Organic compounds and electronic components and electronic devices

Abstract

The present application belongs to the field of organic light-emitting materials, and specifically relates to an organic compound, an electronic component and an electronic device. The structure of the organic compound is shown in Formula 1, and the organic compound can improve the performance of the electronic component.

Description

Technical Field

[0001] The present application relates to the field of organic light-emitting materials, and specifically provides an organic compound, an electronic component, and an electronic device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials emit light under the action of an electric field and are stimulated by electric current. It is a process of converting electrical energy into light energy. Compared with inorganic light-emitting materials, organic light-emitting diodes (OLEDs) have the advantages of active light emission, large optical range, low driving voltage, high brightness, high efficiency, low energy consumption, and simple manufacturing process. It is precisely because of these advantages that organic light-emitting materials and devices have become one of the most popular research topics in the scientific and industrial communities.

[0003] Organic electroluminescent devices generally include 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 to 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 to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0004] Currently, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size application fields such as TVs. However, compared with the actual product application requirements, the luminous efficiency and service life of OLED devices need to be further improved. Research on improving the performance of OLED light-emitting devices includes: reducing the operating voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously research and innovate OLED optoelectronic functional materials to create functional materials with higher performance OLEDs. Summary of the invention

[0005] In view of the above problems existing in the prior art, the purpose of the present application is to provide an organic compound, an electronic component and an electronic device. The organic compound of the present application can effectively improve the performance of the electronic component.

[0006] In a first aspect, the present application provides an organic compound, the structure of which is shown in Formula 1:

[0007]

[0008] wherein X is selected from O or S;

[0009] Ring A is a 5- to 10-membered saturated aliphatic 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 5 to 30 carbon atoms;

[0011] Ar, 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 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms;

[0012] L, L 1 , L 2 ,Ar,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 haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkylthio group having 1 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring of 3 to 15 members;

[0013] R 1 and R 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms; n 1 Represents R 1 The number of and is selected from 0, 1 or 2, when n 1 When R 1 Same or different; n 2 Represents R 2 The number of and is selected from 0, 1, 2, 3 or 4, when n 2 When R is greater than 1, 2 Same or different.

[0014] In a second aspect, the present invention provides an electronic component, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0015] In a third aspect, the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0016] The compound of the present application is a triarylamine derivative, and an oxathiazole structure is fused on a cycloalkyl spirofluorene as the core group of the triarylamine. The electron-withdrawing effect of the heteroatoms on the oxathiazole can appropriately reduce the electron cloud density on the plane of the group, thereby reducing the injection barrier of holes into the light-emitting layer. Therefore, when used in an OLED device, the luminous efficiency of the device can be effectively improved; in addition, the non-conjugated characteristics of the cycloalkyl on the spirofluorene can be used to improve the thermal stability of the entire molecule, improve the film-forming property of the material, and effectively inhibit the crystallization of the molecule after film formation, which is beneficial to improving the life of the device. Therefore, the compound of the present application is applied to an OLED device as a second hole transport layer material, which can effectively improve the luminous efficiency and service life of the device.

[0017] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] 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.

[0019] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0020] Figure 2 It is a schematic structural diagram of a first electronic device according to an embodiment of the present application.

[0021] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0022] Figure 4 It is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

[0023] Description of Reference Numerals

[0024] 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

[0025] The specific implementation of the present invention is described in detail below in conjunction with the accompanying drawings. It should be understood that the specific implementation described here is only used to illustrate and explain the present invention, and is not used to limit the present invention.

[0026] In a first aspect, the present application provides an organic compound, the structure of which is shown in Formula 1:

[0027]

[0028] wherein X is selected from O or S;

[0029] Ring A is a 5- to 10-membered saturated aliphatic ring;

[0030] 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 5 to 30 carbon atoms;

[0031] Ar, 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 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 40 carbon atoms;

[0032] L, L 1 , L 2 ,Ar,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 haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an alkylthio group having 1 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring of 3 to 15 members;

[0033] R 1 and R 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms; n 1 Represents R 1 The number of and is selected from 0, 1 or 2, when n 1 When R 1 Same or different; n 2 Represents R 2 The number of and is selected from 0, 1, 2, 3 or 4, when n 2 When R is greater than 1, 2 Same or different.

