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

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to a nitrogen-containing compound, an organic electroluminescent device and an electronic device. The nitrogen-containing compound has a structure as shown in formula 1. When the nitrogen-containing compound is used in an organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

Technical Field

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

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components for realizing electroluminescence is becoming increasingly wide. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light.

[0003] Existing technologies disclose host materials for fabricating organic light-emitting layers in organic electroluminescent devices. However, it remains necessary to continue developing novel materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] To address the aforementioned problems, this application aims to provide a nitrogen-containing compound and an organic electroluminescent device and electronic device comprising the nitrogen-containing compound. The nitrogen-containing compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving device efficiency and lifespan.

[0005] In a first aspect, this application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0006]

[0007] in,

[0008] Each R1, each R2, each R3, and each R4 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, and haloaryl with 6 to 12 carbon atoms;

[0009] n1 is the number of R1s, selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.

[0010] n2 is the number of R2, which can be selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different.

[0011] n3 is the number of R3s, which can be selected from 0, 1 or 2. When n3 is greater than 1, any two R3s are the same or different.

[0012] n4 is the number of R4s, selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different.

[0013] L1, L2, and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0014] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0015] The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, deuterated aryl groups with 6 to 12 carbon atoms, haloaryl groups with 6 to 12 carbon atoms, and trialkylsilyl groups with 3 to 12 carbon atoms.

[0016] 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.

[0017] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0018] The nitrogen-containing compound provided in this application has an indole-carbazole-indole core with a specific fusion mode. This specific fusion mode of indole-carbazole-indole gives the material suitable HOMO and T1 energy levels, thereby improving the hole injection and migration capabilities and energy transfer efficiency of the material. When this material is used as the host material of the organic light-emitting layer in organic electroluminescent devices (especially the hole-type host material of green light-emitting devices), it can significantly reduce the operating voltage of organic electroluminescent devices, improve current efficiency, and extend the lifespan.

[0019] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0020] 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.

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0022] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0023] Figure Labels

[0024] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0025] 320, Hole transport layer; 330, Hole adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0026] 360°, electron injection layer 400°, electronic device Detailed Implementation

[0027] 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 nitrogen-containing compound. The nitrogen-containing compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0028] A first aspect of this application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0029]

[0030] in,

[0031] Each R1, each R2, each R3, and each R4 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, and haloaryl with 6 to 12 carbon atoms;

[0032] n1 is the number of R1s, selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different.

[0033] n2 is the number of R2, which can be selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different.

[0034] n3 is the number of R3s, which can be selected from 0, 1 or 2. When n3 is greater than 1, any two R3s are the same or different.

[0035] n4 is the number of R4s, selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different.

[0036] L1, L2, and L3 may be the same or different, and are 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.

[0037] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0038] The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, deuterated aryl groups with 6 to 12 carbon atoms, haloaryl groups with 6 to 12 carbon atoms, and trialkylsilyl groups with 3 to 12 carbon atoms.

[0039] 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.

[0040] 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, cyano, halogen groups, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, deuterated aryl, haloaryl, trialkylsilyl, etc. The number of substituents can be one or more.

[0041] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0042] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0043] 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, benzofluoranthracene, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0044] In this application, terphenyl includes

[0045] 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.

[0046] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0047] In this application, aryl groups used as substituents for L1, L2, L3, Ar1, Ar2, and Ar3 include, but are not limited to, phenyl, naphthyl, etc.

[0048] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0049] 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, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 18 carbon atoms.

[0050] 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.

[0051] 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.

[0052] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

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

[0054] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0055] In this application, deuterated aryl refers to an aryl group containing at least one deuterated substituent. Specific embodiments of deuterated aryl include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0056] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0057] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0058]

[0059] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0060]

[0061] In some embodiments of this application, each R1, each R2, each R3 and each R4 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0062] In some embodiments of this application, n1, n2, n3 and n4 are all 0.

