CN114075185A - Nitrogen-containing compound, electronic element comprising same and electronic device - Google Patents

Nitrogen-containing compound, electronic element comprising same and electronic device Download PDF

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CN114075185A
CN114075185A CN202110120037.8A CN202110120037A CN114075185A CN 114075185 A CN114075185 A CN 114075185A CN 202110120037 A CN202110120037 A CN 202110120037A CN 114075185 A CN114075185 A CN 114075185A
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杨敏
韩超
南朋
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic element containing the same and an electronic device, wherein the structure of the nitrogen-containing compound is shown as a chemical formula 1:
Figure DDA0002921692780000011

Description

Nitrogen-containing compound, electronic element comprising same and electronic device
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to a nitrogen-containing compound, and an electronic element and an electronic device comprising the same.
Background
With the pace of globalization being accelerated, scientific and technological knowledge is exchanged comprehensively, which is the pace of scientific and technological progress. Under the environment, the field of organic flat panel display is rapidly advanced, and the organic light emitting diode (also called organic electroluminescence) is rapidly developed and has been in the initial scale of industrialization. The OLED material is mainly applied to the display field and the illumination field, wherein the display field mainly focuses on the display field of televisions, computers, mobile phones and the like and the illumination field, and the display field mainly focuses on display screens of televisions, computers, mobile phones and the like. The OLED material has the advantages of low working voltage, high reaction speed, flexibility and folding, high luminous brightness, high efficiency and the like, so that the OLED material is sought in the industry. Therefore, the LED light source is known as the illusion technology of future light sources and display technologies of human beings.
The radiative transitions of singlet and triplet excitons back to the ground state under the influence of an external electric field produce fluorescence and phosphorescence, respectively. OLED materials are classified into fluorescent materials and phosphorescent materials according to the principle of light emission. Due to the spin-orbit coupling effect of the heavy metal, the phosphorescent material can simultaneously utilize 25% of singlet excitons and 75% of triplet excitons, so that the luminous efficiency is remarkably improved. However, phosphorescent materials face two major problems of concentration quenching and triplet state minactization, and cannot achieve high-efficiency luminescence. In the development of this industrialized hot tide, how to improve the efficiency and prolong the lifetime of the device is a crucial issue.
It is to be noted that the information disclosed in the above background section is only for enhancement of understanding of the background of the present application and therefore may include information that does not constitute prior art known to a person of ordinary skill in the art.
Disclosure of Invention
It is an object of the present invention to overcome the above-mentioned deficiencies in the prior art and to provide a nitrogen-containing compound, an electronic component and an electronic device including the same, which can improve the light-emitting efficiency and prolong the lifetime of the device.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structural formula consisting of structures represented by chemical formulas 1 and 2:
Figure BDA0002921692760000011
wherein, represents the connection point of chemical formula 1 and chemical formula 2, any two adjacent connection points in chemical formula 2 are connected with chemical formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted aryl with 6-18 carbon atoms;
X1、X2 and X3Are the same or different and are each independently selected from N or CH, and X1、X2 and X3Is N;
R1、R2 and R3The same or different from each other, and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, and heteroaryl having 3 to 30 carbon atoms;
R1、R2、R3with RiIs represented by n1～n3With niIs represented by niRepresents RiI is a variable, represents 1,2 and 3, and when i is 1 and 3, niSelected from 0, 1,2, 3 or 4; when i is 2, ni is selected from 0, 1 or 2; and when n isiWhen greater than 1, any two niThe same or different;
L、L1 and L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1 and Ar2The same or different, and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the substituent in Y is selected from deuterium, a halogen group, a cyano group, an aryl group with 6-12 carbon atoms and an alkyl group with 1-5 carbon atoms;
the L, L1 and L2Wherein the substituents are the same or different and are each independentlySelected from deuterium, halogen, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;
ar is1 and Ar2Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, and alkoxy having 1 to 10 carbon atoms.
