Nitrogen-containing heterocyclic compound, organic electroluminescent device and electronic equipment

Abstract

The invention provides a nitrogen-containing heterocyclic compound, an organic electroluminescent device and electronic equipment, and the nitrogen-containing heterocyclic compound, the organic electroluminescent device and the electronic equipment show excellent performance when being used as an organic electroluminescent material, especially as an N-type charge generation layer material. The compound has a structure as shown in a formula (1) or (2), in the formula (1) and the formula (2), Ar1, Ar2 and Ar3 are independently selected from C6-C30 heteroaryl containing at least two nitrogen atoms, at least one of Ar1-Ar3 is selected from substituted or unsubstituted phenanthroline groups, and at least one of Ar1-Ar3 is not substituted or unsubstituted phenanthroline groups; ar4 and Ar6 are respectively and independently selected from substituted or unsubstituted C6-C30 heteroaryl containing at least two nitrogen atoms, and Ar5 is selected from C6-C30 heteroaryl containing at least two nitrogen atoms; if Ar5 is selected from phenanthrolinyl, at least one of Ar4 and Ar6 is not phenanthrolinyl; and if Ar5 is not a phenanthrolinyl group, at least one of Ar4 and Ar6 is selected from a phenanthrolinyl group.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and more specifically, to a nitrogen-containing heterocyclic compound, an organic electroluminescent device and an electronic device. Background Art

[0002] An organic light emitting diode (OLED) is a self-luminous display device based on organic electroluminescent materials. It has the characteristics of not requiring a backlight source and being thin. It is a technology suitable for flexible light-emitting display devices.

[0003] Organic electroluminescent materials are polymers or small molecules that emit light under the influence of an electric field. To improve the stability and efficiency of organic electroluminescent materials in organic electroluminescent devices, a multilayer organic thin film is prepared between the anode and cathode. These organic thin film layers can be divided into a hole injection layer, a hole transport layer, a main luminescent layer, a luminescent layer dopant, an electron transport layer, and an electron injection layer.

[0004] When an electric field is applied between the anode and cathode of an organic electroluminescent device, holes are injected from the anode and move through the hole transport layer to the light-emitting layer. Simultaneously, electrons are injected from the cathode and move through the electron transport layer to the light-emitting layer. The holes and electrons that move to the light-emitting layer combine to form excitons. When the excitons transition from an excited state to a ground state, energy is released as light, causing the device to emit light.

[0005] OLED devices are classified into various structures based on the structure of the light-emitting layer, including single-layer, multi-doped, multi-layer, and stacked structures. In stacked devices, the addition of a charge generation layer within the light-emitting unit improves device performance. However, there is currently a lack of high-performance materials suitable for the charge generation layer in stacked devices, limiting the options available for device design. Summary of the Invention

[0006] In view of the above defects or improvement needs of the prior art, the present invention provides a nitrogen-containing heterocyclic compound, which exhibits excellent performance when used as an organic electroluminescent material, especially as an N-type charge generation layer material.

[0007] To achieve the above object, the present invention provides a nitrogen-containing heterocyclic compound having a structure shown in formula (1) or (2),

[0008]

[0009] In formulas (1) and (2), Ar1, Ar2, and Ar3 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms, at least one of Ar1-Ar3 is selected from a substituted or unsubstituted phenanthroline group, and at least one of Ar1-Ar3 is not a substituted or unsubstituted phenanthroline group;

[0010] Ar4 and Ar6 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms, and Ar5 is selected from a substituted or unsubstituted C6-C30 heteroarylene group containing at least two nitrogen atoms;

[0011] If Ar5 is selected from substituted or unsubstituted phenanthroline, then at least one of Ar4 and Ar6 is not a substituted or unsubstituted phenanthroline group;

[0012] If Ar5 is not a substituted or unsubstituted phenanthroline group, then at least one of Ar4 and Ar6 is selected from a substituted or unsubstituted phenanthroline group;

[0013] The substituents in the "substituted or unsubstituted" are independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 carbocyclyl, C3-C60 heterocyclyl,

[0014] The heteroatom in the heterocyclic group and the heteroaryl group is selected from at least one of N, O, S, Si and P.

[0015] Furthermore, in an optional embodiment of the present invention, the compound has a structure shown in any one of formulas (3) to (5),

[0016]

[0017] In formulas (3) to (5), R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl;

[0018] Ar1, Ar2, Ar4, Ar6 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms;

[0019] Ar5 is selected from a substituted or unsubstituted C6-C30 heteroarylene group containing at least two nitrogen atoms;

[0020] In formula (3), at least one of Ar1 and Ar2 cannot be selected from substituted or unsubstituted phenanthroline groups;

[0021] In formula (4), if Ar5 is selected from a substituted or unsubstituted phenanthroline group, then Ar4 cannot be selected from a substituted or unsubstituted phenanthroline group;

[0022] In formula (5), at least one of Ar4 and Ar6 cannot be selected from substituted or unsubstituted phenanthroline groups;

[0023] The substituents in the “substituted or unsubstituted” when substituted are independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 carbocyclyl, and C3-C60 heterocyclyl.

[0024] Furthermore, in an optional embodiment of the present invention, the compound is selected from the structure shown in formula (3),

[0025]

[0026] Wherein, R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl;

[0027] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms;

[0028] At least one of Ar1 and Ar2 cannot be selected from substituted or unsubstituted phenanthroline groups.

[0029] Furthermore, in an optional embodiment of the present invention, the compound is selected from the structure shown in formula (3),

[0030]

[0031] Wherein, R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl;

[0032] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted quinazoline group, or a substituted or unsubstituted phenanthroline group;

[0033] At least one of Ar1 to Ar2 is not selected from substituted or unsubstituted phenanthroline groups.

