Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention relates to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof, relates to the field of organic electroluminescence, and aims to solve the problems that the existing electron transport materials are generally low in electron mobility, so that carrier transport is unbalanced, and the luminous efficiency and the service life of the organic electroluminescent device are directly influenced. Therefore, the invention provides the nitrogen-containing heterocyclic compound with relatively high electron mobility, proper energy level and relatively high glass transition temperature, so that the carrier transmission is balanced, the exciton recombination rate is effectively improved, the film forming quality is improved, the efficiency of the organic light-emitting device is enhanced, and the service life of the organic light-emitting device is prolonged.

Description

Technical Field

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

[0002] Among emerging display technologies, organic light-emitting diodes (OLEDs) have become one of the mainstream directions due to their outstanding advantages such as self-illumination, wide viewing angle, and the ability to achieve flexible displays. As the market continues to evolve towards ultra-high definition, large size, and foldable forms, higher demands are being placed on the efficiency, lifespan, and power consumption of OLED devices. As key functional layers for regulating carrier injection, transport, and recombination, the material properties of the electron transport layer and hole blocking layer directly affect the industrialization process of the devices.

[0003] The electron transport layer primarily undertakes the task of transporting electrons from the cathode to the light-emitting layer, requiring suitable energy level matching, high electron mobility, and good stability. However, currently widely used electron transport materials generally suffer from low electron mobility and a mismatch with hole mobility, easily causing carrier recombination region shift and efficiency decline. Simultaneously, some materials lack stability under long-term operation or environmental stress, exhibiting a tendency to crystallize or degrade, affecting device lifetime and reliability. The hole blocking layer, located between the light-emitting layer and the electron transport layer, prevents holes from further diffusing into the electron transport layer, promoting efficient recombination of electrons and holes within the light-emitting layer. Ideal materials should possess a high hole blocking energy barrier, a low electron injection barrier, and excellent film-forming properties and interfacial compatibility. Existing hole blocking materials often face problems in practical applications such as unsatisfactory energy level matching, excessively high electron injection barriers, or unstable film morphology, leading to increased device driving voltage and exacerbated efficiency roll-off, thus limiting overall performance improvement.

[0004] Developing electron transport layer and hole blocking layer materials with high electron mobility, excellent stability and good energy level matching is of great significance for achieving carrier balance and improving the efficiency and lifetime of OLED devices. Summary of the Invention

[0005] To address the problems existing in the prior art, the present invention provides a nitrogen-containing heterocyclic compound and its organic electroluminescent device, which can improve luminous efficiency and extend the life of the device.

[0006] Specifically, the structure of the nitrogen-containing heterocyclic compound is shown in Formula 1 or Formula 2: ; X1 and X2 are independently selected from C(R0) or N; R0 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring. Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups. The L1, L2, L3, and L4 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene ring fused cycloyl group. A is independently selected from formula a-1 or formula a-2; The R2 is independently selected from one or a combination of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring; The n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19; The L5 is independently selected from one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings in a fused cycloyl group, or substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene rings in a fused cycloyl group. The Ra is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent Ra can be bonded to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, or 3; The L6 and L7 are independently selected from single bonds or one or a combination of the following groups; ; The R1 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R1s can be bonded to form a substituted or unsubstituted ring. The value of m is independently selected from 0, 1, 2, 3 or 4.

[0007] An organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or more of the nitrogen-containing heterocyclic compounds described in this invention.

[0008] Beneficial effects

[0009] The nitrogen-containing heterocyclic compound described in this application exhibits high electron mobility and a suitable energy level match between LUMO and HOMO, which can significantly improve electron transport efficiency. Its high hole blocking barrier effectively confines holes within the emissive layer, optimizing the carrier recombination region and thus significantly improving device luminescence efficiency. Simultaneously, this material possesses a high glass transition temperature, maintaining a stable film state during device operation, effectively enhancing the efficiency of organic electroluminescent devices and extending their lifespan. Detailed Implementation

[0010] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0011] In the compounds of this invention, 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.

[0012] In the instruction manual, " "This refers to the portion that is connected to another substituent." It can be attached to any optional position of the attached group / fragment. For example... express , or , express , or And so on.

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

[0014] The halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0015] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 30 carbon atoms, more preferably having 1 to 15 carbon atoms, particularly preferably having 1 to 12 carbon atoms, and most preferably having 1 to 6 carbon atoms. Examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, etc., but are not limited thereto.

[0016] The alkenyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably having 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited thereto.

[0017] The cycloalkyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 30 carbon atoms, more preferably having 3 to 18 carbon atoms, particularly preferably having 3 to 12 carbon atoms, and most preferably having 3 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto.

[0018] The aryl group mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, anthracene, phenanthryl, pyrene, fluoranthyl, triphenylene, 1,2-benzophenanthryl, 2,3-benzophenanthryl, 3,4-benzophenanthryl, perylene, 1-phenylnaphthyl, 2-phenylnaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirofluorenyl, spiro-(adamantane-2,9'-fluoren)yl, spiro(cyclopentane-1,9'-fluoren)yl, spiro(cyclohexane-1,9'-fluoren)yl, benzo9,9-dimethylfluorenyl, benzo9,9-diphenylfluorenyl, etc., but are not limited to these.

[0019] The heteroaryl group described in this invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, selenium, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. Examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazoleyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxolinyl, quinoxalolinyl, benzoquinoxalolinyl, benzoquinoxalolinyl, o-phenanthrolinel, naphridyl, indoleyl, benzothiopheneyl, benzofuranyl, N-hexabenzothiopheneyl, N-hexabenzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, oxadiazolyl, thiazolyl, triazolyl Benzo[a]oxadiazolyl, benzo[thiadiazolyl], benzo[triazolyl], dibenzofuranyl, N-hexadibenzofuranyl, benzo[dibenzofuranyl], dibenzothiophenyl, N-hexadibenzothiophenyl, benzo[dibenzothiophenyl], dibenzoxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, N-hexacarbazoleyl, benzo[carbazoleyl], indo[carbazoleyl], benzofuran[carbazoleyl], benzo[thiaphen[carbazoleyl], acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxthiayl, spirofluorenexanthyl, spirofluorenethionthanthyl, etc., but not limited to these.

