Nitrogen-containing compounds, organic electroluminescent devices, and electronic devices

Abstract

This application relates to a nitrogen-containing compound and an organic electroluminescent device and electronic apparatus comprising the same. The nitrogen-containing compound of this application comprises a core structure of indole-phenothiazine / phenoxazine fused indole. When this nitrogen-containing compound is used as the host material of an organic electroluminescent device, the luminous efficiency and lifetime of the device can be improved.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to a nitrogen-containing compound 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 electroluminescent devices, such as organic light-emitting diodes (OLEDs), typically include a cathode and an anode arranged 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 most significant challenges in existing organic light-emitting diodes (OLEDs) are lifespan and efficiency. As displays become larger, driving voltages increase, necessitating improvements in both luminous and current efficiency. Therefore, it is essential to continue developing novel materials to further enhance the performance of OLEDs. 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 an organic electroluminescent device and electronic device containing the same, wherein the nitrogen-containing compound used in the organic electroluminescent device can improve the performance of the device.

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

[0006]

[0007] X is selected from S or O;

[0008] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, 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, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0009] And at least one set of adjacent R1, adjacent R2 or adjacent R3 are bonded to each other to form the fused structure shown in Formula 2, where * indicates the position fused with Formula 1;

[0010] Ring M is selected from 6-14 aryl rings;

[0011] Each R4 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, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0012] Groups A1 and A2 are independently selected from the structure shown in Formula a-1 or the structure shown in Formula a-2, and at least one of A1 and A2 is selected from the structure shown in Formula a-1;

[0013] When Equation 1 contains two structures shown in Equation a-1, each L3 may be the same or different, and each Ar3 may be the same or different.

[0014] 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.

[0015] Ar3 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;

[0016] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0017] 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.

[0018] The substituents in L, L1, L2, L3, Ar1, Ar2, and Ar3 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, deuterated alkyl 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, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0019] n1 and n2 are each independently selected from 0, 1, 2, 3 or 4;

[0020] n3 is selected from 0, 1, 2, or 3;

[0021] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0022] 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.

[0023] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0024] The compounds in this application contain a core structure of indole-phenothiazine / phenoxazine fused with indole. The two lone pairs of electrons on the sulfur or oxygen atoms in the indole-phenothiazine / phenoxazine endow the core structure with excellent hole transport capability. Further fusion of indole with indole on the indole-phenothiazine / phenoxazine further enhances the hole transport capability of the core. The applications of the compounds vary depending on the electronic properties of the connecting groups. When the core is connected to an electron-donating aryl or heteroaryl group, it can be used as a hole-transporting material in a hybrid host material; when the core is connected to an electron-deficient nitrogen-containing heteroaryl group, it can be used as a bipolar host material. As host materials, the compounds in this application can improve carrier balance in organic light-emitting layers, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance device luminescence efficiency and lifetime. Attached Figure Description

[0025] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed embodiments to explain this application, but do not constitute a limitation thereof.

[0026] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0027] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0028] Figure Labels

[0029] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0030] 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer.

[0031] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation Plan

[0032] 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 to make the present application more comprehensive and complete, and to 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 the present application.

[0033] In a first aspect, this application provides a nitrogen-containing compound having the structure represented by Formula 1:

[0034]

[0035] X is selected from S or O;

[0036] Each of R1, R2, and R3 may be the same or different, and each is independently selected from hydrogen, 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, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0037] And at least one set of adjacent R1, adjacent R2 or adjacent R3 are bonded to each other to form the fused structure shown in Formula 2, where * indicates the position fused with Formula 1;

[0038] Ring M is selected from 6-14 aryl rings;

[0039] Each R4 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, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0040] Groups A1 and A2 are independently selected from the structure shown in Formula a-1 or the structure shown in Formula a-2, and at least one of A1 and A2 is selected from the structure shown in Formula a-1;

[0041] When Equation 1 contains two structures shown in Equation a-1, each L3 may be the same or different, and each Ar3 may be the same or different.