[0034] Preferably, R1 is selected from one of hydrogen, methyl, tert-butyl, phenyl and a combination of two or more of the above substituents.

[0035] More preferably, R1 is selected from hydrogen, tert-butyl, and phenyl.

[0036] Preferably, each of Ar1, Ar2is independently selected from the group consisting of substituted or unsubstituted:

[0037]

[0038] at least one of Ar1-Ar2is not selected from the group consisting of substituted or unsubstituted:

[0039]

[0040] More preferably, each of Ar1, Ar2is independently selected from the group consisting of substituted or unsubstituted:

[0041]

[0042] at least one of Ar1-Ar2is not selected from the group consisting of substituted or unsubstituted:

[0043]

[0044] Further, in an alternative embodiment of the present application, the compound is selected from the group consisting of formula (4) or (5),

[0045]

[0046] In formula (4)-(5), R1is selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10alkyl, substituted or unsubstituted C6-C60aryl;

[0047] each of Ar4, Ar6is independently selected from the group consisting of substituted or unsubstituted C6-C30heteroaryl comprising at least two nitrogen atoms; Ar5is selected from the group consisting of substituted or unsubstituted C6-C30heteroarylene comprising at least two nitrogen atoms;

[0048] and if Ar5is selected from the group consisting of substituted or unsubstituted phenanthrolinylene, then Ar4is not selected from the group consisting of substituted or unsubstituted phenanthrolinyl;

[0049] if Ar5is not selected from the group consisting of substituted or unsubstituted phenanthrolinylene, then Ar4is selected from the group consisting of substituted or unsubstituted phenanthrolinyl;

[0050] at least one of Ar4, Ar6is not selected from the group consisting of substituted or unsubstituted phenanthrolinyl;

[0051] the substituents in the "substituted or unsubstituted" are independently selected from the group consisting of deuterium, halogen, cyano, C1-C10alkyl, C3-C10cycloalkyl, C1-C10alkoxy, C2-C10alkenyl, C2-C10alkynyl, C6-C60aryl, C3-C60heteroaryl, C6-C60carbocyclyl, C3-C60heterocyclyl.

[0052] Furthermore, in an optional embodiment of the present invention, the compound is selected from the structure shown in formula (4) or (5),

[0053]

[0054] Wherein, R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl;

[0055] Ar4 and Ar6 are each independently selected from substituted or unsubstituted triazine, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinazoline, or substituted or unsubstituted phenanthroline;

[0056] Ar5 is selected from substituted or unsubstituted triazinylene, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrolinylene;

[0057] If Ar5 is selected from substituted or unsubstituted phenanthroline, then at least one of Ar4 and Ar6 is not a substituted or unsubstituted phenanthroline group;

[0058] If Ar5 is not a substituted or unsubstituted phenanthroline group, at least one of Ar4 and Ar6 is selected from a substituted or unsubstituted phenanthroline group.

[0059] Preferably, R1 is selected from one of hydrogen, methyl, tert-butyl, phenyl and a combination of two or more of the above substituents.

[0060] More preferably, R1 is selected from hydrogen, tert-butyl, and phenyl.

[0061] Preferably, Ar4 and Ar6 are each independently selected from the following substituted or unsubstituted groups:

[0062]

[0063] Ar5 is selected from the following substituted or unsubstituted groups:

[0064]

[0065] In formula (5), at least one of Ar4 and Ar6 cannot be selected from the following substituted or unsubstituted groups: In formula (4), if Ar5 is selected from the following substituted or unsubstituted groups: Ar4 cannot be selected from the following groups, substituted or unsubstituted:

[0066]

[0067] More preferably, Ar4 and Ar6 are each independently selected from the following substituted or unsubstituted groups:

[0068]

[0069] Ar5 is selected from the following substituted or unsubstituted groups:

[0070]

[0071] In formula (5), at least one of Ar4 and Ar6 cannot be selected from the following substituted or unsubstituted groups:

[0072]

[0073] In formula (4), if Ar5 is selected from the following substituted or unsubstituted groups: Ar4 cannot be selected from the following groups, substituted or unsubstituted:

[0074]

[0075] Furthermore, in an optional embodiment of the present invention, the compound is selected from the structures shown in numbers 1-81;

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] According to another aspect of the present invention, the present invention provides a use of the compound as an organic electroluminescent material.

[0084] An organic electroluminescent element comprises a first electrode, a second electrode and an organic layer between the first and second electrodes, wherein the organic layer comprises a light-emitting layer and the organic layer has one or more organic layers, at least one of which comprises the nitrogen-containing heterocyclic compound of the present invention.

[0085] Preferably, the organic layer comprises at least two light-emitting units, an N-type charge generation layer is included between the two light-emitting units, and the N-type charge generation layer comprises the nitrogen-containing heterocyclic derivative described in the present invention.

[0086] An electronic device includes one or more of a display, a monitor, and a lighting device, and includes the organic electroluminescent element of the present invention.

