CN114292278A

CN114292278A - Nitrogen-containing compound, organic electroluminescent device, and electronic device

Info

Publication number: CN114292278A
Application number: CN202111385330.3A
Authority: CN
Inventors: 陈志伟; 王金平; 薛震
Original assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Current assignee: Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date: 2021-09-24
Filing date: 2021-11-22
Publication date: 2022-04-08
Anticipated expiration: 2041-11-22
Also published as: CN114292278B

Abstract

The application belongs to the field of organic luminescent materials, and particularly relates to a nitrogen-containing compound, an organic electroluminescent device and an electronic device. The structure of the nitrogen-containing compound is shown as a formula 1, and the nitrogen-containing compound is used in an organic electroluminescent device and can improve the performance of the device.

Description

Nitrogen-containing compound, organic electroluminescent device, and electronic device

Technical Field

The application belongs to the technical field of organic light-emitting materials, and particularly provides a nitrogen-containing compound, an organic electroluminescent device containing the nitrogen-containing compound and an electronic device containing the nitrogen-containing compound.

Background

With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. In recent years, organic electroluminescent devices (OLEDs) have gradually entered the field of vision as a new generation of display technology. Such electronic components generally include a cathode and an anode that are oppositely disposed, 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 between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the light emitting layer under the action of the electric field, electrons on the anode side also move to the light emitting layer, the electrons and the light emitting layer are combined to form excitons in the light emitting layer, the excitons are in an excited state and release energy outwards, and the process of releasing energy from the excited state to a ground state releases energy emits light outwards. At present, the organic electroluminescent device still has the problem of poor performance, and especially how to improve the service life of the device under the condition of ensuring that the device has lower driving voltage and higher luminous efficiency, still needs to be solved urgently.

Disclosure of Invention

In view of the above problems of the prior art, the present application aims to provide a nitrogen-containing compound, and an organic electroluminescent device and an electronic apparatus comprising the same. The nitrogen-containing compound is used in an organic electroluminescent device, and can improve the performance of the device.

In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound having a structure represented by formula 1:

in formula 1, X₁～X₃Are the same or different and are each independently selected from C (H) or N, and at least one is N;

L、L₁and L₂The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atomsA substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar₁and Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms, substituted or unsubstituted heteroaryl with 5-40 carbon atoms;

Ar₁、Ar₂、L、L₁and L₂Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar₁、Ar₂In (b), any two adjacent substituents form a saturated or unsaturated ring having 3 to 15 carbon atoms.

A second aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises a nitrogen-containing compound according to the first aspect of the present application.

A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.

Among the nitrogen-containing compounds of the present application, 7-oxa-7H-benzo [ DE]Anthracene

The 5 th and 6 th positions of the compound are in a structure formed by condensed indole at specific positions as a mother nucleus, the structure of the mother nucleus has stronger conjugation effect, O and N atoms contained in the mother nucleus are combined, so that the bond energy between the atoms is higher, the whole mother nucleus has better hole transmission capability, triazine and other electron-deficient electron injection groups are further introduced to the N atom in the mother nucleus, and the combination ensures that the compound has higher T₁The energy level can reduce the charge accumulation caused by the interface effect between the hole transport layer and the light emitting layer, and the triazine group and the parent nucleus have proper rotation angle in space, so that the stability of the compound can be improved. Therefore, the temperature of the molten metal is controlled,the nitrogen-containing compound is used as a main material in an organic electroluminescent device, and can further improve the luminous efficiency and the service life of the device.

Drawings

Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of 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 light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. an electronic device.

Detailed Description

The following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.

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 present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,') "

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 this application, the terms "optional" and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, any two adjacent substituents form a ring" means that any two substituents may form a ring but need not form a ring, which includes: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring.

