Nitrogen-containing compounds and organic electroluminescent devices and electronic devices

Abstract

This application relates to the technical field of organic electroluminescent materials and provides a nitrogen-containing compound, an organic electroluminescent device, and an electronic device containing the same. The nitrogen-containing compound of the present application comprises a parent core structure of a naphthofuroxazole / thiazole group. When used as the host material of the light-emitting layer of an organic electroluminescent device, the nitrogen-containing compound can significantly improve the luminous efficiency and service life of the device.

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 anode and the cathode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward 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 with existing organic electroluminescent devices are lifespan and efficiency. As displays become 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 represented by Formula 1:

[0006]

[0007] wherein Y is selected from S or O;

[0008] One of X and Z is —N=, and the other is O or S;

[0009] Z1, Z2 and Z3 are selected from C(R1) or N, and at least two of Z1, Z2 and Z3 are N;

[0010] Ring A is selected from a naphthalene ring or a phenanthrene ring;

[0011] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0012] Ar1, Ar2 and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0013] The substituents in L, L1, L2, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0014] Each R1 and R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; any two adjacent R1 or R1 groups form a ring; and n is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[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 nitrogen-containing compound described above.

[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 present application's compound structure contains naphthalene (phenanthrene) and furan and oxazole / thiazole-triazine / pyrimidine electron-deficient heteroaryl, wherein naphthalene (phenanthrene) and furan and oxazole / thiazole groups all have electron transport properties, and the two are fused to increase the conjugated system so that the electron transport performance of the group is enhanced; triazine or pyrimidine groups have excellent electron transport properties; naphthalene (phenanthrene) and furan and oxazole / thiazole and triazine, pyrimidine electron-deficient heteroaryl are connected to give the present application's compound excellent electron transport properties. The present application's compound and hole transport material are mixed to form a hybrid host material, which can improve the carrier balance in the light-emitting layer, widen the carrier recombination region, improve exciton generation and utilization efficiency, and improve 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 structural diagram of an organic electroluminescent device according to one embodiment of the present application.

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

[0021] Reference numerals

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

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

[0024] 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0025] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete and will fully convey the concepts of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to 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 Formula 1:

[0027]

[0028] wherein Y is selected from S or O;

[0029] One of X and Z is —N=, and the other is O or S;

[0030] Z1, Z2 and Z3 are selected from C(R1) or N, and at least two of Z1, Z2 and Z3 are N;

[0031] Ring A is selected from a naphthalene ring or a phenanthrene ring;

[0032] 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0033] Ar1, Ar2 and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0034] The substituents in L, L1, L2, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0035] Each R1 and R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; any two adjacent R1 or R1 groups form a ring; and n is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0036] In this 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, "optionally, any two adjacent substituents among Ar1, Ar2 and Ar3 form a ring" means that any two adjacent substituents among Ar1, Ar2 and Ar3 are connected to each other to form a ring, or any two adjacent substituents among Ar1, Ar2 and Ar3 can also exist independently of each other. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocycle with the atom to which they are commonly connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0037] In this application, the descriptions “each independently is”, “each independently is” and “each independently is” are interchangeable 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 in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents 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 represents 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.

[0038] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease 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 substituent 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 cycloalkyl group, etc. The number of substitutions can be one or more.

[0039] In this application, "plurality" refers to more than two, for example, 2, 3, 4, 5, 6, etc.

[0040] 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).

[0041] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0042] 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 (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon bond conjugation can also be considered as aryl of the present application. Wherein, condensed ring aryl, for example, can include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as 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, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0043] 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.

[0044] In this application, terphenyl includes and

[0045] In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of 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 being 18.

[0046] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38 or 40, etc. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0047] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0048] In the present application, the aryl group as a substituent of L, L1, L2, Ar1, Ar2 and Ar3 includes, but is not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0049] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For 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 triazinyl 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 silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0050] 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.

[0051] 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 having a total carbon number of 3 to 40, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 30, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 5 to 12.

[0052] In the present application, the heteroaryl groups as substituents of L, L1, L2, Ar1, Ar2 and Ar3 are exemplified by, but not limited to, pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl and dibenzofuranyl.

[0053] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, 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.