[0087] In general, the above technical solutions conceived by the present invention can achieve the following beneficial effects compared with the prior art:

[0088] 1. The nitrogen-containing heterocyclic compound of the present invention exhibits excellent performance when used as an organic electroluminescent material, especially as an N-type charge generation layer. The use of the nitrogen-containing heterocyclic compound of the present invention in the N-type charge generation layer of an organic electroluminescent element significantly improves the driving voltage and life of the element. BRIEF DESCRIPTION OF THE DRAWINGS

[0089] Figure 1 This is a schematic structural diagram of the organic electroluminescent device described in Application Example 1, wherein: a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a second hole transport layer 4, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an N-type charge generation layer 8, a P-type charge generation layer 9, a hole transport layer 10, a second hole transport layer 11, a light-emitting layer 12, a hole blocking layer 13, an electron transport layer 14, and a second electrode layer 15, wherein 100 is a first light-emitting unit and 200 is a second light-emitting unit. DETAILED DESCRIPTION

[0090] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the description set forth herein. Therefore, exemplary embodiments are described below only with reference to the accompanying drawings to illustrate aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind)" modify the entire list of elements when before or after a list of elements and do not modify the individual elements of the list.

[0091] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0092] It will be further understood that the terms “comprise” or “comprising” when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0093] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0094] The present invention will be further described below in conjunction with specific examples. It should be understood that these examples are intended only to illustrate the present invention and are not intended to limit the scope of protection of the present invention. In addition, it should be understood that after reading the disclosure of the present invention, those skilled in the art may make various changes or modifications to the present invention, and these equivalent forms also fall within the scope of protection defined by the present invention.

[0095] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the reagents, materials, etc. used in the following examples are all commercially available unless otherwise specified.

[0096] Explanation of terms

[0097] As used herein, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0098] As used herein, the term "C6-C14 aromatic ring" refers to an aromatic hydrocarbon ring having 6 to 14 carbon atoms, derived from a single ring or a combination of two or more rings, which may be fused with an adjacent ring, with the carbon atoms shared by the fused ring also being included in the 6 to 14 carbon atoms. The term "C10-C14 aromatic ring" should also be understood in the same manner.

[0099] As used herein, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0100] As used herein, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0101] As used herein, the term "C2-C10 heterocyclic group" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, and Si.

[0102] As used herein, the term "alkoxy" refers to a straight chain, branched chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, and benzyloxy.

[0103] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl group may have a form in which two or more rings are simply lateral to each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0104] As used herein, the term "arylene" refers to a divalent aromatic group derived from an "aryl" group by removing a hydrogen atom. For example, a phenyl group can be converted to a phenylene group by removing a hydrogen atom, and a naphthyl group can be converted to a naphthylene group by removing a hydrogen atom.

[0105] As used herein, the term "C3-C60 heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1-3 carbons, in the ring are substituted with a heteroatom, such as N, O, S, P, B or Si. In addition, such heteroaryl groups may have a form in which two or more rings are simply lateral to each other or fused to each other or to an aromatic group. Examples of such heteroaryl groups include, for example, pyrrolyl, furyl, thienyl, benzofuranyl, benzothienyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and the like, but the present invention is not limited thereto.

[0106] As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group can be converted into a pyridylene group by removing a hydrogen atom from a pyridyl group.

[0107] As used in the present invention, the "carbon number is MN" in the expression "a K group having a carbon number of MN" or "a K group of C(MN)" means the carbon number of the K group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C60 aryl group means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer between 6 and 60, that is, the carbon number when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0108] As used herein, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position where the substitution occurs can be the position where the hydrogen atom is replaced. That is, the position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. "Unsubstituted" means that the hydrogen atom remains. In this case, the hydrogen atom includes protium, deuterium, and tritium, and the substitution case may also include the case of deuterium and tritium substitution.

[0109] When two or more substituents are present, the two or more substituents may be the same or different.

[0110] As used in the present invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of the present invention may contain deuterium atoms from natural sources, or deuterium atoms may be introduced by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw materials, the deuteration rate may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be greater than 1%, or greater than 5%, or greater than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of a fully deuterated and incompletely deuterated compound, or a mixture of a fully deuterated and undeuterated compound and an incompletely deuterated compound.

[0111] As used in the present invention, terms such as first, second, A, and B are used. The above terms are only used to distinguish components and do not limit the nature or order of the components to which the terms correspond.

[0112] organic electroluminescent elements

[0113] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising an anode, a cathode and an organic layer located between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0114] The organic layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0115] The light-emitting element of the present invention may emit fluorescence, phosphorescence, or a combination thereof. The light-emitting element may emit light alone or in the form of a series connection of multiple light-emitting units.

[0116] As simple light emitting elements, the following may be mentioned, but are not limited to these:

[0117] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0118] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0119] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0120] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0121] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0122] (6) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer;

[0123] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0124] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0125] (9) hole transport layer / electron blocking layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer;

[0126] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0127] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0128] (12) hole injection layer / first hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0129] (13) hole injection layer / first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0130] The phosphorescent / fluorescent light-emitting layers may each emit light of a different color.

[0131] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also generally be called a charge generation layer, an electron extraction layer, a connecting layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer in order to prevent the excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or to adjust the balance of carriers.

[0132] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0133] The organic electroluminescent element of the present specification can be manufactured by using materials and methods known in the art, except that one or more of the organic material layers comprises the compound of the present invention.

[0134] Anode materials can be materials with relatively large work functions, including transparent conductive oxides, metals, and conductive polymers. Specific examples of anode materials include, but are not limited to, metals such as 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0135] Cathode materials typically use materials with a low work function to facilitate electron injection into the organic layer. Examples of cathode materials include metals, metal oxides, and conductive polymers. 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; and multilayer structures such as LiF / Al or LiO2 / Al.

[0136] The hole injection layer (HIL) injects holes from the electrodes and has the ability to transport them. To reduce the energy level difference between the electrodes, the HIL is primarily based on aromatic amine compounds. Other materials include copper phthalocyanine for metal complexes and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure for the lowest unoccupied molecular orbital (LUMO) energy level. When used as a luminescent host and dopant, F4-TCNQ (2,2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) derivatives with the lowest unoccupied molecular orbital (LUMO) energy level can be doped into aromatic amine compounds.

