A carbazole compound and an organic electroluminescent device thereof
By using a carbazole compound with a specific structure as the host material in OLED devices, the problem of unbalanced electron and hole distribution is solved, exciton utilization is improved, and the luminous efficiency and stability of the devices are enhanced, making them suitable for industrial applications.
Patent Information
- Application Number
- CN202311100330.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-08-29
- Publication Date
- 2026-06-26
- Estimated Expiration
- 2043-08-29
AI Technical Summary
In existing OLED devices, the distribution of electrons and holes in the emissive layer is unbalanced, resulting in low exciton utilization efficiency and a tendency for aggregation and quenching phenomena, which affect the luminous efficiency and lifespan of the device.
A carbazole compound with a specific chemical structure is used as the host material in the light-emitting layer of OLED devices to improve the balanced distribution of electrons and holes and the breadth of the exciton recombination region.
This compound improves the luminous efficiency of OLED devices, extends their lifespan, and exhibits good stability and film-forming properties, making it suitable for industrial production.
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Abstract
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] With the development of the information age, people have put forward more demands for visual human-computer interaction interfaces (i.e., display devices). Organic light-emitting diodes (OLEDs) have superior characteristics compared to LCDs, including faster response speed, wider color gamut, lower power consumption, larger display screen, and even flexible display capabilities. Moreover, they do not require a backlight to emit light, so their applications in flat panel displays and solid-state lighting have received widespread attention from academia and the business community.
[0003] The classic structure of OLED devices involves inserting an organic functional layer between the cathode and anode, forming a "sandwich"-like structure. With technological advancements, to achieve higher efficiency electroluminescence, the number of intermediate organic functional layers has gradually increased, forming a multilayer structure that includes a hole transport layer (HTL), an emissive layer (EML), and an electron transport layer (ETL).
[0004] Based on the different luminescent materials, devices are classified into doped and undoped luminescent devices. Undoped luminescent devices have a relatively simple fabrication process, but the close proximity of the luminescent material molecules leads to a very high concentration of excited states within the luminescent layer, making them prone to aggregation quenching. Therefore, modern luminescent layers typically employ a host-guest doping structure, where one or more guest luminescent materials are doped into the host material at appropriate concentrations to fabricate monochromatic or white light devices. The advantage of the host-guest doping system is that it effectively avoids exciton quenching caused by close contact between luminescent materials. Furthermore, luminescent layers with mixed materials can exhibit the carrier transport characteristics of different transport materials. By adjusting the material ratios, the transport and distribution balance of carriers within the luminescent layer can be effectively improved, increasing the complex probability of carriers.
[0005] To continuously improve device performance, introducing phosphorescent emitting materials in OLEDs that can simultaneously utilize singlet and triplet excitons for light emission is one of the main ways to improve device luminous efficiency. However, how to design a host material for the emitting layer that achieves a more balanced distribution of electrons and holes within the emitting layer and higher exciton utilization efficiency is a question worth considering. Summary of the Invention
[0006] To address the aforementioned problems, this invention provides a carbazole compound and its organic electroluminescent device. Applying this carbazole compound to an organic light-emitting device can effectively improve the device's luminous efficiency 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 and ring D are each independently selected from any one of the substituted or unsubstituted structures in group 1, and at least one of ring A and ring D is not selected from substituted or unsubstituted structures.
[0012] The ring B is selected from substituted or unsubstituted rings.
[0013] The ring C is selected from chemical formula II, and chemical formula II is fused with ring B in chemical formula I through a * site;
[0014] At least one of Ar1 and Ar2 is selected from Formula III, and the remainder is selected from any one of the following: 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 alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0015] The L0 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups.
[0016] L1 and L2 are each independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.
[0017] X is selected from either O or S;
[0018] Z is selected from either CH or N, and at least two of Z are selected from N;
[0019] The V is selected from C(R) t Any one of N;
[0020] The R1, R t It is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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;
[0021] The a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R1s, the 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.
[0022] The present invention also provides an organic electroluminescent device comprising at least one of the carbazole compounds described in the present invention.
[0023] Beneficial effects
[0024] This invention provides a carbazole compound. When applied to the main material of OLED devices, this compound results in a more balanced distribution of electrons and holes within the light-emitting layer, a wider exciton recombination region, and improved exciton utilization, thus significantly enhancing device efficiency. Furthermore, when applied to organic electroluminescent devices, this compound exhibits good stability and film-forming properties, improving device luminous efficiency and extending device lifespan. The compound's preparation method is simple, the raw materials are readily available, meeting industrialization requirements and demonstrating promising industrialization prospects. Detailed Implementation
[0025] 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.
[0026] 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.
[0027] 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.
[0028] 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.
[0029] For example, Can represent Can represent Can represent And so on.
[0030] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, halogen atom, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, C3-C15 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred groups include deuterium, cyano, halogen, nitro, amino, C1-C12 alkyl, C3-C15 silyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C30 aryl, and C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, cyclopropyl, cyclohexyl, 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, carbazolyl, 9-phenylcarbazolyl, 9,9'-spirodifluorenyl, carbazo-indolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenthiazinyl, phenoxazinyl, acridineyl, pyrroleyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazoleyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, 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.
[0031] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It is classified into straight-chain alkyl and branched-chain alkyl groups, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but are not limited thereto.
[0032] The silane group described in this invention refers to a monovalent group obtained from a silane consisting of a carbon atom and a silicon atom with one hydrogen atom removed, preferably having 3 to 25 carbon atoms, more preferably having 3 to 22 carbon atoms, and most preferably having 3 to 18 carbon atoms. Examples include triphenylsilane, trimethylsilane, triethylsilane, triisopropylsilane, tritert-butylsilane, etc., but are not limited thereto.
[0033] The alicyclic group mentioned in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. It 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. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, norbornyl, etc., but are not limited thereto.
[0034] The alicyclic group described in this invention refers to a divalent group obtained by removing two hydrogen atoms from an alicyclic hydrocarbon molecule, 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. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, norbornyl, cyclopropenyl, etc., but not limited thereto.
[0035] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 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. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto.
[0036] The heterocyclic alkyl group described in this invention refers to a cycloalkyl group obtained by replacing one or more carbon atoms with heteroatoms. The 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. Examples include tetrahydropyrrolyl and piperidinyl, but are not limited thereto.
[0037] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from an aromatic carbon atom in 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 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto. The polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited thereto. The fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, perylene, fluoranyl, spirofluorenyl, spirodifluorenyl, benzo[a]fluorenyl, triphenylene, etc., but not limited thereto.
[0038] The arylene group described in this invention refers to a divalent group obtained by removing two hydrogen atoms from 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. Examples include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorene, fluorenylene, phenylfluorene, pyrene, terphenylene, perylene, etc., but are not limited thereto.
[0039] The heteroaryl group described in this invention refers to an aryl group obtained by replacing one or more aromatic carbon atoms 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. The monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but is not limited thereto; the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinoxalinyl, benzo[a]quinoxalinyl, ortho[a]quinoxalinyl, etc. Phenophenolinyl, spirofluorenoxanthyl, spirofluorenthixanthyl, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxthiayl, benzodibenzofuranyl, benzodibenzothiopheneyl, etc., but not limited to these.
