Carbazole derivative and organic electroluminescent device thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a carbazole derivative and an organic electroluminescent device thereof. The carbazole derivative provided by the invention has proper HOMO energy level and LUMO energy level, can be well matched with an adjacent organic functional layer, also has proper charge transfer performance, also has good thermal stability and chemical stability and good film-forming property, and can be used as a main body material in a luminescent layer to improve the luminous efficiency of the luminescent layer. And the driving voltage, luminous efficiency, service life and other performances of the device can be improved.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to a carbazole derivative and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have many advantages such as self-illumination, high brightness, high luminous efficiency, wide viewing angle, fast response, low driving voltage, wide range of material selection, and flexibility, which perfectly meet people's needs for high definition, high image quality, and high portability, and have been widely used in the display and lighting fields.

[0003] OLED devices employ a classic "sandwich" structure, consisting of a cathode, an anode, and a multi-layered functional structure sandwiched between the two electrodes: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The light-emitting layer contains both host and guest materials. When a working voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode. These recombine in the light-emitting layer to generate excitons. Under the influence of an electric field, the excitons migrate, transferring energy to the guest material, causing electrons in its molecules to transition from the ground state to an excited state. Subsequently, the electrons return from the unstable excited state to the ground state, releasing energy in the form of light, thus achieving light emission. The host material primarily functions as an energy transport layer.

[0004] To further improve the performance of OLED devices, such as luminous efficiency, color purity, and lifespan, it is necessary to develop host materials that have high energy level matching with guest materials and adjacent organic functional layers, appropriate charge transport performance, and excellent stability. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides a carbazole derivative having the structure shown in formula (IA) or (IB):

[0006] Wherein, at least one of A, A', B, B', C, and C' is selected from Formula 1-1, and the remainder are independently selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time u appears, it is selected from N or CR, either the same or different. u The R mentioned uEach time it appears, it is selected, either identically or differently, from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, one of Formulas 1-1, or two adjacent R groups. u They can be connected to form a ring; Each time v appears, it is selected from N or CR, either the same or different. v The R mentioned v Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. v They can be connected to form a ring; The L1 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring. The L2 and L3 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The Cy is selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0007] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains the carbazole derivative described in the present invention.

[0008] Beneficial effects: The carbazole derivative provided by this invention has appropriate HOMO and LUMO energy levels, which can be well matched with adjacent organic functional layers. It also has appropriate charge transport performance, good thermal and chemical stability, and good film-forming properties. As the main material in the light-emitting layer, it can improve the driving voltage, luminous efficiency and lifespan of the device. Detailed Implementation

[0009] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. 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.

[0010] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and comprises atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0011] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0012] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0013] In this invention, "silyl group" refers to a -SiH3 group, and "substituted or unsubstituted silyl group" means that one or more H atoms on the silyl group are substituted or unsubstituted. The "substituted or unsubstituted silyl group" can be formed from -Si(R... k )3 indicates that each R kThe groups are selected, either identically or differently, from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The groups are selected, either identically or differently, from the following: hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, and substituted or unsubstituted C6-C60 aryl groups. 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 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following: hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted 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, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinoline. Preferably, the substituted silane alkyl group specifically includes, but is not limited to, trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, vinyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, phenyldimethylsilane alkyl, diphenylpyridylsilane alkyl, phenyldipyridylsilane alkyl, tripyridylsilane alkyl, etc. The aforementioned substituted silane alkyl group is preferably trimethylsilane alkyl, triethylsilane alkyl, triisopropylsilane alkyl, tri-tert-butylsilane alkyl, tert-butyldimethylsilane alkyl, isopropyldimethylsilane alkyl, triphenylsilane alkyl, diphenylmethylsilane alkyl, or phenyldimethylsilane alkyl.

[0014] The alkyl group described in this invention refers to a hydrocarbon group formed 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, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0015] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0016] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The cycloalkenyl groups described above are preferably cyclopentenyl or cyclohexenyl.

[0017] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0018] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. 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, 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, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0019] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, imidazole, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiophene, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, or pyridyl.

[0020] The monovalent group formed by the fusion of an aromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkane, cycloene, cycloyne) fused with an aromatic ring. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. It may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto. The aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms. It may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of aliphatic and aromatic rings may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, and naphthocyclohexyl.

[0021] In this invention, the term "arylene" refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that the arylene is a divalent group.

[0022] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0023] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0024] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0025] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, or C3-C12 cycloalkanes. The alkyl group includes C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, substituted or unsubstituted silyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, cyclopentane, methyl-substituted cyclopropane, cyclopropane, cyclobutane, methyl-substituted cyclobutane, cyclopentane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclobutane, cyclopropane, cyclobutane, cyclopentane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclopropane, cyclobutane, cycloprop ... Cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene The following groups are used: yl, deuterated triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, benzofuranyl, benzothiophene, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzoxazolyl, benzothiazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the substituents may be identical or different from each other, and adjacent substituents may be linked to form a ring.

[0026] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any optional position on the ring.

[0027] Any one of the points. For example, Can represent , , . Can represent , , ; Can represent , , , , , , , , , And so on.

[0028] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , . Can represent or And so on.

[0029] The linked ring structures described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic rings) refer to groups connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples: .

[0030] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0031] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0032] The statement that a certain layer is located "above" another layer or electrode in this invention can be interpreted as being directly above another layer or electrode, or it can be that other layer structures exist in between.

[0033] The term "a certain layer" in this invention, which is "between" two layers, two electrodes, or one layer and an electrode, can be interpreted as the only layer structure between the two, or as having one or more layer structures between them.

