Carbazole-containing compound and organic electroluminescent device thereof

Abstract

The invention provides a carbazole compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The carbazole-containing compound provided by the invention has proper molecular weight, relatively balanced evaporation temperature and refractive index, can inhibit loss of emergent light caused by total reflection, has good stability, can effectively improve and enhance light extraction efficiency when being applied to a covering layer material, and can improve luminous efficiency and service life of a device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are devices that emit light by causing carrier injection and recombination in organic materials through the action of an electric field. They can convert electrical energy into light energy and currently have a promising future, expanding into diverse fields such as laptops, monitors, televisions and other medium and large-sized devices, as well as wearable devices and automotive displays.

[0003] OLED devices are classified into bottom-emitting and top-emitting types according to their light emission path. Currently, top-emitting devices have superior application and performance, with better light extraction efficiency than bottom-emitting devices. By adding a capping layer outside the metal cathode, the loss of emitted light caused by total internal reflection can be suppressed, and the light trapped inside the device can be coupled out, thereby improving the luminous efficiency and lifespan of the device.

[0004] However, the current top-emitting OLED devices form a microcavity between the metal cathode and the bottom reflective layer, resulting in a strong dependence on the light emission angle. Furthermore, they exhibit poor stability, are prone to fluctuations in the evaporation process, and are susceptible to crystallization after coating, making it difficult to balance the evaporation temperature and refractive index. Therefore, developing a capping layer material that combines high stability, compatibility with evaporation processes, and simultaneous improvement in light extraction efficiency and viewing distortion has become a key and inevitable requirement for driving the technological upgrade of top-emitting OLED devices. Summary of the Invention

[0005] To address the issue of low performance in existing organic electroluminescent devices, this invention provides a carbazole-containing compound and its organic electroluminescent device.

[0006] This invention provides a carbazole-containing compound having the structure represented by Formula I:

[0007] The Ar0 is selected from formula II:

[0008] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1: ; X is selected from O or S; The v is independently selected from C(R2) or N, and at least one v is selected from an N atom; when v is bonded to other groups, the v is selected from a C atom. The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The Y is selected from O, S, or N (R0); The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms; The R0 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent R3s can be interconnected to form one or more substituted or unsubstituted rings; The R3' is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; The x is independently selected from C(R4) or N, and when x is bonded to other groups, the x is selected from C atoms; The R4 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted rings; The Ar is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; L1, L2, and L3 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-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0009] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the carbazole-containing compounds.

[0010] Beneficial effects: This invention provides a carbazole-containing compound with a suitable molecular weight, a relatively balanced evaporation temperature and refractive index, which can suppress the loss of emitted light caused by total internal reflection, and has good stability. When applied to capping materials, it can effectively improve and enhance light extraction efficiency, thereby improving the luminous efficiency and lifespan of the device. Detailed Implementation

[0011] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0012] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0013] In this specification, " "This refers to the portion that is connected to another substituent."

[0014] 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.

[0015] 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 rings. For example, Can represent or ; Can represent , , And so on.

[0016] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0017] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0018] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0019] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl or aryl group, preferably substituted with 3 alkyl or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C3-C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.

[0020] The aryl group described in this invention refers to a monovalent group obtained by 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.

[0021] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 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. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0022] The alicyclic hydrocarbons described in this invention refer to cyclic hydrocarbons with aliphatic properties, containing closed carbon rings in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 12 carbon atoms, and more preferably 3 to 7 carbon atoms. They can form monocyclic or polycyclic hydrocarbons, and can be saturated or unsaturated alicyclic hydrocarbons. The alicyclic hydrocarbons can be substituted or unsubstituted. Examples of saturated alicyclic hydrocarbons include cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane, while examples of unsaturated alicyclic hydrocarbons include cyclopropylene, cyclobutene, cyclopentene, cyclohexene, and cycloheptene, but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0023] The fused alicyclic and aromatic ring groups described in this invention refer to rings containing one or more aromatic rings and one or more alicyclic rings fused together by sharing two adjacent carbon atoms. The aromatic rings preferably have 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The alicyclic rings preferably have 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused alicyclic and aromatic ring groups can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0024] The arylene group described in this invention refers to the general 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 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, phenanthrene, etc., but are not limited to these.

[0025] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.

[0026] The fused alicyclic and aromatic ring groups described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linking sites, i.e., divalent groups. Apart from being divalent groups, they are similar to the fused ring groups of aromatic and aliphatic rings described above.

[0027] The fused ring groups of aromatic and aliphatic rings described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linking sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the fused ring groups of aromatic and aliphatic rings described above.

[0028] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0029] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from any of the following: deuterium, cyano, fluorine, halogen atom, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused rings of substituted or unsubstituted C6-C30 aromatic rings and C3-C30 aliphatic rings. One preferred group includes deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 silyl, C6-C30 aryl, and C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and adamantyl. Norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, phenyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane Benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyrroleyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0030] 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: .

[0031] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.

