Nitrogen-containing compound, electronic component and electronic device including the same

Abstract

This application relates to a nitrogen-containing compound, an electronic component and an electronic device comprising the same. The nitrogen-containing compound of this application has a structure shown in Formula 1. When the nitrogen-containing compound is applied to an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Technical Field

[0001] This application belongs to the technical field of organic materials, and particularly relates to a nitrogen-containing compound, an electronic component, and an electronic device comprising the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, electronic components for achieving electroluminescence or photoelectric conversion are increasingly widely used. Such electronic components generally include a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer as an energy conversion layer, an electron transport layer, and a cathode stacked in sequence. When a voltage is applied between the two electrodes, an electric field is generated. Under the action of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light externally.

[0003] The prior art has disclosed host materials for preparing organic light-emitting layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the Invention

[0004] Aiming at the above problems existing in the prior art, the purpose of this application is to provide a nitrogen-containing compound, an electronic component, and an electronic device comprising the same. The nitrogen-containing compound can improve the performance of the electronic component and the electronic device, such as enhancing the device efficiency and lifespan.

[0005] To achieve the above-mentioned invention purpose, this application adopts the following technical solutions:

[0006] According to the first aspect of this application, there is provided a nitrogen-containing compound having a structure as shown in Formula 1:

[0007]

[0008] Wherein, Ring A has a structure as shown in Formula 2;

[0009] Any two adjacent * positions in Formula 2 are fused with the # position in Formula 1; ;

[0010] L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12-30 carbon atoms;

[0011] Ar1 and Ar2 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 40 carbon atoms;

[0012] The substituents in L1, L2, Ar1 and Ar2 are the same or different, and are each independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups having 12 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, halogenated aryl groups having 6 to 20 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, halogenated alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, heterocycloalkyl groups having 2 to 10 carbon atoms or alkoxy groups having 1 to 10 carbon atoms;

[0013] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring;

[0014] R1 and R2 are the same or different, and are each independently selected from deuterium, halogen groups, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 12 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms or halogenated aryl groups having 6 to 20 carbon atoms;

[0015] n1 represents the number of R1, and is selected from 0, 1, 2 or 3; when n1 is greater than 1, any two R1 are the same or different;

[0016] n2 represents the number of R2, and is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n2 is greater than 1, any two R2 are the same or different.

[0017] According to the second aspect of the present application, there is provided an electronic component, including an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above nitrogen-containing compound.

[0018] According to the third aspect of the present application, there is provided an electronic device, including the electronic component described in the second aspect.

[0019] The nitrogen-containing compound of the present application has a tetramethylcyclohexane-fused 3,3-bicarbazole group as the core structure. Without affecting the molecular aromatic conjugation degree, this structure can reduce the intermolecular force and crystallinity, thereby improving the stability of the amorphous state of the material and the film-forming property; when the nitrogen-containing compound of the present application is used as the host material of the organic light-emitting layer in an organic electroluminescent device, it can improve the carrier balance in the organic light-emitting layer, broaden the carrier recombination region, improve the exciton generation and utilization efficiency, and improve the light-emitting efficiency and lifespan of the device.

[0020] Other features and advantages of the present application will be described in detail in the following detailed description section. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] The drawings are used to provide a further understanding of the present application, and constitute a part of the specification. Together with the following detailed description, they are used to explain the present application, but do not constitute a limitation to the present application.

[0022] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present application.

[0023] Figure 2 It is a schematic structural diagram of an electronic device of the present application.

[0024] REFERENCE NUMERALS

[0025] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer

[0026] 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer

[0027] 340, Hole blocking layer; 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device DETAILED DESCRIPTION

[0028] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of the present application.

[0029] In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by Formula 1:

[0030]

[0031] Among them, Ring A has a structure represented by Formula 2;

[0032] Any two adjacent * positions in Formula 2 are fused with the # position in Formula 1 ;

[0033] L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 30 carbon atoms;

[0034] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 40 carbon atoms;

[0035] The substituents in L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 12 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms;

[0036] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring;

[0037] R1 and R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 12 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms or a halogenated aryl group having 6 to 20 carbon atoms;

[0038] n1 represents the number of R1 and is selected from 0, 1, 2 or 3; when n1 is greater than 1, any two R1 are the same or different;

[0039] n2 represents the number of R2 and is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n2 is greater than 1, any two R2 are the same or different.

