A carbazole compound and an organic electroluminescent device thereof

Abstract

This invention provides a carbazole compound and its organic electroluminescent device, relating to the field of organic electroluminescent materials technology. When used as a host material in OLED devices, the carbazole compound of this invention exhibits suitable triplet energy levels, good film-forming properties, and stability, resulting in devices with low driving voltage, good luminous efficiency, and long lifespan. Furthermore, the preparation method of this organic compound is simple, the raw materials are readily available, and it can be widely applied in various fields such as flat panel displays and solid-state lighting, demonstrating good application effects and industrialization prospects.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) possess numerous superior performance characteristics in flat panel displays and solid-state lighting, and hold promise as a replacement for existing liquid crystal displays (LCDs) and fluorescent lighting. Compared to LCDs, OLEDs offer several advantages, including: simpler manufacturing processes, lower cost, lower energy consumption, faster response times, wider viewing angles, self-emissive emission, better adaptability to external environments, and easier fabrication of large-area displays. Furthermore, because the materials required for the light-emitting layer can be vacuum-deposited, the device thickness is small, sometimes only a few millimeters. Moreover, OLEDs can be fabricated not only as rigid displays but also as flexible displays, a feature not found in LCDs. Therefore, OLEDs have broad prospects for development in both academia and industrialization.

[0003] OLED devices resemble a sandwich structure, consisting of electrode material layers and organic functional materials sandwiched between different electrode layers. These various functional materials are stacked together according to their intended use to form the OLED device. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is applied to the positive and negative charges in the organic functional material layers, the positive and negative charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0004] The emitting layer of an OLED device typically consists of a host material and a guest material. The host material acts as an intermediate medium for energy transfer and generally exhibits luminescent inertness. The guest material, acting as a light radiation carrier, is dispersed within the host material to avoid its own concentration quenching effect. To reduce the adverse effects of concentration quenching, the triplet energy levels of the host material should be higher than those of the guest material to prevent energy backflow. The HOMO and LUMO energy levels of the host material should be matched with the HTM and ETM energy levels, respectively, to help reduce the injection barriers for holes and electrons and to capture charge carriers.

[0005] Currently, as OLEDs continue to expand their applications across various fields, their performance, such as luminous efficiency and lifespan, still needs further improvement. Developing host materials with excellent semiconductor properties, suitable triplet energy levels, good film-forming properties, and stability, in order to fabricate higher-performance OLED materials, is a question worthy of our consideration. Summary of the Invention

[0006] To address the aforementioned issues, this invention provides a carbazole compound and its organic electroluminescent device. The organic light-emitting device prepared using this carbazole compound has a lower driving voltage, which can effectively improve the luminous efficiency of the OLED device and extend its lifespan.

[0007] Specifically, the present invention provides a carbazole compound having a structure represented by Formula I:

[0008]

[0009] Group 1:

[0010]

[0011] Wherein, ring A is selected from any one of the substituted or unsubstituted structures in group 1;

[0012] The ring B is selected from chemical formula II, and chemical formula II is fused to ring A in chemical formula I through a * site;

[0013] Each of the V values ​​is independently selected from C(R). t Any one of N;

[0014] The R t It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0015] Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from CH and N.

[0016] Ar1 and Ar2 are each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0017] At least one of Ar1 and Ar2 is selected from any one of chemical formulas III, IV and V;

[0018]

[0019] X1, X2, and X3 are each independently selected from O, S, and C(R). a R b Any one of O, S, and X1, X2, X3, and at least one of O, S, X3 is selected from O, S;

[0020] The R a R b Each and every one is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R a R b The links between them form substituted or unsubstituted rings;

[0021] The R3 is independently selected from any one of hydrogen, cyano, fluorine, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0022] The R4 is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0023] The n3 is selected from integers from 0 to 5; when n3 is greater than 1, two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form substituted or unsubstituted aromatic rings;

[0024] The n4 is selected from integers from 0 to 3; when n4 is greater than 1, two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0025] The Z9, Z 10 Z 11 Z 12 Z 13 Z 14 Z 15 Z 16 Each is independently selected from CH and N, and Z9 and Z 10 Z 11 Z 12 At most one of them is selected from N, Z 13 Z 14 Z 15 Z 16 At most one of them is selected from N;

[0026] L1 and L2 are each independently selected from a single bond or from any of the following structures:

[0027]

[0028] The R6 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocyclic, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0029] The b1 is selected from integers from 0 to 4; the b2 is selected from integers from 0 to 6; the b3 is selected from integers from 0 to 8; the b4 is selected from integers from 0 to 2; the b5 is selected from integers from 0 to 7; the b6 is selected from integers from 0 to 3; when there are two or more R6, the two or more R6 are the same or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring;

[0030] The L o It is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings;

[0031] The R g It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0032] Y4, Y5, and Y6 are each independently selected from O, S, and C(R). h R i ), N(R j Any one of the following;

[0033] The R h R i Each and every one is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R h R i The links between them form substituted or unsubstituted rings;

[0034] The R jIt is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0035] R1 and R2 are each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0036] The n1 is selected from integers from 0 to 4; when n1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0037] The n2 is selected from integers from 0 to 4; when n2 is greater than 1, two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring.

[0038] The present invention also provides an organic electroluminescent device comprising at least one of the carbazole compounds described in the present invention.

[0039] Beneficial effects

[0040] This invention provides a carbazole compound that, when used in the host material of OLED devices, possesses a suitable triplet energy level, which helps reduce the injection barriers for holes and electrons and trap charge carriers, thereby improving the luminous efficiency of the device. Simultaneously, it exhibits good film-forming properties and stability in the material, effectively reducing the driving voltage of organic electroluminescent devices and extending their lifespan.

[0041] In summary, when the compound of the present invention is applied to organic electroluminescent devices, it exhibits good stability and film-forming properties, which can improve the luminous efficiency of the device and extend its service life. Furthermore, the preparation method of the compound is simple, the raw materials are readily available, it can meet the needs of industrialization, and it has good prospects for industrialization. Detailed Implementation

[0042] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0043] In this instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the attached group / fragment.

[0044] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0045] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0046] For example, Can represent Can represent Can represent And so on.

[0047] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0048] The alkyl group referred to in this invention is a general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0049] The silane group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a silane composed of carbon, hydrogen, and silicon atoms. Preferably, it has 3 to 25 carbon atoms, more preferably 3 to 22 carbon atoms, and most preferably 3 to 18 carbon atoms. Specific examples may include trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane, triphenylsilane, etc., but are not limited thereto.

[0050] The cycloalkyl group described in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto.