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. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, an alkyl group, a haloalkyl group, a cycloalkyl group, or a trialkylsilyl group. In the present application, a "substituted" functional group may be substituted with 1 or 2 or more of 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, "any two adjacent substituents form a saturated or unsaturated ring having 3 to 15 carbon atoms", the saturated ring is formedThe ring may be, for example, cyclopentane

Cyclohexane

The unsaturated ring formed may be, for example, a benzene ring, a naphthalene ring or a fluorene ring

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 L₁Is a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12. For another example: ar (Ar)₁Is composed of

The number of carbon atoms is 10; l is

The number of carbon atoms is 12.

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. In this specification, both biphenyl and fluorenyl groups are referred to as aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl,Benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,

and the like.

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, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, haloalkyl, alkyl, cycloalkyl, 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 addition, in the present application, the fluorenyl group may be substituted, and when having two substituents, the two substituents may be combined with each other to form a spiro structure. Specific examples of substituted fluorenyl groups include, but are not limited to,

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, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6 to 40. For example, the number of carbon atoms of the substituted or unsubstituted aryl group 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, or the like.

In the present application, heteroaryl means a monovalent aromatic ring containing 1,2, 3,4, 5 or more heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se and S, 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. Illustratively, 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, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl is heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, reference to heteroarylene means a divalent or higher valent radical formed from a heteroaryl group further lacking one or more hydrogen atoms.

In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more than two hydrogen atoms are substituted with groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, 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, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 5 to 40. For example, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the like.

As used herein, an delocalized linkage refers to a single bond extending from a ring system

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), the formula (f) is shownThe naphthyl group is shown to be linked to other positions of the molecule through two non-positional linkages through the bicyclic ring, and the meaning of the naphthyl group includes any possible linkage shown as formulas (f-1) to (f-10).

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).

An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).

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

In the present application, the halogen group may include fluorine, iodine, bromine, chlorine.

In the present application, the number of carbon atoms of the aryl group as the substituent may be 6 to 18, and the number of carbon atoms is specifically 6, 10, 12, 13, 14, 15, 16, 18, etc., and specific examples of the aryl group include, but are not limited to, phenyl, naphthyl, biphenyl, phenanthryl, anthracyl, fluorenyl, etc.

In the present application, the number of carbon atoms of the heteroaryl group as the substituent may be 5 to 18, specific examples of the number of carbon atoms are 5, 8, 9,10, 12, 13, 14, 15, 18 and the like, and specific examples of the heteroaryl group include, but are not limited to, a pyridyl group, a quinolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group and the like.

In the present application, the number of carbon atoms of the trialkylsilyl group as the substituent may be 3 to 12, for example, 3, 6, 7, 8, 9, etc., and specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, ethyldimethylsilyl group, triethylsilyl group, etc.

In the present application, the number of carbon atoms of the cycloalkyl group as the substituent may be 3 to 10, for example, 5, 6, 8 or 10, and specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.

In the present application, the number of carbon atoms of the haloalkyl group as a substituent may be 1 to 10. For example, the haloalkyl group may be a fluoroalkyl group having 1 to 5 carbon atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

In a first aspect, the present application provides a nitrogen-containing compound, which has a structure represented by formula 1:

in formula 1, X₁～X₃Are identical or different and are each independently selected from C (H) or N, and X₁～X₃Is N;

L、L₁and L₂The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

In this application, X₁～X₃One, two or three of may be N atoms. In one embodiment, X₁～X₃Two of which are N atoms and the remaining one is C (H), e.g. X₁And X₃Is N, X₂Is C (H); or X₁And X₂Is N, X₃Is C (H); or X₂And X₃Is N, X₁Is C (H). In another embodiment, X₁～X₃Are all N atoms.

Alternatively, Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms. For example, Ar₁And Ar₂May each be independently selected from: a substituted or unsubstituted aryl group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

In a specific embodiment, Ar₁Selected from substituted or unsubstituted aryl group having 10 to 25 carbon atoms, substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms, Ar₂Selected from substituted or unsubstituted aromatic hydrocarbon with 6-20 carbon atomsA substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

Alternatively, Ar₁And Ar₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms; optionally, in Ar₁、Ar₂In (b), any two adjacent substituents form a saturated or unsaturated ring having 5 to 15 carbon atoms. For example, Ar₁And Ar₂Specific examples of the substituent in (1) include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, cyclopentyl, cyclohexyl.

