Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The nitrogen-containing heterocyclic compound has high electron mobility, and can effectively improve the efficiency of electron and hole combination; the nitrogen-containing heterocyclic compound is high in triplet state energy level and can effectively prevent migration of holes to an electron transport layer, so that the energy level barrier is reduced; the nitrogen-containing heterocyclic compound is used for functional layer materials such as an electron transport layer and a hole blocking layer of an organic electroluminescent device, so that the driving voltage can be reduced, the luminous efficiency can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a nitrogen-containing heterocyclic compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have attracted much attention due to their promising applications in flat panel displays and solid-state lighting. Compared with traditional display technologies, OLEDs have significant advantages such as self-emission, wide viewing angle, high brightness, high contrast, low power consumption, low driving voltage, flexible display capabilities, and fast response speed. The core of their success lies in the synergistic effect of various organic optoelectronic functional materials. Different functional layer materials each perform their specific functions, working together to ensure that OLED devices achieve efficient and stable light emission.

[0003] The optoelectronic functional materials constituting OLED devices consist of at least two or more layers. Industrially applied OLED device structures include multiple layers such as hole injection layers, hole transport layers, electron blocking layers, and emitting layers. In other words, the optoelectronic functional materials used in OLED devices include at least hole transport materials, emitting materials, and electron transport materials, exhibiting richness and diversity in material types and combinations. To fabricate high-performance OLED light-emitting devices, strict requirements are placed on the optoelectronic properties of various organic functional materials. For example, as electron transport materials, they need to possess good carrier mobility and high glass transition temperature; as hole blocking materials, they need to have high triplet energy levels to prevent exciton energy transfer to the electron transport layer, thus preventing energy loss; and as the main material of the emitting layer, they need to possess good bipolarity and appropriate HOMO / LUMO energy levels.

[0004] In addition, the CGL layer is particularly important in stacked OLED devices. By cascading multiple light-emitting units, the luminous efficiency and brightness of the device can be effectively improved, while the driving voltage is reduced and the lifespan of the device is extended.

[0005] The performance of OLED devices is highly dependent on the characteristics and synergistic effects of the materials in each functional layer. Each functional layer, as a key component of the OLED device structure, plays an indispensable role. However, there are still shortcomings in the optoelectronic functional materials and processes of OLED devices. To improve the luminous efficiency, lifetime, color purity, and other performance indicators of OLED devices, it is necessary to develop more efficient organic light-emitting materials to overcome these bottlenecks. Summary of the Invention

[0006] To address the aforementioned problems, this invention aims to develop a class of compounds for organic electroluminescent devices to improve electron mobility, prevent hole diffusion, enhance carrier recombination and luminescence efficiency, thereby improving device performance.

[0007] This invention provides a nitrogen-containing heterocyclic compound having the structure shown in Formula 1.

[0008] A is selected from formula 1-1.

[0009] The z that are the same or different are selected from CR1 or N, and the z that are bonded to L3 are selected from C atoms; The R1s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R1s forming a substituted or unsubstituted ring. The R is the same or different from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings; The n is selected from 0, 1, or 2; The Y values, whether identical or different, are selected from CR2 or N, and at least one Y is N, and is related to L. a L b The bonded Y atoms are selected from C atoms; The R2s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R2s forming a substituted or unsubstituted ring. The X that is the same as or different from is selected from CR3 or N, and is related to L. c L d The X atoms in the bond are selected from C atoms; The R3s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R3s forming a substituted or unsubstituted ring. The same or different Qs are selected from CR4 or N, and the Qs bonded to L1, L2, and L3 are selected from C atoms; The R4s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R4s forming a substituted or unsubstituted ring. The Ar a Ar b Ar c Ar d The same or different are selected from substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, substituted or unsubstituted cycloalkyl groups of C3-C12, or fused cycloalkanes of C3-C10 alicyclic and C6-C30 aromatic rings, respectively. The L a L b L c L d L1, L2, and L3 are the same or different from single bonds, substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C2-C30 heteroarylene groups, substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, and L1 and L2 are not simultaneously selected from single bonds.

[0010] Beneficial effects: The nitrogen-containing heterocyclic compound provided by this invention exhibits high electron mobility, which, when used as an electron transport layer material, can effectively improve the efficiency of electron-hole binding; its high triplet energy level, when used as a hole blocking layer material, can effectively prevent holes from migrating to the electron transport layer, thereby lowering the energy barrier. This compound can reduce the driving voltage of organic electroluminescent devices, improve luminous efficiency, and extend the device's lifespan. Detailed Implementation

[0011] The present invention will be further explained and illustrated below with reference to specific embodiments. It should be noted that these embodiments are merely examples to aid in understanding the present invention and are not intended to limit the scope of the invention. All other embodiments obtained by those skilled in the art based on the embodiments disclosed in this invention without inventive effort should be covered within the protection scope of this invention.

[0012] In this specification, " "This refers to the portion that is connected to another substituent."

[0013] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0014] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , And so on.

[0015] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0016] The "linked formation of substituted or unsubstituted rings" described in this invention refers to two groups linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0017] In this invention, the linked rings can be aromatic rings, aliphatic rings, or rings formed by the fusion of the two. The linked rings can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, or fused rings, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0018] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably having 1 to 9 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.

[0019] The cycloalkyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from a cyclic alkane molecule, preferably with 3 to 12 carbon atoms, more preferably with 3 to 10 carbon atoms, and particularly preferably with 3 to 7 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0020] The silyl group mentioned in this invention refers to -Si(R) f )3 groups, wherein each R f The same or different groups are selected from the following: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, or fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings. Preferably, each R f The same or different groups are selected from the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has C1-C20 carbon atoms, more preferably C1-C15, even more preferably C1-C10, and most preferably C1-C6. The cycloalkyl group preferably has C3-C20 carbon atoms, more preferably C3-C15, even more preferably C3-C10, and most preferably C3-C7. Preferably, each R...f The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the substituted silyl groups specifically include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0021] The aryl group described in this invention refers to a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0022] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 2 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0023] The arylene group referred to in this invention refers to the collective term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; specific examples may include naphthylene, anthraceneene, phenanthrene, pyreneene, terphenylene, fluoranthracene, etc., but are not limited to.

[0024] The heteroaryl group described in this invention refers to the general term for a divalent group in which at least one carbon atom is replaced by a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 2 to 30 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. Specific examples of monocyclic and fused-ring heteroaryl groups may include pyridylene, pyrimidinylene, triazineylene, furanylene, thiopheneylene, carbazoylene, benzofuranylene, benzothiopheneylene, benzocarbazoylene, dibenzofuranylene, dibenzothiopheneylene, dibenzocarbazoylene, etc., but are not limited thereto; specific examples of polycyclic heteroaryl groups may include bipyridylene, bipyrimidinylene, phenylpyridylene, etc., but are not limited thereto.

