An organic electroluminescent device

Abstract

The application provides an organic electroluminescence device, and relates to the technical field of organic electroluminescence. The organic electroluminescence device comprises an anode, an organic layer and a cathode, the organic layer comprises a hole transport region, the hole transport region comprises a first hole transport layer and a second hole transport layer, the first hole transport layer contains a carbazole derivative shown in structural formula 1, and the second hole transport layer contains an arylamine compound shown in structural formula 2. The organic electroluminescence device can not only effectively transport holes, but also make the transport of holes and electrons more balanced, and can also limit the carriers in the light-emitting layer, so that the holes and electrons can effectively combine in the light-emitting layer to form excitons to emit visible light. Therefore, the organic electroluminescence device has excellent photoelectric properties, specifically, has a low driving voltage, a high luminous efficiency and a long service life.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more specifically to an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are hailed as the 21st-century flat panel display and third-generation display technology. Compared with traditional display technologies, they have significant advantages in voltage characteristics, brightness, luminous efficiency, device weight, response speed, and viewing angle, making them the most promising panel display technology with broad market prospects.

[0003] Typically, OLEDs employ a layered or laminated structure. The structure of an organic light-emitting device (OLED) typically includes a substrate, an anode, an organic layer, and a cathode. The organic layer primarily enhances the efficiency and stability of the OLED and generally includes: a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), a hole blocking layer (HB), an electron transport layer (ETL), and an electron injection layer (EIL). Under the influence of an applied electric field, holes injected from the anode and electrons injected from the cathode (collectively referred to as charge carriers) migrate and recombine within the organic layer, transferring energy to the light-emitting material. This excitation excitons, when returning from the excited state to the ground state, emit radiation attenuation, releasing the attenuated energy as light, thus achieving light emission.

[0004] As the hole transport layer in an organic electroluminescent device, its basic function is to improve the transport efficiency of holes in the device and effectively block electrons within the light-emitting layer to achieve maximum recombination of charge carriers. At the same time, it reduces the energy barrier of holes during the injection process, improves the hole injection efficiency, and thus improves the brightness, efficiency and lifetime of the device.

[0005] Currently, research on organic light-emitting devices has been widely carried out in academia and industry, and a large number of high-performance organic light-emitting materials have been developed. Overall, the future direction of OLED is to develop high-efficiency, high-brightness, long-life, and low-cost white light devices and full-color display devices. However, the industrialization process of this technology still faces many key problems, such as the insufficient performance of the hole transport layer applied to OLEDs, which leads to problems such as high driving voltage, low luminous efficiency, or short lifespan in the entire OLED device. Therefore, developing an organic light-emitting device with better performance has strong practical significance. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides an organic electroluminescent device.

[0007] This invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode. The organic layer includes a hole transport region, which further comprises a first hole transport layer and a second hole transport layer. The first hole transport layer contains a carbazole derivative as shown in structural formula 1, and the second hole transport layer contains an aromatic amine compound as shown in structural formula 2.

[0008]

[0009] The Ar1 and Ar2 are independently selected from one of the following groups.

[0010]

[0011] The 'a' is selected from 0, 1, 2, 3, 4, or 5; the 'b's are the same or different and are selected from 0, 1, 2, 3, or 4; the R... a R b The cyclic group is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C7-C30 alicyclic and benzene rings, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or two adjacent groups bonded together to form a ring;

[0012] The R0 is the same or different from one of the following: hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and aromatic fused cycloalcohols, or two adjacent groups bonded together to form a ring;

[0013] The L, L1, and L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C7-C30 aliphatic ring, and fused cycloalkanes of benzene ring;

[0014] The R is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and fused cycloalkanes of aromatic rings;

[0015] The m that is the same or different is selected from 0, 1, 2, 3 or 4, and the R1 that is the same or different is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and aromatic fused cycloalcohols, or two adjacent groups bonded together to form a ring;

[0016]

[0017] Wherein, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently selected from the groups shown below.

[0018]

[0019] The 'c' is selected from 0, 1, 2, 3, 4, or 5, and the 'R' is selected from 5. c The same or different from one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocyclic alkyl, substituted or unsubstituted C7-C30 alicyclic and benzene ring fused cycloyl group, substituted or unsubstituted C6-C30 alicyclic and benzene ring fused cycloyl group, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl;

[0020] L3, L4, L5, L6, L7, and L8 are independently selected from one of the following: single bond, fused cycloalkanes of C7-C30 aliphatic rings and benzene rings, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted terphenylene.

[0021] The R 01 R 02 R 03 The independent group is selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C15 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 fused cycloyl group of alicyclic and aromatic rings, and substituted or unsubstituted C6-C30 fused cycloyl group of alicyclic and aromatic rings.

[0022] Beneficial Effects: The organic electroluminescent device of the present invention not only effectively transports holes, achieving a more balanced transport of holes and electrons, but also confines charge carriers within the emissive layer, enabling holes and electrons to effectively combine and form excitons to emit visible light. This is mainly due to the cooperation between the first and second hole transport layers in the organic electroluminescent device of the present invention, which matches the energy level of the hole transport region with that of the emissive layer, further facilitating hole injection / transport and effectively balancing charge carrier transport. Therefore, the organic electroluminescent device of the present invention exhibits superior photoelectric properties, specifically lower driving voltage, higher luminous efficiency, and longer lifespan. Detailed Implementation

[0023] 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.

[0024] In the compounds of the present 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.

[0025] In this invention, "C1-C30" in "substituted or unsubstituted C1-C30 alkyl groups" refers to the number of carbon atoms in the unsubstituted "alkyl group," excluding the number of carbon atoms in the substituents. Similarly, "C6-C30" in "substituted or unsubstituted C6-C30 aryl groups" refers to the number of carbon atoms in the unsubstituted "aryl group," excluding the number of carbon atoms in the substituents. Likewise, "C7-C30" in "substituted or unsubstituted C7-C30 fused alicyclic and aromatic ring groups" refers to the number of carbon atoms in the unsubstituted "fused alicyclic and aromatic ring groups," excluding the number of carbon atoms in the substituents. And so on.

[0026] In this specification, when the position of the substituent on the aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the aromatic ring. For example, Can represent And so on.

[0027] In this invention, "forming 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 bonding adjacent groups can be connected to another ring to form a spirostructure. An example is shown below:

[0028]

[0029] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, tetrahydronaphthalene, dihydroindene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0030] When the chain alkyl group described in this invention has three or more carbon atoms, it includes its isomers. For example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, isobutyl, sec-butyl, and tert-butyl, and so on.

[0031] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not replaced by any substituent. "Substituted" in "substituted or unsubstituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents can be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituted group represented by "substituted or unsubstituted" in the above-mentioned terms is selected from one of the following groups: deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C7-C30 alicyclic and benzene ring fused cycloalcohol, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl. Specifically, it can be selected from the following groups: deuterium, tritium, cyano, halogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl The following compounds are listed: alkyl, adamantyl, camphenyl, norbornel, isocamphenyl, fentanyl, phenyl, biphenyl, terphenyl, naphthyl, tetrahydronaphthyl, dihydroindyl, dihydronaphthyl, indyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, benzocyclooctyl, deuterated phenyl, per-deuterated phenyl, deuterated biphenyl, per-deuterated biphenyl, deuterated terphenyl, per-deuterated terphenyl, deuterated tetrahydronaphthyl, per-deuterated tetrahydronaphthyl, deuterated dihydroindyl, per-deuterated dihydroindyl, deuterated dihydronaphthyl, per-deuterated dihydronaphthyl, deuterated indyl, per-deuterated indyl, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, etc.

[0032] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a carbon atom in an aromatic hydrocarbon molecule. The aryl group has 6 to 60 carbon atoms, preferably 6 to 30, more preferably 6 to 18, and even more preferably 6 to 12. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. Examples of aryl groups include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, dibenzo[a]spirodifluorene, etc.

[0033] The heteroaryl group described in this invention refers to a monovalent group in which at least one carbon atom of an aryl group is replaced by a heteroatom. The heteroaryl group has a carbon number of C3 to C60, preferably C3 to C30, more preferably C3 to C12, and even more preferably C3 to C7. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of heteroaryl groups include, but are not limited to, the following groups: carbazole group, benzocarbazole group, dibenzocarbazole group, furanyl group, dibenzofuranyl group, benzodibenzofuranyl group, thiophene group, dibenzothiophene group, benzodibenzothiophene group, spirofluorenexanthracene group, spirofluorenethionthanthracene group, acridine group, phenothiazinyl group, phenotoxazinyl group, etc.

[0034] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has a carbon number of C1 to C30, preferably C1 to C10, and more preferably C1 to C6. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, etc.

[0035] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group has a carbon number of C3 to C30, preferably C3 to C15, and more preferably C3 to C10. Examples of the cycloalkyl group include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornelalkyl, camphenyl, isocamphenyl, fronyl, adamantyl, etc.

[0036] The heterocyclic alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a heterocyclic alkane molecule. The heteroatom can be one or more of N, O, S, Si, and P. The heterocyclic alkyl group has a carbon number of C2 to C30, preferably C2 to C20, more preferably C2 to C15, and particularly preferably C2 to C7. Examples may include, but are not limited to, azirrobutyl, tetrahydropyrrolyl, piperidinyl, azirroheptyl, morpholinyl, thiomorpholinyl, tetrahydrofuranyl, tetrahydrothiopheneyl, and dioxaneyl.

[0037] The fused cyclic group of alicyclic and benzene rings described in this invention refers to a monovalent group formed by the fusion of an alicyclic and a benzene ring and the removal of one hydrogen atom. The fused cyclic group of alicyclic and benzene rings has a carbon number of C7 to C30, preferably C7 to C20, and more preferably C7 to C15. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. Examples of fused cyclic groups of alicyclic and benzene rings include, but are not limited to, the following groups: tetrahydronaphthyl, dihydroindene, dihydronaphthyl, indene, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, benzocyclooctane, benzocyclooctenyl, dihydrophenanthrene, etc.

