Oxazole derivative and organic electroluminescent device thereof

Abstract

The present application provides a kind of oxazole derivative and its organic electroluminescent device, it is related to organic electroluminescent material technical field.The oxazole derivative of formula 1 of the present application has good photoelectric performance, it is applied to the hole blocking layer or electron transport layer of organic electroluminescent device, and the device shows excellent performance, specifically as driving voltage is reduced, luminous efficiency is increased, service life is extended;In addition, the oxazole derivative of formula 1 of the present application is used as host material in organic electroluminescent device, and the device also shows excellent performance, is a kind of excellent organic electroluminescent material.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to an oxazole derivative and its organic electroluminescent device. Background Technology

[0002] In recent years, Organic Light-Emitting Diode (OLED) has become a very popular flat panel display technology globally because OLED displays do not require backlights compared to LCDs, allowing them to be extremely thin and light. Furthermore, OLED displays can use flexible substrates to achieve bending and folding effects. As a next-generation display technology, OLED is highly anticipated by the display industry, indicating a huge future for OLED display technology.

[0003] OLEDs emit light by sandwiching an organic light-emitting layer between two electrodes and then applying current. Their light-emitting mechanism is generally a dual-carrier injection mode. First, holes and electrons are injected into the organic functional layer from the anode and cathode, respectively, under the influence of an additional electric field. Then, under the influence of the additional electric field, holes and electrons migrate towards the electrodes with opposite charges. Finally, the carriers meet in the light-emitting layer, recombine to form excitons, and the excitons transfer energy to the organic light-emitting molecules, exciting them. The excited-state molecules emit photons during their return to the ground state. As organic light-emitting technology matures, the structure of devices becomes increasingly complex. Most organic light-emitting devices are multi-layered sandwich structures with dual-carrier (hole and electron) DC injection. They consist of a cathode, an anode, and various organic functional layers sandwiched between the electrodes. These organic functional layers generally include: a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL). Some complex OLED devices also incorporate hole blocking layers and electron blocking layers to improve their luminous efficiency. The blocking layer's main function is to block electrons and holes within the organic layer, allowing them to better combine and form excitons, thereby improving the device's luminous efficiency.

[0004] The key factor determining the luminous efficiency of OLEDs is the luminescent material, which must possess the following characteristics: high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed luminescent material layer. In organic materials, electron mobility is generally lower than hole mobility, and the balance between carrier injection and transport is a crucial factor affecting OLED device performance. Furthermore, there are fewer types of electron transport materials compared to hole transport materials, and their thermal stability and other properties also influence OLED device performance. Therefore, the development of novel electron transport materials is of paramount importance. Summary of the Invention

[0005] As a result of research aimed at solving the above-mentioned technical problems, the present invention provides an oxazole derivative, represented by the following formula 1.

[0006]

[0007] Wherein, X is selected from O, S or N(R) a ); The R a It is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic-heterocyclic group;

[0008] The rings A1, A2, and A3 are independently selected from one of the following: unsubstituted or substituted naphthalene rings and substituted or unsubstituted phenanthrene rings, and the rings A1, A2, and A3 are not simultaneously selected from the unsubstituted naphthalene rings.

[0009] R1 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic-heterocyclic.

[0010] The number m is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0011] The ring B is selected from one of substituted or unsubstituted benzene rings and substituted or unsubstituted azabenzene rings;

[0012] The Ar1, Ar2 and They are not the same, at least one is selected from the structure shown in Formula A, and the remaining ones are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0013]

[0014] The Y is independently selected from N or CR2, and the number of N is 1 or 2;

[0015] The R2 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring fused cycloyl group, and substituted or unsubstituted C3-C20 alicyclic and heterocyclic group;

[0016] The rings E1, E2, and E3 are independently selected from one of the following: unsubstituted or unsubstituted benzene rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted azabenzene rings, substituted or unsubstituted azanaphthyl rings, substituted or unsubstituted azaphenanthyl rings, substituted or unsubstituted cyclopentadiene rings, and substituted or unsubstituted azacyclopentadiene rings.

[0017] 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, fused cycloalcoholic group of substituted or unsubstituted divalent C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted divalent C3-C20 alicyclic and C2-C30 heteroarylene ring.

[0018] The present invention also provides an organic electroluminescent device, comprising a cathode, an organic functional layer, and an anode, wherein the organic functional layer contains the oxazole derivative of the present invention described above.

[0019] Beneficial effects: The oxazole derivative of Formula 1 of this invention has good electron mobility, which can effectively promote the balance of hole and electron transport. At the same time, the oxazole derivative has a deep HOMO energy level, thus having good hole blocking ability, which can effectively block holes within the light-emitting layer and increase the recombination probability of holes and electrons. When applied to the hole blocking layer or electron transport layer of organic electroluminescent devices, it can effectively reduce the driving voltage of the device, increase the luminous efficiency, and extend the service life. In addition, when the oxazole derivative of Formula 1 of this invention is used as the main material in organic electroluminescent devices, the devices also exhibit excellent performance, making it an excellent organic electroluminescent material. Detailed Implementation

[0020] 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.

[0021] 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.

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

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

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

[0025] In this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0026] In this invention, "two adjacent groups joining together to form a ring" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining adjacent groups with each other and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. An example is shown below:

[0027]

[0028] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, fluorene, furan, thiophene, carbazole, etc., but are not limited to these.

[0029] The alkyl group referred to in this invention is a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. The alkyl group has 1 to 20 carbon atoms, preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 6. Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl (including isomers), hexyl (including isomers), heptyl (including isomers), octyl (including isomers), nonyl (including isomers), decyl (including isomers), undecyl (including isomers), dodecyl (including isomers), etc., but are not limited thereto; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl (including isomers); more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and even more preferably methyl or tert-butyl.

[0030] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group has a carbon number of C3 to C20, preferably C3 to C15, more preferably C3 to C10, and even more preferably C3 to C6. Examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, ferricyl, and isocamphenyl; cyclopentyl, cyclohexyl, adamantyl, and norbornel are preferred.

[0031] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. The aryl group has 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 20, and even more preferably 6 to 12. Examples of aryl groups include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzanthracene, phenanthryl, benzophenanthryl, phenatenyl, styrene, pentylene, pyrene, etc. Benzyl, benzo[ The compounds may be phenyl, biphenyl, terphenyl, or naphthyl, but are not limited thereto; preferably phenyl, biphenyl, or naphthyl, more preferably phenyl, biphenyl, or naphthyl, and even more preferably phenyl.

