Compound containing bis-triazine structure and organic electroluminescent device thereof

Abstract

The invention provides a compound containing a bis-triazine structure and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The invention aims to solve the technical problems that the electron mobility of a conventional electron transport material is relatively low, and the highest occupied molecular orbital (HOMO) energy level of a hole blocking material is relatively shallow, so that the luminous efficiency of an organic electroluminescent device is relatively low. The invention provides the compound containing the bis-triazine structure, the compound has an appropriate triplet state energy level, the electron mobility can be improved, and the compound can effectively improve the luminous efficiency and prolong the service life of the device when being used for functional layer materials such as an electron transport layer and a hole blocking layer of the organic electroluminescent device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are considered the next generation of display technology due to their self-emissive, wide viewing angle, high contrast, and flexibility. Since the advent of high-efficiency green OLED devices with a double-layer structure in 1987, related materials and processes have been continuously iterated, and they have now been applied on a large scale in the high-end display field.

[0003] Typical OLED devices employ a three-layer "sandwich" structure, with the organic functional layers comprising the core components such as a hole transport layer, an emissive layer, and an electron transport layer. To optimize carrier recombination efficiency, electron blocking layers and hole blocking layers are typically placed on either side of the emissive layer to limit exciton quenching and control the position of the recombination region. During device operation, driven by an applied electric field, electrons injected from the cathode and holes injected from the anode recombine within the emissive layer to form excitons, which then emit photons via radiative transitions.

[0004] However, existing functional layer materials still have obvious defects: on the one hand, conventional electron transport materials have low electron mobility, which leads to a mismatch with the hole transport rate, causing carrier recombination region shift and non-equilibrium recombination; on the other hand, commonly used hole blocking materials have shallow highest occupied molecular orbital (HOMO) energy levels, which makes it difficult to form an effective barrier for holes, resulting in holes leaking into the cathode and reducing exciton utilization.

[0005] Therefore, developing electron transport materials with high electron mobility and hole blocking materials with deep HOMO energy levels is of great significance for improving device luminescence efficiency, reducing driving voltage, and extending operating life. Summary of the Invention

[0006] To address the aforementioned problems, this invention provides a compound containing a bistriazine structure and applies it to organic electroluminescent devices. This compound can improve electron mobility, increase the light extraction efficiency of the device, and extend the device's operating life.

[0007] This invention provides a compound containing a bistriazine structure, the compound having the structure shown in Formula 1:

[0008] The Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups. The "substituted" groups in Ar1, Ar2, Ar3, and Ar4 are selected from any one of Formula 1-1, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings, and at least one of Ar1, Ar2, Ar3, and Ar4 comprises one or more of Formula 1-1; In Formula 1-1, Ra is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The La and Lb may be the same or different, and are independently selected from a single bond or any of the following structures:

[0009]

[0010] The a is independently selected from C(R1) or N; The b is independently selected from C(R2) or N, and at least one b is selected from N; The term e is independently selected from C(R3) or N; H1 is selected from O, S, C(R4)2 or N(R5); The ring A is selected from substituted or unsubstituted C3-C20 alicyclic rings; R1, R2, R3, and R5 may be the same or different, and are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C3-C30 heteroaryl ring. The R4 and R6 may be the same or different, and are independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or substituted or unsubstituted rings formed by bonding two adjacent R6s; The L1, L2, L3, and L4 may be the same or different, and are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroarylene rings in a fused cycloalcoholic group.

[0011] The present invention also provides an organic electroluminescent device comprising at least one of the compounds containing a bistriazine structure as described in the present invention.

[0012] Beneficial effects: The compounds containing a bistriazine structure provided by this invention have high electron mobility, which can improve the binding efficiency of holes and electrons. When used as electron transport layer materials in organic electroluminescent devices, they can effectively improve the luminous efficiency of the devices. At the same time, they have deep HOMO energy levels, which can effectively block the migration of holes to the electron transport layer side. When used as hole blocking layer materials in organic electroluminescent devices, they can help optimize the charge balance of the devices, reduce the driving voltage, and effectively increase the recombination probability of charge carriers in the light-emitting layer, further improving the luminous efficiency and extending the lifespan of the devices. Detailed Implementation

[0013] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are only for illustrating the present invention and are not intended to limit the scope of the present invention. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are within the protection scope of the present invention.

[0014] In this specification, " "This refers to the portion that is connected to another substituent."

[0015] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0016] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , And so on.

[0017] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0018] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0019] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0020] 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 15 carbon atoms, more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.

[0021] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, cyclopentenyl, 1-adamantane, 2-adamantane, and norbornane.

[0022] The silyl group described in this invention refers to the -Si(Ra′)3 group, wherein each Ra′ is identical or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each Ra′ is identical or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has C1 to C20 carbon atoms, more preferably C1 to C15, even more preferably C1 to C10, and most preferably C1 to C8. The cycloalkyl group preferably has C3 to C20 carbon atoms, more preferably C3 to C15, even more preferably C3 to C10, and most preferably C3 to C7. Preferably, each Ra′ is identical or different from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0023] The aryl group described in this invention refers to a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0024] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0025] The arylene group referred to in this invention refers to the collective term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; specific examples may include naphthylene, anthraceneene, phenanthrene, pyreneene, terphenylene, fluoranthracene, etc., but are not limited to.

[0026] The heteroarylene group described in this invention refers to the general term for a divalent group in which at least one carbon atom is replaced by a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 3 to 20 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The linking site of the heteroarylene group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroarylene group can be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused-ring heteroarylene group. Specific examples of monocyclic and fused-ring heteroarylene groups include pyridylene, pyrimidinylene, triazineylene, furanylene, thiopheneylene, carbazoylene, benzofuranylene, benzothiopheneylene, benzocarbazoylene, dibenzofuranylene, dibenzothiopheneylene, dibenzocarbazoylene, etc., but are not limited thereto; specific examples of polycyclic heteroarylene groups include bipyridylene, bipyrimidinylene, phenylpyridylene, etc., but are not limited thereto.

