Nitrogen-containing compound and organic electroluminescent device and electronic device using the same

Abstract

The present application belongs to the field of organic electroluminescence technology, and relates to a nitrogen-containing compound and an organic electroluminescent device and an electronic device using the same. The structure of the nitrogen-containing compound is shown in Formula 1. When the nitrogen-containing compound is used in an organic electroluminescent device, the device performance can be significantly improved.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to a nitrogen-containing compound and an organic electroluminescent device and an electronic device using the same. Background Art

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

[0003] The purpose of the present application is to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device using the same, which have high luminous efficiency and service life.

[0004] In order to achieve the above-mentioned object, the first aspect of the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:

[0005]

[0006] wherein Ring A and Ring B are independently selected from aromatic rings having 6 to 12 carbon atoms;

[0007] Ar1, Ar2 and Ar3 are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;

[0008] L, L1, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;

[0009] R a and R b are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;

[0010] na Represents R a The number of n b Represents R b The number of n a and n b are independently selected from 0, 1, 2, 3, 4, 5 or 6;

[0011] The substituents in Ar1, Ar2, Ar3, L, L1, L2 and L3 are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms.

[0012] In a second aspect, the present application provides an organic electroluminescent device comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.

[0013] A third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect of the present application.

[0014] This application provides a nitrogen-containing compound with a core structure composed of triazine, benzoxazole, and carbazole groups with a specific connection pattern. This specific connection pattern results in a high degree of structural distortion and high electron transport efficiency. Using the nitrogen-containing compound as a host material (particularly an electronic host) in the organic light-emitting layer of an organic electroluminescent device can significantly improve the efficiency and lifespan of the organic electroluminescent device.

[0015] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] The accompanying drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following detailed description, they are used to explain the present application but do not constitute a limitation of the present application. In the accompanying drawings:

[0017] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0018] Figure 2 It is a schematic structural diagram of an electronic device according to one embodiment of the present application.

[0019] Description of Reference Numerals

[0020] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, hole auxiliary layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 400, electronic device. DETAILED DESCRIPTION

[0021] The following describes the specific embodiments of the present application in detail with reference to the accompanying drawings. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present application and are not intended to limit the present application.

[0022] In a first aspect, the present application provides a nitrogen-containing compound having a structure shown in Formula 1 below:

[0023]

[0024] wherein Ring A and Ring B are independently selected from aromatic rings having 6 to 12 carbon atoms;

[0025] Ar1, Ar2 and Ar3 are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;

[0026] L, L1, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms;

[0027] R a and R b are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms;

[0028] n a Represents R a The number of n b Represents R b The number of n a and n b are independently selected from 0, 1, 2, 3, 4, 5 or 6;

[0029] The substituents in Ar1, Ar2, Ar3, L, L1, L2 and L3 are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms.

[0030] In this application, the number of carbon atoms in Ring A, Ring B, Ar1, Ar2, Ar3, L, L1, L2, and L3 refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene group having 10 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 10. For example, if Ar1 is 9,9-dimethylfluorenyl, then Ar1 is a substituted fluorenyl group having 15 carbon atoms, and Ar1 has 13 ring carbon atoms.

[0031] In this application, the expressions "a substituted or unsubstituted aryl group having 6 to 30 carbon atoms" and "a substituted or unsubstituted aryl group having 6 to 30 carbon atoms" have the same meaning, both referring to an aryl group and its substituents having a total carbon number of 6 to 30. Similarly, in this specification, the expressions "a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms" and "a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms" have the same meaning, both referring to a heteroaryl group and its substituents having a total carbon number of 5 to 30.

[0032] The description methods used in this application, "each...is independently" and "...are independently" and "...are independently selected from" can be interchanged and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or that in the same group, the specific options expressed by the same symbols do not affect each other.

[0033] For example: In " Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from the description of hydrogen, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.

[0034] In the present application, when no specific definition is provided otherwise, "hetero" means that a functional group includes at least one heteroatom such as B, N, O, S, Se, Si or P and the remaining atoms are carbon and hydrogen.

[0035] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent. For example, "substituted or unsubstituted aryl" refers to an alkyl group or an unsubstituted aryl group with a substituent. "Substituted" means that it may be substituted by a substituent selected from the following groups: deuterium, a halogen group, a cyano group, a heteroaryl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms.

