Nitrogen-containing compound and organic electroluminescent device thereof

Abstract

The invention provides a nitrogen-containing compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The nitrogen-containing compound shown in the formula 1 has the properties of relatively good thermal stability, relatively good film-forming property, relatively high triplet state energy level and the like, can form a stable and good film, can effectively balance holes and electrons in a device as a host material of a luminescent layer, and can effectively prevent energy from flowing back from a guest material to the host material, so that the luminous efficiency of the device is improved. The performance of the device is effectively improved, and specifically, the device has high luminous efficiency and long service life.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that uses organic materials to emit light through carrier injection and recombination under the influence of an electric field. They convert electrical energy into light energy through organic light-emitting materials. Compared to traditional LCDs, OLEDs offer advantages such as self-illumination, high contrast, wide viewing angle, fast response time, and flexibility.

[0003] Organic light-emitting devices typically consist of an anode, a cathode, and an organic layer. In most cases, to improve the efficiency and stability of organic light-emitting elements, the organic layer is designed as a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer.

[0004] Driven by an electric field, injected electrons and holes recombine in the luminescent layer to form excitons. These excitons then release photons through radiative transitions, and the emission wavelength is determined by the molecular energy level difference of the material. The luminescent layer can be a single luminescent material or a system in which the host material is doped with a small amount of fluorescent or phosphorescent guest material. By selecting different materials and doping methods, different colors of light can be emitted.

[0005] Organic electroluminescence (OLED) technology has secured a significant position in the high-end display field due to its unique advantages, but its further development still depends on innovative breakthroughs in emissive layer materials and device structures. Existing OLED emissive layer materials still suffer from bottlenecks in efficiency and lifespan, resulting in product performance and reliability failing to meet requirements. Therefore, the development of new emissive layer materials has become a key research focus. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides a nitrogen-containing compound and its organic electroluminescent device.

[0007] This invention provides a nitrogen-containing compound, represented by the following formula 1,

[0008]

[0009] The Ar is selected from the following groups.

[0010]

[0011] The R1s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring.

[0012] The n1 is selected from integers from 0 to 4, and the n2 is selected from integers from 0 to 3;

[0013] The Xs that are the same or different are selected from CH or N, and at most one X is N;

[0014] The L is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups;

[0015] X1 and X2 are independently selected from single bonds, O, S, and C(R). x )2; The R x The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x They bond together to form substituted or unsubstituted rings;

[0016] The rings A, B, and C are independently selected from one of the following: substituted or unsubstituted aromatic rings of C6 to C30, substituted or unsubstituted fused polycyclic aromatic rings of C6 to C30, or substituted or unsubstituted heteroaromatic rings of C2 to C30.

[0017] In addition, the present invention also provides an organic electroluminescent device containing the nitrogen-containing compound of the present invention described above.

[0018] Beneficial effects: The nitrogen-containing compound of Formula 1 of this invention has good thermal stability, good film-forming properties and high triplet energy level, which can form a stable and good thin film. As the main material of the light-emitting layer, it can effectively balance the holes and electrons in the device and effectively prevent the backflow of energy from the guest material to the host material, thus effectively improving the performance of the device. Specifically, it has high luminous efficiency and long service life. Detailed Implementation

[0019] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0020] In the compounds described herein, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0021] In this specification, the halogens mentioned include fluorine, chlorine, bromine, and iodine.

[0022] 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.

[0023] For example, Can represent Can represent Can represent And so on.

[0024] In this specification, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the bonding of adjacent groups can be connected to another ring to form a spirostructure. See the example below:

[0025]

[0026] In this specification, the rings formed by the linkage can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0027] In this specification, "integers selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, "n1 is selected from 0 to 4" means that n1 is selected from 0, 1, 2, 3, or 4. And so on.

[0028] In this specification, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not substituted by a substituent. And so on.

[0029] In this specification, "CXX~CYY" in "substituted or unsubstituted CXX~CYY ZZ group" indicates the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, the number of carbon atoms in the substituent is not included. For example, "C6~C60" in "substituted or unsubstituted C6~C60 aryl group" indicates the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

[0030] In this specification, the term "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" include the following groups: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 fused polycyclic groups, substituted or unsubstituted C2-C30 heteroaryl groups, etc. Preferred groups include: deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornel, camphene, isocamphene, fentanyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The substituents include benzo[a]yl, fluoranyl, peryl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindyl, indyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, fluorenyl, benzofluorenyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoyl, benzocarbazoyl, indolocarbazoyl, indolo[3,2,1-JK]carbazoyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted, and two adjacent substituents can bond to form a ring.

[0031] In this specification, alkyl refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. Alkyl groups include straight-chain alkyl groups and branched-chain alkyl groups. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, etc. Chain alkyl groups containing three or more carbon atoms include their isomers; for example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on. The number of carbon atoms in the alkyl group is 1 to 20, preferably 1 to 15, and even more preferably 1 to 10.

[0032] In this specification, cycloalkyl refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. Cycloalkyl includes monocyclic, polycyclic, and bridged cycloalkyl groups. Examples of cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, camphene, etc. The cycloalkyl group has 3 to 20 carbon atoms, preferably 3 to 15, and more preferably 3 to 10.

[0033] In this specification, "silyl group" refers to -Si(R t )3 groups, wherein each R t The same or different groups are selected from the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, etc. Preferably, each R tThe same or different groups are selected from the following: hydrogen, deuterium, tritium, halogen, cyano, 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 cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted Substituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, etc., but not limited to these. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0034] In this specification, aryl refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, phenanthryl, anthraceneyl, triphenylene, pyrene, perylene, etc. Aryl, fluoranyl, fluorenyl, benzo[a]fluorenyl, spiroanthracene fluorenyl, etc., but not limited to these. The number of carbon atoms in the aryl group is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0035] In this specification, the fused polycyclic group refers to a monovalent group comprising at least two rings, wherein at least one aromatic ring and at least one non-aromatic ring are fused together. Examples of the fused polycyclic group may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc. The fused polycyclic group has 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12. The linkage site of the group may be on an aromatic ring or a non-aromatic ring, but is preferably on an aromatic ring.

[0036] In this specification, the term "heteroaryl" refers to a group obtained by replacing one or more carbon atoms of an aryl group with heteroatoms. These heteroatoms include, but are not limited to, atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, and silicon. The heteroaryl groups include monocyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, carbazoleyl, benzocarbazoleyl, spirofluoreneoxanthraceneyl, spirofluorenethionanthraceneyl, spirofluoreneazanthraceneyl, carbazolefuranyl, carbazolethiophenyl, carbazolefluorenyl, carbazoleoxanthraceneyl, indolocarbazoleyl, indolo[3,2,1-JK]carbazoleyl, etc. The heteroaryl group may have 2 to 30 carbon atoms, preferably 2 to 25, and more preferably 3 to 18.

[0037] In this specification, the term "arylene" refers to the collective term for divalent groups remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. The arylene includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene may include phenylene, biphenylene, terphenylene, tetraphenylene, pentaphenylene, naphthylene, phenanthrene, anthracene, triphenylene, pyrene, fluoranthracene, perylene, etc. The aryl group may contain, but is not limited to, fluoreneyl, benzo[a]fluoreneyl, spiroanthracene fluoreneyl, etc. The number of carbon atoms in the aryl group is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 10.