[0040] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms with heteroatoms, wherein 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. The monocyclic and fused-ring heteroaryl groups may include, but are not limited to, phenylfuranyl, benzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, carbazoyl, benzocarbazoyl, dibenzocarbazoyl, pyridyl, pyrimidinyl, triazineyl, etc.; the polycyclic heteroaryl groups may include, but are not limited to, phenylpyridyl, bipyridyl, bipyrimidinyl, etc.
[0041] The fused alicyclic and aromatic cyclic group described in this invention refers to a monovalent group obtained by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, such as benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, etc., but is not limited thereto.
[0042] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to 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, such as benzo[a]cyclopropyl, naphtho[a]cyclopropyl, benzo[a]cyclobutyl, naphtho[a]cyclobutyl, benzo[a]cyclopentyl, naphtho[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclohexyl, etc., but are not limited thereto.
[0043] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to a 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, such as benzo[a]tetrahydropyrrole, benzo[a]piperidinyl, naph[a]piperidinyl, phenanthrenepiperidinyl, benzo[a]azaheterobutyl, benzo[a]azaheteroheptyl, naph[a]tetrahydropyrrole, phenanthrenetetrahydropyrrole, etc., but is not limited thereto.
[0044] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to a monovalent group obtained by removing a hydrogen atom after the 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, such as pyridocyclopropyl, pyrimidocyclopropyl, dibenzofuranocyclopropyl, dibenzothiophenocyclopropyl, carbazoleocyclopropyl, pyridocyclobutyl, pyrimidocyclobutyl, dibenzofuranocyclobutyl, dibenzothiophenocyclobutyl, carbazoleocyclobutyl, pyridocyclopentyl, pyrimidocyclopentyl, dibenzofuranocyclopentyl, dibenzothiophenocyclopentyl, carbazoleocyclopentyl, pyridocyclohexyl, pyrimidocyclohexyl, dibenzofuranocyclohexyl, dibenzothiophenocyclohexyl, carbazoleocyclohexyl, pyridinylbenzocycloheptyl, pyrimidinylbenzocycloheptyl, dibenzofuranocycloheptyl, dibenzothiophenocycloheptyl, carbazoleocycloheptyl, etc., but not limited thereto.
[0045] The fused alicyclic and heteroaromatic ring cyclic groups described in this invention refer to 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, such as pyridinocyclopropyl, pyrimidinocyclopropyl, dibenzofuranocyclopropyl, dibenzothiophenocyclopropyl, carbazocyclopropyl, pyridinocyclobutyl, pyrimidinocyclobutyl, dibenzofuranocyclobutyl, dibenzothiophenocyclobutyl, carbazocyclobutyl, pyridinocyclopentyl, etc. Pyrimidinecyclopentyl, dibenzofuranocyclopentyl, dibenzothiophenecyclopentyl, carbazocyclopentyl, pyrimidinecyclohexyl, pyrimidinecyclohexyl, dibenzofuranocyclohexyl, dibenzothiophenecyclohexyl, carbazocyclohexyl, pyrimidinebenzocyclohepyl, pyrimidinebenzocyclohepyl, dibenzofuranocyclohepyl, dibenzothiophenecyclohepyl, carbazocyclohepyl, etc., but not limited to these.
[0046] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.
[0047] 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:
[0048]
[0049] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.
[0050] This invention provides a carbazole compound having the structure represented by Formula I:
[0051]
[0052] Group 1:
[0053]
[0054] Wherein, ring A and ring D are each independently selected from any one of the substituted or unsubstituted structures in group 1, and at least one of ring A and ring D is not selected from substituted or unsubstituted structures.
[0055] The ring B is selected from substituted or unsubstituted rings.
[0056] The ring C is selected from chemical formula II, and chemical formula II is fused with ring B in chemical formula I through a * site;
[0057] At least one of Ar1 and Ar2 is selected from Formula III, and the remainder is selected from any one of the following: 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 alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0058] The L0 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups.
[0059] L1 and L2 are each independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.
[0060] X is selected from either O or S;
[0061] Z is selected from either CH or N, and at least two of Z are selected from N;
[0062] The V is selected from C(R) t Any one of N;
[0063] The R1, R t It is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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;
[0064] The a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R1s, the 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.
[0065] Preferably, R1, R tEach is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 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 phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 naphridyl, 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.
[0066] Preferably, the substituents in the "substituted or unsubstituted group 1 structure" can be independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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 heteroaromatic ring fused cycloyl group; or adjacent substituents can be connected to form a substituted or unsubstituted ring.
[0067] Preferably, ring A and ring D are each independently selected from any one of the following structures:
[0068]
[0069] Where * represents a fusion site.
[0070] Preferably, the carbazole compound is selected from any one of the following structures:
[0071]
[0072] Preferably, Formula III is selected from any one of the following structures:
[0073]
[0074]
[0075] The R0 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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;
[0076] The z1 is selected from 0, 1, 2, 3, 4 or 5; the z2 is selected from 0, 1, 2, 3 or 4; the z3 is selected from 0, 1, 2 or 3; when there are two or more R0s, the two or more R0s are the same or different from each other, or two adjacent R0s are connected to each other to form a substituted or unsubstituted ring.
[0077] Preferably, R0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, etc. Substituted or unsubstituted benzocycloheptyl, 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 triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 Azolium, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolium, 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 acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.
[0078] More preferably, Formula III is selected from any of the following structures:
[0079]
[0080]
[0081] The R' is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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;
[0082] The number e1 is selected from 0, 1, 2, 3 or 4; the number e2 is selected from 0, 1, 2, 3, 4 or 5; the number e3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the number e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; when there are two or more R's, the two or more R's are the same as or different from each other, or two adjacent R's are connected to each other to form a substituted or unsubstituted ring.
[0083] Preferably, R' is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, etc. Substituted or unsubstituted benzocycloheptyl, 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 triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 Azolium, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolium, 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 acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.
[0084] Preferably, each L0 is independently selected from any of the following structures:
[0085]
[0086] The R5 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 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;
[0087] The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5 or 6; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d4 is selected from 0, 1 or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R5s, the two or more R5s are the same as or different from each other, or two adjacent R5s are connected to each other to form a substituted or unsubstituted ring;
[0088] P is selected from either CH or N;
[0089] The R o It is selected from any one of hydrogen, deuterium, 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.
[0090] Y7, Y8, and Y9 are independently selected from O, S, and C(R). m R n ), N(R p Any one of the following;
[0091] The R m R nEach of the following is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C25 silyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, 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, or R m R n They are connected to form substituted or unsubstituted C3-C7 alicyclic rings;
[0092] The R p It is selected from hydrogen, 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.
[0093] Preferably, R5 is 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 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 phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 naphridyl, 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.
[0094] Preferably, the R oSelected from hydrogen, deuterium, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthyl, etc. Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzodibenzothiophene, 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.