[0036] In this application, "alkyl" can include straight-chain alkyl or branched-chain alkyl. Alkyl groups can have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to each integer in the given range; for example, "1 to 10 carbon atoms" refers to alkyl groups that can 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, or 10 carbon atoms. The alkyl group can be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH3), ethyl (Et, -CH2CH3), n-propyl (n-Pr, -CH2CH2CH3), isopropyl (i-Pr, -CH(CH3)2), n-butyl (n-Bu, -CH2CH2CH2CH3), isobutyl (i-Bu, -CH2CH(CH3)2), sec-butyl (s-Bu, -CH(CH3)CH2CH3), tert-butyl (t-Bu, -C(CH3)3), etc. In addition, the alkyl group can be substituted or unsubstituted.

[0037] In this application, a cycloalkyl group refers to a cyclic saturated hydrocarbon, including monocyclic and polycyclic structures. A cycloalkyl group may have 3 to 10 carbon atoms. For example, "3 to 10 carbon atoms" refers to a cycloalkyl group containing 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. Examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0038] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon conjugation, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon conjugation, or two or more condensed ring aryl groups connected by carbon-carbon conjugation. That is, two or more aromatic groups connected by carbon-carbon conjugation can also be regarded as aryl groups in the present application. Among them, the aryl group does not contain heteroatoms such as B, N, O, S, Se, Si or P. For example, in the present application, phenyl, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups can include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaternaryl, benzo[9,10]phenanthrenyl, pyrenyl, perylenyl, benzofluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, indenyl and the like, but are not limited thereto.

[0039] The "substituted or unsubstituted aryl group" herein may contain 6 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 25. In other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 20. In the present application, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.

[0040] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, I, CN, a hydroxyl group, a branched alkyl group, a straight-chain alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, or other groups. 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 with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents on the aryl group is 18. For example, 9,9-dimethylfluorenyl is a substituted aryl group with 15 carbon atoms. In this application, specific examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl.

[0041] In the present application, the fluorenyl group as an aromatic group may be substituted, and two substituents may be combined with each other to form a spiro structure. Specific examples include but are not limited to the following structures:

[0042]

[0043] In the present application, the heteroaryl group may be a heteroaryl group including 1, 2, 3, 4, 5 or 6 heteroatoms selected from B, O, N, P, Si, Se and S. 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 conjugation of carbon-carbon bonds, any of which is an aromatic monocyclic ring or an aromatic fused ring, and any of which contains the heteroatoms. For example, the heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzothiophenyl, dibenzofuranyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, etc., without limitation thereto.

[0044] The "substituted or unsubstituted heteroaryl group" herein may contain 5 to 30 carbon atoms. In some embodiments, the substituted or unsubstituted heteroaryl group is a heteroaryl group having 5 to 20 carbon atoms. In other embodiments, the substituted or unsubstituted heteroaryl group is a heteroaryl group having 5 to 20 carbon atoms. In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.

[0045] In this application, a substituted heteroaryl group refers to a heteroaryl group in which one or more hydrogen atoms are replaced by a group thereof, for example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, -CN, an alkyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, a silanyl group, a phosphinoyl group, or other groups. In this application, specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, quinolyl, isoquinolyl, or phenanthroline.

[0046] In the present application, the explanations for aryl group may be applied to arylene group, the explanations for heteroaryl group may be applied to heteroarylene group, the explanations for alkyl group may be applied to alkylene group, and the explanations for cycloalkyl group may be applied to cycloalkylene group.

[0047] The non-positioned connecting bond in this application refers to a single bond extending from the ring system It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

[0048] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0049]

[0050] For another example, as shown in the following formula (X'), the phenanthryl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0051]

[0052] A non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring by a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7).

[0053]

[0054] The meanings of non-positional connection or non-positional substitution in the following text are the same as those herein and will not be further described.

[0055] In the present application, the carbon number of the haloalkyl group having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, including but not limited to trifluoromethyl and the like.

[0056] In the present application, the alkoxy group having 1 to 10 carbon atoms may be a chain, a cyclic or a branched alkoxy group, and may have 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, including but not limited to methoxy and isopropoxy.