[0032] This invention provides a carbazole-containing compound having the structure represented by Formula I:

[0033] The Ar0 is selected from formula II:

[0034] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1: ; X is selected from O or S; The v is independently selected from C(R2) or N, and at least one v is selected from an N atom; when v is bonded to other groups, the v is selected from a C atom. The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The Y is selected from O, S, or N (R0); The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms; The R0 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent R3s can be interconnected to form one or more substituted or unsubstituted rings; The R3' is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; The x is independently selected from C(R4) or N, and when x is bonded to other groups, the x is selected from C atoms; The R4 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted rings; The Ar is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; L1, L2, and L3 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-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0035] Preferably, the Ar0 is selected from any one of the following groups:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] The v is independently selected from C(R2) or N, and one, two, three, four, five or six v are selected from N, while the rest are selected from C(R2). When v is bonded to other groups, the v is selected from C atoms. The R2 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene.

[0043] Preferably, the Ar0 is selected from any one of the following groups:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] The number b0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b1 is selected from 0, 1, or 2; the number b2 is selected from 0, 1, 2, or 3; the number b3 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b4 is selected from 0, 1, 2, 3, 4, or 5; the number b5 is selected from 0, 1, 2, 3, or 4; the number b6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the number b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0095] Preferably, the Selected from any one of the following groups:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The R3 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent R3s may be linked together to form one or more substituted or unsubstituted rings; The R3' is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The R0 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiophene. p0 is selected from 0, 1, 2, 3 or 4; p1 is selected from 0, 1, 2 or 3; p2 is selected from 0, 1 or 2; p3 is selected from 0, 1, 2, 3, 4, 5 or 6; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0106] Preferably, the Selected from any one of the following groups:

[0107] X1 is selected from O, S, C (ReRf) or N (Rg); The x is independently selected from C(R4), or in each group, one, two, three, four, five, or six x are selected from N, and the rest are selected from C(R4). When x is bonded to other groups, the x is selected from C atoms. The R4 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rg is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Re and Rf are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. adamantyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or Re and Rf can be interconnected to form one or more substituted or unsubstituted rings.

[0108] Preferably, the Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, or any one of the following groups:

[0109]

[0110]

[0111] The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; W1 is selected from O, S or N (Rz); Q1 is selected from O, S, N (Rz) or C (RxRy); The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings; The Rd1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2.

[0112] Preferably, the Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, or any of the groups selected from the following:

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The t is independently selected from CH, or one, two or three ts in each group are selected from N, and the rest are selected from CH. When t is bonded to other groups, the t is selected from C atoms. The Rz is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd1 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings; The Rx and Ry are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 10 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0134] Preferably, L1, L2, and L3 are independently selected from single bonds or any of the following groups and combinations thereof:

[0135]

[0136] The u is independently selected from CH or N, and when u is bonded to other groups, the u is selected from C atoms; The T is selected from O, S, N (Rw) or C (RhRi); The Rw is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl; The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rh and Ri are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rh and Ri can be connected to each other to form substituted or unsubstituted rings; The Rm is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0137] Preferably, L1, L2, and L3 are independently selected from single bonds or any of the following groups and combinations thereof:

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] The Rw is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rm is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 0, 1, 2, 3, 4 or 5.

[0144] Preferably, the carbazole-containing compound is selected from any one of the following structures:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462] .

[0463] The above lists some specific structural forms of carbazole-containing compounds represented by Formula I of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, with substituents as defined above, should be included.

[0464] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the carbazole-containing compounds described in the present invention.

[0465] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport region.

[0466] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0467] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0468] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0469] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0470] Preferably, the organic functional layer is located outside either the anode or the cathode electrode, and the organic functional layer includes a capping layer, which contains any one or more of the carbazole-containing compounds described in this invention.

[0471] 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 organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc.

[0472] The anode material described in this invention preferably uses a material with a high energy function, which improves hole injection efficiency. The anode material that can be used in this invention is selected from the following: indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof, 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 multilayer 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 is not limited thereto.

[0473] The hole injection layer described in this invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used in the hole injection layer of this invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, phenazine compounds, etc., but are not limited thereto.

[0474] The hole transport layer material described in this invention is preferably a material with high hole mobility. It can be selected from any one or more of the following structures: 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-2-yl)-N,N'-di(phenyl)biphenyl-4,4'-diamine (β-NPB), carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, anthraquinone compounds, polyaniline, polythiophene, etc., but is not limited thereto.

[0475] The electron blocking layer material described in this invention is preferably a material that has the property of preventing electrons from passing through the light-emitting layer. Specific examples may include materials such as triarylamine derivatives, spirofluorene derivatives, furan derivatives, etc., such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), but are not limited thereto.

[0476] The light-emitting layer material of this invention includes a host material and a dopant material. The host material of the light-emitting layer needs to have bipolar charge transport properties and suitable energy levels, and is selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 9,10-bis(1-naphthyl)anthracene (α-AND), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(9-carbazoleyl)benzene (TCP), etc., or the carbazole-containing compounds of this invention, but are not limited thereto.

[0477] The light-emitting layer doping materials of this invention are classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials. The light-emitting layer doping materials can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials, selected from, but not limited to, 2,5,8,11-tetratert-butylperylene (TBPe), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenylisoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)).

[0478] The hole blocking layer of this invention preferably uses a material with strong hole blocking capability and suitable HOMO / LUMO energy levels. The hole blocking layer material of this invention can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0479] The electron transport layer material described in this invention is preferably a material with high electron mobility. It can be selected from any one or more of the following structures: tris(8-hydroxyquinoline)aluminum(III) (Alq3), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but is not limited thereto.

