A fused ring indolocarbazole compound and an organic electroluminescent device thereof

Abstract

The application provides a fused ring indolocarbazole compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The fused ring indolocarbazole compound shown in formula 1 has good stability and high triplet energy level and the like, can more effectively limit triplet excitons in a guest material, and inhibit the back transmission process of energy from the guest material to a host material, and when the compound is used as a light-emitting layer host material in an organic electroluminescent device, the performance of the device can be effectively improved, specifically, the driving voltage of the device is reduced, the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

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

[0002] OLED (Organic Light-Emitting Diode), also known as organic electroluminescent device, is a current-driven semiconductor light-emitting device based on organic materials. Unlike LCD, OLED is self-emissive, does not require a backlight, and has advantages such as flexibility, thinness, fast response speed, wide viewing angle, high contrast, and lifelike colors.

[0003] In an OLED, holes generated at the anode and electrons generated at the cathode move under the influence of an electric field and are injected into the hole transport layer and electron transport layer, respectively. When the two meet in the light-emitting layer, they interact to form excited excitons. When the excitons return from the excited state to the ground state, they radiate and generate an energy difference, which is eventually released in the form of photons.

[0004] OLED device structures have undergone continuous development, evolving from single-layer to double-layer, then to more complex triple-layer structures, and finally to the classic multi-layer structures. This continuous improvement in structure has led to a qualitative leap in luminescent performance. Organic light-emitting devices generally consist of an anode, a metal cathode, and an organic layer sandwiched between the two electrodes. This organic layer includes hole injection layers, hole transport layers, luminescent layers, electron transport layers, or electron injection layers. The luminescent layer provides a favorable environment for the combination of holes and electrons, facilitating efficient light emission and thus occupying a crucial position among the functional layers of an OLED.

[0005] Currently, with the continuous deepening of research on organic electroluminescent devices, the requirements for light-emitting host materials are gradually increasing, making the design and development of new and efficient host materials increasingly important. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides a fused cycloindo-carbazole compound and its organic electroluminescent device.

[0007] This invention provides a fused cyclopentadienylcarbazole compound, represented by the following Formula 1.

[0008]

[0009] The rings A, B, and C are independently selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C2-C30 heteroaromatic rings, and at least one of rings A, B, and C is a substituted or unsubstituted fused ring with more than 10 cyclic atoms.

[0010] X1 and X2 are independently selected from single bonds or N(Rx), and Rx and Ry are independently selected from... Or *-L-Ar2, and at least one of them is selected from

[0011] The Ar1 is selected from one or a combination of aryl groups with 10 to 30 cyclic atoms (substituted or unsubstituted) and heteroaryl groups with 10 to 30 cyclic atoms (substituted or unsubstituted).

[0012] The Ar is selected from one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic groups.

[0013] The r1 is selected from integers from 0 to 3; the R0, whether the same or different, is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring.

[0014] The Ar2 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted heteroaryl with 7-30 cyclic atoms, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings.

[0015] The L1, L2, and L3 are independently selected from one or a combination thereof, including single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C25 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene rings.

[0016] The L is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted heteroarylene with 10-30 cyclic atoms, a fused cycloalcoholic group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C30 aromatic ring, and a fused cycloalcoholic group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring.

[0017] The present invention also provides an organic electroluminescent device containing the fused cycloindo-carbazole compound of the present invention described above.

[0018] Beneficial effects: The fused cyclodopylindolocarbazole compound of Formula 1 of this invention has good stability and high triplet energy level, which can more effectively confine triplet excitons in the guest material and suppress the energy back-transfer process from the guest material to the host material. When used as the host material of the light-emitting layer in organic electroluminescent devices, it can effectively improve the performance of the device, specifically by reducing the driving voltage of the device, increasing the luminous efficiency of the device, and extending the service life of the device. Detailed Implementation

[0019] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0020] In this invention, "integers selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, "r1 is selected from 0 to 3" means that r1 is selected from 0, 1, 2, or 3. And so on.

[0021] In the compounds of this invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0022] The halogens described in this invention include fluorine, chlorine, bromine, and iodine.

[0023] In this invention, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0024] For example, Can represent Can represent Can represent And so on.

[0025] In this invention, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the bonding of adjacent groups can be connected to another ring to form a spirostructure. An example is shown below:

[0026]

[0027] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0028] In this invention, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C30 aryl group" means that the hydrogen atom of the "aryl group" is not substituted by a substituent. And so on.

[0029] In this invention, "CXX~CYY" in "substituted or unsubstituted CXX~CYY ZZ group" represents the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, it does not include the number of carbon atoms in the substituent. For example, "C6~C30" in "substituted or unsubstituted C6~C30 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, it does not include the number of carbon atoms in the substituent. And so on.

[0030] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" in the above-mentioned terms include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted C2-C15 heterocyclic group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C2-C20 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C20 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C20 heteroaryl ring, etc. Preferred groups include: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, fentanyl, silyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The substituents include benzo[a]yl, fluoranthyl, benzo[a]cyclopropane, benzo[a]cyclobutane, dihydroindyl, indyl, tetrahydronaphthyl, dihydronaphthyl, benzo[a]cycloheptyl, benzo[a]cyclobutenyl, fluorenyl, benzo[a]fluorenyl, spirodifluorenyl, benzo[a]spirodifluorenyl, benzo[a]furanyl, dibenzo[a]furanyl, benzo[a]dibenzo[a]furanyl, benzo[a]thiopheneyl, dibenzo[a]thiopheneyl, benzo[a]dibenzo[a]thiopheneyl, indolyl, carbazoleyl, benzo[a]carbazoleyl, benzo[a]dioxonyl, benzo[a]disulfideyl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzo[a]thiopheneyl, dihydroisobenzo[a]thiopheneyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can bond together to form substituted or unsubstituted rings.

[0031] The "fused ring with more than 10 cyclic atoms" described in this invention includes fused aromatic rings or fused heteroaromatic rings. These include, but are not limited to, naphthalene rings, phenanthrene rings, triphenylene rings, anthracene rings, quinoline rings, isoquinoline rings, quinazoline rings, quinoxaline rings, naphthalene rings, benzoquinoline rings, benzoisoquinoline rings, benzonaphthalene rings, phenanthrene rings, azaanthracene rings, and azatriphenylene rings.

[0032] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group includes straight-chain alkyl groups and branched-chain alkyl groups. The alkyl group has 1 to 20 carbon atoms, preferably 1 to 15, and even more preferably 1 to 10. The alkyl group includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, etc., but is not limited to these; and chain alkyl groups containing three or more carbon atoms include their isomers, such as propyl including n-propyl and isopropyl, butyl including n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on.

[0033] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silyl groups specifically include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc. The silane group mentioned above is preferably trimethylsilane, triethylsilane, triphenylsilane, diphenylmethylsilane, phenyldimethylsilane, diphenylmethylsilane, or phenyldimethylsilane.

[0034] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, and bridged cycloalkyl. The cycloalkyl group has 3 to 20 carbon atoms, preferably 3 to 15, and even more preferably 3 to 10. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, etc.

[0035] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. The number of carbon atoms in the aryl group is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12. The aryl group includes, but is not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene, perylene, fluorene, benzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, spiroanthracene fluorene, etc.

[0036] The heteroaryl group described in this invention refers to a group obtained by replacing one or more carbon atoms of an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, and silicon atoms. The heteroaryl group comprises monocyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. The heteroaryl group may have 2 to 30 carbon atoms, preferably 2 to 25, and more preferably 3 to 18. The heteroaryl groups include, but are not limited to, dibenzofuranyl, benzodibenzofuranyl, furanyl, benzofuranyl, naphthofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, thiophenyl, benzothiophenyl, naphthothiophenyl, carbazoyl, benzocarbazoyl, indolyl, spirofluorenexanthracene, spirofluorenethionanthracene, spirofluorenesilanthracene, benzodioxonyl, benzodisulfide, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, benzodioxinyl, dihydroacridyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, etc.

[0037] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. The alicyclic ring has 3 to 25 carbon atoms, preferably 3 to 20, more preferably 3 to 15, and even more preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 18, more preferably 6 to 12, and even more preferably 6 to 10. The fused alicyclic and aromatic ring groups include, but are not limited to, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, and benzocycloheptenyl.

[0038] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. The alicyclic ring has 3 to 20 carbon atoms, preferably 3 to 15, and even more preferably 3 to 10. The heteroaromatic ring has 2 to 30 carbon atoms, preferably 2 to 25, more preferably 2 to 18, and even more preferably 2 to 10. The fused cyclic group of alicyclic and aromatic rings includes, but is not limited to, pyridocyclopentyl, pyridocyclohexyl, pyridocyclobutyl, and pyridocyclopentenyl.

[0039] The arylene group referred to in this invention refers to the collective term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. The number of carbon atoms in the arylene group is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 10. The arylene group includes, but is not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, fluorene, benzo[a]fluorene, spirodifluorene, and benzo[a]spirodifluorene.

[0040] The heteroaryl group refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc., but is not limited thereto. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. The number of carbon atoms in the heteroaryl group is 2 to 30, preferably 2 to 25, more preferably 2 to 18, and even more preferably 2 to 10. The heteroaryl group includes, but is not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indoleyl, carbazoyl, etc.