[0054] 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 in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. 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, and n-hexyl.

[0055] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0056] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0057] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0058] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 carbon atoms may be, 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.

[0059] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link 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 via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0060]

[0061]

[0062] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0063]

[0064] A non-positional substituent herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within 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 via a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7):

[0065]

[0066] In some embodiments, the compound represented by Formula 1 is selected from the following structures represented by Formulas (1-1) to (1-16):

[0067]

[0068]

[0069] In some embodiments, the compound represented by Formula 1 is selected from the following structures represented by Formulas (2-1) to (2-11):

[0070]

[0071] In some embodiments, Z1 and Z3 are N, and Z2 is selected from C(H) or N; or Z1 and Z2 are N, and Z3 is selected from C(H) or N; or Z1, Z2 and Z3 are all N.

[0072] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups 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 groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms.

[0073] In some embodiments, Ar1, Ar2, and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms.

[0074] In some embodiments, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0075] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl.

[0076] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and optionally, in Ar1 and Ar2, any two adjacent substituents form a benzene ring or a fluorene ring.

[0077] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from a substituted or unsubstituted group W; wherein the unsubstituted group W is selected from the group consisting of:

[0078]

[0079] The substituted group W has one or more substituents, and the substituents of the substituted group W are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

[0080] In some embodiments, Ar1 and Ar2 are independently selected from the group consisting of:

[0081]

[0082]

[0083] In some embodiments, Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; the substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl or deuterated phenyl.

[0084] In some embodiments, Ar3 is selected from the group consisting of:

[0085]

[0086] In some embodiments, 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 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0087] 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.

[0088] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 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.

[0089] In some embodiments, L is 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 pyridylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzofuranylene group.

[0090] In some embodiments, L1 and L2 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 fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted benzoxazolylene group, or a substituted or unsubstituted benzothiazolylene group.

[0091] 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, trideuterated methyl, trimethylsilyl or phenyl.

[0092] Alternatively, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the following groups:

[0093]

[0094] The substituted group Q has one or more substituents, and the substituents of the substituted group Q are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, 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 Q is greater than 1, the substituents are the same or different.

[0095] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0096]

[0097] In some embodiments, L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0098]

[0099] Optionally, each R is the same or different and is independently selected from hydrogen, deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0100] Alternatively, each R1 is hydrogen, deuterium or cyano.

[0101] Optionally, the nitrogen-containing compound is selected from the group consisting of the following compounds:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] 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.

[0119] 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, lifespan and other characteristics of the organic electroluminescent device.

[0120] 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 this application, or can be composed of the nitrogen-containing compound provided in this application and other materials.

[0121] 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 first hole transport layer 321, a second hole transport 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.

[0122] 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 are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0123] In the present application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may specifically be selected from the following compounds or any combination thereof:

[0124]

[0125] In one embodiment, the first hole transport layer 321 may be composed of α-NPD.

[0126] In one embodiment, the second hole transport layer 322 is composed of HT-1.

[0127] Optionally, a hole injection layer 310 is provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first 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 limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof:

[0128]

[0129] In one embodiment, the hole injection layer 310 is composed of PD.

[0130] 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. 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.

[0131] 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.

[0132] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or its derivative, a compound having a heteroaromatic ring or its derivative, an aromatic amine derivative or other materials, and this application does not impose any special restrictions on this. The guest material is also called a doping material or dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. Specific examples of the phosphorescent dopant include, but are not limited to,

[0133]

[0134] In one embodiment of the present application, the organic electroluminescent device is a red 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, RD-1.

[0135] 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 may be, for example, fac-Ir(ppy)3.

[0136] 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. The electron transport materials may be selected from, but not limited to, BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and are not specifically limited in this application. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0137]

[0138]

[0139] In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ, or composed of ET-2 and LiQ.

[0140] In the present application, cathode 200 may include a cathode material having 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 alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode containing magnesium and silver may be included as the cathode.

[0141] 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 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. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).

[0142] 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.

[0143] According to one embodiment, Figure 2 As shown, the provided electronic device is electronic device 400, which includes the above-mentioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0144] The synthesis method of the nitrogen-containing compound of the present application is described in detail below with reference to synthesis examples, but the present disclosure is not limited thereby.