[0095] Preferably, the R m R n R pEach is independently selected from hydrogen, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 spirofluorenyl, substituted or unsubstituted fluoranthyl Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzodibenzothiopheneyl, 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, etc. 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 phenothiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.
[0096] Preferably, at least one of Ar1 and Ar2 is selected from Formula III, and the rest are selected from any one of the following structures:
[0097]
[0098] The R2 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 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;
[0099] a2 is selected from 0, 1, 2, 3, 4 or 5; a3 is selected from 0, 1, 2, 3 or 4; a4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a6 is selected from 0, 1 or 2; a7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a8 is selected from 0, 1, 2 or 3; when there are two or more R2s, the two or more R2s are the same as or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;
[0100] The R a It is selected from any one of hydrogen, deuterium, 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.
[0101] The Y is selected from either CH or N;
[0102] Y1, Y2, and Y3 are each independently selected from O, S, and C(R). b R c ), N(R d Any one of the following;
[0103] The R b R cIndependently selected from any one of the following: hydrogen, 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, or substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R b R c They are connected to form substituted or unsubstituted C3-C7 alicyclic rings;
[0104] The R d It is selected from hydrogen, 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.
[0105] Preferably, R2 is 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 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 phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 naphridyl, 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.
[0106] Preferably, the R aSelected from hydrogen, deuterium, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthyl, etc. Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzodibenzothiophene, 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.
[0107] Preferably, the R b R c R dEach is independently selected from hydrogen, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 spirofluorenyl, substituted or unsubstituted fluoranthyl Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzodibenzothiopheneyl, 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, etc. 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 phenothiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.
[0108] Preferably, in each structure, at most three Ys are selected from N, or at most two Ys are selected from N, or at most one Y is selected from N.
[0109] Preferably, L1 and L2 are each independently selected from a single bond or from any of the following structures:
[0110]
[0111] The R3 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 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;
[0112] The b1 is selected from 0, 1, 2, 3 or 4; the b2 is selected from 0, 1, 2, 3, 4, 5 or 6; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the b4 is selected from 0, 1 or 2; the b5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same as or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;
[0113] The L3 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.
[0114] J is selected from either CH or N;
[0115] The R e It is selected from any one of hydrogen, deuterium, 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.
[0116] Y4, Y5, and Y6 are independently selected from O, S, and C(R). f R g), N(R h Any one of the following;
[0117] The R f R g Each of the following is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C25 silyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, 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, or R f R g They are connected to form substituted or unsubstituted C3-C7 alicyclic rings;
[0118] The R h It is selected from hydrogen, 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.
[0119] Preferably, R3 is 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 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 phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 naphridyl, 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.
[0120] Preferably, the R eSelected from hydrogen, deuterium, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthyl, etc. Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzodibenzothiophene, 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.
[0121] Preferably, the R f R g R hEach is independently selected from hydrogen, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 spirofluorenyl, substituted or unsubstituted fluoranthyl Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzodibenzothiopheneyl, 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, etc. 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 phenothiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.
[0122] More preferably, at least one of Ar1 and Ar2 is selected from Formula III, and the rest are selected from any one of the following structures:
[0123]
[0124] The R4, whether identical or different, 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 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl fused cycloyl groups.
[0125] The c1 is selected from 0, 1, 2, 3, 4, or 5; the c2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; the c7 is selected from 0, 1, 2, or 4; the c8 is selected from 0, 1, or 2; the c9 is selected from 0, 1, 2, or 3; when there are two or more R4s, the two or more R4s are the same as or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;
[0126] K is selected from either CH or N;
[0127] The R i Selected from any one of hydrogen, 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 two R i They connect with each other to form substituted or unsubstituted C3-C7 alicyclic rings;
[0128] The R j It is selected from any one of hydrogen, 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.
[0129] The R k It is selected from any one of hydrogen, deuterium, 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, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups.
[0130] Preferably, R4 is 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 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 phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... 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 benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, 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 naphridyl, 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.
[0131] Preferably, the R kSelected from hydrogen, deuterium, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthyl, etc. Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzodibenzothiophene, 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.
[0132] Preferably, the R i R jEach is independently selected from hydrogen, 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 cycloheptyl, substituted or unsubstituted benzocycloheptyl, 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 spirofluorenyl, substituted or unsubstituted fluoranthyl Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzodibenzothiopheneyl, 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, etc. 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 phenothiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.
[0133] More preferably, at least one of Ar1 and Ar2 is selected from Formula III, and the rest are selected from any one of the following structures:
[0134]
[0135]
[0136] Preferably, in each structure, at most three K are selected from N, or at most two K are selected from N, or at most one K is selected from N.
[0137] Most preferably, the carbazole compound is selected from any one of the following structures:
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161] 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.
[0162] The present invention also provides an organic electroluminescent device comprising at least one of the carbazole compounds described in the present invention.
[0163] 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.
[0164] More preferably, the organic layer comprises a light-emitting layer, which comprises at least one of the carbazole compounds described in this invention.
[0165] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the carbazole compounds described in this invention.
[0166] The anode of this invention is a material with a high work function, and can be a metal with a high redox potential, such as Ag, Pt, or Au. Alternatively, it can be a metal / metal oxide electrode (e.g., Al / Ni / NiOx, Al / PtOx). Conductive mixed metal oxides are also possible, with indium tin oxide (ITO) or indium zinc oxide (IZO) being particularly preferred, but not limited to these.
[0167] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability, such as metalloporphyrin, oligothiophene, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, and conductive polymers based on polyaniline and polythiophene, but not limited thereto.
[0168] The hole transport layer material described in this invention is preferably a material with high hole mobility, such as carbazole derivatives, biphenyl diamine derivatives, triarylamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, etc., but is not limited thereto.
[0169] The luminescent layer material of this invention may comprise a host material (also called a matrix material) and a dopant material (also called a guest material), and may also comprise a matrix material (a mixed matrix system) and / or a system of multiple dopants. Dopants are typically those materials that constitute a smaller proportion of the system, while matrix materials are those materials that constitute a larger proportion. In some cases, the proportion of a single matrix material in the system may be less than the proportion of a single dopant. Besides the carbazole compound provided by this invention, the host material of the luminescent layer may also be selected from naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, pentane derivatives, fluoranthene derivatives, pyrene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited thereto. 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, carbazole derivatives, pyrrole derivatives, indole derivatives, etc.
[0170] The electron transport layer material described in this invention is preferably a material with high electron mobility. The electron transport layer can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, etc., but are not limited to these.
[0171] 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, metal oxides, metal complexes, alkali metals, oxides of alkali metals, alkaline earth metals, oxides of alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, alkali metal salts, and alkaline earth metal salts. Examples include cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, Yb, Tb, etc., but is not limited to these.
[0172] The cathode of this invention is a metal, metal alloy, or multilayer structure with a low work function. The metal alloy or multilayer structure is composed of various metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys composed of alkali metals or alkaline earth metals and silver can also be used, such as alloys composed of magnesium and silver. In the case of a multilayer structure, other metal combinations with relatively high work functions, such as Mg / Ag, Ca / Ag, or Ba / Ag, can also be used, but are not limited to these.