[0057] In the present application, the alkylthio group having 1 to 10 carbon atoms may be a chain, cyclic or branched alkylthio group, and may have 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.

[0058] In the present application, the trialkylsilyl group has 3 to 12 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms, including but not limited to trimethylsilyl and the like.

[0059] In the present application, the halogen group may be selected from fluorine, chlorine, bromine, and iodine.

[0060] In some embodiments of the present application, the nitrogen-containing compound has a structure shown in any one of Formulas 1-1 to 1-6:

[0061]

[0062] In some embodiments of the present application, Ra and R b are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0063] In some embodiments of the present application, n a and n b Both are 0.

[0064] In some embodiments of the present application, Ring A and Ring B are each independently selected from an aromatic ring having 6 to 10 carbon atoms.

[0065] In some embodiments of the present application, ring A and ring B are independently selected from a benzene ring or a naphthalene ring.

[0066] In some embodiments of the present application, Ar1 and Ar2 are independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

[0067] Optionally, the substituents in Ar1 and Ar2 are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0068] In some embodiments of the present application, Ar1 and Ar2 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl.

[0069] Optionally, the substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0070] In some embodiments of the present application, Ar1 and Ar2 are independently selected from a substituted or unsubstituted group V1, and the unsubstituted group V1 is selected from the group consisting of the following groups:

[0071]

[0072] in, represents a chemical bond; the substituted group V1 contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl; when the substituted group V1 contains multiple substituents, the substituents are the same or different.

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

[0074]

[0075] In some embodiments of the present application, Ar3 is phenyl.

[0076] In some embodiments of the present application, L, L1, L2 and L3 are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0077] Optionally, the substituents in L, L1, L2 and L3 are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0078] Optionally, L and L3 are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.

[0079] Optionally, the substituents in L and L3 are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0080] In some embodiments of the present application, L and L3 are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenylene group.

[0081] Optionally, the substituents in L and L3 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0082] In some embodiments of the present application, L and L3 are independently selected from a single bond, a substituted or unsubstituted group V2, and the unsubstituted group V2 is selected from the group consisting of the following groups:

[0083]

[0084] in, represents a chemical bond; the substituted group V2 contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; when the substituted group V2 contains multiple substituents, the substituents are the same or different.

[0085] Optionally, L and L3 are independently selected from a single bond or the group consisting of the following groups:

[0086]

[0087] In some embodiments of the present application, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0088] Optionally, the substituents in L1 and L2 are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0089] In other embodiments of the present application, L1 and L2 are 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.

[0090] Optionally, the substituents in L1 and L2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0091] Optionally, L1 and L2 are independently selected from a single bond or the following groups:

[0092]

[0093]

[0094] In some specific embodiments of the present application, in Formula 1, Selected from the group consisting of:

[0095]

[0096] Optionally, in Formula 1, Selected from the group consisting of:

[0097]

[0098]

[0099] In some specific embodiments of this application, are independently selected from the group consisting of:

[0100]

[0101] Optionally, are independently selected from the group consisting of:

[0102]

[0103] In some specific embodiments of the present application, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In a second aspect, 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; the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.

[0135] For example, if Figure 1 As shown, the organic electroluminescent device may include an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 contains the nitrogen-containing compound described in the first aspect of the present application.

[0136] In a specific embodiment of the present application, the organic electroluminescent device may be, for example, a green organic electroluminescent device or a red organic electroluminescent device.

[0137] In some specific embodiments of the present application, the functional layer 300 includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound.

[0138] In some specific embodiments of the present application, the organic electroluminescent device may include an anode 100 , a hole transport layer 321 , a hole auxiliary layer 322 , an organic light emitting layer 330 , an electron transport layer 340 and a cathode 200 , which are sequentially stacked.

[0139] In a specific embodiment of the present application, the anode 100 includes the following anode materials, preferably materials with a large work function that facilitates hole injection into the functional layer. The anode materials specifically include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. At the same time, preferably, a transparent electrode containing indium tin oxide (ITO) as the anode is included.

[0140] In some specific embodiments of the present application, the hole transport layer 321 and the hole auxiliary layer 322 may include one or more hole transport materials. The hole transport layer materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. Specifically, the hole transport layer 321 is composed of the compound NPB.

