Nitrogen compounds, organic electroluminescent devices and electronic devices

Abstract

This application belongs to the field of organic electroluminescence technology, and relates to a nitrogen-containing compound and an organic electroluminescent device and electronic device using the same. The nitrogen-containing compound has a structure as shown in Formula 1. Using the nitrogen-containing compound in an organic electroluminescent device can improve the performance of the organic electroluminescent device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to a nitrogen-containing compound, an organic electroluminescent device, and an electronic device. Background Technology

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this application is to provide a nitrogen-containing compound, an organic electroluminescent device, and an electronic device to improve the performance of the organic electroluminescent device.

[0005] To achieve the above-mentioned objective, according to the first aspect of this application, a nitrogen-containing compound is provided, having the structure shown in Formula I:

[0006]

[0007] In Formula 1, ring A and ring B are each independently selected from aromatic rings with 6-16 carbon atoms;

[0008] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0009] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0011] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, phosphonyl with 6 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, aryloxy with 6 to 20 carbon atoms, or arylthio with 6 to 20 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0012] Each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0013] n1 represents the number of R1s, and n2 represents the number of R2s. n1 and n2 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0014] This invention provides a compound with carbazole and its derivatives as the main functional groups, with tetrahydronaphthalene linked at position 9 of the carbazole and its derivatives to increase its tortuosity, reduce intermolecular stacking, and prevent crystallization. The heteroaryl fragments exhibit strong luminescent properties due to their planarity and rigidity, and significantly improve the material's thermal stability and electron affinity. The compound of this application has a relatively three-dimensional structure, which can improve device performance and efficiency. Its stable film-forming properties can also improve lifetime to some extent.

[0015] According to a second aspect of this application, an organic electroluminescent device is provided, 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 comprising the aforementioned nitrogen-containing compound.

[0016] According to a third aspect of this application, an electronic device is provided, the electronic device comprising the above-described organic electroluminescent device. Attached Figure Description

[0017] Figure 1This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application, wherein 100 represents the anode, 200 represents the cathode, 300 represents the functional layer, 310 represents the hole injection layer, 321 represents the first hole transport layer, 322 represents the second hole transport layer, 330 represents the organic light-emitting layer, 340 represents the electron transport layer, and 350 represents the electron injection layer.

[0018] Figure 2 This is a schematic diagram of the structure of an electronic device according to a specific embodiment of this application. Detailed Implementation

[0019] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary 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.

[0020] In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0021] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

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

[0023]

[0024] In Formula 1, ring A and ring B are each independently selected from aromatic rings with 6-16 carbon atoms;

[0025] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0026] L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0027] Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0028] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, phosphonyl with 6 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, aryloxy with 6 to 20 carbon atoms, or arylthio with 6 to 20 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0029] Each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0030] n1 represents the number of R1s, and n2 represents the number of R2s. n1 and n2 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0031] This invention provides a compound with carbazole and its derivatives as the main functional groups, with tetrahydronaphthalene linked at position 9 of the carbazole and its derivatives to increase its tortuosity, reduce intermolecular stacking, and prevent crystallization. The heteroaryl fragments exhibit strong luminescent properties due to their planarity and rigidity, and significantly improve the material's thermal stability and electron affinity. The compound of this application has a relatively three-dimensional structure, which can improve device performance and efficiency. Its stable film-forming properties can also improve lifetime to some extent.

[0032] In this application, the descriptive phrases "each...independently selected from," "...each independently selected from," and "...each independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0033] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, heteroaryl, aryl, trialkylsilyl, triphenylsilyl, alkyl, haloalkyl, cycloalkyl, deuterated phenyl, etc. The number of substituents can be one or more.

[0034] In this application, "multiple" means two or more, such as two, three, four, five, six, seven, eight, nine, ten or more.

[0035] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the sum of the number of carbon atoms in that functional group and all its substituents.

[0036] In this application, the number of carbon atoms in L1, L2, L, R1, R2, R3, R4, Ar1, and Ar2 refers to the total number of carbon atoms in that group. For example, if Ar1 is selected from an aryl group with 10 substituted carbon atoms, then the total number of carbon atoms in the aryl group and its substituents is 10. As another example, if Ar1 is 9,9-dimethylfluorenyl, then Ar1 is a fluorenyl group with 15 substituted carbon atoms, and the number of carbon atoms in the cyclic group of Ar1 is 13.

[0037] In this application, unless otherwise specifically defined, "heteroatom" means a functional group comprising at least one heteroatom such as B, N, O, S, Si, Se, or P, with the remaining atoms being carbon and hydrogen. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.

