Nitrogen-containing compound and organic electroluminescent device and electronic device using the same

Abstract

This application belongs to the field of organic electroluminescence technology and relates to a nitrogen-containing compound and an organic electroluminescent device and electronic device using the same. The nitrogen-containing compound has a structure as shown in Formula 1. Using the nitrogen-containing compound in an organic electroluminescent device can significantly improve the device performance. #imgabs0#

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to a nitrogen-containing compound and an organic electroluminescent device and an electronic device using the same. Background Art

[0002] In recent years, self-luminous organic light-emitting diodes (OLEDs), which can be driven by low voltages, have attracted significant attention as a next-generation display element, compared to mainstream flat-panel displays (LCDs). These diodes offer superior viewing angle and contrast, require no backlight, and are therefore lightweight and thin, consume little power, and offer a wide range of color reproduction. While many substances have been disclosed for use in OLEDs, OLEDs utilizing these substances have been hindered by their high drive voltages, low efficiency, and short lifespans. Therefore, the development of substances with superior properties is needed to achieve low-voltage drive, high brightness, and long-life OLEDs. Summary of the Invention

[0003] The purpose of the present application is to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device using the same, which have high luminous efficiency and service life.

[0004] In order to achieve the above-mentioned object, the first aspect of the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:

[0005]

[0006] Wherein, A has the structure shown in Formula 2;

[0007] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0008] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0009] X is O or S;

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

[0011] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n1 is greater than 1, any two R1 are the same or different;

[0012] n2 represents the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different;

[0013] n3 represents the number of R3, n3 is selected from 0, 1, 2, 3 or 4, when n3 is greater than 1, any two R3 are the same or different;

[0014] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms or a deuterated alkyl group having 1 to 10 carbon atoms.

[0015] The second aspect of the present application provides 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; the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application;

[0016] Preferably, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the nitrogen-containing compound;

[0017] Preferably, the organic electroluminescent device is a green organic electroluminescent device.

[0018] 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.

[0019] Through the above technical solution, the present application provides a nitrogen-containing compound with a core structure composed of a combination of 3,3-bicarbazole and benzoxazole / benzothiazole groups. 3,3-bicarbazole has excellent hole transport properties, and when combined with benzoxazole / benzothiazole, which has electronic properties, the material can have relatively balanced carrier transport properties. The attachment of benzoxazole / benzothiazole to one of the carbazole rings in 3,3-bicarbazole can give the material a suitable T1 energy level, thereby enhancing the exciton energy transfer effect. When used as a light-emitting layer material in an organic electroluminescent device, it can significantly improve device performance.

[0020] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] The accompanying drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following detailed description, they are used to explain the present application but do not constitute a limitation of the present application. In the accompanying drawings:

[0022] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0023] Figure 2 It is a schematic structural diagram of an electronic device according to one embodiment of the present application.

[0024] Description of Reference Numerals

[0025] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, hole adjustment layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 400, electronic device. DETAILED DESCRIPTION

[0026] The following describes the specific embodiments of the present application in detail with reference to the accompanying drawings. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present application and are not intended to limit the present application.

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

[0028]

[0029] Wherein, A has the structure shown in Formula 2;

[0030] Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0031] L, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0032] X is O or S;

[0033] Each of R1, R2 and R3 is the same or different and is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a deuterated aryl group having 6 to 20 carbon atoms;

[0034] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n1 is greater than 1, any two R1 are the same or different;

[0035] n2 represents the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different;

[0036] n3 represents the number of R3, n3 is selected from 0, 1, 2, 3 or 4, when n3 is greater than 1, any two R3 are the same or different;

[0037] The substituents in Ar1, Ar2, L, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms or a deuterated alkyl group having 1 to 10 carbon atoms.

[0038] In this application, the number of carbon atoms in Ar1, Ar2, L, L1, and L2 refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene group having 10 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 10. For example, if Ar1 is 9,9-dimethylfluorenyl, then Ar1 is a substituted fluorenyl group having 15 carbon atoms, and Ar1 has 13 ring carbon atoms.