[0063] In some embodiments of this application, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0064] Optionally, the substituents in L1, L2 and L3 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.

[0065] In other embodiments of this application, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene.

[0066] Optionally, the substituents in L1, L2 and L3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0067] In some embodiments of this application, L1, L2, and L3 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0068]

[0069] In some specific embodiments of this application, L1, L2, and L3 may be the same or different, and are each independently selected from the group consisting of single bonds or the following groups:

[0070]

[0071] In some embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0072] Optionally, the substituents in Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

[0073] In other embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0074] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0075] In some embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are each independently selected from the group consisting of:

[0076]

[0077] In some specific embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are each independently selected from the group consisting of:

[0078]

[0079]

[0080] In some embodiments of this application, Whether identical or different, each is independently selected from the group consisting of the following groups:

[0081]

[0082] In some specific embodiments of this application, in formula 1, Whether identical or different, each is independently selected from the group consisting of the following groups:

[0083]

[0084]

[0085] In some embodiments of this application, the nitrogen-containing compound is selected from the group consisting of:

[0086]

[0087]

[0088]

[0089]

[0090] 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.

[0091] The nitrogen-containing compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0092] Optionally, the functional layer includes an organic light-emitting layer, which comprises 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.

[0093] Optionally, the functional layer further includes a hole transport layer located between the anode and the organic light-emitting layer.

[0094] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, a hole adjustment layer (also known as a hole auxiliary layer, a second hole transport layer, or a light-emitting auxiliary layer) 330, an organic light-emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially.

[0095] 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.

[0096] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0097]

[0098]

[0099] In one embodiment, the hole transport layer 320 may be composed of HT-27.

[0100] Optionally, the hole adjustment layer 330 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any specific limitations on these materials. For example, in some embodiments of this application, the hole adjustment layer 330 is composed of HT-28.

[0101] 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 321. 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. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;

[0102]

[0103]

[0104] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-27.

[0105] Optionally, the organic light-emitting layer 340 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 340 is composed of a host material and a guest material. Holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting 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.

[0106] The host material of the organic light-emitting layer 340 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises the nitrogen-containing compounds of this application.

[0107] The guest material of the organic light-emitting 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; 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,

[0108]

[0109] In some embodiments of this application, nitrogen-containing compounds are used as hole-type host materials for organic electroluminescent layers.

[0110] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 340 comprises the nitrogen-containing compound and GH-N of this application, and the guest material is GD-01.

[0111] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0112]

[0113]

[0114] In one embodiment of this application, the electron transport layer 350 may be composed of ET-1 and LiQ.

[0115] 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.

[0116] Optionally, an electron injection layer 350 may be disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).

[0117] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0118] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0119] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this disclosure is not limited thereto.

[0120] Synthesis Examples

[0121] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the nitrogen-containing compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. The compounds synthesized by methods not mentioned in this application are all commercially available starting materials.

[0122] Synthesis of intermediate a1:

[0123]

[0124] 2-Chlorocarbazole (23.5 g; 116.5 mmol), bromobenzene (22.0 g; 139.8 mmol), tris(dibenzylacetone)palladium (1.1 g; 1.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.1 g; 2.3 mmol), sodium tert-butoxide (16.8 g; 174.8 mmol), and xylene (200 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred at 135 °C–140 °C for 24 hours. The reaction mixture was cooled to room temperature, washed with water, and separated. 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 dichloromethane / n-heptane as eluent to give a pale yellow solid intermediate a1 (25.9 g; yield: 80%).