[0025] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by the fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Preferably, they have 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0026] The fused alicyclic and aromatic ring cycloalgides described in this invention refer to the collective term for the divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Preferably, they have 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused alicyclic and aromatic ring cycloalgides may include, but are not limited to, benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cycloheptane, and benzo[a]cycloheptenyl.

[0027] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted cycloalkyl, substituted silyl, substituted aryl, substituted heteroaryl, substituted alicyclic and aromatic fused ring group, substituted arylene, substituted heteroaryl," refers to a group that is independently monosubstituted or polysubstituted by the following groups: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, etc., but not limited to these, or adjacent substituents may be linked to form a ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl The group includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, etc.

[0028] The term "at least one" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.

[0029] This invention provides a nitrogen-containing heterocyclic compound having the structure described in Formula 1.

[0030] A is selected from formula 1-1.

[0031] The z that are the same or different are selected from CR1 or N, and the z that are bonded to L3 are selected from C atoms; The R1s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R1s forming a substituted or unsubstituted ring. The R is the same or different from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings; The n is selected from 0, 1, or 2; The Y values, whether identical or different, are selected from CR2 or N, and at least one Y is N, and is related to L. a L b The bonded Y atoms are selected from C atoms; The R2s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R2s forming a substituted or unsubstituted ring. The X that is the same as or different from is selected from CR3 or N, and is related to L. c L d The X atoms in the bond are selected from C atoms; The R3s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R3s forming a substituted or unsubstituted ring. The same or different Qs are selected from CR4 or N, and the Qs bonded to L1, L2, and L3 are selected from C atoms; The R4s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R4s forming a substituted or unsubstituted ring. The Ar a Ar b Ar c Ar dThe same or different are selected from substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, substituted or unsubstituted cycloalkyl groups of C3-C12, or fused cycloalkanes of C3-C10 alicyclic and C6-C30 aromatic rings, respectively. The L a L b L c L d L1, L2, and L3 are the same or different from single bonds, substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C2-C30 heteroarylene groups, substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, and L1 and L2 are not simultaneously selected from single bonds.

[0032] Preferably, Formula 1 is selected from any of the following structures.

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] The Q, A, Ar a Ar b Ar c Ar d L a L b L c L d L1, L2, L3, R2, and R3 have the same meaning as described above; s1 is selected from 0 or 1; s2 is selected from 0, 1 or 2; t1 is selected from 0 or 1; t2 is selected from 0, 1 or 2; t3 is selected from 0, 1, 2 or 3.

[0041] Preferably, Formula 1 is selected from any of the following structures.

[0042]

[0043]

[0044]

[0045] The Q, A, Ar a Ar b Ar c Ar d L a L b L c L d L1, L2, L3, R2, and R3 have the same meaning as described above; Preferably, the Selected from any one of the following groups, Indicates the connection site.

[0046]

[0047] R4 has the same meaning as described above.

[0048] Preferably, formula 1-1 is selected from any one of the following groups:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] R1 and R have the same meaning as described above; The n is selected from 0, 1, or 2; the m1 is selected from 0, 1, 2, 3, or 4; the m2 is selected from 0, 1, 2, 3, 4, 5, or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the m4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the m5 is selected from 0, 1, 2, or 3; the m6 is selected from 0, 1, or 2; the m7 is selected from 0 or 1; the m8 is selected from 0, 1, 2, 3, 4, or 5; and the m9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0057] More preferably, 1-1 is selected from any one of the following groups:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] R1 is the same as or different from the following groups selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene. Peryl, fluoranyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopropenyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl 9-methyl-9-phenylfluorene, 9,9′-spirodifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[cyclohexane-1,9'-fluorene], spiro-(adamantane-2,9'-fluorene), spirofluorenexanthoxanthyl, spirofluorenexazanthyl, spiroanthrafluorene, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzo[…] Dibenzothiophene, carbazolyl, 9-carbazolyl, benzocarbazolyl, indolyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenothiazinyl or phenothiazinyl, or two adjacent R1s forming a substituted or unsubstituted ring; The R is the same as or different from the following groups selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene, triphenylene, perylene, fluoranyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopropenyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, 9,9-dimethylfluorenyl, 9 9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, 9,9′-spirodifluorenyl, spiro[cyclopentane-1,9'-fluorenyl], spiro[cyclohexane-1,9'-fluorenyl], spiro-(adamantane-2,9'-fluorenyl), spirofluorenoxanthraceneyl, spirofluorenoxanthraceneyl, spirofluorenoxanthraceneyl, spiroanthrafluorenyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiazolyl Fenyl, dibenzothiophene, benzodibenzothiophene, carbazolyl, 9-carbazolyl, benzocarbazolyl, indolyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, phenothiazinyl or phenothiazinyl; The n is selected from 0, 1, or 2; the n1 is selected from 0 or 1; the m1 is selected from 0, 1, 2, 3, or 4; the m2 is selected from 0, 1, 2, 3, 4, 5, or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the m5 is selected from 0, 1, 2, or 3; the m6 is selected from 0, 1, or 2; the m7 is selected from 0 or 1; the m8 is selected from 0, 1, 2, 3, 4, or 5; and the m9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0073] Preferably, the Ar a Ar b Ar c Ar d The same or different groups are selected from any one of the following groups.

[0074]

[0075] The p that is the same as or different from is selected from CR5 or N, and is the same as L. a L b L c Ld The connected p atoms are selected from C atoms; The R5 and R5' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R5s forming a substituted or unsubstituted ring; The ring B is selected from substituted or unsubstituted C3-C10 saturated or unsaturated alicyclic rings; M is selected from O, S, and CR. a R b or NR c ; M1 is selected from O, S, or NR. d ; M2 is selected from O, S, or NR. e ; The R a R b The same or different are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent Ra and Rb forming a substituted or unsubstituted ring; The R c R d R e The same or different are selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 fused cycloalkanes; The value of e2 is selected from 0, 1, 2, 3 or 4; the value of e7 is selected from 0, 1 or 2.

[0076] Further preferably, the Ar a Ar b Ar c Ar d The same or different groups are selected from any one of the following groups.

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] The R5 and R5' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R5s forming a substituted or unsubstituted ring; The R a R b The same or different are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent Ra and Rb forming a substituted or unsubstituted ring; The R c R d R e The same or different are selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 fused cycloalkanes; The e1 is selected from 0, 1, 2, 3, 4, or 5; the e2 is selected from 0, 1, 2, 3, or 4; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the e4 is selected from 0, 1, 2, 3, 4, 5, or 6; the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the e6 is selected from 0, 1, 2, or 3; the e7 is selected from 0, 1, or 2; the e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the e 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the e 11 Choose from 0 or 1.

