Nitrogen-containing compounds, and organic electroluminescent devices and electronic devices comprising the same

Abstract

The application provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device containing the same, and belongs to the technical field of organic electroluminescence. The nitrogen-containing compound has a fused heteroaromatic ring as a hole transport group and a nitrogen-containing heteroaryl group as an electron transport group, is suitable for use in an organic electroluminescent device, and can significantly improve the performance of the organic electroluminescent device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), as a new generation of display technology, have advantages such as ultra-thinness, self-illumination, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. They have been widely used in industries such as flat panel displays, flexible displays, solid-state lighting, and automotive displays.

[0003] Organic light emission (OLED) refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic material layer between them. This organic material layer is usually formed as a multilayer structure composed of different materials to improve the brightness, efficiency, and lifespan of the OLED. The organic material layer can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the OLED structure, when a voltage is applied between the two electrodes, holes and electrons are injected into the organic material layer from the anode and cathode, respectively. When the injected holes meet the electrons, excitons are formed, and light is emitted when these excitons return to their ground state. The most significant challenges in existing OLEDs are lifespan and efficiency. With the increasing size of displays, the driving voltage also increases, requiring improvements in luminous efficiency and power efficiency while maintaining a certain lifespan. Therefore, organic materials must address these efficiency and lifespan issues, necessitating the continuous development of new, high-efficiency, long-life materials suitable for mass production in OLEDs.

[0004] It should be noted that the information disclosed in the background section above is only used to enhance the understanding of the background of this application, and therefore may include information that does not constitute prior art known to those skilled in the art. Summary of the Invention

[0005] The purpose of this application is to overcome the shortcomings of the prior art and provide a nitrogen-containing compound and an organic electroluminescent device and electronic device containing the same, which can improve luminous efficiency and extend device life.

[0006] To achieve the above-mentioned objectives, this application adopts the following technical solution:

[0007] According to a first aspect of this application, a nitrogen-containing compound is provided, the general structural formula of which is shown in Formula 1:

[0008] The nitrogen-containing compound has the structure shown in Formula 1:

[0009]

[0010] Where * represents a connection site. Represents chemical bonds,

[0011] Ring A, ring B, and ring C are each independently selected from aromatic rings with 6-14 carbon atoms, and none of the three are simultaneously benzene rings;

[0012] Formula II is fused to any two adjacent carbon atoms of ring B in Formula I via the bonds shown in *.

[0013] U1 and U2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, the structure shown in Formula III or the structure shown in Formula IV, and at least one of U1 and U2 is selected from Formula III or Formula IV.

[0014]

[0015] X is selected from S or O;

[0016] X1, X2, and X3 may be the same or different, and are independently selected from N or C(R), and at least one of X1, X2, and X3 is N;

[0017] Each R, R1, R2, R3, R4, and R5 is independently selected from hydrogen, deuterium, halogen group, cyano, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, deuterated alkyl with 1-5 carbon atoms, trialkylsilyl with 3-12 carbon atoms, or cycloalkyl with 3-10 carbon atoms;

[0018] n1 represents the number of substituents R1, and n1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. Optionally, any two adjacent R1s form a ring.

[0019] n2 represents the number of substituents R2, and n2 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n2 is greater than 1, any two R2s are the same or different. Optionally, any two adjacent R2s form a ring.

[0020] n3 represents the number of substituents R3, and n3 is selected from 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different. Optionally, any two adjacent R3s form a ring.

[0021] n4 represents the number of substituents R4, which is selected from 1, 2 or 3. When n4 is greater than 1, any two R4s are the same or different. Optionally, any two adjacent R4s form a ring.

[0022] n5 represents the number of substituents R5, which is selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. Optionally, any two adjacent R5s form a ring.

[0023] L, L1, L2, L3 and L4 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0024] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms respectively;

[0025] The substituents in U1, U2, L, L1, L2, L3, L4, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuteryl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, or alkoxy with 1-10 carbon atoms;

[0026] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0027] The nitrogen-containing compounds provided in this application utilize an indole-carbazole fused aromatic ring parent structure, giving the compounds excellent hole injection and transport characteristics. The combination of triazine groups and benzimidazole further enhances the electron transport and injection capabilities. The resulting nitrogen-containing compounds exhibit LUMO level electron cloud and HOMO level orbital separation, broadening the carrier recombination region and improving luminescence. These nitrogen-containing compounds maintain a high T1 (triple-state) value while possessing balanced hole and electron transport capabilities, making them suitable as host materials for the emissive layer in OLED devices. When these compounds are used as emissive layer materials in organic electroluminescent devices, they will effectively improve the device's electron transport performance, thereby enhancing the balance between hole and electron injection, improving device luminous efficiency, and extending device lifespan.

[0028] 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 at least one functional layer between the anode and the cathode, the functional layer comprising the aforementioned nitrogen-containing compound.

[0029] According to a third aspect of this application, an electronic device is provided, including the aforementioned organic electroluminescent device.

[0030] It should be understood that the above general description and the following detailed description are exemplary and explanatory only, and do not limit this application. Attached Figure Description

[0031] 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.

[0032] In the attached diagram:

[0033] Figure 1 This is a schematic diagram of one embodiment of the organic electroluminescent device of this application.