[0137] The first hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Aromatic amine derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0138] The second hole transport layer can adjust the energy difference between the hole transport region and the light-emitting layer, which is beneficial for holes to enter the light-emitting layer, while reducing the probability of electrons entering the hole transport region from the light-emitting layer. Aromatic amine derivatives are commonly used.

[0139] A luminescent material is a material that receives holes and electrons from the hole transport layer and electron transport layer, respectively, and combines the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a dopant material. Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. Both fluorescent and phosphorescent materials can be used as luminescent materials. The luminescent material can be a single-component material or a multi-component material.

[0140] The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can receive electrons from the cathode and transfer the electrons to the light-emitting layer. It is a material with high electron mobility. Triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used. Metal complexes, and polymer materials and small molecule materials can also be used.

[0141] The electron injection layer is a layer that injects electrons from the electrode.

[0142] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0143] Depending on the materials used, the organic light-emitting device of the present specification can be a top-emitting device, a bottom-emitting device, or a dual-emission device.

[0144] The charge generation layer (CGL) is the intermediate layer between the anode and cathode in a tandem-structured device. It generates holes and electrons through charge separation. The CGL typically consists of a P-type layer on the cathode side and an N-type layer on the anode side, enabling efficient charge separation and carrier transport.

[0145] In one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by vacuum evaporation, molecular beam evaporation (MBE), or by a known coating method such as dipping, spin coating, casting, rod coating, or roller coating of a solution dissolved in a solvent.

[0146] In one embodiment of the present invention, the film thickness of each layer is not particularly limited and can generally be several nanometers to several hundred nanometers. In order to suppress defects such as pinholes, reduce driving voltage, and improve luminous efficiency, it is usually preferably in the range of several nm to 1 μm.

[0147] The test instrument models used in the synthesis examples are as follows:

[0148] LC-MS brand: Waters, model: SQ Detector 2

[0149] NMR brand: Bruker, model: AVANCE NEO 400

[0150] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods. There are many methods for synthesizing the compounds of the present invention, and the following methods are only illustrative.

[0151] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods.

[0152] Synthesis Example:

[0153] Synthesis Example 1: Synthesis of Compound 25

[0154] Step 1: Synthesis of Intermediate 25-1

[0155]

[0156] Under a nitrogen atmosphere, 20.0 g of 2,4-dichloroquinazoline, 16.4 g of 3-chlorophenylboronic acid, 27.6 g of KCO, and 1.2 g of Pd(PPh) were placed in a four-necked flask. Toluene:H2O = 300:100 mL was added, and the mixture was heated to reflux and allowed to react for 3 hours. Samples were taken and sent for LC-MS analysis. Once the results were confirmed, the reaction was terminated and heating was stopped. After cooling, the mixture was extracted with dichloromethane and H2O and dried. Column chromatography (n-hexane:dichloromethane = 2:1 by volume) yielded 2-chloro-4-(3-chlorophenyl)quinazoline as a yellow-white solid, approximately 30 g wet weight, which was retained for later use.

[0157] LC-MS (APCI): 275.08 [M+H] +

[0158] Step 2: Synthesis of Intermediate 25-2

[0159]

[0160] Under a nitrogen atmosphere, the 2-chloro-4-(3-chlorophenyl)quinazoline obtained in step 1, 12.8g of phenylboric acid, 27.6g K2CO3 and 1.2g Pd(PPh3)4 were put into a four-necked flask, toluene:H2O=300:100mL was added, and the temperature was raised to reflux, and then kept warm for 3h. The sample point plate was taken and sent for inspection by LC-MS. After the test results were confirmed, the reaction was stopped and heating was stopped. After cooling, dichloromethane and H2O were extracted and spin-dried. Normal hexane:ethyl acetate=3:1 room temperature beating was performed once to obtain 4-(3-chlorophenyl)-2-phenylquinazoline 12g as a yellow-white solid and left for use.

[0161] LC-MS (APCI): 317.18 [M+H] +

[0162] Step 3: Synthesis of Intermediate 25-3

[0163]

[0164] Under a nitrogen atmosphere, place 12g of 4-(3-chlorophenyl)-2-phenylquinazoline (obtained in Step 2), 9.6g of bis-pinacol boronate, 11.2g of KOAc, and 348mg of Pd(dba) in a four-necked flask. Add 300mL of 1,4-dioxane and heat to reflux, then maintain for 4 hours. Samples were taken and sent for LC-MS analysis. Once the results were confirmed, the reaction was complete and heating was discontinued. After cooling, the mixture was extracted with dichloromethane and H2O and dried by spin drying. Column chromatography (n-hexane:dichloromethane = 3:1 by volume) yielded 8.8g of 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline as an off-white solid, which was retained for later use.

[0165] LC-MS (APCI): 409.34 [M+H] +

[0166] Step 4: Synthesis of Intermediate 25-4

[0167]

[0168] Under a nitrogen atmosphere, 8.1 g of 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline, 4.7 g of 2,9-dichlorophenanthroline, 5.2 g of KCO, and 220 mg of Pd(PPh) were placed in a four-necked flask. Toluene:H2O (180:60 mL) was added and the system was heated to reflux, then maintained at reflux for 3 hours. Samples were taken and sent for LC-MS analysis. Once the results were confirmed, the reaction was terminated and heating was discontinued. After cooling, the product was extracted with dichloromethane and H2O and dried by spin drying. Flash column chromatography using n-hexane:tetrahydrofuran (6:1) yielded 5 g of 2-chloro-9-(3-(2-phenylquinazolin-4-yl)phenyl)-1,10-phenanthroline as a white solid, which was retained for later use.