[0110] More preferably, R5 and R5' are the same or different from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups, including: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, etc. Pyrene, triphenylene, perylene, fluoranyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopropenyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, 9,9-dimethylfluorenyl, 9,9 -Diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9′-spirodifluorenyl, spiro[cyclopentane-1,9'-fluorenyl], spiro[cyclohexane-1,9'-fluorenyl], spiro-(adamantane-2,9'-fluorenyl), spirofluorenoxanthraceneyl, spirofluorenoxanthraceneyl, spirofluorenoxanthraceneyl, spiroanthracenefluorenyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl Benzodibenzothiophene, carbazolyl, 9-carbazolyl, benzocarbazolyl, indolyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenothiazinyl or phenothiazinyl, or two adjacent R5s forming a substituted or unsubstituted ring; More preferably, the R a R bThe same or different from the following groups selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, trimethylene, peryl, fluoranyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopropene, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, 9,9-dimethylfluorenyl, 9,9- Diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9′-spirodifluorenyl, spiro[cyclopentane-1,9'-fluorenyl], spiro[cyclohexane-1,9'-fluorenyl], spiro-(adamantane-2,9'-fluorenyl), spirofluorenoxanthenyl, spirofluorenoxanthenyl, spirofluorenoxanthenyl, spiroanthenyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, di Benzothiophene, benzodibenzothiophene, carbazole, 9-carbazole, benzocarbazole, indole, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenthiazinyl or phenoxazinyl, or two adjacent R a R b Formed with or without substituted rings; More preferably, the R c R d R eThe same or different groups selected from hydrogen, deuterium, substituted or unsubstituted groups include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluoranyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopropene, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, 9,9-dimethylfluorenyl, 9,9-diphenyl 9-methyl-9-phenylfluorene, 9,9′-spirodifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[cyclohexane-1,9'-fluorene], spiro-(adamantane-2,9'-fluorene), spirofluorenexanthoxanthyl, spirofluorenexazanthyl, spiroanthrafluorene, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene Dibenzothiophene, benzodibenzothiophene, carbazolyl, 9-carbazolyl, benzocarbazolyl, indolyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenothiazinyl or phenothiazinyl.

[0111] Further preferably, the Ar a Ar b Ar c Ar d One, two, three, or four of the groups are selected from any one of the following groups.

[0112]

[0113]

[0114] R5, R5', e1, e2, e3, e4, e6, e7, and e8 have the same meaning as described above.

[0115] Preferably, the L a L b L c L d L1, L2, and L3 are independently selected from single bonds or from any of the following groups.

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] The R6 and R6' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R6s forming a substituted or unsubstituted ring; f1 is selected from 0, 1, 2, 3 or 4; f2 is selected from 0, 1, 2, 3, 4, 5 or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is selected from 0, 1, 2 or 3; f5 is selected from 0, 1 or 2; f6 is selected from 0 or 1; f7 is selected from 0, 1, 2, 3, 4 or 5; f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0125] Preferably, R6 and R6' are the same or different from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups of the following: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene. Triphenylene, Perylene, Fluoranthryl, Trimethylsilyl, Triethylsilyl, Triisopropylsilyl, Tri-tert-butylsilyl, Triphenylsilyl, Benzocyclopropane, Benzocyclobutane, Benzocyclopentane, Benzocyclohexane, Benzocycloheptane, Benzocyclopropenyl, Benzocyclobutenyl, Benzocyclopentenyl, Benzocyclohexenyl, 9,9-Dimethylfluorenyl, 9,9- Diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9′-spirodifluorenyl, spiro[cyclopentane-1,9'-fluorenyl], spiro[cyclohexane-1,9'-fluorenyl], spiro-(adamantane-2,9'-fluorenyl), spirofluorenoxanthenyl, spirofluorenoxanthenyl, spirofluorenoxanthenyl, spiroanthenyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl Benzodibenzothiophene, carbazolyl, 9-carbazolyl, benzocarbazolyl, indolyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, phenothiazinyl or phenothiazinyl, or two adjacent R6s forming a substituted or unsubstituted ring.

[0126] Preferably, Formula 1 is selected from one of the following structures.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312] .

[0313] The above lists some specific structural forms of compounds represented by chemical formula 1 according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on chemical formula 1 with substituents as defined above should be included.

[0314] There are no particular limitations on the preparation method of the compound represented by Chemical Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, CC coupling reaction, Miyaura borylation reaction, etc., are detailed below:

[0315] The X a X b X c X d The W is independently selected from I, Br, or Cl; or ;The Q, Y, X, A, Ar a Ar b Ar c Ar d L a L b L c L d The limitations of L1, L2, and L3 are the same as those mentioned above.

[0316] The present invention also provides an organic electroluminescent device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises at least one of the nitrogen-containing heterocyclic compounds described in the present invention.

[0317] Preferably, the organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0318] Preferably, the organic layer includes an electron transport layer containing at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0319] Preferably, the organic layer includes a hole-blocking layer containing at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0320] Preferably, the organic layer comprises an electron transport layer and a hole blocking layer, wherein the electron transport layer and the hole blocking layer contain at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0321] Preferably, the organic layer includes a light-emitting layer containing at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0322] Preferably, the light-emitting layer comprises a host material containing at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0323] Preferably, the organic electroluminescent device of the present invention includes two types of structures: a single-layer structure (containing one light-emitting unit) and a stacked structure (two or more independent light-emitting units connected in series through a charge generation layer).

[0324] Preferably, the present invention provides a stacked organic electroluminescent device, comprising a first electrode, a second electrode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer, wherein the first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the first electrode and the second electrode, and the charge-generating layer is located between the first light-emitting unit and the second light-emitting unit, wherein the charge-generating layer comprises at least one of the nitrogen-containing heterocyclic compounds described in the present invention.

[0325] Preferably, the charge generation layer includes an N-type charge generation layer disposed adjacent to the first light-emitting unit and a P-type charge generation layer disposed adjacent to the second light-emitting unit, wherein the N-type charge generation layer contains at least one of the nitrogen-containing heterocyclic compounds described in this invention.

[0326] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The anode material described in this invention is preferably a material with high work function, good conductivity, and good chemical stability. The anode material can be selected from transparent metal oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO); it can be selected from high work function metals, such as gold (Au), copper (Cu), and platinum (Pt); it can also be selected from conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxothiophene] (PEDOT), poly(3,4-ethylenedioxothiophene) / polystyrene sulfonic acid (PEDOT:PSS), polypyrrole, and polyaniline, but is not limited thereto.

[0327] The hole injection layer material described in this invention is preferably a material with good hole injection capability, thereby reducing the potential barrier for holes injected from the anode to the organic layer, improving hole injection efficiency, and balancing carrier injection. The hole injection layer material can be selected from metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene, but is not limited to these.

[0328] The hole transport layer material described in this invention preferably possesses high hole mobility, good thermal stability, film-forming properties, and suitable HOMO orbital energy levels. The hole transport layer material can be selected from, but is not limited to, benzidine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc.

[0329] The electron blocking layer material of the present invention is preferably a material with good hole transport capability and electron blocking capability, so as to effectively transport holes and restrict electrons from escaping to the light-emitting layer interface. The electron blocking layer material can be an aromatic amine derivative, a carbazole derivative, etc., but is not limited thereto.