[0141] In some specific embodiments of the present application, the hole assisting layer 322 may be composed of a compound TAPC, or a compound TPD.

[0142] In the present application, 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, wherein the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not make any special restrictions on this. For example, in one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0143] In some specific embodiments of the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material or may be composed of a host material and a guest material. Preferably, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0144] The host material of the organic light-emitting layer 330 can be the nitrogen-containing compound of the present application, or can be composed of the nitrogen-containing compound of the present application and other light-emitting host materials, such as metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. This application does not impose any specific restrictions on this. In one specific embodiment, the host material of the organic light-emitting layer 330 is composed of the nitrogen-containing compound of the present application and compound GH(p), or the nitrogen-containing compound of the present application and compound RH(p).

[0145] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not impose any particular restrictions on this. In one specific embodiment of this application, the guest material of the organic light-emitting layer 330 is the compound Ir(3mppy)3 or the compound Ir(btp)2(acac).

[0146] In some embodiments of the present application, cathode 200 includes a cathode material having a low work function that facilitates electron injection into the functional layer. Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer materials such as, but not limited to, LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode containing silver and magnesium is used as the cathode.

[0147] In this application, if Figure 1 As shown, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitations thereon. In one embodiment of the present application, the hole injection layer 310 may be composed of the compound HATNA.

[0148] In some specific embodiments of this application, Figure 1 As shown, an electron injection layer 350 may be provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include 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 matter. Specifically, the electron injection layer 350 may include Yb.

[0149] The third aspect of the present application provides an electronic device, which includes the organic electroluminescent device provided in the second aspect of the present application. Since the electronic device includes any of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, it has the same beneficial effects, and this application will not repeat them here.

[0150] For example, if Figure 2 As shown, one embodiment of the present application provides an electronic device 400. The electronic device 400 includes the organic electroluminescent device described in the above embodiments. Any organic electroluminescent device described in the embodiments can be used. The electronic device 400 can be a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.

[0151] The present application is further described below by way of examples, but the present application is not limited thereto.

[0152] The present application does not particularly limit the synthesis method of the nitrogen-containing compounds provided. Those skilled in the art can determine a suitable synthesis method based on the nitrogen-containing compounds of this application in combination with the preparation methods provided in the preparation examples. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not interpret this as a limitation of this application.

[0153] Preparation of compounds

[0154] Synthesis of intermediate IM-A-1

[0155]

[0156] To a 500 mL three-necked flask equipped with a nitrogen atmosphere and a reflux system, add sub-1 (15.43 g, 50 mmol), p-bromophenylboronic acid (11.05 g, 55 mmol), potassium carbonate (13.82 g, 100 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), toluene (120 mL), ethanol (30 mL), and ultrapure water (30 mL). Heat and stir the mixture. When the temperature reaches 40°C, add tetrakis(triphenylphosphine)palladium (0.58 g, 1 mmol). The mixture is heated and refluxed for 30 h. After the reaction is complete, the reaction mixture is cooled to room temperature, separated, and the aqueous phase is extracted with 200 mL of toluene. The organic phases are combined, washed with ultrapure water (200 mL x 3), and then dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (volume ratio 3:1) as eluent to obtain intermediate IM-A-1 (7.7 g, yield 40%).

[0157] Synthesis of intermediate IM-AX

[0158] Intermediate IM-AX was synthesized by referring to the synthesis method of intermediate IM-A-1, except that raw material 1 was used instead of sub-1, and raw material 2 was used instead of p-bromophenylboronic acid. The structure and yield of intermediate IM-AX are listed in Table 1.

[0159] Table 1

[0160]

[0161]

[0162]

[0163] Synthesis of intermediate IM-B-1

[0164]

[0165] In a 500 mL three-necked flask equipped with a nitrogen atmosphere and a reflux system, sub-2 (14.53 g, 55 mmol), carbazole (8.36 g, 50 mmol), and xylene (180 mL) were added and heated with stirring. The mixture was then brought to reflux and stirred for half an hour. The reaction system was cooled to 80°C, and sodium tert-butoxide (7.21 g, 75 mmol), tris(dibenzylideneacetone)dipalladium (458 mg, 0.5 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g, 1 mmol) were added. The mixture was then brought to reflux and allowed to react for 5 hours. After the reaction, the system was cooled to room temperature and the reaction solution was extracted three times with toluene. The organic phases were combined, washed once with water, and dried over anhydrous sodium sulfate for 0.5 hours. The organic phase was concentrated under reduced pressure, and the resulting residue was dry-mixed and the product was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (2:1 by volume) as the eluent to obtain intermediate IM-B-1 (5.53 g, 28% yield).