[0034] In this application, the descriptions "each... is independently selected from" and "... are 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 selected from 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, each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.

[0035] In the present application, the terms "optionally" and "optionally" mean that the event or environment described later may but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents may form a ring but do not have to form a ring, which includes: the situation where two adjacent substituents form a ring and the situation where two adjacent substituents do not form a ring.

[0036] 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 substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a cycloalkyl group, a trialkylsilyl group, an alkylthio group, an alkoxy group, etc. In the present application, the "substituted" functional group can be substituted by one or more of the above Rc; when two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or be connected to each other to form a spiro ring together with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc can exist independently or be fused to form a ring with the functional group to which they are connected.

[0037] The "ring" in this application includes saturated rings and unsaturated rings; saturated rings are cycloalkyl and heterocycloalkyl, and unsaturated rings include cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl. In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl; fluorene ring belongs to a 13-membered ring, cyclohexane belongs to a 6-membered ring, and adamantane belongs to a 10-membered ring.

[0038] In the present application, when “any two adjacent substituents form a 3-15-membered saturated or unsaturated ring”, the formed ring is a saturated ring or an unsaturated ring, wherein a saturated ring is, for example, cyclopentane Cyclohexane Unsaturated rings are, for example, benzene, naphthalene or fluorene.

[0039] 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 carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. It should be noted that biphenyl and fluorenyl are both regarded as aryl in the present application. 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.

[0040] 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, fluorine, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl, alkoxy, alkylthio, trialkylsilyl, etc. Specific examples of heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophenyl substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms 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.

[0041] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring, and the heteroatoms may be at least one 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. For example, heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, as well as N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Among them, thienyl, furanyl, phenanthroline, etc. are heteroaryl groups of single aromatic ring system type, N-phenylcarbazolyl, N-pyridyl are heteroaryl groups of polycyclic system type connected by carbon-carbon bond conjugation. In this application, the heteroaryl group involved refers to a divalent group formed by further losing a hydrogen atom of the heteroaryl group.

[0042] 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, fluorine, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated alkyl, alkoxy, alkylthio, trialkylsilyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0043] 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):

[0044]

[0045]

[0046] 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):

[0047]

[0048] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connecting bond, and the meaning represented by it includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

[0049]

[0050] In the present application, the halogen group includes bromine, fluorine, chlorine, iodine, etc., preferably fluorine.

[0051] In the present application, the alkyl group with 1-10 carbon atoms includes a straight-chain alkyl group with 1-10 carbon atoms and a branched-chain alkyl group with 3-10 carbon atoms, and the carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group with 1-10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0052] In the present application, the carbon number of the aryl group as a substituent may be 6-18, for example, 6, 10, 12, 14, 18, etc. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, naphthyl, biphenyl.

[0053] In the present application, the carbon number of the heteroaryl group as a substituent can be 5-18, for example, the carbon number is 5, 8, 9, 10, 12, 18, etc. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, etc.

[0054] In the present application, the carbon number of the cycloalkyl group as a substituent may be 3-10, for example, 3, 5, 6, 8, 10, etc. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and the like.

[0055] In the present application, the trialkylsilyl group as a substituent may have 3-12 carbon atoms, for example, 3, 5, 6, 8, 10, etc. Specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl.

[0056] In the present application, the carbon number of the deuterated alkyl group as a substituent may be 1 to 10, preferably 1 to 4. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl group.

[0057] In the present application, the carbon number of the halogenated alkyl group as a substituent may be 1 to 10, preferably 1 to 4. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0058] Optionally, ring A is selected from cyclopentane, cyclohexane, norbornane, and adamantane.

[0059] Further optionally, ring A is selected from the group consisting of the following groups:

[0060]

[0061] According to the present application, in Formula 1, express and The structure formed by fusing any two adjacent positions of the positions a, b, c and d on the benzene ring of , where "*" represents the fusing site. For example, when and When adjacent positions a and b on the benzene ring are fused, The structure includes

[0062] In the present application, the structure of the organic compound is shown in Formula 11 or Formula 12:

[0063]

[0064] In formula 11, n 1 is 0, 1, or 2, n 2 is 0, 1, 2 or 3. In formula 12, n 1 is 0 or 1, n 2 Is 0, 1, 2, 3, or 4.