The nitrogen-containing compound provided by the application comprises a nitrogen heterocyclic structure (pyridine, pyrimidine or triazine), a structure formed by fusing phenanthrene and aryl-substituted nitrogen-containing five-membered ring (thiazole and oxazole). When the structure is combined as a main material of the organic light-emitting layer according to a specific mode, the target compound has higher electron mobility, so that the balance of electrons and holes in the organic light-emitting layer is favorably realized, the recombination area of the electrons and the holes in the light-emitting layer is widened, the light-emitting efficiency of electroluminescence is improved, the driving voltage of the organic electroluminescence is reduced, and the service life of a device is prolonged. The nitrogen-containing compound is more suitable for being used as an electronic type host material in a mixed host of an organic electroluminescent device, and is particularly suitable for being used as an electronic host material of a red light device. When the nitrogen-containing compound is used for a luminescent layer material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, the luminescent efficiency of the device is improved, and the service life of the device is prolonged.
According to a second aspect of the present application, there is provided an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, there is provided an electronic device including the above electronic component.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application.
In the drawings:
fig. 1 is a schematic structural view of an embodiment of an organic electroluminescent device according to the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the subject matter of the present application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring major technical ideas of the application.
The present application provides a nitrogen-containing compound having a structural formula consisting of structures represented by chemical formula 1 and chemical formula 2:
Figure BDA0002921692760000031
wherein, represents the connection point of chemical formula 1 and chemical formula 2, any two adjacent connection points in chemical formula 2 are connected with chemical formula 1, R1、R2Or R3Must include at least one of chemical formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted aryl with 6-18 carbon atoms;
X1、X2 and X3Are the same or different and are each independently selected from N or CH, and X1、X2 and X3Is N;
R1、R2 and R3The same or different from each other, and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, and heteroaryl having 3 to 30 carbon atoms;
R1、R2、R3with RiIs represented by n1～n3With niIs represented by niRepresents RiI is a variable, represents 1,2 and 3, and when i is 1 and 3, niSelected from 0, 1,2, 3 or 4; when i is 2, ni is selected from 0, 1 or 2; and when n isiWhen greater than 1, any two niThe same or different;
L、L1 and L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1 and Ar2The same or different, and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the substituent in Y is selected from deuterium, a halogen group, a cyano group, an aryl group with 6-12 carbon atoms and an alkyl group with 1-5 carbon atoms;
the L, L1 and L2Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms and alkoxy with 1-10 carbon atoms;
ar is1 and Ar2Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, and alkoxy having 1 to 10 carbon atoms.
Alternatively, the nitrogen-containing compound has formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 2-1, formula 2-2, formula 2-3, formula 2-4, formula 2-5, formula 2-6, formula 2-7, formula 2-8, formula 3-1, formula 3-2, formula 3-3, formula 3-4, formula 3-5, formula 3-6, formula 3-7, formula 3-8, formula 4-1, formula 4-2, formula 4-3, formula 4-4, formula 4-5, formula 4-6, formula 4-7, formula 4-8, formula 5-1, formula 5-2, formula 5-3, A structure represented by any one of formulae 5-4, formulae 5-5, formulae 5-6, formulae 5-7, and formulae 5-8:
Figure BDA0002921692760000041
Figure BDA0002921692760000051
Figure BDA0002921692760000061
Figure BDA0002921692760000071
in the present application, the description "independently selected" and "independently selected" are used interchangeably and should be understood in a broad sense, which means that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other. For example,') "
Figure BDA0002921692760000072
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' 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' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein the substituent Rc may be, for example, deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms optionally substituted with deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, or alkoxy having 1 to 10 carbon atoms.
In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12. For example: ar is
Figure BDA0002921692760000073
The number of carbon atoms is 7; l is
Figure BDA0002921692760000074
The number of carbon atoms is 12.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. Further, the alkyl group may be substituted or unsubstituted.