[0038] The fused alicyclic and aromatic ring group described in this invention refers to a monovalent group formed by the fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. The fused alicyclic and aromatic ring group has a carbon number of C7 to C30, preferably C7 to C20, and more preferably C7 to C15. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. The aromatic ring has a carbon number of C6 to C20, preferably C6 to C15, and more preferably C6 to C10. Examples of the fused alicyclic and aromatic ring group include, but are not limited to, the following groups: tetrahydronaphthyl, dihydroindenyl, dihydronaphthyl, indenyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, benzocyclooctyl, benzocyclooctenyl, dihydrophenanthrene, acenaphthene, etc.

[0039] The fused cyclic group of aliphatic heterocycle and benzene ring described in this invention refers to a monovalent group formed by fusion of an aliphatic heterocycle and a benzene ring, with one less hydrogen atom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The fused cyclic group of aliphatic heterocycle and benzene ring has a carbon number of C6 to C30, preferably C6 to C20, and more preferably C6 to C15. The aliphatic heterocycle has a carbon number of C2 to C20, preferably C2 to C15, and more preferably C2 to C10. Examples of the fused cyclic group of aliphatic heterocycle and benzene ring include, but are not limited to, the following groups: tetrahydroquinolinyl, dihydroindole, etc.

[0040] The fused cyclic group of aliphatic and aromatic rings described in this invention refers to a monovalent group formed by fusion of an aliphatic and aromatic ring and the removal of one hydrogen atom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The fused cyclic group of aliphatic and aromatic rings has a carbon number of C6 to C30, preferably C6 to C20, and more preferably C6 to C15. The aliphatic ring has a carbon number of C2 to C20, preferably C2 to C15, and more preferably C2 to C10. The aromatic ring has a carbon number of C6 to C20, preferably C6 to C15, and more preferably C6 to C10. Examples of fused cyclic groups of aliphatic and aromatic rings include, but are not limited to, the following groups: tetrahydroquinolinyl, dihydroindole, dihydrobenzoindole, etc.

[0041] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from a carbon atom in an aromatic hydrocarbon molecule. The arylene group has a carbon number of C6 to C60, preferably C6 to C30, more preferably C6 to C18, and even more preferably C6 to C12. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene groups include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, triphenylene, fluorene, benzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, etc.

[0042] The heteroaryl group refers to a divalent group in which at least one carbon atom in an aromatic hydrocarbon molecule is replaced by a heteroatom. The heteroaryl group has 3 to 60 carbon atoms, preferably 3 to 30, more preferably 3 to 12, and even more preferably 3 to 7. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl groups include, but are not limited to, the following groups: carbazolyl, benzo[a]carbazolyl, dibenzofuranyl, dibenzothiophene, etc.

[0043] The fused cyclic group of the alicyclic and benzene rings described in this invention refers to a divalent group formed by the fusion of an alicyclic and a benzene ring and the removal of two hydrogen atoms. The fused cyclic group of the alicyclic and benzene rings has a carbon number of C7 to C30, preferably C7 to C20, and more preferably C7 to C15. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. Examples of the fused cyclic group of the alicyclic and benzene rings include, but are not limited to, the following groups: tetrahydronaphthyl, dihydroindenyl, dihydronaphthyl, indenyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, benzocyclooctane, benzocyclooctenyl, dihydrophenanthrene, etc.

[0044] This invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode. The organic layer includes a hole transport region, which further comprises a first hole transport layer and a second hole transport layer. The first hole transport layer contains a carbazole derivative as shown in structural formula 1, and the second hole transport layer contains an aromatic amine compound as shown in structural formula 2.

[0045]

[0046] The Ar1 and Ar2 are independently selected from one of the following groups.

[0047]

[0048] The 'a' is selected from 0, 1, 2, 3, 4, or 5; the 'b's are the same or different and are selected from 0, 1, 2, 3, or 4; the R... a R b The cyclic group is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C7-C30 alicyclic and benzene rings, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or two adjacent groups bonded together to form a ring;

[0049] The R0 is the same or different from one of the following: hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and aromatic fused cycloalcohols, or two adjacent groups bonded together to form a ring;

[0050] The L, L1, and L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C7-C30 aliphatic ring, and fused cycloalkanes of benzene ring;

[0051] The R is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and fused cycloalkanes of aromatic rings;

[0052] The m that is the same or different is selected from 0, 1, 2, 3 or 4, and the R1 that is the same or different is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 alicyclic and aromatic fused cycloalcohols, or two adjacent groups bonded together to form a ring;

[0053]

[0054] Wherein, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently selected from the groups shown below.

[0055]

[0056] The 'c' is selected from 0, 1, 2, 3, 4, or 5, and the 'R' is selected from 5. cThe same or different from one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocyclic alkyl, substituted or unsubstituted C7-C30 alicyclic and benzene ring fused cycloyl group, substituted or unsubstituted C6-C30 alicyclic and benzene ring fused cycloyl group, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl;

[0057] L3, L4, L5, L6, L7, and L8 are independently selected from one of the following: single bond, fused cycloalkanes of C7-C30 aliphatic rings and benzene rings, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted terphenylene.

[0058] The R 01 R 02 R 03 The independent group is selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C15 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C7-C30 fused cycloyl group of alicyclic and aromatic rings, and substituted or unsubstituted C6-C30 fused cycloyl group of alicyclic and aromatic rings.

[0059] Preferably, the carbazole derivative is selected from one of the structures shown below.

[0060]

[0061] Preferably, Ar1 and Ar2 are independently selected from one of the following groups:

[0062]

[0063] The 'a' is selected from 0, 1, 2, 3, 4, or 5; the 'a1' is selected from 0, 1, 2, 3, or 4; the 'a2' is selected from 0, 1, 2, or 3; the 'a3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'a4' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'a5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the 'a6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the 'a7' is selected from 0, 1, or 2.

[0064] The R aR1' is independently 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted One of the following: phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted benzocyclooctyl;

[0065] The value of b is selected from 0, 1, 2, 3, or 4; the value of b` is selected from 0, 1, 2, or 3; the value of b1 is selected from 0, 1, 2, 3, 4, or 5; the value of b2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the value of b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0066] The same or different R0` is selected from one of hydrogen, deuterium, tritium, 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.

[0067] The R b R b1Independently 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted One of the following: substituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted benzocyclooctyl, or two adjacent groups bonded together to form a ring.

[0068] Preferably, Ar1 and Ar2 are independently selected from one of the following groups:

[0069]

[0070]

[0071]

[0072] The 'a' is selected from 0, 1, 2, 3, 4, or 5; the 'a1' is selected from 0, 1, 2, 3, or 4; the 'a2' is selected from 0, 1, 2, or 3; the 'a3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'a4' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'a5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the 'a6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the 'a7' is selected from 0, 1, or 2.

[0073] The R aR1' is independently 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 cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norborneol. One of the following: alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, and substituted or unsubstituted benzocycloheptane;

[0074] The value of b is selected from 0, 1, 2, 3, or 4; the value of b` is selected from 0, 1, 2, or 3; the value of b1 is selected from 0, 1, 2, 3, 4, or 5; the value of b2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the value of b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0075] The same or different R0` is selected from one of hydrogen, deuterium, tritium, 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.

[0076] The R b1 The same or different from one selected from hydrogen, deuterium, tritium, 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 phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, or substituted or unsubstituted benzocycloheptenyl, or two adjacent groups bonded together to form a ring;

[0077] The Rb Independently 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, etc. One of the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl.

[0078] Preferably, the Selected from one of the following groups,

[0079]

[0080] The R 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 heptyl, 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 One of the following: phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl;

[0081] The m is selected from 0, 1, 2, 3 or 4; the m1 is selected from 0, 1, 2, 3, 4, 5 or 6; the m2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0082] The R1 is the same as or different 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 benzene One of the following: alkyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl.

[0083] Preferably, the Selected from one of the following groups,

[0084]

[0085] R is selected from one of the following: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, 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 tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl.

[0086] The R1 is the same as or different from one selected from 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 tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, and substituted or unsubstituted benzocycloheptane.

[0087] Preferably, L, L1, and L2 are independently selected from single bonds or one of the following groups:

[0088]

[0089] The d is selected from 0, 1, 2, 3 or 4, and the R d The same or different from one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, or substituted or unsubstituted benzocycloheptenyl, or two adjacent groups bonded together to form a ring.

[0090] Preferably, L, L1, and L2 are independently selected from single bonds or one of the following groups:

[0091]

[0092] The d is selected from 0, 1, 2, 3, or 4; the d1 is selected from 0, 1, 2, 3, 4, 5, or 6; the d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d3 is selected from 0, 1, or 2; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0093] The R d R dThe single compound 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl.

[0094] Preferably, the Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently selected from one of the following groups:

[0095]

[0096]

[0097] The 'c' is selected from 0, 1, 2, 3, 4, or 5; the 'c1' is selected from 0, 1, 2, 3, or 4; the 'c2' is selected from 0, 1, 2, or 3; the 'c3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'c4' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'c5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the 'c6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the 'c7' is selected from 0, 1, or 2.

[0098] The R cR2' is independently 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted The dihydronaphthyl, substituted or unsubstituted indole, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted azacyclobutyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted azacycloheptyl, substituted or unsubstituted morpholinyl, substituted or unsubstituted thiomorpholinyl, substituted or unsubstituted tetrahydrofuranyl, substituted or unsubstituted tetrahydrothiophenyl, substituted or unsubstituted dioxane, substituted or unsubstituted tetrahydroquinolinyl, substituted or unsubstituted dihydroindolyl.

[0099] Preferably, the Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently selected from one of the following groups:

[0100]

[0101]

[0102] The 'c' is selected from 0, 1, 2, 3, 4, or 5; the 'c1' is selected from 0, 1, 2, 3, or 4; the 'c2' is selected from 0, 1, 2, or 3; the 'c3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'c4' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'c5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the 'c6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the 'c7' is selected from 0, 1, or 2.