[0051] The heterocyclic alkyl group described in this invention refers to the general term for groups obtained by replacing one or more carbon atoms in a cycloalkyl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include tetrahydropyrrolyl, piperidinyl, etc., but are not limited thereto.

[0052] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 15 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, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, 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, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0053] 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, or phosphorus atoms, and preferably have 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0054] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.

[0055] The heteroaryl group described in this invention refers to the general term for the group obtained by replacing one or more aromatic carbon atoms in the aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. Specific examples of the monocyclic and fused-ring heteroaryl groups may include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, and dibenzocarbazolyl; specific examples of the polycyclic heteroaryl groups may include, but are not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl.

[0056] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. These groups can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0057] The fused alicyclic and aromatic cyclic groups described in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Specific examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0058] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one hydrogen atom after a heterocyclic alkanes and aromatic rings are fused together. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Specific examples may include benzo[a]hexacyclic butyl, benzo[tetrahydropyrrolyl], benzo[piperidinyl], benzo[a]hexacyclic heptyl, naphtho[tetrahydropyrrolyl], naphtho[piperidinyl], phenanthrene[tetrahydropyrrolyl], phenanthrene[piperidinyl], etc., but are not limited thereto.

[0059] The fused cyclic groups of alicyclic and heteroaromatic rings mentioned in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom after alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Specific examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium benzocycloheptyl, pyrimidinium cyclopropyl, pyrimidinium cyclobutyl, pyrimidinium cyclopentyl, pyrimidinium benzocyclohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazoleocyclopropyl, carbazoleocyclobutyl, carbazoleocyclopentyl, carbazoleocyclohexyl, carbazoleocycloheptyl, etc., but are not limited thereto.

[0060] The fused alicyclic and aromatic cyclic groups described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Specific examples may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0061] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Specific examples may include pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinoxocyclopropyl, pyrimidinoxocyclobutyl, pyrimidinoxocyclopentyl, pyrimidinoxocyclohexyl, pyrimidinoxobenzocycloheptyl, dibenzofuranocyclopropyl, and dibenzofuranocyclopropyl. Furanocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocyclohepyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecyclohepyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocyclohepyl, etc., but not limited to these.

[0062] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, nitro, amino, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred atoms include deuterium, cyano, nitro, amino, halogen atoms, C1-C12 alkyl, C3-C12 silyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, and C1-C12 alkoxy. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, and triphenylene. Perylene, pyrene, fluoranyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, carbazole-indole, pyrrole, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazole, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.

[0063] In this invention, "integers selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, "n1 selected from 0 to 4" means that n1 is selected from 0, 1, 2, 3, or 4. "a1 selected from 0 to 5" means that a1 is selected from 0, 1, 2, 3, 4, or 5. "b2 selected from 0 to 6" means that b2 is selected from 0, 1, 2, 3, 4, 5, or 6. And so on.

[0064] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0065]

[0066] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, pyrimidine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0067] This invention provides a carbazole compound having the structure represented by Formula I:

[0068]

[0069] Group 1:

[0070]

[0071] Wherein, ring A is selected from any one of the substituted or unsubstituted structures in group 1;

[0072] The ring B is selected from chemical formula II, and chemical formula II is fused to ring A in chemical formula I through a * site;

[0073] Each of the V values ​​is independently selected from C(R). t Any one of N;

[0074] The R t It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0075] Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from CH and N.

[0076] Ar1 and Ar2 are each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0077] At least one of Ar1 and Ar2 is selected from any one of chemical formulas III, IV and V;

[0078]

[0079] X1, X2, and X3 are each independently selected from O, S, and C(R). a R b Any one of O, S, and X1, X2, X3, and at least one of O, S, X3 is selected from O, S;

[0080] The R a R b Each and every one is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R a R b The links between them form substituted or unsubstituted rings;

[0081] The R3 is independently selected from any one of hydrogen, cyano, fluorine, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0082] The R4 is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0083] The n3 is selected from integers from 0 to 5; when n3 is greater than 1, two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form substituted or unsubstituted aromatic rings;

[0084] The n4 is selected from integers from 0 to 3; when n4 is greater than 1, two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0085] The Z9, Z 10 Z 11 Z 12 Z 13 Z 14 Z 15 Z 16 Each is independently selected from CH and N, and Z9 and Z 10 Z 11 Z 12 At most one of them is selected from N, Z 13 Z 14 Z 15 Z 16 At most one of them is selected from N;

[0086] L1 and L2 are each independently selected from a single bond or from any of the following structures:

[0087]

[0088]

[0089] The R6 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocyclic, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0090] The b1 is selected from integers from 0 to 4; the b2 is selected from integers from 0 to 6; the b3 is selected from integers from 0 to 8; the b4 is selected from integers from 0 to 2; the b5 is selected from integers from 0 to 7; the b6 is selected from integers from 0 to 3; when there are two or more R6, the two or more R6 are the same or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring;

[0091] The L o It is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings;

[0092] The R g It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0093] Y4, Y5, and Y6 are each independently selected from O, S, and C(R). h R i ), N(R j Any one of the following;

[0094] The R h R iEach and every one is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R h R i The links between them form substituted or unsubstituted rings;

[0095] The R j It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0096] R1 and R2 are each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0097] The n1 is selected from integers from 0 to 4; when n1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0098] The n2 is selected from integers from 0 to 4; when n2 is greater than 1, two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring.

[0099] Preferably, group 1 is:

[0100]

[0101] Where * represents a fusion site.

[0102] Preferably, R1, R2, R4, R6, R a R b 、Rg、R h R i R j R tEach is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted Substituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiroyl Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0103] Preferably, R3 is selected from hydrogen, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzo... Cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted Substituted fluoranthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazoyl Substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.

[0104] Preferably, the carbazole compound is selected from any one of the following structures:

[0105]

[0106] Preferably, Ar1 and Ar2 are each independently selected from any one of the following structures:

[0107]

[0108] The R p R q R r R s Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R p R q The connections between them form substituted or unsubstituted rings, or R r R s They connect to form substituted or unsubstituted rings.

[0109] Preferably, the R p R q R r R sEach is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted Substituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiroyl Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0110] Preferably, Ar1 and Ar2 are each independently selected from any one of the following structures:

[0111]

[0112]

[0113] The n3 is selected from integers from 0 to 5; the n5 is selected from integers from 0 to 7; the n6 is selected from integers from 0 to 8; the n7 is selected from integers from 0 to 1; the n8 is selected from integers from 0 to 2; the n9 is selected from integers from 0 to 9; the n 10 Integers selected from 0 to 4; when there are two or more R3s, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0114] The n4 is selected from integers from 0 to 3; the n 11 Integers selected from 0 to 2; when there are two or more R4s, the two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring.