[0027] The fused cyclic group of alicyclic and aromatic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from the fused alicyclic and aromatic rings. Preferably, the alicyclic ring has 3 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Preferably, the aromatic ring has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused cyclic group of alicyclic and aromatic rings may include, but is not limited to, benzocyclopropane, benzocyclobutane, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, benzocycloheptenyl, etc.

[0028] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, the alicyclic ring has 3 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Preferably, the heteroaromatic ring has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused cycloyl groups of the alicyclic and heterocyclic rings may include, but are not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium-benzocycloheptyl, pyrimidinium-cyclopropyl, pyrimidinium-cyclobutyl, pyrimidinium-cyclopentyl, pyrimidinium-benzohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc.

[0029] The alicyclic group mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon of an alicyclic hydrocarbon molecule. It can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0030] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted alicyclic, substituted silyl, substituted aryl, substituted heteroaryl, substituted fused alicyclic and aromatic ring, substituted fused alicyclic and heteroaryl ring, substituted arylene, substituted heteroaryl," refers to a group that is independently monosubstituted or polysubstituted by the following groups: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, etc., but not limited to these, or adjacent substituents may be linked to form a ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl The group includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, etc.

[0031] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted cycloalkyl, substituted alicyclic, substituted silyl, substituted aryl, substituted heteroaryl, substituted fused alicyclic and aromatic ring, substituted fused alicyclic and heteroaryl ring, substituted fused polycyclic, substituted aryl, substituted heteroaryl," refers to a group that is independently monosubstituted or polysubstituted by the following groups: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, etc., but not limited to these, or adjacent substituents may be linked to form a ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl The group includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, etc.

[0032] The term "at least one" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.

[0033] This invention provides a compound containing a bistriazine structure, the compound having the structure shown in Formula 1:

[0034] The Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups. The "substituted" groups in Ar1, Ar2, Ar3, and Ar4 are selected from any one of Formula 1-1, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings, and at least one of Ar1, Ar2, Ar3, and Ar4 comprises one or more of Formula 1-1; In Formula 1-1, Ra is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The La and Lb may be the same or different, and are independently selected from a single bond or any of the following structures:

[0035]

[0036] The a is independently selected from C(R1) or N; The b is independently selected from C(R2) or N, and at least one b is selected from N; The term e is independently selected from C(R3) or N; H1 is selected from O, S, C(R4)2 or N(R5); The ring A is selected from substituted or unsubstituted C3-C20 alicyclic rings; R1, R2, R3, and R5 may be the same or different, and are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C3-C30 heteroaryl ring. The R4 and R6 may be the same or different, and are independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or substituted or unsubstituted rings formed by bonding two adjacent R6s; The L1, L2, L3, and L4 may be the same or different, and are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroarylene rings in a fused cycloalcoholic group.

[0037] Preferably, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any one of the following structures:

[0038] The i is independently selected from C(R8) or N; The u is independently selected from C(R8′) or N; The P1 is selected from O, S, C(R9)2 or N(R) 10 ); P2 is selected from O, S, C(R) 11 )2 or N(R 12 ); The ring B is selected from substituted or unsubstituted C3-C20 alicyclic rings; The R8 and R8′ may be the same or different, and are independently selected from any one of the following: formula 1-1, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or two adjacent R8 and two adjacent R8′ are bonded to each other to form a substituted or unsubstituted ring; The R9, R 11The same or different, independently selected from any one of the following: formula 1-1, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or two adjacent R 11 They bond with each other to form substituted or unsubstituted rings; The R 10 R 12 The same or different, independently selected from any one of the following: formula 1-1, hydrogen, deuterium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring.

[0039] Preferably, Ar1, Ar2, Ar3, and Ar4 are the same or different, and are independently selected from any one of the following structures:

[0040]

[0041] R8 and R8′ are independently selected from formula 1-1, hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R9, R 11 The group is independently selected from formula 1-1, hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R 10 R 12 The group is independently selected from formula 1-1, hydrogen, deuterium, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, or 4; the n3 is selected from 0, 1, 2, or 3; the n4 is selected from 0, 1, or 2; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n6 is selected from 0, 1, 2, 3, 4, 5, or 6; the n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; n 11 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0042] Preferably, one, two, three, or four of Ar1, Ar2, Ar3, and Ar4 are independently selected from any of the following structures: .

[0043] Preferably, the phrase “at least one of Ar1, Ar2, Ar3, and Ar4 contains one or more formulas 1-1” includes one of Ar1, Ar2, Ar3, and Ar4 (Ar1, Ar2, Ar3, or Ar4), two (Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar4, Ar2 and Ar3, Ar2 and Ar4, or Ar3 and Ar4), three (Ar1, Ar2 and Ar3, Ar1, Ar2 and Ar4, Ar1, Ar3 and Ar4, or Ar2, Ar3 and Ar4), and four (Ar1, Ar2, Ar3, and Ar4) each containing one, two, three, or four formulas 1-1 (preferably, one, two, three, or four R8s are selected from formula 1-1).

[0044] Preferably, Ar1 contains at most two formulas 1-1; Ar2 contains at most two formulas 1-1; Ar3 contains at most two formulas 1-1; and Ar4 contains at most two formulas 1-1.

[0045] Preferably, the compound comprises one, two, three, or four R8s.

[0046] Preferably, Ra is independently selected from hydrogen, deuterium, 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 adamantyl, and substituted or unsubstituted norbornyl.

[0047] Preferably, Ra is independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl.

[0048] Preferably, Ra is independently selected from substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, and substituted or unsubstituted cyclohexane.

[0049] Preferably, La and Lb may be the same or different, and are independently selected from single bonds or any of the following structures:

[0050]

[0051] ; R1 and R2 are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R1′ is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. R3, R4, R5, R6, and R7 are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiopheneyl. c1 is selected from 0, 1, 2, 3 or 4; c2 is selected from 0, 1, 2 or 3; c3 is selected from 0, 1 or 2; c4 is selected from 0, 1, 2, 3, 4 or 5; c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c7 is selected from 0, 1, 2, 3, 4, 5 or 6; c8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; c9 is selected from 0 or 1.