[0032] 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 heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The number of carbon atoms in the heteroaryl group is C2 to C30, more preferably C2 to C25, further preferably C3 to C20, and even more preferably C2 to C12. Examples of heteroaryl groups include pyrroleyl, pyrazolyl, imidazolyl, triazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pteridinyl, phenanthrolinel, benzoquinolinyl, benzoisoquinolinyl, indoleyl, isoindoleyl, benzimidazolyl, naphthiazoleyl, phenanthroimidazolyl, anthraquinimazolyl, tribenzimidazolyl, pyridinimidazolyl, and pyrimidinimidazolyl. The compounds may be pyridyl, triazinzimidazolyl, quinolinzimidazolyl, isoquinolinzimidazolyl, quinoxalolinzimidazolyl, quinoxalolinzimidazolyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, carbazoleyl, etc., but are not limited to these; preferably pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalolinyl, quinoxalolinyl, phenanthrolinel, or indoleyl.

[0033] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by the fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. The fused alicyclic and aromatic ring groups have a carbon number of C7 to C30, preferably C7 to C25, more preferably C7 to C18, and even more preferably C7 to C13. Examples of fused alicyclic and aromatic ring groups include, but are not limited to, benzocyclopropane, benzocyclobutane, dihydroindenyl, tetrahydronaphthyl, benzocycloheptane, benzocyclobutenyl, indenyl, dihydronaphthyl, and benzocycloheptenyl.

[0034] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. The fused cyclic group of alicyclic and heteroaromatic rings has a carbon number of C5 to C30, preferably C5 to C25, more preferably C5 to C18, and even more preferably C5 to C12. Examples of fused cyclic groups of alicyclic and aromatic rings include, but are not limited to, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidinylcyclopentyl, pyrimidinylcyclohexyl, pyrimidinylbenzocycloheptyl, pyrimidinylcyclopentenyl, and pyrimidinylcyclohexenyl.

[0035] The alicyclic compounds described in this invention include cycloalkyl, cycloalkenyl, and cycloalkynyl compounds, etc., wherein the number of carbon atoms in the alicyclic compound is C3 to C20, more preferably C3 to C15, further preferably C3 to C10, and even more preferably C3 to C6. Examples of the alicyclic compounds include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto.

[0036] The alicyclic group described in this invention refers to a divalent group formed by removing one hydrogen atom from an alicyclic hydrocarbon molecule. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The alicyclic group has a carbon number of C2 to C20, preferably C2 to C15, more preferably C2 to C10, and even more preferably C2 to C6. Examples of the alicyclic group include furanyl, tetrahydrofuranyl, thiophenyl, tetrahydrothiophenyl, etc., but are not limited thereto.

[0037] The aryl group mentioned in this invention refers to the collective term for the divalent groups remaining after removing a hydrogen atom from the aromatic carbon of the aforementioned aryl molecule.

[0038] The heteroaryl group mentioned in this invention refers to the collective term for the divalent groups remaining after removing a hydrogen atom from the aromatic carbon of the aforementioned heteroaryl molecule.

[0039] The divalent alicyclic and aromatic fused cyclic groups mentioned in this invention refer to the general term for the groups obtained by removing a hydrogen atom from the aromatic carbon atom of the aforementioned alicyclic and aromatic fused cyclic group molecules.

[0040] The fused cyclic groups of divalent alicyclic and heteroaromatic rings mentioned in this invention refer to the general term for the groups obtained by removing a hydrogen atom from the aromatic carbon of the aforementioned fused cyclic group molecules of alicyclic and heteroaromatic rings.

[0041] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" include, but are not limited to, deuterium, cyano, halogen, nitro, silyl, alkoxy, aryloxy, heterocyclic, alkyl, cycloalkyl, aryl, heteroaryl, fused alicyclic and aromatic rings, fused alicyclic and heteroaryl rings, etc. Preferred groups include: deuterium, cyano, halogen, methyl, ethyl, propyl (including isomers), butyl (including isomers), pentyl (including isomers), hexyl (including isomers), heptyl (including isomers), octyl (including isomers), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, fronyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. Substituents include benzo[a]yl, fluoranyl, benzo[a]cyclopropane, benzo[a]cyclobutane, dihydroindyl, tetrahydronaphthyl, benzo[a]cycloheptyl, benzo[a]cyclooctyl, benzo[a]cyclobutenyl, indyl, dihydronaphthyl, fluorenyl, spirodifluorenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, phenanthrolinel, oxazolyl, benzo[a]oxazolyl, thiazolyl, benzo[a]thiazolyl, imidazolyl, benzo[a]imidazolyl, benzo[a]furanyl, dibenzofuranyl, benzo[a]thiophenyl, dibenzo[a]thiophenyl, indolyl, carbazoleyl, etc. The above substituents can be substituted or unsubstituted, and two adjacent substituents can be linked together to form a substituted or unsubstituted ring.

[0042] This invention provides an oxazole derivative, represented by the following formula 1.

[0043]

[0044] Wherein, X is selected from O, S or N(R) a ); The R a It is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic-heterocyclic group;

[0045] The rings A1, A2, and A3 are independently selected from one of the following: unsubstituted or substituted naphthalene rings and substituted or unsubstituted phenanthrene rings, and the rings A1, A2, and A3 are not simultaneously selected from the unsubstituted naphthalene rings.

[0046] R1 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic-heterocyclic.

[0047] The number m is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0048] The ring B is selected from one of substituted or unsubstituted benzene rings and substituted or unsubstituted azabenzene rings;

[0049] The Ar1, Ar2 and They are not identical; at least one is selected from the structure shown in Formula A, and the remaining independent ones are selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cyclic, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring fused cyclic.

[0050]

[0051] The Y is independently selected from N or CR2, and the number of N is 1 or 2;

[0052] The R2 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring fused cycloyl group, and substituted or unsubstituted C3-C20 alicyclic and heterocyclic group;

[0053] The rings E1, E2, and E3 are independently selected from one of the following: unsubstituted or unsubstituted benzene rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted azabenzene rings, substituted or unsubstituted azanaphthyl rings, substituted or unsubstituted azaphenanthyl rings, substituted or unsubstituted cyclopentadiene rings, and substituted or unsubstituted azacyclopentadiene rings.