Preferably, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3 to 10 carbon atoms, numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "3 to 10 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. The cycloalkyl group may be a small, ordinary ring having 3 to 10 carbon atoms. In addition, cycloalkyl groups may be substituted or unsubstituted. For example, cyclohexane. Heterocycloalkyl means a cycloalkyl in which one or more of the carbon atoms is replaced by a heteroatom such as B, N, O, S, P, Si or Se.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
Figure BDA0002921692760000081
and the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 20, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 18, in other embodimentsThe number of carbon atoms in the aryl group may be 6 to 12. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, or 30, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, alkoxy groups, and the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.
In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracyl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can 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, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl and the N-pyridylcarbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The "heteroaryl" groups herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 5 to 12. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, alkoxy groups, and the like. It is 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 substituent on the heteroaryl group.
In the present application, specific examples of the heteroaryl group as the substituent include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
In the present application, the term "non-aligned bond" meansSingle bonds extending from the ring system
Figure BDA0002921692760000091
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).
Figure BDA0002921692760000092
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the dibenzofuranyl group represented by formula (X '-1) to formula (X' -4) includes any of the possible attachment means shown in formulas (X '-1) to (X' -4).
Figure BDA0002921692760000093
The meaning of the connection or substitution is the same as that of the connection or substitution, and will not be described further.
In one embodiment of the present application, Y is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl;
alternatively, the substituents in Y are selected from phenyl, naphthyl.
In one embodiment of the present application, Y is selected from the group consisting of:
Figure BDA0002921692760000094
in one embodiment of the present application, said L, L1、L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
Optionally, said L, L1、L2Wherein the substituent is selected from deuterium, a halogen group, a cyano group, a phenyl group, and an alkyl group having 1 to 5 carbon atoms.
Specifically, the L, L1、L2Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
Optionally, said L, L1、L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.
Further optionally, said L1，L2Each independently selected from a single bond or phenylene.
In another embodiment of the present application, L is selected from a single bond or the group consisting of:
Figure BDA0002921692760000101
in one embodiment of the present application, the Ar1 and Ar2Each independently selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
Optionally, the Ar is1、Ar2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, and an alkyl group having 1 to 5 carbon atoms.
Specifically, Ar is1 and Ar2Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
In a further alternative,ar is1 and Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted N-phenylcarbazolyl.
In another embodiment of the present application, Ar is1 and Ar2Each independently selected from the group consisting of substituted or unsubstituted W, unsubstituted W being selected from the group consisting of:
Figure BDA0002921692760000102
wherein, represents a chemical bond; substituted W has one or more substituents thereon, each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of W is more than 1, the substituents may be the same or different.
Alternatively, Ar1 and Ar2Each independently selected from the group consisting of:
Figure BDA0002921692760000103
Figure BDA0002921692760000111
optionally, the nitrogen-containing compound is selected from the group consisting of the compounds as set forth in claim 9.
The present application also provides an electronic component comprising an anode and a cathode disposed opposite one another, and at least one functional layer comprising the nitrogen-containing compound of the present application interposed between the anode and the cathode.
In one embodiment, an organic electroluminescent device is provided, the device structure is shown in fig. 1, the organic electroluminescent device includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer, the functional layer 300 includes a hole injection layer 310, a hole transport layer 320, an organic electroluminescent layer 330, a hole blocking layer 340, an electron transport layer 350, and an electron injection layer 360; the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322; the hole injection layer 310, the hole transport layer 320, the organic electroluminescent layer 330, the hole blocking layer 340, the electron transport layer 350, and the electron injection layer 360 may be sequentially formed on the anode 100, and the organic electroluminescent layer 330 may contain an organic compound described in the first aspect of the present application, and preferably at least one of the compounds 1 to 376.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably comprising a transparent electrode comprising Indium Tin Oxide (ITO) as anode.