[0040] In the present application, the fluorenyl group may be substituted by one or two substituents. In the case where the above-mentioned fluorenyl group is substituted, it may be: etc., but not limited thereto.

[0041] In the present application, the description methods "each... is independently", "... are respectively independently" and "... are each independently selected from" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can also mean that within the same group, the specific options expressed between the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R” is independently selected from hydrogen, deuterium, fluorine, chlorine, which means that: formula Q-1 represents that there are q substituents R” on the benzene ring, and each R” can be the same or different, and the options of each R” do not affect each other; formula Q-2 represents that there are q substituents R” on each benzene ring of the biphenyl, and the number q of the R” substituents on the two benzene rings can be the same or different, and each R” can be the same or different, and the options of each R” do not affect each other.

[0042] In the present application, the term "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. Among them, the above-mentioned substituent, that is, Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a deuterated aryl group, a halogenated aryl group, a trialkylsilyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, etc.

[0043] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if L1 is a substituted arylene having 12 carbon atoms, then all the carbon atoms of the arylene and its substituents are 12.

[0044] In the present application, an aryl group refers to an optionally functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups conjugated through a carbon-carbon bond, a monocyclic aryl group and a fused polycyclic aryl group conjugated through a carbon-carbon bond, or two or more fused polycyclic aryl groups conjugated through a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond can also be regarded as the aryl group of the present application. Among them, the fused polycyclic aryl group can include, for example, a bicyclic fused aryl group (such as a naphthyl group), a tricyclic fused aryl group (such as a phenanthryl group, a fluorenyl group, an anthryl group), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group can include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a benzo[9,10]phenanthryl group, a pyrenyl group, a benzo[a]pyrenyl group, a spirobifluorene group, etc. In the present application, the arylene involved refers to a divalent group formed by further removing one hydrogen atom from the aryl group.

[0045] In the present application, the terphenyl group includes

[0046] In the present application, the substituted aryl may be one or more than two hydrogen atoms in the aryl being substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms of the substituted aryl refers to the total number of carbon atoms of the aryl and the substituents on the aryl. For example, a substituted aryl with 18 carbon atoms means that the total number of carbon atoms of the aryl and its substituents is 18.

[0047] In the present application, the heteroaryl refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, 6 or 7 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 through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without being limited thereto. Among them, thienyl, furyl, phenanthrolinyl, etc. are heteroaryls of the single aromatic ring system type, and N-phenylcarbazolyl, N-pyridylcarbazolyl are heteroaryls of the polycyclic system type conjugated through carbon-carbon bonds. In the present application, the sub-heteroaryl involved refers to a divalent group formed by the heteroaryl further losing one hydrogen atom.

[0048] In the present application, the substituted heteroaryl may be one or more than two hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0049] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl may be 6-40. For example, the number of carbon atoms may be 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.

[0050] In the present application, specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, and fluorenyl.

[0051] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be 12 - 40. For example, the number of carbon atoms can be 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.

[0052] In the present application, specific examples of the heteroaryl group as a substituent include, but are not limited to, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0053] In the present application, the non - localized 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 penetrated by the bond, and the other end is connected to the rest of the compound molecule.

[0054] In the present application, the alkyl group with 1 - 10 carbon atoms can include straight - chain alkyl groups with 1 to 10 carbon atoms and branched - chain alkyl groups with 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n - propyl, isopropyl, n - butyl, isobutyl, tert - butyl, n - pentyl, isopentyl, neopentyl, n - hexyl, n - octyl, 2 - ethylhexyl, nonyl, decyl, 3,7 - dimethyloctyl.

[0055] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, or iodine.

[0056] In the present application, the number of carbon atoms of the cycloalkyl group with 3 - 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl.

[0057] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non - localized connecting bonds penetrating the bicyclic ring, and its meaning includes any possible connection mode shown in formulas (f - 1) - (f - 10).

[0058]

[0059] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non - localized connecting bond extending from the middle of one of the benzene rings on one side, and its meaning includes any possible connection mode shown in formulas (X' - 1) - (X' - 4).