[0052] Preferably, La contains at most three, at most two, or at most one selected from phenylene, biphenylene, pyridinyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, and benzocyclohexane; Lb contains at most three, at most two, or at most one selected from phenylene, biphenylene, pyridinyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, and benzocyclohexane.

[0053] Preferably, La and Lb are not both selected from single bonds.

[0054] Preferably, L1, L2, L3, and L4 may be the same or different, and are independently selected from single bonds or any of the following structures:

[0055]

[0056] The u is independently selected from C(Rb) or N; G1 is selected from O, S, C(Rc)2 or N(Rd); The G2 is selected from O, S, C(Re)2 or N(Rf); The ring C is independently selected from substituted or unsubstituted C3 to C20 alicyclic rings; The Rb, Rc, and Re are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or any one of the following: two adjacent Rb and two adjacent Re are bonded together to form a substituted or unsubstituted ring. The Rd and Rf are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring.

[0057] More preferably, L1, L2, L3, and L4 may be the same or different, and are independently selected from single bonds or any of the following structures: ; Preferably, Rb, Rc, and Re are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiophene. Preferably, Rd and Rf are independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The d1 is 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; and the d7 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0058] Most preferably, Formula 1 is selected from one of the following structures: .

[0059] The above lists some specific structural forms of compounds represented by Formula 1 in this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents as defined above is included.

[0060] The present invention provides a method for preparing the compound represented by Formula 1, which is carried out by the Suzuki coupling reaction and the Miyaura borylation reaction well known in the art, but the preparation method of the present invention is not limited thereto.

[0061] Synthesis Route 1:

[0062] Synthesis Route 2:

[0063] When intermediate b is the same as intermediate c, two times the amount of b or c can be introduced in a one-step reaction to synthesize compound 1; The Xa to Xd may be the same as or different from each other, and are selected from any one of I, Br, and Cl; the limitations of Ar1, Ar2, Ar3, Ar4, La, Lb, L1, L2, L3, and L4 are the same as those described above.

[0064] The present invention also provides an organic electroluminescent device comprising at least one of the compounds containing a bistriazine structure as described in the present invention.

[0065] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains at least one of the compounds containing a bistriazine structure as described in this invention.

[0066] Preferably, the organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the electron transport region contains at least one of the compounds containing a bistriazine structure as described in this invention.

[0067] More preferably, the electron transport region includes at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer contains at least one of the compounds containing a bis(triazine) structure as described in this invention. Specifically, the electron transport layer contains a compound containing a bis(triazine) structure as described in this invention. Or the hole blocking layer contains a compound containing a bis(triazine) structure as described in this invention. Or both the electron transport layer and the hole blocking layer contain at least one of the compounds containing a bis(triazine) structure as described in this invention.

[0068] Preferably, the light-emitting layer contains at least one of the compounds containing a bistriazine structure as described in this invention.

[0069] More preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material contains at least one of the compounds containing a bistriazine structure as described in this invention.

[0070] Preferably, the organic electroluminescent devices of the present invention are divided into single-layer organic electroluminescent devices and multilayer organic electroluminescent devices. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit. The multilayer organic electroluminescent device is an organic electroluminescent device formed by connecting two or more independent light-emitting units in series through a charge-generating layer. The charge-generating layer contains at least one of the compounds containing a bistriazine structure as described in the present invention.

[0071] The organic electroluminescent device of the present invention may further include a substrate. The substrate of the present invention is preferably made of a material that does not change when forming electrodes and other functional layers. Specific examples of substrate materials that can be used in the present invention may include glass, quartz, plastic, polymer film, silicon, etc., but are not limited thereto.

[0072] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The anode material described in this invention is preferably a material with a high work function. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode 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 material used to form the anode 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. The anode can have a single-layer structure or a multi-layer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0073] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0074] The hole transport layer material described in this invention is preferably a material with high hole mobility. The hole transport layer material may include, but is not limited to, biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc.

[0075] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material and dopants. The luminescent layer material may contain multiple host materials and multiple dopants. The dopants can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The doping ratio of the host material and the dopants can vary depending on the materials used; preferably, the doping concentration of the dopant, based on the host compound, is less than 20 wt%. Fluorescent compounds can be used as dopants, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolineazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as iridium complexes, osmium complexes, platinum complexes and other metal complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylated iridium (FIrpic), tri(2-phenylpyridine)iridium (Ir(ppy)3), acetylacetonate di(2-phenylpyridine)iridium (Ir(ppy)2(acac)), etc.

[0076] The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material may contain the following compounds, including but not limited to naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, phenanthrene compounds, fluoranthene compounds, anthracene compounds, pentanebenzene compounds, perylene compounds, diarylene compounds, triphenylamine ethylene compounds, amine compounds, carbazole compounds, benzimidazole compounds, furan compounds, organometallic fluorescent complexes, organometallic phosphorescent complexes (such as Ir, Pt, Os, Cu, Au), polyvinylcarbazole, polyorganosilicon compounds, polythiophene, and other organic polymeric luminescent materials, but not limited to these.

[0077] The electron transport material of the organic light-emitting device of this invention is required to have excellent electron transport performance, effectively transporting electrons from the cathode to the light-emitting layer, and possessing a high electron mobility. In addition to the compound of Formula 1 provided by this invention, it may also contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited thereto.

[0078] The hole-blocking material in the electron transport region described in this invention requires a high triplet energy level and good electron transport performance. In addition to the compound of Formula 1 provided in this invention, it may also contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited thereto.

[0079] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material 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, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0080] The cathode material described in this invention is preferably a material with a low work function, and the cathode can be selected from a transmission electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmission electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0081] 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 it is not limited to these methods.

[0082] 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.