[0034] This invention provides a carbazole derivative having the structure shown in formula (IA) or (IB):

[0035] Wherein, at least one of A, A', B, B', C, and C' is selected from Formula 1-1, and the remainder are independently selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time u appears, it is selected from N or CR, either the same or different. u The R mentioned u Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, one of Formulas 1-1, or two adjacent R groups. u They can be connected to form a ring; Each time v appears, it is selected from N or CR, either the same or different. v The R mentioned vEach time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. v They can be connected to form a ring; The L1 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring. The L2 and L3 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The Cy is selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0036] Preferably, the substituents in "substituted or unsubstituted" are independently selected from deuterium atom; fluorine atom; cyano group; methyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; ethyl group; n-propyl group; isopropyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; n-butyl group; sec-butyl group; isobutyl group; tert-butyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; and groups substituted or unsubstituted by one or more of deuterium atom, methyl group, ethyl group, isopropyl group, and tert-butyl group. The following groups, substituted or unsubstituted, are included: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; groups substituted or unsubstituted by one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane; phenyl. Naphthyl, anthracene, phenanthrene, phenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl; methyl, ethyl, n-propyl, isopropyl, n-butyl One or more of the following substituents, tert-butyl, phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl, anthraceneyl, phenanthrene, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and 9,9-dimethylfluorenyl, may be substituted or unsubstituted silyl groups, wherein when there are multiple substituents, the multiple substituents may be the same or different.

[0037] Preferably, one of A, A', B, B', C, C' (A, A', B, B', C or C'), two (A and A', A and B, A and B', A and C, A and C', B and B', B and C, B and C', C and C'), or three (A, A' and B, A, A' and C, A, A' and C', A, B and C, A, B and C', A, B' and C', A, B' and C', A, C and C', B, B' and C', B, B' and C', B, B' and C', B, B' and C', B' and C', B' and C', B' and C', B' and C', B' and C') or more are selected from Formula 1-1.

[0038] More preferably, in formula IA, A is selected from formula 1-1, or B is selected from formula 1-1, or C is selected from formula 1-1, or A and A' are selected from formula 1-1, or A and C are selected from formula 1-1. In formula IB, A is selected from formula 1-1, or B is selected from formula 1-1, or C is selected from formula 1-1, or A and A' are selected from formula 1-1.

[0039] Preferably, among the multiple u in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0040] Preferably, of the multiple v in each six-membered ring, at most three, at most two, or at most one is selected from N.

[0041] Preferably, the R u R v Each time it appears, the same or different elements are selected from hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; Fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl The following are substituted or unsubstituted phenyl groups: silyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraceneyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. The following groups are: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, or one of the following, or two adjacent R groups. u Can be linked together to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, carbazole ring, benzofuran ring, benzothiophene ring, or two adjacent Rs v Those that can be linked together to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, carbazole ring, benzofuran ring, benzothiophene ring.

[0042] Preferably, at least one of A, A', B, B', C, and C' is selected from Formula 1-1, and the remainder are independently selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantane, substituted or unsubstituted norbornene, substituted or unsubstituted silyl, and one of the following groups:

[0043] The a mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, either the same or different. The R mentioned 11Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 12 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group; X1 is selected from O, S, and CR. 13 R 14 or NR 15 The R mentioned 13 R 14 R 15 The R is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring. 13 R 14 They can be connected to form a ring; The X2 is selected from O, S or NR. 16 The R mentioned 16 It is selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0044] Preferably, the Cy is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantane, substituted or unsubstituted norbornene, and one of the following groups:

[0045] The a mentioned 11 b 11 c 11 d 11 e 11 f 11 g 11 h 11 i 11 j 11 R 11 R 12 X1 and X2 are as described in this invention.

[0046] Preferably, the R 11Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom Fungi, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The phenyl group is substituted with one or more of the following: trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiaphene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0047] Preferably, the R 12 Each time it appears, it is selected from the following groups, either identically or differently: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl group; triphenylsilyl group; dimethylphenylsilyl group; methyl diphenylsilyl group; methyl group; deuterated methyl group; trifluoromethyl group; ethyl group; n-propyl group; isopropyl group; deuterated isopropyl group; n-butyl group; isobutyl group; sec-butyl group; tert-butyl group; deuterated tert-butyl group; cyclopropane group; cyclobutane group; cyclopentane group; cyclohexane group; cycloheptane group; adamantane group; norbornene group.

[0048] Preferably, the R 13 R 14 R 15Independently selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterium Phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthracene One or more of the following groups, substituted or unsubstituted: phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl, biphenyl, naphthyl Anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, and benzocycloheptane are all mentioned above, and R is mentioned above. 13 R 14 They can be connected to form a ring.

[0049] Preferably, the R 16Each time it appears, it is selected from the following groups, either identically or differently: methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyldiphenylsilyl Alkyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted benzene One or more of the following groups, substituted or unsubstituted: phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, phenyl One of the following: phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0050] Preferably, L1 is selected from one of the following groups:

[0051] Preferably, L2 and L3 are independently selected from one of the single-bonded groups, as shown below:

[0052] Wherein, the a 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

[0053] Preferably, the R 101Each time it appears, the same or different elements are selected from hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornyl; deuterium atom Fungi, fluorine atom, cyano, trimethylsilyl, triphenylsilyl, dimethylphenylsilyl, methyl diphenylsilyl, methyl, deuterated phenyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl The phenyl group is substituted with one or more of the following: trimethylsilyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthraquinyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiaphene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane. Or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0054] Preferably, the R 102 Each time it appears, the same or different elements are selected from one of the following: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano group; trimethylsilyl; triphenylsilyl; dimethylphenylsilyl; methyl diphenylsilyl; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornenealkyl.

[0055] Preferably, the carbazole derivative is selected from one of the following compounds: .

[0056] The carbazole derivative shown in formula (IA) of this invention can be prepared by either synthetic route one or synthetic route two: Synthesis Route 1:

[0057] Synthesis Route 2:

[0058] The carbazole derivatives shown in this invention formula (IB) can be prepared by synthetic route three or synthetic route four: Synthesis Route 3:

[0059] Synthesis Route 4:

[0060] Wherein, A, A', B, B', C, C', u, v, L1, and L2 are as described in this invention; each time P1, P2, and P3 appear, they are selected from fluorine, chlorine, bromine, or iodine atoms, either the same or different; each time Q appears, it is selected from B(OH)2 or... .

