Nitrogen-containing compounds and organic electroluminescent devices and electronic devices

Abstract

This application relates to the field of organic electroluminescent materials technology, providing a nitrogen-containing compound and an organic electroluminescent device and electronic apparatus containing the same. The nitrogen-containing compound of this application comprises an indole-fused phenothiazine / phenotoxazine core structure. When this nitrogen-containing compound is used as the host material of the light-emitting layer of an organic electroluminescent device, the luminous efficiency and lifespan of the device can be significantly improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to nitrogen-containing compounds and organic electroluminescent devices and electronic devices containing the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. 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 the 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. The 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] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide a nitrogen-containing compound and electronic components and devices containing the same, wherein the nitrogen-containing compound can be used in organic electroluminescent devices to improve the performance of the devices.

[0005] According to a first aspect of this application, a nitrogen-containing compound is provided, the nitrogen-containing compound having the structure shown in Formula 1:

[0006]

[0007] Where X is selected from S or O;

[0008] Group A is selected from the structure shown in formula a-1 or the structure shown in formula a-2;

[0009]

[0010] HAr is selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0011] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0012] The substituents in HAr may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, or aryl with 6 to 20 carbon atoms;

[0013] L, L1, L2 and L3 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.

[0014] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0015] Ar3 is 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;

[0016] Ar4 is selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms, or Ar4 is a single bond;

[0017] The substituents of L, L1, L2, L3, Ar1, Ar2, Ar3, and Ar4 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, deuteralkyl 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, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 form a saturated or unsaturated 3 to 15-membered ring.

[0018] Each of R1, R2, and R3 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. Optionally, any two adjacent groups form a benzene ring.

[0019] n1 represents the number of R1s, which can be selected from 0, 1, 2, 3 or 4; n2 represents the number of R2s, which can be selected from 0, 1, 2 or 3; n3 represents the number of R3s, which can be selected from 0, 1, 2, 3 or 4.

[0020] 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.

[0021] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0022] The compounds in this application contain a core structure of indole-fused phenothiazine / phenotoxazine. The sulfur or oxygen atoms in the indole-fused phenothiazine / phenotoxazine each possess two lone pairs of electrons, endowing the core structure with excellent hole transport capabilities. When this core structure is linked to an aryl or electron-rich heteroaryl group, the hole transport capability of the compound is enhanced; such compounds are suitable for p-type materials in mixed-type host materials. When this core structure is linked to a nitrogen-containing heteroaryl group with electron transport properties, the compound simultaneously possesses excellent hole and electron transport performance; such compounds are suitable for single-type host materials. Using the compounds of this application as both p-type and single-type host materials in mixed-type host materials can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance device luminous efficiency and lifetime. Attached Figure Description

[0023] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0024] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0025] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0026] Figure Labels

[0027] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0028] 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer; 340. Electron transport layer

[0029] 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0030] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of 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. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0031] In a first aspect, this application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0032]

[0033] in, Connected to On any carbon or nitrogen atom;

[0034] X is selected from S or O;

[0035] Group A is selected from the structure shown in formula a-1 or the structure shown in formula a-2;

[0036]

[0037] HAr is selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0038] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0039] The substituents in HAr may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, or aryl with 6 to 20 carbon atoms;

[0040] L, L1, L2 and L3 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.

[0041] A r1 and A r2 They may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;

[0042] A r3 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;

[0043] A r4 Selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms, or Ar4 as a single bond;

[0044] when Connected to When Ar4 is at the $ site on the middle $-$, it is a single bond;

[0045] The substituents in L, L1, L2, L3, Ar1, Ar2, Ar3, and Ar4 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, deuteralkyl 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, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 form a saturated or unsaturated 3 to 15-membered ring;

[0046] Each of R1, R2, and R3 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. Optionally, any two adjacent groups form a benzene ring.