[0169] LC-MS (APCI): 495.32 [M+H] +

[0170] Step 5: Synthesis of compound 25

[0171]

[0172] Under a nitrogen atmosphere, 5 g of 2-chloro-9-(3-(2-phenylquinazolin-4-yl)phenyl)-1,10-phenanthroline, 4.4 g of 2,4-diphenyl-6-(3-phenylboronic acid pinacol ester)-1,3,5-triazine, 2.8 g of KCO, and 116 mg of Pd(PPh) were placed in a four-necked flask. Tetrahydrofuran:H2O:ethanol (210:70:20 mL) was added and the system was heated to reflux. The reaction was then allowed to proceed at this temperature for 3 h. Samples were taken and sent for LC-MS analysis. Once the results were confirmed, the reaction was terminated and heating was discontinued. After cooling, the product was extracted with dichloromethane and H2O and dried by spin drying. Column chromatography was performed (n-hexane:dichloromethane = 2:1 by volume). The product was then slurried three times with toluene and dried under vacuum to yield 3.2 g of the qualified compound 25.

[0173] LC-MS (APCI): 768.36 [M+H] +

[0174] 1H NMR(400MHz,Methylene Chloride-d2)δ9.71(s,1H),9.11(s,1H),8.93–8.69(m,9H),8.50(t,2H),8.39( dd,1H),8.28(d,1H),8.15(d,1H),7.94(d,3H),7.72(t,1H),7.68–7.51(m,13H).

[0175] Synthesis Example 2: Synthesis of Compound 4

[0176] Step 1: Synthesis of intermediate 4-1

[0177]

[0178] Under a nitrogen atmosphere, 2,4-bis(3-chlorophenyl)-6-phenyl-1,3,5-triazine (15 g, 39.78 mmol), bis-pinacol borate (30.34 g, 179.34 mmol), potassium acetate (15.59 g, 159.08 mmol), and dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium(II) (0.56 g, 0.79 mmol) were added to a 1,4-dioxane (150 mL) solution. The mixture was heated to 105°C for 6 h. Samples were taken and sent for LC-MS analysis. The reaction was completed after the results were confirmed. The product was directly filtered to obtain a white solid. The product was then slurried in toluene at 110°C to obtain 13 g of intermediate 4-1, with a yield of 59%.

[0179] LC-MS (APCI): 562.41 [M+H] +

[0180] Step 2: Synthesis of intermediate 4-2

[0181]

[0182] Under a nitrogen atmosphere, intermediate 4-1 (13.00 g, 25.18 mmol), 2-chloro-4-phenylquinazoline (6.06 g, 25.18 mmol), potassium carbonate (6.95 g, 50.35 mmol), and bis(triphenylphosphine)palladium dichloride (0.35 g, 0.50 mmol) were added to a 130 mL solution of tetrahydrofuran:water (volume ratio 3:1). The mixture was heated to 75°C and reacted for 6 h. The product was directly filtered to obtain a white solid. The mixture was then slurried with dichloromethane at 50°C to obtain 7.8 g of intermediate 4-2, with a yield of 48%.

[0183] LC-MS (APCI): 640.21 [M+H] +

[0184] Step 3: Synthesis of compound 4

[0185]

[0186] Under a nitrogen atmosphere, intermediate 4-2 (6.00 g, 9.39 mmol), 2-bromo-9-phenyl-1,10-phenanthroline (3.15 g, 9.39 mmol), potassium carbonate (2.60 g, 18.81 mmol), and bis(triphenylphosphine)palladium dichloride (0.20 g, 0.28 mmol) were added to a 60 mL solution of tetrahydrofuran:water (3:1). The mixture was heated to 75°C and reacted for 6 h. The product was directly filtered to obtain a white solid. The mixture was then slurried with dichloromethane at 50°C to obtain 5 g of compound 4, with a yield of 70%.

[0187] LC-MS (APCI): 768.36 [M+H] +

[0188] 1 H NMR(400MHz,Methylene Chloride-d2)δ10.19(t,1H),9.87(t,1H),9.02(ddt,2H),8.94(ddt,3H),8.84(dt,1H),8.48–8.43(m,2H),8.42–8.38(m,2H),8 .35(d,1H),8.20–8.14(m,2H),8.10(d,1H),7.97–7.88(m,6H),7.77(t,1H),7.69–7.61(m,4H),7.57(dd,3H),7.40–7.35(m,3H)

[0189] Synthesis Example 3: Synthesis of Compound 13

[0190]

[0191] Under a nitrogen atmosphere, 2-(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (7 g, 12.5 mmol), 2-bromo-9-phenyl-1,10-phenanthroline (8.56 g, 25.6 mmol), potassium carbonate (2.5 g, 24.9 mmol), and tetrakistriphenylphosphine palladium (720 mg, 0.6 mmol) were added to a four-necked reaction flask, and 75 ml of tetrahydrofuran and 25 ml of water were added. The temperature was raised to 70 ° C. and the reaction was carried out for 5 h. The sample point plate was taken and sent for LC-MS inspection. After the test results were confirmed, the solid was filtered at room temperature and slurried with ethyl acetate to obtain 6 g of solid with a yield of 60%.