[0061] In either synthetic route one or synthetic route three, compound (Y1) and compound (Y2) undergo a CN coupling reaction to obtain intermediate (M). Intermediate (M) then undergoes a CN coupling reaction or a CC coupling reaction with compound (Y3) or compound (Y5) to obtain the target compound (IA) or (IB).

[0062] In synthetic route two or four, compound (Y1) and compound (Y2) undergo a CN coupling reaction to obtain intermediate (M). Intermediate (M) undergoes borosilicate or borate reaction to obtain intermediate (N). Intermediate (N) then undergoes a CC coupling reaction with compound (Y4) or (Y6) to obtain target compound (IA) or (IB).

[0063] The above synthetic route employs reaction types commonly used in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation method utilizes readily available raw materials, has a simple process, and yields excellent results. This invention can also employ other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0064] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer contains the carbazole derivative described in the present invention.

[0065] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the light-emitting layer contains the carbazole derivative described in this invention.

[0066] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material contains the carbazole derivative described in this invention.

[0067] Preferably, the light-emitting layer comprises a first host material, a second host material, and a guest material, wherein the first host material contains the carbazole derivative described in this invention.

[0068] Preferably, the light-emitting layer further includes a sensitizer.

[0069] Preferably, the organic electroluminescent device further includes a capping layer located on the side of the cathode away from the anode.

[0070] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Alternatively, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer.

[0071] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4''-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1~HT-18, compounds p-1~p-5, but not limited to these.

[0072] .

[0073] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a value of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0074] The light-emitting auxiliary layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1 [-Biphenyl]-4-amine, compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0075] The luminescent layer of this invention comprises a guest material and a host material, and a dual-host material formed by two host materials can be used. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, aromatic amine compounds, etc. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole-yl)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 9,10-bis(2-naphthyl)anthracene (ADN), etc., and carbazole derivatives of this invention, but are not limited thereto. Preferably, the host material is selected from the carbazole derivatives of this invention. The guest material includes, but is not limited to, aromatic amine derivatives, boron compounds, metal complexes, etc. Specific examples may include, but are not limited to, tri(2-phenylpyridine)iridium (Ir(ppy)3), di(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tri(1-phenyl-isoquinoline)iridium (Ir(piq)3), and 2,5,8,11-tetratert-butylperylene (TBPe).

[0076] The sensitizer described in this invention refers to a material that enables the luminescent material in the light-emitting layer to fully utilize electroexcitons, thereby improving the performance of OLED devices. In organic electroluminescent devices, the sensitizer may perform functions such as exciton trapping, exciton conversion, and exciton transfer. The sensitizers are mainly classified into phosphorescent sensitizers, TADF sensitizers, and excitocomplex sensitizers. Examples of phosphorescent sensitizers include iridium complexes and platinum complexes. TADF sensitizers primarily utilize TADF materials, and excitocomplex sensitizers consist of donor and acceptor materials.

[0077] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0078] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0079] The electron transport layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can utilize high-electron-transporting materials such as aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, and polymers. Examples of electron transport materials for the electron transport layer include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), and 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited to these.

[0080] The hole blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The hole blocking material used in the hole blocking layer requires a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the hole blocking material must be lower than that of the host material of the emissive layer to effectively block holes. Further, the electron mobility of the hole blocking layer material used is 10... -6 cm 2A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq, but these are not limited to these.

[0081] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0082] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0083] The capping layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, and compounds CP-1 to CP-5, but are not limited thereto.

[0084]

[0085] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0086] The thickness of each of the aforementioned organic layers is typically between 1 nanometer and 100 micrometers, preferably between 5 nanometers and 1000 nanometers, and more preferably between 5 nanometers and 200 nanometers. The thickness of the anode and cathode is adjusted according to the required transparency.

[0087] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0088] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0089] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, 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.

[0090] [Synthetic Example 1] Synthesis of intermediate GG

[0091] Under nitrogen protection, FF-11 (16.72 g, 100 mmol), bb-152 (19.55 g, 100 mmol), and sodium tert-butoxide (14.42 g, 150 mmol) dissolved in 600 mL toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.92 g, 1.00 mmol) and X-Phos (1.43 g, 3.00 mmol) were then added. The mixture of the above reactants was heated under reflux for 5.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded intermediate GG-152 (21.41 g, 76% yield). HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 281.0918 (theoretical value: 281.0909).

[0092] Following the preparation method of intermediate GG-152, the following intermediates were synthesized by equimolar substitution of the raw materials:

[0093] [Synthetic Example 2] Preparation of Compound 11:

[0094] Under nitrogen protection, AA-11 (40.71 g, 100 mmol), BB-11 (28.29 g, 100 mmol), Pd(OAc)2 (0.45 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.74 g, 6 mmol), sodium tert-butoxide (28.83 g, 300 mmol), and 500 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to give intermediate CC-11 (42.19 g, 75%). HPLC purity ≥99.81%. Mass spectrometry: 561.1079 (theoretical value: 561.1092).

[0095] Under nitrogen protection, CC-11 (6.82 g, 50 mmol), DD-11 (1.67 g, 50.00 mmol), Pd2(dba)3 (0.55 g, 0.60 mmol), X-Phos (0.87 g, 3.00 mmol), sodium tert-butoxide (14.42 g, 150.00 mmol), and 270 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to give intermediate EE-11 (24.25 g, 71%). HPLC purity ≥99.85%. Mass spectrometry: 682.2188 (theoretical value: 682.2176).

[0096] Under nitrogen protection, EE-11 (6.82 g, 10 mmol), FF-11 (1.67 g, 10.00 mmol), Pd(OAc)2 (0.04 g, 0.2 mmol), PCy3 (0.17 g, 0.6 mmol), sodium tert-butoxide (2.88 g, 30 mmol), and 200 mL of toluene were added to a reaction flask. The system was heated under reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to give compound 11 (5.94 g, 73%). HPLC purity ≥99.93%. Mass spectrometry: 813.3158 (theoretical value: 813.3144). Theoretical elemental content (%) C 61 H 39N3: C, 90.01; H, 4.83; N, 5.16. Actual element content (%): C, 90.06; H, 4.81; N, 5.14.