[0173] The coating material described in this invention is preferably a material with a high refractive index, such as Alq3, TPBi, etc., but is not limited thereto.
[0174] 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 and position or number of substituents can be changed according to techniques known in the art.
[0175] [Synthesis Route]
[0176] Preparation of intermediate A:
[0177] Preparation of intermediate B:
[0178] Preparation of Formula IV compounds:
[0179]
[0180] Preparation of compound V:
[0181]
[0182] Xa, Xb, Xc, Xd, Xe, and Xf are each independently selected from any one of Cl, Br, and I; the restrictions on rings A, B, D, Ar1, Ar2, L1, L2, Z, R2, and a3 are the same as those described above.
[0183] Description of raw materials, reagents, and characterization equipment:
[0184] 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 by methods known to those skilled in the art.
[0185] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.
[0186] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.
[0187] [Synthetic Example 1] Synthesis of Compound 1
[0188]
[0189] Preparation of A-1:
[0190] Under nitrogen protection, a-1 (14.81 g, 50.00 mmol), b-1 (14.15 g, 50.00 mmol), potassium carbonate (10.37 g, 75 mmol), and tetraphenylphosphine palladium (0.58 g, 0.50 mmol) were added to a reaction flask, along with 200 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 5 hours. After the reaction was completed, 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, and the solvent was concentrated by rotary evaporation. Crystallization was carried out under cooling, and the solid was filtered. The obtained solid was recrystallized from toluene to give A-1 (12.19 g, 75% yield).
[0191] Synthesis of Compound 1:
[0192] Under nitrogen protection, A-1 (9.75 g, 30.00 mmol), g-1 (11.47 g, 30.00 mmol), copper powder (2.48 g, 39.00 mmol), 18-crown ether-6 (0.79 g, 3.00 mmol), potassium carbonate (4.98 g, 36.00 mmol), and DMF (150 ml) were stirred under reflux for 17 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 1 (13.73 g, 73%). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 626.2119 (theoretical value: 626.2107). Theoretical elemental content (%) C 44 H 26 N4O: C, 84.33; H, 4.18; N, 8.94. Measured elemental content (%): C, 84.35; H, 4.15; N, 8.92.
[0193] [Synthetic Example 2] Synthesis of Compound 84
[0194]
[0195] Preparation of A-1:
[0196] Under nitrogen protection, a-1 (38.50 g, 130.00 mmol), b-1 (36.78 g, 130.00 mmol), potassium carbonate (26.95 g, 195 mmol), and tetraphenylphosphine palladium (1.50 g, 1.30 mmol) were added to a reaction flask, along with 550 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 4 hours. After the reaction was completed, 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, 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 give A-1 (37.20 g, yield 88%); HPLC analysis showed that the solid purity was ≥99.61%.
[0197] Preparation of B-84:
[0198] Under nitrogen protection, c-84 (14.81 g, 50.00 mmol), d-84 (12.08 g, 50.00 mmol), potassium carbonate (10.37 g, 75 mmol), and tetraphenylphosphine palladium (0.58 g, 0.50 mmol) were added to a reaction flask, along with 200 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred, and the reaction system was heated under reflux for 4.5 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, 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 give B-84 (14.39 g, yield 87%); HPLC analysis showed that the solid purity was ≥99.64%.
[0199] Preparation of C-84:
[0200] Under nitrogen protection, e-84 (27.69 g, 110.00 mmol), A-1 (53.65 g, 165.00 mmol), copper powder (10.49 g, 165.00 mmol), potassium carbonate (45.61 g, 330.00 mmol), 18-crown-6 (2.29 g, 8.65 mmol), and 1,2-dichlorobenzene (1500 ml) were added to a reaction flask, and the mixture was stirred under reflux for 5.5 hours. After the reaction was complete, distilled water was added first, followed by extraction with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Recrystallization from toluene yielded C-84 (46.37 g, 85% yield); HPLC analysis showed a solid purity ≥ 99.68%.
[0201] Preparation of D-84:
[0202] Under nitrogen protection, C-84 (44.64 g, 90.00 mmol), pinacol diborate (22.85 g, 90.00 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.33 g, 0.45 mmol), potassium acetate (17.67 g, 180.00 mmol), and DMF (450 ml) were added to a reaction flask and stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene:ethanol = 3:1 to obtain D-84 (43.36 g, 82%); the purity of the solid was ≥99.73% as determined by HPLC.
[0203] Preparation of E-84:
[0204] Under nitrogen protection, D-84 (41.12 g, 70.00 mmol), f-84 (14.14 g, 70.00 mmol), tetrakis(triphenylphosphine)palladium (0.81 g, 0.70 mmol), potassium carbonate (19.35 g, 140.00 mmol), THF (300 ml), and water (150 ml) were added to a reaction flask, and the mixture was stirred under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene:n-hexane in a 4:1 ratio to obtain E-84 (31.00 g, 76%). HPLC analysis showed that the solid purity was ≥99.79%.
[0205] F-84 preparation:
[0206] Under nitrogen protection, E-84 (29.13 g, 50.00 mmol), triphenylphosphine (32.7 g, 125.00 mmol), and o-dichlorobenzene (300 ml) were added to a reaction flask, and the mixture was stirred under reflux for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from ethyl acetate:n-hexane = 6:1 to obtain F-84 (20.10 g, 73%). HPLC analysis showed that the solid purity was ≥99.86%.
[0207] Preparation of compound 84:
[0208] Under nitrogen protection, F-84 (16.52 g, 30.00 mmol), B-84 (9.92 g, 30.00 mmol), copper powder (2.48 g, 39.00 mmol), 18-crown ether-6 (0.79 g, 3.00 mmol), potassium carbonate (4.98 g, 36.00 mmol), and DMF (150 ml) were stirred under reflux for 17 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 84 (16.73 g, 66%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 844.2574 (theoretical value: 844.2587). Theoretical elemental content (%) C 58 H 32 N6O2: C, 82.45; H, 3.82; N, 9.95. Measured elemental content (%): C, 82.42; H, 3.83; N, 9.96.
[0209] [Synthetic Example 3] Synthesis of Compound 89
[0210]
[0211] According to the preparation method in Synthesis Example 2, equimolar amounts of b-1, e-84, and B-84 were replaced with equimolar amounts of b-89, e-89, and B-89, respectively, to obtain compound 89 (16.91 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 866.3061 (theoretical value: 866.3046). Theoretical elemental content (%) C 63 H 38 N4O: C, 87.27; H, 4.42; N, 6.46. Measured elemental content (%): C, 87.26; H, 4.46; N, 6.47.
[0212] [Synthetic Example 4] Synthesis of Compound 109
[0213]
[0214] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-109, b-109, and g-109, respectively, to obtain compound 109 (14.83 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 726.2408 (theoretical value: 726.2420). Theoretical elemental content (%) C 52 H 30N4O: C, 85.93; H, 4.16; N, 7.71. Measured elemental content (%): C, 85.96; H, 4.14; N, 7.72.