Alternatively, the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds, which are not specifically limited herein. For example, the hole transport layer 320 may include a first hole transport layer 321 and a second hole transport layer 322; the first hole transport layer 321 is adjacent to the second hole transport layer 322 and is closer to the anode than the second hole transport layer 322. For example, in one embodiment of the present application, the first hole transporting layer 321 is composed of the compound HT-01, and the second hole transporting layer 322 is composed of the compound HT-02.
Alternatively, the organic electroluminescent layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic electroluminescent layer 330 may be composed of a host material and a guest material, and holes and electrons injected into the organic light emitting layer 330 may be combined 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, so that the guest material can emit light.
The host material of the organic electroluminescent layer 330 is a nitrogen-containing compound provided herein. The nitrogen-containing compound provided by the application comprises a nitrogen heterocyclic structure (pyridine, pyrimidine or triazine), a structure formed by fusing phenanthrene and aryl-substituted nitrogen-containing five-membered ring (thiazole and oxazole). When the structures are combined with each other and are jointly used as a main material of the organic light-emitting layer, the hole mobility of the light-emitting layer is improved due to the larger electron cloud density, so that the balance between electrons and holes in the organic light-emitting layer is facilitated, the light-emitting efficiency of electroluminescence is improved, and the driving pressure of the organic electroluminescence is reduced. The condensed structure of phenanthrene and the nitrogenous five-membered ring has larger space volume, and the connection mode simultaneously enables the whole molecular structure to have better spatial configuration, so that the molecular structure has better rigidity, the T1 energy level of the material is improved while the mobility is higher, and the crystallinity is lower. The nitrogen-containing compound is more suitable for being used as an electronic type host material in a mixed host of an organic electroluminescent device, and is particularly suitable for being used as an electronic host material of a red light device. When the nitrogen-containing compound is used for a luminescent layer material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, the luminescent efficiency of the device is improved, and the service life of the device is prolonged.
The guest material of the organic electroluminescent 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, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq)2(acac)。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, the electron transport layer 350 may be composed of BTB and LiQ.
Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.
Optionally, a hole injection layer 310 may be further disposed 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 made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. In one embodiment of the present application, the hole injection layer 310 may be composed of m-MTDATA.
Optionally, an electron injection layer 360 may be further disposed 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 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).
The application also provides an electronic device, which comprises the electronic element.
For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the first electronic device 400 has the organic electroluminescent device, the same advantages are obtained, and the description of the present application is omitted.
The present application will be described in detail below with reference to examples, but the following description is intended to explain the present application, and not to limit the scope of the present application in any way.
Synthetic examples
One skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare a number of other compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully accomplished by those skilled in the art by modification, such as appropriate protection of interfering groups, by the use of other known reagents other than those described herein, or by some routine modification of reaction conditions. In addition, the synthesis of the counter compounds disclosed herein.
(1) Synthesis of intermediate C-1
Figure BDA0002921692760000121
A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then reactant A-1(5.0g, 18.2mmol), reactant B-1(3.37g,18.2mmol), tetrakis (triphenylphosphine) palladium (1.05g,0.91mmol), potassium carbonate (7.56g, 54.7mmol), tetrabutylammonium bromide (0.25g,0.91mmol) and a mixed solvent of toluene (40mL), ethanol (20mL) and deionized water (10mL) were added. Starting stirring, heating to 75-85 ℃ for reaction for 12h, and cooling to room temperature after the reaction is finished. Adding toluene (100mL) for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by column chromatography on silica gel using n-heptane as eluent and then recrystallized using a dichloromethane/ethyl acetate system (1:5) to give intermediate C-1(4.56g, yield 75%).