[0039] In this application, the expressions "substituted or unsubstituted aryl having 6-30 carbon atoms" and "substituted or unsubstituted aryl having 6-30 carbon atoms" have the same meaning, both referring to an aryl group and its substituents having a total carbon number of 6-30. Similarly, in this specification, the expressions "substituted or unsubstituted heteroaryl having 3-30 carbon atoms" and "substituted or unsubstituted heteroaryl having 3-30 carbon atoms" have the same meaning, both referring to a heteroaryl group and its substituents having a total carbon number of 3-30.

[0040] The description methods used in this application, "each...is independently" and "...are independently" and "...are independently selected from" can be interchanged and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or that in the same group, the specific options expressed by the same symbols do not affect each other.

[0041] For example: In " Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from the description of hydrogen, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.

[0042] In the present application, when no specific definition is provided otherwise, "hetero" means that a functional group includes at least one heteroatom such as B, N, O, S, Se, Si or P and the remaining atoms are carbon and hydrogen.

[0043] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent. For example, "substituted or unsubstituted aryl" refers to an aryl group with a substituent or an unsubstituted aryl group. "Substituted" means that the group may be substituted by a substituent selected from the following groups: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, and a deuterated alkyl group having 1 to 10 carbon atoms.

[0044] In the present application, "alkyl" can include straight-chain alkyl or branched-chain alkyl. Alkyl can have 1 to 10 carbon atoms. In the present application, numerical ranges such as "1 to 10" refer to individual integers in a given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. The alkyl group can be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc. In addition, the alkyl group can be substituted or unsubstituted.

[0045] As used herein, a cycloalkyl group refers to a cyclic saturated hydrocarbon, including monocyclic and polycyclic structures. A cycloalkyl group may have 3 to 10 carbon atoms. For example, "3 to 10 carbon atoms" refers to a cycloalkyl group containing 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0046] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon conjugation, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon conjugation, or two or more condensed ring aryl groups connected by carbon-carbon conjugation. That is, two or more aromatic groups connected by carbon-carbon conjugation can also be regarded as aryl groups in the present application. Among them, the aryl group does not contain heteroatoms such as B, N, O, S, Se, Si or P. For example, in the present application, phenyl, biphenyl, terphenyl, etc. are aryl groups. Examples of aryl groups can include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaternaryl, benzo[9,10]phenanthrenyl, pyrenyl, perylenyl, benzofluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, indenyl and the like, but are not limited thereto.

[0047] The "substituted or unsubstituted aryl group" herein may contain 6-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-24. In other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-20, but is not limited thereto. In the present application, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30.

[0048] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, I, CN, a hydroxyl group, a branched alkyl group, a straight-chain alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl group, a deuterated aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, or other groups. It is understood that the number of carbon atoms in 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 means that the total number of carbon atoms in the aryl group and the substituents on the aryl group is 18. For example, 9,9-dimethylfluorenyl is a substituted aryl group with 15 carbon atoms. In this application, specific examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl.

[0049] In the present application, the fluorenyl group as an aromatic group may be substituted, and two substituents may be combined with each other to form a spiro structure. Specific examples include but are not limited to the following structures:

[0050]

[0051] In the present application, the heteroaryl group may be a heteroaryl group including 1, 2, 3, 4, 5 or 6 heteroatoms selected from B, O, N, P, Si, Se and S. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugation of carbon-carbon bonds, any of which is an aromatic monocyclic ring or an aromatic fused ring, and any of which contains the heteroatoms. For example, the heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzothiophenyl, dibenzofuranyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, etc., without limitation thereto.

[0052] The "substituted or unsubstituted heteroaryl group" herein may contain 3-30 carbon atoms. In some embodiments, the substituted or unsubstituted heteroaryl group is a heteroaryl group having 12-24 carbon atoms. In other embodiments, the substituted or unsubstituted heteroaryl group is a heteroaryl group having 12-20 carbon atoms, but is not limited thereto. In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30.

[0053] In this application, a substituted heteroaryl group refers to a heteroaryl group in which one or more hydrogen atoms are replaced by other groups, for example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, CN, an alkyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a deuterated aryl group, a heteroaryl group, an aryloxy group, an arylthio group, a silanyl group, a phosphinoyl group, or other groups. In this application, specific examples of heteroaryl groups as substituents include, but are not limited to, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.

