Nitrogen-containing compounds, organic electroluminescent devices and electronic devices

Abstract

The present application relates to the technical field of organic electroluminescent materials, and provides a nitrogen-containing compound and an organic electroluminescent device and an electronic device containing the same. The compound of the present application uses a pentahedral fused indole as the core structure of the compound. When the compound of the present application is used as the main material of the light-emitting layer, the carrier balance in the light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the luminous efficiency and life of the device can be improved.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to nitrogen-containing compounds and organic electroluminescent devices and electronic devices containing the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide a nitrogen-containing compound and an electronic component and an electronic device containing the same. The nitrogen-containing compound is used in an organic electroluminescent device to improve the performance of the device.

[0005] According to a first aspect of the present application, a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure shown in the following formula 1:

[0006]

[0007] Wherein, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0008] Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;

[0009] Ar1 and Ar2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0010] Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;

[0011] n1 is selected from 0, 1, 2, 3 or 4;

[0012] n2 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0013] n3 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0014] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0015] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.

[0016] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0017] The compound of the present application uses a pentahedral fused indole as the parent core structure, and the parent core is connected to an electron-deficient heteroaryl group, as a single-type red light host material or an electron-transporting host material in a mixed red light host material. On the one hand, the parent core of the pentahedral fused indole has a large conjugated system, and after connecting it to an electron-deficient heteroaryl group, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the pentahedral are staggered from each other due to steric hindrance, and are located in the upper and lower planes respectively, thereby being able to suppress the stacking and accumulation of molecules to a certain extent, thereby improving the film-forming property of the compound. When the compound of the present application is used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0019] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0020] Figure 2 It is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.

[0021] Reference numerals

[0022] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0023] 321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer

[0024] 350. Electron injection layer 400. Electronic device DETAILED DESCRIPTION

[0025] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed 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, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0026] In a first aspect, the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:

[0027]

[0028] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0029] Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;

[0030] Ar1 and Ar2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0031] Each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;

[0032] n1 is selected from 0, 1, 2, 3 or 4;

[0033] n2 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0034] n3 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0035] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents may form a saturated or unsaturated 3 to 15-membered ring.

[0036] In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "L, L1, L2, Ar1 and Ar2, optionally, any two adjacent substituents form a ring" means that any two adjacent substituents in L, L1, L2, Ar1 and Ar2 are connected to each other to form a ring, or any two adjacent substituents in Ar1 and Ar2 can also exist independently. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms having one substituent respectively; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on two adjacent atoms respectively, the two substituents can be fused into a ring.

[0037] In this application, the descriptions "each ... independently is" and "... independently is" and "... independently is" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example,

[0038] Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and 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, and the number q of R" substituents 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.

[0039] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the 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 above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be 1 or more.

[0040] In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.

[0041] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0042] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0043] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by carbon-carbon single bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon single bond conjugation, two or more condensed ring aryl connected by carbon-carbon single bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon single bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl 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, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0044] In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0045] In the present application, terphenyl includes

[0046] In the present application, the number of carbon atoms of a 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 the total number of carbon atoms of the aryl group and the substituents is 18.

[0047] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38 or 40, etc. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 40 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.

[0048] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0049] In the present application, the aryl group as a substituent of L, L1, L2, Ar1 and Ar2 includes, but is not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0050] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon single bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0051] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0052] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 40, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5 to 12.

[0053] In the present application, the heteroaryl group as a substituent of L, L1, L2, Ar1 and Ar2 is, for example but not limited to, pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.

[0054] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. 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.

[0055] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0056] In the present application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.

[0057] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0058] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0059] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0060] In the present application, a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to, a deuterated phenyl group, a deuterated naphthyl group, a deuterated biphenyl group, and the like.

[0061] In the present application, the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.

[0062] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0063] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0064]

[0065] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0066]

[0067] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

[0068]

[0069] In some embodiments, each R1, R2 and R3 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0070] In some embodiments, Het is selected from the following groups:

[0071]

[0072] -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

[0073] In some embodiments, Het is selected from the following groups:

[0074]

[0075] -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In the above formula, L2 is a single bond and Ar2 is hydrogen.