[0097] [Synthetic Example 3] Preparation of Compound 43:

[0098] Following the preparation method of Example 2, BB-11 was replaced with an equimolar amount of BB-43, with other steps remaining unchanged, to obtain compound 43 (6.68 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 904.0870 (theoretical value: 904.0850). Theoretical elemental content (%) C 67 H 41 N3O: C, 89.01; H, 4.57; N, 4.65. Actual element content (%): C, 89.06; H, 4.55; N, 4.62.

[0099] [Synthetic Example 4] Preparation of Compound 116:

[0100] According to the preparation method in Synthesis Example 2, BB-11 was replaced with an equimolar amount of BB-116, and FF-11 was replaced with an equimolar amount of FF-116, with other steps remaining unchanged, to obtain compound 116 (7.55 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 1077.5037 (theoretical value: 1077.5022). Theoretical elemental content (%) C 81 H 63 N3: C, 90.21; H, 5.89; N, 3.90. Actual element content (%): C, 90.23; H, 5.86; N, 3.92.

[0101] [Synthetic Example 5] Preparation of Compound 119:

[0102] Following the preparation method of Example 2, FF-11 was replaced with an equimolar amount of FF-119, with other steps remaining unchanged, to obtain compound 119 (7.66 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1109.4580 (theoretical value: 1109.4561). Theoretical elemental content (%) C 79 H 63 N3Si2: C, 85.44; H, 5.72; N, 3.78. Actual elemental content (%): C, 85.46; H, 5.73; N, 3.75.

[0103] [Synthetic Example 6] Preparation of Compound 131:

[0104] Following the preparation method in Example 2, BB-11 was replaced with an equimolar amount of BB-131, and FF-11 was replaced with an equimolar amount of FF-131, with other steps remaining unchanged, to obtain compound 131 (8.82 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1129.4383 (theoretical value: 1129.4396). Theoretical elemental content (%) C 86 H 55 N3: C, 91.38; H, 4.90; N, 3.72. Actual element content (%): C, 91.39; H, 4.92; N, 3.70.

[0105] [Synthetic Example 7] Preparation of Compound 136:

[0106] Following the preparation method of Synthesis Example 2, BB-11 was replaced with an equimolar amount of BB-116, and FF-11 was replaced with an equimolar amount of FF-136, with other steps remaining unchanged, to obtain compound 136 (6.78 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 940.3579 (theoretical value: 940.3566). Theoretical elemental content (%) C 70 H 44 N4: C, 89.33; H, 4.71; N, 5.95. Actual element content (%): C, 89.37; H, 4.74; N, 5.92.

[0107] [Synthetic Example 8] Preparation of Compound 142:

[0108] Following the preparation method of Synthesis Example 2, FF-11 was replaced with an equimolar amount of FF-142, with other steps remaining unchanged, to obtain compound 142 (7.90 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1143.4323 (theoretical value: 1143.4301). Theoretical elemental content (%) C 85 H 53 N5: C, 89.21; H, 4.67; N, 6.12. Actual element content (%): C, 89.24; H, 4.63; N, 6.15.

[0109] [Synthetic Example 9] Preparation of Compound 152:

[0110] Under nitrogen protection, AA-11 (40.71 g, 100 mmol), BB-152 (35.90 g, 100 mmol), Pd(OAc)2 (0.45 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.74 g, 6 mmol), sodium tert-butoxide (28.83 g, 300 mmol), and 800 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to obtain intermediate CC-152 (49.81 g, 78%). HPLC purity ≥99.78%. Mass spectrometry: 637.1425 (theoretical value: 637.1405).

[0111] Under nitrogen protection, CC-152 (44.70 g, 70 mmol), DD-11 (14.11 g, 70 mmol), Pd2(dba)3 (0.73 g, 0.8 mmol), X-Phos (2.00 g, 4.2 mmol), sodium tert-butoxide (20.18 g, 210 mmol), and 600 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to obtain intermediate EE-152 (39.87 g, 75%). HPLC purity ≥99.83%. Mass spectrometry: 758.2479 (theoretical value: 758.2489).

[0112] Under nitrogen protection, EE-152 (30.37 g, 40.00 mmol), pinacol diborate (10.16 g, 40.00 mmol), and K₂CO₃ (8.29 g, 60.00 mmol) were dissolved in 150 mL of toluene / ethanol / water (3:1:1). Pd(dppf)Cl₂ (0.29 g, 0.40 mmol) was added with stirring, and the mixture was heated to reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol (6:2) to give intermediate FF-152 (28.23 g, 83% yield); HPLC purity ≥ 99.72%. Mass spectrometry m / z: 626.2431 (theoretical value: 626.2449).

[0113] Under nitrogen protection, FF-152 (8.50 g, 10.00 mmol), GG-152 (2.82 g, 10.00 mmol), K2CO3 (2.07 g, 15.00 mmol), Pd(PPh3)4 (0.12 g, 0.10 mmol), and 100 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give compound 152 (7.57 g, yield 78%). HPLC analysis showed that the purity of the solid was ≥99.94%. Mass spectrometry m / z: 969.4036 (theoretical value: 969.4021).

[0114] [Synthetic Example 10] Preparation of Compound 166:

[0115] Following the preparation method of Synthesis Example 9, BB-152 was replaced with an equimolar amount of BB-11, and GG-152 was replaced with an equimolar amount of GG-166, with other steps remaining unchanged, to obtain compound 166 (6.32 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 929.3427 (theoretical value: 929.3406). Theoretical elemental content (%) C 69 H 43 N3O: C, 89.10; H, 4.66; N, 4.52. Actual element content (%): C, 89.13; H, 4.62; N, 4.54.