[0054] In the present application, the explanations for aryl group may be applied to arylene group, the explanations for heteroaryl group may be applied to heteroarylene group, the explanations for alkyl group may be applied to alkylene group, and the explanations for cycloalkyl group may be applied to cycloalkylene group.

[0055] The non-positioned connecting bond in this application refers to a single bond extending from the ring system 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.

[0056] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).

[0057]

[0058] For another example, as shown in the following formula (X'), the phenanthryl group represented by formula (X') is connected to other positions in the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formulas (X'-1) to (X'-4).

[0059]

[0060] A non-positional substituent in this 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 attached at 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 by a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7).

[0061]

[0062] The meanings of non-positional connection or non-positional substitution in the following text are the same as those herein and will not be further described.

[0063] In the present application, the carbon number of the haloalkyl group having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, including but not limited to trifluoromethyl and the like.

[0064] In the present application, the deuterated alkyl group having 1 to 10 carbon atoms may have 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, for example.

[0065] In the present application, the deuterated aryl group having 6 to 20 carbon atoms may have 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, for example.

[0066] In the present application, the halogen group may be selected from fluorine, chlorine, bromine or iodine.

[0067] In some embodiments of the present application, the nitrogen-containing compound has a structure shown in Formula 1-1 or Formula 1-2:

[0068]

[0069] In some specific embodiments of the present application, the nitrogen-containing compound has a structure shown in Formula 2-1, Formula 2-2, Formula 2-3 or Formula 2-4:

[0070]

[0071]

[0072] In some specific embodiments of the present application, each R1 and R2 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0073] In some embodiments of the present application, each R3 is independently selected from deuterium or an aryl group having 6 to 12 carbon atoms.

[0074] In other embodiments of the present application, each R3 is independently selected from deuterium, phenyl, naphthyl or biphenyl.

[0075] Preferably, R3 is selected from phenyl.

[0076] In some embodiments of the present application, each R3 is independently selected from the group consisting of deuterium or the following groups:

[0077]

[0078] Specifically, each R3 is independently selected from the group consisting of deuterium or the following groups:

[0079]

[0080] In some specific embodiments of the present application, n1 and n2 are both 0.

[0081] In some specific embodiments of the present application, n3 is selected from 0 or 1.

[0082] In some specific embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0083] Optionally, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0084] Optionally, the substituents in Ar1 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0085] In some specific embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl.

[0086] Optionally, the substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0087] In some specific embodiments of the present application, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted group V1, and the unsubstituted group V1 is selected from the group consisting of the following groups:

[0088]

[0089]

[0090] in, represents a chemical bond; the substituted group V1 contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl; when the substituted group V1 contains multiple substituents, the substituents are the same or different.

[0091] Optionally, Ar1 and Ar2 are the same or different and are independently selected from the group consisting of the following groups:

[0092]

[0093] In some specific embodiments of the present application, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6-18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12-18 carbon atoms.

[0094] Optionally, L1 and L2 are the same or different and are 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 12 to 18 carbon atoms.

[0095] Optionally, the substituents in L1 and L2 are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0096] In some specific embodiments of the present application, L1 and L2 are the same or different and are 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 carbazolyl group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzofuranyl group.

[0097] Optionally, the substituents in L1 and L2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0098] In some specific embodiments of the present application, L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted group V2, and the unsubstituted group V2 is selected from the group consisting of the following groups:

[0099]

[0100] in, represents a chemical bond; the substituted group V2 contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; when the substituted group V2 contains multiple substituents, the substituents are the same or different.

[0101] Optionally, L1 and L2 are the same or different and are independently selected from a single bond or the group consisting of the following groups:

[0102]

[0103] In some specific embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0104] Optionally, the substituents in L are the same or different and are independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0105] In other specific embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

[0106] Optionally, the substituents in L are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0107] Preferably, L is a single bond or a phenylene group.

[0108] Specifically, L is selected from the group consisting of a single bond or the following groups:

[0109]

[0110] In some specific embodiments of this application, are independently selected from the group consisting of:

[0111]

[0112]

[0113] Optionally, are independently selected from the group consisting of:

[0114]

[0115] In some specific embodiments of the present application, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] In a second aspect, the present application provides 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; the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.