[0480] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, 8-hydroxyquinoline cesium), organometallic salts (metal acetate, metal benzoate or metal stearate), molybdenum trioxide, aluminum, etc., but are not limited thereto.

[0481] The cathode material of this invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. It can be selected from any one or more of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0482] The capping layer of this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the internal optical coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., or carbazole-containing compounds as described in this invention, but are not limited thereto.

[0483] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0484] The organic electroluminescent device of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.

[0485] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0486] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0487] This invention provides a method for preparing compounds represented by Formula I, which is carried out through carbon-nitrogen coupling and carbon-carbon coupling reactions well known in the art. However, the preparation method of this invention is not limited to this, and the structure of Formula I can be prepared by the reaction route shown below: 1. Preparation of intermediate c:

[0488] 2. Preparation of Formula I:

[0489] Among them, Xa, Xb, Xc, and Xd may be the same or different from each other, and are selected from any one of Cl, Br, and I; the limitations of Y, Ar, Ar0, L1, L2, L3, R3', x, and z are the same as those described above.

[0490] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0491] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0492] Preparation and characterization of compounds

[0493] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.

[0494] 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-1

[0495] Preparation of intermediate E-60: Under nitrogen protection, e-60 (55.81 g, 220.00 mmol), B2Pin2 (60.94 g, 240.00 mmol), K2CO3 (60.82 g, 440.00 mmol), Pd(PPh3)4 (3.00 g, 2.60 mmol), and DMF (1000 mL) were added to the reaction flask, and the reaction mixture was heated to reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand and separated, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from toluene:ethanol = 10:1 and dried to obtain intermediate E-60 (62 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 345.1544 (theoretical value: 345.1536).

[0496] Preparation of intermediate C-60

[0497] Under nitrogen protection, starting materials E-60 (27.62 g, 80.00 mmol), f-60 (15.64 g, 80.00 mmol), K2CO3 (22.11 g, 160.00 mmol), and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air with nitrogen three times, Pd(PPh3)4 (1.11 g, 0.96 mmol) was added. The mixture was stirred and heated under reflux for 5.0 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol in a 5:1 ratio to obtain intermediate c-60 (20.30 g), with an HPLC purity ≥99.84%. Mass spectrometry m / z: 333.0870 (theoretical value: 333.0858).

[0498] Other intermediates required for the present invention were synthesized using the above-described synthesis method. The relevant raw materials are shown in Table 1. Table 1:

[0499] Synthesis Example 2: Preparation of Compound 1

[0500] Preparation of intermediate A-1: Under nitrogen protection, starting material b-1 (19.50 g, 60 mmol), starting material a-1 (29.41 g, 120 mmol), and Pd(OAc)2 (0.33 g, 1.48 mmol) were added to DMF (415 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (38.21 g, 180 mmol) was added, and the mixture was heated under reflux for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate A-1 (20.47 g), with an HPLC purity of ≥99.69%. Mass spectrometry m / z: 401.1152 (theoretical value: 401.1164).

[0501] Preparation of compound 1: Under nitrogen protection, intermediates A-1 (20.07 g, 50 mmol), e-60 (12.68 g, 50 mmol), and sodium tert-butoxide (11.92 g, 124 mmol) were added to 300 mL of toluene. Pd2(dba)3 (0.38 g, 0.42 mmol) and P(t-Bu)3 (3.69 mL of 0.5 M toluene solution, 0.84 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 10 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The obtained solid was recrystallized from toluene to give compound 1 (23.20 g), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 618.1677 (theoretical value: 618.1692). Theoretical element content (%) C 41 H 22 N4O3: C, 79.60; H, 3.58; N, 9.06. Measured elemental content (%): C, 79.62; H, 3.56; N, 9.09.

[0502] Synthesis Example 3: Preparation of Compound 17

[0503] According to the preparation method in Synthesis Example 2, e-60 was replaced with an equimolar amount of c-17 to obtain compound 17 (23.20 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 618.1688 (theoretical value: 618.1692). Theoretical elemental content (%) C 41 H 22N4O3: C, 79.60; H, 3.58; N, 9.06. Measured elemental content (%): C, 79.57; H, 3.59; N, 9.08.

[0504] Synthesis Example 4: Preparation of Compound 25

[0505] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-25, and e-60 was replaced with an equimolar amount of c-25 to obtain compound 25 (25.05 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 770.2300 (theoretical value: 770.2318). Theoretical elemental content (%) C 53 H 30 N4O3: C, 82.58; H, 3.92; N, 7.27. Measured elemental content (%): C, 82.59; H, 3.95; N, 7.25.

[0506] Synthesis Example 5: Preparation of Compound 27

[0507] According to the preparation method in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-27, and e-60 was replaced with an equimolar amount of c-27 to obtain compound 27 (23.51 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 618.1678 (theoretical value: 618.1692). Theoretical elemental content (%) C 41 H 22 N4O3: C, 79.60; H, 3.58; N, 9.06. Measured elemental content (%): C, 79.58; H, 3.57; N, 9.04.