[0047] n1 represents the number of R1 elements, which can be selected from 0, 1, 2, 3, or 4; n2 represents the number of R2 elements, which can be selected from 0, 1, 2, or 3; n3 represents the number of R3 elements. n3 Choose from 0, 1, 2, 3 or 4.

[0048] Optionally, any two adjacent R1s can form a benzene ring.

[0049] Optionally, any two adjacent R2s can form a benzene ring.

[0050] Optionally, any two adjacent R3s can form a benzene ring.

[0051] In this application, the terms "optionally" and "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. As another example, "optionally, any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 form a ring" means that any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 are connected to each other to form a ring, or any two adjacent substituents in Ar1, Ar2, Ar3, and Ar4 can exist independently. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0052] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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.

[0053] 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, alkyl, haloalkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0054] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0055] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0056] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0057] 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, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0058] In this application, the term "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0059] In this application, terphenyl includes

[0060] In this application, the number of carbon atoms in the 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 refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0061] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 40 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; and in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0062] 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.

[0063] In this application, the aryl groups used as substituents for L, L1, L2, L3, Ar1, Ar2, Ar3, and Ar4 are, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0064] 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.

[0065] 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.

[0066] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl group) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 40; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.

[0067] In this application, the heteroaryl groups that serve as substituents for L, L1, L2, L3, Ar1, Ar2, Ar3, and Ar4 are, for example but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenantholinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, and dibenzofuranyl.

[0068] 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 atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0069] 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.

[0070] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0071] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0072] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0073] 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.

[0074] In this application, a nitrogen-containing heteroaryl group with 3-20 carbon atoms refers to a heteroaryl group having 3-20 carbon atoms and containing at least 1 nitrogen atom.

[0075] In this application, "-*", "-$", and "-#" all refer to chemical bonds that connect with other groups. The various markings on the bonds are only for distinguishing them from each other.

[0076] 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 be connected to any position in the ring system that the linker penetrates, and the other end is connected 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 penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0077]

[0078]

[0079] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0080]

[0081] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0082]

[0083] In some embodiments, the compound shown in Formula 1 is selected from the structures shown below:

[0084]

[0085] In some embodiments, the compound shown in Formula 1 is selected from the structures shown below:

[0086]

[0087] The compounds in this application When the group connection method is as shown in Formulas 2-1 to 2-7, the core stability is high and the molecular thermal stability is improved. When applied to the light-emitting layer of a device, it can improve the device lifetime.

[0088] In this application, Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms. Preferably, the Het group contains at least two nitrogen atoms.

[0089] In some embodiments, Het is selected from triazine, pyrimidinyl, or pyridinyl.

[0090] In some implementations, Het is selected from Where -* represents the key connected to L, Indicates the key connected to L1 or L2.

[0091] In some embodiments of this application, Het or HAr is an electron-deficient nitrogen-containing heteroaryl group (also known as an electron-poor heteroaryl group), wherein the electron-deficient nitrogen-containing heteroaryl group contains at least one nitrogen atom, sp 2 Hybridized nitrogen atoms, as a whole, reduce rather than increase the electron cloud density of the conjugated system of heteroaryl groups. The lone pair electrons on the heteroatom do not participate in the conjugated system, and the strong electronegativity of the heteroatom further reduces the electron cloud density. For example, electron-deficient nitrogen-containing heteroaryl groups can include, but are not limited to, triazinyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinel, benzoquinazolyl, phenanthrolinezolyl, benzofuranopyrimidinyl, and benzothiophenepyrimidinyl. Electron-deficient nitrogen-containing heteroaryl groups can form the electron transport core group of the compound, enabling efficient electron transport and thus effectively balancing the electron and hole transport rates in the organic light-emitting layer.

[0092] In other embodiments of this application, HAr is an electron-rich aromatic group with a high overall electron cloud density. For example, electron-rich aromatic groups may include, but are not limited to, phenylene, naphthylene, biphenylene, anthracene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, carbazolyl, triphenylene, pyrene, perylene, spirodifluorene, etc. Electron-rich aromatic groups can form hole-transporting auxiliary groups in the compound, enabling the compound to effectively achieve hole transport, thereby effectively balancing the electron and hole transport rates in the organic light-emitting layer.