In some embodiments, Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.

Alternatively, Ar₁、Ar₂Wherein the substituents are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, cyclopentyl, cyclohexyl; optionally, Ar₁、Ar₂Wherein any two adjacent substituents form a benzene, cyclopentane, cyclohexane or fluorene ring.

In one embodiment, Ar₁And Ar₂Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups Z selected from the group consisting of:

the substituted group Z has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl and pyridyl, and when the number of the substituents is more than 1, each substituent is the same or different.

Alternatively, Ar₁Selected from the group consisting of:

in a specific embodiment, Ar₁Selected from the group consisting of:

alternatively, Ar₂Selected from the group consisting of:

in a specific embodiment, Ar₂Selected from the group consisting of:

alternatively, L, L₁And L₂The same or different, and each is independently selected from single bond, substituted or unsubstituted subunit with 6-20 carbon atomsAryl, substituted or unsubstituted heteroarylene having 12 to 18 carbon atoms.

Yet alternatively, L, L₁And L₂May each be independently selected from: a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 5, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms.

Alternatively, L, L₁And L₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms. For example, L, L₁And L₂The substituents in (a) may each be independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl.

In some embodiments, L, L₁And L₂The same or different, and each is 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 phenanthrylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group.

Alternatively, L, L₁And L₂Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl.

In one embodiment, L is selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:

the substituted group V has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl; when the number of the substituents is more than 1, the substituents may be the same or different.

Alternatively, L is selected from a single bond or the group consisting of:

further optionally, L is selected from a single bond or the group consisting of:

in one embodiment, L₁And L₂Identical or different and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, L₁And L₂Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, isopropyl, tert-butyl, trifluoromethyl or phenyl.

Alternatively, L₁And L₂The same or different and each is independently selected from the group consisting of a single bond or the following groups:

in one embodiment, L is a single bond,

in Ar₁And L₁Is not less than 10, preferably 10 to 30, for example, Ar₁And L₁Total carbon atom ofThe sub-number is 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.

In a preferred embodiment, Ar₁Is a substituted or unsubstituted group Q, wherein the unsubstituted group Q has the structure shown below:

y is selected from O, S, C (R)_aR_b) N (Ar) or N, R_aAnd R_bEach independently selected from hydrogen, methyl or phenyl; optionally, R_aAnd R_bForm a cyclopentane, cyclohexane or fluorene ring with the C atom to which they are both attached; ar is an aryl group having 6 to 12 carbon atoms, such as phenyl, naphthyl, biphenyl;

the substituted group Q comprises one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl and naphthyl, and when the number of the substituents is more than 1, each substituent is the same or different.

Alternatively, L₁Is a single bond or phenylene.

Alternatively, Ar₁Selected from the group consisting of:

in a preferred embodiment of the present invention,

selected from the group consisting of:

in another particular embodiment of the method of the present invention,

selected from the group consisting of:

optionally, the nitrogen-containing compound is selected from the group consisting of:

the synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present invention illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the present application.

In a second aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer may contain the nitrogen-containing compound of the first aspect.

The nitrogen-containing compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the characteristics of the organic electroluminescent device such as service life and the like.

Optionally, the functional layer comprises an organic light emitting layer comprising a nitrogen containing compound as provided herein.

Alternatively, the organic electroluminescent device may be a green device, a red device, or a blue device.

In a preferred embodiment, the organic electroluminescent device is a red light device.

According to an embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The nitrogen-containing compound provided by the application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device so as to effectively improve the performance of the organic electroluminescent device.

Alternatively, the organic light emitting layer 330 includes a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, the excitons transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light. The host material may comprise a nitrogen-containing compound of the present application.

The guest material of the organic light emitting layer 330 may be selected according to the prior art, and may be selected from, for example, iridium (III) organometallic complex, platinum (II) organometallic complex, and ruthenium (II) complex. Specifically, the guest material may be selected from at least one of the following compounds:

in a specific embodiment, the guest material is RD-1, i.e., Ir (piq)₂(acac)。

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 example package of anode materialComprises the following steps: 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, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.