[0125] Following the synthetic method for intermediate a1, reactant A in Table 1 was substituted for bromobenzene to synthesize the intermediates shown in Table 1 below:

[0126] Table 1

[0127]

[0128] Synthesis of intermediate b1:

[0129]

[0130] Under nitrogen protection, intermediate a1 (25.5 g; 91.8 mmol), pinacol diboronate (35.0 g; 137.7 mmol), tris(dibenzylacetone)dipalladium (0.8 g; 0.9 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.9 g; 1.8 mmol), potassium acetate (18.0 g; 183.6 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 100 °C–105 °C for 12 hours. The reaction mixture was cooled to room temperature, and dichloromethane and deionized water were added. The mixture was separated, and the organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to give a white solid intermediate b1 (25.6 g; yield: 76%).

[0131] Referring to the synthesis method of intermediate b1, reactant B in Table 2 was used to replace intermediate a1 to synthesize the intermediates shown in Table 2 below:

[0132] Table 2

[0133]

[0134]

[0135] Synthesis of intermediate c1:

[0136]

[0137] Under nitrogen protection, 2,3-dichloronitrobenzene (13.3 g; 69.3 mmol), intermediate b1 (25.6 g; 69.3 mmol), tetratetraphenylphosphine palladium (1.6 g; 1.4 mmol), potassium carbonate (19.1 g; 138.5 mmol), tetrabutylammonium bromide (4.5 g; 13.9 mmol), toluene (200 mL), ethanol (50 mL), and deionized water (50 mL) were added to a round-bottom flask. The mixture was heated to 75 °C–80 °C and stirred for 72 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate c1 (19.9 g; yield: 72%).

[0138] Following the synthetic method of intermediate c1, reactant C in Table 3 was used to replace intermediate b1 to synthesize the intermediates shown in Table 3 below:

[0139] Table 3

[0140]

[0141]

[0142] Synthesis of intermediate d1:

[0143]

[0144] Under nitrogen protection, intermediate C1 (19.8 g; 49.6 mmol), triphenylphosphine (32.6 g; 124.1 mmol), and o-dichlorobenzene (200 mL) were added to a round-bottom flask. The mixture was stirred and heated to 175 °C–180 °C for 24 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system, and then purified by recrystallization using the same system to give a white solid intermediate D1 (10.3 g; yield: 57%).

[0145] Referring to the synthesis method of intermediate d1, reactant D in Table 4 was used to replace intermediate c1 to synthesize the intermediates shown in Table 4 below:

[0146] Table 4

[0147]

[0148]

[0149] Synthesis of intermediate e1:

[0150]

[0151] Intermediate d1 (10.2 g; 27.8 mmol), bromobenzene (4.8 g; 30.6 mmol), tris(dibenzylacetone)dipalladium (0.3 g; 0.3 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.3 g; 0.6 mmol), sodium tert-butoxide (4.0 g; 41.7 mmol), and xylene (100 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred at 135 °C–140 °C for 16 hours. The reaction mixture was cooled to room temperature, washed with water, and separated. 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 dichloromethane / n-heptane as eluent to obtain a white solid intermediate e1 (9.5 g; 77%).

[0152] Following the synthetic method for intermediate e1, reactant E was used to replace intermediate d1, and reactant F was used to replace bromobenzene, as shown in Table 5, to synthesize the intermediates shown in Table 5 below:

[0153] Table 5

[0154]

[0155]

[0156] Synthesis of intermediate f1:

[0157]

[0158] Under nitrogen protection, intermediate e1 (9.5 g; 21.4 mmol), pinacol diboronate (8.2 g; 32.2 mmol), tris(dibenzylacetone)dipalladium (0.2 g; 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g; 0.4 mmol), potassium acetate (3.2 g; 32.2 mmol), and 1,4-dioxane (100 mL) were added to a round-bottom flask. The mixture was stirred at 100 °C–105 °C for 24 hours. The reaction mixture was cooled to room temperature, and dichloromethane and deionized water were added. The mixture was separated, the organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to give a white solid intermediate f1 (8.6 g; yield: 75%).