[0093] In some embodiments, HAr is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0094] Optionally, the substituents in HAr may be the same or different, and each may be independently selected from deuterium, cyano, halogen groups or alkyl groups having 1 to 4 carbon atoms, deuterated alkyl groups having 1 to 4 carbon atoms or aryl groups having 6 to 12 carbon atoms.

[0095] In some embodiments, HAr is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted spirodifluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, or selected from substituted or unsubstituted groups:

[0096] ;-# indicates the key connected to L, The term indicates the bond connected to L3; the substituents in HAr may be the same or different, and are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, alkyl or phenyl with 1 to 4 carbon atoms.

[0097] In some embodiments, HAr is selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups:

[0098]

[0099] -# indicates the key connected to L. Indicates the key connected to L3;

[0100] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl, and when the number of substituents is greater than 1, the substituents may be the same or different.

[0101] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.

[0102] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0103] In some embodiments, Ar3 is selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.

[0104] In some embodiments, Ar3 is selected from hydrogen, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0105] In some embodiments, Ar4 is selected from single bonds, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.

[0106] In some embodiments, Ar4 is selected from single bonds and substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0107] In some embodiments, the substituents in Ar1, Ar2, Ar3 and Ar4 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.

[0108] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl.

[0109] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl. Optionally, any two adjacent substituents in Ar1 and Ar2 form a benzene ring.

[0110] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0111]

[0112]

[0113] In some embodiments, Ar3 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted quinolinyl.

[0114] Optionally, the substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, benzoxazolyl, or benzothiazoyl. Optionally, any two adjacent substituents in Ar3 form a benzene ring.

[0115] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W; Ar3 is selected from hydrogen, substituted or unsubstituted groups W; Ar4 is a single bond or is selected from substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of:

[0116]

[0117]

[0118] The substituted group W has one or more substituents, and each substituent in the substituted group W is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzoxazolyl, or benzothiazolyl. When the number of substituents on the group W is greater than 1, the substituents may be the same or different.

[0119] In some embodiments, Ar3 is selected from the group consisting of hydrogen or the following groups:

[0120]

[0121]

[0122] In some embodiments, Ar4 is selected from single bonds, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazole.

[0123] Optionally, the substituents in Ar4 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthio, dibenzothiophene, dibenzofuranyl, or carbazolyl. Optionally, any two adjacent substituents in Ar4 form a benzene ring.

[0124] In some embodiments, Ar4 is selected from the group consisting of single bonds or the following groups:

[0125]

[0126]

[0127] In some embodiments, L, L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0128] Optionally, the substituents in L, L1, L2 and L3 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterylalkyl with 1 to 4 carbon atoms, phenyl or naphthyl.

[0129] In some embodiments, L and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0130] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, and substituted or unsubstituted pyridylene.

[0131] Optionally, the substituents in L, L3, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0132] In some embodiments, L and L3 are each independently selected from the group consisting of single bonds or the following groups:

[0133]

[0134] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0135]

[0136]

[0137] In some embodiments, each of R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl. Optionally, any two adjacent groups form a benzene ring.

[0138] In some embodiments, group A is selected from the group consisting of:

[0139]

[0140]

[0141] Optionally, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound described in the first aspect of this application.

[0160] The nitrogen-containing compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0161] 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.

[0162] 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 (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.

[0163] 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.

[0164] 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:

[0165]

[0166]

[0167] In one embodiment, the first hole transport layer 321 may be composed of α-NPDs.

[0168] In one embodiment, the second hole transport layer 322 is composed of HT-1.

[0169] 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 can, for example, be selected from the following compounds or any combination thereof;

[0170]

[0171] In one embodiment, the hole injection layer 310 is composed of a PD.