[0125] For example, if Figure 1 As shown, the organic electroluminescent device may include an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 contains the nitrogen-containing compound described in the first aspect of the present application.

[0126] In a specific embodiment of the present application, the organic electroluminescent device is, for example, a green organic electroluminescent device.

[0127] In some specific embodiments of the present application, the functional layer 300 includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound.

[0128] In some specific embodiments of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole adjustment layer 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 stacked in sequence.

[0129] In some specific embodiments of the present application, the anode 100 includes the following anode materials, preferably materials with a large work function that facilitates hole injection into the functional layer. Anode materials specifically include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0130] In some specific embodiments of the present application, the hole transport layer 321 and the hole adjustment layer 322 may include one or more hole transport materials. The hole transport layer materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. Specifically, the hole transport layer 321 is composed of the compound PAPB.

[0131] In some specific embodiments of the present application, the hole adjustment layer 322 may be composed of the compound NPBAPF.

[0132] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example:

[0133]

[0134] In some embodiments of the present application, the hole injection layer 310 is composed of F4-TCNQ and PAPB.

[0135] In the present application, 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, wherein the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application does not impose any particular limitation on this. For example, in one embodiment of the present application, the electron transport layer 340 may be composed of ET-01 and LiQ.

[0136] In some specific embodiments of the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material or may be composed of a host material and a guest material. Preferably, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0137] The main material of the organic light-emitting layer 330 can be the nitrogen-containing compound of the present application, or it can be composed of the nitrogen-containing compound of the present application and other light-emitting main materials, such as metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. This application does not impose any specific restrictions on this. In one specific embodiment, the main material of the organic light-emitting layer 330 is composed of the nitrogen-containing compound of the present application and compound GH-n.

[0138] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not impose any particular restrictions on this. In one specific embodiment of this application, the guest material of the organic light-emitting layer 330 is compound GD-01.

[0139] In some embodiments of the present application, the host material of the organic light-emitting layer 330 is the organic compound of the present application and GH-n, and the guest material is GD-01.

[0140] In some embodiments of the present application, cathode 200 includes a cathode material having a low work function that facilitates electron injection into the functional layer. 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 materials such as, but not limited to, LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode containing silver and magnesium is used as the cathode.

[0141] In this application, if Figure 1 As shown, a hole injection layer 310 may be 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitations thereon. In one embodiment of this application, the hole injection layer 310 may be composed of the compound NPBAPF.

[0142] In some specific embodiments of this application, Figure 1 As shown, an electron injection layer 350 may be 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. Specifically, the electron injection layer 350 may include Yb.

[0143] The third aspect of the present application provides an electronic device, which includes the organic electroluminescent device provided in the second aspect of the present application. Since the electronic device includes any of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, it has the same beneficial effects, and this application will not repeat them here.

[0144] For example, if Figure 2 As shown, one embodiment of the present application provides an electronic device 400. The electronic device 400 includes the organic electroluminescent device described in the above embodiments. Any organic electroluminescent device described in the embodiments can be used. The electronic device 400 can be a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.

[0145] The present application is further described below by way of examples, but the present application is not limited thereto.

[0146] The present application does not particularly limit the synthesis method of the nitrogen-containing compounds provided. Those skilled in the art can determine a suitable synthesis method based on the nitrogen-containing compounds of this application in combination with the preparation methods provided in the preparation examples. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not interpret this as a limitation of this application.

[0147] Preparation of compounds

[0148] Synthesis of intermediate SM-1-1

[0149]

[0150] SM-1 (30.0 g, 125.5 mmol), p-bromoiodobenzene (35.5 g, 125.5 mmol), anhydrous potassium carbonate (26.0 g, 188.2 mmol), and TBAB (2.02 g, 6.3 mmol) were added to a mixed solution of toluene (240 mL), ethanol (120 mL), and water (60 mL). The temperature was slowly raised to 50°C, and tetrakis(triphenylphosphine)palladium (7.25 g, 6.27 mmol) was added. The temperature was raised to reflux, and the reaction was complete after 16 hours. The reaction solution was cooled to room temperature and washed with water until neutral. Magnesium sulfate was then added for drying, and the filtrate was filtered and the solvent was removed by decompression. The crude product was recrystallized using a toluene / n-heptane system to obtain SM-1-1 (33.3 g, yield 76%).