[0042] 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.

[0043] Ar3 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;

[0044] Het is a nitrogen-containing heteroaryl group with 3 to 20 carbon atoms;

[0045] 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.

[0046] The substituents in L, L1, L2, L3, Ar1, Ar2, and Ar3 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, deuterated alkyl 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, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0047] n1 and n2 are each independently selected from 0, 1, 2, 3 or 4;

[0048] n3 is selected from 0, 1, 2, or 3;

[0049] n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0050] 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 form a saturated or unsaturated 3- to 15-membered ring" means that any two adjacent substituents can connect with each other to form a saturated or unsaturated 3- to 15-membered ring, or any two adjacent substituents 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.

[0051] 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.

[0052] 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, deuterated alkyl, trialkylsilyl, triphenylsilyl, deuterated aryl, haloaryl, alkyl, haloalkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0053] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0054] Unless otherwise stated, the hydrogen atoms in the compound structures of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D) or tritium (T).

[0055] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms in that group and all its substituents. 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.

[0056] 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, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthyl, spirodifluorenyl, etc. Base, etc.

[0057] 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.

[0058] In this application, terphenyl includes

[0059] 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.

[0060] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 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 6-30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-25 carbon atoms; and in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-18 carbon atoms.

[0061] In this application, the fluorene group can be replaced by one or more substituents, wherein any two adjacent substituents can combine with each other to form a substituted or unsubstituted spirocyclic structure. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0062] In this application, the aryl groups used as substituents for L1, L2, L3, L, Ar1, Ar2, and Ar3 are, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, and dimethylfluorenyl.

[0063] 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, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0064] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group 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 group is a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 12-18 carbon atoms; in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5-18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having 5-12 carbon atoms.

[0065] In this application, the heteroaryl groups that serve as substituents for L1, L2, L3, L, Ar1, Ar2, and Ar3 include, but are not limited to, pyridyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0066] 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.

[0067] 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.

[0068] In this application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.

[0069] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl and triethylsilyl.

[0070] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0071] In this application, the cycloalkyl group having 3 to 10 carbon atoms has, for example, 3, 4, 5, 6, 7, 8, or 10 carbon atoms. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0072] 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.

[0073] 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.

[0074] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered aryl group. 6-14-membered aromatic rings refer to aromatic rings with 6 to 14 ring atoms. 3-15-membered rings refer to cyclic groups with 3 to 15 ring atoms. Examples of 3-15-membered rings include cyclopentane, cyclohexane, fluorene rings, and benzene rings.

[0075] In this application, Both "-*" and "-#" refer to the position where they bind to other substituents or binding sites.

[0076] In this application, a non-positioned linker bond refers to a single bond extending from the ring 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.

[0077]

[0078] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0079]

[0080] In this application, a non-orienting 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-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0081]

[0082] In the present application, Het is a nitrogen-containing heteroaryl group having 3 to 20 carbon atoms, and the Het group contains at least one nitrogen atom. In some embodiments, the Het group contains at least two nitrogen atoms.

[0083] In some embodiments, Formula 2 is selected from the following structures:

[0084]

[0085] In some embodiments, any adjacent group of R1 or any adjacent group of R2 are bonded to each other to form a fused structure as shown in Formula 2, and * represents the position where Formula 2 is fused to Ring T or Ring Q in Formula 1.

[0086] In some embodiments, the nitrogen-containing compound is selected from the following structures:

[0087]

[0088]

[0089] In the present application, when both Group A1 and Group A2 are selected from the structures shown in Formula a-1, Ar3 in Group A1 is the same as or different from Ar3 in Group A2, and L3 in Group A1 is the same as or different from L3 in Group A2.

[0090] In some embodiments, Het is selected from the group consisting of the following groups:

[0091]

[0092] -# represents the bond connected to L, represents the bond connected to L1 or L2; only one in the formula represents the one connected at this position In, L2 is a single bond and Ar2 is hydrogen.

