Organic compounds and electronic components and electronic devices

Abstract

This application belongs to the technical field of organic materials, and provides an organic compound, an electronic component, and an electronic device. The structure of the organic compound is shown in Formula 1, and only one of R1 to R 10 is a group A shown in Formula 2. The organic compound can improve the performance of the electronic component. #imgabs0#

Description

Technical Field

[0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to 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 having a structure shown in Formula 1:

[0007]

[0008] In formula 1, R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are the same or different and are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated 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 or a group A, and R 1 To R 10 There is only one group A in the group, and the structure of the group A is shown in Formula 2:

[0009]

[0010] Among them, X 1 , X 2 and X 3 are the same or different and are each independently selected from N or C(H), and X 1 , X 2 and X 3 At least one of is N;

[0011] Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0012] L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0013] Ar 1 ,Ar 2 ,L,L 1 and L 2 The substituents in are the same as or different from each other and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated 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, and a trialkylsilyl group having 3 to 12 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring of 3 to 15 members.

[0014] In a second aspect, 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.

[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] Among the compounds of the present application, benz[de]anthracene The structure formed by the 7-position spiro-adamantane is the parent nucleus, which is a condensed ring structure of a large conjugated plane. After combining it with an electron-deficient heteroaryl group, the compound of the present application formed has a high electron mobility, which can effectively promote the transmission and injection of electrons, thereby improving the luminous efficiency of the device; in addition, the structure has good thermal stability and ensures that the material has good non-crystallization, thereby ensuring the uniformity of the film formation of the material during evaporation film formation, thereby improving the life of the device. Therefore, the compound of the present application is applied to an organic electroluminescent device as an electron transport layer material, which can effectively improve the service life and luminous efficiency of the device.

[0017] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. 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] Description of Reference Numerals

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

[0026] 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.

[0027] The first aspect of the present application provides an organic compound, the structure of which is shown in Formula 1:

[0028]

[0029] In formula 1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are the same or different and are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated 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 or a group A, and R 1 To R 10 There is only one group A in the group, and the structure of the group A is shown in Formula 2:

[0030]

[0031] Among them, X 1 , X 2 and X 3 are the same or different and are each independently selected from N or C(H), and X 1 , X 2 and X 3 At least one of is N;

[0032] Ar 1 and Ar 2are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0033] L, L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0034] Ar 1 ,Ar 2 ,L,L 1 and L 2 The substituents in are the same as or different from each other and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a deuterated 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, and a trialkylsilyl group having 3 to 12 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring of 3 to 15 members.

[0035] 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.

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

[0037] 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 non-substituted aryl having a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a cycloalkyl group, a trialkylsilyl group, a deuterated aryl 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.

[0038] 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.

[0039] 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.

[0040]

[0041] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by 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.

[0042] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium, 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.

[0043] 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.

[0044] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as deuterium, 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.

[0045] 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):

[0046]

[0047] 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):

[0048]

[0049] 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):

[0050]

[0051] In the present application, the halogen group includes bromine, fluorine, chlorine, iodine, etc., preferably fluorine.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] In the present application, the carbon number of the haloalkyl group as a substituent may be 1 to 10, preferably 1 to 4. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0059] Optionally, the structure of the organic compound is as shown in Formula 1A or Formula 1B:

[0060]

[0061] In some embodiments, the structure of the organic compound is selected from the group consisting of Formula 1-1 to Formula 1-5:

[0062]

[0063] In this application, X 1 , X 2 and X 3 All are N, or X 1 , X 2 and X 3 Two of them are N, and the remaining one is C(H), or X 1 , X 2 and X 3 One of them is N, and the remaining two are C(H).

[0064] Optionally, R 1 To R 10One of them is group A, and the others are each independently selected from hydrogen, deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, deuterated alkyl having 1-4 carbon atoms, trialkylsilyl having 3-7 carbon atoms, aryl having 6-12 carbon atoms, deuterated aryl having 6-12 carbon atoms, heteroaryl having 5-12 carbon atoms, and cycloalkyl having 5-10 carbon atoms.

[0065] Further optionally, R 1 To R 10 One of them is group A, and the others are each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl.