[0103] The R cR2' is independently 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted The dihydronaphthyl, substituted or unsubstituted indole, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted azacyclobutyl, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted azacycloheptyl, substituted or unsubstituted morpholinyl, substituted or unsubstituted thiomorpholinyl, substituted or unsubstituted tetrahydrofuranyl, substituted or unsubstituted tetrahydrothiophenyl, substituted or unsubstituted dioxane, substituted or unsubstituted tetrahydroquinolinyl, substituted or unsubstituted dihydroindolyl.

[0104] Preferably, L3, L4, L5, L6, L7, and L8 are independently selected from single bonds or one of the following groups:

[0105]

[0106] The 'e' is selected from 0, 1, 2, 3, or 4, and the 'R' is selected from 0, 1, 2, 3, or 4. e The same or different from one selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted benzocycloheptenyl, or substituted or unsubstituted benzocycloheptenyl, or two adjacent groups bonded together to form a ring.

[0107] Preferably, L3, L4, L5, L6, L7, and L8 are independently selected from single bonds or one of the following groups:

[0108]

[0109] The 'e' is selected from 0, 1, 2, 3, or 4; the 'e1' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'e2' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'e3' is selected from 0, 1, or 2; the 'e4' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'e5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0110] The R e R e The single compound 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl.

[0111] Preferably, the R 01 R 02 R 03 The compound is independently selected from hydrogen, deuterium, tritium, cyano, halogen, 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 phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted tetrahydropyrrole, and substituted or unsubstituted piperidinyl.

[0112] Preferably, the carbazole derivative represented by structural formula 1 is selected from one of the following structures.

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] The above lists some specific chemical structures of the carbazole derivatives shown in Structural Formula 1 of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Structural Formula 1 with substituents as defined above should be included.

[0136] Preferably, the aromatic amine compound represented by structural formula 2 is selected from one of the structures shown below.

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] The above lists some specific chemical structures of the aromatic amine compounds shown in Structural Formula 2 of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Structural Formula 2 with substituents defined above should be included.

[0158] In addition to the first hole transport layer and the second hole transport layer, the organic electroluminescent device of the present invention may also include functional layers such as a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, a light-emitting layer, and a capping layer. 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.

[0159] 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:

[0160] The anode of this invention effectively injects holes into an organic layer, and is preferably made of a material with a high work function. The anode material includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, conductive polymers, etc. Specific examples may include, but are not limited to, silver (Ag), copper (Cu), palladium (Pd), gold (Au), platinum (Pt), indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium oxide (In2O3), polypyrrole, polyaniline, poly(3-methylthiophene), etc., but are not limited to these.

[0161] The cathode of the present invention effectively injects electrons into an organic layer, and is preferably made of a material with a low work function. The cathode material includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include aluminum (Al), silver (Ag), copper (Cu), ytterbium (Yb), tin (Sn), palladium (Pd), lithium fluoride / aluminum (LiF / Al), cesium fluoride / aluminum (CsF / Al), lithium oxide / aluminum (LiO2 / Al), magnesium:silver (Mg:Ag), etc., but are not limited thereto.

[0162] The hole injection layer of the present invention improves hole injection efficiency and reduces the injection barrier between the anode and the hole transport layer. The hole injection layer material includes, but is not limited to, the following materials: phthalocyanine metal complexes, aromatic amine derivatives, polycyano conjugated organic compounds, polymers, etc. Specific examples may include copper phthalocyanine (CuPc), N,N'-bis[4-di(m-tolyl)aminophenyl]-N,N'-diphenylbenzidine (DNTPD), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonic acid) (PSS), etc., but are not limited to these.

[0163] The hole transport layer of this invention improves the balance between hole injection and transport in the device, while effectively blocking electrons within the light-emitting layer, thereby maximizing carrier recombination. The hole transport layer material 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, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N,N',N'-tetraphenylbenzidine (TPB), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline (TAPC), tris(4-carbazolyl-9-ylphenyl)amine (TCTA), polyvinylcarbazole (PVC), etc.

[0164] The light-emitting layer of this invention comprises, but is not limited to, the following materials: fused aromatic ring derivatives, heterocyclic compounds, silicon-containing compounds, metal complexes, etc. Specific examples may include tris[4-(pyrene)-phenyl]amine (TPyPA), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 4,4'-bis[10-(naphthyl-1-yl)anthracene-9-yl]biphenyl, 1,3,5-tris(pyrene-1-yl)phenyl (TPB3), 1,3, 5-Tris(carbazole-9-yl)benzene (TCP), 1,3-bis(carbazole-9-yl)benzene (MCP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 9,9-bis[4-(carbazole-9-yl)-phenyl]fluorene (FL-2CBP), 2,8-bis(9H-carbazole-9-yl)dibenzo[b,d]thiophene (DCzDBT), 1,3-bis(triphenylsilyl)benzene (UGH-3), 8-hydroxyquinoline aluminum (Alq3), etc., but not limited to these.

[0165] The light-emitting layer of this invention uses doped materials including, but not limited to, the following: styreneamine compounds, aromatic amine derivatives, fused aromatic compounds, heterocyclic compounds, metal complexes, etc. Specific examples may include 1,4-bis-[4-(N,N-diphenyl)amino]styrene-benzene (DSA-Ph), 4,4'-BIS(9-ethyl-3-carbazole)-1,1'-biphenyl (BCzVBi), 2,7-bis[4-(diphenylamine)styrene]-9,9-spirodifluorene (Spiro-BDAVBi), N... 10 N 10 N 10 ',N 10Tetraphenyl-9,9'-bianthracite-10,10'-hydrazine (BA-TAD), 2,5,8,11-tetratert-butylperylene (TBPe), N,N'-dimethyl-quinacridone (DMQA), 4-(dicyanomethyl)-2-methyl-6-(1,1,7,7-tetramethyletherenyl-9-enyl)-4H-pyran (DCJT), bis(2,4-difluorophenylpyrido)tetra(1-pyrazolyl)iridium(III)borate (FIr6), tri(2-phenylpyridinium)iridium (Ir(ppy)3), bis(2-benzo[b]thiophene-2-ylpyridine)(acetylacetone)iridium(III) (Ir(btp)2(acac)), etc., but not limited to these.

[0166] The hole-blocking layer of the present invention has the function of blocking holes within the light-emitting layer and improving the binding rate of electrons and holes. The hole-blocking layer material includes, but is not limited to, the materials described below, such as metal complexes, imidazole derivatives, and phenanthroline derivatives. Specific examples may include bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but are not limited thereto.

[0167] The electron transport layer of this invention improves the balance between electron injection and transport in the device. The electron transport layer material includes, but is not limited to, the following: metal complexes, imidazole derivatives, pyridine derivatives, triazine derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, etc. Specific examples may include bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 8-hydroxyquinoline aluminum (Alq3), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 2-(4-biphenyl)-5- (4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-tert-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), 3-phenyl-4-(1'-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 2-(naphth-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), etc., but not limited to these.

[0168] The electron injection layer of this invention improves electron injection efficiency and reduces the injection barrier between the cathode and the electron transport layer. The electron injection layer material includes, but is not limited to, the materials described below, such as metals, metal oxides, and metal compounds. Specific examples may include, but are not limited to, calcium (Ca), barium (Ba), molybdenum oxide (MoO3), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), cesium fluoride (CsF), etc.

[0169] 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.

[0170] The organic electroluminescent device of this invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, flat-screen TVs, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, etc.

[0171] Synthesis Examples

[0172] There are no particular limitations on the preparation method of the carbazole derivative shown in structural formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reactions, etc. The carbazole derivative shown in structural formula 1 of this invention can be prepared using the synthetic route shown below.

[0173]

[0174] There are no particular limitations on the preparation method of the aromatic amine compound shown in structural formula 2 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reactions, etc. The aromatic amine compound shown in structural formula 2 of the present invention can be prepared using the synthetic route shown below.

[0175]

[0176] X1, X2, and X3 are selected from halogens, such as Cl, Br, and I.

[0177] 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.

[0178] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0179] [Synthetic Example 1] Synthesis of Compound 16

[0180]

[0181] Synthetic intermediates 1-16:

[0182] Under nitrogen protection, a-16 (147.00 mmol, 14.43 g), b-16 (140.00 mmol, 40.77 g), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (1.40 mmol, 1.02 g), sodium tert-butoxide (210.00 mmol, 20.18 g), and 400 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from ethyl acetate to give intermediate 1-16 (35.84 g, yield 83%). The purity of the solid was ≥99.75% as determined by HPLC.

[0183] Synthesized compound 16:

[0184] Under nitrogen protection, C-16 (29.00 mmol, 9.13 g), intermediate 1-16 (104.00 mmol, 32.20 g), tris(benzylacetone)palladium (0.696 mmol, 637 mg), tri-tert-butylphosphine (5.57 mmol, 1.13 g), sodium tert-butoxide (261 mmol, 25.08 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 7.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 16 (21.98 g, yield 76%). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrometry m / z: 996.6926 (theoretical value: 996.6903). Theoretical elemental content (%) C 72 H 60 D 15 N3: C, 86.70; H, 9.09; N, 4.21. Measured elemental content (%): C, 86.67; H, 9.14; N, 4.18.

[0185] [Synthetic Example 2] Synthesis of Compound 21

[0186]

[0187] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-21, and all other steps were the same, yielding compound 21 (19.37 g). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 981.5944 (theoretical value: 981.5961). Theoretical elemental content (%) C 72 H 75 N3: C, 88.03; H, 7.70; N, 4.28. Measured elemental content (%): C, 88.00; H, 7.71; N, 4.25.

[0188] [Synthetic Example 3] Synthesis of Compound 43

[0189]

[0190] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-43, and b-16 was replaced with an equimolar amount of b-43, with all other steps remaining the same, yielding compound 43 (15.63 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 699.3629 (theoretical value: 699.3613). Theoretical elemental content (%) C 51 H 45 N3: C, 87.52; H, 6.48; N, 6.00. Measured elemental content (%): C, 87.50; H, 6.51; N, 6.01.

[0191] [Synthetic Example 4] Synthesis of Compound 61

[0192]

[0193] Synthetic intermediates 1-61:

[0194] According to the preparation method of intermediate 1-16 in Synthesis Example 1, a-16 (126.00 mmol) was replaced with a-21 (189.00 mmol), and b-16 (120.00 mmol) was replaced with b-43 (180.00 mmol), to obtain intermediate 1-61 (27.72 g, yield 91%), and the solid purity was determined by HPLC to be ≥99.46%.