[0330] The luminescent layer material of this invention includes a host material and a dopant material. The host material of the luminescent layer needs to possess bipolar charge transport properties and have suitable energy levels. Besides the compounds provided by this invention, the host material of the luminescent layer can also be selected from aromatic fused-ring derivatives, such as anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc.; it can also be selected from heterocyclic compounds, such as carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but is not limited thereto. The dopant material is divided into blue luminescent materials, green luminescent materials, and red luminescent materials. The dopant material of the luminescent layer can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, selected from metal complexes, such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, terbium complexes, europium complexes, etc.; anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., but is not limited thereto. Nitrogen-containing heterocyclic compounds of this invention are preferred.

[0331] The charge generation layer material described in this invention includes N-type charge generation materials and P-type charge generation materials.

[0332] The N-type charge-generating layer material described in this invention preferably possesses high electron mobility, strong electron-withdrawing properties, and good chemical stability to achieve efficient electron injection and transport. Besides the compounds provided in this invention, the N-type charge-generating layer material can be selected from, but is not limited to, tris-(8-hydroxyquinoline)aluminum (Alq3), spiro-PBD, lithium quinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). Furthermore, auxiliary N-type charge-generating materials may also be included. These auxiliary materials can be selected from alkali metals, such as Li, Cs, K, Rb, Na, or Fr; or alkaline earth metals, such as Be, Mg, Ca, Sr, Ba, or Ra, but are not limited to these. The nitrogen-containing heterocyclic compound described in this invention is preferred.

[0333] The P-type charge generation layer material of this invention is preferably a material with high hole injection and transport capabilities, and achieves charge separation and balance through composite with N-type materials. The P-type charge generation layer material can be selected from, but is not limited to, 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPD), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazolyl-3-yl)phenyl)-9H-fluorene-2-amine, etc.

[0334] The hole-blocking layer material of this invention preferably effectively blocks excessive injection of holes into the electron transport layer while promoting electron transport, ensuring efficient exciton transport within the emissive layer. Besides the compounds provided by this invention, the hole-blocking layer material can be selected from phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto. Nitrogen-containing heterocyclic compounds of this invention are preferred.

[0335] The electron transport layer material described in this invention preferably possesses high electron mobility, good thermal stability and film-forming properties, and a suitable energy level structure. Besides the compounds provided in this invention, the electron transport layer can be selected from, but is not limited to, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and 4,7-diphenyl-1,10-phenanthroline (Bphen). Nitrogen-containing heterocyclic compounds described in this invention are preferred.

[0336] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. The electron injection layer material can be selected from alkali metal compounds, such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinoline, aluminum 8-hydroxyquinoline, etc.; it can also be selected from organometallic salts, such as metal acetates, metal benzoates, or metal stearates; molybdenum trioxide, aluminum, etc., but is not limited to these.

[0337] The cathode material described in this invention preferably possesses low work function, good chemical stability, and efficient electron injection. The cathode can be selected from low work function metals and alloys, such as silver (Ag), magnesium (Mg), aluminum (Al), calcium (Ca), magnesium-silver alloy (Mg:Ag), magnesium-aluminum alloy (Mg:Al), and aluminum-lithium alloy (Al:Li); it can also be selected from composite electrode materials, such as LiF / Al, CsF / Al, CaF2 / Al, and BaF2 / Al, but is not limited thereto.

[0338] The capping layer described in this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the optical coupling efficiency inside the device. The capping layer material can be selected from arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., but is not limited to these.

[0339] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0340] The organic electroluminescent device described in this invention can be applied using vacuum evaporation, pulsed laser deposition, spin coating, inkjet printing, vapor deposition, doctor blade coating, electrospray coating, slot coating, dip coating, etc., but is not limited to these methods.

[0341] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0342] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting technology, flexible electronics and wearable devices, medical and health fields, and other fields.

[0343] Raw materials and reagents: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.

[0344] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0345] Synthesis Example 1: Preparation of raw material c-60

[0346] Preparation of raw material c-60: Under nitrogen protection, f-60 (34.78 g, 100.00 mmol), pinacol diboronate (25.39 g, 100.00 mmol), K2CO3 (24.88 g, 180.00 mmol), Pd(dppf)Cl2 (0.73 g, 1.00 mmol), and 500 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain raw material c-60 (36.47 g, 83%), with an HPLC purity ≥99.82% and a mass spectrometry m / z of 439.2357 (theoretical value: 439.2369). Synthesis Example 2: Preparation of raw material b-82

[0347] Following the same preparation method as raw material c-60 in synthesis Example 1, f-60 was replaced with an equimolar amount of f-82 to obtain raw material b-82 (27.32 g, 81%), with a solid purity of ≥99.84% as determined by HPLC. Mass spectrometry m / z: 337.1319 (theoretical value: 337.1308).

[0348] Synthesis Example 3: Preparation of raw material b-735

[0349] Following the same preparation method as raw material c-60 in synthesis Example 1, f-60 was replaced with an equimolar amount of f-735 to obtain raw material b-735 (30.98 g, 80%), with a solid purity of ≥99.80% as determined by HPLC. Mass spectrometry m / z: 387.1483 (theoretical value: 387.1464).

[0350] Synthesis Example 4: Preparation of raw material d-436

[0351] Preparation of raw material d-436: Under nitrogen protection, g-436 (22.61 g, 100.00 mmol), h-436 (26.81 g, 100.00 mmol), Pd(dppf)Cl2 (0.73 g, 1.00 mmol), and K2CO3 (24.88 g, 180.00 mmol), along with 500 mL of toluene / ethanol / water (2:1:1), were added to a reaction flask. The mixture was stirred and refluxed for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid using toluene / ethanol (8:1 ratio). The solid was dried to obtain intermediate d-436 (34.35 g, yield 83%). HPLC analysis showed that the purity of the solid was ≥99.80%. Mass spectrometry m / z: 413.1279 (theoretical value: 413.1295).

[0352] Synthesis Example 5: Preparation of raw material d-518

[0353] Following the same preparation method as raw material d-436 in synthesis Example 4, g-436 was replaced with an equimolar amount of g-518, and h-436 was replaced with an equimolar amount of h-518, yielding raw material d-518 (31.67 g, 80%). HPLC analysis showed a solid purity ≥99.81%. Mass spectrometry m / z: 395.0920 (theoretical value: 395.0938).

[0354] Synthesis Example 6: Preparation of raw material d-732

[0355] Following the same preparation method as raw material d-436 in synthesis Example 4, g-436 was replaced with an equimolar amount of g-518, and h-436 was replaced with an equimolar amount of h-732, yielding raw material d-732 (32.55 g, 81%). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 401.0518 (theoretical value: 401.0502).

[0356] Synthesis Example 7: Preparation of Compound 5

[0357] Preparation of intermediate A-5: Under nitrogen protection, a-5 (25.39 g, 80.00 mmol), b-5 (14.24 g, 80.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and K2CO3 (16.59 g, 120.00 mmol), along with 800 mL of toluene / ethanol / water (2:1:1), were added to a reaction flask. The mixture was stirred and refluxed for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol (8:1 ratio). The solid was dried to obtain intermediate A-5 (20.97 g, yield 81%). HPLC analysis showed a solid purity ≥99.86%. Mass spectrometry m / z: 321.9201 (theoretical value: 321.9219).