[0116] [Synthetic Example 11] Preparation of Compound 167:

[0117] Following the preparation method of Synthesis Example 9, BB-152 was replaced with an equimolar amount of BB-131, and GG-152 was replaced with an equimolar amount of GG-167, with other steps remaining unchanged, to obtain compound 167 (6.86 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 890.3432 (theoretical value: 890.3409). Theoretical elemental content (%) C 66 H 42 N4: C, 88.96; H, 4.75; N, 6.29. Actual element content (%): C, 88.94; H, 4.76; N, 6.27.

[0118] [Synthetic Example 12] Preparation of Compound 175:

[0119] Under nitrogen protection, AA-175 (18.99 g, 50 mmol), BB-175 (16.11 g, 50.00 mmol), Pd(OAc)₂ (0.22 g, 1.00 mmol), tri-tert-butylphosphine tetrafluoroborate (0.87 g, 3.00 mmol), sodium tert-butoxide (14.42 g, 150.00 mmol), and 270 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to give intermediate EE-175 (22.01 g, 71%). HPLC purity ≥99.83%. Mass spectrometry: 620.2038 (theoretical value: 620.2019).

[0120] Under nitrogen protection, EE-175 (6.20 g, 10 mmol), FF-11 (1.67 g, 10.00 mmol), Pd2(dba)3 (0.37 g, 0.4 mmol), X-Phos (0.29 g, 0.6 mmol), sodium tert-butoxide (2.88 g, 30 mmol), and 200 mL of toluene were added to a reaction flask. The system was heated under reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to give compound 175 (5.94 g, 73%). HPLC purity ≥99.90%. Mass spectrometry: 751.2966 (theoretical value: 751.2987).

[0121] [Synthetic Example 13] Preparation of Compound 182:

[0122] Following the preparation method of Synthesis Example 12, AA-175 was replaced with an equimolar amount of AA-182, with other steps remaining unchanged, to obtain compound 182 (6.43 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 813.3157 (theoretical value: 813.3144). Theoretical elemental content (%) C 61 H 39 N3: C, 90.01; H, 4.83; N, 5.16. Actual element content (%): C, 90.03; H, 4.84; N, 5.15.

[0123] [Synthetic Example 14] Preparation of Compound 188:

[0124] Following the preparation method of Synthesis Example 12, AA-175 was replaced with an equimolar amount of AA-182, with other steps remaining unchanged, to obtain compound 188 (6.32 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 889.3469 (theoretical value: 889.3457). Theoretical elemental content (%) C 67 H 43 N3: C, 90.41; H, 4.87; N, 4.72. Actual element content (%): C, 90.45; H, 4.86; N, 4.74.

[0125] [Synthetic Example 15] Preparation of Compound 279:

[0126] Following the preparation method of Example 2, FF-11 was replaced with an equimolar amount of GG-279, with other steps remaining unchanged, to obtain compound 279 (7.44 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1047.3583 (theoretical value: 1047.3573). Theoretical elemental content (%) C 75 H 45 N5O2: C, 85.94; H, 4.33; N, 6.68. Actual element content (%): C, 85.93; H, 4.34; N, 6.66.

[0127] [Synthetic Example 16] Preparation of Compound 281:

[0128] Following the preparation method of Synthesis Example 12, AA-175 was replaced with an equimolar amount of AA-182, and FF-11 was replaced with an equimolar amount of FF-281, with other steps remaining unchanged, to obtain compound 281 (6.76 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 979.3578 (theoretical value: 979.3563). Theoretical elemental content (%) C 73 H 45 N3O: C, 89.45; H, 4.63; N, 4.29. Actual element content (%): C, 89.47; H, 4.65; N, 4.28.

[0129] [Synthetic Example 17] Preparation of Compound 287:

[0130] Under nitrogen protection, AA-182 (44.20 g, 100 mmol), BB-287 (32.22 g, 100 mmol), Pd(OAc)2 (0.45 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.74 g, 6 mmol), sodium tert-butoxide (28.83 g, 300 mmol), and 800 mL of toluene were added to a reaction flask. The system was heated under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The solvent was then removed under vacuum, and the mixture was recrystallized from dichloromethane / hexane to obtain intermediate EE-287 (53.29 g, 78%). HPLC purity ≥99.80%. Mass spectrometry: 682.2197 (theoretical value: 682.2176).

[0131] Under nitrogen protection, EE-287 (27.33 g, 40.00 mmol), pinacol diborate (10.16 g, 40.00 mmol), and K₂CO₃ (8.29 g, 60.00 mmol) were dissolved in 150 mL of toluene / ethanol / water (3:1:1). Pd(dppf)Cl₂ (0.29 g, 0.40 mmol) was added with stirring, and the mixture was heated to reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol (6:2) to give intermediate FF-287 (25.40 g, 82% yield); HPLC purity ≥ 99.72%. Mass spectrometry m / z: 774.7722 (theoretical value: 774.7710).

[0132] Under nitrogen protection, FF-287 (7.75 g, 10.00 mmol), GG-287 (3.90 g, 10.00 mmol), K2CO3 (2.07 g, 15.00 mmol), Pd(PPh3)4 (0.12 g, 0.10 mmol), and 100 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give compound 287 (7.51 g, yield 75%). HPLC analysis showed that the purity of the solid was ≥99.94%. Mass spectrometry m / z: 1001.4723 (theoretical value: 1001.4709). Theoretical elemental content (%) C 75 H 59 N3: C, 89.87; H, 5.93; N, 4.19, Actual element content (%): C, 89.84; H, 5.96; N, 4.17.

[0133] [Synthetic Example 18] Preparation of Compound 309:

[0134] According to the preparation method in Synthesis Example 2, AA-11 was replaced with an equimolar amount of FF-309, BB-11 was replaced with an equimolar amount of BB-309, and FF-11 was replaced with an equimolar amount of AA-11, while other steps remained unchanged, to obtain compound 309 (7.32 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 975.4570 (theoretical value: 975.4552). Theoretical elemental content (%) C 73 H 57 N3: C, 89.81; H, 5.89; N, 4.30. Actual element content (%): C, 89.83; H, 5.84; N, 4.34.