[0195] Synthetic intermediate 2-61:

[0196] According to the preparation method of intermediate 1-16 in Synthesis Example 1, a-16 (126.00 mmol) was replaced with a-61 (63.00 mmol), and b-16 (120.00 mmol) was replaced with b-61 (60.00 mmol) to obtain intermediate 2-61 (14.38 g, yield 87%). The purity of the solid was determined by HPLC to be ≥99.59%.

[0197] Synthetic A-61:

[0198] Under nitrogen protection, c-61 (60.00 mmol, 16.22 g), intermediate 1-61 (123.00 mmol, 20.81 g), palladium acetate (2.40 mmol, 539 mg), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (8.40 mmol, 4.00 g), sodium tert-butoxide (300.00 mmol, 28.83 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 4.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography (dichloromethane:petroleum ether = 1:4) to obtain A-61 (21.72 g, yield 81%). The purity of the solid was ≥99.62% as determined by HPLC.

[0199] Synthesized compound 61:

[0200] Under nitrogen protection, A-61 (35.00 mmol, 15.64 g), intermediate 2-61 (36.75 mmol, 10.12 g), tris(dibenzylacetone)palladium (0.175 mmol, 160 mg), tri-tert-butylphosphine (1.40 mmol, 283 mg), sodium tert-butoxide (70 mmol, 6.73 g), and 150 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 7 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 61 (18.73 g, yield 78%). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 685.3443 (theoretical value: 685.3457). Theoretical elemental content (%) C 50 H 43 N3: C, 87.55; H, 6.32; N, 6.13. Measured elemental content (%): C, 87.58; H, 6.30; N, 6.16.

[0201] [Synthetic Example 5] Synthesis of Compound 89

[0202]

[0203] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-43, and b-16 was replaced with an equimolar amount of b-89. All other steps were the same, yielding compound 89 (15.97 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 714.4567 (theoretical value: 714.4555). Theoretical elemental content (%) C 51H 30 D 15 N3: C, 85.67; H, 8.45; N, 5.88. Measured elemental content (%): C, 85.72; H, 8.43; N, 5.86.

[0204] [Synthetic Example 6] Synthesis of Compound 150

[0205]

[0206] In Synthesis Example 4, b-43 was replaced with an equimolar amount of b-16, a-61 with an equimolar amount of a-150, and b-61 with an equimolar amount of b-43, with all other steps remaining the same, yielding compound 150 (21.76 g). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 887.5186 (theoretical value: 887.5178). Theoretical elemental content (%) C 65 H 65 N3: C, 87.89; H, 7.38; N, 4.73. Measured elemental content (%): C, 87.92; H, 7.40; N, 4.70.

[0207] [Synthetic Example 7] Synthesis of Compound 213

[0208]

[0209] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-213, a-61 with an equimolar amount of a-21, and b-61 with an equimolar amount of b-213, while other steps remained the same, yielding compound 61 (20.26 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 781.4381 (theoretical value: 781.4396). Theoretical elemental content (%) C 57 H 55 N3: C, 87.54; H, 7.09; N, 5.37. Measured elemental content (%): C, 87.56; H, 7.06; N, 5.40.

[0210] [Synthetic Example 8] Synthesis of Compound 228

[0211]

[0212] In Synthesis Example 1, c-16 was replaced with an equimolar amount of c-228, a-16 with an equimolar amount of intermediate a-213, and b-16 with an equimolar amount of intermediate b-43. All other steps were the same, yielding compound 228 (16.35 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 741.4095 (theoretical value: 741.4083). Theoretical elemental content (%) C 54 H 51 N3: C, 87.41; H, 6.93; N, 5.66. Measured elemental content (%): C, 87.39; H, 6.90; N, 5.68.

[0213] [Synthetic Example 9] Synthesis of Compound 281

[0214]

[0215] In Synthesis Example 4, a-61 was replaced with an equimolar amount of a-21, and b-61 was replaced with an equimolar amount of b-281, with all other steps remaining the same, yielding compound 281 (18.13 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 655.3001 (theoretical value: 655.2987). Theoretical elemental content (%) C 48 H 37 N3: C, 87.91; H, 5.69; N, 6.41. Measured elemental content (%): C, 87.88; H, 5.67; N, 6.43.

[0216] [Synthetic Example 10] Synthesis of Compound 305

[0217]

[0218] Synthetic intermediate 2-305:

[0219] According to the preparation method of intermediate 1-16 in Synthesis Example 1, a-16 (126 mmol) was replaced with a-21 (63 mmol), and b-16 (120.00 mmol) was replaced with b-305 (60.00 mmol), to obtain intermediate 2-305 (16.58 g, yield 86%), and the solid purity was determined by HPLC to be ≥99.62%.

[0220] Synthetic intermediate A0-305:

[0221] Under nitrogen protection, c-305 (90.00 mmol, 28.56 g), intermediate 1-61 (94.50 mmol, 15.99 g), palladium acetate (0.90 mmol, 202 mg), tri-tert-butylphosphine (3.60 mmol, 728 mg), sodium tert-butoxide (225.00 mmol, 21.62 g), and 350 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 5.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography (dichloromethane:n-hexane = 1:5) to obtain intermediate A0-305 (26.79 g, yield 83%). The purity of the solid was ≥99.53% as determined by HPLC.

[0222] Synthetic intermediate A-305:

[0223] Under nitrogen protection, intermediates A0-305 (60.00 mmol, 21.52 g), 1-43 (63.00 mmol, 13.19 g), palladium acetate (0.90 mmol, 202 mg), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (2.70 mmol, 1.29 g), sodium tert-butoxide (180.00 mmol, 17.30 g), and 250 mL of toluene were added to a reaction flask. The mixture was stirred and heated to reflux for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography (dichloromethane:petroleum ether = 1:10) to obtain intermediate A-305 (23.09 g, yield 79%). The purity of the solid was ≥99.71% as determined by HPLC.

[0224] Synthesized compound 305:

[0225] Under nitrogen protection, A-305 (35.00 mmol, 17.05 g), intermediate 2-305 (36.75 mmol, 9.02 g), tris(dibenzylacetone)palladium (0.175 mmol, 160 mg), tri-tert-butylphosphine (1.40 mmol, 283 mg), sodium tert-butoxide (70 mmol, 6.73 g), and 150 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 305 (20.81 g, yield 77%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 771.3642 (theoretical value: 771.3613). Theoretical elemental content (%) C 57 H 45N3: C, 88.68; H, 5.88; N, 5.44. Measured elemental content (%): C, 88.65; H, 5.86; N, 5.48.

[0226] [Synthetic Example 11] Synthesis of Compound 309

[0227]

[0228] Synthesize r2-309:

[0229] Under nitrogen protection, r1-309 (120.00 mmol, 25.45 g), pinacol diborate (132.00 mmol, 33.52 g), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (1.20 mmol, 878 mg), potassium acetate (360.00 mmol, 35.33 g), and N,N-dimethylformamide (400 mL) were added to a reaction flask. The mixture was heated for 5 hours. After the reaction was completed, water was added, and the mixture was extracted with dichloromethane. The liquid was separated, and the organic phase was washed three times with distilled water. The solution was dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The mixture was cooled to allow crystallization, filtered, and the resulting solid was recrystallized from toluene to obtain r2-309 (225.81 g, yield 83%) with an HPLC purity ≥99.15%.

[0230] Synthetic a-309:

[0231] Under nitrogen protection, b-89 (80.00 mmol, 12.96 g), r2-309 (88.00 mmol, 22.81 g), potassium carbonate (160 mmol, 22.11 g), tetraphenylphosphine palladium (0.80 mmol, 924 mg), and 200 mL of toluene / ethanol / water (3:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene to obtain a-309 (13.72 g, yield 80%). The purity of the solid was determined by HPLC to be ≥99.20%.

[0232]

[0233] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-43, b-43 with an equimolar amount of b-89, a-61 with an equimolar amount of a-309, and b-61 with an equimolar amount of b-89, while the other steps remained the same, yielding compound 309 (20.92 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 795.5196 (theoretical value: 795.5182). Theoretical elemental content (%) C 57 H 29 D 20 N3: C, 85.99; H, 8.73; N, 5.28. Measured elemental content (%): C, 85.93; H, 8.76; N, 5.30.

[0234] [Synthetic Example 12] Synthesis of Compound 313

[0235]

[0236] In Synthesis Example 4, a-21 was replaced with an equimolar amount of intermediate a-43, a-61 with an equimolar amount of a-313, and b-61 with an equimolar amount of b-89. All other steps were the same, yielding compound 313 (19.71 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 740.3915 (theoretical value: 740.3927). Theoretical elemental content (%) C 54 H 40 D5N3: C, 87.53; H, 6.80; N, 5.67. Measured elemental content (%): C, 87.49; H, 6.85; N, 5.69.

[0237] [Synthetic Example 13] Synthesis of Compound 329

[0238]

[0239] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-329, a-61 with an equimolar amount of a-329, and b-61 with an equimolar amount of b-281, while the other steps remained the same, yielding compound 329 (21.38 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 859.4875 (theoretical value: 859.4865). Theoretical elemental content (%) C 63 H 61 N3: C, 87.97; H, 7.15; N, 4.89. Measured elemental content (%): C, 88.00; H, 7.16; N, 4.87.

[0240] [Synthetic Example 14] Synthesis of Compound 341

[0241]

[0242] In Synthesis Example 10, a-43 was replaced with an equimolar amount of a-21, b-43 with an equimolar amount of b-341, and b-305 with an equimolar amount of b-281, with all other steps remaining the same, yielding compound 341 (22.94 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 839.4256 (theoretical value: 839.4239). Theoretical elemental content (%) C 62 H 53 N3: C, 88.64; H, 6.36; N, 5.00. Measured elemental content (%): C, 88.62; H, 6.33; N, 5.04.