[0020] The fused cyclic group of aromatic and alicyclic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aromatic ring and an alicyclic ring fused together. The alicyclic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Examples may include groups such as benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, etc., but are not limited thereto.

[0021] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. The alicyclic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. Examples may include the following groups, but are not limited to: pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc.

[0022] The arylene group described in this invention refers to an aryl group with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the aryl group described above.

[0023] The term "hybrid aryl" as used in this invention refers to a heteroaryl group having two bonding sites, i.e., divalent groups. These sites, apart from being divalent groups, are subject to the above description of heteroaryl groups.

[0024] The fused aromatic and alicyclic cyclic groups described in this invention refer to fused aromatic and alicyclic cyclic groups with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they are subject to the above description of fused aromatic and alicyclic cyclic groups.

[0025] The silyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a silane molecule, and can be represented by the group —Si(Rv)(Rv)(Rv), where Rv is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heteroaryl groups as described above. Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 25 carbon atoms, more preferably 1 to 22 carbon atoms, and most preferably 1 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropylsilyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, etc., but are not limited thereto.

[0026] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted alkenyl, substituted alkynyl, substituted alkoxy, substituted cycloalkyl, substituted silyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroaryl," refers to an independent mono- or polysubstituted group of the following: deuterium, tritium, cyano, nitro, hydroxyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted... The substituents include, but are not limited to, C2-C12 heterocyclic alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C1-C12 alkoxy groups, substituted or unsubstituted C1-C12 alkylthio groups, substituted or unsubstituted C1-C12 alkylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylamino groups, etc. When two or more substituents are present, adjacent substituents may be linked to form a ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterium Naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazole, acridineyl, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, indolyl, etc., but not limited to these.

[0027] In this invention, "the formation of a ring by the connection of adjacent groups" refers to the formation of substituted or unsubstituted aromatic rings, heteroaromatic rings, aliphatic rings, or aliphatic heterocycles by the combination of adjacent groups with each other and optional aromatization. The "adjacent groups" refer to two substituents on two directly connected atoms, a substituent positioned spatially closest to the corresponding substituent, or another substituent on an atom with the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an aliphatic ring can be considered "adjacent" to each other; as shown in the following example: .

[0028] This invention provides a nitrogen-containing heterocyclic compound, the structure of which is shown in Formula 1 or Formula 2: ; X1 and X2 are independently selected from C(R0) or N; R0 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring. Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups. The L1, L2, L3, and L4 are independently selected from one or a combination of single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings in a fused cycloid, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene rings in a fused cycloid. A is independently selected from formula a-1 or formula a-2; The R2 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring. The n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19; The L5 is independently selected from one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings in a fused cycloyl group, or substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene rings in a fused cycloyl group. The Ra is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent Ra can be bonded to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, or 3; The L6 and L7 are independently selected from single bonds or one or a combination of the following groups; ; The R1 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R1s can be bonded to form a substituted or unsubstituted ring. The value of m is independently selected from 0, 1, 2, 3 or 4.

[0029] Preferably, formula 1 or formula 2 is independently selected from one of the following formulas 1-1 to 1-4. ; The R aIndependently selected from any one of the following groups, chosen from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornelane, adamantane, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, or two adjacent R groups. a They can bond to each other to form substituted or unsubstituted benzene rings, naphthalene rings, cyclopentanes, cyclohexanes, or fluorene rings.

[0030] More preferably, formula 1 or formula 2 is independently selected from one of formulas 2-1 to 2-24 below.

[0031]

[0032]

[0033]

[0034]

[0035] ; The R0 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiophene.

[0036] Preferably, L6 and L7 are independently selected from single bonds or one of the following groups:

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] ; R1 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane. Benzenecycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiophene, or two adjacent R1s may be bonded to form substituted or unsubstituted benzene rings, naphthyl rings, cyclopentane, cyclohexane or fluorene rings; The m is independently selected from 0, 1, 2, 3 or 4; the m1 is independently selected from 0, 1 or 2.

[0043] Preferably, L5 is selected from one or a combination of the following groups:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] ; The R2, R i Independently selected from any one of the following groups, whether hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopropane, benzocyclohexane Cycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiophene, or two adjacent R2s may be bonded to form substituted or unsubstituted benzene rings, naphthyl rings, cyclopentane, cyclohexane or fluorene rings; The d1 is independently selected from 0, 1, 2, 3, or 4; the d2 is independently selected from 0, 1, 2, or 3; the d3 is independently selected from 0, 1, or 2; the d4 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the d5 is independently selected from 0, 1, 2, 3, 4, or 5; the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0055] Preferably, formula a-1 is selected from one of the following groups: ; The formula a-2 is selected from one of the following groups: ; The R2 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornelane, adamantane, trimethylsilane, triphenylsilane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiophene.

[0056] Preferably, Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following groups: ; The x is independently selected from C(R) n ) or N; The R n Independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or two adjacent R n They can bond together to form substituted or unsubstituted rings; The ring L is selected from one of the substituted or unsubstituted C3 to C12 alicyclic rings; The U is selected from O, S, or N (R7); The W is selected from O, S, C (R8R9) or N (R 10 ); The R7, R8, R9, R 10 The ring is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R8 and R9 may be bonded to form a substituted or unsubstituted ring.

[0057] More preferably, Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following groups:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] ; The R n Independently selected from any one of the following groups, whether hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilane alkyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, or two adjacent R n They can bond with each other to form substituted or unsubstituted benzene rings, naphthalene rings, cyclopentanes, cyclohexanes, or fluorene rings; The c1 is independently selected from 0, 1, 2, 3, 4, or 5; the c2 is independently selected from 0, 1, 2, 3, or 4; the c3 is independently selected from 0, 1, 2, or 3; the c4 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c7 is independently selected from 0, 1, or 2; and the c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0077] Preferably, one, two, three, or four of Ar1, Ar2, Ar3, and Ar4 are selected from:

[0078]

[0079] .