[0135] [Synthetic Example 19] Preparation of Compound 313:

[0136] Following the preparation method in Example 2, AA-11 was replaced with an equimolar amount of FF-11, and FF-11 was replaced with an equimolar amount of GG-313, with other steps remaining unchanged, to obtain compound 313 (6.27 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 813.3156 (theoretical value: 813.3144). Theoretical elemental content (%) C 61 H 39 N3: C, 90.01; H, 4.83; N, 5.16. Actual element content (%): C, 90.02; H, 4.84; N, 5.14.

[0137] [Synthetic Example 20] Preparation of Compound 319:

[0138] Following the preparation method in Example 2, AA-11 was replaced with an equimolar amount of FF-319, and FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 319 (7.31 g). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 913.3469 (theoretical value: 913.3457). Theoretical elemental content (%) C 69 H 43 N3: C, 90.66; H, 4.74; N, 4.60. Actual element content (%): C, 90.64; H, 4.73; N, 4.63.

[0139] [Synthetic Example 21] Preparation of Compound 326:

[0140] Following the preparation method of Synthesis Example 2, AA-11 was replaced with an equimolar amount of FF-309, and FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 326 (6.95 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 925.4378 (theoretical value: 925.4396). Theoretical elemental content (%) C 69 H 55 N3: C, 89.48; H, 5.99; N, 4.54. Actual element content (%): C, 89.46; H, 5.97; N, 4.55.

[0141] [Synthetic Example 22] Preparation of Compound 341:

[0142] According to the preparation method in Synthesis Example 2, AA-11 was replaced with an equimolar amount of FF-309, BB-11 was replaced with an equimolar amount of BB-341, and FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 341 (7.25 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 965.4721 (theoretical value: 965.4709). Theoretical elemental content (%) C 72 H 59 N3: C, 89.50; H, 6.15; N, 4.35. Actual element content (%): C, 89.51; H, 6.16; N, 4.37.

[0143] [Synthetic Example 23] Preparation of Compound 378:

[0144] Following the preparation method in Example 2, AA-11 was replaced with an equimolar amount of AA-378, and FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 378 (7.46 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1065.4071 (theoretical value: 1065.4083). Theoretical elemental content (%) C 81 H 51 N3: C, 91.24; H, 4.82; N, 3.94. Actual element content (%): C, 91.27; H, 4.85; N, 3.95.

[0145] [Synthetic Example 24] Preparation of Compound 383:

[0146] According to the preparation method in Example 2, AA-11 was replaced with an equimolar amount of AA-383, BB-11 was replaced with an equimolar amount of BB-131, and FF-11 was replaced with an equimolar amount of AA-11, while other steps remained unchanged, to obtain compound 383 (7.25 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1005.4063 (theoretical value: 1005.4083). Theoretical elemental content (%) C 76 H 51 N3: C, 90.72; H, 5.11; N, 4.18. Actual element content (%): C, 90.74; H, 5.13; N, 4.15.

[0147] [Synthetic Example 25] Preparation of Compound 384:

[0148] Following the preparation method in Example 2, AA-11 was replaced with an equimolar amount of AA-384, and FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 384 (7.16 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 967.3690 (theoretical value: 967.3675). Theoretical elemental content (%) C 71 H 45 N5: C, 88.08; H, 4.69; N, 7.23. Actual element content (%): C, 88.04; H, 4.65; N, 7.22.

[0149] [Synthetic Example 26] Preparation of Compound 385:

[0150] According to the preparation method in Synthesis Example 2, AA-11 was replaced with an equimolar amount of AA-385, BB-11 was replaced with an equimolar amount of BB-116, and FF-11 was replaced with an equimolar amount of AA-11, while other steps remained unchanged, to obtain compound 385 (7.22 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1045.3678 (theoretical value: 1045.3668). Theoretical elemental content (%) C 77 H 47 N3O2: C, 88.40; H, 4.53; N, 4.02. Actual element content (%): C, 88.41; H, 4.52; N, 4.04.

[0151] [Synthetic Example 27] Preparation of Compound 415:

[0152] Following the preparation method in Example 2, AA-11 was replaced with an equimolar amount of AA-415, and BB-11 was replaced with an equimolar amount of BB-116, with other steps remaining unchanged, to obtain compound 415 (6.85 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1053.4076 (theoretical value: 1053.4083). Theoretical elemental content (%) C 80 H 51 N3: C, 91.14; H, 4.88; N, 3.99. Actual element content (%): C, 91.15; H, 4.86; N, 3.98.

[0153] [Synthetic Example 28] Preparation of Compound 419:

[0154] Following the preparation method of Example 2, FF-11 was replaced with an equimolar amount of AA-11, with other steps remaining unchanged, to obtain compound 419 (7.06 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1053.4063 (theoretical value: 1053.4083). Theoretical elemental content (%) C 80 H 51 N3: C, 91.14; H, 4.88; N, 3.99. Actual element content (%): C, 91.16; H, 4.87; N, 3.96.

[0155] [Synthetic Example 29] Preparation of Compound 431:

[0156] Following the preparation method of Synthesis Example 9, BB-152 was replaced with an equimolar amount of BB-11, and GG-152 was replaced with an equimolar amount of GG-431, with other steps remaining unchanged, to obtain compound 431 (5.61 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 889.3437 (theoretical value: 889.3457). Theoretical elemental content (%) C 67 H 43 N3: C, 90.41; H, 4.87; N, 4.72. Actual element content (%): C, 90.43; H, 4.84; N, 4.71.

[0157] [Synthetic Example 30] Preparation of Compound 443:

[0158] According to the preparation method in Synthesis Example 9, BB-152 was replaced with an equimolar amount of BB-131, DD-11 was replaced with an equimolar amount of DD-384, and GG-152 was replaced with an equimolar amount of GG-443, with other steps remaining unchanged, to obtain compound 443 (6.38 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 965.3750 (theoretical value: 965.3770). Theoretical elemental content (%) C 73 H 47 N3: C, 90.75; H, 4.90; N, 4.35. Actual element content (%): C, 90.74; H, 4.92; N, 4.33.