Referring to the synthesis of intermediate C-1, intermediates C-X shown in Table 1 below were synthesized, wherein X is 1 to 14, using reactant A-1, reactant A-2, reactant A-3, reactant A-4, reactant A-5, reactant A-6 and reactant A-7 in place of reactant A-1, reactant B-1 and reactant B-2 in place of reactant B-1, and the intermediates C-X were prepared as shown in Table 1 below:
TABLE 1
Figure BDA0002921692760000131
Figure BDA0002921692760000141
Figure BDA0002921692760000151
(2) Synthesis of intermediate D-1
Figure BDA0002921692760000161
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a constant-pressure dropping funnel for replacement for 15min, sequentially adding methoxymethyl triphenyl phosphonium chloride (5.9g,17.2mmol) and tetrahydrofuran (50mL), reducing the system temperature to-10 to-15 ℃, adding potassium tert-butoxide (2.18g,19.5mmol) into the flask in batches, controlling the system temperature to-10 to-5 ℃, keeping the temperature for 2h, weighing intermediate C-1(5.0g,15.0mmol), dissolving the intermediate C-1 with 15 times of tetrahydrofuran, dropping the intermediate C-1 into the system by using the constant-pressure dropping funnel after the intermediate C-1(5.0g,15.0mmol) is dissolved, finishing dropping for about 1h, controlling the system temperature to be about-5 ℃ during the period, keeping the temperature for reaction for 2h, and after the reaction is finished, raising the temperature to room temperature. Adding toluene (100mL) for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by silica gel column chromatography using toluene as eluent to give intermediate D-1(3.79g, yield 70%).
Referring to the synthesis of intermediate D-1, intermediates D-X shown in Table 2 below were synthesized, wherein X is 1 to 14, and intermediate C-X was used instead of intermediate C-1, and the intermediates D-X were prepared as shown in Table 2 below:
TABLE 2
Figure BDA0002921692760000162
Figure BDA0002921692760000171
Figure BDA0002921692760000181
Figure BDA0002921692760000191
(3) Synthesis of intermediate E-1
Figure BDA0002921692760000192
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, sequentially and respectively adding an intermediate D-1(5.0g,13.8mmol), an Eton reagent (0.99g,4.14mmol) and chlorobenzene (50mL), heating, refluxing and stirring for reaction for 1h, and cooling to room temperature after the reaction is finished. Adding dichloromethane (100mL) into the system, stirring, adding water (100mL) and sodium bicarbonate (5.0g), fully stirring, standing for liquid separation, washing an organic phase to be neutral, extracting with dichloromethane (100mL), combining the organic phases, adding anhydrous magnesium sulfate to dry the organic phase, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by silica gel column chromatography using toluene as eluent to give intermediate E-1(2.96g, yield 35%).
Referring to the synthesis of intermediate E-1, intermediates E-X shown in Table 3 below were synthesized, wherein X is 1 to 27, using intermediate D-X instead of intermediate D-1, and intermediates E-X were prepared as shown in Table 3 below:
TABLE 3
Figure BDA0002921692760000193
Figure BDA0002921692760000201
Figure BDA0002921692760000211
Figure BDA0002921692760000221
Figure BDA0002921692760000231
Figure BDA0002921692760000241
Figure BDA0002921692760000251
(4) Synthesis of intermediate F-1
Figure BDA0002921692760000252
Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for 15min, adding an intermediate E-1(5.0g, 15.2mmol), pinacol diboron diboronate (3.9g, 15.2mmol), tris (dibenzylideneacetone) dipalladium (0.14g, 0.15mmol), 2-dicyclohexyl-phosphorus-2 ', 4', 6 ' -triisopropyl-biphenyl (0.14g, 0.30mmol), potassium acetate (4.5g, 45.5mmol) and 1, 4-dioxane (50mL), heating to 105 ℃ and 115 ℃, carrying out reflux stirring reaction for 5h, and cooling to room temperature after the reaction is finished. Extracting the reaction solution with dichloromethane and water, drying the organic phase with anhydrous magnesium sulfate, filtering, passing through a short silica gel column, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate F-1(5.0g, yield 78%).