[0076] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0077] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0078] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.

[0079] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted dibenzothiophenylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.

[0080] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0081] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:

[0082]

[0083] In some embodiments, L is selected from a single bond or the following groups:

[0084]

[0085] In some embodiments, L1 and L2 are each independently selected from a single bond or the following groups:

[0086]

[0087] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0088] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0089] In some embodiments, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0090] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;

[0091] Ar2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0092] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, in Ar1 and Ar2, any two adjacent substituents form a benzene ring or a fluorenyl ring.

[0093] In some embodiments, Ar1 is selected from a substituted or unsubstituted group V; Ar2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups:

[0094]

[0095] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group V is greater than 1, the substituents are the same or different.

[0096] In some embodiments, Ar1 is selected from the following groups; Ar2 is selected from hydrogen or the following groups:

[0097]

[0098]

[0099] In some embodiments, in Formula 1 Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:

[0100]

[0101] In some embodiments, in Formula 1 Selected from the group consisting of:

[0102]

[0103]

[0104]

[0105] In some embodiments, Het is selected from: -# indicates the bond connected to L, represents the bond connected to L1, represents a bond to L2, and

[0106] Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,

[0107] Ar2 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,

[0108] The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; or

[0109] Het is selected from:

[0110] -# indicates the bond connected to L, represents a bond to L1, and

[0111] Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,

[0112] The substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0113] In some embodiments, the nitrogen-containing compound is selected from the group consisting of:

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] In a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.

[0123] The nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0124] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound. The organic light-emitting layer can be composed of the nitrogen-containing compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials.

[0125] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.

[0126] In the present application, the anode 100 includes an anode material, which is preferably a material 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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined 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 not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0127] In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:

[0128]

[0129]

[0130] In one embodiment, the hole transport layer 321 may be composed of HT-1.

[0131] In one embodiment, the electron blocking layer 322 is composed of HT-2.

[0132] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;

[0133]

[0134] In one embodiment, the hole injection layer 310 is composed of PD and HT-1.

[0135] In the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and 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.

[0136] The host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. Optionally, the host material includes the nitrogen-containing compound of the present application.

[0137] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,

[0138]

[0139]

[0140] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The guest material is, for example, RD-1. In another embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application and The guest material is, for example, RD-1.

[0141] In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The guest material is, for example, fac-Ir(ppy)3.

[0142] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this. The materials of the electron transport layer 340 include but are not limited to the following compounds:

[0143]

[0144] In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.

[0145] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. 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 their alloys; 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 is included as the cathode.

[0146] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).

[0147] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0148] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0149] The synthesis method of the nitrogen-containing compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereby.

[0150] Synthesis Example

[0151] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.

[0152] Synthesis of Sub-a1:

[0153]

[0154] Under nitrogen atmosphere, RM-1 (25.0 g, 70 mmol) and tetrahydrofuran (dry, 250 mL) were added to a 500 mL three-necked flask; the system was cooled to -78 °C, and n-butyl lithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the mixture was kept warm (-78 °C) and stirred for 1 hour; trimethyl borate (10.91 g, 105 mmol) was added dropwise at -78 °C, and the mixture was kept warm (-78 °C) for 1 hour after the addition was complete, and then the system was allowed to warm up to room temperature naturally; dilute hydrochloric acid (2 M, 58 mL) was added dropwise to the reaction solution and stirred for 30 minutes; dichloromethane extraction (100 mL × 3 times) was performed, the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product; the crude product was slurried with n-heptane and filtered to obtain a white solid product (13.98 g, 62%).

[0155] Synthesis of Sub-b1:

[0156]

[0157] Under nitrogen atmosphere, o-bromonitrobenzene (10.0 g, 50 mmol), Sub-a1 (17.72 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (200 mL), anhydrous ethanol (50 mL) and deionized water (50 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phase was dried with anhydrous magnesium sulfate, filtered and distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a yellow solid (14.75 g, yield 74%).