[0054] 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, fused cycloalcoholic group of substituted or unsubstituted divalent C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted divalent C3-C20 alicyclic and C2-C30 heteroarylene ring.

[0055] Preferably, the Choose from one of the structures shown below.

[0056]

[0057] R1 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic-heterocyclic.

[0058] The m1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m2 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0059] Preferably, the Choose from one of the structures shown below.

[0060]

[0061] R1 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted of the following groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phenanthrolinel, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, benzocyclopropane, benzocyclobutane, dihydroindyl, tetrahydronaphthyl;

[0062] The m1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m2 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0063] Preferably, the Choose from one of the structures shown below.

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] Preferably, the ring B is selected from one of the following groups:

[0070]

[0071] The R3 is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, or substituted or unsubstituted C3-C20 alicyclic group;

[0072] The n1 is selected from 1, 2 or 3; the n2 is selected from 1 or 2.

[0073] Preferably, the ring B is selected from one of the following groups:

[0074]

[0075] The R3 is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted norbornel.

[0076] The n1 is selected from 1, 2 or 3; the n2 is selected from 1 or 2.

[0077] Preferably, the ring B is selected from one of the following groups:

[0078]

[0079]

[0080] Preferably, formula A is selected from one of the following groups:

[0081]

[0082] The R2 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring fused cycloyl group, and substituted or unsubstituted C3-C20 alicyclic and heterocyclic group;

[0083] The x1 is selected from 1, 2, 3, or 4; the x2 is selected from 1, 2, or 3; the x3 is selected from 1, 2, 3, 4, 5, or 6; the x4 is selected from 1, 2, 3, 4, or 5; the x5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the x6 is selected from 1, 2, 3, 4, 5, 6, or 7; and the x7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0084] Preferably, at least one of Ar1 and Ar2 is selected from formula A, and the remainder is selected from one of the following groups.

[0085]

[0086] The R x R y Independently selected from one of the following: substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, and substituted or unsubstituted C6-C30 aryl groups, or two R groups. y They can connect to form substituted or unsubstituted rings; or R x R y This is a connection key, used to connect to either L1 or L2;

[0087] The R4 is independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl, or substituted or unsubstituted C3-C20 alicyclic-heterocyclic group, or two adjacent R4s can be connected to each other to form a substituted or unsubstituted ring;

[0088] The y1 is selected from 1, 2, 3, 4 or 5; the y2 is selected from 1, 2, 3, 4, 5, 6 or 7; the y3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the y4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the y5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8.

[0089] Preferably, at least one of Ar1 and Ar2 is selected from formula A, and the remainder is selected from one of the following groups.

[0090]

[0091]

[0092] The above-mentioned groups may be substituted or unsubstituted by one or more of the following groups selected from deuterium, cyano, halogen, deuterium-substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclohexyl, adamantyl, norbornel, camphenyl, etc. In the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0093] Preferably, L, L1, and L2 are independently selected from single bonds or one of the following groups:

[0094]

[0095] The R5 is independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and substituted or unsubstituted C3-C20 alicyclic group;

[0096] The z1 is selected from 1, 2, 3 or 4; the z2 is selected from 1, 2, 3, 4, 5 or 6; the z3 is selected from 1, 2 or 3; the z4 is selected from 1 or 2; the z5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the z6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0097] Preferably, Formula 1 is selected from at least one of the following structures.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] The above lists some specific chemical structures of the oxazole derivatives described in Formula 1 of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents as defined above should be included.

[0118] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an organic functional layer, and an anode, wherein the organic functional layer contains the oxazole derivative described in the present invention.

[0119] Preferably, the organic functional layer includes at least one of an electron transport region and a light-emitting layer, wherein the electron transport region and the light-emitting layer contain the oxazole derivative described in this invention.

[0120] Preferably, the electron transport region includes an electron transport layer containing the oxazole derivative described in this invention.

[0121] Preferably, the electron transport region includes a hole blocking layer containing the oxazole derivative described in this invention.

[0122] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, capping layer, etc. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, or light extraction properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0123] 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:

[0124] substrate

[0125] The substrate is used as a support for organic electroluminescent devices, and can be made of materials such as glass, quartz, or plastic. Alternatively, a flexible substrate can also be used. A flexible substrate is a substrate that can be bent (flexible), such as a plastic substrate containing polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride.

[0126] anode

[0127] The preferred anode material is a metal, alloy, conductive compound, or mixture thereof with a high work function (e.g., above 4.0 eV). Examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other materials that can be used include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of these metals (e.g., titanium nitride).

[0128] Hole injection layer

[0129] A hole injection layer is a layer containing materials with high hole injection performance (hole-injectable materials). Examples of hole-injectable materials include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. Low-molecular-weight organic compounds such as N,N'-bis[4-di(m-tolyl)aminophenyl]-N,N'-diphenylbenzidine (DNTPD), 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), copper phthalocyanine (CuPC), titanium phthalocyanine (TiOPC), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), and poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[0130] Hole transport layer

[0131] Hole transport materials need to possess high hole mobility and good stability to facilitate hole transport. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used as hole transport materials. For example: N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3,5-tris(9-carbazolyl)benzene (TCB). 4,4',4”-Tris(carbazole-9-yl)triphenylamine (TCTA), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4”-Tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), polyvinylcarbazole (PVC), etc. The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[0132] Electron blocking layer

[0133] Electron blocking materials need to possess both good hole transport and electron blocking capabilities to effectively transport holes and restrict electrons. Electron blocking layers can utilize aromatic amine derivatives, carbazole derivatives, etc. Examples include: N,N-bis([1,1'-biphenyl]-4-yl)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, N-(4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, and N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), etc.

[0134] Emissive layer

[0135] The light-emitting layer comprises a host material and a dopant material. The light-emitting material can be a red light-emitting material, a green light-emitting material, a blue light-emitting material, or a combination thereof. The doping ratio of the host material and the dopant material can vary depending on the material used. Typically, the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0136] Doped material of the light-emitting layer

[0137] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used as blue luminescent materials for the luminescent layer. Examples include: bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bis(trifluoromethyl)phenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac). Iridium complexes can also be used as green luminescent materials for the luminescent layer. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetone (Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetone (Ir(pbi)2(acac)), and bis(benzoquinoline)iridium(III)acetylacetone (Ir(bzq)2(acac)). Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used as red luminescent materials for the luminescent layer. Examples include: [2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (PtOEP), etc.