[0215] [Synthetic Example 5] Synthesis of Compound 124
[0216]
[0217] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-124 and g-109, respectively, to obtain compound 124 (14.55 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2434 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.43; H, 4.34; N, 7.98.
[0218] [Synthetic Example 6] Synthesis of Compound 134
[0219]
[0220] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-134, b-134, and g-109, respectively, to obtain compound 134 (16.93 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 867.2983 (theoretical value: 867.2998). Theoretical elemental content (%) C 62 H 37 N5O: C, 85.79; H, 4.30; N, 8.07. Measured elemental content (%): C, 85.75; H, 4.32; N, 8.06.
[0221] [Synthetic Example 7] Synthesis of Compound 139
[0222]
[0223] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1 and g-1 were replaced with equimolar amounts of a-139 and g-109, respectively, to obtain compound 139 (16.22 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 818.3057 (theoretical value: 818.3046). Theoretical elemental content (%) C 59 H 38 N4O: C, 86.53; H, 4.68; N, 6.84. Measured elemental content (%): C, 86.52; H, 4.65; N, 6.86.
[0224] [Synthetic Example 8] Synthesis of Compound 147
[0225]
[0226] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84 and B-84 were replaced with equimolar amounts of e-147 and B-147, respectively, to obtain compound 147 (15.62 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 776.2591 (theoretical value: 776.2576). Theoretical elemental content (%) C 56 H 32 N4O: C, 86.58; H, 4.15; N, 7.21. Measured elemental content (%): C, 86.59; H, 4.13; N, 7.25.
[0227] [Synthetic Example 9] Synthesis of Compound 150
[0228]
[0229] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, and B-84 were replaced with equimolar amounts of e-147, A-89, and B-150, respectively, to obtain compound 150 (15.15 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 742.2352 (theoretical value: 742.2369). Theoretical elemental content (%) C 52 H 30 N4O2: C, 84.08; H, 4.07; N, 7.54. Measured elemental content (%): C, 84.06; H, 4.04; N, 7.56.
[0230] [Synthetic Example 10] Synthesis of Compound 162
[0231]
[0232] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, and B-84 were replaced with equimolar amounts of e-147, A-162, and B-162, respectively, to obtain compound 162 (16.75 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 858.3346 (theoretical value: 858.3359). Theoretical elemental content (%) C 62 H 42 N4O: C, 86.69; H, 4.93; N, 6.52. Measured elemental content (%): C, 86.66; H, 4.95; N, 6.56.
[0233] [Synthetic Example 11] Synthesis of Compound 172
[0234]
[0235] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-172, b-89, and g-172, respectively, to obtain compound 172 (14.14 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 654.2435 (theoretical value: 654.2420). Theoretical elemental content (%) C 46 H 30 N4O: C, 84.38; H, 4.62; N, 8.56. Measured elemental content (%): C, 84.35; H, 4.63; N, 8.53.
[0236] [Synthetic Example 12] Synthesis of Compound 173
[0237]
[0238] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-173, A-89, f-173, and B-173, respectively, to obtain compound 173 (14.68 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 698.2513 (theoretical value: 698.2502). Theoretical elemental content (%) C 47 H 34 N4OSi: C, 80.77; H, 4.90; N, 8.02. Measured elemental content (%): C, 80.75; H, 4.93; N, 8.05.
[0239] [Synthetic Example 13] Synthesis of Compound 185
[0240]
[0241] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-185, b-185, and g-172, respectively, to obtain compound 185 (14.83 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 726.2402 (theoretical value: 726.2420). Theoretical elemental content (%) C 52 H 30 N4O: C, 85.93; H, 4.16; N, 7.71. Measured elemental content (%): C, 85.97; H, 4.13; N, 7.72.
[0242] [Synthetic Example 14] Synthesis of Compound 191
[0243]
[0244] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-191 and g-172, respectively, to obtain compound 191 (14.55 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2436 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.48; H, 4.32; N, 7.96.
[0245] [Synthetic Example 15] Synthesis of Compound 197
[0246]
[0247] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-197 and g-172, respectively, to obtain compound 197 (14.34 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 702.2433 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.41; H, 4.32; N, 7.94.
[0248] [Synthetic Example 16] Synthesis of Compound 199
[0249]
[0250] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-173, A-197, f-173, and B-199, respectively, to obtain compound 199 (16.57 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 836.3527 (theoretical value: 836.3515). Theoretical elemental content (%) C 60 H 44 N4O: C, 86.10; H, 5.30; N, 6.69. Measured elemental content (%): C, 86.12; H, 5.31; N, 6.67.
[0251] [Synthetic Example 17] Synthesis of Compound 200
[0252]
[0253] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-197 and g-200, respectively, to obtain compound 200 (14.65 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 707.2747 (theoretical value: 707.2733). Theoretical elemental content (%) C 50 H 25 D5N4O: C, 84.84; H, 4.98; N, 7.92. Measured elemental content (%): C, 84.81; H, 4.96; N, 7.96.
[0254] [Synthetic Example 18] Synthesis of Compound 201
[0255]
[0256] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-201, b-201, and g-172, respectively, to obtain compound 201 (14.42 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 706.2679 (theoretical value: 706.2671). Theoretical elemental content (%) C 50 H 26 D4N4O: C, 84.96; H, 4.85; N, 7.93. Measured elemental content (%): C, 84.93; H, 4.84; N, 7.95.
[0257] [Synthetic Example 19] Synthesis of Compound 202
[0258]
[0259] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-162 and g-172, respectively, to obtain compound 202 (14.97 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 702.2431 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.46; H, 4.32; N, 7.95.
[0260] [Synthetic Example 20] Synthesis of Compound 203
[0261]
[0262] According to the preparation method in Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-201, b-203, and g-172, respectively, to obtain compound 203 (14.63 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 706.2689 (theoretical value: 706.2671). Theoretical elemental content (%) C 50 H 26 D4N4O: C, 84.96; H, 4.85; N, 7.93. Measured elemental content (%): C, 84.97; H, 4.82; N, 7.96.
[0263] [Synthetic Example 21] Synthesis of Compound 204
[0264]
[0265] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-173, A-162, f-173, and B-204, respectively, to obtain compound 204 (14.70 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 720.2339 (theoretical value: 720.2325). Theoretical elemental content (%) C 50 H 29 FN4O: C, 83.32; H, 4.06; N, 7.77. Measured elemental content (%): C, 83.34; H, 4.03; N, 7.74.
[0266] [Synthetic Example 22] Synthesis of Compound 209
[0267]
[0268] According to the preparation method in Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-201, b-209, and g-172, respectively, to obtain compound 209 (15.25 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 758.2941 (theoretical value: 758.2953). Theoretical elemental content (%) C 54 H 26 D6N4O: C, 85.46; H, 5.05; N, 7.38. Measured elemental content (%): C, 85.43; H, 5.07; N, 7.36.
[0269] [Synthetic Example 23] Synthesis of Compound 216
[0270]
[0271] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-216 and g-172, respectively, to obtain compound 216 (14.55 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2429 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.41; H, 4.32; N, 7.96.