[0243] [Synthetic Example 15] Synthesis of Compound 370

[0244]

[0245] In Synthesis Example 4, a-61 was replaced with an equimolar amount of a-370, and b-61 was replaced with an equimolar amount of b-281, with all other steps remaining the same, yielding compound 370 (20.38 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 765.4067 (theoretical value: 765.4083). Theoretical elemental content (%) C 56 H 51 N3: C, 87.80; H, 6.71; N, 5.49. Measured elemental content (%): C, 87.82; H, 6.70; N, 5.47.

[0246] [Synthetic Example 16] Synthesis of Compound 382

[0247]

[0248] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-382, a-61 with an equimolar amount of a-382, and b-61 with an equimolar amount of b-382, while the other steps remained the same, yielding compound 382 (20.90 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 817.4407 (theoretical value: 817.4396). Theoretical elemental content (%) C 60 H 55 N3: C, 88.09; H, 6.78; N, 5.14. Measured element content (%): C, 88.12; H, 6.75; N, 5.15.

[0249] [Synthetic Example 17] Synthesis of Compound 387

[0250]

[0251] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-387, a-61 with an equimolar amount of a-387, and b-61 with an equimolar amount of b-281, while other steps remained the same, yielding compound 387 (20.27 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 839.5083 (theoretical value: 839.5055). Theoretical elemental content (%) C 61 H 49 D8N3: C, 87.20; H, 7.80; N, 5.00. Measured elemental content (%): C, 87.17; H, 7.77; N, 5.05.

[0252] [Synthetic Example 18] Synthesis of Compound 419

[0253]

[0254]

[0255] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-313, b-43 with an equimolar amount of b-89, a-61 with an equimolar amount of a-21, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 419 (19.74 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 741.3940 (theoretical value: 741.3928). Theoretical elemental content (%) C 54 H 31 D 10 N3: C, 87.41; H, 6.93; N, 5.66. Measured elemental content (%): C, 87.37; H, 6.91; N, 5.70.

[0256] [Synthetic Example 19] Synthesis of Compound 436

[0257]

[0258] In Synthesis Example 4, b-43 was replaced with an equimolar amount of b-281, a-61 with an equimolar amount of a-43, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 436 (20.27 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 771.3604 (theoretical value: 771.3613). Theoretical elemental content (%) C 57 H 45N3: C, 88.68; H, 5.88; N, 5.44. Measured element content (%): C, 88.71; H, 5.89; N, 5.42.

[0259] [Synthetic Example 20] Synthesis of Compound 484

[0260]

[0261] According to the preparation method of a-309 in Synthesis Example 11, b-89 was replaced with an equimolar amount of b-16 to obtain a-484 (21.16 g). The purity of the solid was determined by HPLC to be ≥98.85%.

[0262]

[0263] In Synthesis Example 4, b-43 was replaced with an equimolar amount of b-382, a-61 with an equimolar amount of a-484, and b-61 with an equimolar amount of b-89, while the other steps remained the same, yielding compound 484 (21.57 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 986.5358 (theoretical value: 986.5336). Theoretical elemental content (%) C 73 H 58 D5N3: C, 88.80; H, 6.94; N, 4.26. Measured elemental content (%): C, 88.83; H, 6.89; N, 4.29.

[0264] [Synthetic Example 21] Synthesis of Compound 502

[0265]

[0266] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-502, a-61 with an equimolar amount of a-21, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 502 (20.75 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 811.3939 (theoretical value: 811.3926). Theoretical elemental content (%) C 60 H 49 N3: C, 88.74; H, 6.08; N, 5.17. Measured elemental content (%): C, 88.76; H, 6.11; N, 5.15.

[0267] [Synthetic Example 22] Synthesis of Compound 545

[0268]

[0269] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-545, a-61 with an equimolar amount of a-21, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 545 (20.88 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 839.4250 (theoretical value: 839.4239). Theoretical elemental content (%) C 62 H 53 N3: C, 88.64; H, 6.36; N, 5.00. Measured elemental content (%): C, 88.62; H, 6.33; N, 5.06.

[0270] [Synthetic Example 23] Synthesis of Compound 558

[0271]

[0272]

[0273] In Synthesis Example 10, intermediate 1-43 was replaced with an equimolar amount of a-558, intermediate 2-305 was replaced with an equimolar amount of a-313, and intermediate 2-305 was replaced with an equimolar amount of b-558. All other steps were the same, yielding compound 558 (21.37 g). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 859.3912 (theoretical value: 859.3926). Theoretical elemental content (%) C 64 H 49 N3: C, 89.37; H, 5.74; N, 4.89. Measured elemental content (%): C, 89.40; H, 5.72; N, 4.91.

[0274] [Synthetic Example 24] Synthesis of Compound 560

[0275]

[0276] In Synthesis Example 10, intermediates 1-43 were modified by replacing a-43 with an equimolar amount of a-213 and b-43 with an equimolar amount of b-281. Similarly, intermediates 2-305 were modified by replacing a-21 with an equimolar amount of a-43 and b-305 with an equimolar amount of b-281. All other steps were the same, yielding compound 560 (21.11 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 825.4095 (theoretical value: 825.4083). Theoretical elemental content (%) C 61 H 51 N3: C, 88.69; H, 6.22; N, 5.09. Measured elemental content (%): C, 88.66; H, 6.25; N, 5.10.

[0277] [Synthetic Example 25] Synthesis of Compound 568

[0278]

[0279] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-313, and b-16 was replaced with an equimolar amount of b-213, with all other steps remaining the same, yielding compound 568 (21.72 g). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 1089.5985 (theoretical value: 1089.5961). Theoretical elemental content (%) C 81 H 75 N3: C, 89.21; H, 6.93; N, 3.85. Measured elemental content (%): C, 89.25; H, 6.90; N, 3.83.

[0280] [Synthetic Example 26] Synthesis of Compound 569

[0281]

[0282] In Synthesis Example 10, intermediates 1-43 were modified by replacing a-43 with an equimolar amount of a-21 and b-43 with an equimolar amount of b-281. Similarly, intermediates 2-305 were modified by replacing a-21 with an equimolar amount of a-313 and b-305 with an equimolar amount of b-281, with all other steps remaining the same. This yielded compound 569 (20.65 g), with a solid purity ≥99.91% as determined by HPLC. Mass spectrometry m / z: 807.3622 (theoretical value: 807.3613). Theoretical elemental content (%) C 60 H 45 N3: C, 89.19; H, 5.61; N, 5.20. Measured element content (%): C, 89.21; H, 5.58; N, 5.22.

[0283] [Synthetic Example 27] Synthesis of Compound 573

[0284]

[0285] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-21, and b-16 was replaced with an equimolar amount of b-281. All other steps remained the same, yielding compound 573 (17.34 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 807.3602 (theoretical value: 807.3613). Theoretical elemental content (%) C 60 H 45N3: C, 89.19; H, 5.61; N, 5.20. Measured elemental content (%): C, 89.22; H, 5.59; N, 5.22.

[0286] [Synthetic Example 28] Synthesis of Compound 576

[0287]

[0288] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-313, and b-16 was replaced with an equimolar amount of b-89. All other steps were the same, yielding compound 576 (17.89 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 822.4576 (theoretical value: 822.4555). Theoretical elemental content (%) C 60 H 30 D 15 N3: C, 87.55; H, 7.34; N, 5.11. Measured element content (%): C, 87.57; H, 7.31; N, 5.13.

[0289] [Synthetic Example 29] Synthesis of Compound 577

[0290]

[0291] In Synthesis Example 1, c-16 was replaced with an equimolar amount of c-228, a-16 with an equimolar amount of a-21, and b-16 with an equimolar amount of b-577. All other steps were the same, yielding compound 577 (17.11 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 807.3604 (theoretical value: 807.3613). Theoretical elemental content (%) C 60 H 45 N3: C, 89.19; H, 5.61; N, 5.20. Measured elemental content (%): C, 89.22; H, 5.63; N, 5.18.

[0292] [Synthetic Example 30] Synthesis of Compound 579

[0293]

[0294] In Synthesis Example 1, c-16 was replaced with an equimolar amount of c-579, a-16 with an equimolar amount of a-579, and b-16 with an equimolar amount of b-579, while the other steps remained the same, yielding compound 579 (20.36 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 975.5469 (theoretical value: 975.5491). Theoretical elemental content (%) C 72 H69 N3: C, 88.57; H, 7.12; N, 4.30. Measured elemental content (%): C, 88.53; H, 7.14; N, 4.33.

[0295] [Synthetic Example 31] Synthesis of Compound 581

[0296]

[0297] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-21, and b-16 was replaced with an equimolar amount of b-581. All other steps were the same, yielding compound 581 (18.35 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 819.4379 (theoretical value: 819.4367). Theoretical elemental content (%) C 60 H 33 D 12 N3: C, 87.87; H, 7.00; N, 5.12. Measured element content (%): C, 87.83; H, 7.03; N, 5.14.

[0298] [Synthetic Example 32] Synthesis of Compound 584

[0299]

[0300] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-584, and b-16 was replaced with an equimolar amount of b-89. All other steps were the same, yielding compound 584 (16.71 g). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 822.4565 (theoretical value: 822.4555). Theoretical elemental content (%) C 60 H 30 D 15 N3: C, 87.55; H, 7.34; N, 5.11. Measured elemental content (%): C, 87.59; H, 7.32; N, 5.08.

[0301] [Synthetic Example 33] Synthesis of Compound 618

[0302]

[0303] In Synthesis Example 4, b-43 was replaced with an equimolar amount of b-281, a-61 with an equimolar amount of a-43, and b-61 with an equimolar amount of b-281. All other steps were the same, yielding compound 618 (21.37 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 847.3940 (theoretical value: 847.3926). Theoretical elemental content (%) C 63H 49 N3: C, 89.22; H, 5.82; N, 4.95. Measured elemental content (%): C, 89.19; H, 5.85; N, 4.97.

[0304] [Synthetic Example 34] Synthesis of Compound 674

[0305]

[0306] In Synthesis Example 1, a-16 was replaced with an equimolar amount of a-43, and b-16 was replaced with an equimolar amount of b-281. All other steps were the same, yielding compound 674 (18.57 g). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 927.4569 (theoretical value: 927.4552). Theoretical elemental content (%) C 69 H 57 N3: C, 89.28; H, 6.19; N, 4.53. Measured elemental content (%): C, 89.31; H, 6.17; N, 4.51.