[0159] [Synthetic Example 31] Preparation of Compound 452:

[0160] Following the preparation method of Synthesis Example 9, BB-152 was replaced with an equimolar amount of BB-116, and GG-152 was replaced with an equimolar amount of GG-452, with other steps remaining unchanged, to obtain compound 452 (6.28 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 995.3351 (theoretical value: 995.3334). Theoretical elemental content (%) C 73 H 45 N3S: C, 88.01; H, 4.55; N, 4.22. Actual element content (%): C, 88.03; H, 4.54; N, 4.21.

[0161] [Synthetic Example 32] Preparation of Compound 553:

[0162] Following the preparation method of Synthesis Example 17, BB-287 was replaced with an equimolar amount of BB-175, and GG-287 was replaced with an equimolar amount of GG-553, with other steps remaining unchanged, to obtain compound 553 (5.79 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 890.3429 (theoretical value: 890.3409). Theoretical elemental content (%) C 66 H 42 N4: C, 88.96; H, 4.75; N, 6.29. Actual element content (%): C, 88.94; H, 4.76; N, 6.26.

[0163] [Synthetic Example 33] Preparation of Compound 604:

[0164] Following the preparation method of Synthesis Example 17, BB-287 was replaced with an equimolar amount of BB-604, and GG-287 was replaced with an equimolar amount of GG-431, with other steps remaining unchanged, to obtain compound 604 (7.65 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1141.4378 (theoretical value: 1141.4396). Theoretical elemental content (%) C 87 H 55 N3: C, 91.47; H, 4.85; N, 3.68. Actual element content (%): C, 91.46; H, 4.85; N, 3.63.

[0165] [Synthetic Example 34] Preparation of Compound 625:

[0166] Following the preparation method of Synthesis Example 9, AA-11 was replaced with an equimolar amount of FF-11, BB-152 with an equimolar amount of BB-11, and GG-152 with an equimolar amount of GG-625, while other steps remained unchanged, yielding compound 625 (5.79 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 889.3446 (theoretical value: 889.3457). Theoretical elemental content (%) C 67 H 43 N3: C, 90.41; H, 4.87; N, 4.72. Actual element content (%): C, 90.43; H, 4.84; N, 4.75.

[0167] [Synthetic Example 35] Preparation of Compound 662:

[0168] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of AA-662, BB-152 was replaced with an equimolar amount of BB-11, and GG-152 was replaced with an equimolar amount of GG-625, with other steps remaining unchanged, to obtain compound 662 (6.74 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1051.4721 (theoretical value: 1051.4711). Theoretical elemental content (%) C 79 H 41 D 10 N3: C, 90.17; H, 5.84; N, 3.99. Actual element content (%): C, 90.16; H, 5.88; N, 3.94.

[0169] [Synthetic Example 36] Preparation of Compound 688:

[0170] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of FF-309, BB-152 was replaced with an equimolar amount of BB-688, and GG-152 was replaced with an equimolar amount of GG-688, with other steps remaining unchanged, to obtain compound 688 (6.95 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1051.4844 (theoretical value: 1051.4865). Theoretical elemental content (%) C 79 H 61 N3: C, 90.16; H, 5.84; N, 3.99. Actual element content (%): C, 90.15; H, 5.86; N, 3.94.

[0171] [Synthetic Example 37] Preparation of Compound 713:

[0172] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of FF-11, BB-152 with an equimolar amount of BB-11, DD-11 with an equimolar amount of DD-713, and GG-152 with an equimolar amount of GG-713, while other steps remained unchanged, yielding compound 713 (6.54 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 989.3760 (theoretical value: 989.3770). Theoretical elemental content (%) C 75 H 47 N3: C, 90.97; H, 4.78; N, 4.24. Actual element content (%): C, 90.96; H, 4.77; N, 4.23.

[0173] [Synthetic Example 38] Preparation of Compound 738:

[0174] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of FF-11, BB-152 was replaced with an equimolar amount of BB-116, and GG-152 was replaced with an equimolar amount of GG-738, with other steps remaining unchanged, to obtain compound 738 (6.09 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 965.3759 (theoretical value: 965.3770). Theoretical elemental content (%) C 73 H 47 N3: C, 90.75; H, 4.90; N, 4.35. Actual element content (%): C, 90.77; H, 4.94; N, 4.32.

[0175] [Synthetic Example 39] Preparation of Compound 740:

[0176] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of FF-11, BB-152 was replaced with an equimolar amount of BB-740, and GG-152 was replaced with an equimolar amount of GG-740, with other steps remaining unchanged, to obtain compound 740 (5.90 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 966.3740 (theoretical value: 966.3722). Theoretical elemental content (%) C 72 H 46 N4: C, 89.41; H, 4.79; N, 5.79. Actual element content (%): C, 89.43; H, 4.74; N, 5.76.

[0177] [Synthetic Example 40] Preparation of Compound 766:

[0178] According to the preparation method in Synthesis Example 9, AA-11 was replaced with an equimolar amount of AA-766, BB-152 was replaced with an equimolar amount of BB-766, and GG-152 was replaced with an equimolar amount of GG-766, while other steps remained unchanged, yielding compound 766 (6.01 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 1017.3845 (theoretical value: 1017.3831). Theoretical elemental content (%) C 75 H 47 N 5: C, 88.47; H, 4.65; N, 6.88. Actual element content (%): C, 88.44; H, 4.62; N, 6.87.

[0179] The following are other compounds besides the carbazole derivatives described in this invention used in the device fabrication examples:

[0180] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. The emission spectrum of the device prepared according to this invention was tested at atmospheric pressure and room temperature, as well as at a current density of 10 mA / cm². 2The luminous efficiency was measured. The lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Tables 1 and 2.

