Nitrogen-containing compound, organic electroluminescent device, and electronic apparatus

Abstract

The present application relates to a nitrogen-containing compound, an organic electroluminescent device, and an electronic apparatus. The nitrogen-containing compound in the present application has a structure as represented by formula 1. The nitrogen-containing compound is applied to the organic electroluminescent device, thereby significantly improving the performance of the device.

Description

Nitrogen compounds, organic electroluminescent devices and electronic devices

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese patent application No. CN202510279700.7, filed on March 10, 2025, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application belongs to the field of organic materials technology, and in particular relates to a nitrogen-containing compound, an organic electroluminescent device, and an electronic device. Background Technology

[0004] Organic electroluminescent devices (OLEDs) are used to manufacture novel display products and lighting products, and are gradually replacing traditional liquid crystal displays and fluorescent lighting, with a very wide range of applications. The functional layers constituting an OLED device generally include a hole injection layer, a hole transport layer, a hole auxiliary layer, an organic light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the anode and cathode, an electric field is generated between the electrodes. Under the influence of this 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. These excitons are in an excited state and release energy outward, thus causing the organic light-emitting layer to emit light.

[0005] With display technology already applied in smartphones, tablets, and other fields, people have increasingly higher demands for the performance of these products. Current OLED materials and device structures still cannot completely solve the problems related to efficiency, lifespan, and cost of OLED products. Therefore, it remains necessary to continue developing new materials to further improve the performance of electronic components. Summary of the Invention

[0006] To address the aforementioned problems, this application aims to provide a nitrogen-containing compound, an organic electroluminescent device, and an electronic device. Using the nitrogen-containing compound in an organic electroluminescent device can improve the device's performance, such as reducing the device's driving voltage and increasing its efficiency and lifespan.

[0007] A first aspect of this application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0008] Where D represents deuterium;

[0009] n represents the number of D, which can be selected from 0, 1, 2, 3 or 4;

[0010] Ring A is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups;

[0011] The substituent in ring A is deuterium;

[0012] X is selected from C(R1R2), O, or S;

[0013] R1 and R2 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0014] L1 is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 20 carbon atoms;

[0015] The substituents in R1, R2 and L1 may be the same or different, and are independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or deuterated aryl with 6 to 12 carbon atoms.

[0016] Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 20 carbon atoms;

[0017] The substituents in Ar1 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or deuterated aryl with 6 to 10 carbon atoms.

[0018] A second aspect of this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the nitrogen-containing compound described in the first aspect of this application.

[0019] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0020] This application provides a nitrogen-containing compound composed of a specifically deuterated terphenyl group, a small-molecule aromatic ring fused benzofuran / benzothiophene / indene, and an aromatic amine containing a small aryl group. The compound's glass transition temperature (Tg) is increased by introducing a higher bond energy CD bond into its molecular structure. Furthermore, the use of a specifically deuterated terphenyl group linked to the aromatic amine enhances the twist of the molecule, thereby improving its film-forming properties and thermal stability. Further, the compound must contain at least one small-molecule aromatic ring fused benzofuran / benzothiophene / indene structure to improve hole mobility. The nitrogen-containing compound provided in this application, containing a multi-substituted twisted structure (specifically deuterated terphenyl group), can give the material higher lateral resistance, thus solving the lateral crosstalk problem in devices. When used as a hole auxiliary layer material in organic electroluminescent devices, this compound can significantly improve device performance.

[0021] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0022] 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.

[0023] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0024] Figure 2 is a schematic diagram of the structure of an electronic device according to this application.

[0025] Reference numerals 100, 200, 300, 310, 320, 330, 340, 350, 360, 400, and 350, respectively, represent the following: Organic light-emitting layer; Electron transport layer; Electron injection layer; and Electronic device. Detailed Implementation

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0027] In a first aspect, this application provides a nitrogen-containing compound having the structure shown in Formula 1:

[0028] Where D represents deuterium;

[0029] n represents the number of D, which can be selected from 0, 1, 2, 3 or 4;

[0030] Ring A is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups;

[0031] The substituent in ring A is deuterium;

[0032] X is selected from C(R1R2), O, or S;

[0033] R1 and R2 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0034] L1 is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 20 carbon atoms;

[0035] The substituents in R1, R2 and L1 may be the same or different, and are independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or deuterated aryl with 6 to 12 carbon atoms.