[0151] Synthesis of intermediate SM-X-1

[0152] The other intermediates SM-X-1 listed in Table 1 were synthesized by referring to the method of intermediate SM-1-1, except that SM-1 was replaced by SM-X. The raw material structures, product structures and yields are shown in Table 1.

[0153] Table 1

[0154]

[0155]

[0156] Synthesis of intermediate SM-A-7

[0157]

[0158] SM-1-1 (30.0 g, 85.9 mmol) was added to a solution of tetrahydrofuran (300 mL), cooled to -78°C, and n-butyl lithium (5.50 g, 85.9 mmol) was added dropwise. After keeping warm for 30 minutes, trimethyl borate (13.4 g, 128.9 mmol) was added dropwise. After keeping warm for 1 hour, the temperature was raised to room temperature. After stirring overnight, dilute hydrochloric acid was added to neutralize the reaction solution. The reaction solution was then washed with water until neutral, and then magnesium sulfate was added to dry it. After filtering, the filtrate was decompressed to remove the solvent; the crude product was recrystallized using an n-heptane system to obtain SM-A-7 (16.2 g, yield 60%).

[0159] Synthesis of intermediate SM-AY

[0160] The other intermediates SM-AY listed in Table 2 were synthesized by referring to the method of intermediate SM-A-7, except that SM-1-1 was replaced by SM-X-1. The raw material structures, product structures and yields are shown in Table 2.

[0161] Table 2

[0162]

[0163] Synthesis of intermediate A1-1

[0164]

[0165] The raw material SM-A-1 (15.0 g, 62.7 mmol), the raw material SM-B-1 (12.0 g, 62.7 mmol), anhydrous potassium carbonate (13 g, 94.1 mmol), and TBAB (1.0 g, 3.14 mmol) were added to a mixed solution of toluene (90 mL), ethanol (60 mL) and water (30 mL), and the temperature was slowly raised to 50°C. Tetrakis(triphenylphosphine)palladium (3.6 g, 3.1 mmol) was added and the temperature was raised to reflux. The reaction was completed after 16 hours. The reaction solution was cooled to room temperature and washed with water until neutral. Magnesium sulfate was then added for drying. After filtration, the filtrate was decompressed to remove the solvent; the crude product was recrystallized using a toluene / n-heptane system to obtain intermediate A1-1 (15.4 g, yield 70%).

[0166] Synthesis of intermediates A1-Z

[0167] The other intermediates A1-Z listed in Table 3 were synthesized by referring to the method of intermediate A1-1, except that SM-A-1 was replaced by SM-AY. The raw material structures, product structures and yields are shown in Table 3.

[0168] Table 3

[0169]

[0170]

[0171] Synthesis of intermediate A2-1:

[0172]

[0173] Intermediate A1-1 (15 g, 42.7 mmol), triphenylphosphine (33.6 g, 128.3 mmol), and o-dichlorobenzene (150 mL) were added to a three-necked flask, heated to 150° C. under nitrogen protection, and heated under reflux with stirring for 18 h. After the reaction was completed, the distillation apparatus was changed to 160° C. and distillation was continued until o-dichlorobenzene was completely evaporated to obtain a solid crude product, which was purified by silica gel column chromatography (dichloromethane / n-heptane) to obtain A2-1 (6.1 g, yield 45%).

[0174] Synthesis of intermediate A2-M

[0175] Other intermediates A2-M listed in Table 4 were synthesized by referring to the method of intermediate A2-1, except that A1-1 was replaced by raw material A. The raw material structures, product structures and yields are shown in Table 4.