[0041] The fused alicyclic and aromatic rings described in this invention refer to the collective term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. The alicyclic ring has 3 to 20 carbon atoms, preferably 3 to 15, and even more preferably 3 to 8. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 10. The fused alicyclic and aromatic rings include, but are not limited to, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cycloheptane, benzo[a]cyclobutenyl, and naphtho[a]cyclopentane.

[0042] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the collective term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and heteroaromatic rings. The alicyclic ring has 3 to 20 carbon atoms, more preferably 3 to 15, and even more preferably 3 to 8. The heteroaromatic ring has 2 to 30 carbon atoms, more preferably 2 to 25, more preferably 2 to 18, and even more preferably 2 to 10. The fused alicyclic and heteroaromatic ring groups include, but are not limited to, pyridinocyclopentyl, pyridinocyclohexyl, pyridinocyclopropyl, pyridinocyclobutyl, and pyridinocyclopentenyl groups.

[0043] This invention provides a fused cyclopentadienylcarbazole compound, represented by the following Formula 1.

[0044]

[0045] The rings A, B, and C are independently selected from one of substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C2-C30 heteroaromatic rings, and at least one of rings A, B, and C is a substituted or unsubstituted fused ring with more than 10 cyclic atoms.

[0046] X1 and X2 are independently selected from single bonds or N(Rx), and Rx and Ry are independently selected from... Or *-L-Ar2, and at least one of them is selected from

[0047] The Ar1 is selected from one or a combination of aryl groups with 10 to 30 cyclic atoms (substituted or unsubstituted) and heteroaryl groups with 10 to 30 cyclic atoms (substituted or unsubstituted).

[0048] The Ar is selected from one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic groups.

[0049] The r1 is selected from integers from 0 to 3; the R0, whether the same or different, is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring.

[0050] The Ar2 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted heteroaryl with 7-30 cyclic atoms, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings.

[0051] The L1, L2, and L3 are independently selected from one or a combination thereof, including single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C25 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene rings.

[0052] The L is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted heteroarylene with 10-30 cyclic atoms, a fused cycloalcoholic group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C30 aromatic ring, and a fused cycloalcoholic group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring.

[0053] Preferably, X1 is selected from a single bond and X2 is selected from N(Rx); or X1 is selected from N(Rx) and X2 is selected from a single bond.

[0054] Preferably, the fused cyclopentadienylcarbazole compound is selected from at least one of Formulas 1-1 and 1-2.

[0055]

[0056] Preferably, the Ar1 is selected from one or a combination of the following groups:

[0057]

[0058] The n1 is selected from integers from 0 to 7, the n2 is selected from integers from 0 to 9, the n3 is selected from integers from 0 to 3, the n4 is selected from integers from 0 to 4, and the n5 is selected from integers from 0 to 5.

[0059] The Rs, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or adjacent Rs bonded together to form a substituted or unsubstituted ring;

[0060] The W1 and W2 are independently selected from single bonds, O, S, N(Rw), C(Rw)2, and Si(Rw)2. The Rws, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings, or combinations thereof. Alternatively, two adjacent Rws may be bonded to each other to form a substituted or unsubstituted ring, or Rw may be a single bond directly bonded to L3.

[0061] The X that is the same or different is selected from CH or N.

[0062] Preferably, the Ar1 is selected from one or a combination of the following groups:

[0063]

[0064] The n1 is selected from integers from 0 to 7, the n2 is selected from integers from 0 to 9, the n3 is selected from integers from 0 to 3, the n4 is selected from integers from 0 to 4, the n5 is selected from integers from 0 to 5, and the n6 is selected from integers from 0 to 6.

[0065] The Rs, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl ring, or adjacent Rs bonded together to form a substituted or unsubstituted ring.

[0066] The W1, W2, and W3 are independently selected from O, S, N(Rw), C(Rw)2, and Si(Rw)2. The Rws, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl rings, or combinations thereof. Alternatively, two adjacent Rws may be bonded to each other to form a substituted or unsubstituted ring, or Rw may be a single bond directly bonded to L3.

[0067] Preferably, the Ar1 is selected from one or a combination of the following groups:

[0068]

[0069]

[0070] The n1 is selected from integers from 0 to 7, the n2 is selected from integers from 0 to 9, the n3 is selected from integers from 0 to 3, the n4 is selected from integers from 0 to 4, the n5 is selected from integers from 0 to 5, and the n6 is selected from integers from 0 to 6.

[0071] The Rs, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl ring, or adjacent Rs bonded together to form a substituted or unsubstituted ring;

[0072] The Rws, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent Rws bonded together to form a substituted or unsubstituted ring, or Rws can be single bonds directly bonded to L3.

[0073] Preferably, the same or different R is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl] The substituted or unsubstituted benzothiophene group, the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophene group, the substituted or unsubstituted carbazolyl group, the substituted or unsubstituted indolyl group, the substituted or unsubstituted dihydroindene group, the substituted or unsubstituted indene group, the substituted or unsubstituted tetrahydronaphthyl group, the substituted or unsubstituted dihydronaphthyl group, the substituted or unsubstituted benzocyclopropane group, the substituted or unsubstituted benzocyclobutane group, the substituted or unsubstituted benzocyclobutenyl group, the substituted or unsubstituted benzocycloheptane group, the substituted or unsubstituted benzocycloheptenyl group, the substituted or unsubstituted pyridinyl group, the substituted or unsubstituted pyrazinyl group, the substituted or unsubstituted pyridazinyl group, the substituted or unsubstituted triazinyl group, the substituted or unsubstituted quinolinyl group, the substituted or unsubstituted isoquinolinyl group, or any two adjacent R groups bonded together to form a substituted or unsubstituted ring;

[0074] The Rw, whether the same as or different from Rw, is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl], substituted or unsubstituted benzo[thiophene] The Rw may be one of the following: substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, or substituted or unsubstituted isoquinolinyl; or two adjacent Rw may be bonded to each other to form a substituted or unsubstituted ring; or Rw may be a single bond directly bonded to L3.

[0075] Preferably, the Ar is selected from one or a combination of the following groups:

[0076]

[0077] m1 is selected from integers from 0 to 7, m2 is selected from integers from 0 to 9, m3 is selected from integers from 0 to 3, m4 is selected from integers from 0 to 4, m5 is selected from integers from 0 to 5, and m6 is selected from integers from 0 to 2.

[0078] The R1s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings, or adjacent R1s bonded together to form substituted or unsubstituted rings.

[0079] The G1 and G2 are independently selected from single bonds, O, S, N(Rg), C(Rg)2, and Si(Rg)2. The Rgs, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings, or combinations thereof. Alternatively, two adjacent Rgs may be bonded to each other to form a substituted or unsubstituted ring, or Rg may be a single bond directly bonded to L2.

[0080] M is selected from O, S, N (Rm), and Rm, whether the same or different, is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or Rm can be a single bond directly bonded to L2;

[0081] The same or different Y is selected from CH or N.

[0082] Preferably, the Ar is selected from one or a combination of the following groups:

[0083]

[0084] The m1 is selected from integers from 0 to 7, the m2 is selected from integers from 0 to 9, the m3 is selected from integers from 0 to 3, the m4 is selected from integers from 0 to 4, the m5 is selected from integers from 0 to 5, the m6 is selected from integers from 0 to 2, and the m7 is selected from integers from 0 to 6.

[0085] The R1s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl rings, or adjacent R1s bonded together to form substituted or unsubstituted rings.

[0086] The G1 and G2 are independently selected from O, S, N(Rg), C(Rg)2, and Si(Rg)2. The Rgs, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl ring, or combinations thereof. Alternatively, two adjacent Rgs may be bonded to each other to form a substituted or unsubstituted ring, or Rg may be a single bond directly bonded to L2.

[0087] M is selected from O, S, N (Rm), and Rm is selected from one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C25 aryl group, substituted or unsubstituted C2-C25 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl ring, or Rm can be a single bond directly bonded to L2.

[0088] Preferably, the Ar is selected from one or a combination of the following groups:

[0089]

[0090]

[0091] The m1 is selected from integers from 0 to 7, the m2 is selected from integers from 0 to 9, the m3 is selected from integers from 0 to 3, the m4 is selected from integers from 0 to 4, the m5 is selected from integers from 0 to 5, the m6 is selected from integers from 0 to 2, the m7 is selected from integers from 0 to 6, the m8 is selected from integers from 0 to 8, and the m9 is selected from integers from 0 to 10.

[0092] The R1s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent R1s bonded together to form substituted or unsubstituted rings.

[0093] The R5s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent R5s bonded together to form substituted or unsubstituted rings.

[0094] The Rg is the same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl ring, or adjacent Rg are bonded to each other to form a substituted or unsubstituted ring, or Rg can be a single bond directly bonded to L2;

[0095] The Rm may be the same as or different from one or a combination thereof, selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C20 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl groups, or Rm may be a single bond directly bonded to L2.