[0166] Synthesis of intermediate IM-BX

[0167] The intermediate IM-BX was synthesized by silica gel column chromatography according to the synthesis method of intermediate IM-B-1, except that raw material 3 was used instead of 6,7-dichloro-2-phenylbenzoxazole. The structure and yield of intermediate IM-BX are listed in Table 2.

[0168] Table 2

[0169]

[0170]

[0171]

[0172]

[0173] Synthesis of intermediate IM-b-1

[0174]

[0175] To a 500 mL three-necked flask equipped with a nitrogen atmosphere and a reflux system, sub-3 (14.53 g, 55 mmol), sub A (12.55 g, 57.77 mmol), and xylene (180 mL) were added. The mixture was heated with stirring, and the temperature was raised to reflux with stirring for half an hour. The system was cooled to 80°C, and sodium tert-butoxide (7.93 g, 82.52 mmol), tris(dibenzylideneacetone)dipalladium (0.50 g, 0.55 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.45 g, 1.10 mmol) were added, followed by reflux for 4 hours. After the reaction, the system was cooled to room temperature, and the reaction solution was extracted three times with toluene. The organic phases were combined, washed three times with water, and dried over anhydrous sodium sulfate for 0.5 hour. The organic phase was concentrated under reduced pressure, and the resulting residue was dry-mixed and the product was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (volume ratio 3:1) as the eluent to obtain intermediate IM-b-1 (6.12 g, yield 25%).

[0176] Synthesis of intermediate IM-bX

[0177] Intermediate IM-bX was synthesized by referring to the synthesis method of intermediate IM-b-1, except that raw material 4 was used instead of 6,7-dichloro-2-phenylbenzoxazole, and raw material 5 was used instead of sub A. The structure and yield of intermediate IM-bX are listed in Table 3.

[0178] Table 3

[0179]

[0180]

[0181]

[0182] Synthesis of intermediate IM-C-1

[0183]

[0184] To a 1L three-necked flask equipped with a nitrogen atmosphere and a reflux system, add sub B (34.77g, 110mmol), phenylboric acid (12.19g, 100mmol), sodium carbonate (21.2g, 200mmol), tetrabutylammonium bromide (3.22g, 10mmol), toluene (300mL), and ultrapure water (60mL). Heat with stirring. When the temperature reaches 40°C, add tetrakis(triphenylphosphine)palladium (1.15g, 1mmol). The mixture is heated and refluxed for 2h. After the reaction is complete, the reaction mixture is cooled to room temperature and separated. The aqueous phase is extracted with 200mL of toluene. The organic phases are combined, washed with ultrapure water (200mL x 3), and then dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (volume ratio of 3:1) as eluent to obtain intermediate IM-C-1 (19.68 g, yield 55%).

[0185] Synthesis of intermediate IM-CX

[0186] Intermediate IM-CX was synthesized by referring to the synthesis method of intermediate IM-C-1, except that raw material 6 was used instead of subB, and raw material 7 was used instead of phenylboronic acid. The structure and yield of intermediate IM-CX are listed in Table 4.

[0187] Table 4

[0188]

[0189]

[0190]

[0191] Synthesis of intermediate IM-D-1

[0192]

[0193] In a three-necked flask (1 L) with nitrogen protection and condensation reflux device, intermediate IM-B-1 (9.87 g, 25 mmol), pinacol diboron (7.62 g, 30 mmol), potassium acetate (4.91 g, 50 mmol), and 1,4-dioxane (110 mL) were added. Nitrogen protection was passed through, heating and stirring were turned on, and when the temperature rose to 40°C, tris(dibenzylideneacetone)dipalladium (0.23 g, 0.25 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos, CAS No.: 564483-18-7) (0.24 g, 0.5 mmol) were added, and the temperature was raised to reflux and the reaction was continued for 10 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and 200 mL of water and 200 mL of toluene were added for separation. The aqueous phase was extracted with 200 mL of toluene. The organic phases were combined, washed with ultrapure water (200 mL x 3), and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure, and the resulting residue was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (1:1 by volume) as the eluent to obtain intermediate IM-D-1 (9.73 g, 80% yield).