[0115] Preferably, when Ar1 and Ar2 are not selected from any one of chemical formulas III, IV, and V, they are each independently selected from any one of the following structures:

[0116]

[0117] The R5 is the same or different from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl group;

[0118] a1 is selected from integers from 0 to 5; a2 is selected from integers from 0 to 4; a3 is selected from integers from 0 to 7; a4 is selected from integers from 0 to 9; a5 is selected from integers from 0 to 2; a6 is selected from integers from 0 to 11; a7 is selected from integers from 0 to 3; when there are two or more R5s, the two or more R5s are the same or different from each other, or two adjacent R5s are connected to each other to form a substituted or unsubstituted ring;

[0119] The ring C is selected from substituted or unsubstituted C3 to C10 alicyclic rings;

[0120] Z is selected from either CH or N;

[0121] The R c It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0122] Y1, Y2, and Y3 are each independently selected from O, S, and C(R). d R e ), N(R f Any one of the following;

[0123] The R d R e Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R d R e The links between them form substituted or unsubstituted rings;

[0124] The R fIt is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0125] Preferably, R5, R c R d R e R fEach is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted Substituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiroyl Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0126] Preferably, at most three, two, or one Z in each ring are selected from N.

[0127] Preferably, at most one of Z1, Z2, Z3, and Z4 is selected from N, and at most one of Z5, Z6, Z7, and Z8 is selected from N.

[0128] Preferably, at most one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is selected from N.

[0129] More preferably, when Ar1 and Ar2 are not selected from any one of chemical formulas III, IV, and V, they are each independently selected from any one of the following structures:

[0130]

[0131] The R7 is the same as or different from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl group;

[0132] The c1 is selected from integers from 0 to 5; the c2 is selected from integers from 0 to 4; the c3 is selected from integers from 0 to 7; the c4 is selected from integers from 0 to 9; the c5 is selected from integers from 0 to 2; the c6 is selected from integers from 0 to 11; the c7 is selected from integers from 0 to 3; when there are two or more R7s, the two or more R7s are the same or different from each other, or two adjacent R7s are connected to each other to form a substituted or unsubstituted ring;

[0133] The R k R lIndependently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R k R l The links between them form substituted or unsubstituted rings;

[0134] The R m It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0135] The R n It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0136] Preferably, R7, R k R l R m R nEach is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted Substituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiroyl Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0137] Preferably, at most three, two, or one Z in each ring are selected from N.

[0138] More preferably, when Ar1 and Ar2 are not selected from any one of chemical formulas III, IV, and V, they are each independently selected from any one of the following structures:

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] Preferably, L1 and L2 are each independently selected from a single bond or from any of the following structures:

[0145]

[0146] The R k '、R l 'Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R k '、R l The '' links form substituted or unsubstituted rings;

[0147] The R m 'Selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0148] The R nIt is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0149] Preferably, the R k '、R l '、R m '、R nEach element is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted Substituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted Spirofluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylfuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodiphenylfuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0150] Preferably, L1 and L2 are each independently selected from a single bond or from any of the following structures:

[0151]

[0152]

[0153]

[0154] Most preferably, the carbazole compound is selected from any one of the following structures:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] The above lists some specific structural forms of carbazole compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0173] The present invention also provides an organic electroluminescent device comprising at least one of the carbazole compounds described in the present invention.

[0174] More preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising at least one of the carbazole compounds described in this invention.

[0175] More preferably, the organic layer comprises a light-emitting layer, which comprises at least one of the carbazole compounds described in this invention.

[0176] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the carbazole compounds described in this invention.

[0177] More preferably, the organic electroluminescent device includes an anode, a cathode, an organic layer located between the anode and the cathode, and a capping layer located outside the anode or cathode, the capping layer comprising at least one of the carbazole compounds described in this invention.

[0178] The anode material described in this invention is preferably a material with a high work function. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmission electrode or a reflection electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0179] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0180] The hole transport layer material described in this invention is preferably a material with high hole mobility. The hole transport layer material may include, but is not limited to, biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc.

[0181] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material (also called a matrix material) and a dopant material (also called a guest material). The luminescent layer material can contain multiple host materials and multiple dopant materials. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. In addition to the carbazole compound provided in this invention, it can also contain anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these. The guest material may include, but is not limited to, metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, terbium complexes, europium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc.

[0182] The electron transport layer material described in this invention is preferably a material with high electron mobility. The electron transport layer material may include any one or more of the following structures: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazazole derivatives, azabenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited thereto.

[0183] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0184] The cathode material described in this invention is preferably a material with a low work function, and the cathode can be selected from a transmission electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmission electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0185] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. Substituents can be bonded by methods known in the art, and the type, position, or number of substituents can be changed according to techniques known in the art.

[0186] [Synthesis Route]

[0187] Preparation of compound I:

[0188]

[0189] Xa, Xb, Xc, and Xd are each independently selected from any one of I, Br, and Cl; the limitations of Ar1~Ar2, L1~L2, Z1~Z8, R1~R2, and n1~n2 are the same as those mentioned above.

[0190] Description of raw materials, reagents, and characterization equipment:

[0191] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0192] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0193] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0194] Synthesis Example 1: Synthesis of Compound 2

[0195]

[0196] Synthesis of intermediate A-2:

[0197] Under nitrogen protection, a-2 (36.92 g, 150.00 mmol), b-2 (49.50 g, 150.00 mmol), and sodium tert-butoxide (25.95 g, 270.00 mmol) were dissolved in 600 mL of dehydrated toluene. A toluene solution of palladium acetate (0.34 g, 1.50 mmol) and tri-tert-butylphosphine (1.21 g, 6.00 mmol) was added with stirring, and the mixture was refluxed for 5 hours. After cooling, the mixture was filtered through diatomaceous earth / silica gel. The filtrate was purified by vacuum distillation to remove the organic solvent. The concentrate was recrystallized from toluene, and filtered to obtain intermediate A-2 (55.12 g, 82%). HPLC analysis showed a solid purity ≥99.78%. Mass spectrometry m / z: 447.1018 (theoretical value: 447.1005).

[0198] Synthesis of intermediate B-2:

[0199] Under nitrogen protection, A-2 (53.78 g, 120.00 mmol), b'-2 (29.28 g, 120.00 mmol), potassium carbonate (33.17 g, 240.00 mmol), and Pd(PPh3)4 (1.39 g, 1.20 mmol) were added to a reaction flask, along with 520 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred, and the reaction system was heated under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The resulting solid was recrystallized from toluene to obtain intermediate B-2 (41.55 g, 79%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 437.0404 (theoretical value: 437.0415).