[0080] Preferably, L1, L2, L3, and L4 are independently selected from single bonds or one or a combination of the following groups: ; The z is independently selected from C(R) r ) or N; The R r Independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or two adjacent R r They bond to each other to form substituted or unsubstituted rings; The ring H is selected from one of the substituted or unsubstituted C3 to C12 alicyclic rings; Q is selected from O, S, or N(R3); M is selected from O, S, C(R4R5) or N(R6); R3, R4, R5, and R6 are independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R4 and R5 may be bonded to form substituted or unsubstituted rings.

[0081] More preferably, L1, L2, L3, and L4 are independently selected from single bonds or one or a combination of the following groups:

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] ; The R rR6 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropane... Silyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, or two adjacent R r They can bond with each other to form substituted or unsubstituted benzene rings, naphthalene rings, cyclopentanes, cyclohexanes, or fluorene rings; The a1 is independently selected from 0, 1, 2, 3, or 4; the a2 is independently selected from 0, 1, 2, or 3; the a3 is independently selected from 0, 1, or 2; the a4 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the a5 is independently selected from 0, 1, 2, 3, 4, or 5; the a6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the a9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0093] Most preferably, the nitrogen-containing heterocyclic compound is selected from any one of the following structures:

[0094]

[0095]

[0096]

[0097] .

[0098] The above lists some specific structural forms of compounds of Formula 1 or Formula 2 described in this invention. However, this invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1 or Formula 2, with substituents as defined above, should be included.

[0099] The preparation methods of compounds of Formula 1 or Formula 2 of the present invention are shown below, but are not limited thereto: Route 1: ; Route 2: ; Following the same preparation method as Formula 1, replace raw material g with Compound of formula 2 can then be obtained.

[0100] The sources of raw materials g, a, b, and c are not particularly limited; they can be commercially available products or prepared using methods commonly used in the field. Y1, Y2, Y3, Y4, and Y5 are independently selected from any one of Cl, Br, and I. W is selected from... or Any one of them.

[0101] In addition, the present invention also provides an organic electroluminescent device comprising a compound of formula 1 or formula 2 of the present invention.

[0102] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer located between the anode and the cathode or outside at least one of the electrodes of the anode and the cathode, the organic layer comprising a compound of Formula 1 or Formula 2 of the present invention.

[0103] Preferably, the organic layer located between the anode and the cathode includes an electron transport region, which contains a compound of Formula 1 or Formula 2 of the present invention.

[0104] More preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, wherein at least one of the electron transport layer and the hole blocking layer comprises a compound of Formula 1 or Formula 2 of the present invention.

[0105] Preferably, the organic layer located between the anode and the cathode includes a light-emitting layer, the light-emitting layer comprising a host material and a dopant material, the host material comprising a compound of Formula 1 or Formula 2 of the present invention.

[0106] More preferably, the host material comprises an n-type host, which comprises a compound of formula 1 or formula 2 of the present invention.

[0107] Preferably, the organic layer located between the cathode and the anode contains a plurality of light-emitting units, and a charge-generating layer is contained between any two adjacent light-emitting units, the charge-generating layer containing a compound of Formula 1 or Formula 2 of the present invention.

[0108] As the anode of the present invention, a transmission electrode, a reflection electrode, or a semi-transmission electrode can be selected. When the anode is a transmission electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the anode is a semi-transmission electrode or a reflection electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0109] As the hole injection layer of the present invention, a material with good hole-accepting ability is preferred. Specific examples include, but are not limited to, metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrene compounds, quinacridones, perylene compounds, etc.

[0110] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Specific examples may include, but are not limited to, materials such as phthalocyanine derivatives, naphtholine derivatives, porphyrin derivatives, benzidine-type triarylamines, styreneamine-type triarylamines, and diamine-type triarylamines.

[0111] As the luminescent layer of this invention, red, green, or blue luminescent materials can be used. These materials typically contain a guest (doped) material and a host material. The guest material can be a simple fluorescent or phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer needs not only to possess bipolar charge transport properties but also appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. Examples of such materials include stilbene aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives, but are not limited to these. The guest material can be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc.

[0112] As the electron transport layer of the present invention, a material with high electron mobility is preferred. Specific examples may include, but are not limited to, quinoline compounds, imidazole compounds, o-phenanthroline compounds, triazole compounds, metal chelates, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, benzimidazole compounds, etc.

[0113] The electron transport layer can be a single-layer structure or a multi-layer structure, and it can contain one or more electron transport materials. Preferred electron transport materials include compounds of formula 1 or formula 2 as described in this invention; or electron transport materials include compounds of formula 1 or formula 2 as described in this invention and metal complexes, including but not limited to LiQ, Alq3, Bepq2, etc.

[0114] The hole blocking layer of this invention has good electron transport capability and hole blocking capability, so as to effectively transport electrons and limit the escape of holes to the light-emitting layer interface. The hole blocking layer material can be selected from metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azirbenzene derivatives, etc., and the preferred hole blocking layer contains the compound of formula 1 or formula 2 described in this invention.

[0115] As the electron injection layer of the present invention, a material with a low work function is preferred. Specific examples may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, etc. Examples may include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0116] As the cathode of the present invention, it can be made of a conductor with a small work function to facilitate electron injection. The cathode material can be selected from metals, metal oxides and / or conductive polymers, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium and their alloys, multilayer structure materials such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0117] The organic layer of the aforementioned organic electroluminescent device can be deposited by vacuum deposition, spin coating, casting, Langmuir-Brønder (LB) method, etc. When using vacuum deposition, the vacuum deposition conditions vary depending on the compound.

[0118] The fabrication of the above-described organic electroluminescent device is specifically described in the following embodiments. However, the following embodiments are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.