[0194] Synthesis of intermediate IM-DX

[0195] Intermediate IM-DX was synthesized by referring to the synthesis method of intermediate IM-D-1, except that raw material 8 was used instead of intermediate IM-B-1. The structure and yield of intermediate IM-DX are listed in Table 5.

[0196] Table 5

[0197]

[0198]

[0199]

[0200]

[0201] Synthesis of intermediate IM-d-1

[0202]

[0203] In a three-necked flask (1 L) equipped with nitrogen protection and a condensing reflux device, intermediate IM-b-1 (6 g, 13.48 mmol), pinacol diboron (4.11 g, 16.18 mmol), potassium acetate (2.65 g, 26.97 mmol), and 1,4-dioxane (72 mL) were added, heated and stirred, and when the temperature rose to 40°C, tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos, CAS No.: 564483-18-7) (0.13 g, 0.26 mmol) were added, the temperature was raised to reflux, and the reaction was continued for 6 h. After the reaction is completed, the reaction solution is cooled to room temperature, 200 mL of water and 200 mL of dichloromethane are added for separation, the aqueous phase is extracted with 200 mL of dichloromethane, the organic phases are combined, the organic phases are washed with ultrapure water (200 mL × 3), and the organic phase is dried over anhydrous sodium sulfate; the product is separated by silica gel column chromatography, the eluent is a mixture of n-heptane and dichloromethane (volume ratio of 1:1), to obtain intermediate IM-d-1 (5.64 g, yield 78%).

[0204] Synthesis of intermediate IM-dX

[0205] Intermediate IM-dX was synthesized by referring to the synthesis method of intermediate IM-d-1, except that raw material 9 was used instead of intermediate IM-b-1. The structure and yield of intermediate IM-dX are listed in Table 6.

[0206] Table 6

[0207]

[0208]

[0209] Synthesis of compound 1

[0210]

[0211] To a 100 mL three-necked flask equipped with nitrogen and reflux was added intermediate IM-D-1 (4.86 g, 10 mmol), sub C (3.48 g, 13 mmol), sodium carbonate (2.12 g, 20 mmol), tetrabutylammonium bromide (322 mg, 1 mmol), toluene (30 mL), and ultrapure water (8 mL). The mixture was heated and stirred. When the temperature reached 40°C, tetrakis(triphenylphosphine)palladium (115 mg, 0.1 mmol) was added. The temperature was raised to reflux and the reaction was allowed to proceed for 2 h. After the reaction was complete, the reaction mixture was cooled to room temperature and separated. The aqueous phase was extracted with 200 mL of toluene. The organic phases were combined, washed with ultrapure water (200 mL x 3), and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (volume ratio 3:1) as eluent to obtain compound 1 (3.85 g, yield 65%).

[0212] Synthesis of Compound X

[0213] Compound X was synthesized by referring to the synthesis method of compound 1, except that raw material A was used instead of intermediate IM-D-1, and raw material B was used instead of sub C (2-chloro-4,6-diphenyl-1,3,5-triazine). The structure, yield and mass spectrometry data of compound X are listed in Table 7.

[0214] Table 7

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] Synthesis of compound 545

[0223] To a 100 mL three-necked flask equipped with nitrogen and reflux was added intermediate IM-d-1 (7.86 g, 14.65 mmol), sub C (4.32 g, 16.12 mmol), sodium carbonate (3.10 g, 29.31 mmol), tetrabutylammonium bromide (0.47 g, 1.47 mmol), toluene (48 mL), and ultrapure water (12 mL). The mixture was heated with stirring. When the temperature reached 40°C, tetrakis(triphenylphosphine)palladium (0.17 g, 0.15 mmol) was added, and the temperature was raised to reflux for 2 h. After the reaction was complete, the reaction mixture was cooled to room temperature and separated. The aqueous phase was extracted with 200 mL of toluene. The organic phases were combined, washed with ultrapure water (200 mL x 3), and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography using a mixture of n-heptane and dichloromethane (volume ratio 3:1) as eluent to obtain compound 545 (5.27 g, yield 56%).