[0200] Synthesis of intermediate C-2:

[0201] Under nitrogen protection, B-2 (30.68 g, 70.00 mmol) was dissolved in THF (300 ml). Then, c-2 (13.39 g, 105.00 mmol), tetrakis(triphenylphosphine)palladium (4.04 g, 3.50 mmol), sodium tert-butoxide (20.20 g, 210.21 mmol), and water (150 ml) were added, and the mixture was stirred under reflux for 7 hours. After the reaction was complete, the mixture was extracted with dichloromethane and water, dried over magnesium sulfate, and the organic layer was concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallization to obtain intermediate C-2 (26.14 g, 77%). HPLC analysis showed a solid purity ≥99.81%. Mass spectrometry m / z: 484.1331 (theoretical value: 484.1342).

[0202] Synthesis of intermediate D-2:

[0203] Under nitrogen protection, C-2 (24.25 g, 50.00 mmol), palladium acetate (0.11 g, 0.50 mmol), cesium carbonate (32.58 g, 100.00 mmol), and tricyclohexylphosphine tetrafluoroborate (0.37 g, 1.00 mmol) were added to 200 mL of dimethylacetamide solution with stirring, and the mixture was refluxed for 7 hours. After complete reaction, the solution was added dropwise to water to precipitate the solid. Recrystallization from a mixed solution of n-hexane and dichloromethane yielded intermediate D-2 (17.04 g, 76%). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 448.1564 (theoretical value: 448.1576).

[0204] Synthesis of compound 2:

[0205] Under nitrogen protection, D-2 (15.70 g, 35.00 mmol), d-2 (6.60 g, 35.00 mmol), copper powder (2.89 g, 45.50 mmol), 18-crown ether-6 (0.93 g, 3.50 mmol), potassium carbonate (5.80 g, 42.00 mmol), and DMF (150 ml) were stirred under reflux for 20 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then purified by silica gel column chromatography (dichloromethane: n-hexane = 1:6) to give compound 2 (14.72 g, 70%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 600.2217 (theoretical value: 600.2202). Theoretical elemental content (%) C 44 H 28 N₂O: C, 87.97; H, 4.70; N, 4.66. Measured elemental content (%): C, 87.92; H, 4.74; N, 4.63.

[0206] Synthesis Example 2: Synthesis of Compound 15

[0207]

[0208] Following the preparation method of Synthesis Example 1, a-2, b'-2, and d-2 were replaced with equimolar amounts of a-15, b'-15, and d-15 to obtain compound 15 (14.63 g, 72%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 580.2529 (theoretical value: 580.2515). Theoretical elemental content (%) C 42 H 32 N₂O: C, 86.87; H, 5.55; N, 4.82. Measured elemental content (%): C, 86.90; H, 5.51; N, 4.87.

[0209] Synthesis Example 3: Synthesis of Compound 28

[0210]

[0211] Following the preparation method of Synthesis Example 1, a-2, b'-2, and d-2 were replaced with equimolar amounts of a-15, b'-28, and d-28 to obtain compound 28 (15.27 g, 75%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 581.2474 (theoretical value: 581.2485). Theoretical elemental content (%) C 42 H 19 D7N2O: C, 86.72; H, 5.72; N, 4.82. Measured elemental content (%): C, 86.76; H, 5.67; N, 4.85.

[0212] Synthesis Example 4: Synthesis of Compound 35

[0213]

[0214] Following the preparation method of Example 1, a-2, b'-2, and d-2 were replaced with equimolar amounts of a-15, b'-35, and d-35 to obtain compound 35 (18.27 g, 67%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 778.2607 (theoretical value: 778.2620). Theoretical elemental content (%) C 57 H 34 N2O2: C, 87.90; H, 4.40; N, 3.60. Measured elemental content (%): C, 87.94; H, 4.36; N, 3.65.

[0215] Synthesis Example 5: Synthesis of Compound 49

[0216]

[0217] Following the preparation method of Synthesis Example 1, a-2, b-2, b'-2, and d-2 were replaced with equimolar amounts of a-15, b-49, b'-49, and d-49 to obtain compound 49 (17.48 g, 66%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 756.2251 (theoretical value: 756.2235). Theoretical elemental content (%) C 54 H 32 N₂OS: C, 85.69; H, 4.26; N, 3.70. Measured elemental content (%): C, 85.74; H, 4.23; N, 3.74.

[0218] Synthesis Example 6: Synthesis of Compound 71

[0219]

[0220] Following the preparation method of Synthesis Example 1, B-2, c-2, and d-2 were replaced with equimolar amounts of B-35, c-71, and d-71 to obtain compound 71 (13.88 g, 66%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 600.2220 (theoretical value: 600.2202). Theoretical elemental content (%) C 44 H 28 N₂O: C, 87.97; H, 4.70; N, 4.66. Measured elemental content (%): C, 87.92; H, 4.74; N, 4.63.

[0221] Synthesis Example 7: Synthesis of Compound 91

[0222]

[0223] Synthesis of intermediate M-91:

[0224] Under nitrogen protection, m-91 (8.10 g, 50.00 mmol), b-91 (14.35 g, 50.00 mmol), K2CO3 (20.73 g, 150.00 mmol), and 500 mL of toluene solvent were added to a reaction flask and stirred. Pd(PPh3)4 (0.58 g, 0.50 mmol) and 85 mL of distilled water were added, the temperature was raised to reflux, and the reaction was stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, the solvent was concentrated by rotary evaporation, and crystals were precipitated by cooling. The solid was filtered, and the obtained solid was recrystallized from toluene to give intermediate M-91 (11.64 g, 84%). HPLC analysis showed the solid purity to be ≥99.89%. Mass spectrometry m / z: 276.0076 (theoretical value: 276.0088).

[0225] Synthesis of compound 91:

[0226] Under nitrogen protection, D-91 (11.63 g, 35.00 mmol), M-91 (9.70 g, 35.00 mmol), copper powder (2.89 g, 45.50 mmol), 18-crown ether-6 (0.93 g, 3.50 mmol), potassium carbonate (5.80 g, 42.00 mmol), and DMF (150 ml) were stirred under reflux for 20 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then purified by silica gel column chromatography (dichloromethane: n-hexane = 1:5) to give compound 91 (14.06 g, 76%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 528.2127 (theoretical value: 528.2140). Theoretical elemental content (%) C 38 H 20 D4N2O: C, 86.34; H, 5.34; N, 5.30. Measured elemental content (%): C, 86.39; H, 5.30; N, 5.34.