[0065] Optionally, R 1 and R 2 Each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0066] In a preferred embodiment, the structure of the organic compound is as shown in Formula 11, and Ring A is

[0067] Specifically, the structure of the organic compound is shown in any one of Formula A to Formula L:

[0068]

[0069]

[0070] In some embodiments, the structure of the organic compound is selected from the group consisting of Formula 1-1 to Formula 1-22:

[0071]

[0072]

[0073] In this application, L, L 1 , L 2 The same or different and can be 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, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30 carbon atoms.

[0074] Optionally, L, L 1 , 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 18 carbon atoms.

[0075] In some embodiments, L, L 1 , L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0076] Optionally, L, L 1 and L 2 The substituents in are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.

[0077] Optionally, L, L 1 and L 2The substituents in are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl or biphenyl.

[0078] In some embodiments, L, L 1 , L 2 Each is independently selected from a single bond, a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups:

[0079]

[0080] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl or naphthyl; when the number of substituents is greater than 1, each substituent is the same or different.

[0081] Optionally, L, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0082]

[0083] Further optionally, L, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0084]

[0085] In this application, Ar, Ar 1 and Ar 2 The same or different may be independently selected from: substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 carbon atoms; substituted or unsubstituted heteroaryl having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 carbon atoms.

[0086] In one embodiment, Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0087] In one embodiment, Ar 1and 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 20 carbon atoms.

[0088] Optionally, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

[0089] Optionally, Ar 1 and Ar 2 Each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0090] Optionally, Ar, Ar 1 and Ar 2 The substituents in are the same or different and are independently selected from deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, deuterated alkyl having 1-4 carbon atoms, fluoroalkyl having 1-4 carbon atoms, trialkylsilyl having 3-7 carbon atoms, aryl having 6-12 carbon atoms, heteroaryl having 5-12 carbon atoms or cycloalkyl having 5-10 carbon atoms, and optionally, any two adjacent substituents form a saturated or unsaturated ring of 5 to 13 members.

[0091] Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl or naphthyl.

[0092] Optionally, Ar 1 and Ar 2 The substituents in are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, any two adjacent substituents form a cyclopentane, cyclohexane or fluorene ring.

[0093] In a specific embodiment, Ar is selected from the group consisting of:

[0094]

[0095] Optionally, Ar is selected from the group consisting of:

[0096]

[0097] In some embodiments, Ar 1 and Ar 2 Each is independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following groups:

[0098]

[0099] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; when the number of substituents is greater than 1, the substituents are the same or different.

[0100] Optionally, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0101]

[0102] Further optionally, Ar 1 and Ar 2 Each independently selected from:

[0103]

[0104]

[0105] In some embodiments, The same or different, and each independently selected from the group consisting of the following groups:

[0106]

[0107] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] The present application does not particularly limit the synthesis method of the organic compound provided, and those skilled in the art can determine a suitable synthesis method based on the organic compound of the present application in combination with the preparation method provided in the synthesis example section. In other words, the synthesis example section of the present invention exemplarily provides a preparation method of an organic compound, and the raw materials used can be obtained by commercially available or by methods well known in the art. Those skilled in the art can obtain all the organic compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the organic compound will not be described in detail here, and those skilled in the art should not be construed as limiting the present application.

[0119] A second aspect of the present application provides an electronic component, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises the organic compound described in the first aspect of the present application.

[0120] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound of the present application.

[0121] In the present application, the electronic component may be an organic electroluminescent device or a photoelectric conversion device.

[0122] According to a specific embodiment, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device includes an anode 100, a hole transport layer 320, an organic light-emitting layer 330, an electron transport layer 340 and a cathode 200 which are stacked in sequence.

[0123] Optionally, the hole transport layer 320 includes the organic compound of the present application.

[0124] Optionally, the hole transport layer 320 includes a first hole transport layer 321 (C-HT) and a second hole transport layer 322 (Prime, also known as "light-emitting auxiliary layer" or "electron blocking layer") stacked, and the first hole transport layer 321 is closer to the anode than the second hole transport layer 322. The first hole transport layer 321 and / or the second hole transport layer 322 contain the organic compound of the present application.