[0307] [Synthetic Example 35] Synthesis of Compound 711

[0308]

[0309] In Synthesis Example 4, b-43 was replaced with an equimolar amount of b-382, a-61 with an equimolar amount of a-711, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 711 (21.42 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 861.4066 (theoretical value: 861.4083). Theoretical elemental content (%) C 64 H 51 N3: C, 89.16; H, 5.96; N, 4.87. Measured elemental content (%): C, 89.14; H, 5.93; N, 4.90.

[0310] [Synthetic Example 36] Synthesis of Compound 736

[0311]

[0312] In Synthesis Example 10, intermediates 1-61 were modified by replacing b-43 with an equimolar amount of b-281, a-43 with an equimolar amount of a-213, and b-43 with an equimolar amount of b-281. In intermediates 2-305, a-21 was replaced with an equimolar amount of a-313, and b-305 with an equimolar amount of b-281. All other steps were the same, yielding compound 736 (22.33 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 937.4383 (theoretical value: 937.4396). Theoretical elemental content (%) C 70 H 55 N3: C, 89.61; H, 5.91; N, 4.48. Measured elemental content (%): C, 89.64; H, 5.89; N, 4.50.

[0313] [Synthetic Example 37] Synthesis of Compound 757

[0314]

[0315] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-313, b-43 with an equimolar amount of b-281, a-61 with an equimolar amount of a-21, and b-61 with an equimolar amount of b-43, while the other steps remained the same, yielding compound 757 (21.66 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 883.3940 (theoretical value: 883.3926). Theoretical elemental content (%) C 66 H 49 N3: C, 89.66; H, 5.59; N, 4.75. Measured elemental content (%): C, 89.69; H, 5.61; N, 4.73.

[0316] [Synthetic Example 38] Synthesis of Compound 765

[0317]

[0318] In Synthesis Example 4, a-21 was replaced with an equimolar amount of a-16, b-43 with an equimolar amount of b-765, a-61 with an equimolar amount of a-313, and b-61 with an equimolar amount of b-281, while the other steps remained the same, yielding compound 765 (22.12 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 903.5194 (theoretical value: 903.5182). Theoretical elemental content (%) C 66 H 29 D 20N3: C, 87.67; H, 7.69; N, 4.65. Measured elemental content (%): C, 87.69; H, 7.63; N, 4.68.

[0319] [Synthetic Example 39] Synthesis of Compound HT-1

[0320]

[0321] Synthetic B-1:

[0322] Under nitrogen protection, toluene (150 mL), c-1 (60.00 mmol, 19.33 g), a-313 (60.00 mmol, 10.15 g), palladium acetate (0.90 mmol, 0.20 g), sodium tert-butoxide (120.00 mmol, 11.53 g), and tri-tert-butylphosphine (3.60 mmol, 0.73 g) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and then refluxed for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene / methanol (10 / 1) to give B-1 (21.18 g, yield 86%). The purity of the solid was ≥99.59% as determined by HPLC.

[0323] Synthesized compound HT-1:

[0324] Under nitrogen protection, toluene (150 mL), B-1 (35.00 mmol, 14.37 g), b-281 (35.00 mmol, 8.16 g), tris(dibenzylacetone)palladium (0.35 mmol, 0.32 g), sodium tert-butoxide (70.00 mmol, 6.73 g), and tri-tert-butylphosphine (2.80 mmol, 0.57 g) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and the mixture was refluxed for 6.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound HT-1 (16.35 g, yield 83%). The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrometry m / z: 562.2418 (theoretical value: 562.2409). Theoretical elemental content (%) C 42 H 30 N2: C, 89.65; H, 5.37; N, 4.98. Measured elemental content (%): C, 89.68; H, 5.35; N, 4.96.

[0325] [Synthetic Example 40] Synthesis of Compound HT-31

[0326]

[0327] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-31, and all other steps were the same, yielding compound HT-31 (17.89 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 638.2733 (theoretical value: 638.2722). Theoretical elemental content (%) C 48 H 34 N2: C, 90.25; H, 5.36; N, 4.39. Measured elemental content (%): C, 90.22; H, 5.34; N, 4.42.

[0328] [Synthetic Example 41] Synthesis of Compound HT-39

[0329]

[0330] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-39, a-313 with an equimolar amount of a0-39, and b-281 with an equimolar amount of b-581. All other steps were the same, yielding compound HT-39 (18.11 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 646.3236 (theoretical value: 646.3224). Theoretical elemental content (%) C 45 H 26 D8N2: C, 89.13; H, 6.54; N, 4.33. Measured elemental content (%): C, 89.08; H, 6.57; N, 4.34.

[0331] [Synthetic Example 42] Synthesis of Compound HT-145

[0332]

[0333] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-145, a-313 with an equimolar amount of a-502, and b-281 with an equimolar amount of b0-145, with all other steps remaining the same, yielding compound HT-145 (19.38 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 718.3359 (theoretical value: 718.3348). Theoretical elemental content (%) C 54 H 42 N2: C, 90.21; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.22; H, 5.86; N, 3.93.

[0334] [Synthetic Example 43] Synthesis of Compound HT-194

[0335]

[0336] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-194, a-313 with an equimolar amount of a0-194, and b-281 with an equimolar amount of b0-194, while other steps remained the same, yielding compound HT-194 (19.63 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 737.3806 (theoretical value: 737.3818). Theoretical elemental content (%) C 55 H 39 D5N2: C, 89.51; H, 6.69; N, 3.80. Measured elemental content (%): C, 89.56; H, 6.65; N, 3.83.

[0337] [Synthetic Example 44] Synthesis of Compound HT-230

[0338]

[0339] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-230, a-313 with an equimolar amount of a-21, and b-281 with an equimolar amount of b0-230, with all other steps remaining the same, yielding compound HT-230 (18.11 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 638.2714 (theoretical value: 638.2722). Theoretical elemental content (%) C 48 H 32 N2: C, 90.25; H, 5.36; N, 4.39. Measured elemental content (%): C, 90.28; H, 5.38; N, 4.36.

[0340] [Synthetic Example 45] Synthesis of Compound HT-231

[0341]

[0342] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-231, a-313 with an equimolar amount of a0-231, and b-281 with an equimolar amount of b-89. All other steps were the same, yielding compound HT-231 (19.40 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 719.3363 (theoretical value: 719.3349). Theoretical elemental content (%) C 54 H 33 D5N2: C, 90.09; H, 6.02; N, 3.89. Measured elemental content (%): C, 90.14; H, 5.99; N, 3.88.

[0343] [Synthetic Example 46] Synthesis of Compound HT-235

[0344]

[0345] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-235, a-313 with an equimolar amount of a0-231, and b-281 with an equimolar amount of b-765. All other steps were the same, yielding compound HT-235 (19.40 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 719.3334 (theoretical value: 719.3349). Theoretical elemental content (%) C 54 H 33 D5N2: C, 90.09; H, 6.02; N, 3.89. Measured elemental content (%): C, 90.14; H, 5.99; N, 3.91.

[0346] [Synthetic Example 47] Synthesis of Compound HT-236

[0347]

[0348] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-145, and b-281 was replaced with an equimolar amount of b0-236. All other steps were the same, yielding compound HT-236 (18.97 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 694.3361 (theoretical value: 694.3348). Theoretical elemental content (%) C 52 H 42 N2: C, 89.88; H, 6.09; N, 4.03. Measured elemental content (%): C, 89.91; H, 6.06; N, 4.02.

[0349] [Synthetic Example 48] Synthesis of Compound HT-240

[0350]

[0351] Intermediate c-1 in Synthesis Example 39 was replaced with an equimolar amount of intermediate c-31, and b-281 was replaced with an equimolar amount of b-16. All other steps were the same, yielding compound HT-240 (19.03 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 696.3518 (theoretical value: 696.3504). Theoretical elemental content (%) C 52 H 44 N2: C, 89.62; H, 6.36; N, 4.02. Measured elemental content (%): C, 89.65; H, 6.35; N, 4.04.

[0352] [Synthetic Example 49] Synthesis of Compound HT-253

[0353]

[0354] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-253, and b-281 was replaced with an equimolar amount of b-305. All other steps were the same, yielding compound HT-253 (19.05 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 718.3298 (theoretical value: 718.3286). Theoretical elemental content (%) C 54 H 34 D4N2: C, 90.22; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.25; H, 5.84; N, 3.93.

[0355] [Synthetic Example 50] Synthesis of Compound HT-260

[0356]

[0357] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-260, a-313 with an equimolar amount of a-579, and b-281 with an equimolar amount of b-16, with all other steps remaining the same, yielding compound HT-260 (19.98 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 776.4081 (theoretical value: 776.4069). Theoretical elemental content (%) C 58 H 44 D4N2: C, 89.65; H, 6.74; N, 3.61. Measured elemental content (%): C, 89.62; H, 6.72; N, 3.65.

[0358] [Synthetic Example 51] Synthesis of Compound HT-269

[0359]

[0360] Synthetic Y3-269:

[0361] Under nitrogen protection, starting materials y1-269 (80.00 mmol, 22.97 g), y2-269 (80.00 mmol, 18.52 g), tetrakis(triphenylphosphine)palladium (1.60 mmol, 1.85 g), potassium carbonate (156.00 mmol, 21.56 g), 450 mL toluene, 150 mL ethanol, and 150 mL water were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3.5 h. 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 dried over anhydrous magnesium sulfate, filtered, and the solvent was removed. The mixture was recrystallized from toluene / ethanol at a ratio of 4:1 to obtain intermediate y3-269 (25.52 g, yield 81%). HPLC analysis showed that the solid purity was ≥99.73%.

[0362] Synthesized compound HT-269:

[0363] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-269, a-313 with an equimolar amount of a-309, and b-281 with an equimolar amount of b-305. All other steps were the same, yielding compound HT-269 (18.53 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 799.3983 (theoretical value: 799.3975). Theoretical elemental content (%) C 60 H 41 D5N2: C, 90.07; H, 6.42; N, 3.50. Measured elemental content (%): C, 90.04; H, 6.46; N, 3.48.