[0508] Synthesis Example 6: Preparation of Compound 60

[0509] According to the preparation method in Synthesis Example 2, e-60 was replaced with an equimolar amount of c-60 to obtain compound 60 (24.81 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 698.2244 (theoretical value: 698.2256). Theoretical elemental content (%) C 47 H 22 D4N4O3: C, 80.79; H, 4.33; N, 8.02. Measured elemental content (%): C, 80.76; H, 4.35; N, 8.05.

[0510] Synthesis Example 7: Preparation of Compound 71

[0511] According to the preparation method in Synthesis Example 2, e-60 was replaced with an equimolar amount of c-71 to obtain compound 71 (24.33 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 695.1943 (theoretical value: 695.1957). Theoretical elemental content (%) C 46 H 25 N5O3: C, 79.41; H, 3.62; N, 10.07. Measured elemental content (%): C, 79.43; H, 3.60; N, 10.09.

[0512] Synthesis Example 8: Preparation of Compound 85

[0513] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-86 to obtain compound 85 (25.82 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 770.2300 (theoretical value: 770.2318). Theoretical elemental content (%) C 53 H 30 N4O3: C, 82.58; H, 3.92; N, 7.27. Measured elemental content (%): C, 82.56; H, 3.90; N, 7.28.

[0514] Synthesis Example 9: Preparation of Compound 91

[0515] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-91 to obtain compound 91 (26.09 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 778.2800 (theoretical value: 778.2820). Theoretical elemental content (%) C 53 H 22 D8N4O3: C, 81.73; H, 4.92; N, 7.19. Measured elemental content (%): C, 81.71; H, 4.90; N, 7.18.

[0516] Synthesis Example 10: Preparation of Compound 100

[0517] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-100 to obtain compound 100 (27.44 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 870.2612 (theoretical value: 870.2631). Theoretical elemental content (%) C 61 H 34 N4O3: C, 84.12; H, 3.93; N, 6.43. Measured elemental content (%): C, 84.10; H, 3.91; N, 6.45.

[0518] Synthesis Example 11: Preparation of Compound 101

[0519] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-101 to obtain compound 101 (26.66 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 772.2201 (theoretical value: 772.2223). Theoretical elemental content (%) C 51 H 28 N6O3: C, 79.26; H, 3.65; N, 10.87. Measured elemental content (%): C, 79.27; H, 3.63; N, 10.87.

[0520] Synthesis Example 12: Preparation of Compound 107

[0521] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-86, b-1 with an equimolar amount of b-107, and e-60 with an equimolar amount of c-107, yielding compound 107 (26.98 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 770.2302 (theoretical value: 770.2318). Theoretical elemental content (%) C 53 H 30 N4O3: C, 82.58; H, 3.92; N, 7.27. Measured elemental content (%): C, 82.56; H, 3.91; N, 7.29.

[0522] Synthetic Example 13: Preparation of Compound 115

[0523] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-115 to obtain compound 115 (24.20 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 620.1578 (theoretical value: 620.1597). Theoretical elemental content (%) C 39 H 20 N6O3: C, 75.48; H, 3.25; N, 13.54. Measured elemental content (%): C, 75.45; H, 3.26; N, 13.55.

[0524] Synthetic Example 14: Preparation of Compound 145

[0525] According to the preparation method in Example 2, a-1 was replaced with an equimolar amount of a-145 to obtain compound 145 (26.24 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 718.2023 (theoretical value: 718.2005). Theoretical elemental content (%) C 49 H 26 N4O3: C, 81.88; H, 3.65; N, 7.79. Measured elemental content (%): C, 81.89; H, 3.66; N, 7.77.

[0526] Synthetic Example 15: Preparation of Compound 156

[0527] According to the preparation method in Example 2, a-1 was replaced with an equimolar amount of a-156 to obtain compound 156 (29.13 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 970.2932 (theoretical value: 970.2944). Theoretical elemental content (%) C 69 H 38 N4O3: C, 85.34; H, 3.94; N, 5.77. Measured elemental content (%): C, 85.32; H, 3.95; N, 5.75.

[0528] Synthesis Example 16: Preparation of Compound 209

[0529] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-209 to obtain compound 209 (27.87 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 870.2611 (theoretical value: 870.2631). Theoretical elemental content (%) C61 H 34 N4O3: C, 84.12; H, 3.93; N, 6.43. Measured elemental content (%): C, 84.15; H, 3.91; N, 6.40.

[0530] Synthesis Example 17: Preparation of Compound 275

[0531] According to the preparation method in Synthesis Example 2, e-60 was replaced with an equimolar amount of c-275 to obtain compound 275 (26.08 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 668.1832 (theoretical value: 668.1848). Theoretical elemental content (%) C 45 H 24 N4O3: C, 80.83; H, 3.62; N, 8.38. Measured elemental content (%): C, 80.82; H, 3.62; N, 8.37.

[0532] Synthesis Example 18: Preparation of Compound 283

[0533] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-283, and e-60 was replaced with an equimolar amount of c-283, yielding compound 283 (26.45 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 669.1819 (theoretical value: 669.1801). Theoretical elemental content (%) C 44 H 23 N5O3: C, 78.91; H, 3.46; N, 10.46. Measured elemental content (%): C, 78.94; H, 3.42; N, 10.45.