[0083] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0084] 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. Synthesis Example 1: Preparation of Intermediate c-131

[0085] Under nitrogen protection, m-131 ​​(33.91 g, 150 mmol), n-131 (35.43 g, 150 mmol), and potassium carbonate (41.46 g, 300 mmol) were added to the reaction flask. Then, 625 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, Pd(PPh3)4 (0.17 g, 0.15 mmol) was added. The reaction was carried out under stirring and reflux for 5.5 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 c-131 (46.05 g, 72%) with HPLC purity ≥99.74% and mass spectrometry m / z: 425.0915 (theoretical value: 425.0923).

[0086] Synthesis Example 2: Preparation of Compound 1

[0087] Preparation of intermediate A-1: Under nitrogen protection, a-1 (28.72 g, 150 mmol), pinacol diboronate (38.09 g, 150 mmol), and KOAc (29.44 g, 300 mmol) were added to the reaction flask, followed by 500 mL of DMF solution. After purging the air with nitrogen three times, Pd(dppf)Cl2 (1.10 g, 1.5 mmol) was added. The mixture was heated and stirred for 5 h. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (400 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, and the resulting solid was purified with n-hexane:ethyl acetate = 9:1 (v / v) to obtain intermediate A-1 (30.77 g, 86%) with HPLC purity ≥ 99.72% and mass spectrometry m / z: 238.0941 (theoretical value: 238.0932).

[0088] Preparation of intermediate B-1: Under nitrogen protection, A-1 (23.85 g, 100 mmol), b-1 (26.77 g, 100 mmol), and potassium phosphate (42.45 g, 200 mmol) were added sequentially to the reaction flask. Then, 400 mL of a toluene / ethanol / water (volume ratio = 2:1:1) mixed solution was added. The air was purged with nitrogen three times. Pd(OAc)2 (0.22 g, 1.0 mmol) and triphenylphosphine (0.52 g, 2.0 mmol) were added. The mixture was stirred and heated for 8.5 h. After the reaction was completed, the system temperature was lowered to room temperature, distilled water was added, and the mixture was filtered. The filter cake was washed with water and ethanol sequentially. The obtained filter cake was recrystallized from toluene to obtain intermediate B-1 (25.79 g, 75%). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 343.0885 (theoretical value: 343.0876).

[0089] Preparation of intermediate C-1: Under nitrogen protection, B-1 (20.63 g, 60 mmol), pinacol diboronate (15.24 g, 60 mmol), and KOAc (11.78 g, 120 mmol) were added to the reaction flask, followed by 300 mL of DMF solution. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.44 g, 0.6 mmol) was added. The mixture was heated and stirred for 5 h. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (400 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, and the resulting solid was purified with n-hexane:ethyl acetate = 9:1 (v / v) to obtain intermediate C-1 (22.99 g, 88%) with HPLC purity ≥ 99.86% and mass spectrometry m / z: 435.2111 (theoretical value: 435.2118).

[0090] Preparation of compound 1: Under nitrogen protection, C-1 (13.06 g, 30 mmol), c-1 (10.20 g, 30 mmol), and potassium phosphate (12.74 g, 60 mmol) were added sequentially to the reaction flask. Then, 400 mL of a toluene / ethanol / water mixture (volume ratio = 2:1:1) was added. The air was purged with nitrogen three times. Pd(OAc)₂ (0.07 g, 0.3 mmol) and triphenylphosphine (0.16 g, 0.6 mmol) were added, and the mixture was stirred and heated for 8.5 h. After the reaction was complete, the system temperature was lowered to room temperature, distilled water was added, and the mixture was filtered. The filter cake was washed successively with water and ethanol. The resulting filter cake was recrystallized from toluene to obtain compound 1 (13.60 g, 74%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 612.2466 (theoretical value: 612.2458). Theoretical elemental content (%) C 39 H32 N6Si: C, 76.44; H, 5.26; N, 13.71. Measured elemental content (%): C, 76.43; H, 5.24; N, 13.72.

[0091] Synthesis Example 3: Preparation of Compound 5

[0092] Following the same preparation method as in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-5 to obtain compound 5 (15.44 g), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 612.2450 (theoretical value: 612.2458). Theoretical elemental content (%) C 39 H 32 N6Si: C, 76.44; H, 5.26; N, 13.71. Measured elemental content (%): C, 76.42; H, 5.23; N, 13.76.

[0093] Synthesis Example 4: Preparation of Compound 64

[0094] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-64, and c-1 was replaced with an equimolar amount of c-64, yielding compound 64 (15.50 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 688.2762 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.42; H, 5.29; N, 12.21.

[0095] Synthesis Example 5: Preparation of Compound 71

[0096] Preparation of intermediate A-71: Under nitrogen protection, a-71 (21.05 g, 80 mmol), pinacol diboronate (40.63 g, 160 mmol), and KOAc (23.55 g, 240 mmol) were added to the reaction flask, followed by 400 mL of DMF solution. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.59 g, 0.8 mmol) was added. The mixture was heated and stirred for 5 h. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (400 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, and the resulting solid was purified with n-hexane:ethyl acetate = 9:1 (v / v) to obtain intermediate A-71 (30.35 g, 85%) with HPLC purity ≥ 99.72% and mass spectrometry m / z: 446.2809 (theoretical value: 446.2800).

[0097] Preparation of compound 71: Under nitrogen protection, A-71 (13.39 g, 30 mmol), c-1 (20.39 g, 60 mmol), and potassium phosphate (19.10 g, 90 mmol) were added sequentially to the reaction flask. Then, 400 mL of a toluene / ethanol / water mixture (volume ratio = 2:1:1) was added. The air was purged with nitrogen three times. Pd(OAc)₂ (0.13 g, 0.6 mmol) and triphenylphosphine (0.24 g, 0.9 mmol) were added, and the mixture was stirred and heated for 8.5 h. After the reaction was complete, the system temperature was lowered to room temperature, distilled water was added, and the mixture was filtered. The filter cake was washed successively with water and ethanol. The resulting filter cake was recrystallized from toluene to obtain compound 71 (19.71 g, 82%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 800.3470 (theoretical value: 800.3479). Theoretical elemental content (%) C 51 H 48 N6Si2: C, 76.46; H, 6.04; N, 10.49. Measured elemental content (%): C, 76.48; H, 6.03; N, 10.50.