[0093] In some more specific embodiments, Het is selected from the group consisting of the following groups:

[0094]

[0095] -# represents the bond connected to L, represents the bond connected to L1; represents the bond connected to L2; there is no in the formula, and represents the one connected at this position In, L2 is a single bond and Ar2 is hydrogen.

[0096] In some embodiments, Ar1 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms and substituted or unsubstituted heteroaryl groups having 12-18 carbon atoms.

[0097] In some embodiments, Ar1 and Ar3 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 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0098] In some embodiments, Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups having 6-25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12-18 carbon atoms.

[0099] In some embodiments, Ar2 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 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0100] In some embodiments, the substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, halogen, cyano, haloalkyl with 1-4 carbon atoms, deuteralkyl with 1-4 carbon atoms, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, and trialkylsilyl with 3-8 carbon atoms. Optionally, any two adjacent substituents form a fluorene ring, a benzene ring, or a naphthalene ring.

[0101] In some embodiments, Ar1 and Ar3 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted spirodifluorenyl.

[0102] Optionally, Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted spirodifluorenyl.

[0103] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl.

[0104] In some specific embodiments, Ar1 and Ar3 are each independently 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:

[0105]

[0106] 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, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzoxazolyl, or benzothiazolyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0107] In some embodiments, L is selected from single bonds and substituted or unsubstituted aryl groups having 6-12 carbon atoms.

[0108] In some embodiments, L1, L2, and L3 are each independently selected from single-bonded substituted or unsubstituted aryl groups with 6-12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5-18 carbon atoms.

[0109] In some embodiments, the substituents in L, L1, L2, and L3 are each independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, deuteryl with 1-4 carbon atoms, aryl with 6-12 carbon atoms, and heteroaryl with 5-12 carbon atoms.

[0110] 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 phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.

[0111] In some embodiments, the substituents in L, L1, L2, and L3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.

[0112] In some embodiments, L, L1, L2, and L3 are each independently selected from single-bonded, substituted, or unsubstituted groups Q, wherein the unsubstituted group Q is selected from the following groups:

[0113]

[0114] The substituted group Q has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, or naphthyl.

[0115] In some specific implementations, L is selected from a single bond or the following groups:

[0116]

[0117] In some specific implementations, L1 and L2 are each independently selected from single bonds or the following groups:

[0118]

[0119] In some specific implementations, L3 is selected from single bonds or the following groups:

[0120]

[0121] In some implementation schemes, Selected from the group consisting of the following groups, Selected from hydrogen or the following groups:

[0122]

[0123]

[0124] In some specific implementation plans, Selected from the group consisting of the following groups, Selected from hydrogen or the following groups:

[0125]

[0126] In some implementations, at least one of A1 and A2 has the structure shown in equation a-1, and the structure shown in equation a-1 Selected from the following groups:

[0127]

[0128]

[0129] In some specific implementation plans, Select the following groups:

[0130]

[0131] In some embodiments, R1, R2, and R3 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl, and at least one set of adjacent R1, adjacent R2, or adjacent R3 are bonded to each other to form the fused ring structure shown in Formula 2;

[0132] In some embodiments, each R4 may be the same or different, and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0133] Optionally, the nitrogen-containing compound is selected from the group consisting of:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] Secondly, 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 contains the nitrogen-containing compound described in the first aspect of this application.

[0146] The nitrogen-containing compounds provided in this application can be used to form at least one organic film layer in a functional layer to improve the device's lifespan and other properties.

[0147] 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.

[0148] Optionally, the functional layer further includes a hole transport layer located between the anode and the organic light-emitting layer.

[0149] In one embodiment, the organic electroluminescent device includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is closer to the anode than the second hole transport layer.

[0150] According to a specific implementation plan, such as Figure 1 As shown, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport 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.

[0151] Optionally, the anode 100 comprises an anode material, preferably one with a high 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.

[0152] In this application, the first hole transport layer 321 and the second hole transport layer 322 may each include one or more hole transport materials. The hole transport layer materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0153]

[0154] In one implementation, the first hole transport layer 321 may be composed of α-NPDs.