[0534] Synthesis Example 19: Preparation of Compound 337

[0535] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-337, and e-60 was replaced with an equimolar amount of c-337, yielding compound 337 (27.58 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 776.1718 (theoretical value: 776.1705). Theoretical elemental content (%) C 51 H 28N4OS2: C, 78.84; H, 3.63; N, 7.21. Measured elemental content (%): C, 78.86; H, 3.65; N, 7.22.

[0536] Synthesis Example 20: Preparation of Compound 338

[0537] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-337, and e-60 was replaced with an equimolar amount of c-338, yielding compound 338 (27.62 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 777.1639; theoretical value: (777.1657). Theoretical elemental content (%) C 50 H 27 N5OS2: C, 77.20; H, 3.50; N, 9.00. Measured elemental content (%): C, 77.21; H, 3.51; N, 9.02.

[0538] Synthesis Example 21: Preparation of Compound 372

[0539] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-372 to obtain compound 372 (25.69 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 658.1754 (theoretical value: 658.1737). Theoretical elemental content (%) C 41 H 14 D8N4OS2: C, 74.75; H, 4.59; N, 8.50. Measured elemental content (%): C, 74.76; H, 4.59; N, 8.51.

[0540] Synthesis Example 22: Preparation of Compound 428

[0541] According to the preparation method in Synthesis Example 2, e-60 was replaced with an equimolar amount of c-428 to obtain compound 428 (25.59 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 710.1765 (theoretical value: 710.1776). Theoretical elemental content (%) C 47 H 26 N4O2S: C, 79.42; H, 3.69; N, 7.88. Measured elemental content (%): C, 79.41; H, 3.66; N, 7.89.

[0542] Synthesis Example 23: Preparation of Compound 596

[0543] Preparation of intermediate A-596: Under nitrogen protection, starting material a-1 (17.16 g, 70 mmol), starting material b-596 (17.23 g, 70 mmol), and Pd(OAc)2 (0.29 g, 1.29 mmol) were added to DMF (378 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (34.18 g, 161 mmol) was added, and the mixture was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate A-596 (14.93 g), with an HPLC purity of ≥99.66%. Mass spectrometry m / z: 284.0932 (theoretical value: 284.0950).

[0544] Preparation of compound 596: Under nitrogen protection, intermediates A-596 (14.22 g, 50 mmol), e-60 (12.68 g, 50 mmol), and sodium tert-butoxide (11.99 g, 124.74 mmol) were added to 311 mL of toluene. Pd2(dba)3 (0.38 g, 0.42 mmol) and P(t-Bu)3 (1.68 mL of 0.5 M toluene solution, 0.84 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 10 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was then carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 596 (17.55 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 501.1465 (theoretical value: 501.1477). Theoretical elemental content (%) C 34 H 19 N3O2: C, 81.42; H, 3.82; N, 8.38. Measured elemental content (%): C, 81.45; H, 3.80; N, 8.37.

[0545] Synthesis Example 24: Preparation of Compound 636

[0546] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-636, b-1 was replaced with an equimolar amount of b-636, and e-60 was replaced with an equimolar amount of c-636, yielding compound 636 (24.21 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 645.1650 (theoretical value: 645.1664). Theoretical elemental content (%) C 41 H 22 F3N3O2: C, 76.27; H, 3.43N, 6.51. Measured elemental content (%): C, 76.25; H, 3.40N, 6.50.

[0547] Synthesis Example 25: Preparation of Compound 663

[0548] Preparation of intermediate A-663: Under nitrogen protection, starting material a-1 (29.41 g, 120 mmol), starting material b-663 (33.67 g, 120 mmol), and Pd(OAc)2 (0.27 g, 1.20 mmol) were added to DMF (1060 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (38.21 g, 180 mmol) was added, and the mixture was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate A-663 (30.60 g), with an HPLC purity of ≥99.62%. Mass spectrometry m / z: 318.0540 (theoretical value: 318.0560).

[0549] Preparation of intermediate B-663: Under nitrogen protection, starting materials A-663 (25.50 g, 80 mmol), d-663 (23.52 g, 80 mmol), and Pd(OAc)2 (0.18 g, 0.80 mmol) were added to DMF (520 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (25.47 g, 120 mmol) was added, and the mixture was heated under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was cooled to crystallize, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate B-663 (27.02 g), with an HPLC purity of ≥99.75%. Mass spectrometry m / z: 450.0776 (theoretical value: 450.0792).

[0550] Preparation of compound 663: Under nitrogen protection, intermediates B-663 (22.52 g, 50 mmol), e-60 (12.68 g, 50 mmol), and sodium tert-butoxide (7.30 g, 76 mmol) were added to 111 mL of toluene. Pd2(dba)3 (0.46 g, 0.50 mmol) and P(t-Bu)3 (1.16 mL of 0.5 M toluene solution, 0.58 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 8 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 663 (23.03 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 667.1300 (theoretical value: 667.1319). Theoretical element content (%) C 40 H 18 F5N3O2: C, 71.97; H, 2.72; N, 6.29. Measured elemental content (%): C, 71.98; H, 2.70; N, 6.28.

[0551] Synthesis Example 26: Preparation of Compound 686

[0552] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-686, and e-60 was replaced with an equimolar amount of c-686, yielding compound 686 (25.08 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 668.2200 (theoretical value: 668.2212). Theoretical elemental content (%) C 46 H 28 N4O2: C, 82.62; H, 4.22; N, 8.38. Measured elemental content (%): C, 82.60; H, 4.25; N, 8.35.