[0358] Preparation of intermediate B-5: Under nitrogen protection, intermediates A-5 (19.42 g, 60.00 mmol), c-5 (21.19 g, 60.00 mmol), K2CO3 (12.44 g, 90.00 mmol), Pd(dppf)Cl2 (0.44 g, 0.60 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 6 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in a 7:1 ratio to obtain intermediate B-5 (26.17 g, 79%), with an HPLC purity ≥99.84%. Mass spectrometry m / z: 551.1235 (theoretical value: 551.1223).

[0359] Preparation of intermediate C-5: Under nitrogen protection, intermediate B-5 (22.08 g, 40.00 mmol), pinacol diborate (10.16 g, 40.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd(dppf)Cl2 (0.29 g, 0.40 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate C-5 (20.08 g, 78%) with an HPLC purity ≥ 99.81%. Mass spectrometry m / z: 643.2450 (theoretical value: 643.2465).

[0360] Preparation of Compound 5: Under nitrogen protection, C-5 (12.87 g, 20.00 mmol), d-5 (5.35 g, 20.00 mmol), K2CO3 (4.15 g, 30.00 mmol), Pd(PPh3)4 (0.18 g, 0.20 mmol), and 200 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 8 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol (8:1) to obtain Compound 5 (11.08 g, 74%), with an HPLC purity ≥99.97% and a mass spectrometry m / z of 748.2424 (theoretical value: 748.2409). Theoretical elemental content (%) C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.15; H, 4.36; N, 11.19.

[0361] Synthesis Example 8: Preparation of Compound 28

[0362] Following the same preparation method as compound 5 in synthesis example 7, a-5 was replaced with an equimolar amount of a-28, b-5 with an equimolar amount of b-28, and c-5 with an equimolar amount of c-28, yielding compound 28 (10.93 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 748.2418 (theoretical value: 748.2409). Theoretical elemental content (%) C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.16; H, 4.34; N, 11.23.

[0363] Synthesis Example 9: Preparation of Compound 30

[0364] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, and c-5 with an equimolar amount of c-28, yielding compound 30 (11.08 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 748.2426 (theoretical value: 748.2409). Theoretical elemental content (%) C 50 H 32N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.22; H, 4.36; N, 11.25.

[0365] Synthesis Example 10: Preparation of Compound 33

[0366] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-33, and c-5 with an equimolar amount of c-28 to obtain compound 33 (10.93 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 748.2420 (theoretical value: 748.2409). Theoretical elemental content (%) C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.21; H, 4.29; N, 11.18.

[0367] Synthesis Example 11: Preparation of Compound 53

[0368] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-53, and b-5 was replaced with an equimolar amount of b-53, yielding compound 53 (11.08 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 748.2398 (theoretical value: 748.2409). Theoretical elemental content (%) C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.23; H, 4.27; N, 11.19.

[0369] Synthesis Example 12: Preparation of Compound 60

[0370] Following the same preparation method as compound 5 in synthesis example 7, a-5 was replaced with an equimolar amount of a-30, and c-5 was replaced with an equimolar amount of c-60, yielding compound 60 (10.84 g), with HPLC purity ≥99.98% and mass spectrometry m / z: 752.2671 (theoretical value: 752.2660). Theoretical elemental content (%) C 50 H 28D4N6S: C, 79.76; H, 4.82; N, 11.16. Measured elemental content (%): C, 79.74; H, 4.84; N, 11.19.

[0371] Synthesis Example 13: Preparation of Compound 65

[0372] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-65, yielding compound 65 (11.19 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 776.2710 (theoretical value: 776.2722). Theoretical elemental content (%) C 52 H 36 N6S: C, 80.39; H, 4.67; N, 10.82. Measured elemental content (%): C, 80.42; H, 4.65; N, 10.84.

[0373] Synthesis Example 14: Preparation of Compound 78

[0374] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-78, and c-5 was replaced with an equimolar amount of c-28, yielding compound 78 (11.72 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 824.2736 (theoretical value: 824.2722). Theoretical elemental content (%) C 56 H 36 N6S: C, 81.53; H, 4.40; N, 10.19. Measured elemental content (%): C, 81.50; H, 4.42; N, 10.15.

[0375] Synthesis Example 15: Preparation of Compound 82

[0376] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-53, b-5 with an equimolar amount of b-82, and c-5 with an equimolar amount of c-28, yielding compound 82 (11.56 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 825.2688 (theoretical value: 825.2675). Theoretical elemental content (%) C 55 H 35N7S: C, 79.98; H, 4.27; N, 11.87. Measured elemental content (%): C, 79.99; H, 4.26; N, 11.89.

[0377] Synthesis Example 16: Preparation of Compound 106

[0378] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-106, b-5 with an equimolar amount of b-106, and c-5 with an equimolar amount of c-28, yielding compound 106 (11.51 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 798.2555 (theoretical value: 798.2566). Theoretical elemental content (%) C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.16; H, 4.32; N, 10.50.

[0379] Synthesis Example 17: Preparation of Compound 123

[0380] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, and d-5 with an equimolar amount of d-123 to obtain compound 123 (12.05 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 824.2739 (theoretical value: 824.2722). Theoretical elemental content (%) C 56 H 36 N6S: C, 81.53; H, 4.40; N, 10.19. Measured elemental content (%): C, 81.50; H, 4.44; N, 10.22.

[0381] Synthetic Example 18: Preparation of Compound 155

[0382] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-155, yielding compound 155 (12.07 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 849.2662 (theoretical value: 849.2675). Theoretical elemental content (%) C57 H 35 N7S: C, 80.54; H, 4.15; N, 11.53. Measured elemental content (%): C, 80.51; H, 4.13; N, 11.56.

[0383] Synthetic Example 19: Preparation of Compound 158

[0384] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-106, b-5 with an equimolar amount of b-158, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-158, yielding compound 158 (12.62 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 900.3050 (theoretical value: 900.3035). Theoretical elemental content (%) C 62 H 40 N6S: C, 82.64; H, 4.47; N, 9.33. Measured elemental content (%): C, 82.65; H, 4.49; N, 9.31.

[0385] Synthesis Example 20: Preparation of Compound 239

[0386] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-239, yielding compound 239 (11.66 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 798.2577 (theoretical value: 798.2566). Theoretical elemental content (%) C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.20; H, 4.27; N, 10.50.

[0387] Synthesis Example 21: Preparation of Compound 254

[0388] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-33, and d-5 with an equimolar amount of d-254, yielding compound 254 (12.43 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 874.2864 (theoretical value: 874.2879). Theoretical elemental content (%) C 60 H 38 N6S: C, 82.35; H, 4.38; N, 9.60. Measured elemental content (%): C, 82.34; H, 4.39; N, 9.62.