In the present application, the material of the hole transport layer 320 may be selected from phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine type triarylamine, styrene amine type triarylamine, diamine type triarylamine, or other types of materials, and may be selected by those skilled in the art with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of:

in the present application, the hole transport layer 320 may have a one-layer or two-layer structure. Alternatively, as shown in fig. 1, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, which are stacked, wherein the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322. In a specific embodiment, the first hole transport layer 321 is comprised of HT-8 and the second hole transport layer 322 is comprised of HT-14.

Alternatively, the electron transport layer 340 may be a single layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may generally include a metal complex and/or a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from LiQ, Alq, and the like₃、Bepq₂Etc.; the above-mentionedThe nitrogen-containing heterocyclic derivative may be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, or the like, and specific examples include, but are not limited to, 1, 10-phenanthroline-based compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, or the like, or an anthracene-based compound, triazine-based compound, or pyrimidine-based compound having a nitrogen-containing aryl group of the structure shown below. In a specific embodiment, the electron transport layer 340 comprises LiQ and BimiBphen.

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 a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.

Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be selected from the group consisting of:

in a specific embodiment, the material of the hole injection layer 310 is PPDN.

Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the material of the electron injection layer 350 may be selected from LiF, NaCl, CsF, Li₂O、BaO、LiQ、NaCl、CsF、Cs₂CO₃One or more of Na, Li, Ca, Al and Yb. In a specific embodiment, the material of the electron injection layer 350 may include LiQ or Yb.

In a third aspect, the present application provides an electronic device comprising the above organic electroluminescent device.

As shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 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.

The invention is further illustrated by the following examples, but is not to be construed as being limited thereto.

No mention is made in this application of commercially available starting products of compounds of the synthetic process.

1. Synthesis of intermediate IM I

(1) Introducing nitrogen into a three-neck flask equipped with a mechanical stirrer, a thermometer and a condenser for 10min (2L/min), adding raw material sub a-1(105mmol, 14.69g), raw material sub b-1(100mmol, 23.71g), potassium carbonate (200mmol, 27.60g), toluene (200mL), ethanol (50mL) and water (50mL), and starting stirring; heating to 40-45 ℃, adding dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.1mmol, 0.07g), continuously heating to 60-65 ℃ and reacting for 2 hours. Cooling the reaction liquid to 25 ℃, separating liquid, adding toluene (50mL) into the water phase for extraction, combining organic phases, washing for 2 times, drying the obtained organic phase by using anhydrous sodium sulfate, filtering, concentrating the organic phase to dryness under negative pressure, adding ethanol (50mL), filtering, and drying to obtain an intermediate IM I-1(23.21g, yield 92.0%).

(2) Introducing nitrogen into a three-neck flask with a mechanical stirring device, a thermometer and a condenser for 10min (2L/min), adding an intermediate IM I-1(90mmol,22.7g) and THF (160mL), starting stirring, cooling to-25 to-20 ℃, dropwise adding n-hexane solution (108mmol, 54mL) of n-butyllithium, preserving heat for 2h after dropwise adding, dropwise adding 1, 2-dibromoethane (108mmol, 20.29g), and preserving heat for 2h after dropwise adding. Water (100mL) and dichloromethane (100mL) were added, the layers were separated, the aqueous layer was extracted with 50mL more dichloromethane, the organic phases were combined, washed 2 times with water, dried over anhydrous sodium sulfate, filtered, the organic phase was concentrated to dryness, recrystallized from ethanol (100mL), and dried to afford intermediate IM I-2(23.18g, 77.8% yield).

(3) After introducing nitrogen gas into a three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser for 10min (2L/min), IM I-2(60mmol, 19.87g) and methylene chloride (100mL) were sequentially added, and stirring was started. Cooling to-5-0 ℃, dropwise adding boron tribromide (90mmol, 22.55g), preserving heat for 3h after dropwise adding, adding water (100mL), separating, sequentially washing with water for 2 times, adding anhydrous sodium sulfate into the organic phase, drying, filtering, and concentrating the organic phase to dryness to obtain an intermediate IM I-3(18.39g, yield 96.6%).