[0145] Synthesis Example

[0146] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds described herein, and that other methods for preparing the compounds described herein are considered within the scope of this application. For example, the synthesis of compounds not exemplified herein can be successfully accomplished by one skilled in the art through modifications such as appropriate protection of interfering groups, the use of known reagents other than those described herein, or conventional modifications of reaction conditions. Compounds for which the syntheses are not described herein are obtained from commercially available raw materials.

[0147] Synthesis of 7-bromo-1-iodo-2-naphthol:

[0148]

[0149] Under nitrogen, 7-bromo-1-iodo-2-naphthylamine (CAS: 2411719-24-7, 17.40 g, 50 mmol), concentrated hydrochloric acid (25 mL), and deionized water (25 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was cooled to 0°C in an ice-water bath. A solution of sodium nitrite (3.45 g, 50 mmol) in water (25 mL) was added dropwise. After the addition was complete, a solution of potassium thiocyanate (9.72 g, 100 mmol) and ferric chloride (4.1 g, 25 mmol) in water (25 mL) were added dropwise. After the addition was complete, the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into deionized water (200 mL) and extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product, which was used directly in the next step without purification.

[0150] Under a nitrogen atmosphere, the crude product, sodium sulfide nonahydrate (9.61 g, 100 mmol), ethanol (180 mL), and deionized water (360 mL) were added to a 1000 mL three-necked flask in one portion. The mixture was heated to reflux and stirred for 16 h. After the reaction system cooled to room temperature, it was filtered, and the filtrate was acidified to pH 2 with 1 M dilute hydrochloric acid. The mixture was then extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 7-bromo-1-iodo-2-naphthol (8.03 g, 44% yield) as a white solid.

[0151] Synthesis of Sub-a1:

[0152]

[0153] Under nitrogen atmosphere, 7-bromo-2-phenylbenzoxazole (CAS: 1268137-13-8, 12.06 g, 44 mmol), diboronic acid pinacol ester (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol) and 1,4-dioxane (120 mL) were added to a 500 mL three-necked flask in sequence. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.40 g, 0.44 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.42 g, 0.88 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved in 200 mL of toluene, and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (10.17 g, 72% yield) was obtained.

[0154] Referring to the synthesis of Sub-a1, Sub-a2 and Sub-a4 were synthesized by using reactant A shown in Table 1 instead of 7-bromo-2-phenylbenzoxazole.

[0155] Table 1: Synthesis of Sub-a2 and Sub-a4

[0156]

[0157] Synthesis of Sub-b1:

[0158]

[0159] Under a nitrogen atmosphere, Sub-a1 (17.66 g, 55 mmol), 7-bromo-1-iodo-2-hydroxynaphthalene (17.45 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (150 mL × 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded Sub-b1 (11.03 g, 53% yield) as a white solid.

[0160] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b11 were synthesized by using reactant B shown in Table 2 instead of Sub-a1 and reactant C instead of 7-bromo-1-iodo-2-hydroxynaphthalene.

[0161] Table 2: Synthesis of Sub-b2 to Sub-b11

[0162]

[0163]

[0164] Synthesis of Sub-c1:

[0165]

[0166] Under nitrogen, a 500 mL three-necked flask was charged with Sub-b1 (20.81 g, 50 mmol), tert-butyl peroxybenzoate (BzOOt-Bu, 19.42 g, 100 mmol), palladium acetate (1.12 g, 5 mmol), 3-nitropyridine (0.62 g, 5 mmol), hexafluorobenzene (C6F6, 210 mL), and N,N'-dimethylimidazolidinone (DMI, 140 mL). Stirring and heating were initiated, and the temperature was raised to 90°C for 4 h. After cooling to room temperature, the mixture was extracted with ethyl acetate (100 mL x 3). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. Purification by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase afforded Sub-c1 (10.77 g, 52% yield) as a white solid.

[0167] Sub-c2 to Sub-c11 were synthesized by referring to Sub-c1 and using reactant D shown in Table 3 instead of Sub-b1.