[0038] In this specification, the term "fused polycyclic aromatic hydrocarbon" refers to a divalent group comprising at least two rings, wherein at least one aromatic ring and at least one non-aromatic ring are fused together. Examples of such fused polycyclic aromatic hydrocarbons may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, etc. The number of carbon atoms in the fused polycyclic aromatic hydrocarbon is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0039] In this specification, the term "heteroaryl" refers to a divalent group in which at least one carbon atom is replaced by a heteroatom. The heteroatom is selected from, but is not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc. The heteroaryl includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl include pyridylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, benzothiopheneylene, dibenzothiopheneylene, benzodibenzothiopheneylene, indoleylene, carbazoylene, benzocarbazoylene, etc., but are not limited to these. The number of carbon atoms in the heteroaryl is 2 to 30, preferably 2 to 25, and more preferably 2 to 18.

[0040] This invention provides a nitrogen-containing compound, represented by the following formula 1,

[0041]

[0042] The Ar is selected from the following groups.

[0043]

[0044] The R1s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring.

[0045] The n1 is selected from integers from 0 to 4, and the n2 is selected from integers from 0 to 3;

[0046] The Xs that are the same or different are selected from CH or N, and at most one X is N;

[0047] The L is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups;

[0048] X1 and X2 are independently selected from single bonds, O, S, and C(R). x )2; The R x The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rx They bond with each other to form substituted or unsubstituted rings;

[0049] The rings A, B, and C are independently selected from one of the following: substituted or unsubstituted aromatic rings of C6 to C30, substituted or unsubstituted fused polycyclic aromatic rings of C6 to C30, or substituted or unsubstituted heteroaromatic rings of C2 to C30.

[0050] Preferably, the nitrogen-containing compound is selected from at least one of the following structures:

[0051]

[0052] The definitions of Ar, L, X1, X2, ring A, ring B, and ring C are the same as those in Equation 1.

[0053] Preferably, the Ar is selected from one of the following groups:

[0054]

[0055]

[0056] The R1s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring.

[0057] The n1 is selected from integers from 0 to 4, the n2 is selected from integers from 0 to 3, and the n3 is selected from integers from 0 to 2.

[0058] Preferably, R1 is the same or different from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted pyrene, substituted or unsubstituted Benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophene One of the following: substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R1 groups bonded together to form a substituted or unsubstituted ring.

[0059] Preferably, the L is selected from one or a combination of the following groups:

[0060]

[0061] The Y values ​​that are the same or different are selected from CH or N;

[0062] The R2s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle.

[0063] The m is selected from integers from 0 to 4, and the m1 is selected from integers from 0 to 3;

[0064] The a is selected from integers from 1 to 6;

[0065] X3 is selected from C(R) x3 )2, O, S or N(R) x3 ), the R x3 The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x3 They bond with each other to form substituted or unsubstituted rings.

[0066] Preferably, the L is selected from one or a combination of the following groups:

[0067]

[0068]

[0069] The R2s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle.

[0070] The m is selected from integers from 0 to 4, the m1 is selected from integers from 0 to 3, and the m2 is selected from integers from 0 to 2;

[0071] X3 is selected from C(R) x3 )2, O, S or N(R) x3 ), the R x3 The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x3 They bond with each other to form substituted or unsubstituted rings.

[0072] Preferably, the same or different R2s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctyl, substituted or Unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or Unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted 9-phenylcarbazoyl, substituted or unsubstituted One of 9-naphthylcarbazolyl, substituted or unsubstituted 9-biphenylcarbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolo[3,2,1-JK]carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R2s bonded together to form a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle;

[0073] The R x3The same or different from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted Benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or One of the following: unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, or substituted or unsubstituted quinoxalinyl group, or two adjacent R groups. x3 They bond with each other to form substituted or unsubstituted rings.

[0074] Preferably, at most two or at most one of R2 is a substituted or unsubstituted aromatic group (such as substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl). (e.g., benzo[fluorenyl], benzo[furanyl], dibenzo[furanyl], benzo[dibenzo[furanyl], benzo[thiophene], dibenzo[thiophene], benzo[dibenzo[thiophene], carbazole, 9-phenylcarbazole, 9-naphthylcarbazole, 9-biphenylcarbazole, benzo[carbazole], indolo[3,2,1-JK]carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl). More preferably, when R2 is a substituted or unsubstituted aromatic group, it is attached to the aromatic ring in L that is directly connected to Ar.

[0075] Preferably, ring A, ring B, and ring C are independently selected from one of the following ring structures.

[0076]

[0077] The Z that is the same or different is selected from C(R) z )2 or N, the R z The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R z They bond with each other to form substituted or unsubstituted aromatic or aliphatic hydrocarbon rings.

[0078] Preferably, ring A and ring C are independently selected from one of the ring structures shown below.

[0079]

[0080] The ring B is selected from one of the ring structures shown below.

[0081]

[0082] *, ·, and + indicate confluence sites;

[0083] f1 is selected from integers from 0 to 4, f2 is selected from integers from 0 to 6, f3 is selected from integers from 0 to 8, and f4 is selected from integers from 0 to 2.

[0084] The T values ​​that are the same or different are selected from CH or N;

[0085] The R3s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R3s bonded together to form a substituted or unsubstituted aromatic hydrocarbon ring or aliphatic hydrocarbon ring.

[0086] Preferably, in ring A, at most two or at most one T are selected from N; in ring B, at most two or at most one T are selected from N; and in ring C, at most two or at most one T are selected from N.

[0087] Preferably, the same or different R3s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted pyrene, substituted or unsubstituted substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted One of the following: substituted dibenzothiophene, substituted or unsubstituted benzodibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R3s bonded together to form a substituted or unsubstituted aromatic hydrocarbon ring or aliphatic hydrocarbon ring.

[0088] Preferably, the substituents in "substituted or unsubstituted" in R2 and R3 are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted Substituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted cyclooctyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted Substituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted Substituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted indolo[3,2,1-JK]carbazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group.

[0089] Preferably, the substituents in "substituted or unsubstituted" in R2 and R3 are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentyl Alkyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindyl, indyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, fluorenyl, benzofluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazolyl, indolo[3,2,1-JK]carbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0090] Preferably, the R xThe same or different from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, Substituted or unsubstituted cyclooctyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindenyl, Substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted One of the following: 9-phenylcarbazolyl, substituted or unsubstituted 9-naphthylcarbazolyl, substituted or unsubstituted 9-biphenylcarbazolyl, substituted or unsubstituted indolo[3,2,1-JK]carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl, or two adjacent R x They bond with each other to form substituted or unsubstituted rings: cyclopentane ring, cyclohexane ring, cycloheptane ring, adamantane ring, norbornene ring, fluorene ring.

[0091] Preferably, the nitrogen-containing compound of Formula 1 is selected from at least one of the following structures:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] The above lists some specific chemical structures of nitrogen compounds of Formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1 with substituents as defined above should be included.