[0224] Synthesis of compound Y

[0225] Compound Y was synthesized by referring to the synthesis method of compound 545, except that raw material C was used instead of intermediate IM-d-1, and raw material D was used instead of sub C. The structure, yield and mass spectrometry data of compound Y are listed in Table 8.

[0226] Table 8

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] The NMR data of some compounds are listed in Table 9.

[0233] Table 9

[0234]

[0235] Example 1 Green organic electroluminescent device

[0236] The ITO thickness is The substrate (made by Corning) was cut into the size of 40mm×40mm×0.7mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was treated using ultraviolet ozone and O2:N2 plasma. The surface of the ITO substrate can also be cleaned with an organic solvent to remove surface scum and improve the substrate anode work function.

[0237] The thickness of the anodic vacuum evaporation deposition on the experimental substrate is HATNA is used as the hole injection layer, and a layer with a thickness of The NPB forms a hole transport layer.

[0238] TPD is vacuum-deposited on the hole transport layer to form a layer with a thickness of hole-assisting layer.

[0239] On the hole assisting layer, compound 1:GH(p):Ir(3mppy)3 was co-evaporated at an evaporation rate ratio of 45%:45%:10% to form a layer with a thickness of organic light-emitting layer.

[0240] ET-1 and LiQ were evaporated at a rate ratio of 1:1 to form The electron transport layer is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then magnesium and silver are vacuum evaporated on the electron injection layer at a deposition rate of 1:9 to form a layer with a thickness of cathode.

[0241] In addition, the cathode is deposited The organic cover layer CP-1 is formed, thereby completing the manufacture of the green organic electroluminescent device.

[0242] Examples 2 to 36

[0243] A green organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound shown in Table 11 was used instead of Compound 1 when forming the organic light-emitting layer.

[0244] Comparative Example 1

[0245] A green organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound A was used instead of Compound 1 when forming the organic light-emitting layer.

[0246] Comparative Example 2

[0247] A green organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound B was used instead of Compound 1 when forming the organic light-emitting layer.

[0248] Comparative Example 3

[0249] A green organic electroluminescent device was prepared by the same method as in Example 1, except that Compound C was used instead of Compound 1 when forming the organic light-emitting layer.

[0250] Comparative Example 4

[0251] A green organic electroluminescent device was prepared by the same method as in Example 1, except that Compound D was used instead of Compound 1 when forming the organic light-emitting layer.

[0252] Comparative Example 5

[0253] A green organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound E was used instead of Compound 1 when forming the organic light-emitting layer.

[0254] The material structures used in Examples 1 to 36 and Comparative Examples 1 to 5 are shown in Table 10 below:

[0255] Table 10

[0256]

[0257]

[0258] At 20 mA / cm 2 Under the conditions of , the performance of the organic electroluminescent devices prepared in Examples 1 to 36 and Comparative Examples 1 to 5 was analyzed, and the results are shown in Table 11:

[0259] Table 11

[0260]

[0261]

[0262] According to the data in Table 11, compared with Comparative Examples 1 to 5, in Examples 1 to 36 of the present device, the current efficiency is improved by at least 10.6% and the device life is improved by at least 10.5% by using the nitrogen-containing compound of the present application as the mixed main material of the green organic light-emitting layer, indicating that the nitrogen-containing compound of the present application can effectively extend the life of the organic electroluminescent device and improve the luminous efficiency to a certain extent.

[0263] Example 37 Red organic electroluminescent device

[0264] The anode was prepared by the following process: ITO was deposited to a thickness of A substrate (made by Corning) was cut into a size of 40mm×40mm×0.7mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was treated with ultraviolet ozone and O2:N2 plasma to remove surface scum and improve the substrate anode work function.

[0265] The thickness of the anodic vacuum evaporation deposition on the experimental substrate is The hole injection layer is formed by HATNA, and NPB is evaporated on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0266] TAPC is evaporated on the hole transport layer to form a layer with a thickness of hole-assisting layer.

