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.

[0158] Example 2 to Example 42:

[0159] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 9 was used instead of Compound 7 in Example 1 when preparing the second hole transport layer.

[0160] Comparative Example 1 to Comparative Example 3:

[0161] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 9 was used instead of Compound 7 in Example 1 when preparing the second hole transport layer.

[0162] Among them, when preparing the devices of the above embodiments and comparative examples, the compound structures used are as follows

[0163] The performance of the red organic electroluminescent devices prepared in Examples 1-42 and Comparative Examples 1-3 was tested. Specifically, at 10 mA / cm 2 The IVL performance (driving voltage, current efficiency) of the device was tested under the conditions of 20mA / cm 2 The T95 device life was tested under the conditions of , and the test results are shown in Table 9 below.

[0164] Table 9

[0165] As shown in Table 9 above, compared with the organic electroluminescent devices of Comparative Examples 1-3, the performance of the organic electroluminescent devices of Examples 1-42 is greatly improved, with the luminous efficiency increased by at least 12.2% and the T95 lifespan increased by at least 12%.

[0166] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in 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 having a structure shown in Formula I: in, Ring A is a naphthalene ring; X is selected from C(R'R"), N(R), O or S; Ar1 and Ar 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 20 carbon atoms; 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in Ar1, Ar, L, L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms; R', R", and R are the same or different and are each independently selected from 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, or an aryl group having 6 to 20 carbon atoms; or R' and R", together with the carbon atom to which they are attached, form a saturated or unsaturated 5-13 membered ring; R1, R2, R3 and R4 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 trialkylsilyl group having 3 to 12 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; n1 is the number of R1, n1 is selected from 0, 1, 2, 3, 4 or 5, when n1 is greater than 1, any two R1 are the same or different; n2 is the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different; n3 is the number of R3, n3 is selected from 0, 1, 2, 3 or 4, when n3 is greater than 1, any two R3 are the same or different; n4 is the number of R4, and n4 is selected from 0, 1, 2 or 3. When n4 is greater than 1, any two R4 are the same or different.

2. The organic compound according to claim 1, wherein R', R" and R are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, trideuteromethyl, trifluoromethyl, phenyl, naphthyl or biphenyl; or R' and R" together with the carbon atom to which they are attached form a cyclopentane, cyclohexane or fluorene ring.

3. The organic compound according to claim 1, wherein R1, R2, R3 and R4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

4. The organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

5. The organic compound according to claim 1, wherein Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

6. 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 3 to 18 carbon atoms; Optionally, 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.

7. 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 dibenzothiophenylene group, or a substituted or unsubstituted carbazolylene group; Alternatively, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

8. The organic compound according to claim 1, wherein L, 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:

9. The organic compound according to claim 1, wherein Ar1 is 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; Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

10. The organic compound according to claim 1, wherein Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

11. The organic compound according to claim 1, wherein Ar1 is selected from the group consisting of:

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

13. 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; wherein: The functional layer includes the organic compound according to any one of claims 1 to 12.

14. The electronic component according to claim 13, 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.

15. An electronic device comprising the electronic component according to claim 13 or 14.

Images