[0066] 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 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30 carbon atoms.

[0067] 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 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.

[0068] Further 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.

[0069] 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolylene group.

[0070] Optionally, L, L 1 and L 2The substituents in are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, halogenated alkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, and deuterated aryl having 6 to 12 carbon atoms.

[0071] Further optionally, L, L 1 and L 2 The substituents in are each independently selected from deuterium, fluorine, cyano, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl.

[0072] In one embodiment, L, L 1 , L 2 are each independently selected from the group consisting of a single bond and the following groups:

[0073]

[0074] Further optionally, L, L 1 and L 2 Each is independently selected from the group consisting of a single bond or the following groups:

[0075]

[0076] In this application, 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 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 carbon atoms.

[0077] In one embodiment, 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 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.

[0078] Optionally, Ar 1 and Ar 2Each 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 fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0079] Optionally, Ar 1 and Ar 2 The substituents in are each independently selected from deuterium, fluorine, cyano, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, deuterated alkyl having 1-4 carbon atoms, aryl having 6-12 carbon atoms, heteroaryl having 5-12 carbon atoms, cycloalkyl having 5-10 carbon atoms, trialkylsilyl having 3-7 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring of 5-15 members.

[0080] Further optionally, Ar 1 and Ar 2 The substituents in are each independently selected from deuterium, fluorine, cyano, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or trimethylsilyl; optionally, any two adjacent substituents form a benzene ring, cyclopentane, cyclohexane or fluorene ring.

[0081] In one embodiment, Ar 1 and Ar 2 Each is independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0082]

[0083] The substituents in the substituted group W are each independently selected from deuterium, fluorine, cyano, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl. When the number of substituents is greater than 1, the substituents are the same or different.

[0084] Optionally, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0085]

[0086]

[0087] Further optionally, Ar 1 and Ar 2 Each is independently selected from the group consisting of:

[0088]

[0089] In some embodiments, The same or different, and each independently selected from the group consisting of the following groups:

[0090]

[0091]

[0092] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] 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 application 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.

[0102] 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.

[0103] Optionally, the functional layer includes an electron transport layer, and the electron transport layer includes the organic compound of the present application.

[0104] In the present application, the electronic component may be an organic electroluminescent device or a photoelectric conversion device.

[0105] 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.

[0106] Optionally, the electron transport layer 340 includes the organic compound of the present application.

[0107] Optionally, the hole transport layer 320 includes a first hole transport layer 321 (C-HT) and a second hole transport layer 322 (Prime, also called "luminescence auxiliary layer" or "electron blocking layer") which are stacked, and relative to the second hole transport layer 322, the first hole transport layer 321 is closer to the anode.

[0108] 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.

[0109] Optionally, the materials of the first hole transport layer 321 and the second hole transport layer 322 can be selected from various existing hole transport layer materials, and the present application has no particular limitation on this. The hole transport layer material 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, and specific examples include but are not limited to at least one of the following compounds:

[0110]

[0111] In a specific embodiment, the material of the first hole transport layer 321 is HT-3, and the material of the second hole transport layer 322 is TCAC.

[0112] 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.

[0113] 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:

[0114]

[0115] In a specific embodiment, the host material is BH-1.

[0116] 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:

[0117]

[0118] In a specific embodiment, the guest material is BD-1.

[0119] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include the organic compound of the present application and one or more other electron transport materials. The other electron transport materials may generally include metal complexes and / or nitrogen-containing heterocyclic derivatives, wherein the metal complex material may be selected from 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.

[0120] In a specific embodiment, the electron transport layer 340 is composed of LiQ and the organic compound of the present application.

[0121] 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.

[0122] Alternatively, if Figure 1 As 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:

[0123]

[0124] In a specific embodiment, the hole injection layer 310 is composed of HAT-CN.

[0125] 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.

[0126] 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.

[0127] 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 electron transport layer 340 includes the organic compound of the present application.

[0128] Optionally, the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.

[0129] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0130] According to one embodiment, Figure 2As 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.

[0131] According to another embodiment, Figure 4 As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 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.

[0132] 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.