[0192] LC-MS (APCI): 818.49 [M+H]+

[0193] 1 H NMR(400MHz,Methylene Chloride-d2)δ10.07(s,1H),9.95(d,2H),8.96–8.91(m,4H),8.64(d,2H),8.55(d,2H),8.50–8.45(m,4 H),8.40(d,2H),8.19(d,2H),7.98–7.90(m,4H),7.61(t,2H),7.55(dd,4H),7.28(dd,2H),7.21(dd,4H).

[0194] Synthesis Example 4: Synthesis of Compound 14

[0195] Step 1: Synthesis of Intermediate 14-1

[0196]

[0197] Under a nitrogen atmosphere, o-aminodiphenylamine (50.0 g, 271.35 mmol), 3-bromo-5-chlorobenzaldehyde (59.6 g, 271.35 mmol), and sodium bisulfite (28.2 g, 271.35 mmol) were added to a four-necked reaction flask, and 500 ml of N,N-dimethylformamide was added. The temperature was raised to reflux for 5 h, and the sample was taken and sent for LC-MS inspection. After the test results were confirmed and the reaction was completed, the reaction solution was cooled to room temperature, filtered and concentrated, and slurried with 100 ml of n-hexane to obtain intermediate 14-1 (50.0 g, 130.9 mmol).

[0198] LC-MS (APCI): 385.10 [M+H] +

[0199] Step 2: Synthesis of Intermediate 14-2

[0200]

[0201] Under a nitrogen atmosphere, intermediate 14-1 (50.0 g, 130.9 mmol), potassium acetate (38.5 g, 392.7 mmol), pinacol diboron (33.2 g, 130.9 mmol), and 1,1-bis(diphenylphosphino)diphenylferric palladium chloride (1.63 g, 2.22 mmol) were added to a four-necked reaction flask. 400 ml of anhydrous 1,4-dioxane was added, and the temperature was raised to strong reflux. The reaction was allowed to proceed for 12 h. Samples were taken and sent for LC-MS analysis. After confirmation of the results, the reaction solution was cooled to room temperature, filtered, and concentrated. Column chromatography (n-hexane:dichloromethane = 4:1 by volume) was performed to obtain intermediate 14-2 (40.0 g, 93.0 mmol).

[0202] LC-MS (APCI): 431.15 [M+H] +

[0203] Step 3: Synthesis of Intermediate 14-3

[0204]

[0205] Under a nitrogen atmosphere, intermediate 14-2 (30.0 g, 69.8 mmol), potassium acetate (20.5 g, 209.4 mmol), pinacol diboron (17.7 g, 69.8 mmol), and dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium(II) (1.57 g, 2.22 mmol) were added to a four-necked reaction flask. 300 ml of anhydrous 1,4-dioxane was added and the mixture was heated to strong reflux for 12 h. Samples were taken and sent for LC-MS analysis. After confirmation of the results, the reaction solution was cooled, filtered, and concentrated. Column chromatography (n-hexane:dichloromethane = 4:1 by volume) was performed to obtain intermediate 14-3 (20.0 g, 38.31 mmol).

[0206] LC-MS (APCI): 523.19 [M+H] +

[0207] Step 4: Synthesis of compound 14

[0208]

[0209] Under a nitrogen atmosphere, intermediate 14-3 (10.0 g, 19.15 mmol), 2-bromo-9-phenyl-1,10-phenanthroline (12.8 g, 0.383 mmol), 1,1-bis(diphenylphosphine)diphenylferric palladium dichloride (0.28 g, 2.22 mmol), and potassium carbonate (3.58 g, 25.95 mmol) were placed in a four-necked reaction flask, and 100 ml of tetrahydrofuran and 30 ml of water were added. The mixture was heated to reflux for 4 h, and the sample was taken and sent to LC-MS for inspection. After the test results were confirmed, the temperature was cooled to room temperature and filtered to obtain compound 14 (8.00 g, 10.28 mmol).

[0210] LC-MS (APCI): 779.39 [M+H] +

[0211] 1H NMR(400MHz,Methylene Chloride-d2)δ9.85–9.78(m,1H),8.75–8.67(m,2H),8.43–8.35(m,4H),8.30(ddd,4 H),8.06(ddd,4H),7.90(dd,1H),7.81(d,4H),7.53–7.42(m,4H),7.41–7.21(m,10H).

[0212] Synthesis Example 5: Synthesis of Compound 23

[0213] Step 1: Synthesis of Intermediate 23-1

[0214]

[0215] Under a nitrogen atmosphere, 2-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20 g, 42.57 mmol), 2-chloro-1-phenyl-1H-benzo[d]imidazole (10.7 g, 46.83 mmol), potassium carbonate (11.8 g, 85.14 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.13 mmol), tetrahydrofuran (200 ml), and water (50 ml) were added to a four-necked flask in sequence. The reaction was refluxed for 6 hours. The sample was taken and sent for LC-MS inspection. After the test results were confirmed, the reaction was completed and the water was separated (heterogeneous reaction, the reaction was allowed to stand after completion and the aqueous phase was separated). After concentration, the mixture was slurried with ethyl acetate to obtain intermediate 23-1 (19.1 g, 35.62 mmol).

[0216] LC-MS (APCI): 536.25 [M+H] +

[0217] Step 2: Synthesis of Intermediate 23-2

[0218]

[0219] Under a nitrogen atmosphere, intermediate 23-1 (19.1 g, 35.62 mmol), diboronic acid pinacol ester (10.8 g, 42.74 mmol), potassium acetate (7.0 g, 71.24 mmol), palladium acetate (400 mg, 1.78 mmol), tricyclohexylphosphine tetrafluoroborate (1.3 g, 3.56 mmol), and 1,4-dioxane (300 ml) were added to a four-necked flask in sequence. The reaction was refluxed overnight, and the sample was taken and sent for LC-MS inspection. After the test results were confirmed, the reaction was completed and passed through a flash column. After concentration, the solution was slurried with n-hexane to obtain intermediate 23-2 (15.6 g, 24.91 mmol).