[0389] Synthesis Example 22: Preparation of Compound 357

[0390] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-53, b-5 with an equimolar amount of b-357, and d-5 with an equimolar amount of d-357, yielding compound 357 (11.89 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 848.2736 (theoretical value: 848.2722). Theoretical elemental content (%) C 58 H 36 N6S: C, 82.05; H, 4.27; N, 9.90. Measured elemental content (%): C, 82.06; H, 4.25; N, 9.93.

[0391] Synthesis Example 23: Preparation of Compound 366

[0392] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-366, yielding compound 366 (12.41 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 898.2870 (theoretical value: 898.2879). Theoretical elemental content (%) C 62 H 38 N6S: C, 82.83; H, 4.26; N, 9.35. Measured elemental content (%): C, 82.81; H, 4.25; N, 9.37.

[0393] Synthesis Example 24: Preparation of Compound 393

[0394] Following the same preparation method as compound 5 in Synthesis Example 7, c-5 was replaced with an equimolar amount of c-28, and d-5 was replaced with an equimolar amount of d-393, yielding compound 393 (12.11 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 864.3047 (theoretical value: 864.3035). Theoretical elemental content (%) C 59 H 40 N6S: C, 81.92; H, 4.66; N, 9.72. Measured elemental content (%): C, 81.91; H, 4.67; N, 9.76.

[0395] Synthesis Example 25: Preparation of Compound 395

[0396] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-395, yielding compound 395 (13.65 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 988.3340 (theoretical value: 988.3348). Theoretical elemental content (%) C 69 H 44 N6S: C, 83.78; H, 4.48; N, 8.50. Measured elemental content (%): C, 83.76; H, 4.49; N, 8.53.

[0397] Synthesis Example 26: Preparation of Compound 398

[0398] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-398, b-5 with an equimolar amount of b-398, and c-5 with an equimolar amount of c-398, yielding compound 398 (13.23 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 986.3180 (theoretical value: 986.3192). Theoretical elemental content (%) C 69 H 42 N6S: C, 83.95; H, 4.29; N, 8.51. Measured elemental content (%): C, 83.91; H, 4.26; N, 8.53.

[0399] Synthesis Example 27: Preparation of Compound 400

[0400] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-33, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-400, yielding compound 400 (13.04 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1002.3153 (theoretical value: 1002.3141). Theoretical elemental content (%) C 69 H 42 N6OS: C, 82.61; H, 4.22; N, 8.38. Measured elemental content (%): C, 82.63; H, 4.25; N, 8.39.

[0401] Synthesis Example 28: Preparation of Compound 405

[0402] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-357, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-405, yielding compound 405 (12.08 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 838.2500 (theoretical value: 838.2515). Theoretical elemental content (%) C 56 H 34 N6OS: C, 80.17; H, 4.08; N, 10.02. Measured elemental content (%): C, 80.16; H, 4.05; N, 10.03.

[0403] Synthesis Example 29: Preparation of Compound 423

[0404] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-423, yielding compound 423 (12.45 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 888.2688 (theoretical value: 888.2671). Theoretical elemental content (%) C 60 H 36 N6OS: C, 81.06; H, 4.08; N, 9.45. Measured elemental content (%): C, 81.05; H, 4.07; N, 9.44.

[0405] Synthesis Example 30: Preparation of Compound 428

[0406] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-428, yielding compound 428 (11.59 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 839.2483 (theoretical value: 839.2467). Theoretical elemental content (%) C 55 H 33 N7OS: C, 78.65; H, 3.96; N, 11.67. Measured elemental content (%): C, 78.63; H, 3.97; N, 11.69.

[0407] Synthesis Example 31: Preparation of Compound 436

[0408] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-357, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-436, yielding compound 436 (12.35 g). HPLC purity ≥ 99.97%, mass spectrometry m / z: 894.3132 (theoretical value: 894.3141). Theoretical elemental content (%) C 60 H 42 N6OS: C, 80.51; H, 4.73; N, 9.39. Measured elemental content (%): C, 80.50; H, 4.75; N, 9.37.

[0409] Synthesis Example 32: Preparation of Compound 442

[0410] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-33, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-442, yielding compound 442 (13.04 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 930.2582 (theoretical value: 930.2599). Theoretical elemental content (%) C 62 H 38N6S2: C, 79.97; H, 4.11; N, 9.03. Measured elemental content (%): C, 79.95; H, 4.13; N, 9.05.

[0411] Synthesis Example 33: Preparation of Compound 466

[0412] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-466, yielding compound 466 (12.30 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 865.2640 (theoretical value: 865.2624). Theoretical elemental content (%) C 57 H 35 N7OS: C, 79.05; H, 4.07; N, 11.32. Measured elemental content (%): C, 79.06; H, 4.09; N, 11.30.

[0413] Synthesis Example 34: Preparation of Compound 482

[0414] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-357, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-482, yielding compound 482 (12.12 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 865.2610 (theoretical value: 865.2624). Theoretical elemental content (%) C 57 H 35 N7OS: C, 79.05; H, 4.07; N, 11.32. Measured elemental content (%): C, 79.07; H, 4.05; N, 11.31.

[0415] Synthesis Example 35: Preparation of Compound 514

[0416] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-514, yielding compound 514 (11.89 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 825.2693 (theoretical value: 825.2675). Theoretical elemental content (%) C 55 H 35 N7S: C, 79.98; H, 4.27; N, 11.87. Measured elemental content (%): C, 79.96; H, 4.25; N, 11.91.

[0417] Synthesis Example 36: Preparation of Compound 518

[0418] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-33, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-518, yielding compound 518 (12.10 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 876.2770 (theoretical value: 876.2784). Theoretical elemental content (%) C 58 H 36 N8S: C, 79.43; H, 4.14; N, 12.78. Measured elemental content (%): C, 79.42; H, 4.13; N, 12.79.

[0419] Synthesis Example 37: Preparation of Compound 520

[0420] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-520, yielding compound 520 (12.26 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 875.2847 (theoretical value: 875.2831). Theoretical elemental content (%) C 59 H 37 N7S: C, 80.89; H, 4.26; N, 11.19. Measured elemental content (%): C, 80.92; H, 4.24; N, 11.15.

[0421] Synthesis Example 38: Preparation of Compound 521

[0422] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-28, b-5 with an equimolar amount of b-53, and c-5 with an equimolar amount of c-521, yielding compound 521 (11.66 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 798.2553 (theoretical value: 798.2566). Theoretical elemental content (%) C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.19; H, 4.25; N, 10.57.

[0423] Synthesis Example 39: Preparation of Compound 529

[0424] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-28, and c-5 was replaced with an equimolar amount of c-529, yielding compound 529 (11.35 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 798.2585 (theoretical value: 798.2566). Theoretical elemental content (%) C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.15; H, 4.26; N, 10.53.

[0425] Synthesis Example 40: Preparation of Compound 538

[0426] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-106, b-5 with an equimolar amount of b-33, and c-5 with an equimolar amount of c-538, yielding compound 538 (11.35 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 798.2554 (theoretical value: 798.2566). Theoretical elemental content (%) C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.20; H, 4.23; N, 10.58.