[0133] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0134] 1. Synthesis of intermediate IMAX

[0135] Take IMA1 as an example to illustrate the synthesis of IMAX.

[0136]

[0137] (1) Under nitrogen protection, 1,8-dibromonaphthalene (60.0 g, 0.210 mol), 4-chlorophenylboric acid (32.7 g, 0.210 mol), toluene (600 mL), ethanol (240 mL), water (240 mL), potassium carbonate (55.5 g, 0.404 mol) were added to the reaction bottle. After the addition, the mixture was stirred and heated to 50-60°C. Then, tetrakis(triphenylphosphine)palladium (2.3 g, 2.01 mmol) was quickly added. After the addition, the mixture was refluxed at 70-75°C for 16 h. After the reaction was completed, the mixture was cooled and extracted with toluene. The organic phase was washed with water until neutral, dried, filtered, and concentrated to obtain a crude product. The crude product was recrystallized with a mixed solvent of dichloromethane and petroleum ether and dried to obtain IMA1-1 (39.6 g, yield 62.1%) as a white solid.

[0138]

[0139] (2) IMA1-1 (39.6 g, 0.125 mol) and dry tetrahydrofuran (396 mL) were added to a 1 L three-necked flask, mechanical stirring was started, and the temperature was cooled to below -80°C with liquid nitrogen. Under nitrogen protection, 75 mL (0.15 mol) of a 2 mol / L tetrahydrofuran solution of n-butyl lithium was slowly added dropwise. After the addition was completed, the temperature was kept at -90 to -80°C for 60 min. Then, a mixed solution of adamantane ketone (18.7 g, 0.125 mol) and tetrahydrofuran (187 mL) was added dropwise to the reaction system at -90 to -80°C. After the addition was completed, the temperature was kept at -90 to -80°C for 60 min. After the temperature rose to room temperature naturally, stirring was continued for 2 hours. 1 mol / L dilute hydrochloric acid was added dropwise to quench the reaction. The reaction solution was extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was recrystallized from ethanol to obtain IMA1-2 (33.2 g, yield 68.3%).

[0140]

[0141] (3) IMA1-2 (33.2 g, 0.085 mol) and glacial acetic acid (332 mL) were added to a 500 mL three-necked flask, and 3.32 g of concentrated sulfuric acid was slowly added dropwise under mechanical stirring. After the addition, the temperature was raised to 80°C and the reaction was continued for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, 332 mL of water was added to the reaction solution to precipitate solids, which were filtered and the obtained solid crude product was recrystallized from toluene to obtain IMA1-3 (21.9 g, yield 69.5%).

[0142]

[0143] (4) IMA1-3 (21.9 g, 0.059 mol) and 1,4-dioxane (220 mL) were added to a 500 mL three-necked reaction bottle, nitrogen was passed through, and then diboric acid pinacol ester (15.0 g, 0.059 mol) and potassium acetate (11.5 g, 0.118 mol) were added in sequence. The temperature was raised to 80°C to 90°C under mechanical stirring, and Pd was quickly added. 2 (dba) 3 (0.53 g, 0.58 mmol) and x-phos (0.55 g, 1.16 mmol), maintained at 80°C ~ 90°C for 15 hours. After the reaction, the temperature was lowered to room temperature. The reaction solution was extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was recrystallized from toluene to obtain IMA1 (20.9 g, yield 76.6%).

[0144] The other IMAXs were synthesized by referring to the synthesis method of IMA1, except that the raw material 1 was used to replace the 1,8-dibromonaphthalene in step (1), and the raw material 2 was used to replace the 4-chlorophenylboronic acid in step (1). The yields of the synthesized intermediates and the final step are shown in Table 1.