[0138] The main material of the light-emitting layer

[0139] The preferred host material is one with a lower lowest unoccupied orbital (LUMO) energy level and a lower highest occupied orbital (HOMO) energy level than the doped material. Suitable host materials include aluminum complexes, beryllium complexes, zinc complexes, oxadiazole derivatives, benzimidazole derivatives, phenanthrene-rhein derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, triarylamine derivatives, and fused polycyclic aromatic amine derivatives. For example: tris(8-hydroxyquinoline)aluminum(III) (abbreviated: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (Almq3), bis(10-hydroxybenzoquinoline)beryllium(II) (BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), bis(8-hydroxyquinoline)zinc(II) (Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (ZnBTZ), 2-(4-biphenyl)-5- (4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]phenyl (OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 2,2',2”-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (TPBI), phenanthroline (BPhen), 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4- [10-Phenylacetyl-9-anthrayl]phenyl-9H-carbazole (DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), 9,10-bis(2-naphthyl)anthracene (DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 9,9'-bianthracite (BANT), 9,9'-(indox-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(indox-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3”-(benzyl-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenyl Anthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl, N,N-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (PCAPBA), N-(9,Examples of biphenyls used as the main body include 10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), with two or more main materials permitted.

[0140] Cavity barrier

[0141] Hole-blocking materials function by trapping holes within the light-emitting layer, thereby increasing the binding rate of electrons and holes. Hole-blocking materials can utilize metal complexes, heteroaromatic compounds, etc. Examples 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), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc.

[0142] Electron transport layer

[0143] An electron transport layer is a layer containing materials with high electron transport performance (electron transport materials). Electron transport layers can utilize metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and polymeric compounds. For example: tris(8-hydroxyquinoline)aluminum(III) (Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzoquinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), bis(8-hydroxyquinoline)zinc(II) (Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (ZnBTZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]phenyl (OXD) -7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (p-EtTAZ), phenanthroline (BPhen), copper bath (BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (BzOs), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (PF-BPy), etc., the above materials have 10 -6 cm 2 Materials with electron mobility above / Vs.

[0144] Electron injection layer

[0145] The electron injection layer is a layer containing materials with high electron injection performance. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used for the electron injection layer. Alternatively, materials containing alkali metals, alkaline earth metals, or their compounds can also be used.

[0146] cathode

[0147] The cathode preferably utilizes metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV). Examples include lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), ytterbium (Yb), europium (Eu), and their alloys (e.g., MgAg, AlLi).

[0148] The preparation method of each thin film layer of the organic electroluminescent device of the present invention is not particularly limited, and can be formed by conventionally known methods such as vapor deposition and coating. For example, it can be formed using known methods such as vacuum vapor deposition, molecular beam evaporation (MBE), or coating methods using solutions of compounds forming the layers, dip coating, spin coating, casting, rod coating, and roll coating. The film thickness of each layer is not particularly limited. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated; conversely, if it is too thick, a high driving voltage is required, resulting in decreased efficiency. Preferably, it is 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[0149] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablets, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0150] Synthesis Examples

[0151] There are no particular limitations on the preparation method of the oxazole derivatives shown in Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reactions, etc. The oxazole derivatives shown in Formula 1 of this invention can be prepared, for example, using the synthetic route shown below.

[0152] (1)

[0153] (2)

[0154] The X a For example, X is a halogen. a Independently selected from Cl, Br, I; the X b for

[0155] 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.

[0156] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0157] Synthesis Example 1: Synthesis of Compound 11

[0158]

[0159] Preparation of intermediate I-11:

[0160] Under nitrogen protection, a-11 (38.20 g, 120.00 mmol), b-11 (24.61 g, 120.00 mmol), Na₂CO₃ (19.08 g, 180.00 mmol), Pd(PPh₃)₄ (1.39 g, 1.20 mmol), and 480 mL of 1,4-dioxane were added to a reaction flask, and the mixture was reacted under reflux for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / petroleum ether at a ratio of 4:1 to give intermediate I-11 (25.55 g, yield 79%); HPLC purity ≥99.70%. Mass spectrometry m / z: 267.9415 (theoretical value: 267.9403).

[0161] Preparation of intermediate II-11:

[0162] Under nitrogen protection, I-11 (21.56 g, 80.00 mmol), b1-11 (24.34 g, 80.00 mmol), Na2CO3 (12.72 g, 120.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and 320 mL of 1,4-dioxane were added to a reaction flask, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / petroleum ether at a ratio of 4:1 to give intermediate II-11 (22.30 g, yield 76%); HPLC purity ≥99.73%. Mass spectrometry m / z: 366.0915 (theoretical value: 366.0924).

[0163] Preparation of intermediate II'-11:

[0164] Under nitrogen protection, II-11 (18.34 g, 50.00 mmol), pinacol diborate (13.97 g, 55.00 mmol), K₂CO₃ (13.82 g, 100.00 mmol), Pd(dppf)Cl₂ (0.44 g, 0.60 mmol), and 450 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake. The cake was recrystallized from toluene / n-hexane at a ratio of 5:1 to give intermediate II'-11 (17.19 g, yield 75%); HPLC purity ≥99.80%. Mass spectrometry m / z: 458.2180 (theoretical value: 458.2166).

[0165] Preparation of compound 11:

[0166] Under nitrogen protection, 13.75 g (30.00 mmol), c-11 (9.79 g (30.00 mmol), Na₂CO₃ (4.77 g (45.00 mmol), Pd(OAc)₂ (0.07 g (0.30 mmol), P(t-Bu)₃ (0.06 g (0.30 mmol), and 120 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 11 (12.48 g, yield 72%); HPLC purity ≥99.91%. Mass spectrometry m / z: 577.2164 (theoretical value: 577.2154). Theoretical elemental content (%) C 41 H 27 N3O: C, 85.25; H, 4.71; N, 7.27. Measured elemental content (%): C, 85.29; H, 4.68; N, 7.24.