(4) After introducing nitrogen gas into a three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser for 10min (2L/min), IM I-3(50mmol, 15.86g), DMF (90mL) and cesium carbonate (100mmol, 32.58g) were added in this order, and stirring was turned on. And (3) heating to 90-100 ℃, preserving the temperature for 5h, adding water (100mL) and dichloromethane (100mL), separating the solution, extracting the water phase with dichloromethane (50mL), combining the organic phases, continuously washing the organic phases for 2 times, adding anhydrous sodium sulfate into the organic phases, drying, filtering, concentrating the organic phases to dryness, adding petroleum ether (100mL), recrystallizing, and drying to obtain an intermediate IM I-4(13.37g, yield 90%).

(5) After introducing nitrogen gas into a three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser for 10min (2L/min), IM I-4(40mmol, 11.88g), a raw material sub c-1(42mmol, 5.36g), sodium tert-butoxide (80mmol, 7.68g), Pd were added in this order₂(dba)₃(0.4mmol, 0.37g), x-phos (1mmol, 0.48g) and toluene (80mL), stirring was turned on. And (3) continuing replacing for 2 times by using nitrogen, heating to 90-100 ℃, preserving heat for 2 hours, adding water (50mL), separating, extracting a water phase by using toluene (50mL), combining organic phases, continuing washing for 2 times, adding anhydrous sodium sulfate into the organic phase, filtering, concentrating the organic phase to the residual 30mL, cooling to room temperature, filtering, and drying to obtain an intermediate IM I-5(11.00g, yield 80%).

(6) After introducing nitrogen gas into a three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser for 10min (2L/min), IM I-5(30mmol, 10.31g), cesium carbonate (60mmol, 19.55g), tricyclohexylphosphine tetrafluoroborate (3mmol, 1.11g), palladium acetate (1.5mmol, 0.34g) and N, N-dimethylacetamide (80mL) were added in this order, and the stirring was turned on. Heating to 130-140 ℃, preserving heat for 10h, adding water (400mL), filtering, passing the solid through a heat preservation column at 80-90 ℃ by using n-heptane, concentrating the column passing liquid to the residual 50mL, cooling to room temperature, filtering, and drying to obtain an intermediate IM I (5.07g, yield 55%).

2. Synthesis of Compounds

Synthesis example 1: synthesis of Compound 4

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, sequentially adding raw material sub d-1(11mmol, 3.78g), intermediate IM I (10mmol, 3.07g) and DMF (30mL), starting stirring, adding NaH (12mmol, 2.88g) in portions at room temperature, and continuing to react for 4h after the addition is finished. Water (20mL) and dichloromethane (30mL) were added, the layers were separated, and the aqueous layer was extracted with dichloromethane (20mL) 1 time. The combined organic phases were washed 2 times with water, dried over anhydrous sodium sulfate, filtered, concentrated to dryness, recrystallized by addition of toluene (10mL), filtered and dried to give compound 4(5.23g, 85% yield) M/z as 615.2[ M + H ] ms spectrum]⁺(ii) a Nuclear magnetic data:¹H NMR(CDCl₃,400MHz):δppm 8.55(d,1H),8.43-8.39(m,3H),8.26(d,1H),8.17(d,1H),8.01(d,1H),7.92(s,1H),7.83-7.78(m,4H),7.62-7.58(m,3H),7.53-7.47(m,7H),7.36(s,1H),7.28-7.24(m,3H)。

synthesis examples 2 to 20

The compounds listed in table 1 were synthesized by the method of reference compound 4 except that the sub d-1 was replaced by the raw material a shown in table 1, and the synthesized compounds and the yields and mass spectrum characterization results thereof are shown in table 1.