[0272] [Synthetic Example 24] Synthesis of Compound 217
[0273]
[0274] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-216 and g-217, respectively, to obtain compound 217 (14.58 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 714.3189 (theoretical value: 714.3173). Theoretical elemental content (%) C 50 H 18 D 12 N4O: C, 84.01; H, 5.92; N, 7.84. Measured elemental content (%): C, 84.04; H, 5.91; N, 7.86.
[0275] [Synthetic Example 25] Synthesis of Compound 218
[0276]
[0277] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-216 and g-218, respectively, to obtain compound 218 (14.65 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 707.2745 (theoretical value: 707.2733). Theoretical elemental content (%) C 50 H 25 D5N4O: C, 84.84; H, 4.98; N, 7.92. Measured elemental content (%): C, 84.81; H, 4.96; N, 7.93.
[0278] [Synthetic Example 26] Synthesis of Compound 221
[0279]
[0280] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-221 and g-172, respectively, to obtain compound 221 (14.97 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 702.2404 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.43; H, 4.34; N, 7.98.
[0281] [Synthetic Example 27] Synthesis of Compound 231
[0282]
[0283] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-231, b-231, and g-172, respectively, to obtain compound 231 (14.57 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 703.2385 (theoretical value: 703.2372). Theoretical elemental content (%) C 49 H 29 N5O: C, 83.62; H, 4.15; N, 9.95. Measured elemental content (%): C, 83.66; H, 4.14; N, 9.97.
[0284] [Synthetic Example 28] Synthesis of Compound 244
[0285]
[0286] According to the preparation method in Example 1, equimolar amounts of a-1 and g-1 were replaced with equimolar amounts of a-244 and g-172, respectively, to obtain compound 244 (15.36 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 752.2563 (theoretical value: 752.2576). Theoretical elemental content (%) C 54 H 32 N4O: C, 86.15; H, 4.28; N, 7.44. Measured elemental content (%): C, 86.16; H, 4.25; N, 7.43.
[0287] [Synthetic Example 29] Synthesis of Compound 260
[0288]
[0289] According to the preparation method in Synthesis Example 2, equimolar amounts of F-84 and B-84 were replaced with equimolar amounts of F-173 and B-260, respectively, to obtain compound 260 (15.13 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 752.2562 (theoretical value: 752.2576). Theoretical elemental content (%) C 54 H 32 N4O: C, 86.15; H, 4.28; N, 7.44. Measured elemental content (%): C, 86.17; H, 4.25; N, 7.41.
[0290] [Synthetic Example 30] Synthesis of Compound 270
[0291]
[0292] According to the preparation method in Synthesis Example 2, equimolar amounts of a-1, e-84, f-84, and B-84 were replaced with equimolar amounts of a-270, e-270, f-173, and B-270, respectively, to obtain compound 270 (17.22 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 896.2624 (theoretical value: 896.2610). Theoretical elemental content (%) C 63 H 36 N4OS: C, 84.35; H, 4.05; N, 6.25. Measured elemental content (%): C, 84.33; H, 4.06; N, 6.28.
[0293] [Synthetic Example 31] Synthesis of Compound 280
[0294]
[0295] According to the preparation method in Synthesis Example 2, equimolar amounts of b-1, e-84, f-84, and B-84 were replaced with equimolar amounts of b-280, e-270, f-173, and B-280, respectively, to obtain compound 280 (17.26 g); HPLC purity ≥99.92%. Mass spectrometry m / z: 884.3527 (theoretical value: 884.3515). Theoretical elemental content (%) C 64 H 44 N4O: C, 86.85; H, 5.01; N, 6.33. Measured elemental content (%): C, 86.86; H, 5.03; N, 6.31.
[0296] [Synthetic Example 32] Synthesis of Compound 283
[0297]
[0298] According to the preparation method in Synthesis Example 2, equimolar amounts of F-84 and B-84 were replaced with equimolar amounts of F-199 and B-283, respectively, to obtain compound 283 (15.70 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 780.2626 (theoretical value: 780.2638). Theoretical elemental content (%) C 54 H 32 N6O: C, 83.06; H, 4.13; N, 10.76. Measured elemental content (%): C, 83.05; H, 4.16; N, 10.78.
[0299] [Synthetic Example 33] Synthesis of Compound 292
[0300]
[0301] According to the preparation method in Synthesis Example 2, equimolar amounts of F-84 and B-84 were replaced with equimolar amounts of F-199 and B-292, respectively, to obtain compound 292 (16.02 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 808.2285 (theoretical value: 808.2297). Theoretical elemental content (%) C 56 H 32 N4OS: C, 83.15; H, 3.99; N, 6.93. Measured elemental content (%): C, 83.13; H, 3.95; N, 6.95.
[0302] [Synthetic Example 34] Synthesis of Compound 313
[0303]
[0304] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-313, A-162, f-313, and B-313, respectively, to obtain compound 313 (16.14 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 802.2745 (theoretical value: 802.2733). Theoretical elemental content (%) C 58 H 34 N4O: C, 86.76; H, 4.27; N, 6.98. Measured elemental content (%): C, 86.73; H, 4.28; N, 6.95.
[0305] [Synthetic Example 35] Synthesis of Compound 319
[0306]
[0307] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-197 and g-319, respectively, to obtain compound 319 (14.55 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2429 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.48; H, 4.32; N, 7.94.
[0308] [Synthetic Example 36] Synthesis of Compound 357
[0309]
[0310] According to the preparation method in Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-357, b-357, and g-357, respectively, to obtain compound 357 (15.36 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 752.2588 (theoretical value: 752.2576). Theoretical elemental content (%) C 54 H 32 N4O: C, 86.15; H, 4.28; N, 7.44. Measured elemental content (%): C, 86.18; H, 4.26; N, 7.45.
[0311] [Synthetic Example 37] Synthesis of Compound 380
[0312]
[0313] According to the preparation method in Synthesis Example 1, equimolar amounts of g-1 were replaced with equimolar amounts of g-380 to obtain compound 380 (14.01 g); HPLC purity ≥99.94%. Mass spectrometry m / z: 676.2276 (theoretical value: 676.2263). Theoretical elemental content (%) C 48 H 28 N4O: C, 85.19; H, 4.17; N, 8.28. Measured elemental content (%): C, 85.17; H, 4.18; N, 8.25.
[0314] [Synthetic Example 38] Synthesis of Compound 389
[0315]
[0316] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-313, A-89, f-389, and B-389, respectively, to obtain compound 389 (13.56 g); HPLC purity ≥99.98%. Mass spectrometry m / z: 627.2046 (theoretical value: 627.2059). Theoretical elemental content (%) C 43 H 25 N5O: C, 82.28; H, 4.01; N, 11.16. Measured elemental content (%): C, 82.26; H, 4.04; N, 11.18.