[0155] In one implementation, the second hole transport layer 322 is composed of HT-1.

[0156] 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 may be selected from, for example, the following compounds or any combination thereof;

[0157]

[0158] In one embodiment of this application, the hole injection layer 310 is composed of PDs.

[0159] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, or it may 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.

[0160] The main material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials.

[0161] The guest material of the organic light-emitting layer 330 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, 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. For example, specific examples of phosphorescent dopant include, but are not limited to,

[0162]

[0163] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device.

[0164] In one specific embodiment, the host material of the organic light-emitting layer 330 is a nitrogen-containing compound and RH-N (structure shown below) of this application, and the guest material is, for example, RD-1.

[0165] In another specific embodiment, the host material of the organic light-emitting layer 330 is a nitrogen-containing compound of this application, and the guest material is, for example, RD-2.

[0166] 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 LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials; this application does not impose any specific limitations. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0167]

[0168] In one embodiment of this application, the electron transport layer 340 is composed of BmPyPhB and LiQ.

[0169] 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.

[0170] 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 includes ytterbium (Yb).

[0171] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0172] According to one implementation scheme, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 may 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.

[0173] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this disclosure is not limited thereto.

[0174] Synthesis Examples

[0175] Those skilled in the art will recognize that the chemical reactions described in this application can be used to suitably prepare 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 in this application, or making some conventional modifications to the reaction conditions. Compounds synthesized by methods not mentioned in this application are all commercially available starting materials.

[0176] 1. Synthesis of intermediate Sub-aX

[0177] Synthesis of intermediate Sub-a1:

[0178]

[0179] Under a nitrogen atmosphere, RM-1 (CAS: 77801-60-6, 12.08 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-a1 (10.47 g, yield 62%).

[0180] Referring to the synthesis of Sub-a1, reactant A shown in Table 1 was used to replace RM-1 in the synthesis of Sub-a2 to Sub-a9.

[0181] Table 1 Synthesis of Sub-a2 to Sub-a9

[0182]

[0183]

[0184] 2. Synthesis of intermediate Sub-bX

[0185] Synthesis of intermediate Sub-b1:

[0186]

[0187] Under air atmosphere, Sub-a1 (16.89 g, 50 mmol), 2-aminothiophenol (9.39 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 100 °C 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-b1 (9.21 g, yield 42%).

[0188] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b9 were synthesized by replacing Sub-a1 with reactant B shown in Table 2 and replacing 2-aminothiophenol with reactant C.

[0189] Table 2 Synthesis of Sub-b2 to Sub-b9

[0190]

[0191] 3. Synthesis of intermediate Sub-cX

[0192] Synthesis of intermediate Sub-c1:

[0193]

[0194] Under air atmosphere, Sub-c1 (21.95 g, 50 mmol), cuprous bromide (1.43 g, 10 mmol), and DMF (200 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-c1 (14.85 g, yield 68%).

[0195] Referring to the synthesis of Sub-c1, Sub-c2 to Sub-c8 were synthesized by replacing Sub-b1 with reactant D shown in Table 3.

[0196] Table 3 Synthesis of Sub-c2 to Sub-c8

[0197]

[0198]

[0199] 4. Synthesis of intermediate Sub-dX

[0200] Synthesis of Sub-d1:

[0201]

[0202] Under a nitrogen atmosphere, Sub-C4 (18.60 g, 44 mmol), pinacol diborate (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol), and 1,4-dioxane (120 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylacetone)dipalladium (0.40 g, 0.44 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (0.42 g, 0.88 mmol) were quickly added. The mixture was then heated to reflux and 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, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-d1 (16.51 g, yield 73%) was obtained.

[0203] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d7 were synthesized by replacing Sub-c4 with reactant E shown in Table 4.