[0159] Following the synthetic method of intermediate f1, reactant G from Table 6 was used to replace intermediate e1 to synthesize the intermediates shown in Table 6 below:

[0160] Table 6

[0161]

[0162]

[0163] Synthesis of intermediate g1:

[0164]

[0165] Under nitrogen protection, intermediate f1 (8.5 g; 15.9 mmol), 2-bromonitrobenzene (3.4 g; 16.7 mmol), tetratetraphenylphosphine palladium (0.4 g; 0.3 mmol), potassium carbonate (4.4 g; 31.8 mmol), tetrabutylammonium bromide (1.0 g; 3.2 mmol), toluene (70 mL), ethanol (20 mL), and deionized water (20 mL) were added to a round-bottom flask. The mixture was heated to 75 °C–80 °C and stirred for 16 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate g1 (6.6 g; yield: 78%).

[0166] Following the synthetic method of intermediate g1, reactant H in Table 7 was used to replace intermediate f1 to synthesize the intermediates shown in Table 7 below:

[0167] Table 7

[0168]

[0169]

[0170] Synthesis of intermediate h1:

[0171]

[0172] Under nitrogen protection, intermediate g1 (6.4 g; 12.1 mmol), triphenylphosphine (7.9 g; 30.2 mmol), and o-dichlorobenzene (60 mL) were added to a round-bottom flask. The mixture was stirred and heated to 175 °C–180 °C for 24 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure. The crude product was purified by recrystallization using a toluene / n-heptane solvent system to obtain a white solid intermediate h1 (4.5 g; 75%).

[0173] Following the synthetic method of intermediate h1, reactant J in Table 8 was used to replace intermediate g1 to synthesize the intermediates shown in Table 8 below:

[0174] Table 8

[0175]

[0176]

[0177]

[0178] Synthesis of Compound 1:

[0179]

[0180] Intermediate h1 (4.2 g; 8.4 mmol), bromobenzene (1.5 g; 9.3 mmol), tris(dibenzylacetone)dipalladium (0.1 g; 0.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.1 g; 0.2 mmol), sodium tert-butoxide (1.2 g; 12.7 mmol), and xylene (40 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred at 135–140 °C for 16 hours. The reaction mixture was cooled to room temperature, washed with water, and separated. 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 toluene / n-heptane as the eluent. The obtained sample was then purified by recrystallization using a toluene / n-heptane solvent system to obtain white crystalline compound 1 (3.5 g; yield: 72%).

[0181] Following the synthetic method of compound 1, reactant M in Table 9 was substituted for intermediate h1, and reactant N was substituted for bromobenzene to synthesize the compounds shown in Table 9 below:

[0182] Table 9

[0183]

[0184]

[0185]

[0186] Mass spectrometry data for some compounds are shown in Table 10 below.

[0187] Table 10

[0188]

[0189]

[0190] The NMR data of some compounds are shown in Table 11 below.

[0191] Table 11

[0192]

[0193] Fabrication of organic electroluminescent devices

[0194] This application also provides an organic electroluminescent device, including an anode, a cathode, and a functional layer between the anode and the cathode, wherein the functional layer includes the nitrogen-containing compound described above. The organic electroluminescent device of this application will now be described in detail through embodiments. However, the following embodiments are merely examples of this application and are not intended to limit the scope of this application.

[0195] Example 1: Green Organic Electroluminescent Device

[0196] Devices are fabricated using the following process.

[0197] At ITO / Ag / ITO thickness On the experimental substrate, surface treatment is performed using ultraviolet light, ozone, and O2:N2 ions to increase the work function of the anode. Organic solvents can be used to clean the surface of the experimental substrate to remove impurities and oil stains.

[0198] Compound HT-27 and PD were co-deposited on the experimental substrate at a deposition rate of 98%:2%, forming a layer with a thickness of [missing information]. A hole injection layer is formed, and then compound HT-27 is deposited on the hole injection layer to form a thickness of [missing information]. The hole transport layer.

[0199] Compound HT-28 was deposited on the hole transport layer to form a thickness of [missing information]. Hole adjustment layer.