[0158] Synthesis of Sub-c1:

[0159]

[0160] Under nitrogen atmosphere, add Sub-b1 (20.0 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol) and o-dichlorobenzene (160 mL) to a 250 mL three-necked flask, start stirring and heating, and raise the temperature to reflux reaction for 16 hours. After the system is cooled to room temperature, the solvent is removed by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid Sub-c1 (10.5 g, yield 57%).

[0161] Synthesis of Sub-c2:

[0162]

[0163] Under nitrogen atmosphere, add Sub-c1 (9.18g, 25mmol) and 200mL benzene-D6 to a 100mL three-necked flask, heat to 60°C, add trifluoromethanesulfonic acid (22.51g, 150mmol), continue to heat to boiling and stir for 24 hours. After the reaction system is cooled to room temperature, add 50mL of heavy water, stir for 10 minutes, and then add saturated K3PO4 aqueous solution to neutralize the reaction solution. Extract the organic layer with dichloromethane (50mL×3 times), combine the organic phases, dry them with anhydrous sodium sulfate, filter and distill under reduced pressure to remove the solvent to obtain a crude product. Use n-heptane / dichloromethane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid (5.07g, yield 53%).

[0164] Sub-d1 Synthesis:

[0165]

[0166] Under nitrogen atmosphere, RM-2 (17.10 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (160 mL), anhydrous ethanol (40 mL) and deionized water (40 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phase was dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (17.14 g, yield 82%).

[0167] Referring to the synthesis of Sub-d1, reactant A shown in Table 1 was used to replace RM-2, and reactant B was used to replace 4-chlorophenylboronic acid to synthesize Sub-d2 to Sub-d10.

[0168] Table 1: Synthesis of Sub-d2 to Sub-d10

[0169]

[0170]

[0171]

[0172] Synthesis of compound 4:

[0173]

[0174] Sub-1 (18.35 g, 50 mmol), RM-3 (26.80 g, 75 mmol) and dry DMF (400 mL) were added to a 1000 mL three-necked flask in sequence, the system was cooled to -10 °C, sodium hydrogen (60% content, 2.2 g, 55 mmol) was quickly added, and the reaction was stirred overnight. The reaction solution was poured into 500 mL of deionized water, stirred for 30 min and then filtered, the filtered solid was washed with deionized water until neutral, and then rinsed with anhydrous ethanol (200 mL) to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (23.0 g, yield 67%, m / z = 689.3 [M+H] + ).

[0175] Referring to the synthesis of compound 4, reactant C was used to replace Sub-c1, and reactant D was used to replace RM-3 as shown in Table 2 to synthesize the compounds of the present application in Table 2.

[0176] Table 2: Synthesis of compounds of the present application

[0177]

[0178]

[0179]

[0180] Synthesis of compound 110:

[0181]

[0182] Under nitrogen atmosphere, Sub-c1 (18.35 g, 50 mmol), Sub-d1 (23.0 g, 55 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-Phos, 0.95 g, 2 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 100 mm ol) and xylene (xylene, 250mL), heated to reflux, stirred and reacted overnight; after the system was cooled to room temperature, the reaction solution was poured into 500mL deionized water, stirred thoroughly for 30 minutes, filtered, the filter cake was rinsed with deionized water until neutral, and then rinsed with anhydrous ethanol (200mL) to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (25.10g, yield 67%, m / z=750.3[M+H] + ).

[0183] Referring to the synthesis of compound 110, reactant E shown in Table 3 was used to replace Sub-d1 to synthesize the compounds of the present application in Table 3.

[0184] Table 3: Synthesis of compounds of the present application

[0185]

[0186]

[0187]

[0188] Compound 7 NMR: 1H-NMR(400MHz,Methylene-Chloride-D2)δppm 8.66(d,1H),8.58(d,1H),8.54-8.49(m,4H),8.40(d,1H),8.25(d,1H),8.07-7.86(m,8H),7.61-7.32(m,11H),7.26(t,1H);

[0189] Compound 193 NMR: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 8.58(d,1H),8.46(d,1H),8.31(d,1H),8.16(s,1H),8.12-7.80(m,14H),7.60-7.54(m,4H),7.52-7.42(m,3H),7.37-7.27(m,2H).