[0553] Synthesis Example 27: Preparation of Compound 689

[0554] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-689 to obtain compound 689 (23.23 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 627.1950 (theoretical value: 627.1947). Theoretical elemental content (%) C 44 H 25N3O2: C, 84.19; H, 4.01; N, 6.69. Measured elemental content (%): C, 84.18; H, 4.00; N, 6.67.

[0555] Synthesis Example 28: Preparation of Compound 705

[0556] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-705 to obtain compound 705 (25.42 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 677.2125 (theoretical value: 677.2103). Theoretical elemental content (%) C 48 H 27 N3O2: C, 85.06; H, 4.02; N, 6.20. Measured elemental content (%): C, 85.05; H, 4.04; N, 6.22.

[0557] Synthesis Example 29: Preparation of Compound 714

[0558] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-714 to obtain compound 714 (25.08 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 677.2121 (theoretical value: 677.2103). Theoretical elemental content (%) C 48 H 27 N3O2: C, 85.06; H, 4.02; N, 6.20. Measured elemental content (%): C, 85.05; H, 4.00; N, 6.22.

[0559] Synthesis Example 30: Preparation of Compound 841

[0560] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-841 to obtain compound 841 (25.04 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 667.1887 (theoretical value: 667.1896). Theoretical elemental content (%) C 46 H 25 N3O3: C, 82.74; H, 3.77; N, 6.29. Measured elemental content (%): C, 82.73; H, 3.75; N, 6.28.

[0561] Synthesis Example 31: Preparation of Compound 865

[0562] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-865 to obtain compound 865 (27.28 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 717.2041 (theoretical value: 717.2052). Theoretical elemental content (%) C 50 H 27 N3O3: C, 83.67; H, 3.79; N, 5.85. Measured elemental content (%): C, 83.66; H, 3.79; N, 5.86.

[0563] Synthesis Example 32: Preparation of Compound 905

[0564] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-905 to obtain compound 905 (24.20 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 628.1887 (theoretical value: 628.1899). Theoretical elemental content (%) C 43 H 24 N4O2: C, 82.15; H, 3.85; N, 8.91. Measured elemental content (%): C, 82.15; H, 3.84; N, 8.92.

[0565] Synthesis Example 33: Preparation of Compound 939

[0566] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-939 to obtain compound 939 (24.40 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 633.1523 (theoretical value: 633.1511). Theoretical elemental content (%) C 42 H 23 N3O2S: C, 79.60; H, 3.66; N, 6.63. Measured elemental content (%): C, 79.60; H, 3.64; N, 6.62.

[0567] Synthesis Example 34: Preparation of Compound 1064

[0568] Following the preparation method of Synthesis Example 25, a-1 was replaced with an equimolar amount of a-86, and d-663 was replaced with an equimolar amount of d-1064, yielding compound 1064 (26.53 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 803.2565 (theoretical value: 803.2573). Theoretical elemental content (%) C 58 H 33 N3O2: C, 86.66; H, 4.14; N, 5.23. Measured elemental content (%): C, 86.64; H, 4.14; N, 5.22.

[0569] Synthesis Example 35: Preparation of Compound 1071

[0570] Following the preparation method of Synthesis Example 25, a-1 was replaced with an equimolar amount of a-1071, and d-663 was replaced with an equimolar amount of d-1071, yielding compound 1071 (27.33 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 803.2566 (theoretical value: 803.2573). Theoretical elemental content (%) C 58 H 33 N3O2: C, 86.66; H, 4.14; N, 5.23. Measured elemental content (%): C, 86.68; H, 4.15; N, 5.22.

[0571] Synthesis Example 36: Preparation of Compound 1173

[0572] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of d-1173 to obtain compound 1173 (23.20 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 618.1675 (theoretical value: 618.1692). Theoretical elemental content (%) C 41 H 22 N4O3: C, 79.60; H, 3.58; N, 9.06. Measured elemental content (%): C, 79.62; H, 3.57; N, 9.05.

[0573] Synthesis Example 37: Preparation of Compound 1231

[0574] Following the preparation method of Synthesis Example 25, a-1 was replaced with an equimolar amount of a-1231, and d-663 was replaced with an equimolar amount of d-1231, yielding compound 1231 (23.37 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 591.1932 (theoretical value: 591.1947). Theoretical elemental content (%) C 41 H 25 N3O2: C, 83.23; H, 4.26; N, 7.10. Measured elemental content (%): C, 83.23; H, 4.25; N, 7.13.

[0575] Synthesis Example 38: Preparation of Compound 1232

[0576] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-86, and b-596 was replaced with an equimolar amount of b-1232, yielding compound 1232 (23.85 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 627.1928 (theoretical value: 627.1947). Theoretical elemental content (%) C 44 H 25 N3O2: C, 84.19; H, 4.01; N, 6.69. Measured elemental content (%): C, 84.17; H, 4.00; N, 6.68.

[0577] Synthesis Example 39: Preparation of Compound 1233

[0578] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-86, and b-596 was replaced with an equimolar amount of b-1233, yielding compound 1233 (26.74 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 742.2345 (theoretical value: 742.2369). Theoretical elemental content (%) C 52 H 30 N4O2: C, 84.08; H, 4.07; N, 7.54. Measured elemental content (%): C, 84.06; H, 4.08; N, 7.52.