TABLE 1

3. Synthesis of intermediate IM-AX

The synthesis of intermediate IM-AX is illustrated by taking intermediate IM-A1 as an example:

introducing nitrogen into a three-neck flask with a mechanical stirring device, a thermometer and a condenser for 10min (2L/min), adding a raw material sub e-1(20mmol, 6.88g), a raw material sub f-1(21mmol, 3.29g), potassium carbonate (60mmol, 8.28g), toluene (60mL), ethanol (20mL) and water (20mL), starting stirring, heating to 40-45 ℃, adding tetrakis (triphenylphosphine) palladium (0.2mmol,0.23g), and continuously heating to 60-65 ℃ for reaction for 8 h. The reaction solution was cooled to 25 ℃, filtered and dried to obtain intermediate IM-A1(7.14g, yield 85.2%).

Other IM-AXs were synthesized according to the method of IM-A1, except that sub e-1 was replaced by raw material B and sub f-1 was replaced by raw material C, and the main raw materials used, the intermediates synthesized and the yields thereof were as shown in Table 2.

TABLE 2

4. Synthesis of Compounds

Synthesis example 21: synthesis of Compound 133

To a ball shape equipped with a mechanical stirring, thermometerIntroducing nitrogen (0.100L/min) into a three-neck flask of a condenser tube for replacement for 15min, sequentially adding IM-A1(11mmol, 4.62g), IM I (10mmol, 3.07g), potassium carbonate (20mmol, 2.76g), cuprous chloride (5mmol, 0.5g) and DMF (40mL), starting stirring, heating to 130-135 ℃, and carrying out heat preservation reaction for 12 h. Water (20mL) and dichloromethane (30mL) were added, the layers were separated, and the aqueous layer was extracted with dichloromethane (20mL) 1 time. The combined organic phases were washed 2 times with water, dried over anhydrous sodium sulfate, passed through a silica gel column, the organic phase was concentrated to dryness, and recrystallized by adding toluene (15mL), filtered, and dried to obtain compound 133(5.45g, yield 79%), ms spectrum: 691.2[ M + H ] M/z]⁺。

Synthesis examples 22 to 40

The compounds listed in Table 3 were synthesized by referring to the method for synthesizing Compound 133, except that IM-A1 was replaced by the starting material D shown in Table 3, and the synthesized compounds and the yields and mass spectrum characterization structures thereof are shown in Table 3.

TABLE 3

In addition, the nuclear magnetic data for compound 166 is:¹H NMR(CDCl₃,400MHz):δppm 8.53(d,1H),8.27(s,1H),8.23(dd,2H),8.12(d,1H),8.03-7.99(m,4H),7.87-7.81(m,6H),7.78-7.73(m,5H),7.68-7.59(m,5H),7.38(s,1H),7.27-7.19(m,6H)。

organic electroluminescent device production and evaluation examples

Preparation of red organic electroluminescent device

Example 1

An organic electroluminescent device was prepared by the following procedure: the thickness of ITO is set as

The substrate was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, and subjected to uv ozone and O₂:N₂And performing surface treatment by using plasma to increase the work function of the anode, and cleaning the surface of the ITO substrate by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

PPDN was vacuum deposited on the test substrate (anode) to a thickness of

And HT-8 is vacuum-evaporated on the Hole Injection Layer (HIL) to form a layer having a thickness of

A first hole transport layer (HTL 1).

HT-14 is evaporated on the first hole transport layer (HTL1) to a thickness of

And a second hole transport layer (HTL 2).

On the second hole transport layer, compound 4 as a host material was simultaneously doped with Ir (piq) at a film thickness ratio of 100:3₂(acac) to a thickness of

The organic light emitting layer (EML).

Mixing BimiBphen and LiQ at a weight ratio of 1: 1, and evaporating on an organic light emitting layer (EML) to form

A thick Electron Transport Layer (ETL). Evaporating LiQ on the electronic transmissionOn the transfer layer to form a thickness of

Electron Injection Layer (EIL).

Mixing magnesium (Mg) and silver (Ag) at a ratio of 1: 9, vacuum evaporating to form a mixture with a thickness of

The cathode of (1). The thickness of the vapor deposition on the cathode is set to

Forming a capping layer (CPL), thereby completing the fabrication of the organic light emitting device.