[0176] Table 4

[0177]

[0178]

[0179] Synthesis of intermediate A3-1

[0180]

[0181] A2-1 (10 g, 31.4 mmol), SM-C-1 (7.0 g, 34.5 mmol), potassium carbonate (9.53 g, 69.0 mmol), cuprous iodide (1.2 g, 6.3 mmol), 18-crown ether-6 (0.8 g, 3.1 mmol), 1,10-phenanthroline (2.3 g, 12.5 mmol), and N,N-dimethylformamide (100 mL) were reacted for 24 h. The reaction was completed and the temperature was cooled to room temperature. 500 mL of water was added, and a large amount of solid precipitated. The solid was filtered and the filter cake was completely dissolved with 300 mL of dichloromethane and washed with water until neutral. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane / n-heptane) to obtain intermediate A3-1 (8.7 g, yield 70%).

[0182] Synthesis of intermediate A3-N

[0183] The other intermediates A3-N listed in Table 5 were synthesized by referring to the method of intermediate A3-1, except that A2-1 was replaced by raw material B, and SM-C-1 was replaced by raw material C. The raw material structures, product structures and yields are shown in Table 5.

[0184] Table 5

[0185]

[0186]

[0187]

[0188]

[0189] Synthesis of intermediate B1-1

[0190]

[0191] SM-E-1 (10.0 g, 28.0 mmol), raw material SM-F-1 (6.7 g, 28.0 mmol), anhydrous potassium carbonate (5.8 g, 42.0 mmol), and TBAB (0.4 g, 1.4 mmol) were added to a mixed solution of toluene (80 mL), ethanol (40 mL), and water (20 mL). The temperature was slowly raised to 50°C, and tetrakis(triphenylphosphine)palladium (1.62 g, 1.4 mmol) was added. The temperature was raised to reflux, and the reaction was complete after 16 h. The reaction solution was cooled to room temperature and washed with water until neutral. Magnesium sulfate was then added for drying. After filtration, the filtrate was decompressed to remove the solvent; the crude product was recrystallized using a toluene / n-heptane system to obtain intermediate B1-1 (9.9, yield 75%).

[0192] Synthesis of compound 29

[0193]

[0194] Raw material A3-1 (10.0 g, 25.3 mmol), raw material SM-D-1 (9.2 g, 25.3 mmol), anhydrous potassium carbonate (5.3 g, 37.9 mmol), and TBAB (0.4 g, 1.3 mmol) were added to a mixed solution of toluene (80 mL), ethanol (40 mL), and water (20 mL), and the temperature was slowly raised to 50°C. Tetrakis(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added and the temperature was raised to reflux. The reaction was complete after 16 h. The reaction solution was cooled to room temperature and washed with water until neutral. Magnesium sulfate was then added for drying. After filtration, the filtrate was decompressed to remove the solvent. The crude product was recrystallized using a toluene / n-heptane system to obtain compound 29 (9.6 g, yield 56%).

[0195] Synthesis of compound Y

[0196] The other compounds Y listed in Table 6 were synthesized by referring to the method of A3-1, except that A3-1 was replaced by raw material E and SM-D-1 was replaced by raw material F. The raw material structures, product structures and yields are shown in Table 6.

[0197] Table 6

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] The mass spectrometry data of the compounds are listed in Table 7.

[0206] Table 7

[0207] Compound <![CDATA[Mass spectrometry ([M+H] + )]]> Compound <![CDATA[Mass spectrometry ([M+H] + )]]> 29 678.3 30 754.3 31 754.3 32 754.3 21 602.3 27 618.2 36 694.3 49 678.3 50 754.3 51 754.3 52 754.3 72 754.3 101 754.3 103 830.3 113 678.3 118 830.3 135 830.3 141 768.3 149 678.3 167 830.3 177 834.3 44 754.3 67 678.3 61 694.3 175 844.3 182 830.3

[0208] The NMR data of some compounds are listed in Table 8.

[0209] Table 8

[0210]

[0211] Example 1 Green organic electroluminescent device

[0212] Anode preparation: ITO / Ag / ITO with a thickness of The ITO substrate was cut into a size of 40 mm × 40 mm × 0.7 mm. A photolithography process was used to obtain an experimental substrate with cathode, anode and insulating layer patterns. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode and remove scum.

[0213] On the experimental substrate, F4-TCNQ:PAPB was co-evaporated at a weight ratio of 2%:98% to form a film with a thickness of The hole injection layer is formed by evaporating PAPB on the hole injection layer. hole transport layer.