[0168] Table 3: Synthesis of Sub-c2 to Sub-c11

[0169]

[0170]

[0171]

[0172] Synthesis of Sub-c12:

[0173]

[0174] Under a nitrogen atmosphere, Sub-c1 (10.36 g, 25 mmol) and 200 mL of deuterated benzene-D6 were added to a 100 mL three-necked flask. After heating to 60°C, trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added, and the temperature was continued to rise to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, stirred for 10 minutes, and then a saturated K3PO4 aqueous solution was added to neutralize the reaction solution. The organic layer was extracted with dichloromethane (50 mL × 3 times), the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Silica gel column chromatography using n-heptane / dichloromethane as the mobile phase gave Sub-c12 (6.82 g, 64% yield) as a white solid.

[0175] Synthesis of Sub-c13:

[0176]

[0177] Under a nitrogen atmosphere, Sub-b12 (10.80 g, 25 mmol), palladium dichloride (0.22 g, 1.25 mmol), and DMSO (120 mL) were added to a 250 mL three-necked flask. The temperature was raised to 140°C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic layer was extracted with dichloromethane (50 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain the crude product. Silica gel column chromatography using n-heptane / dichloromethane as the mobile phase provided Sub-c13 (7.85 g, 73% yield) as a white solid.

[0178] Referring to Sub-c13, Sub-c14 was synthesized by using reactant E shown in Table 4 instead of Sub-b12.

[0179] Table 4: Synthesis of Sub-c14

[0180]

[0181] Synthesis of Sub-d1:

[0182]

[0183] Under nitrogen atmosphere, Sub-c1 (10.36 g, 25 mmol), diboronic acid pinacol ester (7.62 g, 30 mmol), potassium acetate (5.40 g, 55 mmol) and 1,4-dioxane (100 mL) were added in sequence to a 250 mL three-necked flask. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (0.23 g, 0.25 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (0.24 g, 0.5 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 100 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then rinsed with 50 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved with 100 mL of toluene, and passed through a silica gel column to remove the catalyst to obtain a white solid Sub-d1 (7.15 g, yield 62%).

[0184] Referring to the synthesis of Sub-d1, reactant F shown in Table 5 was used instead of Sub-c1 to synthesize Sub-d2 to Sub-d14.

[0185] Table 5: Synthesis of Sub-d2 to Sub-d14

[0186]

[0187]

[0188] Synthesis of compound 1:

[0189]

[0190] Under nitrogen, to a 250 mL three-necked flask were added Sub-d1 (11.53 g, 25 mmol), SM-1 (CAS: 1300115-09-6, 5.55 g, 20 mmol), palladium acetate (0.045 g, 0.2 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.19 g, 0.4 mmol), anhydrous potassium carbonate (5.53 g, 40 mmol), toluene (120 mL), tetrahydrofuran (30 mL), and deionized water (30 mL). Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After cooling the system to room temperature, extraction with dichloromethane (100 mL × 3 times) was performed. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. Purification was performed by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid compound 1 (8.99 g, yield 78%), m / z = 577.2 [M+H] + .

[0191] Referring to the synthesis of compound 1, reactant G shown in Table 6 was used instead of Sub-d1, and reactant H was used instead of SM-1 to synthesize the compounds of the present application in Table 6.

[0192] Table 6: Synthesis of the compounds of the present application

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] NMR data of some compounds:

[0201] NMR data of compound 6: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm9.41(s,1H),8.82(d,2H),8.65(d,1H),8.36- 8.33(m,3H),8.29-8.23(m,2H),8.11(d,1H),8.06(d,1H),7.77-7.48(m,12H),7.37(t,1H);

[0202] NMR data of compound 389: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 9.55(s,1H),8.82(d,2H),8.65(d,1H),8.38-8.34(m,3H),8.28(d,2H),8.08(d,1H),7.98( d,2H),7.88(d,1H),7.79-7.70(m,3H),7.67-7.51(m,8H),7.47(t,1H),7.42-7.33(m,3H).

[0203] Preparation and evaluation of organic electroluminescent devices:

[0204] Example 1: Preparation of red organic electroluminescent device

[0205] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed 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.

[0206] PD was vacuum-deposited on the experimental substrate (anode) to form a Then, α-NPD is vacuum-deposited on the hole injection layer to form a hole injection layer (HIL). The first hole transport layer.