Referring to the synthesis of intermediate F-1, intermediates F-X shown in Table 4 below were synthesized, wherein X is 1 to 25, and intermediate E-X was used instead of intermediate E-1, and the intermediates F-X were prepared as shown in Table 4 below:
TABLE 4
Figure BDA0002921692760000261
Figure BDA0002921692760000271
Figure BDA0002921692760000281
Figure BDA0002921692760000291
Figure BDA0002921692760000301
Figure BDA0002921692760000311
Figure BDA0002921692760000321
Figure BDA0002921692760000331
(5) Synthesis of intermediate G-1
Figure BDA0002921692760000332
A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and intermediate F-1(5.0g, 11.9mmol), reactant SM-1(2.4g, 11.9mmol), tetrakis (triphenylphosphine) palladium (0.68g, 0.6mmol), potassium carbonate (4.9g, 35.6mmol), tetrabutylammonium bromide (0.16g, 0.59mmol) were added, and a mixed solvent of toluene (40mL), ethanol (20mL), and deionized water (10mL) was added. Starting stirring, heating to 75-85 ℃ for reaction for 12h, and cooling to room temperature after the reaction is finished. Adding toluene (100mL) for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by column chromatography on silica gel using n-heptane as a mobile phase and then recrystallized using a dichloromethane/ethyl acetate system to give intermediate G-1(3.8G, yield 78%).
Referring to the synthesis method of intermediate G-1, intermediates G-X shown in table 5 below were synthesized, wherein X is 1 to 4, intermediate F-2 and intermediate F-6 were used instead of intermediate F-1, and reactant SM-2, reactant SM-3 and reactant SM-4 were used instead of reactant SM-1, and the prepared intermediate G-X was shown in table 5 below:
TABLE 5
Figure BDA0002921692760000333
Figure BDA0002921692760000341
(5) Synthesis of Compound 100
Figure BDA0002921692760000342
A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then intermediate F-1(5.0g, 11.9mmol), reaction H-1(3.18g, 11.9mmol), tetrakis (triphenylphosphine) palladium (0.68g, 0.59mmol), potassium carbonate (4.92g, 35.6mmol), tetrabutylammonium bromide (0.16g, 0.59mmol) and a mixed solvent of toluene (40mL), ethanol (20mL) and deionized water (10mL) were added. Starting stirring, heating to 75-85 ℃ for reaction for 12h, and cooling to room temperature after the reaction is finished. Adding toluene (100mL) for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by column chromatography on silica gel using n-heptane as the mobile phase and then recrystallized using a dichloromethane/ethyl acetate system to give compound 100(4.81g, yield 77%), ms spectrum: 527.2[ M + H ] M/z]+。
Referring to the synthesis of compound 100, compound X shown in table 6 below was synthesized by substituting intermediate F-X or intermediate G-X for intermediate F-1 and reactant H-X for reactant H-1, and was prepared as shown in table 6 below:
TABLE 6
Figure BDA0002921692760000351
Figure BDA0002921692760000361
Figure BDA0002921692760000371
Figure BDA0002921692760000381
Figure BDA0002921692760000391
Figure BDA0002921692760000401
Figure BDA0002921692760000411
Figure BDA0002921692760000421
Figure BDA0002921692760000431
Figure BDA0002921692760000441
Figure BDA0002921692760000451
Figure BDA0002921692760000461
Figure BDA0002921692760000471
Part of the compound NMR data are shown in Table 7 below
TABLE 7
Figure BDA0002921692760000472
Preparation and performance evaluation of organic electroluminescent device
Example 1
Red organic electroluminescent device
Will have a thickness of
Figure BDA0002921692760000481
The anode 100ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode 200, an anode 100 and an insulating layer pattern using a photolithography process, and subjected to uv ozone and O2:N2The plasma is used for surface treatment to increase the work function of the anode 100 (experimental substrate), and the organic solvent is used for cleaning the surface of the ITO substrate to remove scum and oil stains on the surface of the ITO substrate.