[0125] In 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 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 conductive polymers 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 (indium tin oxide, indiumtin oxide) (ITO) as an anode is included.

[0126] Optionally, the second hole transport layer 322 includes the organic compound of the present application.

[0127] Optionally, the material of the first hole transport layer 321 can be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorene-linked triarylamine compounds or other types of compounds, which are not specifically limited in the present application. For example, the material of the first hole transport layer 321 is selected from at least one of the following compounds:

[0128]

[0129] In a specific embodiment, the material of the first hole transport layer 321 is HT-3.

[0130] The organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material (also called a "dopant"). 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.

[0131] The main material of the organic light-emitting layer 330 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative, an anthracene derivative or other types of materials, and the present application does not impose any special restrictions thereon. For example, the main material is selected from one or more of the following compounds:

[0132]

[0133] In a specific embodiment, the host material of the organic light emitting layer 330 is a combination of RH-N and RH-P.

[0134] The guest material of the organic light-emitting layer 330 may be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, a biarylamine derivative having a fused aromatic subunit, or other materials, and the present application does not impose any particular limitation thereto. For example, the guest material is selected from at least one of the following compounds:

[0135]

[0136] In a specific embodiment, the guest material of the organic light emitting layer 330 is Ir(flq) 2 (acac) composition.

[0137] 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 and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, LiQ, Alq 3 , Bepq 2 etc.; the nitrogen-containing heterocyclic derivative may 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 BCP, Bphen, NBphen, DBimiBphen, BimiBphen, or at least one of the following compounds:

[0138]

[0139] In a specific embodiment, the electron transport layer 340 is composed of ET-5 and LiQ.

[0140] In the present application, cathode 200 includes 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.

[0141] Alternatively, if Figure 1As shown, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 320 to enhance the ability of injecting holes into the hole transport layer 320. 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 hole injection layer 310 is selected from the group consisting of the following compounds:

[0142]

[0143] In a specific embodiment, the hole injection layer 310 is composed of PD.

[0144] 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 an alkali metal and an organic substance. For example, the electron injection layer 350 includes LiQ or Yb.

[0145] In the present application, the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a red light device.

[0146] 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, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 stacked in sequence. The hole transport layer 320 includes the organic compound of the present application.

[0147] Optionally, the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.

[0148] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0149] 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 is, 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.

[0150] According to another embodiment, Figure 4As 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 is, 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.

[0151] Hereinafter, the present application will be described in further detail by way of examples. However, the following examples are merely illustrative of the present application and are not intended to limit the present application.

[0152] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0153] 1. Synthesis of intermediate IM-AX

[0154] 1-1) Synthesis of IM-A1

[0155]

[0156] (1) Add the raw material Sub a1-1 (40.00 g, 145.93 mmol) and dry tetrahydrofuran (320 mL) to a three-necked flask, cool to -78°C, slowly add n-butyl lithium in n-hexane solution (2 mol / L, 80.0 mL) dropwise under nitrogen protection, keep warm for 1 h, then add trimethyl borate (16.68 g, 160.51 mmol), keep warm for 3 h, then raise the temperature to 10°C-15°C, add hydrochloric acid for acidolysis, evaporate the solvent under reduced pressure, add water, precipitate crystals, filter, and recrystallize the filter cake with ethyl acetate / petroleum ether to obtain intermediate IM-A1-1 (30.21 g, yield 86.6%).

[0157]

[0158] (2) Under nitrogen protection, IM-A1-1 (30.0 g, 125.28 mmol), Sub a1-2 (39.76 g, 125.28 mmol), potassium carbonate (38.09 g, 275.62 mmol), tetrabutylammonium bromide (8.08 g, 25.06 mmol), toluene (300 mL), ethanol (120 mL) and deionized water (80 mL) were added to a three-necked flask, stirred for 15 min, tetrakis(triphenylphosphine)palladium (2.90 g, 2.51 mmol) was added and the temperature was raised to 75°C-80°C and stirred for 8 h; the reaction solution was cooled to room temperature, toluene (200 mL) was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, the organic phase was passed through a silica gel column, and then the solvent was removed under reduced pressure; a yellow oil, i.e., IM-A1-2 (35.42 g, yield 73.5%), was obtained.