[0127] In addition, the present invention also provides an organic electroluminescent device containing the nitrogen-containing compound of the present invention described above.

[0128] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer contains the nitrogen-containing compound of the present invention described above.

[0129] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer including a light-emitting layer containing the nitrogen-containing compound of the present invention described above.

[0130] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, which includes a host material and a dopant material. The host material contains the nitrogen-containing compound of the present invention described above.

[0131] Preferably, the organic electroluminescent device includes an anode, a cathode, and a capping layer located outside the anode or cathode, wherein the capping layer contains the nitrogen-containing compound of the present invention described above.

[0132] Preferably, the organic electroluminescent device includes an anode, a cathode, and a capping layer located outside the anode, wherein the capping layer contains the nitrogen-containing compound of the present invention described above.

[0133] Preferably, the organic electroluminescent device includes an anode, a cathode, and a capping layer located outside the cathode, wherein the capping layer contains the nitrogen-containing compound of the present invention described above.

[0134] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, charge generation layer, capping layer, nucleation inhibition layer, etc., but is not limited thereto. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, charge generation properties, light extraction properties, or metal deposition inhibition properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0135] 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:

[0136] In this specification, the anode serves to inject holes into the organic layer, and the anode material needs to have a high work function. The anode includes, but is not limited to, the materials described below: metals or their alloys, metal oxides, multilayer materials, etc. Specific examples may include aluminum (Al), silver (Ag), indium tin oxide (ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), zinc aluminum oxide (AZO), indium oxide (InO), etc., but are not limited to these. The film thickness of the anode is 1 nm to 1 μm, preferably 1 nm to 500 nm, and more preferably 1 nm to 400 nm.

[0137] In this specification, the cathode serves to inject electrons into the organic layer, and the cathode material needs to have a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include aluminum (Al), magnesium (Mg), silver (Ag), calcium (Ca), magnesium:silver (Mg:Ag), magnesium:ytterbium (Mg:Yb), lithium:aluminum (Li:Al), etc., but are not limited to these. The film thickness of the cathode is 1 nm to 800 nm, preferably 1 nm to 500 nm, more preferably 1 nm to 350 nm, and even more preferably 1 nm to 250 nm.

[0138] In this specification, the hole injection layer serves to lower the hole injection barrier between the anode and the organic layer, enabling effective hole injection into the organic layer. Hole injection materials include, but are not limited to, the following: metal oxides, phthalocyanine compounds, aromatic amine compounds, low-molecular-weight organic compounds containing polycyanates, and high-molecular-weight materials. Specific examples include molybdenum trioxide (MoO3), tungsten trioxide (WO3), copper phthalocyanine (CuPc), titanium phthalocyanine (TiOPC), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), and N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD). Materials used include, but are not limited to, 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. The hole injection layer thickness is 0.1 nm to 1 μm, preferably 1 nm to 800 nm, more preferably 1 nm to 500 nm, more preferably 1 nm to 250 nm, and even more preferably 1 nm to 200 nm.

[0139] In this specification, the hole transport layer is used to improve the hole transport efficiency in the device and to block electrons within the light-emitting layer. The hole transport layer includes, but is not limited to, the materials described below, such as aromatic amine derivatives, carbazole derivatives, and polymers. Specific examples may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 1,3,5-tris(9-carbazolyl)benzene (TCB), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), and poly(4-vinyltriphenylamine) (PVTPA). The hole transport layer film thickness is 1 nm to 1 μm, preferably 1 nm to 800 nm, more preferably 1 nm to 500 nm, and even more preferably 1 nm to 250 nm.

[0140] In this specification, the light-emitting layer may contain one or more materials, and may contain a host material and a dopant material. The doping ratio of the host material and the dopant material may vary depending on the materials used, typically the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, more preferably 1% to 10%. The thickness of the light-emitting layer is 1 nm to 500 nm, preferably 1 nm to 300 nm, more preferably 1 nm to 200 nm, and even more preferably 1 nm to 100 nm.

[0141] The host material can be one material or two or more materials. Host materials include, but are not limited to, the following: heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 9,10-di-2-naphthane (AND), 2-methyl-9,10-di(2-naphthyl)anthracene (MADN), 4,4-di(9-carbazole)biphenyl (CBP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), and 9,9'-(1,3-phenyl) 2,7-bis(carbazole-9-yl)-9,9-spirodifluorene (Spiro-2CBP), 1,3,5-tris(9-carbazole)phenyl (TCP), 3,3'-bis(dibenzothiophene-4-yl)-1,1'-biphenyl (m-BPDBT), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9Hcarbazole (CzSi), etc., but not limited thereto. Nitrogen-containing compounds of Formula 1 of the present invention are preferred.

[0142] The doping material may be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof, and the doping material includes, but is not limited to, the following materials: metal complexes, aromatic amine derivatives, styrene amine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples of doped materials may include bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (FIrPic), bis(2-phenylpyridyl)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridinium)iridium (Ir(ppy)3), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), tris[2-(p-tolyl)pyridinium-C2,N]iridium(III) (Ir(mppy)3), bis[9,9-dimethyl-2-(2-quinolinyl)-9H-fluoren-3-yl](2,4-pentanedione)iridium (Ir(flq)2(acac)), N 1 N 1 N 6 N 6 Tetraphenylpyrene-1,6-diamine, 2,5,8,11-tetra-tert-butylperylene (TBPe), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), coumarin 545T, 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), etc., but not limited to these.

[0143] In this specification, the hole blocking layer is used to block holes within the light-emitting layer, thereby increasing the binding rate of electrons and holes. The hole blocking layer material may include imidazole derivatives, phenanthroline derivatives, triazole derivatives, metal complexes, oxazole derivatives, triazine derivatives, etc., such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), etc., but is not limited to these. The hole blocking layer has a thickness of 0.01 nm to 500 nm, preferably 0.1 nm to 200 nm, more preferably 0.1 nm to 150 nm, and even more preferably 0.1 nm to 80 nm.

[0144] In this specification, the electron transport layer is used to improve the electron transport efficiency in the device and to block holes within the light-emitting layer. The electron transport layer includes, but is not limited to, the materials described below, such as metal complexes and heteroaromatic compounds. Specific examples may include, but are not limited to, aluminum 8-hydroxyquinoline (Alq3), aluminum tris(4-methyl-8-hydroxyquinoline) (Almq3), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,4,6-tris(3-(3-pyridyl)-(1,1'-biphenyl)-3-yl)-1,3,5-triazine (TmPPPyTz), etc., but are not limited to these. The electron transport layer has a thickness of 1 nm to 1 μm, preferably 1 nm to 800 nm, more preferably 1 nm to 500 nm, more preferably 1 nm to 250 nm, and even more preferably 1 nm to 150 nm.

[0145] In this specification, the electron injection layer serves to lower the electron injection barrier between the cathode and the organic layer, enabling electrons to be effectively injected into the organic layer. The electron injection layer material includes, but is not limited to, the materials listed below, such as metals, metal compounds, and metal oxides. Specific examples may include lithium (Li), ytterbium (Yb), lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), cesium fluoride (CsF), magnesium fluoride (MgF2), lithium oxide (Li2O), cesium carbonate (Cs2CO3), etc., but are not limited to these. The thickness of the electron injection layer is 0.01 nm to 200 nm, preferably 0.1 nm to 100 nm, more preferably 0.1 nm to 50 nm, and even more preferably 0.1 nm to 25 nm.