[0427] Synthetic Example 41: Preparation of Compound 554

[0428] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-33, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-554, yielding compound 554 (11.88 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 824.2739 (theoretical value: 824.2722). Theoretical elemental content (%) C 56 H 36 N6S: C, 81.53; H, 4.40; N, 10.19. Measured elemental content (%): C, 81.50; H, 4.42; N, 10.17.

[0429] Synthesis Example 42: Preparation of Compound 557

[0430] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, and c-5 with an equimolar amount of c-557, yielding compound 557 (11.40 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 825.2660 (theoretical value: 825.2675). Theoretical elemental content (%) C 55 H 35 N7S: C, 79.98; H, 4.27; N, 11.87. Measured elemental content (%): C, 79.97; H, 4.26; N, 11.88.

[0431] Synthesis Example 43: Preparation of Compound 566

[0432] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-53, and c-5 with an equimolar amount of c-566, yielding compound 566 (11.72 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 824.2710 (theoretical value: 824.2722). Theoretical elemental content (%) C 56 H 36 N6S: C, 81.53; H, 4.40; N, 10.19. Measured elemental content (%): C, 81.55; H, 4.43; N, 10.17.

[0433] Synthesis Example 44: Preparation of Compound 608

[0434] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-398, and c-5 with an equimolar amount of c-608, yielding compound 608 (11.55 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 824.2713 (theoretical value: 824.2722). Theoretical elemental content (%) C 58 H 36 N6S: C, 82.05; H, 4.27; N, 9.90. Measured elemental content (%): C, 82.07; H, 4.29; N, 9.93.

[0435] Synthesis Example 45: Preparation of Compound 611

[0436] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-53, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-611, yielding compound 611 (10.92 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 747.2441 (theoretical value: 747.2457). Theoretical elemental content (%) C 51 H 33 N5S: C, 81.90; H, 4.45; N, 9.36. Measured elemental content (%): C, 81.94; H, 4.49; N, 9.39.

[0437] Synthesis Example 46: Preparation of Compound 617

[0438] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-617, and d-5 with an equimolar amount of d-617, yielding compound 617 (11.05 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 746.2519 (theoretical value: 746.2504). Theoretical elemental content (%) C 52 H 34 N4S: C, 83.62; H, 4.59; N, 7.50. Measured elemental content (%): C, 83.61; H, 4.57; N, 7.53.

[0439] Synthesis Example 47: Preparation of Compound 621

[0440] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-621, yielding compound 621 (10.91 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 746.2520 (theoretical value: 746.2504). Theoretical elemental content (%) C 52 H 34 N4S: C, 83.62; H, 4.59; N, 7.50. Measured elemental content (%): C, 83.60; H, 4.56; N, 7.53.

[0441] Synthesis Example 48: Preparation of Compound 623

[0442] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-623, yielding compound 623 (11.04 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 745.2540 (theoretical value: 745.2552). Theoretical elemental content (%) C 53 H 35 N3S: C, 85.34; H, 4.73; N, 5.63. Measured elemental content (%): C, 85.30; H, 4.75; N, 5.66.

[0443] Synthesis Example 49: Preparation of Compound 732

[0444] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-357, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-732, yielding compound 732 (12.01 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 882.2335 (theoretical value: 882.2348). Theoretical elemental content (%) C 56 H 34 N8S2: C, 76.17; H, 3.88; N, 12.69. Measured elemental content (%): C, 76.19; H, 3.84; N, 12.66.

[0445] Synthesis Example 50: Preparation of Compound 733

[0446] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-53, c-5 with an equimolar amount of c-733, and d-5 with an equimolar amount of d-733, yielding compound 733 (10.93 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 758.3020 (theoretical value: 758.3037). Theoretical elemental content (%) C 50 H 22 D 10 N6S: C, 79.13; H, 5.58; N, 11.07. Measured elemental content (%): C, 79.17; H, 5.56; N, 11.08.

[0447] Synthesis Example 51: Preparation of Compound 735

[0448] Following the same preparation method as compound 5 in Synthesis Example 7, b-5 was replaced with an equimolar amount of b-735, and c-5 was replaced with an equimolar amount of c-28, yielding compound 735 (11.74 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 875.2842 (theoretical value: 875.2831). Theoretical elemental content (%) C 59 H 37 N7S: C, 80.89; H, 4.26; N, 11.19. Measured elemental content (%): C, 80.92; H, 4.25; N, 11.22.

[0449] Synthesis Example 52: Preparation of Compound 738

[0450] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-738, c-5 with an equimolar amount of c-738, and d-5 with an equimolar amount of d-738, yielding compound 738 (12.64 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 956.3650 (theoretical value: 956.3661). Theoretical elemental content (%) C 66 H 48N6S: C, 82.82; H, 5.05; N, 8.78. Measured elemental content (%): C, 82.83; H, 5.06; N, 8.79.

[0451] Synthesis Example 53: Preparation of Compound 768

[0452] Following the same preparation method as compound 5 in Synthesis Example 7, a-5 was replaced with an equimolar amount of a-30, b-5 with an equimolar amount of b-28, c-5 with an equimolar amount of c-28, and d-5 with an equimolar amount of d-768, yielding compound 768 (11.82 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 820.2820 (theoretical value: 820.2804). Theoretical elemental content (%) C 53 H 40 N6SSi: C, 77.53; H, 4.91; N, 10.24. Measured elemental content (%): C, 77.55; H, 4.93; N, 10.22.

[0453] [Device Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0454] The ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 10 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0455] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate, consisting of a hole injection layer HI-1:HT-1 = 1:99 (10 nm); a hole transport layer HT-1 (110 nm); an emitting layer BH:BD = 99:1 (mass ratio, 20 nm); an electron transport layer compound 5:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1 nm); a cathode Mg:Ag = 1:9 (mass ratio, 11 nm); and a capping layer CP (80 nm).

[0456]

[0457]

[0458] [Device Examples 2-47]

[0459] Using compounds 28, 30, 33, 53, 60, 65, 78, 82, 106, 123, 155, 158, 239, 254, 357, 366, 393, 395, 398, 400, 405, 423, 428, 436, 442, 466, 482, and others of the present invention. Compounds 514, 518, 520, 521, 529, 538, 554, 557, 566, 608, 611, 617, 621, 623, 732, 733, 735, 738, and 768 were used to replace compound 5 in device example 1 as the electron transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0460] [Comparative Device Examples 1-3]

[0461] Compounds E-1, E-2, and E-3 were used to replace compound 5 in device example 1 as electron transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0462] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage and luminous efficiency of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The system was tested at a current density of 10 mA / cm². 2 Under certain conditions, the driving voltage, luminous efficiency, and time (h) required for the brightness of the organic electroluminescent device to decay to 95% of its initial brightness were tested.

[0463] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-47 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-3 are shown in Table 1 below.