[0038] In this application, "ring" includes saturated rings and unsaturated rings; saturated rings are saturated aliphatic rings, and unsaturated rings are partially unsaturated rings, such as cyclohexene or aromatic rings, such as aromatic rings and heteroaromatic rings.

[0039] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered ring. Saturated or unsaturated 3- to 15-membered rings refer to cyclic groups having 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane, cyclohexane, fluorene rings, and benzene rings.

[0040] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0041] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthrene, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthrene, pyrene, benzofluoranthyl, etc. Base, etc.

[0042] In this application, the term "arylene" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0043] In this application, terphenyl includes

[0044] In this application, the number of carbon atoms in the substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0045] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0046] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0047] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.

[0049] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.

[0050] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0051] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0052] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0053] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0054] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0055] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0056] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0057] In this application, Both refer to the chemical bonds that connect groups to each other.

[0058] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0059]

[0060] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned connecting bond extending from the middle of one benzene ring on one side. The meanings it represents include any possible connection modes shown in the formulas (X'-1) to (X'-4):

[0061]

[0062] The unpositioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, indicating that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is connected to the quinoline ring through an unpositioned connecting bond. The meanings it represents include any possible connection modes shown in the formulas (Y-1) to (Y-7):

[0063]

[0064] In some embodiments, the nitrogen-containing compound is selected from the structures shown in the following formulas (1-1) to (1-16):

[0065]

[0066]

[0067] In some embodiments, ring A and ring B are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring or a pyrene ring.

[0068] In some embodiments, Het is selected from the following groups:

[0069] <000□□166>

[0070] Represents the bond connected to L, Represents the bond connected to L1, Represents the bond connected to L2; the formula does not contain Of, represents the In, L2 is a single bond and Ar2 is hydrogen.

[0071] In some embodiments, Het is selected from the following groups:

[0072]

[0073] Represents the bond connected to L, Represents the bond connected to L1, Represents the bond connected to L2; the formula does not contain Of, represents the In this context, L2 represents a single bond, and Ar2 represents hydrogen.

[0074] In some embodiments, L, L1, and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0075] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0076] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 5-12 carbon atoms.

[0077] In some embodiments, L, L1, and L2 are each independently selected from the group consisting of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.

[0078] Optionally, the substituents in L, L1, and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, or naphthyl.

[0079] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single-bonded or substituted or unsubstituted groups Q, wherein the unsubstituted group Q is selected from the group consisting of:

[0080]

[0081] The substituents in the above-mentioned substituted groups Q may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl or naphthyl.

[0082] In some embodiments, L, L1, and L2 are each independently selected from single bonds or the following groups:

[0083]

[0084] In some embodiments, L is selected from single bonds or the following groups:

[0085]

[0086]

[0087] In some implementations, L is a single bond.

[0088] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms;

[0089] Ar2 is selected from the group consisting of hydrogen, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.

[0090] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 7 to 20 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 7 to 20 carbon atoms.

[0091] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, and trialkylsilyl with 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0092] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted... Carbazolyl; Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl.

[0093] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl; optionally, any two adjacent substituents in Ar1 and Ar2 form a benzene ring or a fluorenyl ring.

[0094] In some embodiments, Ar1 is selected from substituted or unsubstituted groups V; Ar2 is selected from hydrogen, substituted or unsubstituted groups V; wherein the unsubstituted group V is selected from the following groups:

[0095]

[0096] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0097] In some embodiments, Ar1 is selected from the following groups; Ar2 is selected from hydrogen or the following groups:

[0098]

[0099] In some implementations... Selected from the group consisting of the following groups, Selected from hydrogen or the following groups:

[0100]

[0101] In some embodiments, each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0102] In some implementations... Selected from the group consisting of the following groups:

[0103]

[0104]

[0105] In some embodiments, the nitrogen-containing compound described in this application is selected from the group consisting of:

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] A second aspect of this application provides an organic electroluminescent device, which includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the aforementioned nitrogen-containing compound to improve the voltage characteristics, efficiency characteristics and lifetime characteristics of the organic electroluminescent device.

[0122] Optionally, the nitrogen-containing compound provided in this application can be used to form at least one organic film layer in the functional layer.

[0123] Optionally, the functional layer includes an organic light-emitting layer, which includes the nitrogen-containing compound. The organic light-emitting layer may be composed of the nitrogen-containing compound provided in this application, or it may be composed of the nitrogen-containing compound provided in this application and other materials.

[0124] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.

[0125] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0126] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0127]

[0128] In one embodiment, the first hole transport layer 321 may be composed of HT-1.

[0129] In one embodiment, the second hole transport layer 322 is composed of HT-2 or HT-3.