[0036] Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 20 carbon atoms;

[0037] The substituents in Ar1 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or deuterated aryl with 6 to 10 carbon atoms.

[0038] In this application, D represents deuterium.

[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 context, each q is independently 0, 1, 2, or 3, and each R” is independently selected from hydrogen, deuterium, fluorine, and 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, and 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, alkyl, aryl, heteroaryl, deuterated aryl, haloaryl, cycloalkyl, alkoxy, alkylthio, 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. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group 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 and Ar1 include, but are not limited to, phenyl groups.

[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 linked by carbon-carbon bonds, 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 can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, alkyl groups, cycloalkyl groups, deuterated aryl groups, and haloaryl groups. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in 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, 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, pentadeuterated biphenyl, and nonadeuterated biphenyl.

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

[0055] In this application, the 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.

[0056] For another example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule by 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.

[0057] In some embodiments of this application, the nitrogen-containing compound is selected from compounds shown in Formula 1-1 or Formula 1-2:

[0058] In Equations 1-1 and 1-2, D, ring A, X, n, L1, and Ar1 are defined as in Equation 1.

[0059] In some embodiments of this application, the nitrogen-containing compound is selected from the structures shown in Formulas 1-1-1 to 1-2-8:

[0060] In Equations 1-1-1 to 1-2-8, D, X, n, L1 and Ar1 are as defined in Equation 1.

[0061] In some embodiments of this application, R1 and R2 may be the same or different, and are each independently selected from methyl, ethyl, trideuterated methyl or phenyl.

[0062] In some embodiments of this application, L1 is selected from arylene groups having a single bond, substituted or unsubstituted carbon atoms, and having 6 to 12 carbon atoms. For example, L1 is selected from substituted or unsubstituted arylene groups having a single bond, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.

[0063] Optionally, the substituents in L1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl, phenyl or pentadeuterated phenyl with 1 to 5 carbon atoms.

[0064] In some embodiments of this application, L1 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0065] Optionally, the substituents in L1 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.

[0066] In some embodiments of this application, L1 is selected from the group consisting of single bonds or groups consisting of:

[0067] Specifically, L1 is selected from the group consisting of single bonds or groups consisting of the following:

[0068] In some embodiments of this application, Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 18 carbon atoms. For example, Ar1 is selected from substituted or unsubstituted aryl groups having 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0069] Optionally, the substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl, phenyl, naphthyl or pentadeuterated phenyl with 1 to 5 carbon atoms.

[0070] Further optionally, Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 15 carbon atoms.

[0071] Further optionally, Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 12 carbon atoms.

[0072] In some embodiments of this application, Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted terphenyl.

[0073] Optionally, the substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

[0074] In some embodiments of this application, Ar1 is selected from the group consisting of:

[0075] Specifically, Ar1 is selected from the group consisting of the following groups:

[0076] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0077] Optionally, in Equation 1 Selected from the group consisting of the following groups:

[0078] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0079] Optionally, in Equation 1 Selected from the group consisting of the following groups:

[0080] In some preferred embodiments of this application, the nitrogen-containing compound is selected from compounds represented by Formula 1-1;

[0081] X is selected from C(R1R2), O, or S;

[0082] Ring A is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups;

[0083] The substituent in ring A is deuterium;

[0084] R1 and R2 may be the same or different, and are independently selected from methyl, ethyl, trideuterated methyl or phenyl;

[0085] L1 is a single bond;

[0086] Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, and substituted or unsubstituted triphenyl.

[0087] The substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

[0088] In some embodiments of this application, the nitrogen-containing compound is selected from the group consisting of:

[0089] In a second aspect, this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the nitrogen-containing compound described in the first aspect of this application.