[0096] Preferably, R1 is the same or different from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R1s bonded together to form a substituted or unsubstituted ring;

[0097] The R5s, whether identical or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, or two adjacent R5s bonded together to form a substituted or unsubstituted ring;

[0098] The Rg is the same as or different from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl], substituted or unsubstituted benzo[thiazolyl] One of the following: phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent Rgs bonded to each other to form a substituted or unsubstituted ring, or Rg can be a single bond directly bonded to L2;

[0099] The Rm is the same as or different from that selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl], substituted or One of the following: unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or Rm can be a single bond directly bonded to L2.

[0100] Preferably, the Ar2 is selected from one or a combination of the following groups:

[0101]

[0102] The integer t1 is selected from 0 to 7, the integer t2 is selected from 0 to 9, the integer t3 is selected from 0 to 3, the integer t4 is selected from 0 to 4, the integer t5 is selected from 0 to 5, the integer t6 is selected from 0 to 2, and the integer t7 is selected from 0 to 6.

[0103] The R6s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl rings, or adjacent R6s bonded together to form substituted or unsubstituted rings.

[0104] The Q1 and Q2 are independently selected from O, S, N(Rq), C(Rq)2, and Si(Rq)2. The Rq, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl ring, or a combination thereof. Alternatively, two adjacent Rq may be bonded to each other to form a substituted or unsubstituted ring, or Rq may be a single bond directly bonded to L.

[0105] M1 is selected from N or C(R6).

[0106] M2 is selected from O, S, N(R) m2 ), the R m2 Selected from one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C25 aryl groups, substituted or unsubstituted C2-C25 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl rings, or R m2 It can be a single bond that is directly bonded to L;

[0107] The F that is the same or different is selected from CH or N.

[0108] Preferably, each group has at most three Fs selected from N, or at most two Fs selected from N, or at most one F selected from N.

[0109] Preferably, the Ar2 is selected from one or a combination of the following groups:

[0110]

[0111]

[0112] The integer t1 is selected from 0 to 7, the integer t2 is selected from 0 to 9, the integer t3 is selected from 0 to 3, the integer t4 is selected from 0 to 4, the integer t5 is selected from 0 to 5, the integer t6 is selected from 0 to 2, the integer t7 is selected from 0 to 6, the integer t8 is selected from 0 to 8, and the integer t9 is selected from 0 to 10.

[0113] The R6s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent R6s bonded together to form substituted or unsubstituted rings.

[0114] The R7s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent R7s bonded together to form substituted or unsubstituted rings.

[0115] The Rqs, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or adjacent Rqs may be bonded to each other to form a substituted or unsubstituted ring, or Rq may be a single bond directly bonded to L.

[0116] The R m2 Selected from one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C20 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C10 alicyclic and C2-C20 heteroaryl rings, or R m2 It can be a single bond that is directly bonded to L.

[0117] Preferably, the same or different R6 is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R6 groups bonded together to form a substituted or unsubstituted ring;

[0118] The R7s, whether identical or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or adjacent R7s bonded together to form a substituted or unsubstituted ring;

[0119] The Rq is the same as or different from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl], substituted or unsubstituted benzo[thiazolyl] One of the following: phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent Rq are bonded to each other to form a substituted or unsubstituted ring, or Rq can be a single bond directly bonded to L;

[0120] The R m2Selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[a]fluorenyl Furanyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or R m2 It can be a single bond that is directly bonded to L.

[0121] Preferably, L1, L2, and L3 are independently selected from single bonds or one or a combination of the groups shown below.

[0122]

[0123] The J is selected from O, S, C(R) j )2、N(R j ), the R j Selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or two adjacent R j They bond with each other to form substituted or unsubstituted rings;

[0124] The V is selected from O, S, C(R) v )2、N(Rv ), the R v Selected from one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings, or two adjacent R groups. v They bond with each other to form substituted or unsubstituted rings;

[0125] The e1 is selected from an integer from 0 to 4; the e2 is selected from an integer from 0 to 2; the R3 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or two adjacent R3s are bonded to each other to form a substituted or unsubstituted ring;

[0126] The same or different E is selected from CH or N.

[0127] Preferably, L1, L2, and L3 are independently selected from single bonds or one or a combination of the groups shown below.

[0128]

[0129]

[0130] The number e1 is selected from integers from 0 to 4, the number e2 is selected from integers from 0 to 2, the number e3 is selected from integers from 0 to 3, the number e4 is selected from integers from 0 to 6, and the number e5 is selected from integers from 0 to 8.

[0131] The Rj is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or two adjacent Rj. j They bond with each other to form substituted or unsubstituted rings;

[0132] The Rv is selected from one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring.

[0133] The R3 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or adjacent R3s bonded to each other to form a substituted or unsubstituted ring;

[0134] The R8 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or adjacent R8s bonded to each other to form a substituted or unsubstituted ring.

[0135] Preferably, the same or different Rj is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent Rj bonded to each other to form a substituted or unsubstituted ring;

[0136] The Rv, whether the same or different, is selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted... Or one of the following: benzofuranyl or unsubstituted, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl;

[0137] The R3 is the same as or different from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[a]fluorenyl One of the following: furanyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R3s bonded together to form a substituted or unsubstituted ring;

[0138] The R8 group, whether identical or different, is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[a]fluorenyl One of the following: furanyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R8 groups bonded together to form a substituted or unsubstituted ring.

[0139] Preferably, L is selected from a single bond or one of the following groups:

[0140]

[0141] The b1 is selected from integers from 0 to 4; the R9 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or two adjacent R9s are bonded to each other to form a substituted or unsubstituted ring;

[0142] The same or different B is selected from CH or N; the same or different A is selected from CH or N, and the ring must contain N, and the number of nitrogen atoms is 1 or 2.

[0143] Preferably, L is selected from a single bond or one of the following groups:

[0144]

[0145] b1 is selected from integers from 0 to 4, b2 is selected from integers from 0 to 2, b3 is selected from integers from 0 to 3, b4 is selected from integers from 0 to 6, and b5 is selected from integers from 0 to 8;

[0146] The R9 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or adjacent R9s bonded to each other to form a substituted or unsubstituted ring;

[0147] The R 10 Selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or two adjacent R 10 They bond with each other to form substituted or unsubstituted rings.

[0148] Preferably, the same or different R9s are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R9s bonded together to form a substituted or unsubstituted ring;

[0149] The R 10The same or different from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or One of the following: unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted indolyl, substituted or unsubstituted dihydroindeneyl, substituted or unsubstituted indeneyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropaneyl, substituted or unsubstituted benzocyclobutaneyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptaneyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R 10 They bond with each other to form substituted or unsubstituted rings.

[0150] Preferably, ring A and ring C are independently selected from one of the following groups:

[0151]

[0152]

[0153] The ring B is selected from one of the following groups.

[0154]

[0155] *, ·, and + indicate confluence sites;

[0156] f1 is selected from integers from 0 to 4, f2 is selected from integers from 0 to 6, f3 is selected from integers from 0 to 8, and f4 is selected from integers from 0 to 2.

[0157] The R4 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or adjacent R4s bonded to each other to form a substituted or unsubstituted ring;

[0158] The T values ​​that are the same or different are selected from CH or N;

[0159] Furthermore, at least one of ring A, ring B, and ring C is a fused ring with 10 to 18 cyclic atoms.

[0160] Preferably, each ring A, ring B, and ring C contains at most three N atoms, at most two N atoms, or at most one N atom. Preferably, ring A and ring C are independently selected from one of the following groups:

[0161]

[0162]

[0163] The ring B is selected from one of the following groups.

[0164]

[0165]

[0166]

[0167]

[0168] f1 is selected from integers from 0 to 4, f2 is selected from integers from 0 to 6, f3 is selected from integers from 0 to 8, f4 is selected from integers from 0 to 2; f5 is selected from integers from 0 to 3; f6 is selected from integers from 0 to 5; f7 is selected from integers from 0 to 7.

[0169] The R4 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C25 heteroaryl ring, or adjacent R4s bonded to each other to form a substituted or unsubstituted ring;

[0170] Furthermore, at least one of ring A, ring B, and ring C is a fused ring with 10 to 18 cyclic atoms.

[0171] Preferably, the same or different R4s are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzo[fluorenyl], substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzo[furanyl] The substituted or unsubstituted benzothiophene group, the substituted or unsubstituted dibenzofuran group, the substituted or unsubstituted dibenzothiophene group, the substituted or unsubstituted carbazolyl group, the substituted or unsubstituted indolyl group, the substituted or unsubstituted dihydroindene group, the substituted or unsubstituted indene group, the substituted or unsubstituted tetrahydronaphthyl group, the substituted or unsubstituted dihydronaphthyl group, the substituted or unsubstituted benzocyclopropane group, the substituted or unsubstituted benzocyclobutane group, the substituted or unsubstituted benzocyclobutenyl group, the substituted or unsubstituted benzocycloheptane group, the substituted or unsubstituted benzocycloheptenyl group, the substituted or unsubstituted pyridinyl group, the substituted or unsubstituted pyrazinyl group, the substituted or unsubstituted pyridazinyl group, the substituted or unsubstituted triazinyl group, the substituted or unsubstituted quinolinyl group, the substituted or unsubstituted isoquinolinyl group, or any two adjacent R4 groups bonded together to form a substituted or unsubstituted ring.

[0172] Preferably, the group In this context, R0, whether the same or different, is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted silyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or One of the following: unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, or substituted or unsubstituted pyridazinyl, or two adjacent R0s bonded together to form a substituted or unsubstituted ring.