[0146] In this specification, the capping layer serves to couple light trapped within the device. The capping layer material includes, but is not limited to, the materials described below: metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include aluminum tris(8-hydroxyquinoline) (Alq3), N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), etc. Nitrogen-containing compounds of Formula 1 of the present invention are preferred.

[0147] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0148] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0149] Synthesis Examples

[0150] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. 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 this invention are of reagent purity.

[0151] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0152] There are no particular limitations on the preparation method of the nitrogen-containing compound of Formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The nitrogen-containing compound of Formula 1 of the present invention can be prepared, for example, by the synthetic route shown below.

[0153]

[0154] The Xn is a halogen, for example, the same or different Xn are selected from Cl, Br, I.

[0155] Synthesis Example 1:

[0156]

[0157] Preparation of intermediate A-26

[0158] Under nitrogen protection, a-26 (19.21 g, 60.00 mmol), pinacol diborate (15.39 g, 60.60 mmol), KOAc (11.78 g, 120.00 mmol), Pd(PPh3)4 (693 mg, 0.60 mmol), and 1,4-dioxane (400 ml) were added to a reaction flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / n-hexane at a ratio of 6:1 to give intermediate A-26 (17.19 g, yield 78%); HPLC purity ≥ 99.88%.

[0159] Preparation of intermediate B-26

[0160] Under nitrogen protection, A-26 (16.53 g, 45.00 mmol), b-26 (8.62 g, 45.00 mmol), K₂CO₃ (12.44 g, 90.00 mmol), Pd(dppf)Cl₂ (330 mg, 0.45 mmol), and 300 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by toluene / n-hexane in an 8:1 ratio to give intermediate B-6 (11.72 g, yield 74%); HPLC purity ≥ 99.90%.

[0161] Preparation of compound 26

[0162] Under nitrogen protection, B-26 (10.55 g, 30.00 mmol), C-26 (7.72 g, 30.00 mmol), sodium tert-butoxide (4.32 g, 45.00 mmol), Pd2(dba)3 (275 mg, 0.30 mmol), X-Phos (286 mg, 0.60 mmol), and toluene (200 ml) were added to a reaction flask and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 26 (13.06 g, 76% yield). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 572.1882 (theoretical value: 572.1889). Theoretical elemental content (%) C 42 H 24 N₂O: C, 88.09; H, 4.22; N, 4.89. Measured elemental content (%): C, 88.07; H, 4.20; N, 4.91.

[0163] Synthesis Example 2:

[0164]

[0165] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-48, and C-48, respectively, to obtain compound 48 (13.23 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 572.1881 (theoretical value: 572.1889). Theoretical elemental content (%) C 42 H 24 N₂O: C, 88.09; H, 4.22; N, 4.89. Measured elemental content (%): C, 88.06; H, 4.20; N, 4.87.

[0166] Synthesis Example 3:

[0167]

[0168] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-55 and C-48, respectively, to obtain compound 55 (16.31 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 724.2524 (theoretical value: 724.2515). Theoretical elemental content (%) C 54 H 32 N₂O: C, 89.48; H, 4.45; N, 3.86. Measured elemental content (%): C, 89.46; H, 4.47; N, 3.89.

[0169] Synthesis Example 4:

[0170]

[0171] Following the preparation method of compound 26 in Synthesis Example 1, C-26 was replaced with an equimolar amount of C-96 to obtain compound 96 (14.57 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 622.2056 (theoretical value: 622.2045). Theoretical elemental content (%) C 46 H 26 N₂O: C, 88.72; H, 4.21; N, 4.50. Measured elemental content (%): C, 88.75; H, 4.23; N, 4.47.

[0172] Synthesis Example 5:

[0173]

[0174] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-153 and C-48, respectively, to obtain compound 153 (12.98 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 576.2132 (theoretical value: 576.2140). Theoretical elemental content (%) C 42 H 20 D4N2O: C, 87.48; H, 4.89; N, 4.86. Measured elemental content (%): C, 87.46; H, 4.92; N, 4.89.

[0175] Synthesis Example 6:

[0176]

[0177] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-165 and C-48, respectively, to obtain compound 165 (13.02 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 586.2059 (theoretical value: 586.2045). Theoretical elemental content (%) C 43 H 26 N₂O: C, 88.03; H, 4.47; N, 4.77. Measured elemental content (%): C, 88.01; H, 4.50; N, 4.73.

[0178] Synthesis Example 7:

[0179]

[0180] Preparation of intermediate E-200

[0181] Under nitrogen protection, e-200 (44.43 g, 140.00 mmol), A-26 (51.93 g, 141.4 mmol), Na₂CO₃ (22.26 g, 210.00 mmol), Pd(PPh₃)₄ (809 mg, 0.7 mmol), and 800 mL of tetrahydrofuran / water (3:1) were added to a reaction flask, and the mixture was stirred under reflux for 6.5 hours. 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 (7:1) to give intermediate E-200 (42.21 g, 70% yield); HPLC purity ≥ 99.84%.

[0182] Preparation of intermediate F-200

[0183] Under nitrogen protection, E-200 (38.77 g, 90.00 mmol), f-200 (24.86 g, 90.00 mmol), K₂CO₃ (18.66 g, 135.00 mmol), Pd(dppf)Cl₂ (658 mg, 0.9 mmol), and 500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 6 hours. 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 at a ratio of 5:1 to give intermediate F-200 (32.41 g, yield 72%); HPLC purity ≥ 99.92%.

[0184] Preparation of compound 200

[0185] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of F-200, b-48, and C-48, respectively, to obtain compound 200 (17.93 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 796.2901 (theoretical value: 796.2910). Theoretical elemental content (%) C 57 H 40 N₂OSi: C, 85.90; H, 5.06; N, 3.51. Measured elemental content (%): C, 85.88; H, 5.09; N, 3.48.

[0186] Synthesis Example 8:

[0187]

[0188] Preparation of intermediate F-218

[0189] According to the preparation method of intermediate F-200 in Synthesis Example 7, e-200, A-26, and f-200 were replaced with equimolar amounts of e-218, A-48, and f-218, respectively, to obtain intermediate F-218 (31.80 g, yield 73%), and the solid purity was determined by HPLC to be ≥99.93%.

[0190] Preparation of compound 200

[0191] Following the preparation method of compound 26 in Synthesis Example 1, B-26 and C-26 were replaced with equimolar amounts of F-218 and C-218, respectively, to obtain compound 218 (16.07 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 704.2840 (theoretical value: 704.2828). Theoretical elemental content (%) C 52 H 36N₂O: C, 88.61; H, 5.15; N, 3.97. Measured elemental content (%): C, 88.64; H, 5.12; N, 4.00.

[0192] Synthesis Example 9:

[0193]

[0194] Following the preparation method of compound 218 in Synthesis Example 8, e-218, A-48, f-218, and C-218 were replaced with equimolar amounts of e-227, A-26, f-227, and C-48, respectively, to obtain compound 227 (14.96 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 673.2166 (theoretical value: 673.2154). Theoretical elemental content (%) C 49 H 27 N3O: C, 87.35; H, 4.04; N, 6.24. Measured elemental content (%): C, 87.38; H, 4.02; N, 6.22.