[0579] Synthesis Example 40: Preparation of Compound 1365

[0580] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-337, b-596 was replaced with an equimolar amount of b-1365, and e-60 was replaced with an equimolar amount of c-1365, yielding compound 1365 (24.37 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 649.2176 (theoretical value: 649.2188). Theoretical elemental content (%) C 44 H 31 N3OS: C, 81.33; H, 4.81; N, 6.47. Measured elemental content (%): C, 81.32; H, 4.80; N, 6.45.

[0581] Synthesis Example 41: Preparation of Compound 1371

[0582] Following the preparation method of Synthesis Example 25, a-1 was replaced with an equimolar amount of a-337, d-663 with an equimolar amount of d-1371, and e-60 with an equimolar amount of c-1365, yielding compound 1371 (27.08 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 741.2287 (theoretical value: 741.2270). Theoretical elemental content (%) C 49 H 35 N3OSSi: C, 79.32; H, 4.75; N, 5.66. Measured elemental content (%): C, 79.30; H, 4.75; N, 5.64.

[0583] Synthesis Example 42: Preparation of Compound 1372

[0584] According to the preparation method in Synthesis Example 25, a-1 was replaced with an equimolar amount of a-337, d-663 was replaced with an equimolar amount of d-1372, and e-60 was replaced with an equimolar amount of c-1365, yielding compound 1372 (27.34 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 803.2988 (theoretical value: 803.2970). Theoretical elemental content (%) C 56 H 41 N3OS: C, 83.66; H, 5.14; N, 5.23. Measured elemental content (%): C, 83.66; H, 5.12; N, 5.22.

[0585] Synthesis Example 43: Preparation of Compound 1408

[0586] Following the preparation method of Synthesis Example 25, a-1 was replaced with an equimolar amount of a-337, d-663 with an equimolar amount of d-1408, and e-60 with an equimolar amount of c-1365, yielding compound 1408 (27.79 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 793.2167 (theoretical value: 793.2188). Theoretical elemental content (%) C 56 H 31 N3OS: C, 84.72; H, 3.94; N, 5.29. Measured elemental content (%): C, 84.70; H, 3.96; N, 5.27.

[0587] Synthesis Example 44: Preparation of Compound 1410

[0588] According to the preparation method in Synthesis Example 25, a-1 was replaced with an equimolar amount of a-337, d-663 was replaced with an equimolar amount of d-1410, and e-60 was replaced with an equimolar amount of c-1410, yielding compound 1410 (28.80 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 885.2258 (theoretical value: 885.2272). Theoretical elemental content (%) C 62 H 35 N3S2: C, 84.04; H, 3.98; N, 4.74. Measured elemental content (%): C, 84.05; H, 3.99; N, 4.72.

[0589] Synthetic Example 45: Preparation of Compound 1474

[0590] Following the preparation method of Synthesis Example 25, d-663 was replaced with an equimolar amount of a-337, and e-60 was replaced with an equimolar amount of c-428, yielding compound 1474 (27.26 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 726.1533 (theoretical value: 726.1548). Theoretical elemental content (%) C 47 H 26 N4OS2: C, 77.66; H, 3.61; N, 7.71. Measured elemental content (%): C, 77.67; H, 3.60; N, 7.70.

[0591] Synthesis Example 46: Preparation of Compound 1533

[0592] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-1533, and b-596 was replaced with an equimolar amount of b-1533, yielding compound 1533 (26.33 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 683.1652 (theoretical value: 683.1667). Theoretical elemental content (%) C 46 H 25 N3O2S: C, 80.80; H, 3.69; N, 6.15. Measured elemental content (%): C, 80.80; H, 3.67; N, 6.12.

[0593] Synthesis Example 47: Preparation of Compound 1546

[0594] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-1533, b-596 was replaced with an equimolar amount of b-1546, and e-60 was replaced with an equimolar amount of e-428, yielding compound 1546 (23.44 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 616.1759 (theoretical value: 616.1773). Theoretical elemental content (%) C 40 H 16 D7N3S2: C, 77.89; H, 4.90; N, 6.81. Measured elemental content (%): C, 77.89; H, 4.92; N, 6.80.

[0595] Synthesis Example 48: Preparation of Compound 1547

[0596] According to the preparation method in Synthesis Example 23, a-1 was replaced with an equimolar amount of a-1533, b-596 was replaced with an equimolar amount of b-1547, and e-60 was replaced with an equimolar amount of e-428, yielding compound 1547 (23.82 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 610.1267 (theoretical value: 610.1286). Theoretical elemental content (%) C 39 H 22 N4S2: C, 76.70; H, 3.63; N, 9.17. Measured elemental content (%): C, 76.72; H, 3.60; N, 9.15.

[0597] Synthesis Example 49: Preparation of Compound 1794

[0598] According to the preparation method in Synthesis Example 25, a-1 was replaced with an equimolar amount of a-1794, d-663 was replaced with an equimolar amount of d-1794, and e-60 was replaced with an equimolar amount of c-1365, yielding compound 1794 (28.81 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 834.2434 (theoretical value: 834.2453). Theoretical elemental content (%) C 58 H 34 N4OS: C, 83.43; H, 4.10; N, 6.71. Measured elemental content (%): C, 83.45; H, 4.12; N, 6.70.