[0204] Table 4 Synthesis of Sub-d2 to Sub-d7

[0205]

[0206]

[0207] 5. Synthesis of intermediate Sub-eX

[0208] Synthesis of Sub-e1:

[0209]

[0210] Under a nitrogen atmosphere, Sub-d1 (28.28 g, 55 mmol), o-bromonitrobenzene (10.05 g, 50 mmol), tetra(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (280 mL), tetrahydrofuran (70 mL), and deionized water (70 mL) were added sequentially to a 1000 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 (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 as the mobile phase to obtain a pale yellow solid, Sub-e1 (18.58 g, yield 73%).

[0211] Referring to the synthesis of Sub-e1, Sub-e2 to Sub-e12 were synthesized by replacing Sub-d1 with reactant F shown in Table 5 and replacing o-bromonitrobenzene with reactant G.

[0212] Table 5 Synthesis of Sub-e2 to Sub-e12

[0213]

[0214]

[0215] 6. Synthesis of intermediate Sub-fX

[0216] Synthesis of Sub-f1:

[0217]

[0218] Under a nitrogen atmosphere, Sub-e1 (25.45 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol), and o-dichlorobenzene (250 mL) were added 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 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 gray-green solid, Sub-f1 (16.87 g, 68% yield).

[0219] Referring to the synthesis of Sub-f1, Sub-f2 to Sub-f12 were synthesized by replacing Sub-e1 with reactant H shown in Table 6.

[0220] Table 6 Synthesis of Sub-f2 to Sub-f12

[0221]

[0222]

[0223] 7. Synthesis of intermediate Sub-gX

[0224] Synthesis of Sub-g1:

[0225]

[0226] Under a nitrogen atmosphere, Sub-c5 (21.15 g, 50 mmol), o-chloroaniline (6.38 g, 50 mmol), tris(dibenzylacetone)dipalladium (0.916 g, 1 mmol), 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (220 mL) 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, it 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 a gray-green solid Sub-g1 (13.62 g, yield 53%).

[0227] Referring to the synthesis of Sub-g1, Sub-g2 to Sub-g9 were synthesized by replacing Sub-c5 with reactant J and o-chloroaniline with reactant K as shown in Table 7.

[0228] Table 7 Synthesis of Sub-g2 to Sub-g9

[0229]

[0230]

[0231] 8. Synthesis of intermediate Sub-hX

[0232] Synthesis of Sub-h1:

[0233]

[0234] Under a nitrogen atmosphere, Sub-g1 (25.70 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol), and N,N-dimethylacetamide (260 mL) 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, it 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 a gray-green solid Sub-h1 (10.27 g; yield 45%).

[0235] Referring to the synthesis of Sub-h1, Sub-h2 to Sub-h9 were synthesized by replacing Sub-g1 with reactant L shown in Table 8.

[0236] Table 8 Synthesis of Sub-h2 to Sub-h9

[0237]

[0238]

[0239] 9. Synthesis of intermediate Sub-jX

[0240] Synthesis of Sub-j1:

[0241]

[0242] Under a nitrogen atmosphere, Sub-f3 (24.58 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol), and N,N-dimethylformamide (250 mL) 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, filtered, and the filter cake was collected. The filter cake was dissolved in dichloromethane 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 a gray-green solid, Sub-j1 (18.45 g, yield 65%).

[0243] Referring to the synthesis of Sub-j1, Sub-j2 to Sub-j9 were synthesized by replacing Sub-f3 with reactant M shown in Table 9.

[0244] Table 9 Synthesis of Sub-j2 to Sub-j9

[0245]

[0246]

[0247] 10. Synthesis of intermediate Sub-kX

[0248] Synthesis of Sub-k1:

[0249]

[0250] Under a nitrogen atmosphere, Sub-j1 (28.38 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 precipitate 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 gray-green solid, Sub-j1 (20.05 g, yield 84%).

[0251] Referring to the synthesis of Sub-k1, Sub-k2 to Sub-k9 were synthesized by replacing Sub-j1 with reactant N as shown in Table 10.