[0173] Preferably, the group Selected from one of the following groups,

[0174]

[0175] Preferably, the fused cyclopentadienocarbazole compound is selected from at least one of the following structures:

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] The above lists some specific chemical structures of the fused cycloindo-carbazole compounds represented by Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents as defined above should be included.

[0200] In addition, the present invention provides an organic electroluminescent device containing the fused cycloindo-carbazole compound of the present invention described above.

[0201] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer containing the fused cycloindocarbazole compound of the present invention described above.

[0202] Preferably, the organic layer includes a light-emitting layer containing the fused cycloindolinecarbazole compound of the present invention described above.

[0203] Preferably, the light-emitting layer contains a host material, which contains the fused cycloindo-carbazole compound of the present invention described above.

[0204] Preferably, the organic electroluminescent device includes an anode, a cathode, an organic layer located between the anode and the cathode, and a capping layer located outside the anode or cathode, wherein the capping layer contains the fused cycloindocarbazole compound of the present invention described above.

[0205] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, capping layer, etc. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, or light extraction properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0206] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0207] The anode of this invention generally uses a material with a high work function. The anode includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), platinum (Pt), indium tin oxide (ITO), indium zinc oxide (IZO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited to these.

[0208] The cathode of this invention generally uses a material with a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include aluminum (Al), calcium (Ca), indium (In), silver (Ag), magnesium (Mg), magnesium:silver (Mg:Ag), lithium:aluminum (Li:Al), etc., but are not limited to these.

[0209] The hole injection layer of the present invention is preferably made of a material having good hole injection capability and suitable HOMO energy level. The hole injection layer includes, but is not limited to, the materials described below, such as phthalocyanine metal complexes, aromatic amine derivatives, polycyano conjugated organic compounds, metal oxides, polymers, etc. Specific examples may include, but are not limited to, titanium phthalocyanine (TiOPC), platinum phthalocyanine (PtPC), N3,N3'-bis[4'-(diphenylamino)[1,1'-biphenyl]-4-yl]-N3,N3'-diphenyl-biphenyl-3,3'-diamine (TPT1), 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), vanadium pentoxide (V2O5), poly(4-vinyltriphenylamine) (PVTPA), etc.

[0210] The hole transport layer of the present invention is preferably made of a material with good stability and high hole mobility. The hole transport layer includes, but is not limited to, the materials described below, such as aromatic amine derivatives, carbazole derivatives, and polymers. Specific examples may include, but are not limited to, N4,N4-bis(1,1'-biphenyl)-4-yl-N4'-naphth-1-yl-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine, tetraphenylbenzidine diamine (BPBPA), N4,N4'-bis-1-naphthyl-N4,N4'-bis-2-naphthyl-[1,1'-biphenyl]-4,4'-diamine (α,β-TNB), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-(diphenylmethylene)bis(N,N-diphenylaniline) (TCBPA), 9,1-dihydro-9,9-dimethyl-1-(9-phenyl-9H-carbazole-3-yl)-pyridine (PCZAC), and polyvinylcarbazole (PVC).

[0211] The light-emitting layer of the present invention comprises a host material and a dopant material. The light-emitting material may be a red light-emitting material, a green light-emitting material, a blue light-emitting material, or a combination thereof. The doping ratio of the host material and the dopant material may vary depending on the material used. Typically, the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0212] The host material of the luminescent layer not only needs to possess bipolar charge transport properties, but also requires appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material can be one material or two or more materials. Host materials include, but are not limited to, the following: heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 2-(3-(naphtho[2,3-b]benzofuran-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 2,7-bis(9H-carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 9-(4-tert-butylphenyl)-3,6-ditriphenylmethyl-9H-carbazole (CzC), 9... Examples of compounds include, but are not limited to, 9'-bis(4-triphenylmethylphenyl)-9H,9'H-3,3'-bicarbazole (BCzTPM), 3,3'-bis(dibenzothiophene-4-yl)-1,1'-biphenyl (m-BPDBT), 2,6-bis(3-(9H-carbazole-9-yl)phenyl)pyridine (26DCzPPy), 1,4-bis(9-phenyl-9H-fluorene-9-yl)phenyl (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), and bis[3,5-bis(9H-carbazole-9-yl)phenyl]diphenylsilane (SimCP2). Fused cyclobenzoindocarbazole compounds of Formula 1 of the present invention are preferred. The fused cyclodopylindolocarbazole compound of Formula 1 of the present invention can be used alone as a host material or in combination with a p-type host material or an n-type host material. When used in combination with a p-type host material or an n-type host material, the weight ratio of the fused cyclodopylindolocarbazole compound of Formula 1 of the present invention to the p-type host material or the n-type host material is 1:99 to 99:1, preferably 20:80 to 80:20.

[0213] The doped material can be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. Doped materials include, but are not limited to, the following: metal complexes, aromatic amine derivatives, styrene amine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include tris[2-(2,4-difluorophenyl)pyridine]iridium (Ir(Fppy)3), bis[2-(5-cyano-4,6-difluorophenyl)pyridine-C2,N)]pyridinecarboxylated iridium (FCNIrPic), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium acetylacetone (Ir(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetone)iridium (Ir(bzq)2(acac)), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptane-3,5-diionic acid)iridium (Ir(dpm)PQ2), and bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir) (piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), 2,5,8,11-tetra-tert-butylperylene (TBPe), 9,10-bis[N,N-di(p-tolyl)amino]anthracene (TTPA), 9,10-bis[N-(m-tolyl)phenylamino]anthracene (TPA), 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidin-9-enyl)-4H-pyran (DCJTB), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), etc., but not limited to these.

[0214] The hole-blocking layer of the present invention is preferably made of a material with good electron transport performance and good hole-blocking performance. The hole-blocking layer includes, but is not limited to, the materials described below: phenanthroline derivatives, metal complexes, triazole derivatives, triazine derivatives, imidazole derivatives, etc. Specific examples may include 2,9-dimethyl-4,7-biphenyl-1,10-o-diazaphenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), etc., but is not limited thereto.

[0215] The electron transport layer of the present invention is preferably made of a material with good stability and high electron mobility. The electron transport layer includes, but is not limited to, the materials described below, such as metal complexes and heteroaromatic compounds. Specific examples may include, but are not limited to, 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline) beryllium (Bepq2), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (TmPyPB), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridylquinoline-2-yl)benzene (TPyQB), 2,7-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]-9,9-dimethylfluorene (Bpy-FOXD), etc.

[0216] The electron injection material of this invention needs to possess properties such as good hole injection capability and suitable energy levels to reduce the interfacial barrier between the cathode and the electron transport layer and improve electron injection capability. The electron injection layer material includes, but is not limited to, the materials described below, such as metals, metal compounds, and metal oxides. Specific examples may include lithium (Li), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), cesium fluoride (CsF), cesium carbonate (Cs₂CO₃), and aluminum oxide (Al₂O₃), but are not limited to these.

[0217] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0218] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0219] Synthesis Examples

[0220] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0221] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0222] There are no particular limitations on the preparation method of the fused cyclobenzoindocarbazole compound shown in Formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. Taking Formulas 1-1 and 1-2 as examples, the fused cyclobenzoindocarbazole compound shown in Formula 1 of the present invention can be prepared, for example, by the synthetic route shown below.

[0223]

[0224] The Xn is a halogen, for example, the same or different Xn are selected from Cl, Br, I.

[0225] Synthesis example 1:

[0226]

[0227] Preparation of A-2:

[0228] Under nitrogen protection, a-2 (9.46 g, 35.00 mmol), b-2 (12.04 g, 70.00 mmol), K3PO4 (29.72 g, 140 mmol), Pd(OAc)2 (314 mg, 1.40 mmol), XPhos (1.33 g, 2.80 mmol), toluene (400 mL), and water (20 mL) were added to a reaction flask, and the mixture was reacted under reflux for 15 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 phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to obtain A-2 (10.09 g, 79%). The purity of the solid was determined by HPLC to be ≥99.78%.

[0229] Preparation of compound 2:

[0230] Under nitrogen protection, B-2 (7.65 g, 20.00 mmol), A-2 (8.76 g, 24.00 mmol), copper powder (1.65 g, 26.00 mmol), 18-crown ether-6 (529 mg, 2.00 mmol), K2CO3 (3.32 g, 24.00 mmol), and DMF (100 ml) were added to a reaction flask and stirred under reflux for 20 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 2 (10.52 g, 74%). HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrometry m / z: 710.2743 (theoretical value: 710.2722). Theoretical elemental content (%) C 54 H 34N2: C, 91.24; H, 4.82; N, 3.94. Measured elemental content (%): C, 91.28; H, 4.80; N, 3.91.

[0231] Synthesis example 2:

[0232]

[0233] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-34, and B-2 was replaced with an equimolar amount of B-34 to obtain compound 34 (10.95 g); HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 710.2738 (theoretical value: 710.2722). Theoretical elemental content (%) C 54 H 34 N2: C, 91.24; H, 4.82; N, 3.94. Measured elemental content (%): C, 91.27; H, 4.84; N, 3.91.