[0119] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0120] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0121] Synthesis Example 1: Preparation of Compound 7

[0122] Under nitrogen protection, g-7 (13.55 g, 60.00 mmol), a-7 (20.30 g, 60.00 mmol), and potassium carbonate (16.59 g, 120.00 mmol) were added to the reaction flask. Then, 300 mL of toluene / ethanol / water mixed solvent (toluene:ethanol:water volume ratio = 2:1:1) was added. After purging the air with nitrogen three times, tetrakis(triphenylphosphine)palladium (0.69 g, 0.60 mmol) was added. The reaction was carried out under stirring and reflux for 6 h. After the reaction was completed, the reactants were cooled to room temperature, filtered, and the filter cake was washed with ethanol. The obtained filter cake was recrystallized from toluene to obtain I-7 (17.58 g, 82%), HPLC purity ≥ 99.54%, mass spectrometry m / z: 356.1110 (theoretical value: 356.1099).

[0123] Under nitrogen protection, I-7 (14.29 g, 40.00 mmol), pinacol diboronate (20.32 g, 80.00 mmol), Na₂CO₃ (16.65 g, 160.00 mmol), Pd(dppf)Cl₂ (0.59 g, 0.80 mmol), and 200 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to give intermediate II-7 (16.86 g, yield 78%); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 540.3595 (theoretical value: 540.3582).

[0124] Under nitrogen protection, II-7 (10.81 g, 20.00 mmol), b-7 (10.71 g, 40.00 mmol), and potassium phosphate (16.98 g, 80.00 mmol) were added sequentially to the reaction flask. Then, 200 mL of a toluene / ethanol / water mixture (volume ratio = 2:1:1) was added. The air was purged with nitrogen three times. Palladium acetate (0.09 g, 0.40 mmol) and triphenylphosphine (0.42 g, 1.60 mmol) were added, and the mixture was stirred and heated for 7 h. After the reaction was complete, the system temperature was lowered to room temperature, distilled water was added, and the filter cake was washed with water and ethanol sequentially. The resulting filter cake was recrystallized from toluene to give compound 7 (11.87 g, yield 79%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 750.3483 (theoretical value: 750.3471). Theoretical elemental content (%) C 52 H 42 N6: C, 83.17; H, 5.64; N, 11.19. Measured element content (%): C, 83.20; H, 5.59; N, 11.21.

[0125] Synthesis Example 2: Preparation of Compound 30

[0126] Compound 30 (12.18 g) was prepared by replacing g-7 with g-30 and a-7 with a-30, following the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 800.3640 (theoretical value: 800.3627). Theoretical elemental content (%) C 56 H 44 N6: C, 83.97; H, 5.54; N, 10.49. Measured element content (%): C, 84.00; H, 5.57; N, 10.52.

[0127] Synthesis Example 3: Preparation of Compound 38

[0128]

[0129] Under nitrogen protection, f-38 (39.03 g, 100.00 mmol), pinacol diboronate (25.39 g, 100.00 mmol), Na₂CO₃ (20.81 g, 200.00 mmol), Pd(dppf)Cl₂ (0.73 g, 1.00 mmol), and 200 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to give intermediate a-38 (29.67 g, yield 76%); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 390.2742 (theoretical value: 390.2730).

[0130] Compound 38 (12.53 g) was prepared using the same preparation method as compound 7, but with g-7 replaced by g-38 and a-7 replaced by a-37. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 802.3796 (theoretical value: 802.3784). Theoretical elemental content (%) C 56 H 46 N6: C, 83.76; H, 5.77; N, 10.47. Measured element content (%): C, 83.80; H, 5.81; N, 10.51.

[0131] Synthesis Example 4: Preparation of Compound 60

[0132] Compound 60 (12.95 g) was prepared by replacing g-7 with g-60 and b-7 with b-60, following the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 862.4736 (theoretical value: 862.4723). Theoretical elemental content (%) C 60 H 58 N6: C, 83.49; H, 6.77; N, 9.74. Measured element content (%): C, 83.52; H, 6.81; N, 9.69.

[0133] Synthesis Example 5: Preparation of Compound 96

[0134] Compound 96 (12.21 g) was prepared by replacing g-7 with g-96 using the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 792.3952 (theoretical value: 792.3940). Theoretical elemental content (%) C 55 H 48 N6: C, 83.30; H, 6.10; N, 10.60. Measured element content (%): C, 83.28; H, 6.07; N, 10.56.

[0135] Synthesis Example 6: Preparation of Compound 100

[0136] Compound 100 (12.03 g) was prepared by replacing b-7 with b-100 using the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 770.4739 (theoretical value: 770.4726). Theoretical elemental content (%) C 52 H 22 D 20 N6: C, 81.00; H, 8.10; N, 10.90. Measured element content (%): C, 81.03; H, 8.07; N, 10.86.

[0137] Synthesis Example 7: Preparation of Compound 105

[0138] Under nitrogen protection, g-105 (38.08 g, 120.00 mmol), a-105 (40.71 g, 120.00 mmol), and potassium carbonate (33.17 g, 240.00 mmol) were added to the reaction flask, followed by 600 mL of a toluene / ethanol / water mixed solvent (toluene:ethanol:water volume ratio = 2:1:1). After purging the air with nitrogen three times, tetrakis(triphenylphosphine)palladium (1.39 g, 1.20 mmol) was added. The reaction was carried out under stirring and reflux for 7.5 h. After the reaction was completed, the reactants were cooled to room temperature, filtered, and the filter cake was washed with ethanol. The obtained filter cake was recrystallized from toluene to obtain I-105 (38.66 g, 80%), with an HPLC purity of ≥99.61% and a mass spectrometry m / z of 401.0558 (theoretical value: 401.0546).

[0139] Under nitrogen protection, I-105 (36.25 g, 90.00 mmol), pinacol diboronate (22.85 g, 90.00 mmol), Na₂CO₃ (18.73 g, 180.00 mmol), Pd(dppf)Cl₂ (0.66 g, 0.90 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to give intermediate II-105 (32.79 g, yield 81%); HPLC purity ≥ 99.78%. Mass spectrometry m / z: 449.2307 (theoretical value: 449.2293).