[0090] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0091] In some embodiments of this application, as shown in FIG1, an organic electroluminescent device may include an anode 100, a hole transport layer 320, a hole auxiliary layer 330, an organic light-emitting layer 340, an electron transport layer 350, and a cathode 200 stacked sequentially.

[0092] Optionally, the anode 100 comprises an anode material, preferably one with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. A transparent electrode comprising indium tin oxide (ITO) is preferably used as the anode.

[0093] Optionally, the hole transport layer 320 includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can refer to existing technologies for selection, and this application does not impose any special limitations in this regard. In some embodiments of this application, the hole transport layer 320 is HT-1.

[0094] Optionally, the hole assist layer 330 (also known as a hole adjustment layer, electron blocking layer, luminescence adjustment layer, hole buffer layer, luminescence assist layer, or second hole transport layer) 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. For example, in one embodiment of this application, the hole assist layer 330 is a nitrogen-containing compound.

[0095] 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, and this application does not impose any special limitations on this. In some embodiments of this application, the hole injection layer 310 may be composed of PD-1 and HT-1.

[0096] 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 and electrons injected into the organic light-emitting layer 330 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.

[0097] 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, and this application does not impose any special restrictions on this.

[0098] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device, the organic electroluminescent device includes an organic light-emitting layer, the organic light-emitting layer includes host materials RPH-1 and RNH-1, and guest material RD-1.

[0099] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can 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 special limitations on this comparison.

[0100] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-1 and LiQ.

[0101] 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 containing magnesium and silver may be used as the cathode.

[0102] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0103] Thirdly, this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0104] According to one embodiment, as shown in FIG2, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0105] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this application is not limited thereto.

[0106] Synthesis Examples

[0107] Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the organic materials 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. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0108] The compounds of this application can be prepared by a two-step Buchwald-Hartwig reaction using the synthetic method shown in the following general formula.

[0109] The synthesis method of the intermediate IN-TPA-A is as follows:

[0110] Under nitrogen protection, deuterated phenylboronic acid (101.2 g, 797.15 mmol), 2,3-dibromoaniline (100.0 g, 398.53 mmol), tetra(triphenylphosphine)palladium (23.03 g, 19.93 mmol), tetrabutylammonium bromide (51.39 g, 159.41 mmol), potassium carbonate (220.3 g, 1.594 mol), toluene (1000 mL), ethanol (500 mL), and water (200 mL) were added to a 2 L reaction flask. After the addition was complete, stirring was started, and the mixture was heated to 70-75 °C and refluxed for 12 hours. The reaction was then stopped, cooled to room temperature, extracted with dichloromethane, and the organic phase was washed with water until neutral. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by recrystallization with a toluene / petroleum ether mixed solvent and dried to obtain intermediate IN-TPA-A (82.54 g, yield: 81.1%).

[0111] Following the synthesis method of intermediate IN-TPA-A, using raw material 1 in Table 1 instead of 2,3-dibromoaniline, intermediate IN-TPA-B as shown in Table 1 was synthesized.

[0112] Table 1

[0113] Synthesis of intermediate IN-NH-A1

[0114] Under nitrogen protection, intermediate IN-TPA-A (25.3 g, 99.09 mmol), 4-bromobiphenyl (22.0 g, 94.38 mmol), tris(dibenzylacetone)dipalladium (0.86 g, 0.94 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.9 g, 1.89 mmol), sodium tert-butoxide (13.6 g, 141.56 mmol), and toluene (200 mL) were added to a reaction flask. Stirring was started, and the mixture was heated to 108 °C for 3 hours. After cooling to room temperature, the reaction solution was washed with water and dried over anhydrous magnesium sulfate. The solution was filtered, and the solvent was removed under reduced pressure to obtain a yellow crude solid. The crude product was purified by recrystallization using a toluene / petroleum ether mixture to give intermediate IN-NH-A1 (30.04 g, yield: 78.1%).