[0172] 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.

[0173] The host material of the organic light-emitting layer 330 may include metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material may include the nitrogen-containing compounds of this application.

[0174] 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,

[0175]

[0176]

[0177] In one embodiment of this application, the organic electroluminescent device is a red 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. The guest material may be, for example, Ir(Mphq)3.

[0178] 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. The guest material may be, for example, fac-Ir(ppy)3.

[0179] 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:

[0180]

[0181] In one embodiment of this application, the electron transport layer 340 may be composed of BTB and LiQ, or ET-2 and LiQ.

[0182] 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.

[0183] 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).

[0184] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0185] 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.

[0186] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this disclosure is not limited thereto.

[0187] Synthesis Examples

[0188] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. The compounds synthesized by methods not mentioned in this application are all commercially available starting materials.

[0189] Synthesis of Sub-a1:

[0190]

[0191] Under a nitrogen atmosphere, indole (5.85 g, 50 mmol), 1-bromo-4-chloronaphthalene (13.20 g, 55 mmol), cuprous iodide (0.19 g, 1 mmol), o-phenanthroline (3.60 g, 20 mmol), 18-crown ether-6 (1.32 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), and DMF (150 mL) were added sequentially to a 500 mL 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 magnesium 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 as the mobile phase to obtain a white solid, Sub-a1 (11.36 g, 82% yield).

[0192] Referring to the synthesis of Sub-a1, Sub-a2 and Sub-a3 were synthesized by replacing 1-bromo-4-chloronaphthalene with reactant A shown in Table 1.

[0193] Table 1: Synthesis of Sub-a2 and Sub-a3

[0194]

[0195] Synthesis of Sub-b1:

[0196]

[0197] Under a nitrogen atmosphere, the reactants (CAS: 3377-71-7, 10.36 g, 50 mmol), 2-chlorocyclohexanone (6.60 g, 50 mmol), anhydrous sodium carbonate (6.36 g, 60 mmol), and 2,2,2-trifluoroacetic acid (75 mL) were added to a 250 mL three-necked flask, and the mixture was stirred at room temperature for 48 hours. After the reaction was completed, 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 as the mobile phase to give a white solid Sub-b1 (11.97 g, yield 79%).

[0198] Referring to the synthesis of Sub-a1, Sub-b2 to Sub-b12 were synthesized by replacing CAS:3377-71-7 with reactant B shown in Table 2.

[0199] Table 2: Synthesis of Sub-b2 to Sub-b12

[0200]

[0201] Synthesis of Sub-c1:

[0202]

[0203] Under air atmosphere, Sub-b8 (14.45 g, 50 mmol), 2-amino-4-chlorothiophenol (11.92 g, 75 mmol), sodium periodate (2.16 g, 10 mmol), DMSO (15.63 g, 200 mmol), and 1,4-dioxane (150 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred for 12 hours. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium 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 / ethyl acetate as the mobile phase to obtain a white solid, Sub-c1 (8.71 g, yield 41%).

[0204] Referring to the synthesis of Sub-c1, Sub-c2 to Sub-c14 were synthesized by replacing Sub-b8 with reactant C shown in Table 3 and replacing 2-amino-4-chlorothiophenol with reactant D.

[0205] Table 3: Synthesis of Sub-c2 to Sub-c14

[0206]

[0207]

[0208] Synthesis of Sub-d1:

[0209]

[0210] Under air atmosphere, Sub-c1 (21.20 g, 50 mmol), cuprous bromide (1.43 g, 10 mmol), and DMF (220 mL) were added to a 500 mL three-necked flask. Stirring and heating were started, and the reaction was carried out at 100 °C for 12 h. After the system cooled to room temperature, it was extracted with dichloromethane (150 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium 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 / ethyl acetate as the mobile phase to obtain a white solid, Sub-d1 (14.16 g, yield 67%).