[0060]

[0061] In some embodiments of the present application, the nitrogen-containing compound has a structure represented by Formula 1-A, Formula 1-B or Formula 1-C:

[0062]

[0063] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0064] Optionally, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.

[0065] Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl groups having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, trideuteriomethyl, aryl groups having 6 to 12 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

[0066] In other embodiments of the present application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl.

[0067] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, trideuteriomethyl, phenyl, naphthyl or biphenyl.

[0068] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:

[0069]

[0070] Among them, the substituted group W has one or more than two substituents, and the substituents are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, trideuteriomethyl, phenyl, naphthyl or biphenyl, and when the number of substituents is greater than 1, the substituents are the same or different.

[0071] In some embodiments of the present application, Ar1 and Ar2 are independently selected from the group consisting of the following groups:

[0072]

[0073] Specifically, Ar1 and Ar2 are independently selected from the group consisting of the following groups:

[0074]

[0075] In some embodiments of the present application, L1 and L2 are the same or different, and are 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.

[0076] Optionally, the substituents in L1 and L2 are the same or different, and are independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 5 carbon atoms, or phenyl.

[0077] In some other embodiments of the present application, L1 and L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0078] Optionally, the substituents in L1 and L2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0079] In some embodiments of the present application, L1 and L2 are the same or different, and are independently selected from a single bond, a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of the following groups:

[0080]

[0081] Among them, represents a chemical bond; the substituted group V contains one or more substituents, and the substituents are selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents are the same or different.

[0082] Optionally, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0083]

[0084] Specifically, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0085]

[0086] In some embodiments of the present application, are each independently selected from the group consisting of the following groups:

[0087]

[0088]

[0089] Specifically, are each independently selected from the group consisting of the following groups:

[0090]

[0091] In some embodiments of the present application, R1 and R2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

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

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect, the present application provides an electronic component, which includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the nitrogen-containing compound of the present application.

[0104] In some embodiments of the present application, the electronic component is an organic electroluminescent device. As Figure 1 shown, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light-emitting layer 330, a hole blocking layer 340, an electron transport layer 350, and a cathode 200 that are sequentially stacked.

[0105] In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.

[0106] Optionally, the anode 100 includes the following anode materials, which are optionally materials with a large work function (work function) that contribute to 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, indium tin oxide (ITO) is included as the transparent electrode of the anode.

[0107] Optionally, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer is closer to the anode than the second hole transport layer.

[0108] In the present application, the hole transport layer 320 may include one or more hole transport materials, and the hole transport layer materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and specifically may be selected from the following compounds or any combination thereof:

[0109]

[0110] In one embodiment of the present application, the first hole transport layer 321 is composed of NPB.

[0111] In one embodiment of the present application, the second hole transport layer 322 is composed of TAPC.

[0112] Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not make special restrictions thereon. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof:

[0113]

[0114] In some embodiments of this application, the hole injection layer 310 is composed of HAT-CN.

[0115] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material or may include a host material and a dopant material. Optionally, the organic light-emitting layer 330 is composed of a host material and a dopant material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0116] The host material of the organic light-emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and this application does not make special restrictions thereon.

[0117] In some embodiments of this application, the host material of the organic light-emitting layer 330 is the nitrogen-containing compound of this application and GH-1.

[0118] The guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not make special restrictions thereon. The guest material is also called a dopant material or a dopant. According to the light-emitting type, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the green phosphorescent dopant include, but are not limited to,

[0119]

[0120] In some specific embodiments of this application, the guest material of the organic light-emitting layer 330 is Ir(ppy)2acac.

[0121] Optionally, the hole blocking layer 340 includes one or more hole blocking materials, and the hole blocking materials may be selected from carbazole polymers or other types of compounds, and this application does not make special limitations thereon. In some embodiments of this application, the hole blocking layer 340 is HB-1.

[0122] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from, but not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and no special limitation is made in this application. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0123]

[0124] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-1 and LiQ of this application.

[0125] In this application, the cathode 200 can include a cathode material, which is a material with a small work function that helps electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0126] Optionally, an electron injection layer 360 can also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 can include inorganic materials such as alkali metal sulfides and alkali metal halides, or can include complexes of alkali metals and organic substances. In some embodiments of this application, the electron injection layer 360 can include ytterbium (Yb).