[0195] Synthesis Example 10:

[0196]

[0197] Following the preparation method of compound 218 in Synthesis Example 8, e-218, A-48, f-218, and C-210 were replaced with equimolar amounts of e-227, A-26, A-26, and C-48, respectively, to obtain compound 278 (19.00 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 811.2638 (theoretical value: 811.2624). Theoretical elemental content (%) C 60 H 33 N3O: C, 88.76; H, 4.10; N, 5.18. Measured elemental content (%): C, 88.79; H, 4.12; N, 5.14.

[0198] Synthesis Example 11:

[0199]

[0200] Following the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-210 were replaced with equimolar amounts of e-326, A-26, and C-48, respectively, to obtain compound 326 (18.34 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 814.2802 (theoretical value: 814.2812). Theoretical elemental content (%) C 60 H 30D3N3O: C, 88.43; H, 4.45; N, 5.16. Measured elemental content (%): C, 88.40; H, 4.47; N, 5.14.

[0201] Synthesis Example 12:

[0202]

[0203] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-48, and C-333, respectively, to obtain compound 333 (13.08 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 573.1852 (theoretical value: 573.1841). Theoretical elemental content (%) C 41 H 23 N3O: C, 85.84; H, 4.04; N, 7.33. Measured elemental content (%): C, 85.82; H, 4.02; N, 7.35.

[0204] Synthesis Example 13:

[0205]

[0206] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-347, respectively, to obtain compound 347 (13.25 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 588.1668 (theoretical value: 588.1660). Theoretical elemental content (%) C 42 H 24 N₂S: C, 85.69; H, 4.11; N, 4.76. Measured elemental content (%): C, 85.66; H, 4.14; N, 4.72.

[0207] Synthesis Example 14:

[0208]

[0209] Following the preparation method of compound 26 in Synthesis Example 1, a-26 and C-26 were replaced with equimolar amounts of a-48 and C-347, respectively, to obtain compound 352 (13.61 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 588.1669 (theoretical value: 588.1660). Theoretical elemental content (%) C 42 H 24 N2S: C, 85.69; H, 4.11; N, 4.76. Measured elemental content (%): C, 85.67; H, 4.13; N, 4.73.

[0210] Synthesis Example 15:

[0211]

[0212] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-356 and C-347, respectively, to obtain compound 356 (13.42 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 588.1671 (theoretical value: 588.1660). Theoretical elemental content (%) C 42 H 24 N2S: C, 85.69; H, 4.11; N, 4.76. Measured elemental content (%): C, 85.70; H, 4.09; N, 4.78.

[0213] Synthesis Example 16:

[0214]

[0215] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-359 and C-347, respectively, to obtain compound 359 (14.96 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 664.1981 (theoretical value: 664.1973). Theoretical elemental content (%) C 48 H 28 N₂S: C, 86.72; H, 4.25; N, 4.21. Measured elemental content (%): C, 86.70; H, 4.28; N, 4.18.

[0216] Synthesis Example 17:

[0217]

[0218] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-369, b-369, and C-347, respectively, to obtain compound 369 (14.76 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 664.1983 (theoretical value: 664.1973). Theoretical elemental content (%) C 48 H 28 N₂S: C, 86.72; H, 4.25; N, 4.21. Measured elemental content (%): C, 86.74; H, 4.23; N, 4.23.

[0219] Synthesis Example 18:

[0220]

[0221] Following the preparation method of compound 26 in Synthesis Example 1, a-26 and C-26 were replaced with equimolar amounts of a-48 and C-388, respectively, to obtain compound 388 (13.60 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 588.1670 (theoretical value: 588.1660). Theoretical elemental content (%) C 42 H 24 N2S: C, 85.69; H, 4.11; N, 4.76. Measured elemental content (%): C, 85.67; H, 4.13; N, 4.74.

[0222] Synthesis Example 19:

[0223]

[0224] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-449, and C-449, respectively, to obtain compound 449 (14.95 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 638.1830 (theoretical value: 638.1817). Theoretical elemental content (%) C 46 H 26 N2S: C, 86.49; H, 4.10; N, 4.39. Measured elemental content (%): C, 86.51; H, 4.12; N, 4.37.

[0225] Synthesis Example 20:

[0226]

[0227] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-359 and C-347, respectively, to obtain compound 452 (13.09 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 589.1600 (theoretical value: 589.1613). Theoretical elemental content (%) C 41 H 23 N3S: C, 83.51; H, 3.93; N, 7.13. Measured elemental content (%): C, 83.53; H, 3.90; N, 7.10.

[0228] Synthesis Example 21:

[0229]

[0230] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-494, respectively, to obtain compound 494 (14.56 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 638.1807 (theoretical value: 638.1817). Theoretical elemental content (%) C 46 H 26 N₂S: C, 86.49; H, 4.10; N, 4.39. Measured elemental content (%): C, 86.52; H, 4.13; N, 4.37.

[0231] Synthesis Example 22:

[0232]

[0233] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-153, and C-347, respectively, to obtain compound 556 (13.87 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 592.1920 (theoretical value: 592.1911). Theoretical elemental content (%) C 42 H 20 D4N2S: C, 85.11; H, 4.76; N, 4.73. Measured elemental content (%): C, 85.13; H, 4.73; N, 4.76.

[0234] Synthesis Example 23:

[0235]

[0236] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-48, and C-559, respectively, to obtain compound 559 (13.47 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 598.2296 (theoretical value: 598.2288). Theoretical elemental content (%) C 42 H 14 D 10 N2S: C, 84.25; H, 5.72; N, 4.68. Measured elemental content (%): C, 84.23; H, 5.75; N, 4.65.

[0237] Synthesis Example 24:

[0238]

[0239] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-560, b-48, and C-347, respectively, to obtain compound 560 (14.01 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 598.2395 (theoretical value: 598.2288). Theoretical elemental content (%) C 42 H 14 D 10 N2S: C, 84.25; H, 5.72; N, 4.68. Measured elemental content (%): C, 84.22; H, 5.73; N, 4.66.

[0240] Synthesis Example 25:

[0241]

[0242] Following the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-218 were replaced with equimolar amounts of e-200, f-606, and C-347, respectively, to obtain compound 606 (14.76 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 664.1960 (theoretical value: 664.1973). Theoretical elemental content (%) C 48 H 28 N2S: C, 86.72; H, 4.25; N, 4.21. Measured elemental content (%): C, 86.70; H, 4.27; N, 4.23.

[0243] Synthesis Example 26:

[0244]

[0245] Following the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-218 were replaced with equimolar amounts of e-227, f-200, and C-347, respectively, to obtain compound 628 (16.8 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 736.2380 (theoretical value: 736.2368). Theoretical elemental content (%) C 51 H 36 N₂SSi: C, 83.11; H, 4.92; N, 3.80. Measured elemental content (%): C, 83.13; H, 4.90; N, 3.83.