[0211] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d14 were synthesized by replacing Sub-c1 with reactant E shown in Table 4.

[0212] Table 4: Synthesis of Sub-d2 to Sub-d14

[0213]

[0214]

[0215]

[0216] Synthesis of Sub-e1

[0217]

[0218] Under a nitrogen atmosphere, Sub-d1 (21.10 g, 50 mmol), 4-chlorophenylboronic acid (8.58 g, 55 mmol), palladium acetate (0.22 g, 1.0 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 0.95 g, 2 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (220 mL), tetrahydrofuran (55 mL), and deionized water (55 mL) were added sequentially to a 500 mL 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 magnesium 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 as the mobile phase to obtain a white solid Sub-e1 (18.18 g, yield 73%).

[0219] Referring to the synthesis of Sub-e1, Sub-e2 was synthesized by replacing 4-chlorophenylboronic acid with reactant F shown in Table 5.

[0220] Table 5: Synthesis of Sub-e2

[0221]

[0222] Synthesis of Sub-f1:

[0223]

[0224] Under a nitrogen atmosphere, Sub-d4 (20.11 g, 50 mmol), potassium tert-butoxide (56.10 g, 500 mmol), and DMSO (300 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the reaction was carried out at 50–60 °C for 4 h. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, resulting in a precipitate. The precipitate was filtered and collected. The filtrate was dissolved in dichloromethane (200 mL), dried over anhydrous sodium sulfate, filtered again, and the filtrate was collected. 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 a white solid compound, Sub-f1 (13.11 g, yield 84%).

[0225] Following the synthesis of Sub-f1, Sub-f2 was synthesized by replacing Sub-d4 with reactant G as shown in Table 6.

[0226] Table 6: Synthesis of Sub-f2

[0227]

[0228] Synthesis of Sub-g1

[0229]

[0230] Under a nitrogen atmosphere, Sub-f2 (17.30 g, 50 mmol), 1-(4-bromophenyl)naphthalene (15.51 g, 55 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.916 g, 1 mmol), XPhos (0.95 g, 2 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 100 mmol), and toluene (180 mmol) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water and stirred thoroughly for 30 min. The mixture was then filtered, and the filter cake was washed with deionized water until neutral, followed by washing with anhydrous ethanol (200 mL). The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-g1 (20.0 g, yield 73%).

[0231] Referring to the synthesis of Sub-g1, Sub-g2 was synthesized by replacing Sub-f2 with reactant H and 1-(4-bromophenyl)naphthalene with reactant J as shown in Table 7.

[0232] Table 7: Synthesis of Sub-g2

[0233]

[0234] Synthesis of Sub-h1

[0235]

[0236] Under a nitrogen atmosphere, Sub-d5 (21.10 g, 50 mmol), pinacol diborate (15.24 g, 60 mmol), potassium acetate (9.81 g, 100 mmol), and 1,4-dioxane (220 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and when the system reached 40 °C, Pd2(dba)3 (0.46 g, 0.5 mmol) and XPhos (0.48 g, 1.0 mmol) were quickly added. The temperature was then raised to reflux, and the reaction was stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved in 200 mL of toluene, and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-h1 (19.54 g, yield 76%) was obtained.

[0237] Referring to the synthesis of Sub-h1, Sub-h2 to Sub-h16 were synthesized by replacing Sub-d5 with reactant K as shown in Table 8.

[0238] Table 8: Synthesis of Sub-h2 to Sub-h16

[0239]

[0240]

[0241]

[0242] Synthesis of Sub-j1:

[0243]

[0244] Under a nitrogen atmosphere, 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine (22.66 g, 75 mmol), 3-phenanthroline boric acid (11.10 g, 50 mmol), tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (220 mL), and deionized water (55 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the reaction was carried out at 65-70 °C for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was recrystallized from toluene to give a white solid Sub-j1 (14.62 g, yield 66%).