[0190] Preparation and evaluation of organic electroluminescent devices:

[0191] Example 1: Red organic electroluminescent device

[0192] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0193] PD was vacuum-deposited on the experimental substrate (anode) to form a A hole injection layer (HIL) is then formed by vacuum evaporating HT-1 to a thickness of hole transport layer.

[0194] Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0195] Next, compound 4:RH-P:RD was co-deposited on the electron blocking layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of The red light emitting layer (EML)

[0196] On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0197] In addition, CPL-1 is vacuum-evaporated on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.

[0198] Embodiments 2 to 27

[0199] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound X in Table 4 below was used instead of Compound 4 in Example 1 when preparing the light-emitting layer.

[0200] Comparative Examples 1 to 3

[0201] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 4 in Example 1 when preparing the light-emitting layer.

[0202] Among them, in each embodiment and comparative example, the compound structure used is as follows:

[0203]

[0204] The performance of the red organic electroluminescent devices prepared in Examples 1 to 27 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 4.

[0205] Table 4

[0206]

[0207]

[0208] Referring to Table 4 above, it can be seen that when the compound of the present invention is used as an electron transport host material in a mixed red light host material, compared with Comparative Examples 1 to 3, the luminous efficiency of the device is increased by at least 13.6%, and the T95 life is increased by at least 14.8%.

[0209] Example 28: Red organic electroluminescent device

[0210] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface treatment was carried out using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0211] On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a layer with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0212] Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0213] Next, compound 110:RD-1 was co-deposited on the electron blocking layer at a deposition rate ratio of 98%:2% to form a layer with a thickness of The red light emitting layer (EML)

[0214] On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0215] In addition, CPL-1 is vacuum-evaporated on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.

[0216] Embodiments 28 to 38

[0217] An organic electroluminescent device was prepared by the same method as in Example 28, except that compound Y in the following Table 5 was used instead of compound 110 in Example 28 when preparing the light-emitting layer.

[0218] Comparative Examples 4 to 6

[0219] An organic electroluminescent device was prepared by the same method as in Example 28, except that compound D, compound E and compound F were used respectively to replace compound 110 in Example 28 when preparing the light-emitting layer.

[0220] Among them, in Examples 28 to 38 and Comparative Examples 4 to 6, the structures of the compounds used are as follows:

[0221]

[0222]

[0223] The performance of the red organic electroluminescent devices prepared in Examples 28 to 38 and Comparative Examples 4 to 6 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 5.

[0224] Table 5

[0225]

[0226] Referring to Table 5 above, it can be seen that when the compound of the present invention is used as the host material of the red organic electroluminescent device, compared with Comparative Examples 4 to 6, the luminous efficiency of the device is increased by at least 13.2%, and the life span is increased by at least 11.3%.

[0227] The structure of the compound of the present application contains a parent core structure of a five-spiralene-fused indole, and the parent core is connected to an electron-deficient heteroaryl group through a connecting group, as a single-type red light host material or an electron-transporting host material in a mixed host material. On the one hand, the parent core of the five-spiralene-fused indole has a large conjugated system, and after connecting it with triazine, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the five-spiralene are staggered from each other due to steric hindrance, and are located in the upper and lower planes respectively, thereby being able to suppress the stacking and accumulation of molecules to a certain extent and improve the film-forming property of the compound. When the compound of the present application is used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.

[0228] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. A nitrogen-containing compound, characterized in that It has a structure shown in the following formula 1: Wherein, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group; The substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl; Het is selected from the following groups: Among them, -# indicates the bond connected to L, represents the bond connected to L1, Represents a bond connected to L2; the formula does not contain , which represents the location connected to In, L2 is a single bond and Ar2 is hydrogen; Ar1 is selected from a substituted or unsubstituted group V; Ar2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups: The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents on the group V is greater than 1, each substituent is the same or different; each R1, R2 and R3 are the same or different and are each independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1, 2, 3, 4, 5 or 6; n3 is selected from 0, 1, 2, 3, 4, 5 or 6.

2. The nitrogen-containing compound according to claim 1, wherein Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:

3. The nitrogen-containing compound according to claim 1, wherein In formula 1 Selected from the group consisting of:

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

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

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

7. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to claim 5 or 6.

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