[0145] Table 1

[0146]

[0147]

[0148] 2. Synthesis of intermediate IM B1-2

[0149]

[0150] (1) 1-Bromo-8-phenylnaphthalene (34.0 g, 0.120 mol) and dry tetrahydrofuran (340 mL) were added to a 1 L three-necked flask, mechanical stirring was started, and the temperature was cooled to below -80°C with liquid nitrogen. Under nitrogen protection, 65 mL (0.130 mol) of a 2 mol / L tetrahydrofuran solution of n-butyl lithium was slowly added dropwise. After the addition was completed, the temperature was kept at -90 to -80°C for 60 min, and then heated at -90 to -80°C. A mixed solution of adamantane ketone (19.8 g, 0.132 mol) and tetrahydrofuran (190 mL) was added dropwise to the reaction system. After the addition was completed, the mixture was kept warm for 60 min. After naturally warming to room temperature, stirring was continued for 2 hours. 1 mol / L dilute acid water was added dropwise to quench the reaction. The reaction solution was extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was recrystallized from ethanol to obtain IMB1-1 (29.9 g, yield 70.3%).

[0151] (2) IM B1-1 (29.4 g, 0.083 mol) and glacial acetic acid (300 mL) were added to a 500 mL three-necked flask, and 3.0 g of concentrated sulfuric acid was slowly added dropwise under mechanical stirring. After the addition, the temperature was raised to 80°C and the reaction was carried out for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and 300 mL of deionized water was added to the reaction solution to precipitate solids. The solids were filtered and the obtained crude solids were recrystallized with dichloromethane and n-hexane to obtain IM B1-2 (20.7 g, yield 74.2%).

[0152] 3. Synthesis of intermediates IM BX-a and IM BX-b

[0153] The synthesis of IM BX-a and IM BX-b is illustrated by taking IM B1-a and IM B1-b as examples.

[0154]

[0155] Under nitrogen protection, IM B1-2 (41.0 g, 121.8 mmol) and 320 mL of dichloromethane were added to the reaction flask. Cooled to 0 ° C, N-bromosuccinimide (47.7 g, 268.0 mmol) was added in batches. The reaction was protected from light for 24 hours, 300 mL of dichloromethane was added and extracted with water. The organic phase was collected, dried over anhydrous sodium sulfate, and the organic solvent was removed under reduced pressure. Column chromatography was performed with dichloromethane and petroleum ether (v / v=1:5) as eluents to obtain white powders IM B1-a (21.3 g, yield 42.0%) and IM B1-b (14.1 g, yield 27.8%).

[0156] The same method as IM B1-a and IM B1-b was used to prepare other IM BX-a and IM BX-b, except that raw material 3 was used instead of IM B1-2. Other conditions remained unchanged. The obtained products and yields are shown in Table 2.

[0157] Table 2

[0158]

[0159] 4. Synthesis of intermediate IM CX

[0160] Take IM C1 as an example to illustrate the synthesis of IM CX:

[0161]

[0162] (1) Under nitrogen protection, IM B2-a (10.0 g, 22.27 mmol), phenylboric acid (2.8 g, 23.03 mmol), toluene (100 mL), ethanol (40 mL), water (20 mL), potassium carbonate (6.8 g, 49.01 mmol) were added to the reaction bottle. After the addition, the mixture was stirred and heated to 50°C to 60°C. Then, tetrakis(triphenylphosphine)palladium (0.5 g, 0.44 mmol) and tetrabutylammonium bromide (1.4 g, 4.45 mmol) were quickly added. After the addition, the mixture was refluxed at 70 to 75°C for 12 h. After the reaction was completed, the temperature was lowered, and the mixture was extracted with toluene. The organic phase was washed with water until neutral, dried, filtered, and concentrated. The crude product was recrystallized and purified using dichloromethane / n-hexane, and dried to obtain IM C1-1 (7.9 g, yield 79.4%) as a white solid.

[0163] (2) IM C1-1 (7.6 g, 17.00 mmol) and 1,4-dioxane (80 mL) were added to a 250 mL three-necked reaction bottle, nitrogen was passed through, and then diboric acid pinacol ester (4.5 g, 17.85 mmol) and potassium acetate (3.34 g, 34.00 mmol) were added in sequence. The temperature was raised to 80°C to 90°C under mechanical stirring, and Pd was quickly added. 2(dba) 3 (0.17 g, 0.19 mmol) and x-phos (0.18 g, 0.37 mmol), maintained at 80°C-90°C for 15 h. After the reaction, the temperature was lowered to room temperature. The reaction solution was extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was recrystallized from dichloromethane / n-hexane to obtain IM C1 (6.5 g, yield 71.2%).