[0034] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0035] Explanation of reference numerals in the attached figures

[0036] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 320, First hole transport layer; 330, Second hole transport layer; 340, Organic electroluminescent layer; 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device. Detailed Implementation

[0037] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0038] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0039] The described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. Numerous specific details are provided in the following description to give a full understanding of embodiments of this application. However, those skilled in the art will recognize that the technical solutions of this application can be practiced without one or more of the specific details described, or other methods, components, materials, etc., can be employed. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical concept of this application.

[0040] This application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0041]

[0042] Where * represents a connection site. Represents chemical bonds,

[0043] Rings A, B, and C are each independently selected from aromatic rings with 6-14 carbon atoms, and none of them are simultaneously benzene rings; Formula II is fused to any two adjacent carbon atoms of ring B in Formula I by the bonds shown in *.

[0044] U1 and U2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, the structure shown in Formula III or the structure shown in Formula IV, and at least one of U1 and U2 is selected from Formula III or Formula IV.

[0045]

[0046] X is selected from S or O;

[0047] X1, X2, and X3 may be the same or different, and are independently selected from N or C(R), and at least one of X1, X2, and X3 is N;

[0048] Each R, R1, R2, R3, R4, and R5 is independently selected from hydrogen, deuterium, halogen group, cyano, aryl with 6-12 carbon atoms, heteroaryl with 5-12 carbon atoms, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, deuterated alkyl with 1-5 carbon atoms, trialkylsilyl with 3-12 carbon atoms, or cycloalkyl with 3-10 carbon atoms;

[0049] n1 represents the number of substituents R1, and n1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. Optionally, any two adjacent R1s form a ring.

[0050] n2 represents the number of substituents R2, and n2 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n2 is greater than 1, any two R2s are the same or different. Optionally, any two adjacent R2s form a ring.

[0051] n3 represents the number of substituents R3, and n3 is selected from 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different. Optionally, any two adjacent R3s form a ring.

[0052] n4 represents the number of substituents R4, which is selected from 1, 2 or 3. When n4 is greater than 1, any two R4s are the same or different. Optionally, any two adjacent R4s form a ring.

[0053] n5 represents the number of substituents R5, which is selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s are the same or different. Optionally, any two adjacent R5s form a ring.

[0054] L, L1, L2, L3 and L4 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0055] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms respectively;

[0056] The substituents in U1, U2, L, L1, L2, L3, L4, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, heteroaryl with 3-20 carbon atoms, aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuteryl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, or alkoxy with 1-10 carbon atoms;

[0057] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0058] In some embodiments of this application, the nitrogen-containing compound has the following structure:

[0059]

[0060]

[0061] In this application, the descriptive terms "each independently selected from" and "separately independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0062] 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 substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group with 3-20 carbon atoms, an aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an alkyl group with 1-10 carbon atoms, a haloalkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, or an alkoxy group with 1-10 carbon atoms. In this application, the “substituted” functional group can be substituted by one or more of the substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a spiro ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc can exist independently or be fused with the functional group to which they are attached to form a ring.

[0063] In this application, the terms "optional" or "optionally" mean that the event described below may or may not occur, and the description includes the possibility that the event may or may not occur. For example, "optionally, two adjacent substituents ×× form a ring" means that the two substituents may form a ring but are not required to do so, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0064] In this application, the phrase "any two adjacent substituents forming a ring" can include two substituents on the same atom, or one substituent on each of two adjacent atoms. When two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to. When one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring. For example, when Ar1 has two or more substituents, and any two adjacent substituents form a ring, the resulting ring can be a saturated or unsaturated membered ring with 5-13 carbon atoms, such as benzene rings, naphthalene rings, fluorene rings, cyclopentane, cyclohexane, adamantane, etc.

[0065] In this application, "two or more" means two or more.

[0066] In this application, "optionally, any two adjacent R1s form a ring" means that any two adjacent R1s may connect to form a ring or not. For example, when two adjacent R1s form a ring, the number of carbon atoms in the ring can be 6-14, and the ring can be saturated or partially unsaturated; for example, benzene rings, naphthalene rings, indene rings, phenanthrene rings, etc., but not limited to these. "Optionally, any two adjacent R2s form a ring," "optionally, any two adjacent R3s form a ring," "optionally, any two adjacent R4s form a ring," and "optionally, any two adjacent R5s form a ring" have the same meaning and will not be elaborated further.

[0067] 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 L is selected from a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12. For example: Ar1 is... Therefore, its carbon number is 7; L is It has 12 carbon atoms.

[0068] In this application, unless otherwise defined, “heterogeneous” means that a functional group includes at least one heteroatom such as B, N, O, S, P, Si or Se and the remaining atoms are carbon and hydrogen.

[0069] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group may have 1 to 10 carbon atoms, and in this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Furthermore, alkyl groups may be substituted or unsubstituted.

[0070] Preferably, the alkyl group is selected from alkyl groups having 1-5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.

[0071] In this application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused-ring structures. A cycloalkyl group may have 3 to 10 carbon atoms, and numerical ranges such as "3 to 10" refer to integers within a given range; examples of cycloalkyl groups with 3 to 10 carbon atoms include cyclopentyl, cyclohexyl, and adamantyl.

[0072] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring (i.e., an aromatic 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. For example, in this application, biphenyl, terphenyl, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Base, etc.