[0159]

[0160] (3) IM-A1-2 (35.0 g, 90.99 mmol) and dry tetrahydrofuran (350 mL) were added to a three-necked flask, and the mixture was cooled to -80°C while stirring. Under nitrogen protection, a solution of n-butyl lithium in n-hexane (2 mol / L, 50.1 mL) was slowly added dropwise. The mixture was kept warm for 30 min after the addition. Then, a mixed solution consisting of 2-adamantanone (15.04 g, 100.09 mmol) and 200 mL of tetrahydrofuran was added. The mixture was kept warm for 30 min. After the mixture naturally warmed to room temperature, the mixture was stirred for 2 h. Water was added dropwise to quench the reaction. The reaction solution was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and then distilled under reduced pressure. The resulting crude solid was recrystallized from a mixed solvent of dichloromethane and n-heptane (volume ratio 1:5) to obtain IM-A1-3 (30.95 g, yield 74.6%).

[0161]

[0162] (4) Under nitrogen protection, IM-A1-3 (30.00 g, 65.79 mmol) and glacial acetic acid (300 mL) were added to a three-necked flask, and 30 mL of concentrated sulfuric acid (concentration 98 wt%) was slowly added dropwise under stirring. Then, the heating was turned on and the temperature was raised to 80°C for reaction for 8 h. Water was added to the reaction solution and extracted with ethyl acetate. The organic phase was separated and dried over magnesium sulfate and then distilled under reduced pressure. The crude product was recrystallized with a mixed solvent of ethyl acetate and n-hexane (volume ratio 1:3) to obtain the intermediate IM-A1 (21.98 g, yield 76.3%).

[0163] 1-2) The remaining intermediates IM-AX shown in Table 1 were synthesized by referring to the method of IM-A1, except that raw material 1 was used instead of Sub a1-1, raw material 2 was used instead of raw material Sub a1-2, and raw material 3 was used instead of 2-adamantanone. The obtained IM-AX and the yield of the last step are shown in Table 1.

[0164] Table 1

[0165]

[0166]

[0167] 2. Synthesis of intermediates IM a17-1 and IM a18-1

[0168] IM a17-1 and IM a18-1 were prepared by referring to the synthesis method of IM-A1-2 (step (2) in the synthesis process of IM-A1), except that raw material 4 was used instead of IM-A1-1, and raw material 5 was used instead of Sub a1-2. The synthesized intermediates and their yields are shown in Table 2.

[0169] Table 2

[0170]

[0171] 3. Synthesis of intermediates IM A17-1 and IM A18-1

[0172]

[0173] IM a17-1 (12.71 g, 45.43 mmol), pinacol diboron (12.70 g, 25.0 mmol), tris(dibenzylideneacetone)dipalladium (0.82 g, 0.90 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (0.21 g, 0.50 mmol), potassium acetate (8.82 g, 90.51 mmol) and 1,4-dioxane (130 mL) were added to the reaction bottle, the temperature was raised to 110 ° C under nitrogen protection, and the mixture was heated to reflux with stirring for 6 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate and filtered. After filtration, the filtrate was passed through a short silica gel column, and the solvent was removed under reduced pressure. The crude product was recrystallized and purified using dichloromethane / petroleum ether (volume ratio of 1:3) to obtain IM-A17-1 (10.76 g, yield 63.8%).

[0174] IM-A18-1 was synthesized by referring to the synthesis method of IM-A17-1, except that raw material 6 was used instead of IM a17-1. The synthesized intermediates and their yields are shown in Table 3.

[0175] Table 3

[0176]

[0177] 4. Synthesis of intermediates IM a19-0 to IM a22-0

[0178]

[0179] Under nitrogen protection, 4-bromo-3-chloro-2-fluoroaniline (20.00 g, 89.10 mmol), 1,3-dimethylimidazolidinone (120 mL) and benzoyl chloride (15.02 g, 106.92 mmol) were added to a three-necked flask, and the temperature was raised to 130°C and stirred at this temperature for 3 hours. After cooling to room temperature, water was added, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography to obtain intermediate IM a19-0 (25.53 g, yield 87.2%).