[0364] [Synthetic Example 52] Synthesis of Compound HT-274

[0365]

[0366] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-274, a-313 with an equimolar amount of a0-274, and b-281 with an equimolar amount of b0-274. All other steps were the same, yielding compound HT-274 (17.12 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 603.3617 (theoretical value: 603.3600). Theoretical elemental content (%) C 44 H 29 D9N2: C, 87.52; H, 7.84; N, 4.64. Measured elemental content (%): C, 87.57; H, 7.81; N, 4.60.

[0367] [Synthetic Example 53] Synthesis of Compound HT-294

[0368]

[0369] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-294, and a-313 was replaced with an equimolar amount of a-558. All other steps were the same, yielding compound HT-294 (18.61 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 672.3517 (theoretical value: 672.3504). Theoretical elemental content (%) C 50 H 44 N2: C, 89.25; H, 6.59; N, 4.16. Measured elemental content (%): C, 89.26; H, 6.62; N, 4.13.

[0370] [Synthetic Example 54] Synthesis of Compound HT-297

[0371]

[0372] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-297, and a-313 was replaced with an equimolar amount of a-579. All other steps were the same, yielding compound HT-297 (17.49 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 616.2861 (theoretical value: 616.2878). Theoretical elemental content (%) C 46 H 36 N2: C, 89.58; H, 5.88; N, 4.54. Measured element content (%): C, 89.55; H, 5.90; N, 4.57.

[0373] [Synthetic Example 55] Synthesis of Compound HT-304

[0374]

[0375] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-253, a-313 with an equimolar amount of a-545, and b-281 with an equimolar amount of b-382. All other steps were the same, yielding compound HT-304 (18.67 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 696.3466 (theoretical value: 696.3443). Theoretical elemental content (%) C 52 H 36 D4N2: C, 89.62; H, 6.36; N, 4.02. Measured elemental content (%): C, 89.60; H, 6.34; N, 4.07.

[0376] [Synthetic Example 56] Synthesis of Compound HT-325

[0377]

[0378] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-325, and a-313 was replaced with an equimolar amount of a-502. All other steps were the same, yielding compound HT-325 (18.67 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 683.3362 (theoretical value: 683.3349). Theoretical elemental content (%) C 51 H 33 D5N2: C, 89.57; H, 6.34; N, 4.10. Measured elemental content (%): C, 89.61; H, 6.33; N, 4.12.

[0379] [Synthetic Example 57] Synthesis of Compound HT-350

[0380]

[0381] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-31, and a-313 was replaced with an equimolar amount of a-43. All other steps were the same, yielding compound HT-350 (15.40 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 602.2713 (theoretical value: 602.2722). Theoretical elemental content (%) C 45 H 34 N2: C, 89.67; H, 5.69; N, 4.65. Measured element content (%): C, 89.64; H, 6.72; N, 4.63.

[0382] [Synthetic Example 58] Synthesis of Compound HT-380

[0383]

[0384] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-380, a-313 with an equimolar amount of a0-380, and b-281 with an equimolar amount of b0-380. All other steps were the same, yielding compound HT-380 (19.03 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 696.3517 (theoretical value: 696.3504). Theoretical elemental content (%) C 52 H 44 N2: C, 89.62; H, 6.36; N, 4.02. Measured elemental content (%): C, 89.59; H, 6.38; N, 4.05.

[0385] [Synthetic Example 59] Synthesis of Compound HT-392

[0386]

[0387] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-31, a-313 with an equimolar amount of a-502, and b-281 with an equimolar amount of b-89. All other steps were the same, yielding compound HT-392 (17.23 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 607.3048 (theoretical value: 607.3036). Theoretical elemental content (%) C 51 H 33 D5N2: C, 88.92; H, 6.47; N, 4.61. Measured elemental content (%): C, 88.97; H, 6.44; N, 4.62.

[0388] [Synthetic Example 60] Synthesis of Compound HT-393

[0389]

[0390] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-31, a-313 with an equimolar amount of a-502, and b-281 with an equimolar amount of b-16, with all other steps remaining the same, yielding compound HT-393 (19.60 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 736.3807 (theoretical value: 736.3817). Theoretical elemental content (%) C 55 H 48 N2: C, 89.63; H, 6.56; N, 3.80. Measured elemental content (%): C, 89.66; H, 6.54; N, 3.82.

[0391] [Synthetic Example 61] Synthesis of Compound HT-394

[0392]

[0393] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-394, a-313 with an equimolar amount of a0-394, and b-281 with an equimolar amount of b-382. All other steps were the same, yielding compound HT-394 (20.08 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 754.3337 (theoretical value: 754.3348). Theoretical elemental content (%) C 57 H 42 N2: C, 90.68; H, 5.61; N, 3.71. Measured element content (%): C, 90.66; H, 5.64; N, 3.69.

[0394] [Synthetic Example 62] Synthesis of Compound HT-404

[0395]

[0396] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-404, and a-313 was replaced with an equimolar amount of a-484. All other steps were the same, yielding compound HT-404 (18.53 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 888.4458 (theoretical value: 888.4443). Theoretical elemental content (%) C 67 H 56 N2: C, 90.50; H, 6.35; N, 3.15. Measured elemental content (%): C, 90.54; H, 6.30; N, 3.17.

[0397] [Synthetic Example 63] Synthesis of Compound HT-413

[0398]

[0399] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-253, a-313 with an equimolar amount of a0-413, and b-281 with an equimolar amount of b0-413. All other steps were the same, yielding compound HT-413 (19.60 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 736.3767 (theoretical value: 736.3756). Theoretical elemental content (%) C 55 H 40 D4N2: C, 89.63; H, 6.56; N, 3.80. Measured elemental content (%): C, 89.68; H, 6.58; N, 3.76.

[0400] [Synthetic Example 64] Synthesis of Compound HT-416

[0401]

[0402] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-380, and a-313 was replaced with an equimolar amount of a0-416. All other steps were the same, yielding compound HT-416 (19.92 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 748.3827 (theoretical value: 748.3817). Theoretical elemental content (%) C 56 H 48N2: C, 89.80; H, 6.46; N, 3.74. Measured elemental content (%): C, 89.77; H, 6.48; N, 3.72.

[0403] [Synthetic Example 65] Synthesis of Compound HT-430

[0404]

[0405] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-235, a-313 with an equimolar amount of a-213, and b-281 with an equimolar amount of b-558. All other steps were the same, yielding compound HT-430 (18.92 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 692.3179 (theoretical value: 692.3191). Theoretical elemental content (%) C 52 H 40 N2: C, 90.14; H, 5.82; N, 4.04. Measured elemental content (%): C, 90.11; H, 5.80; N, 4.07.

[0406] [Synthetic Example 66] Synthesis of Compound HT-444

[0407]

[0408] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-444, a-313 with an equimolar amount of a0-444, and b-281 with an equimolar amount of b0-444. All other steps were the same, yielding compound HT-444 (19.27 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 714.3903 (theoretical value: 714.3912). Theoretical elemental content (%) C 53 H 42 D4N2: C, 89.03; H, 7.05; N, 3.92. Measured elemental content (%): C, 89.07; H, 7.02; N, 3.94.

[0409] [Synthetic Example 67] Synthesis of Compound HT-459

[0410]

[0411] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-459, a-313 with an equimolar amount of a-43, and b-281 with an equimolar amount of b0-230, with all other steps remaining the same, yielding compound HT-459 (19.39 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 728.3175 (theoretical value: 728.3191). Theoretical elemental composition (%) C55H40N2: C, 90.63; H, 5.53; N, 3.84. Measured elemental composition (%): C, 90.66; H, 5.52; N, 3.85.

[0412] [Synthetic Example 68] Synthesis of Compound HT-503

[0413]

[0414] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-503, a-313 with an equimolar amount of a-213, and b-281 with an equimolar amount of b-305. All other steps were the same, yielding compound HT-503 (18.92 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 692.3154 (theoretical value: 692.3139). Theoretical elemental content (%) C 52 H 40 N2: C, 90.14; H, 5.82; N, 4.04. Measured elemental content (%): C, 90.11; H, 5.84; N, 4.03.

[0415] [Synthetic Example 69] Synthesis of Compound HT-562

[0416]

[0417] Intermediate c-1 in Synthesis Example 39 was replaced with an equimolar amount of intermediate c-31, and b-281 was replaced with an equimolar amount of b0-562. All other steps were the same, yielding compound HT-562 (18.77 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 678.3045 (theoretical value: 678.3035). Theoretical elemental content (%) C 51 H 38 N2: C, 90.23; H, 5.64; N, 4.13. Measured elemental content (%): C, 90.25; H, 5.61; N, 4.11.

[0418] [Synthetic Example 70] Synthesis of Compound HT-576

[0419]

[0420] Intermediate c-1 in Synthesis Example 39 was replaced with an equimolar amount of intermediate c-31, and b-281 was replaced with an equimolar amount of b0-576. All other steps were the same, yielding compound HT-576 (20.77 g). HPLC analysis showed a solid purity ≥99.88%. Mass spectrometry m / z: 812.4148 (theoretical value: 812.4130). Theoretical elemental content (%) C 61 H 52 N2: C, 90.11; H, 6.45; N, 3.45. Measured elemental content (%): C, 90.08; H, 6.43; N, 3.48.

[0421] [Synthetic Example 71] Synthesis of Compound HT-611

[0422]

[0423] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-253, a-313 with an equimolar amount of a0-611, and b-281 with an equimolar amount of b0-611, with all other steps remaining the same, yielding compound HT-611 (20.20 g). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 783.4494 (theoretical value: 783.4477). Theoretical elemental content (%) C 58 H 33 D 13 N2: C, 88.85; H, 7.58; N, 3.57. Measured element content (%): C, 88.81; H, 7.61; N, 3.59.