[0252] Table 10 Synthesis of Sub-k2 to Sub-k9

[0253]

[0254]

[0255] 11. Synthesis of Compounds

[0256] Synthesis of compound A-3:

[0257]

[0258] Under a nitrogen atmosphere, Sub-f1 (11.94 g, 25 mmol), reactant CAS: 142475-00-1 (6.66 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.5 mmol), 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 0.41 g, 1 mmol), sodium tert-butoxide (t-BuONa, 4.80 g, 50 mmol), and xylene (120 mmol) were added sequentially to a 250 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 250 mL of deionized water and stirred thoroughly for 30 min. The mixture was then filtered, and the filter cake was rinsed with deionized water until neutral, followed by rinsing with 100 mL of anhydrous ethanol 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 compound A-3 as a white solid (10.22 g, yield 64%, m / z = 639.2 [M+H]). + ).

[0259] Referring to the synthesis of compound A-3, reactant O was used instead of Sub-f1, and reactant P was used instead of reactant CAS:142475-00-1 as shown in Table 11, to synthesize the compounds of this application in Table 11.

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

[0261]

[0262]

[0263]

[0264]

[0265] Synthesis of compound B-8:

[0266]

[0267] Sub-k3 (23.88 g, 50 mmol), reactant CAS: 2737218-48-1 (27.14 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 hydride (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, it was rinsed 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 compound B-8 (32.12 g, yield 80%; m / z = 803.2 [M+H]) as a yellow-green solid. + ).

[0268] Referring to the synthesis of compound B-8, reactant Q was used instead of Sub-k3, and reactant R was used instead of reactant CAS:2737218-48-1, as shown in Table 12, to synthesize the compounds of this application in Table 12.

[0269] Table 12 Synthesis of the compounds in this application

[0270]

[0271]

[0272] Synthesis of compound B-85:

[0273]

[0274] Under a nitrogen atmosphere, Sub-f2 (14.33 g, 30 mmol), CAS: 124959-44-0 (9.59 g, 33 mmol), anhydrous potassium carbonate (4.15 g, 30 mmol), 4-dimethylaminopyridine (1.83 g, 15 mmol), and N,N-dimethylacetamide (150 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and reacted for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, 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 obtain compound B-85 (13.83 g, yield 63%; m / z [M+H)) as a white solid. + =733.2).

[0275] Referring to the synthesis of compound B-85, reactant S was used instead of Sub-f2, and reactant T was used instead of reactant CAS:24959-44-0, as shown in Table 13, to synthesize the compounds of this application in Table 13.

[0276] Table 13 Synthesis of the compounds in this application

[0277]

[0278]

[0279] The NMR data of the compounds are shown in Table 14 below.

[0280] Table 14

[0281]

[0282]

[0283] Fabrication and evaluation of organic electroluminescent devices:

[0284] Example 1: Fabrication of a red organic electroluminescent device

[0285] 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.

[0286] 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.

[0287] 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.

[0288] Next, on the second hole transport layer, RH-N:compound A-3:RD-1 were co-deposited at a deposition rate of 49%:49%:2% to form a layer with a thickness of [missing information]. Organic light-emitting layer (red light-emitting layer, R-EML).

[0289] On the organic light-emitting layer, compounds BmPyPhB 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.

[0290] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The coating layer is used to complete the fabrication of the red organic electroluminescent device.

[0291] Examples 2-27

[0292] Except that, when fabricating the organic light-emitting layer, the compound AX in Table 15 is used instead of compound A-3 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0293] Comparative Examples 1-4

[0294] Except that, when fabricating the organic light-emitting layer, compounds A, B, C, and D were used instead of compound A-3 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0295] The compounds used in preparing the various examples and comparative examples have the following structures:

[0296]

[0297]

[0298] The performance of the red organic electroluminescent devices prepared in Examples 1-27 and Comparative Examples 1-4 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.