[0220] LC-MS (APCI): 628.38 [M+H] +

[0221] Step 3: Synthesis of compound 23

[0222]

[0223] Under a nitrogen atmosphere, intermediate 23-2 (15.6 g, 24.91 mmol), 2-bromo-9-phenyl-1,10-phenanthroline (9.2 g, 27.40 mmol), potassium carbonate (6.9 g, 49.82 mmol), tetrakis(triphenylphosphine)palladium (1.4 g, 1.24 mmol), tetrahydrofuran (200 ml), and water (50 ml) were added sequentially into a four-necked flask. The mixture was refluxed under nitrogen for 3 hours. After the reaction was completed, water was separated and the mixture was recrystallized from toluene to obtain compound 23 (14.0 g, 18.56 mmol).

[0224] LC-MS (APCI): 756.42 [M+H] +

[0225] 1 H NMR(400MHz,Methylene Chloride-d2)δ9.77(t,1H),9.24(t,1H),8.81(t,1H),8.74–8.67(m,4H),8.50–8.45(m,2H),8.42(d,1H),8.36(d,1H),8.25( d,1H),8.20(d,1H),7.99(dt,1H),7.84(s,2H),7.63–7.51(m,10H),7.49–7.41(m,2H),7.38–7.35(m,2H),7.35–7.30(m,3H).

[0226] The following application examples further illustrate the application of the nitrogen-containing fused ring compound of the present invention in the preparation of organic electroluminescent elements.

[0227] Application Example 1:

[0228] This embodiment provides an organic electroluminescent element, such as Figure 1 As shown, it includes a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a second hole transport layer 4, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an N-type charge generation layer 8, a P-type charge generation layer 9, a hole transport layer 10, a second hole transport layer 11, a light-emitting layer 12, a hole blocking layer 13, an electron transport layer 14, and a second electrode layer 15, which are stacked in sequence, wherein 100 is a first light-emitting unit and 200 is a second light-emitting unit.

[0229] The specific device structure is:

[0230] ITO / HT1:PD(3%)(10nm) / HT1(60nm) / HT2(5nm) / ADN:BD(3%)(20nm) / HB(5nm) / ET-Li q(50%)(10nm) / REF-1:Li(2%)(10nm) / HT1:PD(10%)(10nm) / HT1(60nm) / HT2(5nm) / ADN:BD(3%)(20nm) / HB(5nm) / ET-Liq(50%)(20nm) / Mg:Ag 1:9(100nm).

[0231] Device preparation process:

[0232] The bottom-emitting glass substrate 1 used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and ITO was used as the anode 2. First, the bottom-emitting glass substrate was cleaned using an ITO cleaner, deionized water, and isopropyl alcohol in that order, and then baked at 180 degrees Celsius for 30 minutes to dry it.

[0233] Then put the bottom luminescent glass substrate into the evaporation chamber and -8Under the condition of support, each organic layer is deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second. Among them, PD (3%) is doped into HT1 to form a thickness of 10nm as a hole injection layer. HT1 is formed to a thickness of 60nm as a hole transport layer, and a 5nm layer of HT2 material is evaporated thereon as a second hole transport layer. Then, 3% BD is doped on the anthracene main body ADN (9,10-di(naphtha-2-yl-) anthracene) to form a blue light-emitting layer with a thickness of 20nm, and 5nm HB is evaporated thereon as a hole blocking material. ET is doped with 50% Liq to form a thickness of 10nm as an electron transport layer. 2% Li is doped in REF-1 to form a 10nm thick N-type charge generation layer 8. 10% PD is doped in HT1. A 10nm thick P-type charge generation layer was formed. HT1 was formed to a 60nm thickness as a hole transport layer. A 5nm layer of HT2 was evaporated on top as a second hole transport layer. A 20nm thick blue light-emitting layer was formed by evaporating anthracene (ADN) (9,10-di(naphtha-2-yl-)anthracene) doped with 3% BD. 5nm of HB was evaporated on top as a hole-blocking material. ET was doped with 50% Liq to a thickness of 20nm as an electron transport layer. Mg:Ag (1:9) was formed to a thickness of 100nm as cathode 9. In this device embodiment, different materials were co-evaporated in the same layer, with the layers present in a certain volume ratio. For example, 50% Liq would have a volume ratio of 50% ET to 50% Liq. The material of this invention was purified by sublimation before use, with an HPLC score of 99.9%.

[0234] Finally, the device was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device, which was designated as organic electronic element 1 (comparative example).

[0235] The specific structures of the compounds involved are as follows:

[0236]

[0237]

[0238] Comparative Example 1 (REF-1) Structure:

[0239]

[0240] Examples and Comparative Examples

[0241] The N-type charge generation layer 8 was prepared by using the compound 25 prepared in Example 1 of the present invention instead of the Bphen material, and the organic electronic element 2 was prepared using the same method.

[0242] The N-type charge generation layer 8 was prepared by using the compound 4 prepared in Example 2 of the present invention instead of the Bphen material, and the organic electronic element 3 was prepared by the same method.

[0243] The N-type charge generation layer 8 was prepared by using the compound 13 prepared in Example 3 of the present invention instead of the Bphen material, and the organic electronic element 4 was prepared by the same method.

[0244] The N-type charge generation layer 8 was prepared by using the compound 14 prepared in Example 5 of the present invention instead of the Bphen material, and the organic electronic element 5 was prepared by the same method.