[0424] [Synthetic Example 72] Synthesis of Compound HT-686

[0425]

[0426] Intermediate c-1 in Synthesis Example 39 was replaced with an equimolar amount of intermediate c-392, a-313 with an equimolar amount of a-502, and b-281 with an equimolar amount of b0-562. All other steps were the same, yielding compound HT-686 (19.38 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 718.3358 (theoretical value: 718.3348). Theoretical elemental content (%) C 54 H 42 N2: C, 90.21; H, 5.89; N, 3.90. Measured element content (%): C, 90.18; H, 5.90; N, 3.93.

[0427] [Synthetic Example 73] Synthesis of Compound HT-710

[0428]

[0429] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-31, a-313 with an equimolar amount of a-150, and b-281 with an equimolar amount of b0-710. All other steps were the same, yielding compound HT-710 (20.13 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 766.3359 (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, 90.85; H, 5.55; N, 3.63.

[0430] [Synthetic Example 74] Synthesis of Compound HT-713

[0431]

[0432] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-713, a-313 with an equimolar amount of a-309, and b-281 with an equimolar amount of b0-713. All other steps were the same, yielding compound HT-713 (20.58 g). HPLC analysis showed a solid purity ≥99.89%. Mass spectrometry m / z: 825.4149 (theoretical value: 825.4131). Theoretical elemental content (%) C 62 H 43 D5N2: C, 90.14; H, 6.47; N, 3.39. Measured elemental content (%): C, 90.17; H, 6.49; N, 3.35.

[0433] [Synthetic Example 75] Synthesis of Compound HT-734

[0434]

[0435] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-145, a-313 with an equimolar amount of a-213, and b-281 with an equimolar amount of b0-734. All other steps were the same, yielding compound HT-734 (20.23 g). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 780.3493 (theoretical value: 780.3504). Theoretical elemental content (%) C 59 H 44 N2: C, 90.73; H, 5.68; N, 3.59. Measured elemental content (%): C, 90.70; H, 5.71; N, 3.57.

[0436] [Synthetic Example 76] Synthesis of Compound HT-740

[0437]

[0438] In Synthesis Example 39, c-1 was replaced with an equimolar amount of c-740, a-313 with an equimolar amount of a-382, and b-281 with an equimolar amount of b0-740. All other steps were the same, yielding compound HT-740 (20.18 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 778.3335 (theoretical value: 778.3348). Theoretical elemental content (%) C 59 H 42 N2: C, 90.97; H, 5.43; N, 3.60. Measured elemental content (%): C, 90.99; H, 5.46; N, 3.57.

[0439] Device Examples

[0440] 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%.

[0441] 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.

[0442] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s; the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0443] Example 1: Fabrication of Organic Electroluminescent Device 1

[0444] DNTPD was vacuum-deposited as a hole injection layer with a thickness of 65 nm on an ITO (150 nm) anode; HT-274 of the present invention was vacuum-deposited as a first hole transport layer with a thickness of 27 nm on the hole injection layer; Compound 16 of the present invention was vacuum-deposited as a second hole transport layer with a thickness of 10 nm on the first hole transport layer; MCP:Ir(ppy)3 (5 wt%) was vacuum-deposited as a light-emitting layer with a thickness of 35 nm on the second hole transport layer; BAlq was vacuum-deposited as a hole blocking layer with a thickness of 5 nm on the light-emitting layer; Alq3 was vacuum-deposited as an electron transport layer with a thickness of 30 nm on the hole blocking layer; LiF was vacuum-deposited as an electron injection layer with a thickness of 1 nm on the electron transport layer; and Al was vacuum-deposited as a cathode with a thickness of 200 nm on the electron injection layer.

[0445] Examples 2-38: Fabrication of Organic Electroluminescent Devices 2-38

[0446] In Example 1, compound 16 in the second hole transport layer was replaced with compounds 21, 43, 61, 89, 150, 213, 228, 281, 305, 309, 313, 329, 341, 370, 382, ​​387, 419, 436, 484, 502, 545, 558, 560, 568, 569, 573, 576, 577, 579, 581, 584, 618, 674, 711, 736, 757, and 765. Similarly, compound HT-274 in the first hole transport layer was replaced with compounds HT-240, HT-713, HT-294, and HT-392. Compounds HT-444, HT-430, HT-740, HT-562, HT-404, HT-269, HT-413, HT-459, HT-611, HT-380, HT-686, HT-304, HT-235, HT-393, HT-325, HT-145, HT-297, HT-503, HT-734, HT-236, HT-1, HT-31, HT-194, HT-230, HT-39, HT-253, HT-260, HT-394, HT-350, HT-710, HT-416, HT-576, and HT-231 were used, with other steps being the same, to obtain organic electroluminescent devices 2 to 38.

[0447] Comparative Example 1: Fabrication of Comparative Organic Electroluminescent Device 1

[0448] DNTPD was vacuum-deposited as a hole injection layer with a thickness of 65 nm on an ITO (150 nm) anode; compound 89 of the present invention was vacuum-deposited as a hole transport layer with a thickness of 37 nm on the hole injection layer; MCP:Ir(ppy)3 (5 wt%) was vacuum-deposited as a light-emitting layer with a thickness of 35 nm on the hole transport layer; BAlq was vacuum-deposited as a hole blocking layer with a thickness of 5 nm on the light-emitting layer; Alq3 was vacuum-deposited as an electron transport layer with a thickness of 30 nm on the hole blocking layer; LiF was vacuum-deposited as an electron injection layer with a thickness of 1 nm on the electron transport layer; and Al was vacuum-deposited as a cathode with a thickness of 200 nm on the electron injection layer.

[0449] Comparative Examples 2-8: Fabrication of Comparative Organic Electroluminescent Devices 2-8

[0450] By replacing compound 89 in the hole transport layer of Comparative Example 1 with compounds HT-392, 569, HT-1, 584, HT-260, 674, and HT-350 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 2 to 8 were obtained.

[0451]

[0452] The luminescence characteristics of the organic electroluminescent devices prepared in Examples 1-38 and Comparative Examples 1-8 of this invention are shown in Table 1.

[0453] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0454]

[0455]

[0456] Compared with comparative devices, the organic electroluminescent devices 1-38 of the present invention have excellent characteristics such as low driving voltage, high luminous efficiency and long service life, indicating that the organic electroluminescent devices of the present invention can effectively transport holes and confine electrons and holes within the light-emitting layer, so that the two can effectively combine to form exciton luminescence.

[0457] 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. An organic electroluminescent device, characterized in that, The device includes an anode, an organic layer, and a cathode. The organic layer includes a hole transport region, which comprises a first hole transport layer and a second hole transport layer. The first hole transport layer contains a carbazole derivative as shown in structural formula 1, and the second hole transport layer contains an aromatic amine compound as shown in structural formula 2. The Ar1 and Ar2 are independently selected from one of the following groups: The 'a' is selected from 0, 1, 2, 3, 4, or 5; the 'a1' is selected from 0, 1, 2, 3, or 4; the 'a2' is selected from 0, 1, 2, or 3; the 'a3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'a4' is selected from 0, 1, 2, 3, 4, 5, or 6; and the 'a6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8. The R a The single element 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, and substituted or unsubstituted phenyl. The R1` is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The value of b is selected from 0, 1, 2, 3, or 4; the value of b` is selected from 0, 1, 2, or 3; the value of b1 is selected from 0, 1, 2, 3, 4, or 5; the value of b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the value of b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. The same or different R0` is selected from one of substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; The R b A benzene ring is formed independently from one of 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, or substituted or unsubstituted phenyl, or by bonding two adjacent groups. The R b1 The substance is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; The L, L1, and L2 are independently selected from single bonds or one of the following groups. The d is selected from 0, 1, 2, 3 or 4; the d1 is selected from 0, 1, 2, 3, 4, 5 or 6; the d2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R d R d The individual is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; R is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted indyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocycloheptane, and substituted or unsubstituted benzocycloheptenyl; the substituted group represented by "substituted or unsubstituted" in R is selected from one of the following groups: deuterium, tritium, methyl, ethyl, propyl, butyl, and adamantyl. The m that is the same or different is selected from 0, 1, 2, 3 or 4; the R1 that is the same or different is selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted phenyl; the R1' that is the same or different is selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted phenyl; or the two adjacent groups are bonded to form a benzene ring. Wherein, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently selected from one of the following groups. The 'c' is selected from 0, 1, 2, 3, 4, or 5; the 'c1' is selected from 0, 1, 2, 3, or 4; the 'c2' is selected from 0, 1, 2, or 3; the 'c3' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the 'c4' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'c6' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8. The R c The single element 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 heptyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, and substituted or unsubstituted phenyl. The R2' is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, and substituted or unsubstituted hexyl. The L3, L4, L5, L6, L7, and L8 are independently selected from single bonds or one of the following groups: The 'e' is selected from 0, 1, 2, 3, or 4; the 'e1' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'e2' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'e4' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The R e R e The individual 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 R 01 R 02 R 03 The substance is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; The substituent group represented by "substituted or unsubstituted" in the above-mentioned terms is selected from one of the following groups: deuterium, tritium, methyl, ethyl, propyl, and butyl.

2. The organic electroluminescent device according to claim 1, characterized in that, The Ar1 and Ar2 are independently selected from one of the following groups: 。 3. An organic electroluminescent device according to claim 1, characterized in that, The Selected from one of the following groups, The R is selected from substituted or unsubstituted phenyl groups; The same or different R1 is selected from one of hydrogen, deuterium, tritium, methyl, ethyl, propyl, and butyl.

4. An organic electroluminescent device according to claim 1, characterized in that, The L, L1, and L2 are independently selected from single bonds or one of the following groups. 。 5. An organic electroluminescent device according to claim 1, characterized in that, The Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are individually selected from one of the following groups. 。 6. An organic electroluminescent device according to claim 1, characterized in that, The L3, L4, L5, L6, L7, and L8 are independently selected from single bonds or one of the following groups: 。 7. An organic electroluminescent device according to claim 1, characterized in that, The carbazole derivative represented by structural formula 1 is selected from one of the structures shown below. 。 8. An organic electroluminescent device according to claim 1, characterized in that, The aromatic amine compound represented by structural formula 2 is selected from one of the structures shown below. 。

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