[0164] IM CX-1 was first synthesized by referring to the method of IM C1-1, except that raw material 4 was used instead of IM B2-a, and raw material 5 was used instead of phenylboronic acid; then IM CX was synthesized by referring to the method of IM C1, except that IM CX-1 was used instead of IM C1-1, and other conditions remained unchanged. The synthesized intermediates and their yields are shown in Table 3.

[0165] Table 3

[0166]

[0167]

[0168] 5. Synthesis of intermediate IM DX

[0169] The synthesis of each IM DX is explained using IM D1 as an example.

[0170]

[0171] Under nitrogen protection, IMA2-3 (6.0 g, 0.016 mol), 1,3-diphenyldiboronic acid pinacol ester (5.6 g, 0.017 mol), toluene (60 mL), ethanol (25 mL), water (15 mL), potassium carbonate (4.9 g, 0.035 mol) were added to the reaction bottle. After the addition, the mixture was stirred and heated to 50-60°C. Then, tetrakis(triphenylphosphine)palladium (0.37 g, 0.32 mmol) and tetrabutylammonium bromide (1.04 g, 3.24 mmol) were quickly added. After the addition, the mixture was refluxed at 70-75°C for 16 h. After the reaction was completed, the temperature was lowered, the mixture was extracted with toluene, the organic phase was washed with water until neutral, dried, filtered, concentrated, and the obtained crude product was recrystallized from a mixed solvent of ethyl acetate and petroleum ether, and dried to obtain IM D1 (4.3 g, 49.4%) as a white solid.

[0172] The IM DX listed in Table 4 were synthesized by referring to the method of IM D1, except that raw material 6 was used instead of IMA2-3, and raw material 7 was used instead of 1,3-bisphenyldiboronic acid pinacol ester. The synthesized intermediates and their yields are shown in Table 4.

[0173] Table 4

[0174]

[0175]

[0176] 6. Synthesis of intermediates IM D6 and IM D7

[0177]

[0178] IM B1-a (9.0 g, 22.39 mmol) and 1,4-dioxane (90 mL) were added to a 250 mL three-necked reaction bottle, nitrogen was passed through, and then diboric acid pinacol ester (5.9 g, 23.28 mmol) and potassium acetate (4.4 g, 44.79 mmol) were added in sequence. The temperature was raised to 80-90 °C under mechanical stirring, and Pd was quickly added. 2 (dba) 3 (0.29 g, 0.31 mmol) and x-phos (0.3 g, 0.63 mmol), maintained at 80-90 ° C for 12 hours. After the reaction, the temperature was lowered to room temperature. The reaction solution was extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was recrystallized from dichloromethane / n-hexane to obtain IM D6 (7.7 g, yield 74.4%).

[0179]

[0180] IM D7 was synthesized by referring to the method of IM D6, except that IM B1-b was used instead of IM B1-a to obtain IM D7 (5.9 g, yield 72.6%).

[0181] Synthesis example 1

[0182] Synthesis of compound P1:

[0183]

[0184] Under nitrogen protection, IMA1 (6.6 g, 0.014 mol), raw material Sub 1 (6.0 g, 0.014 mol), toluene (60 mL), ethanol (30 mL), water (15 mL), sodium carbonate (4.34 g, 0.031 mol) were added to the reaction bottle. After the addition, the mixture was stirred and heated to 50°C to 60°C. Then, tetrakis(triphenylphosphine)palladium (0.33 g, 0.29 mmol) and tetrabutylammonium bromide (TBAB, 0.92 g, 0.0029 mol) were added. After the addition, the mixture was reacted at 70°C to 75°C for 5 h. After the reaction was completed, the mixture was cooled and extracted with toluene. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a crude product. The obtained crude product was recrystallized with a mixed solvent of dichloroethane and n-heptane and dried to obtain a white solid compound P1 (5.5 g, 53.5%), mass spectrum: m / z = 720.3 [M+H] + .