[0317] [Synthetic Example 39] Synthesis of Compound 453
[0318]
[0319] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-216 and g-453, respectively, to obtain compound 453 (14.55 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2435 (theoretical value: 702.2420). Theoretical elemental content (%) C 50 H 30 N4O: C, 85.45; H, 4.30; N, 7.97. Measured elemental content (%): C, 85.46; H, 4.34; N, 7.95.
[0320] [Synthetic Example 40] Synthesis of Compound 494
[0321]
[0322] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-494 and g-494, respectively, to obtain compound 494 (15.98 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 794.2518 (theoretical value: 794.2504). Theoretical elemental content (%) C 56 H 34 N4S: C, 84.61; H, 4.31; N, 7.05. Measured elemental content (%): C, 84.65; H, 4.32; N, 7.02.
[0323] [Synthetic Example 41] Synthesis of Compound 554
[0324]
[0325] According to the preparation method in Synthesis Example 2, equimolar amounts of a-1, b-1, e-84, and B-84 were replaced with equimolar amounts of a-554, b-203, e-554, and B-554, respectively, to obtain compound 554 (15.56 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 762.2773 (theoretical value: 762.2755). Theoretical elemental content (%) C 53 H 30 D4N4S: C, 83.44; H, 5.02; N, 7.34. Measured elemental content (%): C, 83.41; H, 5.06; N, 7.35.
[0326] [Synthetic Example 42] Synthesis of Compound 573
[0327]
[0328] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-494 and g-172, respectively, to obtain compound 573 (14.88 g); HPLC purity ≥99.96%. Mass spectrometry m / z: 718.2178 (theoretical value: 718.2191). Theoretical elemental content (%) C 50 H 30 N4S: C, 83.54; H, 4.21; N, 7.79. Measured elemental content (%): C, 83.56; H, 4.26; N, 7.75.
[0329] [Synthetic Example 43] Synthesis of Compound 575
[0330]
[0331] According to the preparation method in Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-494 and g-575, respectively, to obtain compound 575 (15.58 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 774.2829 (theoretical value: 774.2817). Theoretical elemental content (%) C 54 H 38 N4S: C, 83.69; H, 4.94; N, 7.23. Measured elemental content (%): C, 83.67; H, 4.97; N, 7.26.
[0332] [Synthetic Example 44] Synthesis of Compound 578
[0333]
[0334] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-578 and g-172, respectively, to obtain compound 578 (14.88 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 718.2179 (theoretical value: 718.2191). Theoretical elemental content (%) C 50 H 30 N4S: C, 83.54; H, 4.21; N, 7.79. Measured elemental content (%): C, 83.55; H, 4.24; N, 7.76.
[0335] [Synthetic Example 45] Synthesis of Compound 581
[0336]
[0337] According to the preparation method in Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-581, b-203, and g-172, respectively, to obtain compound 581 (14.96 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 722.2431 (theoretical value: 722.2442). Theoretical elemental content (%) C 50 H 26 D4N4S: C, 83.07; H, 4.74; N, 7.75. Measured elemental content (%): C, 83.05; H, 4.75; N, 7.73.
[0338] [Synthetic Example 46] Synthesis of Compound 583
[0339]
[0340] According to the preparation method in Synthesis Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-583, b-89, and g-172, respectively, to obtain compound 583 (14.77 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 723.2519 (theoretical value: 723.2505). Theoretical elemental content (%) C 50 H 25 D5N4S: C, 82.96; H, 4.87; N, 7.74. Measured elemental content (%): C, 82.93; H, 4.85; N, 7.77.
[0341] [Synthetic Example 47] Synthesis of Compound 588
[0342]
[0343] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-588 and g-172, respectively, to obtain compound 588 (15.31 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 718.2176 (theoretical value: 718.2191). Theoretical elemental content (%) C 50 H 30 N4S: C, 83.54; H, 4.21; N, 7.79. Measured elemental content (%): C, 83.55; H, 4.24; N, 7.78.
[0344] [Synthetic Example 48] Synthesis of Compound 594
[0345]
[0346] According to the preparation method in Synthesis Example 1, equimolar amounts of A-1 and g-1 were replaced with equimolar amounts of A-594 and g-172, respectively, to obtain compound 594 (14.88 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 718.2177 (theoretical value: 718.2191). Theoretical elemental content (%) C 50 H 30 N4S: C, 83.54; H, 4.21; N, 7.79. Measured elemental content (%): C, 83.55; H, 4.25; N, 7.76.
[0347] [Synthetic Example 49] Synthesis of Compound 606
[0348]
[0349] According to the preparation method in Example 1, equimolar amounts of a-1, b-1, and g-1 were replaced with equimolar amounts of a-554, b-89, and g-606, respectively, to obtain compound 606 (15.10 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 718.2179 (theoretical value: 718.2191). Theoretical elemental content (%) C 50 H 30 N4S: C, 83.54; H, 4.21; N, 7.79. Measured elemental content (%): C, 83.57; H, 4.22; N, 7.76.
[0350] [Synthetic Example 50] Synthesis of Compound 608
[0351]
[0352] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-173, A-606, f-173, and B-608, respectively, to obtain compound 608 (15.16 g); HPLC purity ≥99.95%. Mass spectrometry m / z: 742.2172 (theoretical value: 742.2191). Theoretical elemental content (%) C 52 H 30 N4S: C, 84.07; H, 4.07; N, 7.54. Measured elemental content (%): C, 84.03; H, 4.06; N, 7.56.
[0353] [Synthetic Example 51] Synthesis of Compound 631
[0354]
[0355] According to the preparation method in Synthesis Example 2, equimolar amounts of e-84, A-1, f-84, and B-84 were replaced with equimolar amounts of e-631, A-578, f-173, and B-631, respectively, to obtain compound 631 (17.24 g); HPLC purity ≥99.92%. Mass spectrometry m / z: 883.2786 (theoretical value: 883.2770). Theoretical elemental content (%) C 62 H 37 N5S: C, 84.23; H, 4.22; N, 7.92. Measured elemental content (%): C, 84.27; H, 4.24; N, 7.91.
[0356] [Synthetic Example 52] Synthesis of Compound 641
[0357]
[0358] According to the preparation method in Example 1, equimolar amounts of a-1 and g-1 were replaced with equimolar amounts of a-641 and g-641, respectively, to obtain compound 641 (13.88 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 642.1861 (theoretical value: 642.1878). Theoretical elemental content (%) C 44 H 26 N4S: C, 82.22; H, 4.08; N, 8.72. Measured elemental content (%): C, 82.27; H, 4.04; N, 8.73.
[0359] [Device Example 1]
[0360] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. An anode was formed on the substrate with the reflective layer using indium tin oxide (ITO). m-MTDATA was vacuum-deposited on the anode to form a hole injection layer (HIL) with a thickness of [missing information]. β-NPB is deposited on the hole injection layer to form the first hole transport layer, with a thickness of [missing information]. TCBPA was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of [thickness missing]. On the second hole transport layer, a mixed component with the composition of compound 1:Hn:Ir(ppy)2(acac) = 47%:47%:6% was co-deposited to form a green light-emitting layer (EML) with a thickness of [missing information]. On the light-emitting layer, NBphen and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition to form an electron transport layer (ETL) with a thickness of [missing information]. An electron injection layer (EIL) is formed by evaporating LiF onto the electron transport layer, with a thickness of [missing information]. Magnesium (Mg) and silver (Ag) are mixed at a evaporation rate of 1:9 on the electron injection layer and vacuum-deposited to form a cathode with a thickness of [thickness missing]. CP is deposited on the cathode to form an organic capping layer (CPL) with a thickness of [missing information]. This completes the fabrication of organic light-emitting devices.