[0245] Referring to the synthesis of Sub-j1, Sub-j2 and Sub-j6 were synthesized by replacing 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine with reactant L shown in Table 9 and replacing 3-phenanthroline with reactant M.

[0246] Table 9: Synthesis of Sub-j2 and Sub-j6

[0247]

[0248]

[0249] Synthesis of compound 3:

[0250]

[0251] Sub-h1 (15.60 g, 50 mmol), CAS: 2737218-48-1 (27.10 g, 75 mmol), and dry DMF (400 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to -10 °C, and sodium hydrogen (60% content, 2.2 g, 55 mmol) was quickly added. The mixture was stirred overnight. The reaction solution was poured into 500 mL of deionized water, stirred thoroughly for 30 min, filtered, and the filtrate was washed with deionized water until neutral, then rinsed with anhydrous ethanol (200 mL) to obtain the crude product. The crude product was recrystallized from toluene to give a green solid compound 3 (24.85 g, yield 78%), with a mass spectrometry m / z of 638.2 [M+H]. + .

[0252] Referring to the synthesis of compound 3, the compounds of this application in Table 10 were synthesized by replacing reactant N as shown in Table 10 with CAS:2737218-48-1.

[0253] Table 10: Synthesis of the compounds in this application

[0254]

[0255]

[0256] Synthesis of compound 80:

[0257]

[0258] Under a nitrogen atmosphere, Sub-f1 (18.51 g, 36 mmol), CAS: 2568464-79-7 (10.26 g, 30 mmol), tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.42 g, 0.36 mmol), tetrabutylammonium bromide (TBAB, 1.16 g, 3.6 mmol), anhydrous potassium carbonate (9.95 g, 72 mmol), toluene (180 mL), tetrahydrofuran (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 12 hours. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and 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 give a white solid compound 80 (15.60 g, 75% yield), m / z = 695.2 [M+H]. + .

[0259] Referring to the synthesis of compound 80, using reactant O as shown in Table 11 instead of Sub-f1, and reactant P instead of CAS:2568464-79-7, the following compounds of this application were synthesized:

[0260] Table 11: Synthesis of the compounds in this application

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] Synthesis of compound 349:

[0267]

[0268] Under a nitrogen atmosphere, Sub-h1 (15.60 g, 50 mmol), CAS: 1852465-55-4 (20.4 g, 60 mmol), anhydrous potassium carbonate (6.91 g, 50 mmol), toluene (180 mL), dimethylaminopyridine (3.05 g, 25 mmol), and N,N-dimethylacetamide (160 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed at 220 °C for 12 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (100 mL × 3 times). The organic phase was dried over anhydrous magnesium sulfate, filtered, and 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 / ethyl acetate as the mobile phase to give a white solid compound 349 (16.33 g, yield 53%, m / z = 617.2 [M+H]). + .

[0269] Referring to the synthesis of compound 349, using reactant P shown in Table 12 instead of CAS: 1852465-55-4, the following compounds of this application were synthesized:

[0270] Table 12

[0271]

[0272]

[0273] Synthesis of compound 803:

[0274]

[0275] Under a nitrogen atmosphere, Sub-h1 (7.81 g, 25 mmol), CAS: 1419864-64-4 (11.61 g, 27.5 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.46 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-Phos, 0.48 g, 1 mmol), and sodium tert-butoxide (t-Bu) were added sequentially to a 250 mL three-necked flask. ONa (4.8 g, 50 mmol) and xylene (120 mL) were heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water and stirred thoroughly for 30 min. The mixture was then filtered, and the filter cake was washed with deionized water until neutral, and then washed with anhydrous ethanol (200 mL) 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 a white solid (12.10 g; yield 74%).