The compound m-MTDATA (4,4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine) (structural formula shown below) was vacuum evaporated on the experimental substrate to a thickness of
Figure BDA0002921692760000482
Hole injection layer 310 (HIL); and a compound HT-01 is vacuum evaporated over the hole injection layer 310(HIL) to a thickness of
Figure BDA0002921692760000483
First hole transport layer 321(HTL 1). A layer of HT-02 is vacuum evaporated on the first hole transport layer 321(HTL1) to a thickness of
Figure BDA0002921692760000484
Second hole transport layer 322(HTL 2).
On the second hole transport layer 322(HTL2), Compound 100 was reacted with Ir (piq)2(acac) at 95%: 5% of the dopant ratio was co-evaporated to a thickness of
Figure BDA0002921692760000485
The red light emitting layer 330 (EML).
BTB and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation
Figure BDA0002921692760000486
A thick electron transport layer 350(ETL), and then Yb is deposited on the electron transport layer 350(ETL) to form a layer having a thickness of
Figure BDA0002921692760000487
Electron injection layer 360 (EIL).
Magnesium (Mg) and silver (Ag) were deposited on the electron injection layer by vacuum deposition at a film thickness ratio of 1:9 to form a layer having a thickness of
Figure BDA0002921692760000488
The cathode 200.
Further, a protective layer is deposited on the cathode 200 to a thickness of
Figure BDA0002921692760000489
Forming a capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 34
A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compounds shown in table 6 were used instead of the compound 100 in forming the emission layer (EML).
Comparative example 1
A red organic electroluminescent device was produced in the same manner as in example 1, except that compound a was used instead of compound 100.
Comparative example 2
A red organic electroluminescent device was produced in the same manner as in example 1, except that the compound B was used instead of the compound 100.
Wherein, m-MTDATA, HT-01, HT-02, Ir (piq)2The structural formulas of (acac), BTB, LiQ, CP-01, compound A and compound B are shown in the following table 8:
TABLE 8
Figure BDA00029216927600004810
Figure BDA0002921692760000491
For the organic electroluminescent device prepared as above, at 20mA/cm2The properties of the device were analyzed under the conditions of (1), and the results are shown in Table 9.
TABLE 9 Performance test results of red organic electroluminescent devices
Figure BDA0002921692760000492
Figure BDA0002921692760000501
From the results of table 9, it is understood that the organic electroluminescent devices prepared in examples 1 to 34 have improved properties in the OLED devices having the compound as the organic electroluminescent layer, compared to the comparative examples. Wherein, compared with comparative examples 1 and 2, the driving voltage of the compound used as the light-emitting layer is reduced by at least 0.25V, the luminous efficiency is improved by at least 10.38%, and the service life is improved by at least 13.79%. From the above data, it is clear that the use of the nitrogen-containing compound of the present application as an organic electroluminescent layer of an electronic device significantly improves the luminous efficiency (Cd/a), the External Quantum Efficiency (EQE), and the lifetime (T95) of the electronic device. Therefore, the nitrogen-containing compound can be used in an organic electroluminescent layer to prepare an organic electroluminescent device with high luminous efficiency and long service life.
The compounds of the present application have improved voltage, efficiency, and lifetime compared to comparative compound B. Although only the difference is that oxazole and phenanthrene are different in concentration, compared with the compound B in the comparative example, the compound of the present application has higher electron mobility, which is beneficial to balancing electrons and holes in an organic light-emitting layer, widening the recombination region of electrons and holes in the light-emitting layer, improving the light-emitting efficiency of electroluminescence, reducing the driving voltage of the organic electroluminescence and prolonging the service life of the device.
It should be understood that this application is not intended to limit the application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are within the scope of the present application. It will be understood that the application disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute a number of alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.