[0140] Under nitrogen protection, II-105 (26.99 g, 60.00 mmol), b-105 (20.63 g, 60.00 mmol), and potassium phosphate (25.47 g, 120.00 mmol) were added sequentially to the reaction flask. Then, 300 mL of a toluene / ethanol / water mixture (volume ratio = 2:1:1) was added. The air was purged with nitrogen three times. Palladium acetate (0.13 g, 0.60 mmol) and triphenylphosphine (0.63 g, 2.40 mmol) were added. The mixture was stirred and heated for 7 h. After the reaction was complete, the system temperature was lowered to room temperature, distilled water was added, and the filter cake was washed with water and ethanol sequentially by vacuum filtration. The obtained filter cake was recrystallized from toluene to obtain compound III-105 (29.54 g, yield 78%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 630.2562 (theoretical value: 630.2550).

[0141] Under nitrogen protection, III-105 (25.25 g, 40.00 mmol), pinacol diborate (10.16 g, 40.00 mmol), Na₂CO₃ (8.32 g, 80.00 mmol), Pd(dppf)Cl₂ (0.29 g, 0.40 mmol), and 200 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to give intermediate IV-105 (22.84 g, yield 79%); HPLC purity ≥ 99.76%. Mass spectrometry m / z: 722.3805 (theoretical value: 722.3792).

[0142] Under nitrogen protection, IV-105 (14.45 g, 20.00 mmol), b-7 (5.35 g, 20.00 mmol), and potassium phosphate (8.49 g, 40.00 mmol) were added sequentially to a reaction flask. Then, 100 mL of a toluene / ethanol / water mixture (volume ratio = 2:1:1) was added. The air was purged with nitrogen three times. Palladium acetate (0.04 g, 0.20 mmol) and triphenylphosphine (0.21 g, 0.80 mmol) were added, and the mixture was stirred and heated for 7 h. After the reaction was complete, the system temperature was lowered to room temperature, distilled water was added, and the filter cake was washed with water and ethanol sequentially. The resulting filter cake was recrystallized from toluene to obtain compound 105 (12.25 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 827.3748 (theoretical value: 827.3736). Theoretical elemental content (%) C 57 H 45 N7: C, 82.68; H, 5.48; N, 11.84. Measured element content (%): C, 82.71; H, 5.52; N, 11.79.

[0143] Synthesis Example 8: Preparation of Compound 122

[0144] Compound 122 (12.92 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-7, and b-105 replaced by b-122. The solid purity was determined by HPLC to be ≥99.93%. Mass spectrometry m / z: 884.4578 (theoretical value: 884.4566). Theoretical elemental content (%) C 62 H 56 N6: C, 84.13; H, 6.38; N, 9.49. Measured element content (%): C, 84.09; H, 6.41; N, 9.52.

[0145] Synthesis Example 9: Preparation of Compound 170

[0146] Compound 170 (14.69 g) was prepared by replacing g-122, a-105, and b-105 with a-170, and b-170, using the same preparation method as compound 105. The solid purity was determined by HPLC to be ≥99.93%. Mass spectrometry m / z: 978.4422 (theoretical value: 978.4410). Theoretical elemental content (%) C 70 H 54N6: C, 85.86; H, 5.56; N, 8.58. Measured element content (%): C, 85.90; H, 5.53; N, 8.62.

[0147] Synthesis Example 10: Preparation of Compound 178

[0148] Compound 178 (12.95 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-178, and b-105 replaced by b-178. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 851.3749 (theoretical value: 851.3736). Theoretical elemental content (%) C 59 H 45 N7: C, 83.17; H, 5.32; N, 11.51. Measured element content (%): C, 83.20; H, 5.28; N, 11.49.

[0149] Synthesis Example 11: Preparation of Compound 186

[0150] Compound 186 (12.24 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-186, a-105 replaced by a-7, and b-105 replaced by b-186. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 826.3796 (theoretical value: 826.3784). Theoretical elemental content (%) C 58 H 46 N6: C, 84.23; H, 5.61; N, 10.16. Measured element content (%): C, 84.19; H, 5.58; N, 10.20.

[0151] Synthesis Example 12: Preparation of Compound 239

[0152] Under nitrogen protection, h-239 (22.97 g, 120.00 mmol), e-239 (46.60 g, 120.00 mmol), and potassium carbonate (33.17 g, 240.00 mmol) were added to the reaction flask, followed by 600 mL of a toluene / ethanol / water mixed solvent (toluene:ethanol:water volume ratio = 2:1:1). After purging the air with nitrogen three times, tetrakis(triphenylphosphine)palladium (1.39 g, 1.20 mmol) was added. The reaction was carried out under stirring and reflux for 7.5 h. After the reaction was completed, the reactants were cooled to room temperature, filtered, and the filter cake was washed with ethanol. The obtained filter cake was recrystallized from toluene to obtain f-239 (34.01 g, 76%) with an HPLC purity of ≥99.59% and a mass spectrometry m / z of 372.1658 (theoretical value: 372.1645).

[0153] Under nitrogen protection, f-239 (33.56 g, 90.00 mmol), pinacol diboronate (22.85 g, 90.00 mmol), Na₂CO₃ (18.73 g, 180.00 mmol), Pd(dppf)Cl₂ (0.66 g, 0.90 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to give intermediate a-239 (32.60 g, yield 78%); HPLC purity ≥ 99.69%. Mass spectrometry m / z: 464.2899 (theoretical value: 464.2887).

[0154] Compound 239 (12.98 g) was prepared using the same preparation method as compound 7, but with g-7 replaced by g-60 and a-7 replaced by a-239. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 876.3953 (theoretical value: 876.3940). Theoretical elemental content (%) C 62 H 48 N6: C, 84.90; H, 5.52; N, 9.58. Measured element content (%): C, 84.88; H, 5.49; N, 9.61.

[0155] Synthesis Example 13: Preparation of Compound 302

[0156] Compound 302 (13.33 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-7, and b-105 replaced by b-302. The solid purity was determined by HPLC to be ≥99.97%. Mass spectrometry m / z: 876.3953 (theoretical value: 876.3940). Theoretical elemental content (%) C 62 H 48 N6: C, 84.90; H, 5.52; N, 9.58. Measured element content (%): C, 84.88; H, 5.49; N, 9.61.