[0127] The third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.

[0128] According to one embodiment, as Figure 2 shown, the provided electronic device is the electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and can include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0129] The following combines synthesis examples to specifically illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereby.

[0130] Compounds for which the synthesis method is not mentioned in this application are all raw material products obtained through commercial channels.

[0131] Synthesis Example

[0132] I. Synthesis of Intermediate F-X

[0133] Synthesis of Intermediate F-1

[0134]

[0135] Add 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (13.36 g, 50 mmol), acetic anhydride (130 mL) into a 500 mL three-necked flask equipped with a nitrogen protection and a condensation reflux device. Protect with nitrogen, start stirring, control the temperature at 0 °C - 5 °C, dropwise add concentrated nitric acid (68%) (5.56 g, 60 mmol). After dropping, keep the reaction at this temperature for 2 h. Stop stirring, slowly add the reaction solution into 1000 mL of ultrapure water. Add 200 mL of dichloromethane to the reaction solution, stir and separate the layers. The aqueous phase is extracted with dichloromethane twice (100 mL × 2). Combine the organic phases and wash them with ultrapure water five times (200 mL × 5). Separate the layers, and dry the organic phase with anhydrous sodium sulfate. Purify by passing through a silica gel column, and the eluent is dichloromethane:n-heptane (volume ratio) = 1:4 to obtain Intermediate D-1 (7.80 g, yield 50%).

[0136]

[0137] Add Intermediate D-1 (15.61 g, 50 mmol), phenylboronic acid (6.70 g, 55 mmol), potassium carbonate (13.8 g, 100 mmol), tetrabutylammonium bromide (1.6 g, 5 mmol), toluene (160 mL), ethanol (40 mL) and ultrapure water (40 mL) into a 500 mL three-necked flask equipped with a nitrogen protection and a condensation reflux device. Protect with nitrogen, start heating and stirring, raise the temperature to 40 °C, add tetrakis(triphenylphosphine)palladium (0.57 g, 0.5 mmol), raise the temperature to reflux, and react for 12 h. When the reaction solution cools to room temperature, extract with 150 mL of toluene, wash with 200 mL of ultrapure water and separate the layers. Dry the organic phase with anhydrous sodium sulfate, and separate the product by passing through a column. The eluent is petroleum ether:ethyl acetate (6:1) (volume ratio) to obtain Intermediate E-1 (9.28 g, yield 60%).

[0138]

[0139] Add intermediate E-1 (15.47 g, 50 mmol), triphenylphosphine (26.22 g, 100 mmol), and o-dichlorobenzene (150 mL) to a 500 mL three-necked flask equipped with a nitrogen protection and condensation reflux device; protect with nitrogen, turn on heating and stirring, heat up to reflux, and react for 24 hours; then completely distill out o-dichlorobenzene, separate the product by column chromatography, and the eluent is petroleum ether: ethyl acetate (3:1) (volume ratio) to obtain intermediate F-1 (8.32 g, yield 60%).

[0140] Refer to the synthesis method of intermediate F-1 to synthesize intermediate F-X shown in Table 1. The difference is that raw material 1 is used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, and raw material 2 is used instead of phenylboronic acid to prepare the compounds in Table 1 below. The main raw materials used, the structures of the synthesized intermediates, and the total yields are shown in Table 1.

[0141] Table 1

[0142]

[0143] II. Synthesis of Compounds

[0144] 1. Synthesis of Compound A-1

[0145]

[0146] Add intermediate F-1 (13.85 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), potassium carbonate (13.8 g, 100 mmol), and N,N-dimethylformamide (DMF) (140 mL) to a 500 mL three-necked flask equipped with a nitrogen protection and condensation reflux device; protect with nitrogen, turn on heating and stirring, heat up to 60 °C, add copper(I) iodide (0.95 g, 5 mmol), 1,10-phenanthroline (0.90, 5 mmol), and 18-crown-6 (1.32, 5 mmol); heat up to reflux and react for 12 hours; wait for the reaction solution to cool to room temperature, extract with 150 mL of toluene, wash with 200 mL of ultrapure water, separate the layers, dry the organic phase with anhydrous sodium sulfate, separate the product by column chromatography, and the eluent is petroleum ether: ethyl acetate (8:1) (volume ratio) to obtain intermediate G-1 (12.54 g, yield 71%).