Claims (11)

1. A nitrogen-containing compound, wherein the structural formula of the nitrogen-containing compound consists of the structures represented by chemical formula 1 and chemical formula 2:
Figure FDA0002921692750000011
wherein, represents the connection point of chemical formula 1 and chemical formula 2, any two adjacent connection points in chemical formula 2 are connected with chemical formula 1;
x is selected from O or S;
y is selected from substituted or unsubstituted aryl with 6-18 carbon atoms;
X1、X2 and X3Are the same or different and are each independently selected from N or CH, and X1、X2 and X3Is N;
R1、R2 and R3The same or different from each other, and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms;
R1、R2、R3with RiIs represented by n1～n3With niIs represented by niRepresents RiI isVariables, representing 1,2 and 3, when i is 1 and 3, niSelected from 0, 1,2, 3 or 4; when i is 2, ni is selected from 0, 1 or 2; and when n isiWhen greater than 1, any two niThe same or different;
L、L1 and L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1 and Ar2The same or different, and are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the substituent in Y is selected from deuterium, a halogen group, a cyano group, an aryl group with 6-12 carbon atoms and an alkyl group with 1-5 carbon atoms;
the L, L1 and L2Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group with 3-20 carbon atoms, an aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an alkyl group with 1-10 carbon atoms, a halogenated alkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms and an alkoxy group with 1-10 carbon atoms;
ar is1 and Ar2Wherein the substituents are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, and alkoxy having 1 to 10 carbon atoms.
2. The nitrogen-containing compound according to claim 1, wherein Y is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl;
preferably, the substituents in Y are selected from phenyl, naphthyl.
3. The nitrogen-containing compound of claim 1, wherein said L, L1、L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms;
preferably, said L, L1、L2Wherein the substituent is selected from deuterium, a halogen group, a cyano group, a phenyl group, and an alkyl group having 1 to 5 carbon atoms.
4. The nitrogen-containing compound of claim 1, wherein said L, L1、L2Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;
preferably, said L, L1、L2The substituent(s) in (1) is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1 and Ar2Each independently selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;
preferably, Ar is1、Ar2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, and an alkyl group having 1 to 5 carbon atoms.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1 and Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted carbazolylSubstituted N-phenylcarbazolyl;
preferably, Ar is1 and Ar2The substituent(s) is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1 and Ar2Each independently selected from the group consisting of substituted or unsubstituted W, unsubstituted W being selected from the group consisting of:
Figure FDA0002921692750000021
wherein ,
Figure FDA0002921692750000023
represents a chemical bond; substituted W has one or more substituents thereon, each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of W is more than 1, the substituents may be the same or different.
8. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0002921692750000022
Figure FDA0002921692750000031
Figure FDA0002921692750000041
Figure FDA0002921692750000051
Figure FDA0002921692750000061
Figure FDA0002921692750000071
Figure FDA0002921692750000081
Figure FDA0002921692750000091
Figure FDA0002921692750000101
Figure FDA0002921692750000111
Figure FDA0002921692750000121
Figure FDA0002921692750000131
Figure FDA0002921692750000141
Figure FDA0002921692750000151
Figure FDA0002921692750000161
Figure FDA0002921692750000171
Figure FDA0002921692750000181
Figure FDA0002921692750000191
Figure FDA0002921692750000201
Figure FDA0002921692750000211
Figure FDA0002921692750000221
Figure FDA0002921692750000231
Figure FDA0002921692750000241
Figure FDA0002921692750000251
9. an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the nitrogen-containing compound according to any one of claims 1 to 8;
preferably, the functional layer includes a light-emitting layer including the nitrogen-containing compound.
10. The electronic component according to claim 9, wherein the electronic component is an organic electroluminescent device;
preferably, the organic electroluminescent device is a red organic electroluminescent device.
11. An electronic device, characterized by comprising the electronic component of claim 9 or 10.
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