[0227] Synthesis Example 8: Synthesis of Compound 101

[0228]

[0229] Synthesis of intermediate B-101:

[0230] Under nitrogen protection, a-2 (29.53 g, 120.00 mmol), b'-101 (29.40 g, 120.00 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) were dissolved in 600 mL of dehydrated toluene. A toluene solution of palladium acetate (0.27 g, 1.20 mmol) and tri-tert-butylphosphine (0.97 g, 4.80 mmol) was added with stirring, and the mixture was refluxed for 5 hours. After cooling, the mixture was filtered through diatomaceous earth / silica gel. The filtrate was purified by vacuum distillation to remove the organic solvent. The concentrate was recrystallized from toluene, and the residue was filtered to obtain intermediate B-101 (36.18 g, 83%). HPLC analysis showed a solid purity ≥99.75%. Mass spectrometry m / z: 362.0069 (theoretical value: 362.0055).

[0231] Synthesis of intermediate E-101:

[0232] Under nitrogen protection, B-101 (32.69 g, 90.00 mmol), pinacol diboronate (24.12 g, 95.00 mmol), and KOAc (17.67 g, 180.00 mmol) were added to 450 mL of 1,4-dioxane. Pd(dppf)Cl2 (0.70 g, 0.95 mmol) was added with stirring, and the mixture was heated under reflux for 6 hours. After the reaction was complete, the reaction solution was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate. The layers were separated by standing, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystals were then precipitated by cooling and filtered again. The resulting solid was recrystallized from toluene to obtain intermediate E-101 (29.54 g, 80%). HPLC analysis showed a solid purity ≥99.79%. Mass spectrometry m / z: 410.1815 (theoretical value: 410.1802).

[0233] Synthesis of intermediate C-101:

[0234] Under nitrogen protection, E-101 (28.72 g, 70.00 mmol), c-101 (14.14 g, 70.00 mmol), potassium carbonate (19.35 g, 140.00 mmol), and Pd(PPh3)4 (0.92 g, 0.80 mmol) were added to a reaction flask, along with 300 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene to obtain intermediate C-101 (21.85 g, 77%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 405.1102 (theoretical value: 405.1113).

[0235] Synthesis of intermediate D-101:

[0236] Under nitrogen protection, C-101 (20.27 g, 50.00 mmol) was dissolved in o-dichlorobenzene (200 ml). Triphenylphosphine (32.79 g, 125.00 mmol) was then added and the mixture was stirred at 200 °C. After the reaction was complete, o-dichlorobenzene was removed by distillation, followed by extraction with dichloromethane and water. The organic layer was dried over magnesium sulfate and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallization to obtain intermediate D-101 (14.00 g, 75%), with a solid purity ≥99.89% as determined by HPLC. Mass spectrometry m / z: 373.1227 (theoretical value: 373.1215).

[0237] Synthesis of compound 101:

[0238] Under nitrogen protection, D-101 (13.07 g, 35.00 mmol), d-101 (11.86 g, 35.00 mmol), copper powder (2.89 g, 45.50 mmol), 18-crown ether-6 (0.93 g, 3.50 mmol), potassium carbonate (5.80 g, 42.00 mmol), and DMF (150 ml) were stirred under reflux for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then purified by silica gel column chromatography (dichloromethane: n-hexane = 1:6) to give compound 101 (16.79 g, 71%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 675.2326 (theoretical value: 675.2311). Theoretical elemental content (%) C 49 H 29 N3O: C, 87.09; H, 4.33; N, 6.22. Measured elemental content (%): C, 87.14; H, 4.30; N, 6.26.

[0239] Synthesis Example 9: Synthesis of Compound 104

[0240]

[0241] Under nitrogen protection, D-104 (9.32 g, 35.00 mmol), d-104 (19.19 g, 70.00 mmol), copper powder (5.72 g, 90.00 mmol), 18-crown ether-6 (1.85 g, 7.00 mmol), potassium carbonate (11.61 g, 84.00 mmol), and DMF (200 ml) were stirred under reflux for 22 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then purified by silica gel column chromatography (dichloromethane: n-hexane = 1:4) to give compound 104 (15.99 g, 70%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 652.2672 (theoretical value: 652.2683). Theoretical elemental content (%) C 44 H 16 D 10 N4O2: C, 80.96; H, 5.56; N, 8.58. Measured elemental content (%): C, 80.91; H, 5.60; N, 8.55.

[0242] Synthesis Example 10: Synthesis of Compound 107

[0243]

[0244] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-107 and b'-35 to obtain compound 107 (14.51 g, 69%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 600.2217 (theoretical value: 600.2202). Theoretical elemental content (%) C 44 H 28 N₂O: C, 87.97; H, 4.70; N, 4.66. Measured elemental content (%): C, 87.92; H, 4.74; N, 4.69.

[0245] Synthesis Example 11: Synthesis of Compound 115

[0246]

[0247] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-115 and d-115 to obtain compound 115 (15.01 g, 74%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 579.2346 (theoretical value: 579.2359). Theoretical elemental content (%) C 42 H 21 D5N2O: C, 87.02; H, 5.39; N, 4.83. Measured elemental content (%): C, 87.07; H, 5.36; N, 4.87.

[0248] Synthesis Example 12: Synthesis of Compound 116

[0249]

[0250] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-116 and b'-35 to obtain compound 116 (14.28 g, 71%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 574.2032 (theoretical value: 574.2045). Theoretical elemental content (%) C 42 H 26 N₂O: C, 87.78; H, 4.56; N, 4.87. Measured elemental content (%): C, 87.73; H, 4.60; N, 4.90.

[0251] Synthesis Example 13: Synthesis of Compound 138

[0252]

[0253] Following the preparation method of Synthesis Example 1, B-2, c-2, and d-2 were replaced with equimolar amounts of B-35, c-138, and d-138 to obtain compound 138 (14.63 g, 68%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 614.2345 (theoretical value: 614.2358). Theoretical elemental content (%) C 45 H 30 N₂O: C, 87.92; H, 4.92; N, 4.56. Measured elemental content (%): C, 87.97; H, 4.89; N, 4.60.

[0254] Synthesis Example 14: Synthesis of Compound 141

[0255]

[0256] Following the preparation method of Synthesis Example 1, D-2 and d-2 were replaced with equimolar amounts of D-138 and d-141 to obtain compound 141 (16.85 g, 65%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 740.2452 (theoretical value: 740.2464). Theoretical elemental content (%) C 54 H 32 N2O2: C, 87.55; H, 4.35; N, 3.78. Measured elemental content (%): C, 87.60; H, 4.32; N, 3.82.