[0073] The "substituted or unsubstituted aryl group" in this application can contain 6-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6-25; in others, it can be 6-20; in still others, it can be 6-15; and in yet another embodiment, it can be 6-12. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25, or 30. Of course, the number of carbon atoms can also be other numbers, which will not be listed here. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0074] In this application, the term arylene refers to a monovalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0075] In this application, the substituted aryl group may be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and its substituents is 18.

[0076] In this application, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. Specific examples include, but are not limited to, the following structures:

[0077]

[0078] In this application, aryl groups that are substituents in U1, U2, L, L1, L2, L3, L4, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, dimethylfluorenyl, biphenyl, etc.

[0079] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms, wherein the heteroatoms can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic 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, benzothiazolyl, phenothiazinyl, silylfluorenyl, dibenzofuranyl, N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. Among them, thienyl, furanyl, and phenanthroline are heteroaryl groups of the single aromatic ring type, while N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of the polycyclic system type connected by carbon-carbon bonds.

[0080] The "substituted or unsubstituted heteroaryl group" of this application may contain 3-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3-25; in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 5-25; in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 5-18; and in still other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 5-12. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25, or 30. Of course, the number of carbon atoms may also be other numbers, which will not be listed here.

[0081] In this application, the term "heteroaryl" refers to a monovalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0082] 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, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, 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.

[0083] In this application, the heteroaryl groups that serve as substituents in U1, U2, L, L1, L2, L3, L4, Ar1, and Ar2 include, but are not limited to, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and quinolinyl.

[0084] In this application, halogen groups may include fluorine, iodine, bromine, chlorine, etc.

[0085] In this application, specific examples of trialkylsilyl groups having 3-12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0086] In this application, specific examples of haloalkyl groups having 1-10 carbon atoms include, but are not limited to, trifluoromethyl.

[0087] In this application, specific examples of deuterated alkyl groups having 1-10 carbon atoms include, but are not limited to, trideuterated methyl groups.

[0088] In this application, "q-membered ring" refers to the number of ring atoms in a cyclic group, that is, the cyclic group is a ring composed of q atoms. For example, benzene is a 6-membered ring, fluorene is a 13-membered ring, and adamantane is a 10-membered ring.

[0089] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0090] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule by two non-positional linkages that span the bicyclic ring, which means that any possible connection mode is shown as in equations (f-1) to (f-10).

[0091]

[0092] For another example, as shown in the following formula (X'), the fluorene 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. The meaning of this includes any possible connection mode shown in formulas (X'-1) to (X'-5).

[0093]

[0094] 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 the following formula (Y'), the substituent R group represented by formula (Y') is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in formulas (Y'-1) to (Y'-7).

[0095]

[0096] The meaning of non-positioned joins or non-positioned replacements in the following text is the same as here, and will not be repeated hereafter.

[0097] In some embodiments of this application, X1, X2, and X3 are all N.

[0098] In some embodiments of this application, R is hydrogen.

[0099] In some embodiments of this application, X1, X2, and X3 are N and X3 is C(H); or X1, X3 are N and X2 is C(H); or X2, X3 are N and X1 is C(H).

[0100] In some embodiments of this application, ring A and ring C are each independently selected from benzene ring, naphthalene ring, anthracene ring or phenanthrene ring; ring B is selected from benzene ring, naphthalene ring or anthracene ring, and one of ring A, ring B and ring C must not be a benzene ring.

[0101] Optionally, one or both of rings A, B, and C are benzene rings.

[0102] In some embodiments of this application, ring A is a naphthalene ring, and rings B and C are benzene rings; or ring B is a naphthalene ring, and rings A and C are benzene rings; or ring C is a naphthalene ring, and rings B and A are benzene rings.

[0103] In some embodiments of this application, ring A and ring C are each independently selected from... Ring B is selected from

[0104] In some embodiments of this application, ring A is selected from... Ring B is selected from Ring C is selected from

[0105] In some embodiments of this application, ring A is selected from... Ring B is selected from Ring C is selected from

[0106] In some embodiments of this application, L, L1, L2, L3, and L4 are independently selected from single bonds, substituted or unsubstituted aryl groups with 6-15 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-12 carbon atoms.

[0107] Optionally, the substituents in L, L1, L2, L3, and L4 are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, deuterated alkyl groups with 1-5 carbon atoms, haloalkyl groups with 1-5 carbon atoms, or phenyl groups.

[0108] In some embodiments of this application, L, L1, L2, L3, and L4 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted carbazolylene, and substituted or unsubstituted pyridylene.

[0109] Optionally, the substituents in L, L1, L2, L3, and L4 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, or phenyl.

[0110] In some embodiments of this application, L, L1, L2, L3, and L4 are each independently selected from single-bonded, substituted, or unsubstituted groups V; wherein, the unsubstituted group V is selected from the group consisting of:

[0111]

[0112] in, It represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or phenyl; when the number of substituents on the substituted group V is greater than 1, the substituents may be the same or different.

[0113] In some embodiments of this application, L is selected from single bonds, phenylene, or naphthylene.

[0114] In some embodiments of this application, L3 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuranyl.