[0299] Table 15

[0300]

[0301]

[0302] As shown in Table 15, when the nitrogen-containing compound of this application is used as the hole transport host material in the hybrid host material of the red organic electroluminescent device, the luminous efficiency of the device is improved by at least 14.6% and the lifetime is improved by at least 12.7%.

[0303] Example 28: Red Organic Electroluminescent Device

[0304] 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.

[0305] 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 thickness of [missing information]. The first hole transport layer.

[0306] 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.

[0307] Next, on the second hole transport layer, compound B-8:RD-2 was co-deposited at a deposition rate of 98%:2% to form a layer with a thickness of [missing information]. Organic light-emitting layer (red light-emitting layer, R-EML).

[0308] On the organic light-emitting layer, compounds BmPyPhB 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.

[0309] 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.

[0310] Examples 29-40

[0311] The organic electroluminescent device was prepared using the same method as in Example 28, except that the compound BY in Table 16 was used instead of compound B-8 in Example 28 when fabricating the organic light-emitting layer.

[0312] Comparative Examples 5-7

[0313] Except that, when fabricating the organic light-emitting layer, compounds E, F, and G were used instead of compound B-8 in Example 28, the organic electroluminescent device was prepared using the same method as in Example 28.

[0314]

[0315] The performance of the red organic electroluminescent devices prepared in Examples 28-40 and Comparative Examples 5-7 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. 2The test was conducted under the specified conditions, and the test results are shown in Table 16.

[0316] Table 16

[0317]

[0318] As shown in Table 16, when the nitrogen-containing compound of this application is used as the bipolar host material of the red organic electroluminescent device, the efficiency and lifetime are improved by at least 10.5% and 11.1%, respectively.

[0319] In summary, using the compounds of this application as the host material of the organic light-emitting layer can improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0320] The preferred embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

[0321] It should also be noted that the specific technical features described in the above specific implementation schemes can be combined in any suitable way without contradiction. In order to avoid unnecessary repetition, this application will not describe the various possible combinations separately.

Claims

1. A nitrogen-containing compound characterized in that, The nitrogen-containing compound has a structure represented by Formula 1: X is selected from S; each R1, R2, and R3 is the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, or tert-butyl; each R4 is the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, or tert-butyl; any one group of adjacent R1 or any one group of adjacent R2 is bonded to each other to form a fused structure represented by Formula 2, * represents the position at which Formula 2 is fused with ring T or ring Q in Formula 1; the structure of Formula 2 is selected from the structures represented by 2-1 to 2-4: groups A1 and A2 are each independently selected from the structure represented by Formula a-1 or the structure represented by Formula a-2, and at least one of A1 and A2 is selected from the structure represented by Formula a-1; when the formula 1 contains two structures represented by the formula a-1, each L3 is the same or different, and each Ar3 is the same or different; Het is selected from the group consisting of: - # represents a bond to L, represents a bond to L1or L2; only one of the formulae of the formulae represents the bond to the position L2is a single bond and Ar2is hydrogen; Ar1 and Ar3 are each independently selected from a substituted or unsubstituted group V; Ar2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups: the substituted group V has one or two or more substituents, the substituents of group V are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl, or benzothiazolyl, and when the number of substituents on group V is greater than 1, the substituents are the same or different; L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group; L1, L2, and L3 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group; the substituents in L, L1, L2, and L3 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, or phenyl; n1 and n2 are each independently selected from 0, 1, 2, 3, or 4; n3 is selected from 0, 1, 2, or 3; n4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

2. The nitrogen-containing compound of claim 1, wherein, at least one of A1and A2is a structure of formula a-1, and the structure of formula a-1 is selected from the group consisting of 3. The nitrogen-containing compound of claim 1, wherein, is selected from the group consisting of is selected from the group consisting of hydrogen or 4. The nitrogenous compound of claim 1, wherein, The nitrogen-containing compound is selected from the group consisting of the following compounds:

5. An organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; characterized in that, The functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, characterized in that The functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the nitrogen-containing compound.

7. An electronic device, comprising: The organic electroluminescent device according to claim 5 or 6.

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