[0115] Referring to the synthesis method of intermediate IN-NH-A1, using raw material 2 in Table 2 instead of IN-TPA-A and raw material 3 instead of 4-bromobiphenyl, the reaction yields the corresponding intermediates IN-NH-Ax (x is an integer from 2 to 11) and IN-NH-Bx (y is an integer from 1 to 10);

[0116] Table 2

[0117] Synthesis of compound A1

[0118] Under nitrogen protection, intermediate IN-NH-A1 (7.0 g, 17.17 mmol), 2-bromo-9,9-dimethylfluorene (4.69 g, 17.17 mmol), tris(dibenzylacetone)dipalladium (0.16 g, 0.17 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.14 g, 0.34 mmol), sodium tert-butoxide (2.47 g, 25.76 mmol), and toluene (70 mL) were added to a reaction flask. Stirring was started, and the mixture was heated to 108 °C for 5 hours. After cooling to room temperature, the reaction solution was washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain a yellow crude solid. The crude product was purified by recrystallization using a toluene / petroleum ether mixed solvent to obtain a white solid compound A1 (5.1 g, yield: 49.6%), mass spectrometry: m / z = 600.3 [M+H]+.

[0119] Following the synthetic method of compound A1, intermediate IN-NH-A1 was replaced by reactant 4 from Table 3, and 2-bromo-9,9-dimethylfluorene was replaced by reactant 5, to synthesize the compounds shown in Table 3.

[0120] Table 3

[0121] NMR data for some compounds are shown in Table 4 below.

[0122] Table 4

[0123] Fabrication of organic electroluminescent devices

[0124] Example 1: Fabrication of a red organic electroluminescent device

[0125] Devices are fabricated using the following process.

[0126] At ITO / Ag / ITO thickness On the experimental substrate, the surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0127] Compounds HT-1 and PD-1 were co-deposited on an experimental substrate at a deposition rate ratio of 97%:3%, forming a layer with a thickness of [missing information]. Hole injection layer.

[0128] Compound HT-1 was deposited onto the hole injection layer to form a thickness of [missing information]. The hole transport layer.

[0129] Compound A1 of this application is deposited on the hole transport layer to form a thickness of [missing information]. Hole auxiliary layer.

[0130] On the hole-assisted layer, compounds RPH-1 (P-type dopant), RNH-1 (N-type dopant), and RD-1 (doped guest) were co-deposited at a deposition rate ratio of 60%:40%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0131] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer.

[0132] Yb is deposited on the electron transport layer to form a thickness of The electron injection layer.

[0133] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a deposition rate ratio of 10%:90%, forming a layer with a thickness of [missing information]. The cathode.

[0134] Compound CP-1 was deposited on the cathode to form a thickness of [missing information]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0135] Examples 2 to 29:

[0136] Except that, when preparing the hole auxiliary layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 5 was used instead of compound A1 in Example 1.

[0137] Comparative Examples 1 to 4:

[0138] Except that when preparing the hole auxiliary layer, compounds A to D from Table 5 were used to replace compound A1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0139] The compounds used in preparing the devices of the above embodiments and comparative examples have the following structures:

[0140] The performance of the red organic electroluminescent devices prepared in Examples 1 to 29 and Comparative Examples 1 to 4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 30 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 5 below.

[0141] Table 5

[0142] As shown in Table 5 above, when the nitrogen-containing compound of this application is used in the hole-assisted layer of the red organic electroluminescent device, the device performance can be significantly improved. Specifically, compared with Comparative Examples 1 to 4, the current efficiency of the organic electroluminescent devices of Examples 1 to 29 is improved by at least 15.3%, and the lifetime is improved by at least 16.8%.

[0143] Compared to Comparative Examples 1 to 4, the compounds of this application, when used as hole auxiliary layers in organic electroluminescent devices, significantly improve the current efficiency and lifespan of the devices. Compared to Compound B, the specific deuterated terphenyl and aromatic amine single-bond connections in the compounds of this application further enhance the hole transport rate, thereby significantly improving device efficiency.