[0098] Synthesis Example 6: Preparation of Compound 73

[0099] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-73 to obtain compound 73 (16.47 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 712.2779 (theoretical value: 712.2771). Theoretical elemental content (%) C 47 H 36N6Si: C, 79.18; H, 5.09; N, 11.79. Measured elemental content (%): C, 79.19; H, 5.11; N, 11.76.

[0100] Synthesis Example 7: Preparation of Compound 80

[0101] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-80 to obtain compound 80 (14.54 g), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 637.2401 (theoretical value: 637.2410). Theoretical elemental content (%) C 40 H 31 N7Si: C, 75.33; H, 4.90; N, 15.37. Measured elemental content (%): C, 75.35; H, 4.91; N, 15.33.

[0102] Synthesis Example 8: Preparation of Compound 83

[0103] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-83 to obtain compound 83 (15.28 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 652.2778 (theoretical value: 652.2771). Theoretical elemental content (%) C 42 H 36 N6Si: C, 77.27; H, 5.56; N, 12.87. Measured elemental content (%): C, 77.22; H, 5.58; N, 12.88.

[0104] Synthesis Example 9: Preparation of Compound 113

[0105] Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-113 to obtain compound 113 (15.96 g), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 728.3075 (theoretical value: 728.3084). Theoretical elemental content (%) C 48 H 40 N6Si: C, 79.09; H, 5.53; N, 11.53. Measured elemental content (%): C, 79.11; H, 5.52; N, 11.55.

[0106] Synthesis Example 10: Preparation of Compound 123

[0107] Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-123 to obtain compound 123 (16.64 g), with an HPLC purity ≥99.99%. Mass spectrometry m / z: 729.2680 (theoretical value: 729.2672). Theoretical elemental content (%) C 46 H 35 N7OSi: C, 75.69; H, 4.83; N, 13.43. Measured elemental content (%): C, 75.68; H, 4.85; N, 13.47.

[0108] Synthetic Example 11: Preparation of Compound 131

[0109] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-131, b-1 with an equimolar amount of b-131, and c-1 with an equimolar amount of c-131, yielding compound 131 (15.02 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 704.3094 (theoretical value: 704.3084). Theoretical elemental content (%) C 46 H 40 N6Si: C, 78.37; H, 5.72; N, 11.92. Measured elemental content (%): C, 78.33; H, 5.74; N, 11.93.

[0110] Synthesis Example 12: Preparation of Compound 211

[0111] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-211 to obtain compound 211 (15.29 g), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 688.2779 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.48; H, 5.26; N, 12.21.

[0112] Synthesis Example 13: Preparation of Compound 230

[0113] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-230, and c-1 was replaced with an equimolar amount of c-230, yielding compound 230 (17.67 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 764.3092 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.08; H, 5.25; N, 10.97.

[0114] Synthesis Example 14: Preparation of Compound 248

[0115] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-248, and b-1 was replaced with an equimolar amount of b-248, yielding compound 248 (18.68 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 818.3560 (theoretical value: 818.3553). Theoretical elemental content (%) C 55 H 46 N6Si: C, 80.65; H, 5.66; N, 10.26. Measured elemental content (%): C, 80.68; H, 5.67; N, 10.24.

[0116] Synthesis Example 15: Preparation of Compound 249

[0117] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-249 to obtain compound 249 (17.15 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 688.2782 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.49; H, 5.26; N, 12.18.

[0118] Synthesis Example 16: Preparation of Compound 294

[0119] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-230, and b-1 was replaced with an equimolar amount of b-294, yielding compound 294 (18.83 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 814.3249 (theoretical value: 814.3240). Theoretical elemental content (%) C 55 H 42 N6Si: C, 81.05; H, 5.19; N, 10.31. Measured elemental content (%): C, 81.06; H, 5.17; N, 10.35.

[0120] Synthesis Example 17: Preparation of Compound 300

[0121] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-300, and b-1 was replaced with an equimolar amount of b-300, yielding compound 300 (18.94 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 852.3390 (theoretical value: 852.3397). Theoretical elemental content (%) C 58 H 44 N6Si: C, 81.66; H, 5.20; N, 9.85. Measured elemental content (%): C, 81.68; H, 5.21; N, 9.82.

[0122] Synthesis Example 18: Preparation of Compound 333

[0123] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-333, and b-1 was replaced with an equimolar amount of b-333, yielding compound 333 (15.73 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 698.3390 (theoretical value: 698.3398). Theoretical elemental content (%) C 45 H 26 D 10 N6Si: C, 77.33; H, 6.63; N, 12.02. Measured elemental content (%): C, 77.35; H, 6.64; N, 12.01.

[0124] Synthesis Example 19: Preparation of Compound 339

[0125] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-339, and c-1 was replaced with an equimolar amount of c-339, yielding compound 339 (17.47 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 765.3488 (theoretical value: 765.3480). Theoretical elemental content (%) C 48 H 39 D5N6Si2: C, 75.25; H, 6.45; N, 10.97. Measured elemental content (%): C, 75.21; H, 6.46; N, 10.99.

[0126] Synthesis Example 20: Preparation of Compound 346

[0127] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-249, and c-1 was replaced with an equimolar amount of c-339, yielding compound 346 (18.49 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 760.3179 (theoretical value: 760.3166). Theoretical elemental content (%) C 48 H 44 D5N6Si2: C, 75.75; H, 5.83; N, 11.04. Measured elemental content (%): C, 75.72; H, 5.85; N, 11.03.

[0128] Synthesis Example 21: Preparation of Compound 363

[0129] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-363, and c-1 was replaced with an equimolar amount of c-339, yielding compound 363 (21.19 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 904.3950 (theoretical value: 904.3957). Theoretical elemental content (%) C 54 H 60 N6Si4: C, 71.63; H, 6.68; N, 9.28. Measured elemental content (%): C, 71.65; H, 6.67; N, 9.29.