[0115] Optionally, the substituents in L3 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0116] In some specific embodiments of this application, L, L1, L2, L3, and L4 are each independently selected from the group consisting of single bonds or the following groups:

[0117]

[0118]

[0119] In some embodiments of this application, Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms and substituted or unsubstituted heteroaryl groups with 5-18 carbon atoms. Specifically, Ar1 and Ar2 can be independently selected from: substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms and substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms.

[0120] Optionally, the substituents in Ar1 and Ar2 are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, aryl groups with 6-12 carbon atoms, haloalkyl groups with 1-5 carbon atoms, deuteralkyl groups with 1-5 carbon atoms, or trialkylsilyl groups with 3-6 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.

[0121] In some embodiments of this application, Ar1 and Ar2 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyreneyl, and substituted or unsubstituted quinolinyl.

[0122] Optionally, the substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, trifluoromethyl, trideuterated methyl, or trimethylsilyl; optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

[0123] In some embodiments of this application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W; wherein, the unsubstituted group W is selected from the group consisting of:

[0124]

[0125] in, The substituted group W represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, trifluoromethyl or trimethylsilyl; when the number of substituents on the substituted group W is greater than 1, the substituents may be the same or different.

[0126] In other embodiments of this application, Ar2 is selected from phenyl.

[0127] In some embodiments of this application, Ar1 and Ar2 are each independently selected from the group consisting of:

[0128]

[0129] In some embodiments of this application, either U1 or U2 is selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms or substituted or unsubstituted heteroaryl groups with 5-18 carbon atoms, and the other is selected from the structure shown in Formula III or IV. Specifically, either U1 or U2 is selected from: substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms or substituted or unsubstituted heteroaryl groups with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms; and the other is selected from the structure shown in Formula III or IV.

[0130] Optionally, the substituents in U1 and U2 are independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, alkyl groups with 1-5 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, haloalkyl groups with 1-5 carbon atoms, deuteralkyl groups with 1-5 carbon atoms, or trialkylsilyl groups with 3-6 carbon atoms.

[0131] In some embodiments of this application, either U1 or U2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyreneyl, and the other is selected from the structure shown in Formula III or IV.

[0132] Optionally, the substituents in U1 and U2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, cyclopentyl, cyclohexyl, adamantyl, trifluoromethyl, trideuterated methyl or trimethylsilyl.

[0133] In some specific embodiments of this application, either U1 or U2 is selected from the group represented by Formula III or Formula IV, and the other is selected from the group consisting of:

[0134]

[0135] In this application, formula III may be selected from the group consisting of the following structures:

[0136]

[0137] In some embodiments of this application, the structure shown in Formula III is selected from the group consisting of:

[0138]

[0139]

[0140] The structure shown in Formula IV is selected from the group consisting of the following groups:

[0141]

[0142] In Formulas III and IV, each of R4 and R5 is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or trifluoromethyl.

[0143] In some embodiments of this application, the structure represented by Formula III or IV is selected from the group consisting of:

[0144]

[0145]

[0146] In one embodiment of this application, each of R, R1, R2, R3, R4, and R5 is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, pyridyl, trifluoromethyl, and biphenyl.

[0147] Optionally, any two adjacent R4 groups form a benzene ring;

[0148] Optionally, any two adjacent R5s can form a benzene ring.

[0149] Optionally, each of R, R1, and R3 is hydrogen; any two adjacent R4s form a benzene ring or any two adjacent R5s form a benzene ring.

[0150] Alternatively, the nitrogen-containing compound is selected from the group consisting of:

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] This application also provides an organic electroluminescent device, which includes an anode and a cathode disposed opposite to each other, and at least one functional layer between the anode and the cathode, the functional layer containing the nitrogen-containing compound of this application.

[0178] Optionally, the functional layer includes an organic electroluminescent layer, which includes the nitrogen-containing compound.

[0179] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device.

[0180] In another embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device.

[0181] In one specific embodiment of this application, such as Figure 1 As shown, the organic electroluminescent device of this application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer. The functional layer 300 includes a hole injection layer 310, a first hole transport layer 320, a second hole transport layer (hole auxiliary layer) 330, an organic electroluminescent layer 340, an electron transport layer 350, and an electron injection layer 360, which are sequentially stacked. The organic electroluminescent layer 340 may contain the nitrogen-containing compound described in the first aspect of this application.

[0182] 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.

[0183] Optionally, the first hole transport layer 320 may include one or more hole transport materials. These materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any specific limitations on this. In one embodiment of this application, the first hole transport layer 320 is composed of NPB.

[0184] Optionally, the hole assist layer 330 may include one or more hole transport materials. The hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. In one embodiment of this application, the hole assist layer 330 is composed of HT-04 or TH-05.

[0185] Optionally, the organic electroluminescent layer 340 may be composed of a single luminescent material, or it may include a host material and a guest material. Optionally, the organic electroluminescent layer 340 is composed of a host material and a guest material. Holes and electrons injected into the organic electroluminescent layer 340 can recombine in the organic electroluminescent layer 340 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.

[0186] The guest material of the organic electroluminescent layer 340 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, and this application does not impose any special restrictions on this.

[0187] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device, and the host material of the organic electroluminescent layer 340 includes the nitrogen-containing compound of this application, and the guest material is Ir(3mppy)3.