[0276] Referring to the synthesis of compound 803, using reactant Q shown in Table 13 instead of CAS: 1419864-64-4, the following compounds of this application were synthesized:

[0277] Table 13

[0278]

[0279] NMR of Compound 7: 1 H-NMR(400MHz,CD2Cl2)δppm 8.55-8.50(m,4H),8.14(d,1H),8.08(d,2H),7.98(d,1H),7.90(d,1H),7.86(d,1H),7.81-7.78(m,2H),7.73(d,1H),7.64(d,1H), 7.58(t,1H),7.54-7.47(m,3H),7.42(t,2H),7.36(d,1H),7.24(t,1H),7.19-7.15(m,2H),7.10(d,1H),7.02(t,1H),6.82(d,1H).

[0280] NMR of Compound 730: 1 H-NMR(400MHz,CD2Cl2)δppm 8.16(d,2H),8.02(d,1H),7.90(d,1H),7.74(d,1H),7.66-7.62(m,2H),7.59-7.50(m,6H), 7.44(d,1H),7.39-7.31(m,4H),7.24(t,1H),7.18-7.08(m,5H),7.02(t,1H),6.82(d,1H).

[0281] Fabrication and evaluation of organic electroluminescent devices:

[0282] Example 1: Fabrication of a red organic electroluminescent device

[0283] 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. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0284] PD was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and then α-NPD is vacuum-deposited on the hole injection layer to form a hole injection layer (HIL). The first hole transport layer.

[0285] Compound HT-1 was vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer.

[0286] Next, on the second hole transport layer, compound 3:Ir(Mphq)3 was co-deposited at a deposition rate of 98%:2% to form a layer with a thickness of [missing information]. The red organic light-emitting layer (EML).

[0287] On the organic light-emitting layer, compounds BTB and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition 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.

[0288] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The capping layer (CPL) is then applied to complete the fabrication of the red organic light-emitting device.

[0289] Examples 2-43

[0290] Except that, when fabricating the organic light-emitting layer, the remaining compounds in Table 14 below are used to replace compound 3 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0291] Comparative Examples 1-3

[0292] Except that, when fabricating the organic light-emitting layer, compounds A, B, and C were used instead of compound 3 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0293] The structures of the main materials used in each embodiment and comparative example are as follows:

[0294]

[0295] The performance of the red organic electroluminescent devices prepared in Examples 1-43 and Comparative Examples 1-3 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 14.

[0296] Table 14

[0297]

[0298]

[0299]

[0300] As shown in Table 14, when the compounds of this application are used as the host material of organic electroluminescent devices, compared with Comparative Examples 1 to 3, the device efficiency is improved by at least 10.8% and the lifetime is improved by at least 11.1% when the compounds of this application are used as the host material of red light, while maintaining a low operating voltage.

[0301] Example 44: Red Organic Electroluminescent Device

[0302] 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. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0303] PD was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and then an α-NPD is vacuum-deposited on the hole injection layer to form a layer with a thickness of [missing information]. The first hole transport layer.

[0304] Compound HT-1 was vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The second hole transport layer.

[0305] Next, on the second hole transport layer, RH-N:compound 660:Ir(Mphq)3 was co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0306] On the light-emitting layer, compounds BTB 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.

[0307] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP-1 was used to complete the fabrication of a red organic electroluminescent device.

[0308] Examples 45-56

[0309] Except that, when fabricating the organic light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 44, except that the compounds in Table 15 below were used instead of compound 660 in Example 44.

[0310] Comparative Examples 4-5

[0311] The organic electroluminescent device was prepared using the same method as in Example 44, except that compounds D and E were used instead of compound 660 in Example 44 when fabricating the organic light-emitting layer.

[0312] The structures of the main materials used in Examples 44-56 and Comparative Examples 4-5 are as follows:

[0313]

[0314]

[0315] The performance of the red organic electroluminescent devices prepared in Examples 44-56 and Comparative Examples 4 and 5 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 15.

[0316] Table 15

[0317]

[0318] Referring to Table 15 above, when the compound of the present invention is used as the P-type host in the premix type host material of a red organic electroluminescent device, the luminous efficiency of the device is increased by at least 13.1% and the lifetime is increased by at least 16% while maintaining a low operating voltage.