[0234] Synthesis example 3:

[0235]

[0236] Following the preparation method of compound 2 in Synthesis Example 1, a-2 was replaced with an equimolar amount of a-39, and B-2 was replaced with an equimolar amount of B-39, yielding compound 39 (10.81 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 760.2889 (theoretical value: 760.2878). Theoretical elemental content (%) C 58 H 36 N2: C, 91.55; H, 4.77; N, 3.68. Measured elemental content (%): C, 91.59; H, 4.74; N, 3.65.

[0237] Synthesis example 4:

[0238]

[0239] Preparation of A1-67:

[0240] Under nitrogen protection, a-67 (19.04 g, 60.00 mmol), b1-67 (14.88 g, 60.00 mmol), K2CO3 (12.44 g, 90 mmol), Pd(PPh3)4 (693 mg, 0.60 mmol), toluene (250 ml), ethanol (50 ml), and water (50 ml) were added to a reaction flask, and the mixture was reacted under reflux for 8 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 phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (petroleum ether: dichloromethane = 6:1) to obtain Al-67 (16.06 g, 68%). The purity of the solid was determined by HPLC to be ≥99.67%.

[0241] Preparation of A-67:

[0242] Under nitrogen protection, A1-67 (13.78 g, 35.00 mmol), b2-67 (4.27 g, 35.00 mmol), K3PO4 (14.86 g, 70 mmol), Pd(OAc)2 (157 mg, 0.70 mmol), XPhos (667 mg, 1.40 mmol), toluene (200 mL), and water (10 mL) were added to a reaction flask, and the mixture was reacted under reflux for 12 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 phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The solid was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to obtain A-67 (10.81 g, 79%), with a solid purity of ≥99.78% as determined by HPLC.

[0243] Preparation of compound 67:

[0244] Following the preparation method of compound 2 in Synthesis Example 1, A-2 was replaced with an equimolar amount of A-67, and B-2 was replaced with an equimolar amount of B-67, yielding compound 67 (10.61 g, 72%); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 736.2889 (theoretical value: 736.2878). Theoretical elemental content (%) C 56 H 36 N2: C, 91.27; H, 4.92; N, 3.80. Measured elemental content (%): C, 91.24; H, 4.94; N, 3.83.

[0245] Synthesis example 5:

[0246]

[0247] Following the preparation method of compound 2 in Synthesis Example 1, B-2 was replaced with an equimolar amount of B-77 to obtain compound 77 (11.33 g); HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 786.3047 (theoretical value: 786.3035). Theoretical elemental content (%) C 60 H 38 N2: C, 91.57; H, 4.87; N, 3.56. Measured elemental content (%): C, 91.53; H, 4.85; N, 3.59.

[0248] Synthesis example 6:

[0249]

[0250] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-85, and B-67 was replaced with an equimolar amount of B-85, yielding compound 85 (10.76 g); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 736.2886 (theoretical value: 736.2878). Theoretical elemental content (%) C 56 H 36 N2: C, 91.27; H, 4.92; N, 3.80. Measured elemental content (%): C, 91.29; H, 4.89; N, 3.83.

[0251] Synthesis example 7:

[0252]

[0253] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-98, and B-2 was replaced with an equimolar amount of B-98, yielding compound 98 (12.00 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 810.3044 (theoretical value: 810.3035). Theoretical elemental content (%) C 62 H 38 N2: C, 91.82; H, 4.72; N, 3.45. Measured elemental content (%): C, 91.80; H, 4.75; N, 3.43.

[0254] Synthesis example 8:

[0255]

[0256] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-101, and B-67 was replaced with an equimolar amount of B-34 to obtain compound 101 (11.80 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 786.3046 (theoretical value: 786.3035). Theoretical elemental content (%) C 60 H 38 N2: C, 91.57; H, 4.87; N, 3.56. Measured elemental content (%): C, 91.59; H, 4.89; N, 3.53.

[0257] Synthesis example 9:

[0258]

[0259] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-98, and B-2 was replaced with an equimolar amount of B-34, yielding compound 111 (12.33 g); HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 810.3048 (theoretical value: 810.3035). Theoretical elemental content (%) C 62 H 38 N2: C, 91.82; H, 4.72; N, 3.45. Measured elemental content (%): C, 91.85; H, 4.70; N, 3.43.

[0260] Synthesis example 10:

[0261]

[0262] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-159, and B-67 was replaced with an equimolar amount of B-159, yielding compound 159 (12.09 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 816.3515 (theoretical value: 816.3504). Theoretical elemental content (%) C 62 H 44 N2: C, 91.14; H, 5.43; N, 3.43. Measured elemental content (%): C, 91.16; H, 5.40; N, 3.46.

[0263] Synthesis example 11:

[0264]

[0265] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-206, and B-67 was replaced with an equimolar amount of B-206, yielding compound 206 (11.68 g); HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 810.3047 (theoretical value: 810.3035). Theoretical elemental content (%) C 62 H 38 N2: C, 91.82; H, 4.72; N, 3.45. Measured elemental content (%): C, 91.84; H, 4.76; N, 3.40.

[0266] Synthesis example 12:

[0267]

[0268] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-215, b2-67 with an equimolar amount of b2-215, and B-67 with an equimolar amount of B-85, yielding compound 215 (10.74 g); HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 766.3357 (theoretical value: 766.3348). Theoretical elemental content (%) C 58 H 42 N2: C, 90.83; H, 5.52; N, 3.65. Measured elemental content (%): C, 90.80; H, 5.55; N, 3.62.

[0269] Synthesis example 13:

[0270]

[0271] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-219, and B-67 was replaced with an equimolar amount of B-219 to obtain compound 219 (11.19 g); HPLC analysis showed that the solid purity was ≥99.89%. Mass spectrometry m / z: 776.3199 (theoretical value: 776.3191). Theoretical elemental content (%) C 59 H 40 N2: C, 91.21; H, 5.19; N, 3.61. Measured elemental content (%): C, 91.24; H, 5.17; N, 3.57.

[0272] Synthesis example 14:

[0273]

[0274] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-227, and B-67 was replaced with an equimolar amount of B-34 to obtain compound 227 (11.05 g); HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 726.3049 (theoretical value: 726.3035). Theoretical elemental content (%) C 55 H 38 N2: C, 90.88; H, 5.27; N, 3.85. Measured elemental content (%): C, 90.86; H, 5.29; N, 3.83.

[0275] Synthesis example 15:

[0276]

[0277] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-250, and B-67 was replaced with an equimolar amount of B-34, yielding compound 250 (12.60 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 850.3361 (theoretical value: 850.3348). Theoretical elemental content (%) C 65 H 42 N2: C, 91.73; H, 4.97; N, 3.29. Measured elemental content (%): C, 91.76; H, 4.99; N, 3.25.

[0278] Synthesis example 16:

[0279]

[0280] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-268, and B-2 was replaced with an equimolar amount of B-34, yielding compound 268 (12.98 g); HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 842.3673 (theoretical value: 842.3661). Theoretical elemental content (%) C 64 H 46 N2: C, 91.18; H, 5.50; N, 3.32. Measured element content (%): C, 91.15; H, 5.52; N, 3.34.

[0281] Synthesis example 17:

[0282]

[0283] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-310, and B-67 was replaced with an equimolar amount of B-310, yielding compound 310 (11.96 g); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 818.3677 (theoretical value: 818.3661). Theoretical elemental content (%) C 62 H 46 N2: C, 90.92; H, 5.66; N, 3.42. Measured elemental content (%): C, 90.96; H, 5.63; N, 3.40.

[0284] Synthesis example 18:

[0285]

[0286] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-311, and B-67 was replaced with an equimolar amount of B-311, yielding compound 311 (11.91 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 850.3359 (theoretical value: 850.3348). Theoretical elemental content (%) C 65 H 42 N2: C, 91.73; H, 4.97; N, 3.29. Measured elemental content (%): C, 91.76; H, 4.95; N, 3.26.

[0287] Synthesis example 19:

[0288]

[0289] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b-268, b2-67 with an equimolar amount of b-34, and B-67 with an equimolar amount of B-316, yielding compound 316 (10.72 g); HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 776.3202 (theoretical value: 776.3191). Theoretical elemental content (%) C 59 H 40 N2: C, 91.21; H, 5.19; N, 3.61. Measured elemental content (%): C, 91.25; H, 5.16; N, 3.63.

[0290] Synthesis example 20:

[0291]

[0292] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-319, and B-67 was replaced with an equimolar amount of B-85, yielding compound 319 (10.69 g); HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 752.3178 (theoretical value: 752.3191). Theoretical elemental content (%) C 57 H 40 N2: C, 90.92; H, 5.35; N, 3.72. Measured elemental content (%): C, 90.94; H, 5.32; N, 3.76.

[0293] Synthesis example 21:

[0294]

[0295] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-322, and B-67 was replaced with an equimolar amount of B-322, yielding compound 322 (11.91 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 826.2995 (theoretical value: 826.2984). Theoretical elemental content (%) C 62 H 38 N₂O: C, 90.05; H, 4.63; N, 3.39. Measured elemental content (%): C, 90.08; H, 4.61; N, 3.37.