[0157] Synthesis Example 14: Preparation of Compound 368

[0158] Compound 368 (13.52 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-368, a-105 replaced by a-7, and b-105 replaced by b-368. The solid purity was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 900.3928 (theoretical value: 900.3940). Theoretical elemental content (%) C 64 H 48 N6: C, 85.30; H, 5.37; N, 9.33. Measured element content (%): C, 85.28; H, 5.41; N, 9.29.

[0159] Synthesis Example 15: Preparation of Compound 385

[0160] Compound 385 (12.56 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-186, a-105 replaced by a-385, and b-105 replaced by b-385. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 804.3928 (theoretical value: 804.3940). Theoretical elemental content (%) C 56 H 48 N6: C, 83.55; H, 6.01; N, 10.44. Measured element content (%): C, 83.52; H, 5.98; N, 10.48.

[0161] Synthesis Example 16: Preparation of Compound 395

[0162] Compound 395 (13.01 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-7, and b-105 replaced by b-395. The solid purity was determined by HPLC to be ≥99.97%. Mass spectrometry m / z: 866.4084 (theoretical value: 866.4097). Theoretical elemental content (%) C 61 H 50 N6: C, 84.50; H, 5.81; N, 9.69. Measured element content (%): C, 84.47; H, 5.78; N, 9.72.

[0163] Synthetic Example 17: Preparation of Compound 447

[0164] Compound 447 (12.25 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-447, and b-105 replaced by b-447. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 827.3748 (theoretical value: 827.3736). Theoretical elemental content (%) C 57 H 45 N7: C, 82.68; H, 5.48; N, 11.84. Measured element content (%): C, 82.71; H, 5.52; N, 11.81.

[0165] Synthesis Example 18: Preparation of Compound 464

[0166] Compound 464 (14.34 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-186, a-105 replaced by a-7, and b-105 replaced by b-464. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 942.4059 (theoretical value: 942.4046). Theoretical elemental content (%) C 66 H 50 N6O: C, 84.05; H, 5.34; N, 8.91. Measured element content (%): C, 84.01; H, 5.29; N, 8.88.

[0167] Synthesis Example 19: Preparation of Compound 493

[0168] Following the same preparation method as compound 105, g-105 was replaced with g-186, a-105 with a-493, b-105 with b-493, and b-7 with c-493 to prepare compound 493 (14.90 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 992.4215 (theoretical value: 992.4203). Theoretical elemental content (%) C 70 H 52 N6O: C, 84.65; H, 5.28; N, 8.46. Measured element content (%): C, 84.61; H, 5.32; N, 8.50.

[0169] Synthesis Example 20: Preparation of Compound 513

[0170] Compound 513 (13.41 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-513, a-105 replaced by a-7, b-105 replaced by b-513, and b-7 replaced by b-105. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 905.4297 (theoretical value: 905.4285). Theoretical elemental content (%) C 64 H 47 D3N6: C, 84.83; H, 5.89; N, 9.27. Measured elemental content (%): C, 84.79; H, 5.92; N, 9.31.

[0171] Synthesis Example 21: Preparation of Compound 519

[0172] Compound 519 (14.30 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-186, a-105 replaced by a-7, b-105 replaced by b-519, and b-7 replaced by c-519. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 952.4241 (theoretical value: 952.4253). Theoretical elemental content (%) C 68 H 52 N6: C, 85.68; H, 5.50; N, 8.82. Measured element content (%): C, 85.71; H, 5.47; N, 8.78.

[0173] Synthesis Example 22: Preparation of Compound 540

[0174] Compound 540 (14.69 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-122, a-105 replaced by a-7, b-105 replaced by b-540, and b-7 replaced by b-105. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 978.4422 (theoretical value: 978.4410). Theoretical elemental content (%) C 70 H 54 N6: C, 85.86; H, 5.56; N, 8.58. Measured element content (%): C, 85.90; H, 5.52; N, 8.62.

[0175] Synthesis Example 23: Preparation of Compound 575

[0176] Following the same preparation method as compound 105, g-105 was replaced with g-186, a-105 with a-7, b-105 with b-575, and b-7 with c-575 to prepare compound 575 (13.67 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 898.4191 (theoretical value: 898.4179). Theoretical elemental content (%) C 61 H 54 N6Si: C, 81.48; H, 6.05; N, 9.35. Measured elemental content (%): C, 81.52; H, 6.01; N, 9.31.

[0177] Synthesis Example 24: Preparation of Compound 645

[0178] Compound 645 (12.41 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-368, a-105 replaced by a-7, and b-105 replaced by b-513. The solid purity was determined by HPLC to be ≥99.97%. Mass spectrometry m / z: 826.3796 (theoretical value: 826.3784). Theoretical elemental content (%) C 58 H 46 N6: C, 84.23; H, 5.61; N, 10.16. Measured element content (%): C, 84.19; H, 5.57; N, 10.20.

[0179] Synthesis Example 25: Preparation of Compound 677

[0180] Compound 677 (12.41 g) was prepared using the same preparation method as compound 105, but with g-105 replaced by g-677, a-105 replaced by a-7, and b-105 replaced by b-513. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 826.3796 (theoretical value: 826.3784). Theoretical elemental content (%) C 58 H 46 N6: C, 84.23; H, 5.61; N, 10.16. Measured element content (%): C, 84.20; H, 5.58; N, 10.20.

[0181] Synthesis Example 26: Preparation of Compound 698

[0182] Following the same preparation method as compound 105, compound 698 (14.36 g) was prepared by replacing g-105 with g-368, a-105 with a-698, b-105 with b-698, and b-7 with b-186. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 982.4675 (theoretical value: 982.4661). Theoretical elemental content (%) C 70 H 50 D4N6: C, 85.51; H, 5.95; N, 8.55. Measured elemental content (%): C, 85.48; H, 5.93; N, 8.51.

[0183] Synthesis Example 27: Preparation of Compound 769

[0184] Following the same preparation method as compound 105, g-105 was replaced with g-769, a-105 with a-769, b-105 with b-513, and b-7 with c-519 to prepare compound 769 (14.49 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 952.4266 (theoretical value: 952.4253). Theoretical elemental content (%) C 68 H 52 N6: C, 85.68; H, 5.50; N, 8.82. Measured element content (%): C, 85.65; H, 5.47; N, 8.78.