[0181] Comparative device fabrication example 1: Comparative device 1

[0182] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0183] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-1 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-1 as hole transport layer with a thickness of 120 nm; c) HT-5 as light-emitting auxiliary layer with a thickness of 30 nm; d) HOST-1, ref-1, and Firpic (mass ratio 48:48:4) as light-emitting layer with a thickness of 30 nm; e) TPBi as hole blocking layer with a thickness of 20 nm; f) TMPyPB and Liq (mass ratio 1:1) as electron transport layer with a thickness of 30 nm; g) LiF as electron injection layer with a thickness of 1 nm; h) Mg and Ag (mass ratio 10:1) as cathode with a thickness of 10 nm; i) CP-1 as capping layer with a thickness of 120 nm.

[0184] Comparative device fabrication examples 2-4: Comparative devices 2-4

[0185] By sequentially replacing ref-1 in the light-emitting layer with ref-2, ref-3, and ref-4, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 4 can be obtained.

[0186] Device fabrication examples 1-39: Light-emitting devices 1-39

[0187] By sequentially replacing ref-1 in the light-emitting layer with compounds 11, 43, 116, 119, 131, 136, 142, 152, 166, 167, 175, 182, 188, 279, 281, 287, 309, 313, 319, 326, 341, 378, 383, 384, 385, 415, 419, 431, 443, 452, 553, 604, 625, 662, 688, 713, 738, 740, and 766 of the present invention, and by following the same steps as in Comparative Device Preparation Example 1, light-emitting devices 1 to 39 can be obtained.

[0188] Table 1

[0189] Comparative device fabrication example 5: Comparative device 5

[0190] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0191] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-14 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-14 as hole transport layer with a thickness of 120 nm; c) HT-8 as light-emitting auxiliary layer with a thickness of 30 nm; d) HOST-2, ref-1, and Ir(ppy)2(m-bppy) (mass ratio 48:48:4) as light-emitting layer with a thickness of 30 nm; e) TPBi as hole blocking layer with a thickness of 20 nm; f) TMPyPB and Liq (mass ratio 1:1) as electron transport layer with a thickness of 30 nm; g) LiF as electron injection layer with a thickness of 1 nm; h) Mg and Ag (mass ratio 10:1) as cathode with a thickness of 10 nm; i) CP-1 as capping layer with a thickness of 120 nm.

[0192] Comparative device fabrication examples 6-8: Comparative devices 6-8

[0193] By sequentially replacing ref-1 in the light-emitting layer with ref-2, ref-3, and ref-4, and following the same steps as in Comparative Device Preparation Example 5, Comparative Devices 6-8 can be obtained.

[0194] Device fabrication examples 40-78: Light-emitting devices 40-78

[0195] The ref-1 in the light-emitting layer is sequentially replaced with compounds 11, 43, 116, 119, 131, 136, 142, 152, 166, 167, 175, 182, 188, 279, 281, 287, 309, 313, 319, 326, 341, 378, 383, 384, 385, 415, 419, 431, 443, 452, 553, 604, 625, 662, 688, 713, 738, 740, and 766 of the present invention. All other steps are the same as those in Comparative Device Preparation Example 1 and Comparative Device Preparation Example 5, and light-emitting devices 40 to 78 can be obtained.

[0196] Table 2

[0197] The device data in Tables 1 and 2 show that the carbazole derivative provided by this invention, when used as the main material of the light-emitting layer in OLED devices, can effectively improve the driving voltage, luminous efficiency, and lifespan of the devices.

[0198] 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 derivative, characterized in that, The carbazole derivatives have the structure shown in formula (IA) or (IB): Wherein, at least one of A, A', B, B', C, and C' is selected from Formula 1-1, and the remainder are independently selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Each time u appears, it is selected from N or CR, either the same or different. u The R mentioned u Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, one of Formulas 1-1, or two adjacent R groups. u They can be connected to form a ring; Each time v appears, it is selected from N or CR, either the same or different. v The R mentioned v Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. v They can be connected to form a ring; The L1 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring. The L2 and L3 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, or a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The Cy is selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

2. The carbazole derivative according to claim 1, characterized in that, One, two, or three of A, A', B, B', C, and C' are selected from Equation 1-1.

3. The carbazole derivative according to claim 1, characterized in that, At least one of A, A', B, B', C, and C' is selected from Formula 1-1, and the remainder are independently selected from one of the following groups: hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted sec-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopropane group, substituted or unsubstituted cyclobutane group, substituted or unsubstituted cyclopentane group, substituted or unsubstituted cyclohexane group, substituted or unsubstituted cycloheptane group, substituted or unsubstituted adamantane group, substituted or unsubstituted norbornyl group, substituted or unsubstituted silyl group, and the following groups: The a mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, either the same or different. The R mentioned 11 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 12 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group; X1 is selected from O, S, and CR. 13 R 14 or NR 15 The R mentioned 13 R 14 R 15 The R is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring. 13 R 14 They can be connected to form a ring; The X2 is selected from O, S or NR. 16 The R mentioned 16 It is selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

4. The carbazole derivative according to claim 1, characterized in that, The Cy is selected from one of the following groups: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantane, substituted or unsubstituted norbornyl. Wherein, the a 11 b 11 c 11 d 11 e 11 f 11 g 11 h 11 i 11 j 11 R 11 R 12 X1 and X2 are all as described in claim 3.

5. The carbazole derivative according to claim 1, characterized in that, The L1 is selected from one of the following groups: The L2 and L3 are independently selected from one of the single-bonded groups shown below: Wherein, the a 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, or substituted or unsubstituted silyl group.

6. The carbazole derivative according to claim 1, characterized in that, The carbazole derivative is selected from one of the following compounds: 。 7. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, characterized in that, The organic layer contains the carbazole derivative as described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The light-emitting layer contains the carbazole derivative as described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, wherein the light-emitting layer comprises a host material and a guest material, characterized in that, The main material contains the carbazole derivative as described in any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 9, wherein the host material comprises a first host material and a second host material, characterized in that, The first host material contains a carbazole derivative as described in any one of claims 1 to 6.

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