[0188] In another 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 electroluminescent layer 340 is a nitrogen-containing compound of this application. In another specific embodiment, the host material of the organic electroluminescent layer 340 includes the nitrogen-containing compound of this application and other p-type host materials, such as RHp1 (structure shown below). The guest material can be, for example, Ir(piq)2(acac).

[0189] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any special limitations on them. In one embodiment of this application, the electron transport layer 350 can be composed of ET-03 (structure shown below) and LiQ, or composed of ET-01 (structure shown below) and LiQ.

[0190] Optionally, the cathode 200 comprises a cathode material having a small work function that 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. Preferably, a metal electrode comprising silver and magnesium is included as the cathode.

[0191] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may 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. In one embodiment of this application, the hole injection layer 310 may be composed of PtPC or F4-TCNQ.

[0192] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 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 360 may include ytterbium (Yb).

[0193] This application also provides an electronic device that includes the organic electroluminescent device described in this application.

[0194] For example, such as Figure 2 As shown, the electronic device provided in this application is electronic device 400, which includes any of the organic electroluminescent devices described in the above-described embodiments. This electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. Since electronic device 400 has the aforementioned organic electroluminescent devices, it has the same beneficial effects, which will not be repeated here.

[0195] The present application will now be described in detail with reference to embodiments. However, the following description is intended to explain the present application and not to limit the scope of the present application in any way.

[0196] Synthesis Examples

[0197] Those skilled in the art will recognize that the chemical reactions described in this application can be suitably used to prepare many other 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. Additionally, the synthesis of anti-compounds disclosed in this application...

[0198] (1) Synthesis of intermediate M-1

[0199]

[0200] Nitrogen gas (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, 2-bromo-6-nitrophenol (50.0 g, 229.3 mmol), benzyl alcohol (29.76 g, 275.2 mmol), 1,1'-bis(diphenylphosphine)ferrocene (3.71 g, 6.8 mmol), and xylene (500 mL) were added sequentially. Stirring and heating were started, and the mixture was refluxed for 36 h at 125-135 °C. After the reaction was complete, stirring and heating were stopped, and the reaction was allowed to cool to room temperature before processing. Toluene and water were added to extract the reaction solution. The organic phases were combined, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain solid intermediate M-1 (40.23 g, yield 64%).

[0201] By replacing 2-bromo-6-nitrophenol with 3-bromo-6-nitrophenol, 3-bromo-2-nitrophenol, or 4-bromo-2-nitrophenol, intermediates M-2, M-3, and M-4, as shown below, can be prepared using the same method.

[0202]

[0203] (2) Synthesis of intermediates N-1 to N-8

[0204] (2-1) Synthesis of intermediate N-1

[0205]

[0206] Nitrogen gas (0.100 L / min) was bubbled into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, M-1 (50.0 g, 182.40 mmol), m-chlorophenylboronic acid (31.37 g, 200.64 mmol), potassium carbonate (55.5 g, 401.3 mmol), tetra(triphenylphosphine)palladium (4.2 g, 3.6 mmol), and tetrabutylammonium bromide (1.2 g, 3.6 mmol) were added, along with a mixed solvent of toluene (400 mL), ethanol (200 mL), and water (100 mL). The mixture was stirred and heated until it reached 75-80 °C. The mixture was then refluxed for 8 h. After the reaction was complete, the mixture was cooled to room temperature. The organic phase was separated by extraction with toluene and water, washed with water until neutral, dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain solid intermediate N-1 (39.6 g, yield 71%).

[0207] By replacing m-chlorophenylboronic acid with p-chlorophenylboronic acid or 4-chloronaphthaleneboronic acid, N-2 and N-3 can be prepared using the same method.

[0208]

[0209] (2-2) Synthesis of intermediate N-4

[0210]

[0211] Nitrogen gas (0.100 L / min) was bubbled into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, 2,5-dichlorobenzoxazole (35.0 g, 186.1 mmol), 2-naphthylboronic acid (32.0 g, 186.1 mmol), potassium carbonate (64.3 g, 465.4 mmol), tetra(triphenylphosphine)palladium (4.3 g, 3.7 mmol), and tetrabutylammonium bromide (1.2 g, 3.72 mmol) were added, along with a mixed solvent of toluene (280 mL), ethanol (70 mL), and water (70 mL). The mixture was stirred and heated until it reached 75-80 °C. The mixture was then refluxed for 15 h. After the reaction was complete, the mixture was cooled to room temperature. The organic phase was separated by extraction with toluene and water, washed with water until neutral, dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a solid compound, namely intermediate N-4 (31.7 g, yield 61%).

[0212] By replacing naphthalene-2-boronic acid with [1,1'-biphenyl]-4-boronic acid, 3,5-diphenyl-phenylboronic acid, dibenzofuran-3-boronic acid, or 4-cyanobenzoboronic acid, the following intermediates N-5 to N-8 can be prepared using the same method.