[0167] Synthesis Example 2: Synthesis of Compound 15

[0168]

[0169] Preparation of intermediate I-15:

[0170] Under nitrogen protection, a-15 (21.71 g, 80.00 mmol), b-15 (32.81 g, 160.00 mmol), Pd(PPh3)4 (1.85 g, 1.60 mmol), K2CO3 (33.17 g, 240.00 mmol), 500 mL toluene, 250 mL ethanol, and 250 mL water were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene / petroleum ether at a ratio of 5:1 to obtain intermediate I-15 (16.49 g, yield 77%); HPLC purity ≥99.71%. Mass spectrometry m / z: 267.0571 (theoretical value: 267.0563).

[0171] Preparation of intermediate I'-15:

[0172] Under nitrogen protection, I-15 (13.39 g, 50.00 mmol), pinacol diborate (13.97 g, 55.00 mmol), CH3COOK (9.81 g, 100.00 mmol), Pd(dppf)Cl2 (0.44 g, 0.60 mmol), and 450 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake. The cake was recrystallized from toluene / n-hexane at a ratio of 5:1 to give intermediate I'-15 (14.01 g, yield 78%); HPLC purity ≥99.75%. Mass spectrometry m / z: 359.1822 (theoretical value: 359.1805).

[0173] Preparation of compound 15:

[0174] Under nitrogen protection, I'-15 (10.78 g, 30.00 mmol), c-15 (11.23 g, 30.00 mmol), Pd(PPh3)4 (0.35 g, 0.30 mmol), K2CO3 (6.22 g, 45.00 mmol), 100 mL toluene, 50 mL ethanol, and 50 mL water were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to give compound 15 (11.85 g, yield 75%); HPLC purity ≥99.96%. Mass spectrometry m / z: 526.1780 (theoretical value: 526.1794). Theoretical elemental content (%) C 36 H 22N4O: C, 82.11; H, 4.21; N, 10.64. Measured elemental content (%): C, 82.08; H, 4.25; N, 10.61.

[0175] Synthesis Example 3: Synthesis of Compound 18

[0176]

[0177] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-18, and c-18, respectively, to obtain compound 18 (14.84 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 677.2450 (theoretical value: 677.2467). Theoretical elemental content (%) C 49 H 31 N3O: C, 86.83; H, 4.61; N, 6.20. Measured elemental content (%): C, 86.87; H, 4.58; N, 6.16.

[0178] Synthesis Example 4: Synthesis of Compound 27

[0179]

[0180] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-27, and c-27, respectively, to obtain compound 27 (13.33 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 625.2143 (theoretical value: 625.2154). Theoretical elemental content (%) C 45 H 27 N3O: C, 86.38; H, 4.35; N, 6.72. Measured elemental content (%): C, 86.41; H, 4.39; N, 6.69.

[0181] Synthesis Example 5: Synthesis of Compound 29

[0182]

[0183] Following the same preparation method as compound 15 in Synthesis Example 2, a-15 and b-15 were replaced with equimolar amounts of a-29 and b-29, respectively, to obtain compound 29 (15.93 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 780.2981 (theoretical value: 780.2968). Theoretical elemental content (%) C 57 H 32D3N3O: C, 87.67; H, 4.90; N, 5.38. Measured elemental content (%): C, 87.71; H, 4.88; N, 5.41.

[0184] Synthesis Example 6: Synthesis of Compound 34

[0185]

[0186] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-34, b-34, and c-34, respectively, to obtain compound 34 (15.52 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 795.2695 (theoretical value: 795.2686). Theoretical elemental content (%) C 57 H 34 FN3O: C, 86.02; H, 4.31; N, 5.28. Measured elemental content (%): C, 86.05; H, 4.28; N, 5.30.

[0187] Synthesis Example 7: Synthesis of Compound 39

[0188]

[0189] Following the same preparation method as compound 15 in Synthesis Example 2, a-15 and b-15 were replaced with equimolar amounts of a-18 and b-39, respectively, to obtain compound 39 (15.07 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 727.2362 (theoretical value: 727.2372). Theoretical elemental content (%) C 51 H 29 N5O: C, 84.16; H, 4.02; N, 9.62. Measured elemental content (%): C, 84.20; H, 4.04; N, 9.59.

[0190] Synthesis Example 8: Synthesis of Compound 43

[0191]

[0192] Preparation of intermediate I-43:

[0193] Under nitrogen protection, a-18 (43.26 g, 160.00 mmol), b-43 (65.62 g, 320.00 mmol), Pd(PPh3)4 (3.70 g, 3.20 mmol), K2CO3 (66.34 g, 480.00 mmol), 1000 mL toluene, 500 mL ethanol, and 500 mL water were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 15 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene / petroleum ether at a ratio of 5:1 to obtain intermediate I-43 (33.29 g, yield 78%); HPLC purity ≥99.77%. Mass spectrometry m / z: 266.0628 (theoretical value: 266.0611).

[0194] Preparation of intermediate I'-43:

[0195] Under nitrogen protection, I-43 (29.34 g, 110.00 mmol), pinacol diborate (30.47 g, 120.00 mmol), CH3COOK (21.59 g, 220.00 mmol), Pd(dppf)Cl2 (0.95 g, 1.30 mmol), and 900 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake. The cake was recrystallized from toluene / n-hexane at a ratio of 5:1 to give intermediate I'-43 (31.53 g, yield 80%); HPLC purity ≥99.69%. Mass spectrometry m / z: 358.1862 (theoretical value: 358.1853).

[0196] Preparation of intermediate II-43:

[0197] Under nitrogen protection, I'-43 (28.66 g, 80.00 mmol), d-43 (15.64 g, 80.00 mmol), Na2CO3 (12.72 g, 120.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and 320 mL of 1,4-dioxane were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / petroleum ether at a ratio of 5:1 to give intermediate II-43 (20.81 g, yield 75%); HPLC purity ≥99.79%. Mass spectrometry m / z: 346.1160 (theoretical value: 346.1175).