[0180] IM a20-0 to IM a22-0 were synthesized by referring to the synthesis method of IM a19-0, except that raw material 7 was used instead of 4-bromo-3-chloro-2-fluoroaniline. The synthesized intermediates and their yields are shown in Table 4.

[0181] Table 4

[0182]

[0183] 5. Synthesis of intermediates IM a19-1 to IM a22-1

[0184]

[0185] IM a19-0 (25.30 g, 77.00 mmol), dimethyl sulfoxide (150 mL), potassium carbonate (15.96 g, 115.50 mmol) and copper oxide (0.31 g, 3.86 mmol) were added to a three-necked flask in sequence and stirred at 110°C for 18 h. After cooling to room temperature, dichloromethane was added to dilute the mixture and filtered through Celite. The solvent was removed from the filtrate by vacuum distillation, and the resulting crystals were recrystallized using dichloromethane and methanol to obtain IM a19-1 (13.54 g, yield 57%).

[0186] IM a20-1 to IM a22-1 were synthesized by referring to the synthesis method of IM a19-1, except that raw material 8 was used to replace IMa19-0. The synthesized intermediates and their yields are shown in Table 5.

[0187] Table 5

[0188]

[0189] 6. Synthesis of intermediates IM-A19-1 to IM-A22-1

[0190] IM-A19-1 to IM-A22-1 were synthesized by referring to the synthesis method of IM-A1-1, except that Suba1-1 was replaced by raw material 9. The synthesized intermediates and their yields are shown in Table 6.

[0191] Table 6

[0192]

[0193]

[0194] 7. Synthesis of intermediates IM-A17 to IM-A21

[0195] IM-A17 to IM-A21 were synthesized by referring to the synthesis method of IM-A1 (steps (2) to (4)), except that raw material 10 was used instead of IM-A1-1, raw material 11 was used instead of Sub a1-2, and raw material 12 was used instead of 2-adamantanone. The obtained products and their final step yields are shown in Table 7.

[0196] Table 7

[0197]

[0198] 8. Synthesis of intermediates IM-A9-b, IM-A22-b and IM-A21-b

[0199] IM-A9-b, IM-A20-b and IM-A21-b were synthesized respectively by referring to the synthesis method of IM-A17-1, except that raw material 13 was used instead of IM a17-1. The synthesized intermediates and their yields are shown in Table 8.

[0200] Table 8

[0201]

[0202] 9. Synthesis of intermediates IM-A23 to IM-A25

[0203] IM-A23 to IM-A25 were prepared by referring to the synthesis method of IM-A1-2 (step (2) in the synthesis process of IM-A1), except that raw material 14 was used instead of IM-A1-1, and raw material 15 was used instead of Sub a1-2. The synthesized intermediates and their yields are shown in Table 9.

[0204] Table 9

[0205]

[0206] Synthesis Example 1: Synthesis of Compound 1

[0207]

[0208] (1) Under nitrogen protection, IM-A1 (14.0 g, 32.72 mmol), 4-aminobiphenyl (5.8 g, 34.34 mmol), tris(dibenzylideneacetone)dipalladium (0.30 g, 0.33 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.31 g, 0.65 mmol), sodium tert-butoxide (4.72 g, 49.07 mmol) and toluene (140 mL) were added to a three-necked flask in sequence, heated to 108°C, and stirred for 3 h; then cooled to room temperature, the reaction solution was washed with water until neutral, the organic phase was dried by adding magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using dichloromethane / n-heptane (volume ratio 1:3) to obtain a light yellow solid, the intermediate IM-A1-N1 (14.8 g, yield 79.3%).

[0209]

[0210] (2) Under nitrogen protection, IM-A1-N1 (7.5 g, 13.14 mmol), 3-bromodibenzofuran (3.25 g, 13.14 mmol), tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.11 g, 0.27 mmol), sodium tert-butoxide (1.89 g, 19.71 mmol) and toluene (80 mL) were added into a three-necked flask in sequence, heated to 108°C, stirred for 4 h, and then cooled to room temperature. The reaction solution was washed with water and dried with magnesium sulfate. After filtering, the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using toluene to obtain white solid compound 1 (4.8 g, yield 49.5%), mass spectrum: m / z=737.3 [M+H] + .