[0245] The N-type charge generation layer 8 was prepared by using the compound 23 prepared in Example 5 of the present invention instead of the Bphen material, and the organic electronic element 6 was prepared by the same method.

[0246] Organic electroluminescent device evaluation

[0247] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[0248] Current efficiency at current density 15mA / cm 2 Next test.

[0249] The driving voltage is at a current density of 15 mA / cm 2 Next test.

[0250] Drive voltage, V Current efficiency, cd / A Lifespan, LT95 Organic electronic components1 7.53 12.5 80 Organic electronic components2 7.25 12.5 138.2 Organic electronic components3 7.31 12.5 136.0 Organic electronic components4 7.39 12.5 135.8 Organic electronic components5 7.37 12.5 135.5 Organic electronic components6 7.39 12.5 137.9

[0251] Compared with the organic electronic element 1, the organic electroluminescent elements 2-6 prepared from the nitrogen-containing heterocyclic compounds of the present application have lower driving voltages and longer service lives. In particular, the driving voltage of the organic electroluminescent element 2-3 is more significantly reduced than that of the organic electronic element 1. Therefore, the compounds of the present invention are suitable for preparing high-performance organic electroluminescent elements.

[0252] It will be easily understood by those skilled in the art that the above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions and improvements made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A nitrogen-containing heterocyclic compound, characterized in that The compound has a structure represented by formula (1) or (2), In formulae (1) and (2), Ar1, Ar2, and Ar3 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms, at least one of Ar1 to Ar3 is selected from a substituted or unsubstituted phenanthroline group, and at least one of Ar1 to Ar3 is not selected from a substituted or unsubstituted phenanthroline group; Ar4 and Ar6 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms, and Ar5 is selected from a substituted or unsubstituted C6-C30 heteroarylene group containing at least two nitrogen atoms. If Ar5 is selected from substituted or unsubstituted phenanthroline, then at least one of Ar4 and Ar6 is not selected from substituted or unsubstituted phenanthroline; If Ar5 is not selected from substituted or unsubstituted phenanthroline, then at least one of Ar4 and Ar6 is selected from substituted or unsubstituted phenanthroline; The substituents in the "substituted or unsubstituted" are independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 carbocyclyl, C3-C60 heterocyclyl, The heteroatom in the heterocyclic group and the heteroaryl group is selected from at least one of N, O, S, Si and P.

2. A nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The compound has a structure shown in any one of formulas (3) to (5), In formulas (3) to (5), R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C60 aryl; Ar1, Ar2, Ar4, Ar6 are each independently selected from a substituted or unsubstituted C6-C30 heteroaryl group containing at least two nitrogen atoms; Ar5 is selected from a substituted or unsubstituted C6-C30 heteroarylene group containing at least two nitrogen atoms; In formula (3), at least one of Ar1 and Ar2 is not selected from substituted or unsubstituted phenanthroline groups; In formula (4), if Ar5 is selected from substituted or unsubstituted phenanthroline, then Ar4 is not selected from substituted or unsubstituted phenanthroline; In formula (5), at least one of Ar4 and Ar6 is not selected from substituted or unsubstituted phenanthroline groups; The substituents in the "substituted or unsubstituted" are independently selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 carbocyclyl, and C3-C60 heterocyclyl.

3. A nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The compound is selected from the structure shown in formula (3), wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted quinazoline group, or a substituted or unsubstituted phenanthroline group; At least one of Ar1-Ar2 is not a substituted or unsubstituted phenanthroline group; R1 is selected from hydrogen, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C60 aryl group.

4. A nitrogen-containing heterocyclic compound according to claim 3, characterized in that, Ar1 and Ar2 are each independently selected from the following substituted or unsubstituted groups: At least one of Ar1-Ar2 is not selected from the following substituted or unsubstituted groups:

5. A nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The compound is selected from the structure shown in formula (4) or (5), wherein Ar4 and Ar6 are each independently selected from substituted or unsubstituted triazine, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinazoline, or substituted or unsubstituted phenanthroline; Ar5 is selected from substituted or unsubstituted triazinylene, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthrolinylene; In formula (4), if Ar5 is selected from a substituted or unsubstituted phenanthroline group, then Ar4 cannot be selected from a substituted or unsubstituted phenanthroline group; In formula (5), Ar4 and Ar6 cannot be simultaneously selected from substituted or unsubstituted phenanthroline groups; R1 is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C60 aryl.

6. A nitrogen-containing heterocyclic compound according to claim 5, characterized in that, Ar4 and Ar6 are each independently selected from the following substituted or unsubstituted groups: Ar5 is selected from the following substituted or unsubstituted groups: In formula (4), if Ar5 is selected from the following substituted or unsubstituted groups: Ar4 cannot be selected from the following substituted or unsubstituted groups: In formula (5), at least one of Ar4 and Ar6 cannot be selected from the following substituted or unsubstituted groups:

7. A nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The compound is selected from the structures shown in numbers 1-81; 8. An organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, characterized in that: The organic layer has one or more layers, and at least one organic layer comprises the nitrogen-containing heterocyclic compound according to any one of claims 1 to 7.

9. The organic electroluminescent element according to claim 8, wherein: The organic layer includes at least two light-emitting units, an N-type charge generation layer is included between the two light-emitting units, and the N-type charge generation layer includes the nitrogen-containing heterocyclic compound according to any one of claims 1 to 7.

10. An electronic device comprising: One or more of a display, a monitor, and a lighting device, comprising the organic electroluminescent element according to claim 8 or 9.

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