[0296] Synthesis example 22:

[0297]

[0298] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b2-339, and B-67 with an equimolar amount of B-339, yielding compound 339 (11.34 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 776.2841 (theoretical value: 776.2828). Theoretical elemental content (%) C 58 H 36 N₂O: C, 89.66; H, 4.67; N, 3.61. Measured elemental content (%): C, 89.68; H, 4.63; N, 3.64.

[0299] Synthesis example 23:

[0300]

[0301] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, and B-67 was replaced with an equimolar amount of B-34, yielding compound 344 (10.93 g); HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 700.2527 (theoretical value: 700.2515). Theoretical elemental content (%) C 52 H 32 N₂O: C, 89.12; H, 4.60; N, 4.00. Measured elemental content (%): C, 89.09; H, 4.62; N, 4.03.

[0302] Synthesis example 24:

[0303]

[0304] Preparation of A-346:

[0305] Following the preparation method of A-67 in Synthesis Example 4, A1-67 was replaced with 55 mmol of A1-346, and b2-67 was 55 mmol, to obtain A-346 (14.83 g, 76%). The purity of the solid was determined by HPLC to be ≥99.81%.

[0306] Preparation of A2-346:

[0307] Under nitrogen protection, A-346 (14.19 g, 40 mmol), pinacol diborate (10.36 g, 40.8 mmol), Pd(dppf)Cl2 (585 mg, 0.8 mmol), KOAc (7.85 g, 80 mmol), and DMF (250 ml) were added to a reaction flask, and the mixture was stirred under reflux for 10 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 phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was recrystallized from chloroform:methanol in a 4:1 ratio to obtain A2-346 (14.64 g, 82%). The purity of the solid was determined by HPLC to be ≥99.88%.

[0308] Preparation of A3-346:

[0309] Under nitrogen protection, A2-346 (13.39 g, 30 mmol), c-346 (5.74 g, 30 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol), Na2CO3 (4.77 g, 45 mmol), THF (140 ml), and water (70 ml) were added to a reaction flask, and the mixture was stirred under reflux for 9 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 phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene:methanol (5:1) to obtain A3-346 (10.08 g, 78%), with a solid purity of ≥99.86% as determined by HPLC.

[0310] Preparation of compound 346:

[0311] Following the preparation method of compound 2 in Synthesis Example 1, A-2 was replaced with an equimolar amount of A3-346, and B-2 was replaced with an equimolar amount of B-34, yielding compound 67 (11.65 g, 75%); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 776.2836 (theoretical value: 776.2828). Theoretical elemental content (%) C 58 H 36 N₂O: C, 89.66; H, 4.67; N, 3.61. Measured elemental content (%): C, 89.69; H, 4.65; N, 3.58.

[0312] Synthesis example 25:

[0313]

[0314] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b2-354, and B-67 with an equimolar amount of B-354, yielding compound 354 (10.77 g); HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 717.3596 (theoretical value: 717.3582). Theoretical elemental content (%) C 52 H 15 D 17 N₂O: C, 86.99; H, 6.88; N, 3.90. Measured elemental content (%): C, 86.96; H, 6.86; N, 3.93.

[0315] Synthesis example 26:

[0316]

[0317] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b2-358, and B-67 with an equimolar amount of B-34, yielding compound 358 (11.13 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 772.2926 (theoretical value: 772.2910). Theoretical elemental content (%) C 55 H 40 N₂OSi: C, 85.46; H, 5.22; N, 3.62. Measured elemental content (%): C, 85.42; H, 5.25; N, 3.64.

[0318] Synthesis example 27:

[0319]

[0320] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b2-370, and B-67 with an equimolar amount of B-34, yielding compound 370 (12.36 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 834.3628 (theoretical value: 834.3610). Theoretical elemental content (%) C 62 H 46 N₂O: C, 89.18; H, 5.55; N, 3.35. Measured elemental content (%): C, 89.14; H, 5.58; N, 3.37.

[0321] Synthesis example 28:

[0322]

[0323] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-381, and B-67 was replaced with an equimolar amount of B-34, yielding compound 381 (10.81 g); HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 750.2683 (theoretical value: 750.2671). Theoretical elemental content (%) C 56 H 34 N₂O: C, 89.57; H, 4.56; N, 3.73. Measured elemental content (%): C, 89.55; H, 4.54; N, 3.76.

[0324] Synthesis example 29:

[0325]

[0326] Following the preparation method of compound 67 in Synthesis Example 4, a-67 was replaced with an equimolar amount of a-388, b1-67 with an equimolar amount of b1-339, and B-67 with an equimolar amount of B-34, yielding compound 388 (10.56 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 703.2714 (theoretical value: 703.2703). Theoretical elemental content (%) C 52 H 29 D3N2O: C, 88.74; H, 5.01; N, 3.98. Measured elemental content (%): C, 88.77; H, 5.03; N, 3.94.

[0327] Synthesis example 30:

[0328]

[0329] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-408, and B-67 was replaced with an equimolar amount of B-408, yielding compound 408 (12.04 g); HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 781.3157 (theoretical value: 781.3141). Theoretical elemental content (%) C 58 H 31 D5N2O: C, 89.09; H, 5.28; N, 3.58. Measured elemental content (%): C, 89.11; H, 5.31; N, 3.54.

[0330] Synthesis example 31:

[0331]

[0332] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-435, b2-67 with an equimolar amount of b-2, and B-67 with an equimolar amount of B-435, yielding compound 435 (11.21 g); HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 800.2833 (theoretical value: 800.2828). Theoretical elemental content (%) C 60 H 36 N₂O: C, 89.97; H, 4.53; N, 3.50. Measured elemental content (%): C, 89.93; H, 4.55; N, 3.52.

[0333] Synthesis example 32:

[0334]

[0335] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b-98, and B-67 with an equimolar amount of B-442, yielding compound 442 (11.05 g); HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 800.2836 (theoretical value: 800.2828). Theoretical elemental content (%) C 60 H 36 N₂O: C, 89.97; H, 4.53; N, 3.50. Measured elemental content (%): C, 89.94; H, 4.56; N, 3.53.

[0336] Synthesis example 33:

[0337]

[0338] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-346, b2-67 with an equimolar amount of b1-444, and B-67 with an equimolar amount of B-444, yielding compound 444 (11.91 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 850.2997 (theoretical value: 850.2984). Theoretical elemental content (%) C 64 H 38 N₂O: C, 90.33; H, 4.50; N, 3.29. Measured elemental content (%): C, 90.35; H, 4.52; N, 3.26.

[0339] Synthesis example 34:

[0340]

[0341] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, b2-67 with an equimolar amount of b-268, and B-67 with an equimolar amount of B-34, yielding compound 447 (11.60 g); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 816.3156 (theoretical value: 816.3141). Theoretical elemental content (%) C 61 H 40 N₂O: C, 89.68; H, 4.94; N, 3.43. Measured elemental content (%): C, 89.65; H, 4.96; N, 3.46.

[0342] Synthesis example 35:

[0343]

[0344] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b1-339, and B-2 was replaced with an equimolar amount of B-34, yielding compound 456 (12.34 g); HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 790.2637 (theoretical value: 790.2620). Theoretical elemental content (%) C 58 H 34 N2O2: C, 88.08; H, 4.33; N, 3.54. Measured elemental content (%): C, 88.11; H, 4.31; N, 3.52.

[0345] Synthesis example 36:

[0346]

[0347] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-508, b2-67 with an equimolar amount of b2-508, and B-67 with an equimolar amount of B-508, yielding compound 508 (11.20 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 777.2791 (theoretical value: 777.2780). Theoretical elemental content (%) C 57 H 35 N3O: C, 88.01; H, 4.54; N, 5.40. Measured elemental content (%): C, 88.04; H, 4.51; N, 5.42.

[0348] Synthesis example 37:

[0349]

[0350] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-346, and B-67 was replaced with an equimolar amount of B-510, yielding compound 510 (11.51 g); HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 750.2684 (theoretical value: 750.2671). Theoretical elemental content (%) C 56 H 34 N₂O: C, 89.57; H, 4.56; N, 3.73. Measured elemental content (%): C, 89.55; H, 4.54; N, 3.76.

[0351] Synthesis example 38:

[0352]

[0353] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, and B-67 was replaced with an equimolar amount of B-523, yielding compound 523 (11.61 g); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 816.3155 (theoretical value: 816.3141). Theoretical elemental content (%) C 61 H 40 N₂O: C, 89.68; H, 4.94; N, 3.43. Measured elemental content (%): C, 89.65; H, 4.96; N, 3.46.

[0354] Synthesis example 39:

[0355]

[0356] Following the preparation method of compound 346 in Synthesis Example 24, b1-346 was replaced with an equimolar amount of b1-339, c-346 with an equimolar amount of c-569, and B-34 with an equimolar amount of B-569, yielding compound 569 (11.41 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 826.2996 (theoretical value: 826.2984). Theoretical elemental content (%) C 62 H 38 N₂O: C, 90.05; H, 4.63; N, 3.39. Measured elemental content (%): C, 90.07; H, 4.65; N, 3.35.

[0357] Synthesis example 40:

[0358]

[0359] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-339, and B-67 was replaced with an equimolar amount of B-575, yielding compound 575 (11.23 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 790.2631 (theoretical value: 790.2620). Theoretical elemental content (%) C 58 H 34 N2O2: C, 88.08; H, 4.33; N, 3.54. Measured elemental content (%): C, 88.06; H, 4.36; N, 3.56.