[0213]

[0214] (3) Preparation of intermediate a-1

[0215]

[0216] 2-Bromo-1-nitronaphthalene (50 g, 198.36 mmol) was added to a flask, followed by tetrahydrofuran (500 mL). The temperature was lowered to -80°C to -90°C. A butyllithium THF solution (78.6 mL, 198.36 mmol) was added dropwise using a constant-pressure titration funnel. After the addition was complete, the temperature was maintained for 1 hour (-80°C to -90°C). Subsequently, trimethyl borate (22.67 g, 21 mL) was added dropwise using a constant-pressure titration funnel. Add 8.19 mmol), keep warm for 1 h (-80℃~-90℃) after the addition is complete, and let it rise naturally to room temperature to end the reaction; add the prepared 2 mol / L hydrochloric acid solution (99.18 mL) to the reaction solution, add water and dichloromethane to extract the organic phase, dry with anhydrous magnesium sulfate, remove the solvent under reduced pressure to obtain crude product; purify by recrystallization with dichloromethane / n-heptane to obtain white solid intermediate a-1 (25.82 g, yield 60%).

[0217] By replacing 2-bromo-1-nitronaphthalene with reactant A, intermediates a-2 to a-13 as shown in Table 1 were synthesized using a similar method as described above.

[0218] Table 1: Synthesis of intermediates a-1 to a-13

[0219]

[0220]

[0221] (4) Preparation of intermediate b-1

[0222]

[0223] Intermediate a-1 (25 g; 115.2 mmol), 2-bromocarbazole (27 g; 109.7 mmol), tetra(triphenylphosphine)palladium (1.27 g; 1.1 mmol), potassium carbonate (33.4 g; 241.4 mmol), and tetrabutylammonium bromide (7.07 g; 21.9 mmol) were added to a flask, along with a mixed solvent of toluene (200 mL), ethanol (40 mL), and water (40 mL). Under nitrogen protection, the mixture was heated to 80 °C and stirred for 8 hours. After cooling to room temperature, stirring was stopped, and the reaction mixture was washed with water to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure 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 light gray solid intermediate b-1 (27.8 g, yield 75%).

[0224] Using a method similar to that used for synthesizing intermediate b-1, intermediates b-2 to b-33 were synthesized by replacing intermediate a-1 with the compound shown in reactant B in Table 2 and replacing 2-bromocarbazole with the compound shown in reactant C.

[0225] Table 2: Synthesis of intermediates b-1 to b-33

[0226]

[0227]

[0228]

[0229]

[0230] (5) Preparation of intermediate c-1

[0231]

[0232] Intermediate b-1 (27 g, 79.8 mmol), 7-bromo-2-phenylbenzo[d]oxazole (24.1 g, 87.8 mmol), tris(dibenzylacetone)palladium (0.73 g, 0.80 mmol), tri-tert-butylphosphine (1.6 mL, 1 mol / L), sodium tert-butoxide (16.9 g, 175.5 mmol), and xylene (270 mL) were added to a flask, heated to 140 °C, and reacted for 4 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic phase was removed by anhydrous magnesium sulfate and concentrated to obtain a gray-black crude product. The crude product was purified by silica gel column chromatography using an ethyl acetate / n-heptane mixed solvent as the mobile phase to obtain solid intermediate c-1 (32.2 g; yield: 76%).

[0233] Using a method similar to that used for synthesizing intermediate c-1, intermediates c-2 to c-69 of Table 3 were synthesized by replacing intermediate b-1 with reactant D shown in Table 3 and intermediate E with 7-bromo-2-phenylbenzo[d]oxazole.

[0234] Table 3: Synthesis of intermediates c-1 to c-69

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] (6) Preparation of intermediate d-1

[0244]

[0245] Intermediate c-1 (32 g, 60.2 mmol), triphenylphosphine (39.4 g, 150.5 mmol), and o-dichlorobenzene (260 mL) were added to a flask, heated to 175 °C under nitrogen protection, and stirred for 18 hours. After cooling to room temperature, the reaction solution was washed with water, separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using an ethyl acetate / n-heptane system to obtain solid intermediate d-1 (16.5 g, yield 55%).

[0246] In the table below, reactant F replaces intermediate c-1, and intermediates d-2 to d-69 shown in the table below are synthesized using a similar method.

[0247] Table 4: Synthesis of intermediates d-2 to d-69

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] (7) Preparation of intermediate e-1

[0259]

[0260] 2,4-Dichloro-6-phenyl-1,3,5-triazine (20 g, 88.5 mmol), 4-fluorophenylboronic acid (8.3 g, 58.9 mmol), sodium carbonate (13.7 g, 129.7 mmol), tetrabutylammonium bromide (3.8 g, 11.8 mmol), toluene (160 mL), tetrahydrofuran (THF) (40 mL), and water (40 mL) were added to a flask. Under nitrogen protection, tetra(triphenylphosphine)palladium catalyst (0.68 g, 0.58 mmol) was added. The mixture was stirred thoroughly and slowly heated to 65 °C. The reaction was maintained at this temperature for 8 h. After the reaction was completed, the mixture was allowed to cool naturally to room temperature. The product was extracted with dichloromethane and water. The organic phase was concentrated until no water was observed, yielding a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain intermediate product e-1 (10.1 g, 60% yield).

[0261] Using a method similar to that used for synthesizing intermediate e-1, intermediates e-2 to e-16 listed in Table 5 were synthesized by replacing 2,4-dichloro-6-phenyl-1,3,5-triazine with reactant G as shown in Table 5 and replacing 4-fluorophenylboronic acid with reactant H.