[0147]

[0148] Add intermediate G-1 (17.67 g, 50 mmol), dichloromethane (DCM) (200 mL) into a 500 mL three-necked flask equipped with a nitrogen protection and a condensation reflux device. Protect with nitrogen, start stirring, control the temperature at 0 °C - 10 °C, and add N-bromosuccinimide (NBS) (8.89 g, 50 mmol) in batches. After addition, keep the reaction at a constant temperature for 5 h; stop stirring; add 100 mL of ultrapure water, stir and separate the liquid. The aqueous phase is extracted twice with dichloromethane (100 mL × 2). Combine the organic phases, wash five times with ultrapure water (200 mL × 5), separate the liquid, and dry the organic phase with anhydrous sodium sulfate; separate and purify by passing through a silica gel column. The eluent is dichloromethane:n-heptane (volume ratio) = 1:3 to obtain intermediate H-1 (13.18 g, yield 61%).

[0149]

[0150] Add intermediate H-1 (21.62 g, 50 mmol), 9-phenyl-3-carbazoleboronic acid (15.79 g, 55 mmol), potassium carbonate (13.8 g, 100 mmol), tetrabutylammonium bromide (1.6 g, 5 mmol), toluene (210 mL), ethanol (50 mL) and ultrapure water (50 mL) into a 1000 mL three-necked flask equipped with a nitrogen protection and a condensation reflux device; protect with nitrogen, start heating and stirring, raise the temperature to 40 °C, and add tetrakis(triphenylphosphine)palladium(0) (0.57 g, 0.5 mmol); raise the temperature to reflux and react for 18 hours; wait for the reaction solution to cool to room temperature, extract with 150 mL of toluene, wash with 200 mL of ultrapure water, separate the liquid, dry the organic phase with anhydrous sodium sulfate, and separate and purify the product by passing through a column. The eluent is n-heptane:dichloromethane (3:1) (volume ratio) to obtain compound A-1 (19.33 g, yield 65%), mass spectrometry: m / z = 595.30 (M + H) + 。

[0151] Synthesize the compounds shown in Table 2 with reference to the synthesis method of intermediate G-1. The difference is that raw material 3 is used instead of intermediate F-1, and raw material 4 is used instead of iodobenzene to prepare the compounds in Table 2 below. The main raw materials used, the structures of the synthesized intermediates and the total yields are shown in Table 2.

[0152] Table 2 Compound Structure Preparation

[0153]

[0154] 2. Synthesis of intermediate I-1

[0155]

[0156] Add intermediate F-4 (17.84 g, 50 mmol), bis(pinacolato)diboron (15.2 g, 60 mmol) and 1,4-dioxane (220 mL) into a 500 mL three-necked flask equipped with a nitrogen protection and condensation reflux device. Protect with nitrogen, start stirring and heating. When the temperature rises to 50 °C, add potassium acetate (9.8 g, 100 mmol), X-Phos (0.47 g, 1 mmol), Pd2(dba)3 (0.45 g, 0.5 mmol) in sequence; raise the temperature to reflux and react for 5 h; stop stirring and heating, and wait for the temperature to drop to room temperature; add 200 mL of dichloromethane and 150 mL of ultrapure water to the reaction solution, stir and separate the liquid. The aqueous phase is extracted twice with dichloromethane (100 mL × 2). Combine the organic phases, wash three times with ultrapure water (200 mL × 3), separate the liquid, and dry the organic phase with anhydrous sodium sulfate; separate and purify by silica gel column chromatography, and the eluent is dichloromethane:n-heptane (volume ratio) = 1:3 to obtain intermediate I-1 (14.56 g, yield 65%).

[0157] Synthesize the compounds shown in Table 3 with reference to the synthesis method of compound A-1, except that intermediate 1 is used instead of intermediate F-1, raw material 5 is used instead of iodobenzene, and raw material 6 is used instead of 9-phenyl-3-carbazoleboronic acid to prepare the compounds in Table 3 below.