[0130] Synthesis Example 22: Preparation of Compound 375

[0131] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-375 to obtain compound 375 (16.33 g), with an HPLC purity ≥99.92%. Mass spectrometry m / z: 688.2782 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.45; H, 5.24; N, 12.23.

[0132] Synthesis Example 23: Preparation of Compound 399

[0133] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-399 to obtain compound 399 (15.50 g), with an HPLC purity ≥99.97%. Mass spectrometry m / z: 688.2779 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.48; H, 5.22; N, 12.21.

[0134] Synthesis Example 24: Preparation of Compound 443

[0135] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-443, and b-1 was replaced with an equimolar amount of b-443, yielding compound 443 (19.91 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 872.2874 (theoretical value: 872.2866). Theoretical elemental content (%) C 55 H 40 N8SSi: C, 75.66; H, 4.62; N, 12.83. Measured elemental content (%): C, 75.68; H, 4.61; N, 12.86.

[0136] Synthesis Example 25: Preparation of Compound 456

[0137] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-456, and b-1 was replaced with an equimolar amount of b-456, yielding compound 456 (16.75 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 764.3096 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.09; H, 5.21; N, 10.98.

[0138] Synthesis Example 26: Preparation of Compound 464

[0139] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-464, and b-1 was replaced with an equimolar amount of b-464, yielding compound 464 (17.78 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 789.3044 (theoretical value: 789.3036). Theoretical elemental content (%) C 52 H 39 N7Si: C, 79.06; H, 4.98; N, 12.41. Measured elemental content (%): C, 79.05; H, 4.99; N, 12.37.

[0140] Synthesis Example 27: Preparation of Compound 480

[0141] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-375, and b-1 was replaced with an equimolar amount of b-480, yielding compound 480 (16.83 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 778.2883 (theoretical value: 778.2876). Theoretical elemental content (%) C 51 H 38 N6OSi: C, 78.64; H, 4.92; N, 10.79. Measured elemental content (%): C, 78.67; H, 4.90; N, 10.78.

[0142] Synthesis Example 28: Preparation of Compound 492

[0143] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-492, and b-1 was replaced with an equimolar amount of b-492, yielding compound 492 (16.01 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 720.3325 (theoretical value: 720.3335). Theoretical elemental content (%) C 47 H 36 D4N6Si: C, 78.30; H, 6.15; N, 11.66. Measured elemental content (%): C, 78.31; H, 6.13; N, 11.68.

[0144] Synthesis Example 29: Preparation of Compound 523

[0145] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-480, b-1 with an equimolar amount of c-339, and c-1 with an equimolar amount of c-523, yielding compound 523 (19.36 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 837.3884 (theoretical value: 837.3875). Theoretical elemental content (%) C 51 H 47 D5N6Si3: C, 73.07; H, 6.85; N, 10.03. Measured elemental content (%): C, 73.09; H, 6.81; N, 10.04.

[0146] Synthesis Example 30: Preparation of Compound 530

[0147] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-530, and c-1 was replaced with an equimolar amount of c-530, yielding compound 530 (19.73 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 912.3799 (theoretical value: 912.3792). Theoretical elemental content (%) C 60 H 52 N6Si2: C, 78.91; H, 5.74; N, 9.20. Measured elemental content (%): C, 78.92; H, 5.76; N, 9.17.

[0148] Synthesis Example 31: Preparation of Compound 536

[0149] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-530, and c-1 was replaced with an equimolar amount of c-536, yielding compound 536 (19.64 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 860.3471 (theoretical value: 860.3479). Theoretical elemental content (%) C 56 H 48 N6Si2: C, 78.10; H, 5.62; N, 9.76. Measured elemental content (%): C, 78.13; H, 5.64; N, 9.72.

[0150] Synthesis Example 32: Preparation of Compound 552

[0151] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-552 to obtain compound 552 (16.75 g), with an HPLC purity ≥99.97%. Mass spectrometry m / z: 764.3092 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.08; H, 5.29; N, 10.98.

[0152] Synthesis Example 33: Preparation of Compound 596

[0153] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-596, and c-1 was replaced with an equimolar amount of c-596, yielding compound 596 (18.97 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 820.3703 (theoretical value: 820.3710). Theoretical elemental content (%) C 55 H 48 N6Si: C, 80.45; H, 5.89; N, 10.24. Measured elemental content (%): C, 80.48; H, 5.88; N, 10.25.

[0154] Synthesis Example 34: Preparation of Compound 635

[0155] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-635, and b-1 was replaced with an equimolar amount of b-635, yielding compound 635 (16.78 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 765.3046 (theoretical value: 765.3036). Theoretical elemental content (%) C 50 H 39 N7Si: C, 78.40; H, 5.13; N, 12.80. Measured elemental content (%): C, 78.42; H, 5.12; N, 12.77.

[0156] Synthesis Example 35: Preparation of Compound 639

[0157] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-639, and b-1 was replaced with an equimolar amount of b-456, yielding compound 639 (18.92 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 840.3390 (theoretical value: 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental content (%): C, 81.38; H, 5.28; N, 9.97.

[0158] Synthesis Example 36: Preparation of Compound 658

[0159] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-658, and b-1 was replaced with an equimolar amount of b-658, yielding compound 658 (19.47 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 888.3388 (theoretical value: 888.3397). Theoretical elemental content (%) C 61 H 44 N6Si: C, 82.40; H, 4.99; N, 9.45. Measured elemental content (%): C, 82.41; H, 4.96; N, 9.48.

[0160] Synthesis Example 37: Preparation of Compound 664

[0161] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-658, and b-1 was replaced with an equimolar amount of b-664, yielding compound 664 (18.72 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 820.2814 (theoretical value: 820.2804). Theoretical elemental content (%) C 53 H 40 N6SSi: C, 77.53; H, 4.91; N, 10.24. Measured elemental content (%): C, 77.51; H, 4.95; N, 10.23.