[0361]
[0362]
[0363] [Device Examples 2-52]
[0364] Compounds 84, 89, 109, 124, 134, 139, 147, 150, 162, 172, 173, 185, 191, 197, 199, 200, 201, 202, 203, 204, 209, 216, 217, 218, 221, 231, 244, 260, and 270 of this invention are used. Compounds 280, 283, 292, 313, 319, 357, 380, 389, 453, 494, 554, 573, 575, 578, 581, 583, 588, 594, 606, 608, 631, and 641 were used to replace compound 1 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 in device example 1.
[0365] [Comparative Device Examples 1-5]
[0366] Compounds H-1, H-2, H-3, H-4, and H-5 were used to replace compound 1 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.
[0367] 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.
[0368] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-52 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-5, are shown in Table 1 below.
[0369] Table 1:
[0370]
[0371]
[0372]
[0373] As shown in Table 1, when the carbazole compound described in this invention is applied to the light-emitting layer host material of organic electroluminescent devices, the devices have higher luminous efficiency and longer service life. The compound of this invention is a high-performance light-emitting layer host material.
[0374] [Device Example 53]
[0375] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. An anode was formed on the substrate with the reflective layer using indium tin oxide (ITO). m-MTDATA was vacuum-deposited on the anode to form a hole injection layer (HIL) with a thickness of [missing information]. An α-NPD is deposited on the hole injection layer to form the first hole transport layer, with a thickness of [missing information]. HMTPD was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of [thickness missing]. On the second hole transport layer, a mixed component consisting of compound 1:Hn:Ir(piq)3 = 46%:46%:8% was co-deposited to form a red luminescent layer (EML) with a thickness of [missing information]. On the light-emitting layer, NBphen and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition to form an electron transport layer (ETL) with a thickness of [missing information]. An electron injection layer (EIL) is formed by evaporating LiF onto the electron transport layer, with a thickness of [missing information]. Magnesium (Mg) and silver (Ag) are mixed at a evaporation rate of 1:9 on the electron injection layer and vacuum-deposited to form a cathode with a thickness of [thickness missing]. CP is deposited on the cathode to form an organic capping layer (CPL) with a thickness of [missing information]. This completes the fabrication of organic light-emitting devices.
[0376]
[0377] [Device Examples 54-104]
[0378] Using compounds 84, 89, 109, 124, 134, 139, 147, 150, 162, 172, 173, 185, 191, 197, 199, 200, 201, 202, 203, 204, 209, 216, 217, 218, 221, 231, 244, 260, 270, and 2... Compounds 283, 292, 313, 319, 357, 380, 389, 453, 494, 554, 573, 575, 578, 581, 583, 588, 594, 606, 608, 631, and 641 were used to replace compound 1 in device example 53 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 53.
[0379] [Comparative Device Examples 6-10]
[0380] Compounds H-1, H-2, H-3, H-4, and H-5 were used to replace compound 1 in device example 55 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 55.
[0381] 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.
[0382] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 53-104 in the device embodiments of this invention, and those obtained in comparative embodiments 6-10, are shown in Table 2 below.
[0383] Table 2:
[0384]
[0385]
[0386]
[0387] As shown in Table 2, when the carbazole compound described in this invention is applied to the light-emitting layer host material of organic electroluminescent devices, the devices have higher luminous efficiency and longer service life. The compound of this invention is a high-performance light-emitting layer host material.
[0388] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.
Claims
1. A carbazole compound, characterized in that, The carbazole compound has the structure represented by Formula I: Ring A and ring D are each independently selected from any of the following structures: And at least one of rings A and D is not selected from ; in, These are confluence sites; The ring B is selected from ; The ring C is selected from chemical formula II, and chemical formula II is obtained through... The site fuses with ring B in chemical formula I; At least one of Ar1 and Ar2 is selected from Formula III, and the rest are selected from any of the following structures: The R 4a It is selected from any one of hydrogen, deuterium, tritium, 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 cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, and substituted or unsubstituted tritert-butylsilyl. The R4 is selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, and substituted or unsubstituted tert-butyl. c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, 3, or 4; when there are two or more R... 4a At that time, two or more R 4a They may be the same as or different from each other; when there are two or more R4s, they may be the same as or different from each other. The K1 is selected from either CH or N, and at most two K1s are selected from N; The K is selected from CH; The R i Selected from hydrogen, substituted or unsubstituted C1-C6 alkyl groups, and substituted or unsubstituted C6-C12 aryl groups; The R j Selected from any one of hydrogen, substituted or unsubstituted C6-C12 aryl groups; Formula III is selected from any of the following structures: The R0 is selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, and substituted or unsubstituted tert-butyl. The z1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R0s, the two or more R0s are the same as or different from each other; The R' is selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, and substituted or unsubstituted tert-butyl. The value of e1 is selected from 0, 1, 2, 3 or 4; the value of e2 is selected from 0, 1, 2, 3, 4 or 5; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R', the two or more R' are the same as or different from each other; Each L0 is independently selected from any of the following structures: R5 is selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1 to C6 alkyl groups; The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5 or 6; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R5s, the two or more R5s are the same as or different from each other; The P mentioned above is selected from CH; The P mentioned herein is selected from either CH or N; The Y7 is selected from N(R) p ); The R p Selected from substituted or unsubstituted C6-C12 aryl groups; L1 and L2 are each independently selected from any one of single-bonded, substituted or unsubstituted phenylene; X is selected from either O or S; Rings A and D and Ring B The V mentioned in the text is selected from C(R) t ); Rings A and D The V mentioned in the text is selected from C(R) t Any one of N; The R t Selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C6 alkyl groups; The substituents in "substituted or unsubstituted" may be independently selected from deuterium, fluorine, chlorine, bromine, iodine, 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, Formula III is selected from any of the following structures: 。 4. A carbazole compound according to claim 1, characterized in that, At least one of Ar1 and Ar2 is selected from Formula III, and the rest are selected from any of the following structures: The R 4a Selected from any one of hydrogen, deuterium, and tritium; The R4 is selected from any one of hydrogen, deuterium, and tritium; K1 is selected from CH.
5. A carbazole compound, characterized in that, The compound is selected from any of the following structures: 。 6. An organic electroluminescent device, characterized in that, It includes at least one of the carbazole compounds according to any one of claims 1 to 5.
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 at least one of the carbazole compounds according to any one of claims 1 to 5.
8. An organic electroluminescent device according to claim 7, characterized in that, The organic layer includes a light-emitting layer, which contains at least one of the carbazole compounds according to any one of claims 1 to 5.
Citation Information
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