[0246] Synthesis Example 27:

[0247]

[0248] Following the preparation method of compound 218 in Synthesis Example 8, f-218 and C-218 were replaced with equimolar amounts of f-657 and C-347, respectively, to obtain compound 628 (20.50 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 922.2851 (theoretical value: 922.2838). Theoretical elemental content (%) C 66 H 42 N₂SSi: C, 85.87; H, 4.59; N, 3.03. Measured elemental content (%): C, 85.85; H, 4.61; N, 3.00.

[0249] Synthesis Example 28:

[0250]

[0251] Following the preparation method of compound 218 in Synthesis Example 8, f-218 and C-218 were replaced with equimolar amounts of f-696 and C-696, respectively, to obtain compound 696 (17.98 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 798.3060 (theoretical value: 798.3069). Theoretical elemental content (%) C 58 H 42 N2S: C, 87.18; H, 5.30; N, 3.51. Measured elemental content (%): C, 87.16; H, 5.33; N, 3.53.

[0252] Synthesis Example 29:

[0253]

[0254] Following the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-218 were replaced with equimolar amounts of e-227, f-725, and C-725, respectively, to obtain compound 725 (15.65 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 704.2298 (theoretical value: 704.2286). Theoretical elemental content (%) C 51 H 32 N2S: C, 86.90; H, 4.58; N, 3.97. Measured elemental content (%): C, 86.92; H, 4.54; N, 3.95.

[0255] Synthesis Example 30:

[0256]

[0257] Following the preparation method of compound 200 in Synthesis Example 7, A-26, f-200, and C-48 were replaced with equimolar amounts of A-48, f-734, and C-347, respectively, to obtain compound 734 (17.80 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 790.2435 (theoretical value: 790.2443). Theoretical elemental content (%) C 58 H 34 N2S: C, 88.07; H, 4.33; N, 3.54. Measured elemental content (%): C, 88.04; H, 4.35; N, 3.51.

[0258] Synthesis Example 31:

[0259]

[0260] Following the preparation method of compound 218 in Synthesis Example 8, f-218 and C-218 were replaced with equimolar amounts of f-742 and C-347, respectively, to obtain compound 742 (18.04 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 780.2589 (theoretical value: 780.2599). Theoretical elemental content (%) C 57 H 36 N2S: C, 87.66; H, 4.65; N, 3.59. Measured elemental content (%): C, 87.68; H, 4.67; N, 3.56.

[0261] Synthesis Example 32:

[0262]

[0263] Following the preparation method of compound 200 in Synthesis Example 7, A-26, f-200, and C-200 were replaced with equimolar amounts of A-48, f-756, and C-756, respectively, to obtain compound 756 (18.95 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 830.2380 (theoretical value: 830.2392). Theoretical elemental content (%) C 60 H 34 N₂OS: C, 86.72; H, 4.12; N, 3.37. Measured elemental content (%): C, 86.70; H, 4.15; N, 3.35.

[0264] Synthesis Example 33:

[0265]

[0266] Following the preparation method of compound 218 in Synthesis Example 8, A-48, f-218, and C-218 were replaced with equimolar amounts of A-26, A-26, and C-347, respectively, to obtain compound 767 (19.38 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 827.2385 (theoretical value: 827.2395). Theoretical elemental content (%) C 60 H 33 N3S: C, 87.04; H, 4.02; N, 5.07. Measured elemental content (%): C, 87.02; H, 4.00; N, 5.10.

[0267] Synthesis Example 34:

[0268]

[0269] Following the preparation method of compound 218 in Synthesis Example 8, e-218, A-48, f-218, and C-218 were replaced with equimolar amounts of e-227, A-26, f-813, and C-347, respectively, to obtain compound 813 (15.07 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 669.2275 (theoretical value: 669.2287). Theoretical elemental content (%) C 48 H 23 D5N2S: C, 86.07; H, 4.96; N, 4.18. Measured elemental content (%): C, 86.09; H, 4.99; N, 4.15.

[0270] Synthesis Example 35:

[0271]

[0272] Following the preparation method of compound 200 in Synthesis Example 7, f-200, b-200, and C-200 were replaced with equimolar amounts of f-606, b-153, and C-347, respectively, to obtain compound 822 (17.21 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 744.2548 (theoretical value: 744.2537). Theoretical elemental content (%) C 54 H 28 D4N2S: C, 87.07; H, 4.87; N, 3.76. Measured elemental content (%): C, 87.04; H, 4.84; N, 3.79.

[0273] Synthesis Example 36:

[0274]

[0275] Following the preparation method of compound 200 in Synthesis Example 7, e-200, A-26, and C-200 were replaced with equimolar amounts of e-854, A-48, and C-347, respectively, to obtain compound 854 (18.56 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 813.2625 (theoretical value: 813.2634). Theoretical elemental content (%) C 56 H 39 N3SSi: C, 82.62; H, 4.83; N, 5.16. Measured elemental content (%): C, 82.60; H, 4.80; N, 5.18.

[0276] Synthesis Example 37:

[0277]

[0278] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-895, respectively, to obtain compound 895 (13.8 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 589.1626 (theoretical value: 589.1613). Theoretical elemental content (%) C 41 H 23 N3S: C, 83.51; H, 3.93; N, 7.13. Measured elemental content (%): C, 83.53; H, 3.90; N, 7.10.

[0279] Synthesis Example 38:

[0280]

[0281] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-48, and C-906, respectively, to obtain compound 906 (13.47 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 598.2401 (theoretical value: 598.2409). Theoretical elemental content (%) C 45 H 30 N2: C, 90.27; H, 5.05; N, 4.68. Measured elemental content (%): C, 90.29; H, 5.03; N, 4.65.

[0282] Synthesis Example 39:

[0283]

[0284] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-48, b-48, and C-942, respectively, to obtain compound 942 (16.70 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 722.2734 (theoretical value: 722.2722). Theoretical elemental content (%) C 55 H 34 N2: C, 91.38; H, 4.74; N, 3.88. Measured elemental content (%): C, 91.36; H, 4.70; N, 3.90.

[0285] Synthesis Example 40:

[0286]

[0287] Following the preparation method of compound 26 in Synthesis Example 1, C-26 was replaced with an equimolar amount of C-959 to obtain compound 959 (16.00 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 720.2554 (theoretical value: 720.2565). Theoretical elemental content (%) C 55 H 32 N2: C, 91.64; H, 4.47; N, 3.89. Measured elemental content (%): C, 91.60; H, 4.50; N, 3.92.

[0288] Synthesis Example 41:

[0289]

[0290] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-962 to obtain compound 962 (14.62 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 624.2553 (theoretical value: 624.2565). Theoretical elemental content (%) C 47 H 32 N2: C, 90.35; H, 5.16; N, 4.48. Measured elemental content (%): C, 90.38; H, 5.14; N, 4.50.

[0291] Synthesis Example 42:

[0292]

[0293] Following the preparation method of compound 26 in Synthesis Example 1, a-26 and C-26 were replaced with equimolar amounts of a-48 and C-964 to obtain compound 964 (15.75 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 690.3046 (theoretical value: 690.3035). Theoretical elemental content (%) C 52 H 38 N2: C, 90.40; H, 5.54; N, 4.05. Measured elemental content (%): C, 90.42; H, 5.52; N, 4.07.