[0360] Synthesis example 41:

[0361]

[0362] Preparation of D-578:

[0363] Under nitrogen protection, d-578 (21.40 g, 85.00 mmol), e-578 (20.10 g, 102.00 mmol), copper powder (7.02 g, 110.50 mmol), 18-crown ether-6 (2.25 g, 8.50 mmol), K₂CO₃ (14.10 g, 102.00 mmol), and DMF (250 mL) were added to a reaction flask, and the mixture was stirred under reflux for 12 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 (ethyl acetate: petroleum ether = 3:1) to obtain D-578 (23.14 g, yield 74%); the purity of the solid was ≥99.65% as determined by HPLC.

[0364] Preparation of E-578:

[0365] Under nitrogen protection, D-578 (20.07 g, 60.00 mmol), pinacol diborate (15.24 g, 60.00 mmol), Pd(dppf)Cl2 (219 mg, 0.30 mmol), KOAc (11.78 g, 120.00 mmol), and DMF (300 ml) were added to a reaction flask, and the mixture was 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 E-578 (22.88 g, 83%). The purity of the solid was determined by HPLC to be ≥99.72%.

[0366] F-578 preparation:

[0367] Under nitrogen protection, E-578 (20.67 g, 45.00 mmol), f-578 (9.09 g, 45.00 mmol), Pd(PPh3)4 (520 mg, 0.45 mmol), K2CO3 (12.44 g, 90.00 mmol), THF (200 ml), and water (100 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 F-578 (14.93 g, 73%). HPLC analysis showed that the solid purity was ≥99.81%.

[0368] Preparation of B-578:

[0369] Under nitrogen protection, F-578 (13.64 g, 30.00 mmol), triphenylphosphine (19.67 g, 75.00 mmol), and o-dichlorobenzene (120 ml) were added to a reaction flask, and the mixture was stirred under reflux for 12 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 B-578 (9.89 g, 78%); HPLC analysis showed that the solid purity was ≥99.89%.

[0370] Preparation of compound 578:

[0371] Following the preparation method of compound 2 in Synthesis Example 1, A-2 was replaced with an equimolar amount of A-456, and B-2 was replaced with an equimolar amount of B-578, yielding compound 578 (11.80 g, 71%); HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 830.2942 (theoretical value: 830.2933). Theoretical elemental content (%) C 61 H 38 N2O2: C, 88.17; H, 4.61; N, 3.37. Measured elemental content (%): C, 88.21; H, 4.63; N, 3.33.

[0372] Synthesis example 42:

[0373]

[0374] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b1-346, and B-2 was replaced with an equimolar amount of B-582, yielding compound 582 (11.71 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 790.2634 (theoretical value: 790.2620). Theoretical elemental content (%) C 58 H 34 N2O2: C, 88.08; H, 4.33; N, 3.54. Measured elemental content (%): C, 88.11; H, 4.31; N, 3.55.

[0375] Synthesis example 43:

[0376]

[0377] Following the preparation method of compound 578 in Synthesis Example 41, d-578 was replaced with an equimolar amount of d-590, e-578 with an equimolar amount of e-590, and A-456 with an equimolar amount of A-344, yielding compound 590 (12.00 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 832.2558 (theoretical value: 832.2548). Theoretical elemental content (%) C 60 H 36 N₂OS: C, 86.51; H, 4.36; N, 3.36. Measured elemental content (%): C, 86.54; H, 4.38; N, 3.32.

[0378] Synthesis example 44:

[0379]

[0380] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-593, and B-67 was replaced with an equimolar amount of B-593, yielding compound 593 (11.58 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 792.2607 (theoretical value: 792.2599). Theoretical elemental content (%) C 58 H 36 N2S: C, 87.85; H, 4.58; N, 3.53. Measured elemental content (%): C, 87.87; H, 4.54; N, 3.56.

[0381] Synthesis example 45:

[0382]

[0383] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-606, and B-67 was replaced with an equimolar amount of B-34, yielding compound 606 (10.75 g); HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 716.2295 (theoretical value: 716.2286). Theoretical elemental content (%) C 52 H 32 N₂S: C, 87.12; H, 4.50; N, 3.91. Measured elemental content (%): C, 87.10; H, 4.53; N, 3.89.

[0384] Synthesis example 46:

[0385]

[0386] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-606, and B-67 was replaced with an equimolar amount of B-612, yielding compound 612 (10.89 g); HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 766.2457 (theoretical value: 766.2443). Theoretical elemental content (%) C 56 H 34 N2S: C, 87.70; H, 4.47; N, 3.65. Measured elemental content (%): C, 87.74; H, 4.45; N, 3.62.

[0387] Synthesis example 47:

[0388]

[0389] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-606, b2-67 with an equimolar amount of b2-617, and B-67 with an equimolar amount of B-442, yielding compound 617 (10.39 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 741.2248 (theoretical value: 741.2239). Theoretical elemental content (%) C 53 H 31 N3S: C, 85.80; H, 4.21; N, 5.66. Measured elemental content (%): C, 85.83; H, 4.24; N, 5.63.

[0390] Synthesis example 48:

[0391]

[0392] Following the preparation method of compound 2 in Synthesis Example 1, a-2 was replaced with an equimolar amount of a-653, b-2 with an equimolar amount of b1-606, and B-2 with an equimolar amount of B-34, yielding compound 653 (11.89 g); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 836.2335 (theoretical value: 836.2320). Theoretical elemental content (%) C 59 H 36 N2S2: C, 84.66; H, 4.34; N, 3.35. Measured elemental content (%): C, 84.63; H, 4.37; N, 3.33.

[0393] Synthesis example 49:

[0394]

[0395] Following the preparation method of compound 346 in Synthesis Example 24, b1-346 was replaced with an equimolar amount of b1-663, b2-67 with an equimolar amount of b2-663, and c-346 with an equimolar amount of c-569, yielding compound 663 (11.56 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 837.2463 (theoretical value: 837.2450). Theoretical elemental content (%) C 58 H 35 N3O2S: C, 83.13; H, 4.21; N, 5.01. Measured elemental content (%): C, 83.10; H, 4.22; N, 5.04.

[0396] Synthesis example 50:

[0397]

[0398] Following the preparation method of compound 67 in Synthesis Example 4, a-67 was replaced with an equimolar amount of a-673, b1-67 with an equimolar amount of b1-606, and B-67 with an equimolar amount of B-673, yielding compound 673 (11.11 g); HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 816.2582 (theoretical value: 816.2599). Theoretical elemental content (%) C 60 H 36 N₂S: C, 88.21; H, 4.44; N, 3.43. Measured elemental content (%): C, 88.25; H, 4.41; N, 3.41.

[0399] Synthesis example 51:

[0400]

[0401] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-606, and B-67 was replaced with an equimolar amount of B-689, yielding compound 689 (10.19 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 717.2251 (theoretical value: 717.2239). Theoretical elemental content (%) C 51 H 31 N3S: C, 85.33; H, 4.35; N, 5.85. Measured elemental content (%): C, 85.35; H, 4.34; N, 5.82.

[0402] Synthesis example 52:

[0403]

[0404] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b1-663, and B-2 was replaced with an equimolar amount of B-701, yielding compound 701 (11.54 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 823.2132 (theoretical value: 823.2116). Theoretical elemental content (%) C 57 H 33 N3S2: C, 83.08; H, 4.04; N, 5.10. Measured elemental content (%): C, 83.06; H, 4.06; N, 5.13.

[0405] Synthesis example 53:

[0406]

[0407] Following the preparation method of compound 67 in Synthesis Example 4, a-67 was replaced with an equimolar amount of a-719, b1-67 with an equimolar amount of b1-719, and B-67 with an equimolar amount of B-98, yielding compound 719 (12.29 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 877.3219 (theoretical value: 877.3205). Theoretical elemental content (%) C 64 H 39 N5: C, 87.55; H, 4.48; N, 7.98. Measured elemental content (%): C, 87.58; H, 4.46; N, 7.94.

[0408] Synthesis example 54:

[0409]

[0410] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-723, and B-67 was replaced with an equimolar amount of B-34, yielding compound 723 (11.48 g); HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 775.2994 (theoretical value: 775.2987). Theoretical elemental content (%) C 58 H 37 N3: C, 89.78; H, 4.81; N, 5.42. Measured element content (%): C, 89.75; H, 4.83; N, 5.44.

[0411] Synthesis example 55:

[0412]

[0413] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-734, and B-67 was replaced with an equimolar amount of B-444, yielding compound 734 (11.33 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 775.2996 (theoretical value: 775.2987). Theoretical elemental content (%) C 58 H 37 N3: C, 89.78; H, 4.81; N, 5.42. Measured element content (%): C, 89.74; H, 4.84; N, 5.45.

[0414] Synthesis example 56:

[0415]

[0416] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-723, b2-67 with an equimolar amount of b2-738, and B-67 with an equimolar amount of B-738, yielding compound 738 (11.27 g); HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 793.2881 (theoretical value: 793.2893). Theoretical elemental content (%) C 58 H 36 FN3: C, 87.74; H, 4.57; N, 5.29. Measured elemental content (%): C, 87.78; H, 4.55; N, 5.26.