[0257] Synthesis Example 15: Synthesis of Compound 143

[0258]

[0259] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-116 and d-143 to obtain compound 143 (15.39 g, 76%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 578.1980 (theoretical value: 578.1994). Theoretical elemental content (%) C 41 H 26 N2O2: C, 85.10; H, 4.53; N, 4.84. Measured elemental content (%): C, 85.14; H, 4.56; N, 4.81.

[0260] Synthesis Example 16: Synthesis of Compound 145

[0261]

[0262] Following the preparation method of Synthesis Example 7, m-91 and D-91 were replaced with equimolar amounts of m-145 and D-116 to obtain compound 145 (14.79 g, 73%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 578.2285 (theoretical value: 578.2296). Theoretical elemental content (%) C 42 H 22 D4N2O: C, 87.17; H, 5.22; N, 4.84. Measured elemental content (%): C, 87.12; H, 5.25; N, 4.88.

[0263] Synthesis Example 17: Synthesis of Compound 151

[0264]

[0265] Following the preparation method of Synthesis Example 1, a-2, b'-2, and d-2 were replaced with equimolar amounts of a-151, b'-28, and d-151 to obtain compound 151 (16.53 g, 70%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 674.2346 (theoretical value: 674.2358). Theoretical elemental content (%) C 50 H 30 N2O: C, 89.00; H, 4.48; N, 4.15. Measured elemental content (%): C, 89.05; H, 4.44; N, 4.18.

[0266] Synthesis Example 18: Synthesis of Compound 158

[0267]

[0268] Following the preparation method of Synthesis Example 7, b-91 and D-91 were replaced with equimolar amounts of b-158 and D-158 to obtain compound 158 (15.72 g, 69%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 650.2344 (theoretical value: 650.2358). Theoretical elemental content (%) C 48 H 30 N₂O: C, 88.59; H, 4.65; N, 4.30. Measured elemental content (%): C, 88.54; H, 4.68; N, 4.33.

[0269] Synthesis Example 19: Synthesis of Compound 170

[0270]

[0271] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-170 and b'-35 to obtain compound 170 (14.28 g, 71%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 574.2057 (theoretical value: 574.2045). Theoretical elemental content (%) C 42 H 26 N₂O: C, 87.78; H, 4.56; N, 4.87. Measured elemental content (%): C, 87.83; H, 4.52; N, 4.90.

[0272] Synthesis Example 20: Synthesis of Compound 178

[0273]

[0274] Following the preparation method of Synthesis Example 8, B-101, c-101, and d-101 were replaced with equimolar amounts of B-35, c-178, and d-178 to obtain compound 178 (15.01 g, 74%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 579.2344 (theoretical value: 579.2359). Theoretical elemental content (%) C 42 H 21 D5N2O: C, 87.02; H, 5.39; N, 4.83. Measured elemental content (%): C, 87.07; H, 5.36; N, 4.87.

[0275] Synthesis Example 21: Synthesis of Compound 234

[0276]

[0277] Following the same preparation method as compound 101 in Example 8, E-101 and d-101 were replaced with equimolar amounts of E-178 and d-234 to obtain compound 234 (15.02 g, 76%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 564.1827 (theoretical value: 564.1838). Theoretical elemental content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured elemental content (%): C, 85.04; H, 4.31; N, 4.93.

[0278] Synthesis Example 22: Synthesis of Compound 256

[0279]

[0280] Following the preparation method of Synthesis Example 9, D-104 and d-104 were replaced with equimolar amounts of D-256 and d-256 to obtain compound 256 (16.20 g, 67%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 690.2320 (theoretical value: 690.2307). Theoretical elemental content (%) C 50 H 30 N2O2: C, 86.94; H, 4.38; N, 4.06. Measured elemental content (%): C, 86.99; H, 4.35; N, 4.07.

[0281] Synthesis Example 23: Synthesis of Compound 276

[0282]

[0283] Following the preparation method of Synthesis Example 9, D-104 and d-104 were replaced with equimolar amounts of D-276 and d-276 to obtain compound 276 (16.44 g, 68%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 690.2321 (theoretical value: 690.2307). Theoretical elemental content (%) C 50 H 30 N2O2: C, 86.94; H, 4.38; N, 4.06. Measured elemental content (%): C, 86.99; H, 4.35; N, 4.02.

[0284] Synthesis Example 24: Synthesis of Compound 291

[0285]

[0286] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-291 and d-291 to obtain compound 291 (14.57 g, 77%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 540.1673 (theoretical value: 540.1660). Theoretical elemental content (%) C 38 H 24 N2S: C, 84.41; H, 4.47; N, 5.18. Measured elemental content (%): C, 84.45; H, 4.44; N, 5.22.

[0287] Synthesis Example 25: Synthesis of Compound 323

[0288]

[0289] Following the preparation method of Synthesis Example 1, a-2, b-2, b'-2, and d-2 were replaced with equimolar amounts of a-15, b-323, b'-323, and d-323 to obtain compound 323 (17.52 g, 65%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 769.2564 (theoretical value: 769.2552). Theoretical elemental content (%) C 55 H 35 N3S: C, 85.80; H, 4.58; N, 5.46. Measured elemental content (%): C, 85.85; H, 4.55; N, 5.50.

[0290] Synthesis Example 26: Synthesis of Compound 326

[0291]

[0292] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-326 and d-291 to obtain compound 326 (14.90 g, 78%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 545.1961 (theoretical value: 545.1974). Theoretical elemental content (%) C 38 H 19 D5N2S: C, 83.64; H, 5.35; N, 5.13. Measured elemental content (%): C, 83.69; H, 5.32; N, 5.15.

[0293] Synthesis Example 27: Synthesis of Compound 334

[0294]

[0295] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-334 and d-334 to obtain compound 334 (15.05 g, 76%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 565.1626 (theoretical value: 565.1613). Theoretical elemental content (%) C 39 H 23 N3S: C, 82.81; H, 4.10; N, 7.43. Measured elemental content (%): C, 82.84; H, 4.07; N, 7.47.

[0296] Synthesis Example 28: Synthesis of Compound 339

[0297]

[0298] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-339 and d-339 to obtain compound 339 (15.60 g, 69%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 645.2244 (theoretical value: 645.2259). Theoretical elemental content (%) C 43 H 19 D9N2S2: C, 79.96; H, 5.77; N, 4.34. Measured elemental content (%): C, 79.95; H, 5.80; N, 4.37.

[0299] Synthesis Example 29: Synthesis of Compound 361

[0300]

[0301] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-361 and d-291 to obtain compound 361 (15.03 g, 67%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 640.1959 (theoretical value: 640.1973). Theoretical elemental content (%) C 46 H 28 N2S: C, 86.22; H, 4.40; N, 4.37. Measured elemental content (%): C, 86.27; H, 4.44; N, 4.34.