[0158] Table 3 Compound Structures and Characterization Data

[0159]

[0160]

[0161]

[0162]

[0163] 1H NMR data of some intermediates and compounds are shown in Table 4 below:

[0164] Table 4

[0165]

[0166]

[0167] Preparation and evaluation of organic electroluminescent devices:

[0168] The embodiments of the present application also provide an organic electroluminescent device, including an anode, a cathode, and a functional layer between the anode and the cathode. The functional layer includes the above nitrogen-containing compound of the present application. Hereinafter, the organic electroluminescent device of the present application will be described in detail by way of examples. However, the following examples are only examples of the present application and do not limit the present application.

[0169] Example 1: Preparation of green organic electroluminescent device

[0170] The anode was prepared by the following process: ITO / Ag / ITO with a thickness of The ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns. The surface was treated with 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.

[0171] HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of Then, NPB is vacuum evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer is formed by a plurality of holes.

[0172] TAPC is vacuum evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is

[0173] On the second hole transport layer, compound A-1: GH-1: Ir(ppy)2acac was co-evaporated at a weight ratio of 45%: 45%: 10% to form a layer with a thickness of Organic light-emitting layer (EML, green light-emitting layer)

[0174] On the organic light-emitting layer, compound HB-1 is vacuum-deposited to form The hole blocking layer (HBL) is then formed by mixing compound ET-1 and LiQ in a weight ratio of 1:1 and evaporating 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 and vacuum-deposited on the electron injection layer at a deposition rate ratio of 1:9 to form a layer with a thickness of cathode.

[0175] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of green organic electroluminescent devices.

[0176] Embodiments 2 to 20:

[0177] An organic electroluminescent device was prepared in the same manner as in Example 1, except that, when preparing the organic light-emitting layer, the compound in Table 5 was used instead of the compound A-1 in Example 1.

[0178] Comparative Examples 1-2:

[0179] The organic electroluminescent devices were prepared by the same method as in Example 1, except that when preparing the organic light-emitting layer, Compound A-1 was replaced with Compound 1 and Compound 2 in Table 5 below, respectively.

[0180] Among them, when preparing the organic electroluminescent device, the structures of the respective materials used in the comparative examples and the examples are as follows:

[0181]

[0182]

[0183] The performance of the green organic electroluminescent devices prepared in Examples 1-20 and Comparative Examples 1-2 was tested. Specifically, the IVL performance of the devices was tested under the condition of 10 mA / cm 2 and the T95 device lifetime was tested under the condition of 20 mA / cm 2 . The test results are shown in Table 5.

[0184] Table 5

[0185]

[0186] Referring to the above table, it can be seen that the performance of the organic electroluminescent devices of Examples 1-20 has been greatly improved compared with those of Comparative Examples 1 and 2. Specifically, the operating voltages of the devices are close, the current efficiency of the examples is increased by at least 16.9%, and the T95 lifetime is increased by at least 13.4%.

[0187] The nitrogen-containing compound of the present application has a tetramethylcyclohexane-fused 3,3-bicarbazole group as the core structure. This structure can reduce the intermolecular force and crystallinity without affecting the aromatic conjugation degree of the molecule, thereby improving the stability and film-forming property of the amorphous state of the material; when the nitrogen-containing compound of the present application is used as the host material of the organic light-emitting layer in an organic electroluminescent device, the device lifetime can be effectively improved and the efficiency can be improved to a certain extent.

[0188] The preferred embodiments of the present application have been described in detail above. However, the present application is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. A nitrogen-containing compound, characterized in that, The nitrogen-containing compound has a structure represented by Formula 1-A or Formula 1-C: L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted phenylene group; The substituents in L1 and L2 are the same or different, and each independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, tert-butyl group or phenyl group; Ar1 and Ar2 are each 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 terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group; R1 and R2 are the same and are selected from deuterium; n1 represents the number of R1 and is selected from 0, 1, 2 or 3; n2 represents the number of R2 and is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

2. The nitrogen-containing compound according to claim 1, wherein and each independently selected from the group consisting of the following groups:

3. The nitrogen-containing compound according to claim 1, wherein The nitrogen-containing compound is selected from the group consisting of the following compounds:

4. An electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer contains the nitrogen-containing compound according to any one of claims 1-3; The electronic component is an organic electroluminescent device; The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the nitrogen-containing compound.

5. An electronic device, characterized in that, Including the electronic component according to claim 4.

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