[0262] Table 5: Synthesis of intermediates e-1 to e-16

[0263]

[0264]

[0265]

[0266] Preparation Example 1: Preparation of Compound A-1

[0267]

[0268] Intermediate d-1 (15.5 g, 31.1 mmol) and 2,4-diphenyl-6-chloro-1,3,5-triazine (10 g, 37.3 mmol) were added to a flask, cooled to 0°C to -10°C, and sodium hydride (0.97 g, 40.5 mmol) was added. The mixture was kept at this temperature for 2 h, allowed to rise naturally to room temperature, and extracted with dichloromethane and water. The organic phase was then concentrated until no water was observed, yielding a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane mixed solvent as the mobile phase to obtain the solid product compound A-1 (11.4 g, 50% yield).

[0269] Preparation Examples 2 to 69

[0270] Using a method similar to that used to synthesize compound A-1, reactant I as shown in Table 6 was used to replace intermediate d-1, and reactant J was used to replace 2,4-diphenyl-6-chloro-1,3,5-triazine, to synthesize preparation examples 2 to 69 of Table 6.

[0271] Table 6

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] Preparation Example 70: Preparation of Compound A-201

[0284]

[0285] Intermediate d-1 (15 g, 30.02 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.6 g, 30.2 mmol), tris(dibenzylacetone)dipalladium (0.27 g, 0.30 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (s-phos) (0.24 g, 0.60 mmol), sodium tert-butoxide (6.35 g, 66.0 mmol), and xylene (150 mL) were added to a flask. The mixture was heated to 140 °C and reacted for 4 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic phase was removed by anhydrous magnesium sulfate and concentrated to obtain a gray-black crude product. The crude product was purified by silica gel column chromatography using an ethyl acetate / n-heptane mixed solvent as the mobile phase to obtain the solid product compound A-201 (15.5 g, 60% yield).

[0286] Preparation Example 71

[0287] Using a method similar to that used to synthesize compound A-201, the compounds in Table 7 were synthesized by replacing intermediate d-1 with reactant K as shown in Table 7 and replacing 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine with reactant L.

[0288] Table 7

[0289]

[0290] The mass spectrometry results of the prepared compound are shown in Table 8 below:

[0291] Table 8: Mass Spectrometry Results of Compounds from the Preparation Examples

[0292]

[0293] NMR data for some compounds are shown in Table 9 below.

[0294] Table 9

[0295]

[0296] Fabrication and performance evaluation of organic electroluminescent devices

[0297] Example 1

[0298] Red organic electroluminescent device

[0299] Example 1

[0300] The anode is prepared by the following process: a glass substrate coated with a three-layer material of ITO / Ag / ITO (the thicknesses of the three layers are respectively...) is used. The substrate was cut into 40mm×40mm×0.7mm pieces and prepared into an experimental substrate with an anode and insulating layer pattern using photolithography. The surface was first cleaned with ultrapure water and isopropanol to remove surface contaminants. Then, the surface was treated with O2:N2 plasma gas to increase the work function of the anode.

[0301] F4-TCNQ was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and NPB is deposited on the hole injection layer to form a thickness of [thickness missing]. The first hole transport layer.

[0302] HT-04 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0303] On the second hole transport layer, compound A-99 (host material): Ir(piq)2(acac) were co-deposited in a ratio of 93%:7% to form a layer with a thickness of [missing information]. The red emissive layer (EML).

[0304] ET-01 and LiQ were mixed in a 1:1 weight ratio and then vapor-deposited to form... A thick electron transport layer (ETL) is formed by depositing ytterbium (Yb) onto the electron transport layer to create 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.

[0305] Furthermore, the thickness of the evaporation deposit on the aforementioned cathode is... The CP-1 is used to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.

[0306] Examples 2 to 17

[0307] Except that, when forming the light-emitting layer, the organic electroluminescent device was fabricated using the same method as in Example 1, except that the compound shown in Table 11 below was used instead of compound A-99.

[0308] Comparative Examples 1-4

[0309] Except that, when forming the light-emitting layer, compound A-1 was replaced with compounds a, b, c, and d respectively, the organic electroluminescent device was fabricated using the same method as in Example 1.

[0310] The main material structures used in the above embodiments and comparative examples are shown in Table 10 below:

[0311] Table 10

[0312]

[0313] For the organic electroluminescent device prepared as described above, at 20 mA / cm 2 The performance of the device was analyzed under the specified conditions, and the results are shown in Table 11 below:

[0314] Table 11

[0315]

[0316]

[0317] Referring to the table above, in Examples 1-17, the nitrogen-containing compound of this application was used as the main material of the red light-emitting layer. Compared with Comparative Examples 1-4, the device driving voltage was not much different, the luminous efficiency was increased by at least 13.9%, and the lifetime was increased by at least 20.4%.

[0318] Therefore, when the novel compound of this application is used as a host material for a single-component light-emitting layer to prepare a red organic electroluminescent device, it can effectively improve the efficiency and lifespan of the organic electroluminescent device.

[0319] Example 18: Red Organic Electroluminescent Device

[0320] The anode is prepared by the following process: a glass substrate coated with a three-layer material of ITO / Ag / ITO (the thicknesses of the three layers are respectively...) is used. The substrate was cut into 40mm×40mm×0.7mm pieces and prepared into an experimental substrate with cathode, anode and insulating layer patterns using photolithography. The surface was first cleaned with ultrapure water and isopropanol to remove surface contaminants. Then, the surface was treated with O2:N2 plasma gas to increase the work function of the anode.