[0185] Synthesis Example 28: Preparation of Compound 780

[0186] Following the same preparation method as compound 105, g-105 was replaced with g-122, a-105 with a-7, b-105 with b-780, and b-7 with c-519 to prepare compound 780 (13.72 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 926.4111 (theoretical value: 926.4097). Theoretical elemental content (%) C 66 H 50 N6: C, 85.50; H, 5.44; N, 9.06. Measured element content (%): C, 85.48; H, 5.48; N, 9.03.

[0187] Synthesis Example 29: Preparation of Compound 829

[0188] Compound 829 (13.37 g) was prepared by replacing b-513 with b-7 using the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 902.4111 (theoretical value: 902.4097). Theoretical elemental content (%) C 64 H 50 N6: C, 85.11; H, 5.58; N, 9.31. Measured element content (%): C, 85.08; H, 5.60; N, 9.28.

[0189] Synthesis Example 30: Preparation of Compound 858

[0190] Following the same preparation method as compound 105, g-105 was replaced with g-122, a-105 with a-7, b-105 with b-858, and b-7 with b-186 to prepare compound 858 (14.88 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 978.4423 (theoretical value: 978.4410). Theoretical elemental content (%) C 70 H 54 N6: C, 85.86; H, 5.56; N, 8.58. Measured element content (%): C, 85.90; H, 5.52; N, 8.61.

[0191] Synthesis Example 31: Preparation of Compound 949

[0192] Following the same preparation method as compound 105, g-105 was replaced with g-186, a-105 with a-7, and b-105 with b-949 to prepare compound 949 (12.40 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 825.3846 (theoretical value: 825.3831). Theoretical elemental content (%) C 59 H 47 N5: C, 85.79; H, 5.74; N, 8.48. Measured element content (%): C, 85.82; H, 5.70; N, 8.51.

[0193] Synthesis Example 32: Preparation of Compound 950

[0194] Following the same preparation method as compound 105, g-105 was replaced with g-950, a-105 with a-7, b-105 with b-949, and b-7 with c-950 to prepare compound 950 (12.38 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 824.3890 (theoretical value: 824.3879). Theoretical elemental content (%) C 60 H 48 N4: C, 87.35; H, 5.86; N, 6.79. Measured elemental content (%): C, 87.39; H, 5.90; N, 6.82.

[0195] Synthesis Example 33: Preparation of Compound 954

[0196] Compound 954 (11.85 g) was prepared by replacing g-7 with g-954 using the same preparation method as compound 7. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 800.3640 (theoretical value: 800.3627). Theoretical elemental content (%) C 56 H 44 N6: C, 83.97; H, 5.54; N, 10.49. Measured element content (%): C, 84.00; H, 5.49; N, 10.52.

[0197] Synthesis Example 34: Preparation of Compound 975

[0198] Following the same preparation method as compound 105, g-105 was replaced with g-122, a-105 with a-7, b-105 with b-7, and b-7 with c-975 to prepare compound 975 (12.81 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 876.3954 (theoretical value: 876.3940). Theoretical elemental content (%) C 62 H 48 N6: C, 84.90; H, 5.52; N, 9.58. Measured element content (%): C, 84.87; H, 5.49; N, 9.61.

[0199] Synthesis Example 35: Preparation of Compound 1020

[0200] Following the same preparation method as compound 105, g-105 was replaced with g-368, a-105 with a-7, b-105 with b-1020, and b-7 with c-1020 to prepare compound 1020 (13.69 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 924.4207 (theoretical value: 924.4192). Theoretical elemental content (%) C 68 H 52 N4: C, 88.28; H, 5.67; N, 6.06. Measured element content (%): C, 88.31; H, 5.70; N, 6.10.

[0201] Device Examples

[0202] Test methods: Driving voltage and luminous efficiency were tested using a combined IVL testing system consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. Lifetime was tested using the McScience M6000 OLED lifetime testing system.

[0203] Test conditions: The test environment was atmospheric, and the temperature was room temperature. The lifespan of the device prepared in this invention was tested (brightness decayed to 95% of its initial brightness), and the current density during the test was 10 mA / cm². 2 .

[0204] Device Example 1: Fabrication of a Red Organic Light Emitting Device

[0205] The ITO transparent glass substrate was 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. Then, it was ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. A 10 nm thick hole injection layer was formed by vacuum evaporating a mixture of HI-P and HT-1 (HI-P:HT-1 mass ratio = 3:97) onto an ITO transparent glass substrate. Then, a 120 nm thick hole transport layer was formed by vacuum evaporating HT-1 onto the hole injection layer. Next, a 30 nm thick light-emitting layer was formed by vacuum evaporating a mixture of RH-1, RH-2, and RD-1 (RH-1:RH-2:RD-1 mass ratio = 48:48:4) onto the hole transport layer. Then, a 30 nm thick electron transport layer was formed by vacuum evaporating a mixture of compound 7 and Liq (compound 1:Liq mass ratio = 1:1). Finally, a 1 nm thick LiF layer was formed as the electron injection layer. Finally, a 130 nm thick Al layer was vacuum evaporated onto the electron injection layer as the cathode. The materials used in Device Example 1 are shown below:

[0206] .

[0207] Device Examples 2-35: Fabrication of Red Organic Light Emitting Devices

[0208] Organic electroluminescent devices were prepared by replacing compound 7 in device example 1 with the compounds listed in Table 1 as the electron transport layer, while keeping the rest of the fabrication process exactly the same.

[0209] Comparative Device Examples 1-5: Fabrication of Red Organic Light-Emitting Devices

[0210] Organic electroluminescent devices were prepared by replacing compound 7 in device example 1 with D1, D2, D3, D4, and D5 as electron transport layers, while keeping the rest of the fabrication process exactly the same.

[0211] Table 1: Test data on the luminescence characteristics of organic electroluminescent devices prepared in Device Examples 1-35 and Comparative Device Examples 1-5

[0212] As shown in Table 1, the nitrogen-containing heterocyclic compound of the present invention has a high electron mobility and a suitable LUMO energy level. When used as an electron transport layer material for organic electroluminescent devices, it can reduce the electron injection transport barrier and reduce the driving voltage; increase the electron mobility rate and achieve carrier transport balance, thereby improving the luminous efficiency and lifetime of organic electroluminescent devices.