[0130] Optionally, a hole injection layer 310 is further provided 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 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof:

[0131]

[0132] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.

[0133] In this application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, 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 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0134] The host material of the organic light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises a nitrogen-containing compound of this application; more preferably, the host material of the organic light-emitting layer 330 comprises at least one of compounds 1 to 324 of this application. Optionally, the host material may also comprise RH-P.

[0135] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to:

[0136]

[0137]

[0138] In one embodiment of this application, the organic light-emitting device is a red organic light-emitting device or a green organic light-emitting device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises a nitrogen-containing compound of this application. The guest material is, for example, RD-1 or GD-1.

[0139] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of this application. In one embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of this application and Or contains nitrogen-containing compounds as described in this application and

[0140] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0141]

[0142] In one embodiment of this application, the electron transport layer 340 may be composed of ET-1 and LiQ, or ET-2 and LiQ.

[0143] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0144] Optionally, an electron injection layer 350 is 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 inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).

[0145] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0146] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0147] Synthesis example

[0148] The following synthetic examples and embodiments are used to further illustrate and explain the contents of this application.

[0149] Generally, the nitrogen-containing compounds of this application can be prepared by the methods described herein. Unless further specified, the meanings of the substituent symbols in this application are the same as those in Chemical Formula I. Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many other nitrogen-containing compounds of this application, and that other methods for preparing the nitrogen-containing compounds of this application are considered to be within the scope of this invention.

[0150] For example, those skilled in the art can synthesize other nitrogen-containing compounds of this application by referring to or appropriately modifying the preparation methods provided in this application, such as by using appropriate protecting groups, utilizing other known reagents other than those described in this application, or modifying reaction conditions.

[0151] In the synthesis examples described below, all temperatures are in degrees Celsius unless otherwise stated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company, and Alfa Chemical Company, and were used without further purification unless otherwise stated. Some common reagents were purchased from Shantou Xilong Chemical Plant, Guangdong Guanghua Chemical Reagent Plant, Guangzhou Chemical Reagent Plant, Tianjin Haoyuyu Chemical Co., Ltd., Tianjin Fuchen Chemical Reagent Plant, Wuhan Xinhuayuan Technology Development Co., Ltd., Qingdao Tenglong Chemical Reagent Co., Ltd., and Qingdao Haiyang Chemical Plant. Toluene was obtained by reflux drying with metallic sodium. n-Hexane was pre-dried with anhydrous sodium sulfate before use.

[0152] Unless otherwise stated, the following reactions are generally carried out under positive pressure of nitrogen or argon, or with a drying tube attached to an anhydrous solvent; reaction flasks are sealed with suitable rubber stoppers, and the substrate is injected into the reaction flasks using a syringe. All glassware is dried.

[0153] 1 H NMR spectra were recorded using a Bruker 400MHz or 600MHz NMR spectrometer. 1¹H NMR spectra were performed using CDCl₃, CD₂Cl₂, D₂O, DMSO-d₆, CD₃OD, or acetone-d₆ as solvents (in ppm).

[0154] (1) Synthesis of intermediate A-1

[0155]

[0156] The following ingredients were added: SM-A-1 (10 g, 35.3 mmol), SM-B-1 (5.9 g, 35.3 mmol), potassium carbonate (10.7 g, 77.7 mmol), cuprous iodide (1.3 g, 7.1 mmol), 18-crown ether-6 (0.9 g, 3.5 mmol), 1,10-phenanthroline (2.8 g, 14.1 mmol), and N,N-dimethylformamide (100 mL). After 24 h, the reaction was complete. The mixture was cooled to room temperature, and 500 mL of water was added. A large amount of solid precipitated out. The mixture was filtered, and the filter cake was completely dissolved in 300 mL of dichloromethane. The solution was washed with water until neutral, and the organic layer was dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (dichloromethane / n-heptane) to obtain A-1 (9.1 g, 70% yield).

[0157] Referring to the synthesis of A-1, use SM-AX to replace SM-A-1 and SM-BX to replace SM-B-1 as shown in Table 1 to synthesize intermediate AX in Table 1.

[0158] Table 1:

[0159]

[0160] (2) Synthesis of intermediate B-1

[0161]

[0162] A-1 (10 g, 27.1 mmol) was dissolved in dichloromethane, and pyridine (6.4 g, 81.2 mmol) was added with stirring at room temperature. The mixture was cooled to 0°C, and trifluoromethanesulfonic anhydride (11.5 g, 40.6 mmol) was added dropwise. The mixture was then heated to room temperature and reacted for 2 h. After the reaction was complete, the pH was adjusted to neutral with saturated sodium bicarbonate solution, and the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain B-1 (8.1 g, 60% yield).