[0321] F4-TCNQ was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and NPB is deposited on the hole injection layer to form a thickness of [thickness missing]. The first hole transport layer.

[0322] HT-05 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0323] On the second hole transport layer, the compound to be tested, A-1:RHp1:Ir(piq)2(acac), was co-deposited in a ratio of 50%:45%:5% to form a layer with a thickness of [missing information]. The red emissive layer (EML).

[0324] ET-03 and LiQ were mixed in a 2:1 weight ratio and then vapor-deposited to form... A thick electron transport layer (ETL) is formed by depositing ytterbium (Yb) onto the electron transport layer to create 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.

[0325] Furthermore, the thickness of the evaporation deposit on the aforementioned cathode is... The CP-1 is used to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.

[0326] Examples 19 to 71

[0327] The organic electroluminescent device was fabricated using the same method as in Example 18, except that the compounds shown in Table 13 were used to replace compound A-1 in Example 18 when forming the light-emitting layer.

[0328] Comparative Examples 5 to 8

[0329] Except that, when forming the light-emitting layer, compounds e, f, g, and h shown in Table 13 are used to replace compound A-1 in Example 18, the organic electroluminescent device is fabricated using the same method as in Example 18.

[0330] The main material structures used in the above embodiments and comparative examples are shown in Table 12 below:

[0331] Table 12

[0332]

[0333] For the organic electroluminescent device prepared as described above, at 20 mA / cm 2 The performance of the device was analyzed under the specified conditions, and the results are shown in Table 13 below:

[0334] Table 13

[0335]

[0336]

[0337]

[0338]

[0339] Referring to the table above, it can be seen that, compared with Comparative Examples 5-8, the devices prepared by using the compounds of the present invention as the hybrid host material of the red emitting layer in Examples 18-71 have a slightly lower driving voltage, and the luminous efficiency is increased by at least 17.3%, and the device lifetime is increased by at least 20%. Therefore, when the novel compounds of this application are used to prepare hybrid host type red organic electroluminescent devices, they can effectively improve the lifetime of organic electroluminescent devices and increase the luminous efficiency of the devices.

Claims

1. A nitrogen-containing compound, wherein, The nitrogen-containing compound has the structure shown in Formula 1: in, Indicates the connection site. Represents chemical bonds, Ring A and ring C are each independently selected from benzene rings or naphthalene rings; ring B is selected from benzene rings or naphthalene rings, and one of rings A, B and C must not be a benzene ring; Formula II The bonds shown are fused to any two adjacent carbon atoms of ring B in formula I; Either U1 or U2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted pyrene, and the other is selected from the structure shown in Formula III or IV. The substituents in U1 and U2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, cyclopentyl, cyclohexyl, adamantyl, trifluoromethyl, trideuterated methyl or trimethylsilyl; X is selected from S or O; X1, X2, and X3 are the same, and all are selected from N; Each of R1, R2, R3, R4 and R5 is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, pyridyl, trifluoromethyl, and biphenyl; n1 represents the number of substituents R1, and n1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. n2 represents the number of substituents R2, and n2 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n2 is greater than 1, any two R2s are the same or different. n3 represents the number of substituents R3, and n3 is selected from 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different. n4 represents the number of substituents R4, and n4 is selected from 1, 2 or 3. When n4 is greater than 1, any two R4s are the same or different. n5 represents the number of substituents R5, which can be selected from 1, 2, 3 or 4. When n5 is greater than 1, any two R5s can be the same or different. L, L1, L2, L3 and L4 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene. The substituents in L, L1, L2, L3 and L4 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or phenyl; Ar1 and Ar2 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoyl. The substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, trifluoromethyl, trideuterated methyl, or trimethylsilyl; optionally, any two adjacent substituents in Ar1 and Ar2 form a fluorene ring.

2. The nitrogen-containing compound according to claim 1, wherein, The nitrogen-containing compound is selected from the structure shown in the following structural formula: 。 3. The nitrogen-containing compound according to claim 1 or 2, wherein, L, L1, L2, L3, and L4 are each independently selected from single-bonded, substituted, or unsubstituted groups V; wherein the unsubstituted group V is selected from the group consisting of: ； in, It represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or phenyl; when the number of substituents on the substituted group V is greater than 1, the substituents may be the same or different.

4. The nitrogen-containing compound according to claim 1 or 2, wherein, Ar1 and Ar2 are each independently selected from substituted or unsubstituted groups W; wherein the unsubstituted group W is selected from the group consisting of: ； in, The substituted group W represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl, trifluoromethyl, trideuterated methyl, or trimethylsilyl; when the number of substituents on the substituted group W is greater than 1, the substituents may be the same or different.

5. The nitrogen-containing compound according to claim 1 or 2, wherein, The structure shown in Formula III is selected from the group consisting of the following groups: ； The structure shown in Formula IV is selected from the group consisting of the following groups: ； Each of R4 and R5 is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or trifluoromethyl.

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

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode and a cathode disposed opposite to each other, and at least one functional layer between the anode and the cathode, the functional layer comprising a nitrogen-containing compound as described in any one of claims 1-6.

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

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.

10. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 7 to 9.

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