[0417] Synthesis example 57:

[0418]

[0419] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-802, and B-67 was replaced with an equimolar amount of B-582, yielding compound 738 (11.89 g); HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 825.3155 (theoretical value: 825.3144). Theoretical elemental content (%) C 62 H 39 N3: C, 90.15; H, 4.76; N, 5.09. Measured elemental content (%): C, 90.17; H, 4.78; N, 5.06.

[0420] Synthesis example 58:

[0421]

[0422] Following the preparation method of compound 67 in Synthesis Example 4, b1-67 was replaced with an equimolar amount of b1-808, and B-67 was replaced with an equimolar amount of B-2, yielding compound 808 (12.11 g); HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 864.3152 (theoretical value: 864.3141). Theoretical elemental content (%) C 65 H 40 N₂O: C, 90.25; H, 4.66; N, 3.24. Measured elemental content (%): C, 90.27; H, 4.62; N, 3.26.

[0423] Synthesis example 59:

[0424]

[0425] Following the preparation method of compound 2 in Synthesis Example 1, b-2 was replaced with an equimolar amount of b1-823, and B-2 was replaced with an equimolar amount of B-34, yielding compound 823 (10.12 g); HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 712.2639 (theoretical value: 712.2627). Theoretical elemental content (%) C 52 H 32 N4: C, 87.62; H, 4.52; N, 7.86. Measured elemental content (%): C, 87.65; H, 4.54; N, 7.82.

[0426] Device Examples

[0427] In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0428] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was ambient air at room temperature.

[0429] Example 1: Fabrication of Organic Electroluminescent Device 1

[0430] 2-TNATA was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 60 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 50 nm; Compound 34 and EM-1 of the present invention were vacuum-deposited on the hole transport layer at a ratio of 1:1 (wt%), and Ir(ppy)2(acac) was deposited at a doping amount of 8 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 32 nm; Bphen was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 6 nm; Alq3:BeBq2 = 1:1 (wt%) was vacuum-deposited on the hole blocking layer as an electron transport layer with a thickness of 45 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 0.5 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 120 nm.

[0431] Examples 2-32: Fabrication of Organic Electroluminescent Devices 2-32

[0432] Replacing compound 34 in the luminescent layer of Example 1 with compounds 67, 77, 98, 159, 206, 227, 268, 310, 311, 322, 344, 346, 354, 370, 388, 408, 435, 442, 456, 508, 523, 575, 582, 593, 606, 617, 663, 689, 723, 802, and 808 respectively, while keeping all other steps the same, organic electroluminescent devices 2-32 were obtained.

[0433] Comparative Examples 1-4: Fabrication of Comparative Organic Electroluminescent Devices 1-4

[0434] By replacing compound 34 in the luminescent layer of Example 1 with R-1, R-2, R-3, and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 4 were obtained.

[0435]

[0436]

[0437] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 32 and Comparative Examples 1 to 4 of the present invention are shown in Table 1.

[0438] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0439]

[0440]

[0441] As shown in Table 1, the organic electroluminescent device of the present invention has good photoelectric performance, specifically, it has a low driving voltage, high luminous efficiency, and long service life.

[0442] Example 33: Fabrication of organic electroluminescent device 33

[0443] 2-TNATA was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 60 nm; BPBPA was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 48 nm; Compound 2 and EM-1 of the present invention were vacuum-deposited on the hole transport layer at a ratio of 1:1 (wt%), and Ir(dpm)PQ2 was deposited at a doping amount of 5 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 35 nm; NBphen was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; Alq3:BeBq2 = 1:1 (wt%) was vacuum-deposited on the hole blocking layer as an electron transport layer with a thickness of 45 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 0.5 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 120 nm.

[0444] Examples 34-61: Fabrication of Organic Electroluminescent Devices 34-61

[0445] In Example 33, compound 2 in the light-emitting layer was replaced with compounds 39, 85, 101, 111, 215, 219, 250, 316, 319, 339, 344, 358, 381, 444, 447, 456, 510, 569, 578, 590, 612, 653, 673, 701, 719, 734, 738, and 823, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 34-61.

[0446] Comparative Examples 5-8: Fabrication of Comparative Organic Electroluminescent Devices 5-8

[0447] By replacing compound 2 in the light-emitting layer of Example 33 with R-1, R-2, R-3, and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 5-8 were obtained.

[0448]

[0449] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 33-61 and Comparative Examples 5-8 of this invention are shown in Table 2.

[0450] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0451]

[0452]

[0453] As shown in Table 2, the organic electroluminescent device of the present invention has good photoelectric performance, specifically, it has a low driving voltage, high luminous efficiency, and long service life.

[0454] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A fused cyclopentadienylcarbazole compound, characterized in that, The fused cyclopentadienylcarbazole compound is selected from at least one of Formula 1-1 and Formula 1-2. The ring A and ring C are independently selected from one of the following groups. The ring B is selected from one of the following groups. , + indicates a fusion site; f1 is selected from integers from 0 to 4, f2 is selected from integers from 0 to 6, f3 is selected from integers from 0 to 8, and f4 is selected from integers from 0 to 2. The R4 is selected from one of hydrogen, deuterium, and tritium; The T values ​​that are the same or different are selected from CH or N; each ring A, ring B, and ring C contains at most one N. Furthermore, at least one of ring A, ring B, and ring C is a fused ring with 10 to 18 cyclic atoms; Rx and Ry are independently selected from or And one selected from Another one selected ; The Ar1 is selected from one of the following groups. The n1 is selected from integers from 0 to 7, the n2 is selected from integers from 0 to 9, the n3 is selected from integers from 0 to 3, the n4 is selected from integers from 0 to 4, and the n5 is selected from integers from 0 to 5. The R that is the same or different is selected from one of hydrogen, deuterium, and tritium; The R's are the same or different and are selected from one of hydrogen, deuterium, and tritium, or two adjacent R's are bonded to each other to form substituted or unsubstituted benzene rings; The same or different Rw' is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; The Rws, whether identical or different, are selected from one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or unsubstituted phenyl, or two adjacent Rws are bonded to each other to form substituted or unsubstituted cyclopentane rings, cyclohexane rings, or adamantane rings. The Ar is selected from one of the following groups. The m1 is selected from integers from 0 to 7, the m2 is selected from integers from 0 to 9, the m3 is selected from integers from 0 to 3, the m4 is selected from integers from 0 to 4, the m5 is selected from integers from 0 to 5, the m6 is selected from integers from 0 to 2, the m7 is selected from integers from 0 to 6, the m8 is selected from integers from 0 to 8, and the m9 is selected from integers from 0 to 10. The R1s, whether identical or different, are selected from one of hydrogen, deuterium, and tritium; The same or different R1'' is selected from one of hydrogen, deuterium, tritium, cyano, halogen, trimethylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted adamantyl; The G1 is selected from O, S, C(Rg)2, and the Rg that is the same or different is selected from one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl. The R5s, whether identical or different, are selected from one of hydrogen, deuterium, and tritium; The group Selected from one of the following groups, ； The r1 is selected from integers from 0 to 3; the R0 that are the same or different are selected from one of hydrogen, deuterium, tritium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The Ar2 is selected from one of the following groups. The integer t1 is selected from 0 to 7, the integer t2 is selected from 0 to 9, the integer t3 is selected from 0 to 3, the integer t4 is selected from 0 to 4, the integer t5 is selected from 0 to 5, the integer t6 is selected from 0 to 2, the integer t7 is selected from 0 to 6, the integer t8 is selected from 0 to 8, and the integer t9 is selected from 0 to 10. The R6 that is the same or different is selected from one of hydrogen, deuterium, and tritium; The same or different R6'' is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The same or different R7s are selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl groups; The Rq that is the same or different is selected from one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; The L1 is selected from a single bond or one of the following groups: The L2 is independently selected from a single bond or a group as shown below. The L3 is independently selected from a single bond or one of the groups shown below. The e1 is selected from integers from 0 to 4, and the e3 is selected from integers from 0 to 3; The R3 that is the same or different is selected from one of hydrogen, deuterium, and tritium; The L is selected from a single bond or one of the following groups: b1 is selected from integers from 0 to 4; The R9s, whether identical or different, are selected from one of hydrogen, deuterium, and tritium; The substituents represented by "substituted or unsubstituted" include the following groups: deuterium and tritium.

2. The fused cyclopentadienoic carbazole compound according to claim 1, characterized in that, The Ar1 is selected from one of the following groups. 。 3. The fused cyclopentadienoic carbazole compound according to claim 1, characterized in that, The Ar is selected from one of the following groups. 。 4. The fused cyclopentadienoic carbazole compound according to claim 1, characterized in that, The Ar2 is selected from one of the following groups. 。 5. The fused cyclopentadienoic carbazole compound according to claim 1, characterized in that, One of rings A, B, and C is a fused ring with 10 to 18 cyclic atoms.

6. A fused cyclopentadienylcarbazole compound, characterized in that, The fused cyclopentadienylcarbazole compound is selected from at least one of the following structures. 。 7. An organic electroluminescent device, characterized in that, The organic electroluminescent device contains the fused cycloindo-carbazole compound as described in any one of claims 1 to 6.

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