[0599] Device Examples

[0600] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0601] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 10 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime of the device prepared in this invention (brightness decaying to 95% of initial brightness) was tested at atmospheric pressure and room temperature, with a test current density of 10 mA / cm². 2 .

[0602] [Device Example 1]

[0603] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0604] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate. The following layers were deposited sequentially: hole injection layer HI-1 (10 nm); hole transport layer HT-1 (120 nm); light-emitting layer GH-1:GD-1=48:48:4 (mass ratio, 30 nm); electron transport layer ET-1:Liq=1:1 (mass ratio, 40 nm); electron injection layer LiF (0.8 nm); cathode Mg:Ag=1:9 (mass ratio, 10 nm); and capping layer compound 1 (90 nm).

[0605]

[0606] [Device Examples 2-48]

[0607] Compounds 17, 25, 27, 60, 71, 85, 91, 100, 101, 107, 115, 145, 156, 209, 275, 283, 337, 338, 372, 428, 596, 636, 663, 686, 689, 705, 714, 841, and 865 of this invention are used. Compounds 905, 939, 1064, 1071, 1173, 1231, 1232, 1233, 1365, 1371, 1372, 1408, 1410, 1474, 1533, 1546, 1547, and 1794 were used to replace compound 1 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0608] [Comparative Device Examples 1-4]

[0609] Comparative compounds 1, 2, 3, and 4 were used to replace compound 1 in device example 1 as the capping material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0610] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 1-48 and Comparative Examples 1-4 are shown in Table 2 below.

[0611]

[0612]

[0613] As can be seen from the data in Table 2, the application of the carbazole-containing compound described in this invention as a capping material in organic electroluminescent devices exhibits good light extraction efficiency and thermal stability, resulting in excellent luminous efficiency and lifespan for the device.

[0614] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A carbazole-containing compound, characterized in that, The carbazole-containing compound has the structure represented by Formula I: The Ar0 is selected from formula II: Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1: ; X is selected from O or S; The v is independently selected from C(R2) or N, and at least one v is selected from an N atom; when v is bonded to other groups, the v is selected from a C atom. The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The Y is selected from O, S, or N (R0); The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms; The R0 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent R3s can be interconnected to form one or more substituted or unsubstituted rings; The R3' is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; The x is independently selected from C(R4) or N, and when x is bonded to other groups, the x is selected from C atoms; The R4 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent R4s can be interconnected to form one or more substituted or unsubstituted rings; The Ar is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; L1, L2, and L3 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-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

2. The carbazole-containing compound according to claim 1, characterized in that, The Ar0 is selected from any one of the following groups: The v is independently selected from C(R2) or N, and one, two, three, four, five or six v are selected from N, while the rest are selected from C(R2). When v is bonded to other groups, the v is selected from C atoms. The R2 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene.

3. The carbazole-containing compound according to claim 1, characterized in that, The Selected from any one of the following groups: The R3 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent R3s may be linked together to form one or more substituted or unsubstituted rings; The R3' is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The R0 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiophene. p0 is selected from 0, 1, 2, 3 or 4; p1 is selected from 0, 1, 2 or 3; p2 is selected from 0, 1 or 2; p3 is selected from 0, 1, 2, 3, 4, 5 or 6; p4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

4. The carbazole-containing compound according to claim 1, characterized in that, The Selected from any one of the following groups: X1 is selected from O, S, C (ReRf) or N (Rg); The x is independently selected from C(R4), or in each group, one, two, three, four, five, or six x are selected from N, and the rest are selected from C(R4). When x is bonded to other groups, the x is selected from C atoms. The R4 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rg is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Re and Rf are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. adamantyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or Re and Rf can be interconnected to form one or more substituted or unsubstituted rings.

5. The carbazole-containing compound according to claim 1, characterized in that, The Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, or any one of the following groups: The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; W1 is selected from O, S or N (Rz); Q1 is selected from O, S, N (Rz) or C (RxRy); The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl; Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings; The Rd1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2.

6. The carbazole-containing compound according to claim 1, characterized in that, The Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, or any of the groups listed below: The t is independently selected from CH, or one, two or three ts in each group are selected from N, and the rest are selected from CH. When t is bonded to other groups, the t is selected from C atoms. The Rz is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd1 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings; The Rx and Ry are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 10 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

7. The carbazole-containing compound according to claim 1, characterized in that, The L1, L2, and L3 are independently selected from any one of the following groups or combinations thereof: The u is independently selected from CH or N, and when u is bonded to other groups, the u is selected from C atoms; The T is selected from O, S, N (Rw) or C (RhRi); The Rw is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl; The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rh and Ri are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rh and Ri can be connected to each other to form substituted or unsubstituted rings; The Rm is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.

8. The carbazole-containing compound according to claim 1, characterized in that, The carbazole-containing compound is selected from any one of the following compounds: 。 9. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, characterized in that, The organic functional layer comprises any one or more of the carbazole-containing compounds described in any one of claims 1 to 8.

10. An organic electroluminescent device according to claim 9, wherein the organic functional layer comprises a capping layer located outside either the anode or the cathode, characterized in that, The coating layer comprises any one or more of the carbazole-containing compounds according to any one of claims 1 to 8.

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