[0464] Table 1:

[0465]

[0466] As shown in Table 1, when the nitrogen-containing heterocyclic compound described in this invention is applied to the electron transport material of organic electroluminescent devices, the device exhibits higher luminous efficiency, longer lifespan, and lower driving voltage. The compound of this invention is a high-performance electron transport material.

[0467] [Device Example 48] Fabrication of Green Organic Electroluminescent Device

[0468] The ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 10 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0469] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate, consisting of: a hole injection layer HI-1:HT-2 = 1:99 (10 nm); a hole transport layer HT-2 (110 nm); an electron blocking layer EB-1 (5 nm); a light-emitting layer GH-1:GH-2:GD = 46:46:8 (mass ratio, 20 nm); a hole blocking layer compound 5 (5 nm); an electron transport layer ET-1:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1 nm); a cathode Mg:Ag = 1:9 (mass ratio, 11 nm); and a capping layer CP (80 nm).

[0470]

[0471]

[0472] [Device Examples 49-94]

[0473] Using compounds 28, 30, 33, 53, 60, 65, 78, 82, 106, 123, 155, 158, 239, 254, 357, 366, 393, 395, 398, 400, 405, 423, 428, 436, 442, 466, 482, and 5 of the present invention. 14. Compounds 518, 520, 521, 529, 538, 554, 557, 566, 608, 611, 617, 621, 623, 732, 733, 735, 738, and 768 are used to replace compound 5 in device example 48 as hole blocking layer materials. Otherwise, organic electroluminescent devices are prepared using the same preparation method as in device example 48.

[0474] [Comparative Device Examples 4-5]

[0475] Compounds E-4 and E-5 were used to replace compound 5 in device example 48 as hole blocking layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 48.

[0476] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage and luminous efficiency of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The system was tested at a current density of 10 mA / cm². 2 Under certain conditions, the driving voltage, luminous efficiency, and time (h) required for the brightness of the organic electroluminescent device to decay to 95% of its initial brightness were tested.

[0477] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 48-94 in the device embodiments of this invention, and those obtained in comparative embodiments 4-5 are shown in Table 2 below.

[0478] Table 2:

[0479]

[0480] As shown in Table 2, when the nitrogen-containing heterocyclic compound described in this invention is applied to the hole blocking layer material of organic electroluminescent devices, the device has higher luminous efficiency, longer lifespan, and lower driving voltage. The compound of this invention is a hole blocking layer material with good performance.

[0481] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A nitrogen-containing heterocyclic compound, characterized in that, It is represented by the following equation 1, A is selected from formula 1-1. The z that are the same or different are selected from CR1 or N, and the z that are bonded to L3 are selected from C atoms; The R1s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R1s forming a substituted or unsubstituted ring. The R is the same or different from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings; The n is selected from 0, 1, or 2; The Y values, whether identical or different, are selected from CR2 or N, and at least one Y is N, and is related to L. a L b The bonded Y atoms are selected from C atoms; The R2s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R2s forming a substituted or unsubstituted ring. The X that is the same as or different from is selected from CR3 or N, and is related to L. c L d The X atoms in the bond are selected from C atoms; The R3s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R3s forming a substituted or unsubstituted ring. The same or different Qs are selected from CR4 or N, and the Qs bonded to L1, L2, and L3 are selected from C atoms; The R4s, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, or adjacent R4s forming a substituted or unsubstituted ring. The Ar a Ar b Ar c Ar d The same or different are selected from substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, substituted or unsubstituted cycloalkyl groups of C3-C12, or fused cycloalkanes of C3-C10 alicyclic and C6-C30 aromatic rings, respectively. The L a L b L c L d L1, L2, and L3 are the same or different from single bonds, substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C2-C30 heteroarylene groups, substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic rings, and L1 and L2 are not simultaneously selected from single bonds.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, Equation 1 is selected from any of the structures shown below. The Q, A, Ar a Ar b Ar c Ar d L a L b L c L d L1, L2, L3, R2, and R3 have the meanings defined in claim 1; s1 is selected from 0 or 1; s2 is selected from 0, 1 or 2; t1 is selected from 0 or 1; t2 is selected from 0, 1 or 2; t3 is selected from 0, 1, 2 or 3.

3. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The From any of the following groups Indicates the connection site. The R4 has the meaning as defined in claim 1.

4. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, Formula 1-1 is selected from any one of the following groups. R1 and R have the meanings defined as in claim 1; The n is selected from 0, 1, or 2; the m1 is selected from 0, 1, 2, 3, or 4; the m2 is selected from 0, 1, 2, 3, 4, 5, or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the m4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the m5 is selected from 0, 1, 2, or 3; the m6 is selected from 0, 1, or 2; the m7 is selected from 0 or 1; the m8 is selected from 0, 1, 2, 3, 4, or 5; and the m9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

5. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The Ar a Ar b Ar c Ar d The same or different groups are selected from any one of the following groups. The p that is the same as or different from is selected from CR5 or N, and is the same as L. a L b L c L d The connected p atoms are selected from C atoms; The R5 and R5' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R5s forming a substituted or unsubstituted ring; The ring B is selected from substituted or unsubstituted C3-C10 saturated or unsaturated alicyclic rings; M is selected from O, S, and CR. a R b or NR c ; M1 is selected from O, S, or NR. d ; M2 is selected from O, S, or NR. e ; The R a R b The same or different are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent Ra and Rb forming a substituted or unsubstituted ring; The R c R d R e The same or different are selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 fused cycloalkanes; The value of e2 is selected from 0, 1, 2, 3 or 4; the value of e7 is selected from 0, 1 or 2.

6. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The Ar a Ar b Ar c Ar d Selected from any one of the following groups, The R5 and R5' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R5s forming a substituted or unsubstituted ring; The R a R b The same or different from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloyl groups, or two adjacent R groups. a R b Formed with or without substituted rings; The R c R d R e The same or different are selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 fused cycloalkanes; The e1 is selected from 0, 1, 2, 3, 4, or 5; the e2 is selected from 0, 1, 2, 3, or 4; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the e4 is selected from 0, 1, 2, 3, 4, 5, or 6; the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the e6 is selected from 0, 1, 2, or 3; the e7 is selected from 0, 1, or 2; the e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the e 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the e 11 Choose from 0 or 1.

7. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The L a L b L c L d L1, L2, and L3 are independently selected from single bonds or any of the following structures: The R6 and R6' are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or substituted or unsubstituted C3-C10 alicyclic and C6-C30 aromatic fused cycloalcohol, or two adjacent R6s forming a substituted or unsubstituted ring; f1 is selected from 0, 1, 2, 3 or 4; f2 is selected from 0, 1, 2, 3, 4, 5 or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is selected from 0, 1, 2 or 3; f5 is selected from 0, 1 or 2; f6 is selected from 0 or 1; f7 is selected from 0, 1, 2, 3, 4 or 5; f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

8. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, Equation 1 is selected from one of the following structures: 。 9. An organic electroluminescent device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, characterized in that one or more of the organic layers contain at least one of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that, The organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 8.

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