[0163] Referring to the synthesis of B-1, replace A-1 with AX as shown in the table to synthesize intermediate BX in Table 2.

[0164] Table 2:

[0165]

[0166]

[0167] (3) Synthesis of intermediate C-1

[0168]

[0169] Under a nitrogen atmosphere, B-1 (20 g, 39.8 mmol), m-chlorophenylboronic acid (6.2 g, 39.8 mmol), tetra(triphenylphosphine)palladium (0.5 g, 0.4 mmol), anhydrous potassium carbonate (11 g, 79.8 mmol), tetrabutylammonium bromide (0.13 g, 0.4 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain C-1 (13 g, 70% yield).

[0170] Following the synthesis of C-1, BX was used to replace B-1 as shown in the table, and SM-CX was used to replace m-chlorophenylboronic acid to synthesize the intermediate CX in Table 3.

[0171] Table 3:

[0172]

[0173]

[0174] (4) Synthesis of intermediate D-1

[0175]

[0176] B-1 (20 g, 39.9 mmol) was dissolved in 1,4-dioxane (200 mL), followed by the addition of tris(dibenzylacetone)palladium (0.4 g, 0.4 mmol), potassium acetate (11.7 g, 119.6 mmol), pinacol diboronate (12.2 g, 47.8 mmol), and x-phos (0.2 g, 0.4 mmol). The mixture was stirred and heated to reflux for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by filtration and vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain D-1 (13.0 g, 68% yield).

[0177] Referring to the synthesis of D-1, replace B-1 with BX or CX as shown in Table 4 to synthesize the intermediate DX in Table 4.

[0178] Table 4:

[0179]

[0180]

[0181]

[0182] Synthesis of Compound 1:

[0183]

[0184] Under a nitrogen atmosphere, D-1 (20 g, 39.8 mmol), SM-N-1 (6.2 g, 39.8 mmol), tetra(triphenylphosphine)palladium (0.5 g, 0.4 mmol), anhydrous potassium carbonate (11 g, 79.8 mmol), tetrabutylammonium bromide (0.13 g, 0.4 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain 1 (13 g, 70% yield).

[0185] Referring to the synthesis of compound 1, compound Y in Table 5 was synthesized by replacing D-1 with DX and SM-N-1 with SM-NX as shown in Table 5.

[0186] Table 5:

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] Synthesis of Compound 384

[0193]

[0194] Under a nitrogen atmosphere, compound 1 (10.0 g, 17.1 mmol) and 100 mL of benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (15.6 g, 103.4 mmol) was added. The mixture was heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 20 mL of heavy water was added, and the mixture was stirred for 10 minutes. Then, a saturated aqueous solution of K3PO4 was added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain 384 (6.2 g, 60% yield).

[0195] Mass spectra of the synthesized compound:

[0196]

[0197]

[0198] The NMR data for some compounds are shown in Table 6 below:

[0199]

[0200] Device Examples

[0201] This invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises the aforementioned organic compound of this invention. The organic electroluminescent device of this invention will now be described in detail through embodiments. However, the following embodiments are merely examples of this invention and are not intended to limit the invention.

[0202] Example 1: Red Organic Electroluminescent Device

[0203] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0204] On the experimental substrate (anode), PD and compound HT-1 were co-deposited at a deposition rate of 2%:98% to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer. The first hole transport layer.

[0205] The compound HT-2 was vacuum-deposited on the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0206] Next, on the second hole transport layer, compound 89:RH-P:RD-1 was co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0207] On the light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0208] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP-1 is used to form an organic capping layer (CPL), thereby completing the fabrication of the red organic electroluminescent device.

[0209] Examples 2-26

[0210] Except that, when fabricating the light-emitting layer, compound Z from Table 6 is used instead of compound 89 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0211] Comparative Examples 1-2

[0212] Except that, when fabricating the light-emitting layer, compounds A and B were used instead of compound 89 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0213] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0214] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0215]

[0216] The performance of the red organic electroluminescent devices prepared in Examples 1-26 and Comparative Examples 1-2 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7 below.

[0217] Table 7

[0218]

[0219]

[0220] Referring to Table 7 above, by comparing the performance of the organic electroluminescent devices prepared in Examples 1 to 58 with those in Comparative Examples 1 to 4, when the nitrogen-containing compound of the present invention is used as the main material of the red organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is increased by at least 12% and the lifetime is increased by at least 11.8%.

[0221] Example 27: Green Organic Light Emitting Device

[0222] The anode is prepared through the following process: A thickness of [missing information] is [missing information]. The ITO substrate (manufactured by Corning) is cut to a size of 40mm×40mm×0.7mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography. The surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove slag.