[0302] Synthesis Example 30: Synthesis of Compound 379

[0303]

[0304] Following the preparation method of Synthesis Example 1, A-2, b'-2, c-2, and d-2 were replaced with equimolar amounts of A-15, b'-323, c-138, and d-379 to obtain compound 379 (16.49 g, 65%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 724.2926 (theoretical value: 724.2912). Theoretical elemental content (%) C 52 H 40 N2S: C, 86.15; H, 5.56; N, 3.86. Measured elemental content (%): C, 86.18; H, 5.52; N, 3.83.

[0305] Synthesis Example 31: Synthesis of Compound 404

[0306]

[0307] Following the preparation method of Synthesis Example 7, m-91, b-91, and D-91 were replaced with equimolar amounts of m-404, b-404, and D-116 to obtain compound 404 (15.45 g, 70%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 630.2143 (theoretical value: 630.2130). Theoretical elemental content (%) C 45 H 30 N2S: C, 85.68; H, 4.79; N, 4.44. Measured elemental content (%): C, 85.72; H, 4.74; N, 4.49.

[0308] Synthesis Example 32: Synthesis of Compound 422

[0309]

[0310] Following the preparation method of Synthesis Example 7, D-91 and M-91 were replaced with equimolar amounts of D-422 and d-422 to obtain compound 422 (14.82 g, 78%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 542.1831 (theoretical value: 542.1817). Theoretical elemental content (%) C 38 H 26 N₂S: C, 84.10; H, 4.83; N, 5.16. Measured elemental content (%): C, 84.12; H, 4.80; N, 5.20.

[0311] Synthesis Example 33: Synthesis of Compound 443

[0312]

[0313] Synthesis of intermediate A-443:

[0314] Under nitrogen protection, a-15 (36.92 g, 150.00 mmol), b-443 (49.50 g, 150.00 mmol), and sodium tert-butoxide (25.95 g, 270.00 mmol) were dissolved in 600 mL of dehydrated toluene. A toluene solution of palladium acetate (0.34 g, 1.50 mmol) and tri-tert-butylphosphine (1.21 g, 6.00 mmol) was added with stirring, and the mixture was refluxed for 5 hours. After cooling, the mixture was filtered through diatomaceous earth / silica gel. The filtrate was purified by vacuum distillation to remove the organic solvent. The concentrate was recrystallized from toluene, and the residue was filtered to obtain intermediate A-443 (55.80 g, 83%). HPLC analysis showed a solid purity ≥99.78%. Mass spectrometry m / z: 447.1021 (theoretical value: 447.1005).

[0315] Synthesis of intermediate B-443:

[0316] Under nitrogen protection, A-443 (53.78 g, 120.00 mmol), b'-323 (31.21 g, 120.00 mmol), potassium carbonate (33.17 g, 240.00 mmol), and Pd(PPh3)4 (1.39 g, 1.20 mmol) were added to a reaction flask, along with 520 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred, and the reaction system was heated under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The resulting solid was recrystallized from toluene to obtain intermediate B-443 (41.99 g, 77%). The purity of the solid was ≥99.81% as determined by HPLC. Mass spectrometry m / z: 453.0173 (theoretical value: 453.0187).

[0317] Synthesis of compound 443:

[0318] Following the preparation method of Synthesis Example 8, B-101, c-101, and d-101 were replaced with equimolar amounts of B-443, c-178, and d-443 to obtain compound 443 (18.06 g, 73%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 706.2431 (theoretical value: 706.2443). Theoretical elemental content (%) C 51 H 34 N2S: C, 86.65; H, 4.85; N, 3.96. Measured elemental content (%): C, 86.70; H, 4.82; N, 3.98.

[0319] Synthesis Example 34: Synthesis of Compound 450

[0320]

[0321] Synthesis of intermediate D-450:

[0322] Under nitrogen protection, D-276 (15.32 g, 50.00 mmol), d-291 (14.46 g, 50.00 mmol), bis(benzylacetone)palladium (0.29 g, 0.50 mmol), and sodium tert-butoxide (9.61 g, 100.00 mmol) were added to 250 mL of xylene solution with stirring. A 50% solution of tri-tert-butylphosphine (1.68 g, 8.30 mmol) was slowly added, and the mixture was refluxed for 6 hours. Recrystallization from chlorobenzene yielded intermediate D-450 (20.59 g, 80%). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 514.1515 (theoretical value: 514.1504).

[0323] Following the preparation method of Synthesis Example 1, D-2 and d-2 were replaced with equimolar amounts of D-450 and d-450 to obtain compound 450 (16.93 g, 64%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 755.2383 (theoretical value: 755.2395). Theoretical elemental content (%) C 54 H 33 N3S: C, 85.80; H, 4.40; N, 5.56. Measured elemental content (%): C, 85.84; H, 4.37; N, 5.60.

[0324] Synthesis Example 35: Synthesis of Compound 505

[0325]

[0326] Following the preparation method of Synthesis Example 1, A-2, b'-2, c-2, and d-2 were replaced with equimolar amounts of A-443, b'-505, c-138, and d-505 to obtain compound 505 (17.23 g, 76%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 647.1479 (theoretical value: 647.1490). Theoretical elemental content (%) C 43 H 25 N3S2: C, 79.73; H, 3.89; N, 6.49. Measured elemental content (%): C, 79.76; H, 3.85; N, 6.52.

[0327] Synthesis Example 36: Synthesis of Compound 567

[0328]

[0329] Following the preparation method of Synthesis Example 33, b-443, b'-323, c-178, and d-443 were replaced with equimolar amounts of b-28, b'-567, c-101, and d-567 to obtain compound 567 (17.63 g, 74%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 680.1937 (theoretical value: 680.1922). Theoretical elemental content (%) C 48 H 28 N₂OS: C, 84.68; H, 4.15; N, 4.11. Measured elemental content (%): C, 84.63; H, 4.19; N, 4.08.