[0207] Compound HT-1 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of a second hole transport layer.

[0208] Next, compound 1:RH-P:RD-1 was co-evaporated on the second hole transport layer at an evaporation rate ratio of 49%:49%:2% to form a layer with a thickness of A red organic light-emitting layer (EML) is provided.

[0209] On the organic light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 1:9 evaporation rate and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0210] In addition, CP-1 is vacuum-deposited on the cathode to form a layer with a thickness of The cover layer (CPL) is formed, thereby completing the manufacture of the red organic electroluminescent device.

[0211] Examples 2 to 40

[0212] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound X in Table 7 below was used instead of Compound 1 in Example 1 when preparing the organic light-emitting layer.

[0213] Comparative Examples 1 to 3

[0214] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A, Compound B, and Compound C were used to replace Compound 1 in Example 1 when preparing the organic light-emitting layer.

[0215] In each embodiment and comparative example, the structures of the main materials used are as follows:

[0216]

[0217] The performance of the red organic electroluminescent devices prepared in Examples 1 to 40 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 7.

[0218] Table 7

[0219]

[0220]

[0221] According to Table 7 above, when the compound of the present invention is used as the main material of a red organic electroluminescent device, the efficiency is increased by at least 12.3% and the lifespan is increased by at least 10.6%. The reason for this is that the structure of the compound of the present application contains a naphthofuran oxazole / thiazole-triazine / pyrimidine electron-deficient heteroaryl group, wherein both the naphthofuran and oxazole / thiazole groups have electron transport properties. After the two are fused, the conjugated system is enlarged, so that the electron transport performance of the group is enhanced; the triazine and pyrimidine groups have excellent electron transport properties; the naphthofuran oxazole / thiazole and triazine / pyrimidine electron-deficient heteroaryl groups are connected, giving the compound of the present application excellent electron transport properties. Mixing the compound of the present application with a hole transport material can form a hybrid main material, which 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 lifespan.

Claims

1. A nitrogen-containing compound, characterized in that The nitrogen-containing compound has a structure shown in Formula 1: wherein Y is selected from S or O; One of X and Z is —N=, and the other is O or S; Z1, Z2 and Z3 are selected from C(R1) or N, and at least two of Z1, Z2 and Z3 are N; Ring A is selected from a naphthalene ring; L is selected from a single bond; 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 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; Ar1 and Ar2 are the same or different and are each independently selected from 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; The substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl; The substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl; Each R1 and R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, or a phenyl group; n is selected from 1, 2, 3, 4, 5, 6 or 7.

2. The nitrogen-containing compound according to claim 1, wherein The nitrogen-containing compound is selected from the structures shown in the following formulas (1-1) to (1-12):

3. The nitrogen-containing compound according to claim 1, wherein Z1 and Z3 are N, and Z2 is selected from C(H) or N; or Z1 and Z2 are N, and Z3 is selected from C(H) or N; Alternatively, Z1, Z2, and Z3 are all N.

4. The nitrogen-containing compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms; The substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

5. The nitrogen-containing compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W; the unsubstituted group W is selected from the group consisting of: The substituted group W has one or more substituents, and the substituents of the substituted group W are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

6. The nitrogen-containing compound according to claim 1, wherein 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, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; The substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 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.

7. The nitrogen-containing compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the following groups: The substituted group Q has one or more substituents, and the substituents of the substituted group Q are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl, and when the number of substituents on the group Q is greater than 1, the substituents are the same or different.

8. The nitrogen-containing compound according to claim 1, wherein Ar1 and Ar2 are independently selected from the group consisting of: Ar3 is selected from the group consisting of:

9. The nitrogen-containing compound according to claim 1, wherein L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

10. The nitrogen-containing compound according to claim 1, wherein Each R is the same or different and is independently selected from hydrogen, deuterium, cyano, fluorine, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

11. Nitrogen-containing compounds, wherein The nitrogen-containing compound is selected from the group consisting of the following compounds:

12. 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 11.

13. The organic electroluminescent device according to claim 12, characterized in that: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the nitrogen-containing compound according to any one of claims 1 to 11.

14. An electronic device, characterized in that The organic electroluminescent device according to claim 12 or 13.

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