[0144] Compared to compound C, the compound in this application uses a small-molecule aromatic ring fused benzofuran / benzothiophene / indene with high mobility, which is then connected to a benzene ring containing two ortho-linked deuterated phenyl groups via N atoms to form a twisted molecule with high mobility. Furthermore, since the selected fused ring containing ring A does not contain non-hydrogen substituents, it does not increase the molecular weight of the compound. Therefore, applying compounds with this type of structure to devices can better regulate the balance of hole transport and injection, thereby improving the efficiency and lifetime of the devices.

[0145] Compared with compound D, the aromatic amine group in the compound of this application is selected as an aryl group with 10 to 18 carbon atoms. On the one hand, this is to ensure that the conjugated region of the molecule is more concentrated so that its mobility decreases and affects the voltage and efficiency of the device. On the other hand, it is also to prevent the overall molecular weight of the compound from being too large, which would cause problems such as increased evaporation temperature and poor thermal stability, thus extending the lifespan of the device.

[0146] The above description, in conjunction with the accompanying drawings, details some embodiments of this application. However, this application is not limited to the specific details described above. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and all such simple modifications fall within the protection scope of this application.

Claims

1. A nitrogen-containing compound characterized in that, The nitrogen-containing compound has a structure shown in Formula 1: Where D represents deuterium; n represents the number of D, which can be selected from 0, 1, 2, 3 or 4; Ring A is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups; The substituent in ring A is deuterium; X is selected from C(R1R2), O, or S; R1 and R2 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms. L1 is selected from single bonds and substituted or unsubstituted aryl groups with 6 to 20 carbon atoms; The substituents in R1, R2 and L1 may be the same or different, and are independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or deuterated aryl with 6 to 12 carbon atoms. Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 20 carbon atoms; The substituents in Ar1 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or deuterated aryl with 6 to 10 carbon atoms.

2. The nitrogen-containing compound according to claim 1, characterized by The nitrogen-containing compound is selected from the group consisting of compounds represented by Formula 1-1 or Formula 1-2: In Equations 1-1 and 1-2, D, ring A, X, n, L1, and Ar1 are as defined in claim 1.

3. The nitrogen-containing compound according to claim 1 or 2, characterized by R1 and R2 may be the same or different, and are independently selected from methyl, ethyl, trideuterated methyl or phenyl.

4. The nitrogen-containing compound according to any one of claims 1 to 3, characterized by L1 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L1 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.

5. The nitrogen-containing compound according to any one of claims 1 to 4, characterized by Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 18 carbon atoms; Optionally, the substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl, phenyl, naphthyl or pentadeuterated phenyl with 1 to 5 carbon atoms.

6. The nitrogen-containing compound according to any one of claims 1 to 5, characterized by Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, and substituted or unsubstituted terphenyl. Optionally, the substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

7. The nitrogen-containing compound according to any one of claims 1 to 6, characterized by X is selected from C(R1R2), O, or S; Ring A is selected from substituted or unsubstituted phenyl groups and substituted or unsubstituted naphthyl groups; The substituent in ring A is deuterium; R1 and R2 may be the same or different, and are independently selected from methyl, ethyl, trideuterated methyl or phenyl; L1 is a single bond; Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, and substituted or unsubstituted triphenyl. The substituents in Ar1 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

8. The nitrogenous compound according to any one of claims 1 to 7, wherein Ar1is selected from the group consisting of: Optionally, Ar1is selected from the group consisting of:

9. The nitrogenous compound according to any one of claims 1 to 8, wherein in formula 1 is selected from the group consisting of Optionally, in formula 1 selected from the group consisting of:

10. The nitrogenous compound according to any one of claims 1 to 9, wherein in formula 1 is selected from the group consisting of Optionally, in formula 1 selected from the group consisting of:

11. The nitrogenous compound according to any one of claims 1 to 10, wherein The nitrogen-containing compound is selected from the group consisting of:

12. An organic electroluminescent device, characterized by 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 11; Optionally, the functional layer includes a hole-assist layer; the hole-assist layer includes the nitrogen-containing compound; Optionally, the functional layer further includes a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, and an electron injection layer; Optionally, the organic electroluminescent device is a red organic electroluminescent device.

13. An electronic device, characterized by Including the organic electroluminescent device as described in claim 12.

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