[0330] [Device Example 1]

[0331] The ITO (indium tin oxide) coated glass substrate was cleaned with distilled water and ultrasonically. After distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol. After drying, it was transferred to a plasma cleaner for oxygen plasma cleaning for 10 minutes, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as the anode, compound A was vacuum deposited on the ITO substrate to form a thickness of [missing information]. A hole injection layer. Compound B is deposited on the injection layer, forming a thickness of [missing information]. A hole transport layer was formed. A light-emitting layer was deposited on the hole transport layer, using compound 2 and compound C (mass ratio 5:5) as the host materials and compound D (doped with 5 wt%) as the substrate materials, through vacuum deposition to form a layer with a thickness of [missing information]. The light-emitting layer is then formed. Subsequently, E is deposited on the light-emitting layer to form a layer with a thickness of [missing information]. A hole-blocking layer is formed. F is deposited on the hole-blocking layer to form a thickness of [missing information]. An electron transport layer is formed by vacuum deposition of G on the electron transport layer, resulting in a thickness of [missing information]. An electron-injected layer was formed. Al was then vacuum-deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0332]

[0333] [Device Examples 2-36]

[0334] Compounds 15, 28, 35, 49, 71, 91, 101, 104, 107, 115, 116, 138, 141, 143, 145, 151, 158, 170, 178, 234, 256, 276, 291, 323, 326, 334, 339, 361, 379, 404, 422, 443, 450, 505, and 567 of this invention were used to replace compound 2 in device example 1 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0335] [Comparative Device Example 1]

[0336] The organic electroluminescent device was prepared by replacing compound 2 in device example 1 with compound H-1 as the host material of the light-emitting layer, except that the same preparation method as device example 1 was used.

[0337] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0338] The test environment was atmospheric, and the temperature was room temperature. Table 1 below shows the test results of the luminescence characteristics of devices 1-36 in the device embodiments of this invention, compared to the organic electroluminescent devices obtained in Example 1.

[0339] Table 1:

[0340]

[0341]

[0342] As shown in Table 1, when the carbazole compound described in this invention is used as the main material of the light-emitting layer of an organic electroluminescent device, the device has a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound of this invention is a high-performance light-emitting layer main material.

[0343] [Device Example 37]

[0344] The ITO (indium tin oxide) coated glass substrate was cleaned with distilled water and ultrasonically. After distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol. After drying, it was transferred to a plasma cleaner for oxygen plasma cleaning for 10 minutes, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as the anode, compound H was vacuum deposited on the ITO substrate to form a layer with a thickness of [missing information]. A hole injection layer. Compound I is deposited on the injection layer, forming a thickness of [missing information]. A hole transport layer was formed. A light-emitting layer was deposited on the hole transport layer, using compound 2 and compound J (mass ratio 5:5) as the host materials and compound K (doped with 5 wt%) as the substrate materials, through vacuum deposition to form a layer with a thickness of [missing information]. The light-emitting layer is then deposited. Subsequently, L is deposited on the light-emitting layer to form a layer with a thickness of [missing information]. A hole-blocking layer is formed. F is deposited on the hole-blocking layer to form a thickness of [missing information]. An electron transport layer is formed by vacuum deposition of LiF on the electron transport layer, resulting in a thickness of [missing information]. An electron-injected layer was formed. Al was then vacuum-deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0345]

[0346] [Device Examples 38–72]

[0347] Compounds 15, 28, 35, 49, 71, 91, 101, 104, 107, 115, 116, 138, 141, 143, 145, 151, 158, 170, 178, 234, 256, 276, 291, 323, 326, 334, 339, 361, 379, 404, 422, 443, 450, 505, and 567 of the present invention were used to replace compound 2 in device example 37 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared by the same preparation method as device example 37.

[0348] [Comparative Device Example 2]

[0349] Compound H-1 was used to replace compound 2 in device example 37 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared by the same preparation method as device example 37.

[0350] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0351] The test environment was atmospheric, and the temperature was room temperature. Table 2 below shows the test results of the luminescence characteristics of the organic electroluminescent devices obtained in the device embodiments of the present invention (devices 37-72) and comparative embodiment 2.

[0352] Table 2:

[0353]

[0354]

[0355] As shown in Table 2, when the carbazole compound described in this invention is used as the main material of the light-emitting layer of an organic electroluminescent device, the device has a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound of this invention is a high-performance light-emitting layer main material.

[0356] It should be noted that the present invention has been specifically described with reference to individual embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A carbazole compound, characterized in that, The carbazole compound has the structure represented by Formula I: Wherein, ring A is selected from ; The ring B is selected from chemical formula II, and chemical formula II is obtained through... The site fuses with ring A in chemical formula I; Each of the V values ​​is independently selected from C(R). t Any one of the following; The R t Selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl groups; Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are selected from CH; At least one of Ar1 and Ar2 is selected from any of the following structures: The R3 is independently selected from any one of hydrogen, cyano, substituted or unsubstituted C1 to C6 alkyl groups; The n3 is selected from integers from 0 to 5; when there are two or more R3s, the two or more R3s are the same as or different from each other; The remaining Ar1 and Ar2 are selected from any of the following structures: Z is selected from CH; The same or different R7s are selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; c1 is selected from integers from 0 to 5; c2 is selected from integers from 0 to 4; c3 is selected from integers from 0 to 7; c4 is selected from integers from 0 to 9; c6 is selected from integers from 0 to 11; when there are two or more R7s, the two or more R7s are the same as or different from each other; The R k R l Independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; L1 and L2 are each independently selected from a single bond or from any of the following structures: The R 6a It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1 to C6 alkyl groups; R6 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl groups; b1 is selected from integers from 0 to 4; b2 is selected from integers from 0 to 6; b6 is selected from integers from 0 to 3; when two or more R... 6a At that time, two or more R 6a The same or different between each other, or two adjacent R 6a They can be connected to each other to form substituted or unsubstituted rings: cyclopentane ring, cyclohexane ring; when two or more R6s are present, the two or more R6s may be the same or different from each other; The L mentioned in o Selected from any one of single-bonded, substituted or unsubstituted phenylene; The L mentioned in o Selected from single bonds; R1 and R2 are each independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; The n1 is selected from an integer from 0 to 2; when n1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form substituted or unsubstituted benzene rings; The n2 is selected from integers from 0 to 4; when n2 is greater than 1, two or more R2s are the same or different from each other; The substituents in "substituted or unsubstituted" are independently selected from deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl.

2. The carbazole compound according to claim 1, characterized in that, The carbazole compound is selected from any one of the following structures: 。 3. The carbazole compound according to claim 1, characterized in that, Ar1 and Ar2 are selected from any of the following structures: 。 4. A carbazole compound according to claim 1, characterized in that, the remaining Ar1 and Ar2 are selected from any of the following structures: The R7s, whether identical or different, are selected from either hydrogen or deuterium.

5. A carbazole compound according to claim 1, characterized in that, L1 and L2 are each independently selected from a single bond or from any of the following structures: 。 6. A carbazole compound, characterized in that, The carbazole compound is selected from any one of the following structures: 。 7. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, characterized in that, The organic layer comprises a light-emitting layer, which comprises at least one of the carbazole compounds according to any one of claims 1 to 6.

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