[0294] Synthesis Example 43:

[0295]

[0296] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-981 to obtain compound 981 (14.40 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 648.2574 (theoretical value: 648.2565). Theoretical elemental content (%) C 49 H 32 N2: C, 90.71; H, 4.97; N, 4.32. Measured elemental content (%): C, 90.73; H, 4.99; N, 4.30.

[0297] Synthesis Example 44:

[0298]

[0299] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-1058 and C-906 to obtain compound 1058 (13.52 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 600.2325 (theoretical value: 600.2314). Theoretical elemental content (%) C 43 H 28 N4: C, 85.97; H, 4.70; N, 9.33. Measured elemental content (%): C, 85.99; H, 4.74; N, 9.31.

[0300] Synthesis Example 45:

[0301]

[0302] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-1065 and C-906 to obtain compound 1065 (15.89 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 678.2987 (theoretical value: 678.2973). Theoretical elemental content (%) C 51 H 30 D4N2: C, 90.23; H, 5.64; N, 4.13. Measured elemental content (%): C, 90.20; H, 5.60; N, 4.17.

[0303] Synthesis Example 46:

[0304]

[0305] Following the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-218 were replaced with equimolar amounts of e-200, f-1133, and C-906, respectively, to obtain compound 1133 (15.80 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 692.2640 (theoretical value: 692.2628). Theoretical elemental content (%) C 51 H 33 FN2: C, 88.41; H, 4.80; N, 4.04. Measured elemental content (%): C, 88.43; H, 4.83; N, 4.01.

[0306] Synthesis Example 47:

[0307]

[0308] Following the preparation method of compound 218 in Synthesis Example 8, e-218, A-48, f-218, and C-218 were replaced with equimolar amounts of e-227, A-26, f-1169, and C-906, respectively, to obtain compound 1169 (18.40 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 839.3311 (theoretical value: 839.3300). Theoretical elemental content (%) C 63 H 41 N3: C, 90.08; H, 4.92; N, 5.00. Measured elemental content (%): C, 90.10; H, 4.90; N, 5.04.

[0309] Synthesis Example 48:

[0310]

[0311] Following the preparation method of compound 218 in Synthesis Example 8, e-218, A-48, f-218, and C-218 were replaced with equimolar amounts of e-200, A-26, f-1170, and C-906, respectively, to obtain compound 1170 (15.41 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 675.2660 (theoretical value: 675.2674). Theoretical elemental content (%) C 50 H 33 N3: C, 88.86; H, 4.92; N, 6.22. Measured elemental content (%): C, 88.88; H, 4.94; N, 6.20.

[0312] Synthesis Example 49:

[0313]

[0314] According to the preparation method of compound 218 in Synthesis Example 8, e-218, f-218, and C-218 were replaced with equimolar amounts of e-1228, A-48, and C-906, respectively, to obtain compound 1228 (19.68 g). HPLC analysis showed that the solid purity was ≥99.98%. Mass spectrometry m / z: 851.3308 (theoretical value: 851.3300). Theoretical elemental content (%) C 64 H 41 N3: C, 90.22; H, 4.85; N, 4.93. Measured elemental content (%): C, 90.20; H, 4.87; N, 4.95.

[0315] Synthesis Example 50:

[0316]

[0317] Following the preparation method of compound 26 in Synthesis Example 1, a-26, b-26, and C-26 were replaced with equimolar amounts of a-1243, b-48, and C-48 to obtain compound 1243 (14.76 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 622.2056 (theoretical value: 622.2045). Theoretical elemental content (%) C 46 H 26 N₂O: C, 88.72; H, 4.21; N, 4.50. Measured elemental content (%): C, 88.70; H, 4.23; N, 4.53.

[0318] Synthesis Example 51:

[0319]

[0320] Following the preparation method of compound 26 in Synthesis Example 1, a-26 and C-26 were replaced with equimolar amounts of a-1260 and C-906 to obtain compound 1260 (13.85 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 599.2351 (theoretical value: 599.2361). Theoretical elemental content (%) C 44 H 29 N3: C, 88.12; H, 4.87; N, 7.01. Measured elemental content (%): C, 88.10; H, 4.90; N, 7.03.

[0321] Synthesis Example 52:

[0322]

[0323] Preparation of intermediate C-1267

[0324] Under nitrogen protection, C1-1267 (15.39 g, 50.00 mmol), f-200 (13.95 g, 50.5 mmol), K2CO3 (10.37 g, 75.00 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), and 350 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at a ratio of 5:1 to give intermediate C-1267 (15.60 g, yield 74%); HPLC purity ≥ 99.86%.

[0325] Preparation of compound 1267

[0326] Following the preparation method of compound 26 in Synthesis Example 1, b-26 and C-26 were replaced with equimolar amounts of b-48 and C-1267 to obtain compound 1267 (16.58 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 736.2380 (theoretical value: 736.2368). Theoretical elemental content (%) C 51 H 36 N₂SSi: C, 83.11; H, 4.92; N, 3.80. Measured elemental content (%): C, 83.13; H, 4.90; N, 3.84.

[0327] Synthesis Example 53:

[0328]

[0329] Following the preparation method of compound 1267 in Synthesis Example 52, C1-1267, f-200, a-26, b-26, and C-26 were replaced with equimolar amounts of C1-1303, f-696, a-48, b-48, and C-1303 to obtain compound 1303 (17.85 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 782.3288 (theoretical value: 782.3297). Theoretical elemental content (%) C 58 H 42 N₂O: C, 88.97; H, 5.41; N, 3.58. Measured elemental content (%): C, 88.95; H, 5.43; N, 3.55.

[0330] Synthesis Example 54:

[0331]

[0332] Following the preparation method of compound 1267 in Synthesis Example 52, C1-1267, f-200, a-26, and C-26 were replaced with equimolar amounts of C1-1322, f-725, a-48, and C-1322 to obtain compound 1322 (16.73 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 714.3024 (theoretical value: 714.3035). Theoretical elemental content (%) C 54 H 38 N2: C, 90.72; H, 5.36; N, 3.92. Measured elemental content (%): C, 90.70; H, 5.34; N, 3.95.

[0333] Device Examples

[0334] In this invention, the ITO substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0335] 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, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0336] Example 1: Fabrication of Organic Electroluminescent Device 1

[0337] A hole injection layer with a thickness of 10 nm was vacuum-deposited on the ITO anode using a mixture of HT-1:HI-1 = 97:3 (wt%). HT-1 was then vacuum-deposited on the hole injection layer as a first hole transport layer with a thickness of 70 nm. HT-2 was then vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 10 nm. Compound 26:TADF-1 of the present invention with a thickness of 75:25 (wt%) was then vacuum-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 30 nm. ET-1:Liq with a thickness of 1:1 (wt%) was then vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm. Liq was then vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Al was then vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0338] Examples 2-25: Fabrication of Organic Electroluminescent Devices 2-25

[0339] Replacing compound 26 in the luminescent layer of Example 1 with compounds 48, 96, 153, 165, 200, 218, 227, 278, 333, 356, 359, 388, 449, 560, 606, 657, 725, 734, 742, 822, 854, 942, 1065, and 1169 respectively, while keeping other steps the same, organic electroluminescent devices 2-25 are obtained.