[0223] On the experimental substrate (anode), PD and compound HT-1 were co-deposited at a deposition rate of 2%:98% to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and HT-1 is deposited on the hole injection layer to form a thickness of [thickness value missing]. The first hole transport layer.

[0224] HT-3 was vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer.

[0225] On the second hole transport layer, compound 1:GH-P:GD-1 was co-deposited in a ratio of 54%:42%:4% (co-evaporation rate ratio: compound B-3:GH-P:GD-1 = 0.6:0.4:0.1) to form a layer with a thickness of [missing information]. The green light-emitting layer (EML).

[0226] ET-1 and LiQ were mixed in a 1:1 weight ratio and then vapor-deposited to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0227] Furthermore, the thickness of the evaporation deposit on the aforementioned cathode is... The CP-1 is used to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device. The fabricated device is referred to as Example 22.

[0228] Examples 28 to 35

[0229] Except that compound 1 was replaced with compound T as shown in Table 7 during the formation of the light-emitting layer, organic electroluminescent devices were fabricated using the same method as in Example 28. The fabricated devices are referred to as Examples 28 to 385.

[0230] Comparative Examples 3 to 4

[0231] Except that, when fabricating the light-emitting layer, compounds C and D were used instead of compound 1 from Example 28, respectively, an organic electroluminescent device was prepared using the same method as in Example 28.

[0232] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0233]

[0234] The performance of the green organic electroluminescent devices of Examples 27-35 and Comparative Examples 3-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. 95 Device lifetime is 20 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 8 below.

[0235] Table 8

[0236]

[0237]

[0238] Referring to Table 8 above, by comparing the performance of the organic electroluminescent devices prepared in Examples 28-35 and Comparative Examples 3-4, when the nitrogen-containing compound of the present invention is used as the main material of the red organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is increased by at least 12.9% and the lifetime is increased by at least 14.7%.

[0239] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0240] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not describe the various possible combinations separately.

Claims

1. A nitrogen-containing compound, characterized in that, It has the structure shown in Equation 1: In Formula 1, ring A and ring B are each independently selected from aromatic rings with 6-16 carbon atoms; Het is selected from the following groups; L, L1, and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group; Ar1 and Ar2 may be the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L, L1 and L2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, phenyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, and deuterated alkyl with 1 to 10 carbon atoms. The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, phosphonyl groups with 6 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents in Ar1 and Ar2 form a saturated or unsaturated 3 to 15-membered ring; Each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n1 represents the number of R1s, and n2 represents the number of R2s. n1 and n2 are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. - # represents the key connected to L, represents the key connected to L1, represents the key connected to L2; the formula does not contain if not, it represents the where L2 is a single bond and Ar2 is hydrogen.

2. The nitrogen-containing compound according to claim 1, wherein, Ring A and ring B are each independently selected from benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring or pyrene ring.

3. The nitrogen-containing compound according to claim 1, wherein, The nitrogen-containing compound has the structures shown in formulas (1-1) to (1-16):

4. The nitrogen-containing compound according to claim 1, wherein, Het is selected from the following groups: - # represents the key connected to L, represents the key connected to L1, represents the key connected to L2; the formula does not contain For those without, it represents the one connected at this position In this case, L2 is a single bond and Ar2 is hydrogen.

5. The nitrogen-containing compound according to claim 1, wherein, The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, or phenyl.

6. The nitrogen-containing compound according to claim 1, wherein, L, L1, and L2 are each independently selected from single bonds or the following groups:

7. The nitrogen-containing compound according to claim 1, wherein, Ar1 is selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 7 to 20 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 7 to 20 carbon atoms. The substituents in Ar1 and Ar2 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, and trialkylsilyl with 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

8. The nitrogen-containing compound according to claim 1, wherein, Ar1 is selected from substituted or unsubstituted groups V; Ar2 is selected from hydrogen, substituted or unsubstituted groups V; wherein the unsubstituted group V is selected from the following groups: The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

9. The nitrogen-containing compound according to claim 1, wherein, Selected from the group consisting of the following groups, Selected from hydrogen or the following groups:

10. The nitrogen-containing compound according to claim 1, wherein, Each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

11. The nitrogen-containing compound according to claim 1, wherein, Selected from the group consisting of the following groups:

12. 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:

13. 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 comprising a nitrogen-containing compound according to any one of claims 1-12.

14. The organic electroluminescent device according to claim 13, wherein, The functional layer includes an organic light-emitting layer, which comprises the nitrogen-containing compound.

15. An electronic device comprising the organic electroluminescent device of claim 13 or 14.

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