[0198] Preparation of intermediate II'-43:

[0199] Under nitrogen protection, II-43 (17.34 g, 50.00 mmol), pinacol diborate (13.97 g, 55.00 mmol), K₂CO₃ (13.82 g, 100.00 mmol), Pd(dppf)Cl₂ (0.44 g, 0.60 mmol), and 450 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 7.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake. The cake was recrystallized from toluene / n-hexane at a ratio of 6:1 to give intermediate II'-43 (16.88 g, yield 77%); HPLC purity ≥99.82%. Mass spectrometry m / z: 438.2407 (theoretical value: 438.2417).

[0200] Preparation of compound 43:

[0201] Under nitrogen protection, II'-43 (13.15 g, 30.00 mmol), c-15 (11.23 g, 30.00 mmol), Pd(PPh3)4 (0.35 g, 0.30 mmol), K2CO3 (6.22 g, 45.00 mmol), 100 mL toluene, 50 mL ethanol, and 50 mL water were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to give compound 43 (13.45 g, yield 74%); HPLC purity ≥99.95%. Mass spectrometry m / z: 605.2421 (theoretical value: 605.2405). Theoretical elemental content (%) C 43 H 23 D4N3O: C, 85.26; H, 5.16; N, 6.94. Measured elemental content (%): C, 85.30; H, 5.19; N, 6.91.

[0202] Synthesis Example 9: Synthesis of Compound 51

[0203]

[0204] Following the same preparation method as compound 43 in Example 8, b-43 and d-43 were replaced with equimolar amounts of b-51 and d-51, respectively, to obtain compound 51 (15.84 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 743.2677 (theoretical value: 743.2685). Theoretical elemental content (%) C 52 H 33 N5O: C, 83.96; H, 4.47; N, 9.41. Measured elemental content (%): C, 83.92; H, 4.50; N, 9.37.

[0205] Synthesis Example 10: Synthesis of Compound 57

[0206]

[0207] Following the same preparation method as compound 11 in Synthesis Example 1, a-11, b-11, b1-11, and c-11 were replaced with equimolar amounts of a-57, b-57, b1-57, and c-15, respectively, to obtain compound 57 (14.12 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 653.2231 (theoretical value: 653.2216). Theoretical elemental content (%) C 45 H 27 N5O: C, 82.68; H, 4.16; N, 10.71. Measured elemental content (%): C, 82.71; H, 4.20; N, 10.67.

[0208] Synthesis Example 11: Synthesis of Compound 69

[0209]

[0210] Following the same preparation method as compound 11 in Example 1, b-11, b1-11, and c-11 were replaced with equimolar amounts of b-69, b1-69, and c-69, respectively, to obtain compound 69 (13.06 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 630.2457 (theoretical value: 630.2468). Theoretical elemental content (%) C 45 H 22 D5N3O: C, 85.69; H, 5.11; N, 6.66. Measured elemental content (%): C, 85.71; H, 5.08; N, 6.70.

[0211] Synthesis Example 12: Synthesis of Compound 70

[0212]

[0213] Following the same preparation method as compound 11 in Example 1, a-11, b-11, b1-11, and c-11 were replaced with equimolar amounts of a-70, b-70, b1-70, and c-18, respectively, to obtain compound 70 (14.02 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 667.2022 (theoretical value: 667.2008). Theoretical elemental content (%) C 45 H 25 N5O2: C, 80.95; H, 3.77; N, 10.49. Measured elemental content (%): C, 80.98; H, 3.73; N, 10.51.

[0214] Synthesis Example 13: Synthesis of Compound 72

[0215]

[0216] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-43, and c-72, respectively, to obtain compound 72 (11.83 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 525.1833 (theoretical value: 525.1841). Theoretical elemental content (%) C 37 H 23 N3O: C, 84.55; H, 4.41; N, 7.99. Measured elemental content (%): C, 84.59; H, 4.38; N, 7.96.

[0217] Synthesis Example 14: Synthesis of Compound 89

[0218]

[0219] Following the same preparation method as compound 43 in Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-89, d-89, and c-89, respectively, to obtain compound 89 (14.36 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 703.2359 (theoretical value: 703.2372). Theoretical elemental content (%) C 49 H 29 N5O: C, 83.62; H, 4.15; N, 9.95. Measured elemental content (%): C, 83.58; H, 4.19; N, 9.98.

[0220] Synthesis Example 15: Synthesis of Compound 102

[0221]

[0222] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-102, and c-102, respectively, to obtain compound 102 (13.52 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 625.2166 (theoretical value: 625.2154). Theoretical elemental content (%) C 45 H 27 N3O: C, 86.38; H, 4.35; N, 6.72. Measured elemental content (%): C, 86.41; H, 4.32; N, 6.75.

[0223] Synthesis Example 16: Synthesis of Compound 109

[0224]

[0225] Following the same preparation method as compound 43 in Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-109, d-109, and c-109, respectively, to obtain compound 109 (12.68 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 603.2050 (theoretical value: 603.2059). Theoretical elemental content (%) C 41 H 25 N5O: C, 81.57; H, 4.17; N, 11.60. Measured elemental content (%): C, 81.60; H, 4.21; N, 11.56.

[0226] Synthesis Example 17: Synthesis of Compound 125

[0227]

[0228] Following the same preparation method as compound 15 in Synthesis Example 2, a-15 and c-15 were replaced with equimolar amounts of a-125 and c-125, respectively, to obtain compound 125 (11.73 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 528.1681 (theoretical value: 528.1699). Theoretical elemental content (%) C 34 H 20 N6O: C, 77.26; H, 3.81; N, 15.90. Measured elemental content (%): C, 77.28; H, 3.78; N, 15.86.

[0229] Synthesis Example 18: Synthesis of Compound 141

[0230]

[0231] Following the same preparation method as compound 43 in Synthesis Example 8, a-18, d-43, and c-15 were replaced with equimolar amounts of a-15, d-141, and c-125, respectively, to obtain compound 141 (14.29 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 670.1992 (theoretical value: 670.1980). Theoretical elemental content (%) C 43 H 25 F3N4O: C, 77.01; H, 3.76; N, 8.35. Measured elemental content (%): C, 77.05; H, 3.72; N, 8.32.

[0232] Synthesis Example 19: Synthesis of Compound 144

[0233]

[0234] Following the same preparation method as compound 43 in Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-144, d-144, and c-125, respectively, to obtain compound 144 (15.40 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 754.2750 (theoretical value: 754.2733). Theoretical elemental content (%) C 54 H 34 N4O: C, 85.92; H, 4.54; N, 7.42. Measured elemental content (%): C, 85.89; H, 4.58; N, 7.38.