[0319] The compounds in this application contain a core structure of indole-fused phenothiazine / phenotoxazine. The sulfur or oxygen atoms in the indole-fused phenothiazine / phenotoxazine each possess two lone pairs of electrons, endowing the core structure with excellent hole transport capabilities. When this core structure is linked to an aryl or electron-rich heteroaryl group, the hole transport capability of the compound is enhanced; such compounds are suitable for p-type materials in mixed-type host materials. When this core structure is linked to a nitrogen-containing heteroaryl group with electron transport properties, the compound simultaneously possesses excellent hole and electron transport performance; such compounds are suitable for single-type host materials. Using the compounds of this application as p-type materials in mixed-type host materials and as single-type host materials can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance device luminous efficiency and lifetime.

Claims

1. A nitrogen-containing compound, characterized in that, The nitrogen-containing compound has the structure shown in Formula 1: Where X is selected from S or O; Group A is selected from the structure shown in formula a-1 or the structure shown in formula a-2; HAr is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted spirodifluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or selected from substituted or unsubstituted groups of the following: -# indicates the key connected to L. The bond connected to L3 is indicated; the substituents in HAr may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, alkyl or phenyl with 1 to 4 carbon atoms; Het is selected from triazine, pyrimidinyl, or pyridinyl; L and L3 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; L1 and L2 may be the same or different, and each is independently selected from 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 dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinylene; The substituents in L, L3, L1, and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5 to 20 carbon atoms. Ar3 is selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 20 carbon atoms; Ar4 is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 20 carbon atoms; The substituents in Ar1, Ar2, Ar3 and Ar4 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. Each of R1, R2, and R3 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. Optionally, any two adjacent groups form a benzene ring. n1 represents the number of R1s, which can be selected from 0, 1, 2, 3 or 4; n2 represents the number of R2s, which can be selected from 0, 1, 2 or 3; n3 represents the number of R3s, which can be selected from 0, 1, 2, 3 or 4.

2. The nitrogen-containing compound according to claim 1, wherein, The nitrogen-containing compounds shown in Formula 1 are selected from the structures shown below:

3. The nitrogen-containing compound according to claim 1, wherein, Het is selected from Where -* represents the key connected to L, Indicates the key connected to L1 or L2.

4. The nitrogen-containing compound according to claim 1, wherein, HAr is selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the following groups: -# indicates the key connected to L. Indicates the key connected to L3; The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl, and when the number of substituents is greater than 1, the substituents may be the same or different.

5. The nitrogen-containing compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl.

6. The nitrogen-containing compound according to claim 5, wherein, The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl. Optionally, any two adjacent substituents in Ar1 and Ar2 form a benzene ring.

7. The nitrogen-containing compound according to claim 1, wherein, Ar3 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted quinolinyl.

8. The nitrogen-containing compound according to claim 7, wherein, The substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, or pyridyl. Optionally, any two adjacent substituents in Ar3 form a benzene ring.

9. The nitrogen-containing compound according to claim 1, wherein, Ar4 is selected from single bonds, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

10. The nitrogen-containing compound according to claim 9, wherein, The substituents in Ar4 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthio, dibenzothiophene, dibenzofuranyl, or carbazolyl. Optionally, any two adjacent substituents in Ar4 form a benzene ring.

11. The nitrogen-containing compound according to claim 1, wherein, Each of R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl. Optionally, any two adjacent groups form a benzene ring.

12. The nitrogen-containing compound according to claim 1, wherein, Group A is selected from the group consisting of the following groups:

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

14. 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; characterized in that, The functional layer comprises a nitrogen-containing compound as described in any one of claims 1 to 13.

15. The organic electroluminescent device according to claim 14, characterized in that, The functional layer includes an organic light-emitting layer, which contains the nitrogen-containing compound.

16. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 14 or 15.

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