[0200] On the hole adjustment layer, compound 1 (P-type dopant), compound N (N-type dopant), and GD-01 (doped guest) were co-deposited at a deposition rate of 55%:45%:12% to form a layer with a thickness of [missing information]. The organic light-emitting layer (green light-emitting layer).

[0201] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate to form a layer with a thickness of [missing information]. The electron transport layer;

[0202] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed; then, magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate of 10%:90%, forming a layer with a thickness of [missing information]. The cathode.

[0203] Finally, compound CP-1 was deposited on the cathode to form a layer with a thickness of [missing information]. The organic capping layer (CPL) is used to complete the fabrication of green organic electroluminescent devices.

[0204] Examples 2 to 25:

[0205] Except that, when preparing the green light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 13 was used instead of compound 1 in Example 1.

[0206] Comparative Examples 1 to 5:

[0207] Except that when preparing the green light-emitting layer, compound A, compound B, compound C, compound D or compound E from Table 13 were used to replace compound 1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0208] The structures of the compounds used in preparing the devices of the above embodiments and comparative examples are listed in Table 12 below.

[0209] Table 12

[0210]

[0211] The performance of the green organic electroluminescent devices prepared in Examples 1-25 and Comparative Examples 1-5 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 13 below.

[0212] Table 13

[0213]

[0214]

[0215] Referring to Table 13 above, it can be seen that when the compounds of this application are used in the organic light-emitting layer of green organic electroluminescent devices, the device performance is significantly improved. Specifically, compared with the organic electroluminescent devices of Comparative Examples 1 to 5, the organic electroluminescent devices of Examples 1 to 25 have an efficiency improvement of at least 13.4% and a lifetime improvement of at least 15.0%.

[0216] When the compounds of this application are used in the organic light-emitting layer of green organic light-emitting devices, the device performance is significantly improved compared to Comparative Examples 1-5. This improvement is likely due to the fact that, compared to Comparative Examples 1-5, the core of the compounds in this application has an indole-carbazole-indole with a specific fusion mode. This specific fusion mode of indole-carbazole-indole gives the material suitable HOMO and T1 energy levels, thereby improving the hole injection and migration capabilities and energy transfer efficiency. When this material is used as the host material of the organic light-emitting layer in organic light-emitting devices (especially the hole-type host material for green light-emitting devices), it can reduce the operating voltage of the organic light-emitting device, improve current efficiency, and extend its lifespan.

[0217] The 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.

Claims

1. A nitrogen-containing compound, characterized in that, The nitrogen-containing compound has the structure shown in Formula 1: in, Each R1, each R2, each R3, and each R4 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, and haloaryl with 6 to 12 carbon atoms; n1 is the number of R1s, selected from 0, 1, 2, 3 or 4. When n1 is greater than 1, any two R1s are the same or different. n2 is the number of R2, which can be selected from 0, 1 or 2. When n2 is greater than 1, any two R2 are the same or different. n3 is the number of R3s, which can be selected from 0, 1 or 2. When n3 is greater than 1, any two R3s are the same or different. n4 is the number of R4s, selected from 0, 1, 2, 3 or 4. When n4 is greater than 1, any two R4s are the same or different. L1, L2, and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, and substituted or unsubstituted carbazolylene. The substituents in L1, L2, and L3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterated phenyl; Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene. The substituents in Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterated phenyl.

2. The nitrogen-containing compound according to claim 1, characterized in that, Each of R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

3. The nitrogen-containing compound according to claim 1, characterized in that, In Equation 1, Whether identical or different, each is independently selected from the group consisting of the following groups:

4. The nitrogen-containing compound according to claim 3, characterized in that, Whether identical or different, each is independently selected from the group consisting of the following groups:

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

6. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises a nitrogen-containing compound as described in any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The functional layer includes an organic light-emitting layer, which contains a nitrogen-containing compound as described in any one of claims 1 to 5.

8. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 6 or 7.

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