[0340] Comparative Examples 1-3: Fabrication of Comparative Organic Electroluminescent Devices 1-3

[0341] By replacing compound 26 in the light-emitting layer of Example 1 with R-1, R-2, and R-3 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 3 were obtained.

[0342]

[0343] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1-25 and Comparative Examples 1-3 of this invention are shown in Table 1.

[0344] Table 1

[0345]

[0346]

[0347] As can be seen from Table 1, when the nitrogen-containing compound of Formula 1 of the present invention is used as the light-emitting host material in organic electroluminescent devices, the performance of the devices is significantly improved, specifically in terms of higher luminous efficiency and longer service life.

[0348] Example 26: Fabrication of Organic Electroluminescent Device 26

[0349] A hole injection layer with a thickness of 10 nm was vacuum-deposited on the ITO anode using a mixture of HT-3:HI-1 = 97:3 (wt%). HT-3 was then vacuum-deposited on the hole injection layer as a first hole transport layer with a thickness of 70 nm. HT-4 was then vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 10 nm. Compound 26 of the present invention, TADF-2:GD-1 = 74.4:25:0.6 (wt%), was then vacuum-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 30 nm. ET-2:Liq = 1:1 (wt%) was then vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm. Liq was then vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Al was then vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0350] Examples 27-50: Fabrication of Organic Electroluminescent Devices 27-50

[0351] In Example 26, compound 26 in the light-emitting layer was replaced with compounds 48, 153, 326, 347, 352, 356, 359, 369, 388, 452, 494, 556, 559, 560, 628, 696, 756, 767, 813, 895, 906, 959, 964, and 1128, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 27-50.

[0352] Comparative Examples 4-6: Fabrication of Comparative Organic Electroluminescent Devices 4-6

[0353] By replacing compound 26 in the light-emitting layer of Example 26 with R-1, R-4, and R-5 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 4-6 were obtained.

[0354]

[0355] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 26-50 and Comparative Examples 4-6 of this invention are shown in Table 2.

[0356] Table 2

[0357]

[0358]

[0359] As can be seen from Table 2, when the nitrogen-containing compound of Formula 1 of the present invention is used as the light-emitting host material in organic electroluminescent devices, the performance of the devices is significantly improved, specifically in terms of higher luminous efficiency and longer service life.

[0360] Example 51: Fabrication of Organic Electroluminescent Device 51

[0361] A hole injection layer with a thickness of 10 nm was vacuum-deposited on the ITO anode using a mixture of HT-5:HI-1 = 97:3 (wt%). HT-5 was then vacuum-deposited on the hole injection layer as a first hole transport layer with a thickness of 65 nm. HT-6 was then vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 15 nm. Compound 26:RH-1:Ir(piq)2(acac) = 47:47:6 (wt%) of the present invention was then vacuum-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 35 nm. ET-2:Liq = 1:1 (wt%) was then vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm. Liq was then vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Al was then vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0362] Examples 52-75: Fabrication of Organic Electroluminescent Devices 52-75

[0363] In Example 51, compound 26 in the luminescent layer was replaced with compounds 48, 55, 153, 200, 347, 352, 356, 359, 369, 388, 556, 734, 822, 962, 981, 1058, 1065, 1133, 1170, 1243, 1260, 1276, 1303, and 1322, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 52-75.

[0364] Comparative Examples 7-9: Fabrication of Comparative Organic Electroluminescent Devices 7-9

[0365] By replacing compound 26 in the luminescent layer of Example 51 with R-1, R-6, and R-7 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 7-9 were obtained.

[0366]

[0367] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 51-75 and Comparative Examples 7-9 of this invention are shown in Table 3.

[0368] Table 3

[0369]

[0370]

[0371] As can be seen from Table 3, when the nitrogen-containing compound of Formula 1 of this invention is used as the light-emitting host material in organic electroluminescent devices, the performance of the devices is significantly improved, specifically in terms of higher luminous efficiency and longer service life.

[0372] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A nitrogen-containing compound, characterized in that, It is represented by the following equation 1, The Ar is selected from the following groups. The R1s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring. The n1 is selected from integers from 0 to 4, and the n2 is selected from integers from 0 to 3; The Xs that are the same or different are selected from CH or N, and at most one X is N; The L is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups; X1 and X2 are independently selected from single bonds, O, S, and C(R). x )2; The R x The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x They bond together to form substituted or unsubstituted rings; The rings A, B, and C are independently selected from one of the following: substituted or unsubstituted aromatic rings of C6 to C30, substituted or unsubstituted fused polycyclic aromatic rings of C6 to C30, or substituted or unsubstituted heteroaromatic rings of C2 to C30.

2. The nitrogen-containing compound according to claim 1, characterized in that, The Ar is selected from one of the following groups. The R1s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring. The n1 is selected from integers from 0 to 4, the n2 is selected from integers from 0 to 3, and the n3 is selected from integers from 0 to 2.

3. The nitrogen-containing compound according to claim 1, characterized in that, The L is selected from one or a combination of the following groups. The Y values ​​that are the same or different are selected from CH or N; The R2s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle. The m is selected from integers from 0 to 4, and the m1 is selected from integers from 0 to 3; The a is selected from integers from 1 to 6; X3 is selected from C(R) x3 )2, O, S or N(R) x3 ), the R x3 The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x3 They bond with each other to form substituted or unsubstituted rings.

4. The nitrogen-containing compound according to claim 1, characterized in that, The L is selected from one or a combination of the following groups. The R2s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle. The m is selected from integers from 0 to 4, the m1 is selected from integers from 0 to 3, and the m2 is selected from integers from 0 to 2; X3 is selected from C(R) x3 )2, O, S or N(R) x3 ), the R x3 The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x3 They bond with each other to form substituted or unsubstituted rings.

5. The nitrogen-containing compound according to claim 1, characterized in that, Ring A, ring B, and ring C are independently selected from one of the ring structures shown below. The Z that is the same or different is selected from C(R) z )2 or N, the R z The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R z They bond with each other to form substituted or unsubstituted aromatic or aliphatic hydrocarbon rings.

6. The nitrogen-containing compound according to claim 1, characterized in that, Ring A and ring C are independently selected from one of the ring structures shown below. The ring B is selected from one of the ring structures shown below. *, ·, and + indicate confluence sites; f1 is selected from integers from 0 to 4, f2 is selected from integers from 0 to 6, f3 is selected from integers from 0 to 8, and f4 is selected from integers from 0 to 2. The T values ​​that are the same or different are selected from CH or N; The R3s, whether identical or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R3s bonded together to form a substituted or unsubstituted aromatic hydrocarbon ring or aliphatic hydrocarbon ring.

7. The nitrogen-containing compound according to claim 1, characterized in that, The nitrogen-containing compound of Formula 1 is selected from at least one of the structures shown below.

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device contains the nitrogen-containing compound as described in any one of claims 1 to 7.

9. The electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer contains a nitrogen-containing compound as described in any one of claims 1 to 7.

10. The electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and a capping layer located outside the anode or cathode, wherein the capping layer contains a nitrogen-containing compound as described in any one of claims 1 to 7.

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