[0235] Synthesis Example 20: Synthesis of Compound 147

[0236]

[0237] Following the same preparation method as compound 11 in Example 1, a-11, b-11, b1-11, and c-11 were replaced with equimolar amounts of a-147, b-15, b1-147, and c-147, respectively, to obtain compound 147 (12.54 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 580.2301 (theoretical value: 580.2311). Theoretical elemental content (%) C 41 H 20 D5N3O: C, 84.80; H, 5.21; N, 7.24. Measured elemental content (%): C, 84.78; H, 5.17; N, 7.28.

[0238] Synthesis Example 21: Synthesis of Compound 162

[0239]

[0240] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-162, and c-162, respectively, to obtain compound 162 (14.57 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 703.2359 (theoretical value: 703.2372). Theoretical elemental content (%) C 49 H 29 N5O: C, 83.62; H, 4.15; N, 9.95. Measured elemental content (%): C, 83.59; H, 4.17; N, 9.99.

[0241] Synthesis Example 22: Synthesis of Compound 179

[0242]

[0243] Following the same preparation method as compound 15 in Synthesis Example 2, a-15 and c-15 were replaced with equimolar amounts of a-179 and c-179, respectively, to obtain compound 179 (11.56 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 550.1778 (theoretical value: 550.1794). Theoretical elemental content (%) C 38 H 22 N4O: C, 82.89; H, 4.03; N, 10.18. Measured elemental content (%): C, 82.93; H, 4.07; N, 10.20.

[0244] Synthesis Example 23: Synthesis of Compound 194

[0245]

[0246] Following the same preparation method as compound 43 in Example 8, a-18, b-43, d-43, and c-15 were replaced with equimolar amounts of a-125, b-194, d-194, and c-194, respectively, to obtain compound 194 (15.70 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 780.2648 (theoretical value: 780.2638). Theoretical elemental content (%) C 54 H 32 N6O: C, 83.06; H, 4.13; N, 10.76. Measured elemental content (%): C, 83.10; H, 4.10; N, 10.81.

[0247] Synthesis Example 24: Synthesis of Compound 203

[0248]

[0249] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-203, and c-203, respectively, to obtain compound 203 (15.07 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 727.2638 (theoretical value: 727.2624). Theoretical elemental content (%) C 53 H 33 N3O: C, 87.46; H, 4.57; N, 5.77. Measured elemental content (%): C, 87.50; H, 4.61; N, 5.75.

[0250] Synthesis Example 25: Synthesis of Compound 211

[0251]

[0252] Following the same preparation method as compound 11 in Synthesis Example 1, a-11, b-11, b1-11, and c-11 were replaced with equimolar amounts of a-57, b-211, b1-211, and c-211, respectively, to obtain compound 211 (14.74 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 701.3140 (theoretical value: 701.3155). Theoretical elemental content (%) C 48 H 39 N5O: C, 82.14; H, 5.60; N, 9.98. Measured elemental content (%): C, 82.18; H, 5.58; N, 9.95.

[0253] Synthesis Example 26: Synthesis of Compound 226

[0254]

[0255] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-226, and c-226, respectively, to obtain compound 226 (14.36 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 703.2364 (theoretical value: 703.2372). Theoretical elemental content (%) C 49 H 29 N5O: C, 83.62; H, 4.15; N, 9.95. Measured elemental content (%): C, 83.59; H, 4.19; N, 9.93.

[0256] Synthesis Example 27: Synthesis of Compound 286

[0257]

[0258] Following the same preparation method as compound 11 in Synthesis Example 1, a-11, b-11, b1-11, and c-11 were replaced with equimolar amounts of a-147, b-286, b1-286, and c-286, respectively, to obtain compound 286 (14.33 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 712.2361 (theoretical value: 712.2345). Theoretical elemental content (%) C 49 H 24 D5N3OS: C, 82.56; H, 4.81; N, 5.89. Measured elemental content (%): C, 82.60; H, 4.78; N, 5.92.

[0259] Synthesis Example 28: Synthesis of Compound 326

[0260]

[0261] Following the same preparation method as compound 43 in Synthesis Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-326, d-326, and c-326, respectively, to obtain compound 326 (14.66 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 751.2633 (theoretical value: 751.2624). Theoretical elemental content (%) C 55 H 33 N3O: C, 87.86; H, 4.42; N, 5.59. Measured elemental content (%): C, 87.90; H, 4.39; N, 5.61.

[0262] Synthesis Example 29: Synthesis of Compound 378

[0263]

[0264] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-378, and c-378, respectively, to obtain compound 378 (14.12 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 653.2851 (theoretical value: 653.2865). Theoretical elemental content (%) C 45 H 39 N3S: C, 82.66; H, 6.01; N, 6.43. Measured elemental content (%): C, 82.62; H, 6.05; N, 6.39.

[0265] Synthesis Example 30: Synthesis of Compound 420

[0266]

[0267] Following the same preparation method as compound 15 in Synthesis Example 2, b-15 and c-15 were replaced with equimolar amounts of b-420 and c-420, respectively, to obtain compound 420 (15.74 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 794.2516 (theoretical value: 794.2504). Theoretical elemental content (%) C 56 H 34 N4S: C, 84.61; H, 4.31; N, 7.05. Measured elemental content (%): C, 84.57; H, 4.29; N, 7.08.

[0268] Synthesis Example 31: Synthesis of Compound 459

[0269]

[0270] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-459, b-459, and c-459, respectively, to obtain compound 459 (15.05 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 783.2716 (theoretical value: 783.2708). Theoretical elemental content (%) C 56 H 37 N3S: C, 85.79; H, 4.76; N, 5.36. Measured elemental content (%): C, 85.82; H, 4.80; N, 5.38.

[0271] Synthesis Example 32: Synthesis of Compound 575

[0272]

[0273] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-575, and c-575, respectively, to obtain compound 575 (14.68 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 752.2931 (theoretical value: 752.2940). Theoretical elemental content (%) C 55 H 36 N4: C, 87.74; H, 4.82; N, 7.44. Measured elemental content (%): C, 87.78; H, 4.79; N, 7.41.