[0213] Device Example 36: Fabrication of a Blue Organic Light Emitting Device

[0214] The ITO transparent glass substrate was 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. Then, it was ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. A 10 nm thick hole injection layer was formed by vacuum evaporating a mixture of HI-P and HT-2 (HI-P:HT-2 mass ratio = 2:98) onto an ITO transparent glass substrate. HT-2 was then vacuum evaporated onto the hole injection layer as a hole transport layer, with a thickness of 120 nm. A 30 nm thick light-emitting layer was formed by vacuum evaporating a mixture of BH-3 and BD-2 (BH-3:BD-2 mass ratio = 96:4) onto the hole transport layer. Compound 7 of this invention was then vacuum evaporated onto the light-emitting layer as a hole blocking layer, with a thickness of 10 nm. A 30 nm thick electron transport layer was formed by vacuum evaporating a mixture of ET-1 and Liq (ET-1:Liq mass ratio = 1:1) onto the hole blocking layer. LiF with a thickness of 1 nm was then vacuum evaporated as an electron injection layer. Finally, Al was vacuum evaporated onto the electron injection layer as a cathode, with a thickness of 130 nm. The materials used in device fabrication example 36 are shown below:

[0215] .

[0216] Device Examples 36-70: Fabrication of Blue Organic Light Emitting Devices

[0217] Organic electroluminescent devices were prepared by replacing compound 7 in device example 36 with the compounds listed in Table 2 as hole blocking layers, while keeping the rest of the fabrication process exactly the same.

[0218] Comparative Device Examples 6-7: Fabrication of Blue Organic Light Emitting Devices

[0219] Organic electroluminescent devices were fabricated by replacing compound 7 in device example 36 with D6 and D7 as hole blocking layers, while keeping the rest of the fabrication process exactly the same.

[0220] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 36-70 and Comparative Device Examples 6-7

[0221] As shown in Table 2, the nitrogen-containing heterocyclic compound of the present invention has a high triplet energy level and a suitable HOMO energy level. When used as a hole blocking layer material for organic electroluminescent devices, it can reduce the electron injection transport barrier, confine holes within the light-emitting layer, improve the recombination rate of holes and electrons in the light-emitting layer, avoid excessive local voltage leading to increased device power consumption, and thus improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0222] 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 heterocyclic compound, characterized in that, Represented by Equation 1 or Equation 2 below, ； X1 and X2 are independently selected from C(R0) or N; R0 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring. Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups. The L1, L2, L3, and L4 are independently selected from one or a combination of single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings in a fused cycloid, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene rings in a fused cycloid. A is independently selected from formula a-1 or formula a-2; The R2 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring. The n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 19; The L5 is independently selected from one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings in a fused cycloyl group, or substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroarylene rings in a fused cycloyl group. The Ra is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent Ra can be bonded to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, or 3; The L6 and L7 are independently selected from single bonds or one or a combination of the following groups; ； The R1 is independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R1s can be bonded to form a substituted or unsubstituted ring. The value of m is independently selected from 0, 1, 2, 3 or 4.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The nitrogen-containing heterocyclic compound is selected from one of formulas 1-1 to 1-4. ； The R a Independently selected from any one of the following groups, chosen from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornelane, adamantane, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, or two adjacent R groups. a They can bond to each other to form substituted or unsubstituted benzene rings, naphthalene rings, cyclopentanes, cyclohexanes, or fluorene rings.

3. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The L6 and L7 are independently selected from single bonds or one of the following groups. ； R1 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane. Benzenecycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiophene, or two adjacent R1s may be bonded to form substituted or unsubstituted benzene rings, naphthyl rings, cyclopentane, cyclohexane or fluorene rings; The m is independently selected from 0, 1, 2, 3 or 4; the m1 is independently selected from 0, 1 or 2.

4. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The L5 is selected from one or a combination of the following groups. ； The R2, R i Independently selected from any one of the following groups, whether hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopropane, benzocyclohexane Cycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiophene, or two adjacent R2s may be bonded to form substituted or unsubstituted benzene rings, naphthyl rings, cyclopentane, cyclohexane or fluorene rings; The d1 is independently selected from 0, 1, 2, 3, or 4; the d2 is independently selected from 0, 1, 2, or 3; the d3 is independently selected from 0, 1, or 2; the d4 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the d5 is independently selected from 0, 1, 2, 3, 4, or 5; the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

5. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The Ar1, Ar2, Ar3, and Ar4 groups are independently selected from one of the following groups: ； The R n Independently selected from any one of the following groups, whether hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilane alkyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiopheneyl, or two adjacent R n They can bond with each other to form substituted or unsubstituted benzene rings, naphthalene rings, cyclopentanes, cyclohexanes, or fluorene rings; The c1 is independently selected from 0, 1, 2, 3, 4, or 5; the c2 is independently selected from 0, 1, 2, 3, or 4; the c3 is independently selected from 0, 1, 2, or 3; the c4 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c7 is independently selected from 0, 1, or 2; and the c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

6. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The L1, L2, L3, and L4 are independently selected from single bonds or one or a combination of the following groups: ； The z is independently selected from C(R) r ) or N; The R r Independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or two adjacent R r They bond to each other to form substituted or unsubstituted rings; The ring H is selected from one of the substituted or unsubstituted C3 to C12 alicyclic rings; Q is selected from O, S, or N(R3); M is selected from O, S, C(R4R5) or N(R6); R3, R4, R5, and R6 are independently selected from one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent R4 and R5 may be bonded to form substituted or unsubstituted rings.

7. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The nitrogen-containing heterocyclic compound is selected from any one of the structures shown below. 。 8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or more nitrogen-containing heterocyclic compounds as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer includes an electron transport region containing any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 9, characterized in that, The electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, wherein at least one of the electron transport layer and the hole blocking layer comprises one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 7.

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