[0185] Synthesis example 2-39

[0186] The compounds of the present application listed in Table 5 were synthesized by referring to the synthesis method of compound P1, except that raw material 8 was used instead of IMA1, and raw material 9 was used instead of Sub 1. The synthesized compounds, their yields, and mass spectrometry characterization structures are shown in Table 5.

[0187] Table 5

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] The NMR data of some compounds are shown in Table 6:

[0195] Table 6

[0196]

[0197] Example of fabrication and evaluation of organic electroluminescent devices

[0198] Example 1

[0199] The anode was prepared by the following process: The ITO / Ag / ITO substrate (made by Corning) was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness) and prepared into an experimental substrate with cathode overlap area, anode and insulation layer pattern by photolithography process. 2 :N 2 Plasma surface treatment was performed to increase the work function of the anode (experimental substrate) and to remove scum.

[0200] HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a A hole injection layer (HIL) of 100 mm thick was formed by vacuum evaporating HT-3 on the hole injection layer. The first hole transport layer (HTL-1) is formed.

[0201] TCTA (4,4',4"-tri(carbazole-9-yl)triphenylamine) was evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer (HTL-2) is formed.

[0202] BH-1 was used as the main body and BD-1 was doped at the same time. The main body and the dopant were evaporated on the second hole transport layer at a film thickness ratio of 97:3 to form a film with a thickness of of an organic electroluminescent layer (EML).

[0203] Compound P1 and LiQ (8-hydroxyquinoline-lithium) were mixed in a weight ratio of 1:1 and evaporated on the organic light-emitting layer to form Thick electron transport layer (ETL).

[0204] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:4 and vacuum-deposited on the electron injection layer to form an electron injection layer with a thickness of cathode.

[0205] CP-1 is evaporated on the cathode to form a layer with a thickness of An organic cover layer (CPL) is formed to complete the manufacture of the organic electroluminescent device.

[0206] Example 2-39

[0207] Organic electroluminescent devices were prepared in the same manner as in Example 1, except that the compounds shown in Table 7 ("ETL" column) were used instead of Compound P1 when forming the electron transport layer (ETL).

[0208] Comparative Examples 1-3

[0209] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used instead of compound P1 when forming an electron transport layer (ETL).

[0210] In the above embodiments and comparative examples, the structures of the main compounds used are shown below.

[0211]

[0212] For the organic electroluminescent device prepared as above, at 10 mA / cm 2 The IVL performance of the device was analyzed under the conditions of T95% device life at a constant current density of 20 mA / cm 2 The device performance is shown in Table 7.

[0213] Table 7

[0214]

[0215]

[0216] According to the results of Table 7 above, the performance of the organic electroluminescent device prepared in Example 1-39 is improved compared with the organic electroluminescent device in Comparative Examples 1-3; specifically, compared with Comparative Examples 1-3, the luminous efficiency of the organic electroluminescent device in Example 1-39 is at least increased by 15.7%, and the T95 life of the device is at least increased by 13.7%. Therefore, the compound of the present application is used as an electron transport layer material of an organic electroluminescent device, while maintaining a lower operating voltage of the device, the luminous efficiency and service life of the device can be further improved.

[0217] The preferred embodiments of the present application are described in detail above; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula 1 below: In Formula 1, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 are the same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl or group A, and R1 to R 10 There is only one group A in the group, and the structure of the group A is shown in Formula 2: wherein X1, X2 and X3 are the same or different and are independently selected from N or C(H), and X1, X2 and X3 are all N, or two of X1, X2 and X3 are N and the remaining one is C(H); 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 terphenyl, 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 each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl or trimethylsilyl; optionally, any two adjacent substituents form a fluorene ring; 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, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl or naphthyl; Indicates a single bond.

2. 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 1-5:

3. The organic compound according to claim 1, wherein L, L1 and L2 are each independently selected from the group consisting of a single bond and the following groups:

4. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups: The substituents in the substituted group W are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl. When the number of substituents is greater than 1, the substituents are the same or different.

5. The organic compound according to claim 4, wherein Ar1 and Ar2 are each independently 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 contains 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 an electron transport layer, and the electron transport layer includes the organic compound.

9. The electronic component according to claim 7, 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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