[0211] Synthesis Examples 2 to 30

[0212] The other compounds of the present application were synthesized by referring to the method of compound 7, except that raw material A was used instead of IM-A1, raw material B was used instead of 4-aminobiphenyl, and raw material C was used instead of 3-bromodibenzofuran. The obtained compounds and their yields (yields of the last step) and mass spectrometry characterization results are shown in Table 10.

[0213] Table 10

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] The NMR data of some compounds are shown in Table 11.

[0220] Table 11

[0221]

[0222] Example of fabrication and evaluation of organic electroluminescent devices

[0223] Example 1: Preparation of red organic electroluminescent device

[0224] Anodic pretreatment is performed by the following process: On the ITO / Ag / ITO substrate, the surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0225] PD was vacuum-deposited on the experimental substrate (anode) to form a Then, HT-3 was vacuum-deposited on the HIL to form a hole injection layer with a thickness of The first hole transport layer is formed by a plurality of holes.

[0226] Compound 7 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.

[0227] Next, RH-N:RH-P:Ir(flq) was added to the second hole transport layer. 2 (acac) was co-evaporated at an evaporation rate ratio of 49%:49%:2% to form a thickness of A red light emitting organic layer (EML) is provided.

[0228] On the organic light-emitting layer, the compound ET-5 and LiQ are mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0229] In addition, CP-1 is vacuum-evaporated on the cathode to form a layer with a thickness of An organic cover layer (CPL) is formed to complete the manufacture of a red organic electroluminescent device.

[0230] Embodiments 2 to 30

[0231] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the other compounds in Table 12 were used to replace Compound 7 in Example 1 when preparing the second hole transport layer.

[0232] Comparative Examples 1 to 4

[0233] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B, compound C and compound D were used to replace compound 7 in Example 1 when preparing the second hole transport layer.

[0234] The main material structures used in the above embodiments and comparative examples are as follows:

[0235]

[0236] The performance of the red organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 12.

[0237] Table 12

[0238]

[0239]

[0240] According to the results of Table 12 above, the performance of the organic electroluminescent device prepared in Example 1-30 is improved compared with the organic electroluminescent device in Comparative Examples 1-4; specifically, the luminous efficiency of the organic electroluminescent device in Example 1-30 is at least increased by 10.8%, and the T95 life of the device is at least increased by 11.1% compared with Comparative Examples 1-4. Therefore, the compound of the present application is used as the second hole transport layer of the organic electroluminescent device, which has the characteristics of further improving the luminous efficiency and service life of the device while maintaining a low operating voltage of the device.

[0241] The preferred embodiments of the present invention are described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. An organic compound, characterized in that The structure of the organic compound is shown in Formula 1: wherein X is selected from O or S; Ring A is selected from the group consisting of: L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; The substituents in L, L1 and L2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, and phenyl; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; The substituents in Ar are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, and phenyl; Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, phenyl; optionally, any two adjacent substituents form a fluorene ring; R1 and R2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, and phenyl; n1 represents the number of R1 and is selected from 0, 1 or 2. When n1 is 2, each R1 is the same or different; n2 represents the number of R2 and is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, each R2 is the same or different.

2. The organic compound according to claim 1, wherein The structure of the organic compound is shown in Formula 11 or Formula 12:

3. The organic compound according to claim 1, wherein The structure of the organic compound is selected from the group consisting of Formula 1-1 to Formula 1-22:

4. The organic compound according to claim 1, wherein L, L1, L2 are each independently selected from a single bond, a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups: The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, and phenyl; when the number of substituents is greater than 1, each substituent is the same or different.

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

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

7. An electronic component comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, characterized in that: The functional layer comprises the organic compound according to any one of claims 1 to 6.

8. The electronic component according to claim 7, wherein: The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

9. The electronic component according to claim 8, wherein: The electronic component is an organic electroluminescent device or a photoelectric conversion device.

10. An electronic device comprising the electronic component according to any one of claims 7 to 9.

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