[0162] Synthesis Example 38: Preparation of Compound 683

[0163] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-664, and b-1 was replaced with an equimolar amount of b-683, yielding compound 683 (21.89 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 934.4853 (theoretical value: 934.4840). Theoretical elemental content (%) C 63 H 30 D 18 N6Si: C, 80.90; H, 7.11; N, 8.99. Measured elemental content (%): C, 80.86; H, 7.12; N, 9.01.

[0164] Synthesis Example 39: Preparation of Compound 697

[0165] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-697, and c-1 was replaced with an equimolar amount of c-339, yielding compound 697 (18.84 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 836.3471 (theoretical value: 836.3479). Theoretical elemental content (%) C 54 H 48 N6Si2: C, 77.47; H, 5.78; N, 10.04. Measured elemental content (%): C, 77.49; H, 5.77; N, 10.01.

[0166] Synthesis Example 40: Preparation of Compound 724

[0167] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-724 to obtain compound 724 (19.34 g), with an HPLC purity ≥99.93%. Mass spectrometry m / z: 836.3467 (theoretical value: 836.3479). Theoretical elemental content (%) C 54 H 48 N6Si2: C, 77.47; H, 5.78; N, 10.04. Measured elemental content (%): C, 77.48; H, 5.73; N, 10.06.

[0168] Synthesis Example 41: Preparation of Compound 738

[0169] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-738 to obtain compound 738 (18.13 g), with an HPLC purity ≥99.97%. Mass spectrometry m / z: 764.3072 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.09; H, 5.28; N, 10.97.

[0170] Synthesis Example 42: Preparation of Compound 837

[0171] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-837 to obtain compound 837 (18.08 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 836.3486 (theoretical value: 836.3479). Theoretical elemental content (%) C 54 H 48 N6Si2: C, 77.47; H, 5.78; N, 10.04. Measured elemental content (%): C, 77.49; H, 5.74; N, 10.05.

[0172] Synthesis Example 43: Preparation of Compound 962

[0173] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-962 to obtain compound 962 (18.82 g), with an HPLC purity ≥99.91%. Mass spectrometry m / z: 764.3096 (theoretical value: 764.3084). Theoretical elemental content (%) C 51H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.05; H, 5.30; N, 10.94.

[0174] Synthesis Example 44: Preparation of Compound 1049

[0175] Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-1049, b-1 with an equimolar amount of b-635, and c-1 with an equimolar amount of c-5, yielding compound 1049 (18.61 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 765.3048 (theoretical value: 765.3036). Theoretical elemental content (%) C 50 H 39 N7Si: C, 78.40; H, 5.13; N, 12.80. Measured elemental content (%): C, 78.42; H, 5.10; N, 12.82.

[0176] Synthetic Example 45: Preparation of Compound 1050

[0177] Following the same preparation method as in Synthesis Example 5, a-71 was replaced with an equimolar amount of a-1050 to obtain compound 1050 (19.54 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 834.3312 (theoretical value: 834.3322). Theoretical elemental content (%) C 54 H 46 N6Si2: C, 77.66; H, 5.55; N, 10.06. Measured elemental content (%): C, 77.64; H, 5.58; N, 10.05.

[0178] [Device Examples]

[0179] The instruments used to test the device performance in this invention consist of a combined IVL testing system comprising testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. This system was used to test the driving voltage and luminous efficiency of the organic electroluminescent device. The lifetime test employed the McScience M6000 OLED lifetime testing system. The testing conditions were atmospheric conditions, room temperature, and a current density of 10 mA / cm². 2 .

[0180] [Device Example 1]

[0181] First, a transparent conductive ITO glass substrate is used as the anode and ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0182] A hole injection layer with a thickness of 20 nm was formed by vacuum evaporation of HT-1:HI-1 = 97:3 (wt%) on an ITO glass substrate; a hole transport layer with a thickness of 120 nm was formed by vacuum evaporation of HT-1 on the hole injection layer; RH-1 and RH-2 were vacuum evaporated on the hole transport layer at a ratio of 1:1 (wt%), and RD-1 was evaporated with a doping amount of 7 wt% based on the total amount of the host and dopant, resulting in a light-emitting layer thickness of 40 nm; an electron transport layer with a thickness of 35 nm was formed by vacuum evaporation of compound 1 and Liq on the light-emitting layer at a ratio of 1:1 (wt%); a LiF layer with a thickness of 1 nm was vacuum evaporated on the electron transport layer as an electron injection layer; and an Al electrode layer with a thickness of 120 nm was vacuum evaporated on the electron injection layer as a cathode.

[0183]

[0184] [Device Examples 2-44]

[0185] Compounds 5, 64, 71, 73, 80, 83, 113, 123, 131, 211, 230, 248, 249, 294, 300, 333, 339, 346, 375, 363, 399, 443, 456, 464, 480, 492, 523, 530, 536, 552, 596, 635, 639, 658, 664, 683, 697, 724, 738, 837, 962, 1049, and 1050 of the present invention were used to replace compound 1 in device example 1 as the electron transport material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0186] [Comparative Device Examples 1-4]

[0187] Compounds Ref-1, Ref-2, Ref-3, and Ref-4 were used to replace compound 1 in device example 1 as electron transport materials. Otherwise, organic electroluminescent devices were prepared using the same preparation method as in device example 1.

[0188] The luminescence characteristics test results of devices 1-44 in the device embodiments of the present invention and the organic electroluminescent devices obtained in comparative embodiments 1-4 are shown in Table 1 below.

[0189] Table 1:

[0190]

[0191] As shown in Table 1, when the compound described in this invention is used as an electron transport material for organic electroluminescent devices, the device exhibits a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance electron transport material.