[0267] Then, RH(p): compound 545: Ir(btp)2(acac) were co-deposited on the hole auxiliary layer at a deposition rate ratio of 49%:49%:2% to form red organic light-emitting layer.

[0268] ET-1 and LiQ were co-evaporated at a rate ratio of 1:1 to form a film with a thickness of The electron transport layer is formed by evaporating Yb on the electron transport layer. The electron injection layer is then vacuum-deposited with magnesium and silver at a deposition rate of 1:10 on the electron injection layer to form cathode.

[0269] The thickness of the evaporated layer on the cathode is CP-1 is added to form an organic covering layer, thereby completing the manufacture of a red organic light-emitting device.

[0270] Examples 38 to 57

[0271] A green organic electroluminescent device was prepared in the same manner as in Example 37, except that the compound shown in Table 13 was used instead of Compound 545 when forming the organic light-emitting layer.

[0272] Comparative Example 6

[0273] A green organic electroluminescent device was prepared by the same method as in Example 37, except that Compound F was used instead of Compound 545 when forming the organic light-emitting layer.

[0274] Comparative Example 7

[0275] A green organic electroluminescent device was prepared by the same method as in Example 37, except that Compound G was used instead of Compound 545 when forming the organic light-emitting layer.

[0276] Comparative Example 8

[0277] A green organic electroluminescent device was prepared by the same method as in Example 37, except that Compound H was used instead of Compound 545 when forming the organic light-emitting layer.

[0278] The material structures used in Examples 37 to 57 and Comparative Examples 6 to 8 are shown in Table 12 below:

[0279] Table 12

[0280]

[0281] At 20 mA / cm 2 Under the conditions of , the performance of the organic electroluminescent devices prepared in Examples 37 to 57 and Comparative Examples 6 to 8 was analyzed, and the results are shown in Table 13:

[0282] Table 13

[0283]

[0284] According to the data in Table 13, compared with Comparative Examples 6 to 8, the current efficiency (Cd / A) of device embodiments 37 to 57 using the nitrogen-containing compound of the present application as the mixed main material of the red organic light-emitting layer is improved by at least 14.2%, and the life is improved by at least 12.1%.

[0285] This application provides a nitrogen-containing compound with a core structure composed of triazine, benzoxazole, and carbazole groups with a specific connection pattern. This specific connection pattern results in a highly distorted structure and high electron transport efficiency, thereby improving the luminous efficiency and lifespan characteristics of organic electroluminescent devices. In particular, when the carbazole group is closer to the oxygen atom of the benzoxazole, the compound's electron transport efficiency is even higher, resulting in better device performance.

[0286] Using the nitrogen-containing compound of the present application as a host material of an organic light-emitting layer of an organic electroluminescent device (especially an electronic host) can significantly improve the efficiency and life of the organic electroluminescent device.

[0287] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection of the present application.

Claims

1. A nitrogen-containing compound, characterized in that The nitrogen-containing compound has a structure shown in the following formula 1: wherein Ring A and Ring B are independently selected from aromatic rings having 6 to 12 carbon atoms; Ar1 and Ar2 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl; Ar3 is phenyl; L and L3 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted fluorenylene group; The substituents in L and L3 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; The substituents in L1 and L2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; R a and R b are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; n a Represents R a The number of n b Represents R b The number of n a and n b are independently selected from 0, 1, 2, 3, 4, 5 or 6.

2. The nitrogen-containing compound according to claim 1, characterized in that The nitrogen-containing compound has a structure shown in any one of Formulas 1-1 to 1-6:

3. The nitrogen-containing compound according to claim 1, characterized in that Ring A and ring B are each independently selected from a benzene ring or a naphthalene ring.

4. The nitrogen-containing compound according to claim 1, characterized in that In formula 1, Selected from the group consisting of:

5. The nitrogen-containing compound according to claim 1, characterized in that are independently selected from the group consisting of:

6. The nitrogen-containing compound according to claim 1, characterized in that The nitrogen-containing compound is selected from the group consisting of the following compounds:

7. An organic electroluminescent device, characterized in that The invention comprises an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the nitrogen-containing compound.

9. An electronic device, characterized in that The organic electroluminescent device according to claim 7 or 8.

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