Example 2 example 40

Organic electroluminescent devices were produced in the same manner as in example 1, except that the compounds shown in table 4 were used as host materials instead of the compound 4, respectively, in forming the organic light-emitting layers.

Comparative example 1 to comparative example 4

An organic electroluminescent device was produced in the same manner as in example 1, except that compound a, compound B, compound C, and compound D were used as host materials instead of compound 4, respectively, in forming an organic light-emitting layer.

In examples and comparative examples, the structural formula of the main material for preparing the organic electroluminescent device is as follows:

the organic electroluminescent devices prepared in examples and comparative examples were subjected to a performance test at 10mA/cm²The IVL performance of the device was analyzed at 15mA/cm²The devices were analyzed for T95 lifetime with the test results shown in table 4.

TABLE 4

It is understood from the results of table 4 that the organic electroluminescent devices prepared in examples 1 to 40 using the nitrogen-containing compounds of the present application as light-emitting host materials have longer device life and higher light-emitting efficiency than those prepared in comparative examples 1 to 4 using compounds a to D as light-emitting host materials, respectively, while maintaining a lower device driving voltage, and specifically, the devices prepared in examples 1 to 40 have a longer device life of at least 11.1% and a higher current efficiency of at least 13.2% than those prepared in comparative examples 1 to 4. In addition, as can be seen from examples 1 to 40, when the substituent on the triazine group in the structure of the compound of the present application includes a dibenzo five-membered ring structure, the organic electroluminescent device produced has a longer lifetime.

The preferred embodiments of the present invention have been described in detail with reference to the accompanying drawings, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention. It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition. In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present disclosure.

Claims

1. A nitrogen-containing compound is characterized in that the structure of the nitrogen-containing compound is shown as formula 1:

2. The nitrogen-containing compound according to claim 1, wherein Ar is Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms, substituted or unsubstituted heteroaryl with 5-20 carbon atoms;

preferably, Ar₁And Ar₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms; optionally, in Ar₁、Ar₂In, any twoThe adjacent substituents form a saturated or unsaturated ring having 5 to 15 carbon atoms.

3. The nitrogen-containing compound according to claim 1, wherein Ar is Ar₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;

preferably, Ar₁、Ar₂Wherein the substituents are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, cyclopentyl, cyclohexyl; optionally, Ar₁、Ar₂Wherein any two adjacent substituents form a benzene, cyclopentane, cyclohexane or fluorene ring.

4. The nitrogen-containing compound according to claim 1, wherein Ar is Ar₁And Ar₂Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups Z selected from the group consisting of:

5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar₁Selected from the group consisting of:

preferably, Ar₂Selected from the group consisting of:

6. the nitrogen-containing compound according to claim 1, wherein L, L₁And L₂The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms;

preferably L, L₁And L₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms.

7. The nitrogen-containing compound according to claim 1, wherein L, L₁And L₂The same or different, and each is independently selected from the group consisting of 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 phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group;

preferably L, L₁And L₂Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl.

8. The nitrogen-containing compound of claim 1, wherein L is selected from the group consisting of a single bond, a substituted or unsubstituted group V, and an unsubstituted group V is selected from the group consisting of:

the substituted group V has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl; when the number of the substituent groups is more than 1, all the substituent groups are the same or different;

preferably, L₁And L₂Identical or different and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, L₁And L₂Each substituent in (a) is independently selected from deuterium, fluoro, cyano, methyl, isopropyl, tert-butyl, trifluoromethyl or phenyl.

9. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:

10. an organic electroluminescent device, comprising an anode and a cathode which are oppositely arranged, and a functional layer which is arranged between the anode and the cathode; the functional layer contains the nitrogen-containing compound according to any one of claims 1 to 9.

11. The organic electroluminescent device according to claim 10, wherein the functional layer comprises an organic light-emitting layer containing the nitrogen-containing compound.

12. An electronic device comprising the organic electroluminescent device according to claim 10 or 11.