[0192] [Device Example 45]

[0193] First, a transparent conductive ITO glass substrate is used as the anode and ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0194] A hole injection layer with a thickness of 10 nm and a ratio of 99:1 (wt%) of HT-2:HI-2 was vacuum-deposited on an ITO glass substrate. A hole transport layer with a thickness of 110 nm and a thickness of HT-2 was vacuum-deposited on the hole injection layer. GH-1 as the first host material, GH-2 as the second host material, and GD-2 as the guest material (mass ratio 47:47:6) were vacuum-deposited on the hole transport layer, with a light-emitting layer thickness of 40 nm. Compound 1 was vacuum-deposited on the light-emitting layer to form a hole blocking layer with a thickness of 5 nm. ET-2 and Liq were vacuum-deposited on the hole blocking layer at a ratio of 1:1 (wt%) to form an electron transport layer with a thickness of 35 nm. LiF with a thickness of 0.8 nm was vacuum-deposited on the electron transport layer as an electron injection layer. An Al electrode layer with a thickness of 120 nm was vacuum-deposited on the electron injection layer as a cathode.

[0195]

[0196] [Device Examples 46-88]

[0197] Compounds 5, 64, 71, 73, 80, 83, 113, 123, 131, 211, 230, 248, 249, 294, 300, 333, 339, 346, 375, 363, 399, 443, 456, 464, 480, 492, 523, 530, 536, 552, 596, 635, 639, 658, 664, 683, 697, 724, 738, 837, 962, 1049, and 1050 of the present invention were used to replace compound 1 in device example 45 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 45.

[0198] [Comparative Device Examples 5-8]

[0199] Compounds Ref5, Ref6, Ref7, and Ref8 were used to replace compound 1 in device example 45 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 45.

[0200] The luminescence characteristics test results of devices 45-88 in the device embodiments of the present invention and those of organic electroluminescent devices obtained in comparative embodiments 5-8 are shown in Table 2 below.

[0201] Table 2:

[0202]

[0203] As shown in Table 2, when the compound described in this invention is used as a hole blocking material in organic electroluminescent devices, the devices exhibit lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance hole blocking material.

[0204] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A compound containing a bistriazine structure, characterized in that, The compound containing the bistriazine structure is shown in Formula 1. The Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups. The "substituted" groups in Ar1, Ar2, Ar3, and Ar4 are selected from any one of Formula 1-1, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings, and at least one of Ar1, Ar2, Ar3, and Ar4 comprises one or more of Formula 1-1; In Formula 1-1, Ra is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The La and Lb may be the same or different, and are independently selected from single bonds or any of the following structures: The a is independently selected from C(R1) or N; The b is independently selected from C(R2) or N, and at least one b is selected from N; The term e is independently selected from C(R3) or N; H1 is selected from O, S, C(R4)2 or N(R5); The ring A is selected from substituted or unsubstituted C3-C20 alicyclic rings; R1, R2, R3, and R5 may be the same or different, and are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloyl group of C3-C20 alicyclic and C3-C30 heteroaryl ring. The R4 and R6 may be the same or different, and are independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or substituted or unsubstituted rings formed by bonding two adjacent R6s; The L1, L2, L3, and L4 may be the same or different, and are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroarylene rings in a fused cycloalcoholic group.

2. The compound containing a bistriazine structure according to claim 1, characterized in that, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any of the following structures: The i is independently selected from C(R8) or N; The u is independently selected from C(R8′) or N; The P1 is selected from O, S, C(R9)2 or N(R) 10 ); P2 is selected from O, S, C(R) 11 )2 or N(R 12 ); The ring B is selected from substituted or unsubstituted C3-C20 alicyclic rings; The R8 and R8′ may be the same or different, and are independently selected from any one of the following: formula 1-1, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or two adjacent R8 and two adjacent R8′ are bonded to each other to form a substituted or unsubstituted ring; The R9, R 11 The same or different, independently selected from any one of the following: formula 1-1, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or two adjacent R 11 They bond with each other to form substituted or unsubstituted rings; The R 10 R 12 The same or different, independently selected from any one of the following: formula 1-1, hydrogen, deuterium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring.

3. The compound containing a bistriazine structure according to claim 1, characterized in that, Ar1, Ar2, Ar3, and Ar4 may be the same or different, and are independently selected from any of the following structures: R8 and R8′ are independently selected from formula 1-1, hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R9, R 11 The group is independently selected from formula 1-1, hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R 10 R 12 The group is independently selected from formula 1-1, hydrogen, deuterium, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, or 4; the n3 is selected from 0, 1, 2, or 3; the n4 is selected from 0, 1, or 2; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n6 is selected from 0, 1, 2, 3, 4, 5, or 6; the n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; n 11 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

4. The compound containing a bistriazine structure according to claim 1, characterized in that, The La and Lb may be the same or different, and are independently selected from single bonds or any of the following structures: ； R1 and R2 are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. The R1′ is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene. R3, R4, R5, and R6 are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, tetraphenyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiopheneyl. c1 is selected from 0, 1, 2, 3 or 4; c2 is selected from 0, 1, 2 or 3; c3 is selected from 0, 1 or 2; c4 is selected from 0, 1, 2, 3, 4 or 5; c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c7 is selected from 0, 1, 2, 3, 4, 5 or 6; c8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; c9 is selected from 0 or 1.

5. The compound containing a bis(triazine) structure according to claim 1, characterized in that, L1, L2, L3, and L4 may be the same or different, and are independently selected from single bonds or any of the following structures: The u is independently selected from C(Rb) or N; G1 is selected from O, S, C(Rc)2 or N(Rd); The G2 is selected from O, S, C(Re)2 or N(Rf); The ring C is independently selected from substituted or unsubstituted C3 to C20 alicyclic rings; The Rb, Rc, and Re are independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring, or any one of the following: two adjacent Rb and two adjacent Re are bonded together to form a substituted or unsubstituted ring. The Rd and Rf are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl ring.

6. The compound containing a bistriazine structure according to claim 1, characterized in that, Formula 1 is selected from one of the following structures: 。 7. An organic electroluminescent device, characterized in that, The organic electroluminescent device contains at least one of the compounds containing a bis(triazine) structure as described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains at least one of the compounds containing a bistriazine structure as described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the electron transport region contains at least one of the compounds containing a bistriazine structure as described in any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 9, characterized in that, The electron transport region comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the compounds containing a bistriazine structure as described in any one of claims 1 to 6.

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