[0214] NPBAPF was vacuum-deposited on the hole transport layer to form Hole Adjustment Layer.

[0215] On the hole adjustment layer, compound 29:GH-n:GD-01 was co-deposited at a film thickness ratio of 44%:44%:12% to form a film with a thickness of organic light-emitting layer (G-EML).

[0216] ET-01 and LiQ were evaporated at a rate ratio of 1:1 to form The electron transport layer is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of The electron injection layer is then vacuum-deposited with magnesium and silver at a film thickness ratio of 1:9. On the electron injection layer, a cathode is formed.

[0217] In addition, CP-01 was deposited on the cathode to form An organic covering layer is formed, thereby completing the manufacture of a green organic light-emitting device.

[0218] Example 2-26

[0219] A green organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in the following Table 9 was used instead of Compound 29.

[0220] Comparative Example 1

[0221] A green organic electroluminescent device was prepared by the same method as in Example 1, except that Compound a was used instead of Compound 29.

[0222] Comparative Example 2

[0223] A green organic electroluminescent device was prepared by the same method as in Example 1, except that Compound b was used instead of Compound 29.

[0224] Comparative Example 3

[0225] A green organic electroluminescent device was prepared by the same method as in Example 1, except that Compound C was used instead of Compound 29.

[0226] The material structures used in the above embodiments and comparative examples are as follows:

[0227]

[0228] For the organic electroluminescent device prepared as above, at 20 mA / cm 2 The performance of the device was analyzed under the conditions of , and the results are shown in Table 9 below:

[0229] Table 9

[0230]

[0231] According to the results in Table 9, compared with Comparative Examples 1-3, the organic electroluminescent devices prepared using the nitrogen-containing compounds as the main materials of the organic light-emitting layers in Examples 1-26 have a current efficiency improved by at least 11.7%, a power efficiency improved by at least 18.3%, and a lifespan improved by at least 12.4%.

[0232] The present application provides a nitrogen-containing compound, which is a class of compounds with a core structure composed of a combination of 3,3-dicarbazole and benzoxazole / benzothiazole groups. Among them, 3,3-dicarbazole has good hole transport properties. When it is combined with benzoxazole / benzothiazole, which has electronic properties, the material can have relatively balanced carrier transport properties. Connecting benzoxazole / benzothiazole to one of the carbazole rings in 3,3-dicarbazole can give the material a suitable T1 energy level, thereby enhancing the exciton energy transfer effect. When it is used as a light-emitting layer material in an organic electroluminescent device, the device performance can be significantly improved. In particular, when 3,3-dicarbazole and benzoxazole are connected, the device performance is even better.

[0233] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection of the present application.

Claims

1. A nitrogen-containing compound, characterized in that The nitrogen-containing compound has a structure shown in the following formula 1: Formula 1 Formula 2 Wherein, A has the structure shown in Formula 2; Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl; The substituents in Ar1 and Ar2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and naphthyl; L1 and L2 are the same or different and are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; The substituents in L1 and L2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or naphthyl; L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; The substituents in L are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; X is O or S; each R1 and R2 are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; each R3 is independently selected from deuterium, phenyl, naphthyl or biphenyl; n1 represents the number of R1, n1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n1 is greater than 1, any two R1 are the same or different; n2 represents the number of R2, n2 is selected from 0, 1, 2 or 3, when n2 is greater than 1, any two R2 are the same or different; n3 represents the number of R3, and n3 is selected from 0, 1, 2, 3 or 4. When n3 is greater than 1, any two R3 are the same or different.

2. The nitrogen-containing compound according to claim 1, characterized in that The nitrogen-containing compound has a structure shown in Formula 1-1 or Formula 1-2:

3. The nitrogen-containing compound according to claim 1, characterized in that and are independently selected from the group consisting of: 。 4. A nitrogen-containing compound, characterized in that The nitrogen-containing compound is selected from the group consisting of the following compounds: 。 5. An organic electroluminescent device, characterized in that The invention comprises 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 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 contains the nitrogen-containing compound.

7. The organic electroluminescent device according to claim 5, characterized in that: The organic electroluminescent device is a green organic electroluminescent device.

8. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to any one of claims 5 to 7.

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