[0274] Synthesis Example 33: Synthesis of Compound 664

[0275]

[0276] Following the same preparation method as compound 43 in Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-664, d-664, and c-664, respectively, to obtain compound 664 (12.52 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 604.2001 (theoretical value: 604.2012). Theoretical elemental content (%) C 40 H 24 N6O: C, 79.45; H, 4.00; N, 13.90. Measured elemental content (%): C, 79.49; H, 4.02; N, 13.86.

[0277] Synthesis Example 34: Synthesis of Compound 665

[0278]

[0279] Following the same preparation method as compound 15 in Synthesis Example 2, a-15 and b-15 were replaced with equimolar amounts of a-18 and b-665, respectively, to obtain compound 665 (12.86 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 603.2040 (theoretical value: 603.2059). Theoretical elemental content (%) C 41 H 25 N5O: C, 81.57; H, 4.17; N, 11.60. Measured elemental content (%): C, 81.60; H, 4.21; N, 11.56.

[0280] Synthesis Example 35: Synthesis of Compound 675

[0281]

[0282] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-675, and c-18, respectively, to obtain compound 675 (15.19 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 755.2698 (theoretical value: 755.2685). Theoretical elemental content (%) C 53 H 33 N5O: C, 84.22; H, 4.40; N, 9.27. Measured elemental content (%): C, 84.18; H, 4.37; N, 9.31.

[0283] Synthesis Example 36: Synthesis of Compound 685

[0284]

[0285] Following the same preparation method as compound 43 in Synthesis Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-685, d-685, and c-685, respectively, to obtain compound 685 (14.27 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 731.2450 (theoretical value: 731.2434). Theoretical elemental content (%) C 49 H 29 N7O: C, 80.42; H, 3.99; N, 13.40. Measured elemental content (%): C, 80.47; H, 3.96; N, 13.36.

[0286] Synthesis Example 37: Synthesis of Compound 687

[0287]

[0288] Following the same preparation method as compound 43 in Synthesis Example 8, b-43, d-43, and c-15 were replaced with equimolar amounts of b-687, d-109, and c-125, respectively, to obtain compound 687 (13.91 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 681.2259 (theoretical value: 681.2277). Theoretical elemental content (%) C 45 H 27 N7O: C, 79.28; H, 3.99; N, 14.38. Measured elemental content (%): C, 79.31; H, 3.97; N, 14.42.

[0289] Synthesis Example 38: Synthesis of Compound 691

[0290]

[0291] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-691, and c-179, respectively, to obtain compound 691 (13.18 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 601.2162 (theoretical value: 601.2154). Theoretical elemental content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured elemental content (%): C, 85.79; H, 4.48; N, 6.94.

[0292] Synthesis Example 39: Synthesis of Compound 734

[0293]

[0294] Following the same preparation method as compound 15 in Synthesis Example 2, a-15, b-15, and c-15 were replaced with equimolar amounts of a-18, b-734, and c-734, respectively, to obtain compound 734 (12.87 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 621.1746 (theoretical value: 621.1736). Theoretical elemental content (%) C 39 H 23 N7S: C, 75.34; H, 3.73; N, 15.77. Measured elemental content (%): C, 75.37; H, 3.69; N, 15.81.

[0295] Synthesis Example 40: Synthesis of Compound 752

[0296]

[0297] Following the same preparation method as compound 11 in Synthesis Example 1, b-11, b1-11, and c-11 were replaced with equimolar amounts of b-752, b1-752, and c-752, respectively, to obtain compound 752 (13.68 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 690.2515 (theoretical value: 690.2532). Theoretical elemental content (%) C 48 H 30 N6: C, 83.46; H, 4.38; N, 12.17. Measured element content (%): C, 83.50; H, 4.41; N, 12.20.

[0298] Fabrication of organic electroluminescent devices

[0299] The molecular formulas of the relevant materials are shown below:

[0300]

[0301] Test Method: A combined IVL test system was constructed using test software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter to test the driving voltage and luminous efficiency of organic electroluminescent devices. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system. The test environment was atmospheric, at room temperature.

[0302] The specific preparation process is as follows:

[0303] Example 1: Fabrication of Organic Electroluminescent Device 1

[0304] First, the ITO glass substrate is rinsed twice in distilled water and ultrasonically washed for 30 minutes. Then, it is rinsed twice more in distilled water and ultrasonically washed for 10 minutes. After the distilled water rinsing, it is ultrasonically washed in sequence with isopropanol, acetone and methanol solvents. Then, it is dried on a hot plate heated to 120°C. The dried substrate is then transferred to a plasma cleaner and washed for 5 minutes before being transferred to an evaporation machine.

[0305] On the ITO anode, material HI-1 was vacuum-deposited as a hole injection layer with a thickness of 10 nm; on the hole injection layer, material HT-1 was vacuum-deposited as a hole transport layer with a thickness of 110 nm; on the hole transport layer, material GH-1:GH-2:GD-1 = 47:47:3 (mass ratio) was vacuum-deposited as a light-emitting layer with a thickness of 30 nm; on the light-emitting layer, material compound 11 was vacuum-deposited as an electron transport layer with a thickness of 30 nm; on the electron transport layer, material LiF was vacuum-deposited as an electron injection layer with a thickness of 1 nm; and on the electron injection layer, material Al was vacuum-deposited as a cathode with a thickness of 120 nm.

[0306] Examples 2-40: Fabrication of Organic Electroluminescent Devices 2-40

[0307] In Example 1, compound 11 in the electron transport layer was replaced with compounds 15, 18, 27, 29, 34, 39, 43, 51, 57, 69, 70, 72, 89, 102, 109, 125, 141, 144, 147, 162, 179, 194, 203, 211, 226, 286, 326, 378, 420, 459, 575, 664, 665, 675, 685, 687, 691, 734, and 752, respectively. The other steps were the same as those for the preparation of organic electroluminescent device 1, resulting in organic electroluminescent devices 2 to 40.

[0308] Comparative Examples 1-2: Fabrication of Comparative Organic Electroluminescent Devices 1-2

[0309] The electron transport compound 11 in Example 1 was replaced with R-1 and R-2 respectively, and the other steps were the same as the preparation method of organic electroluminescent device 1, so as to obtain comparative organic electroluminescent devices 1-2.

[0310] After completing the fabrication of the organic electroluminescent device according to the above steps, the driving voltage, luminous efficiency, and lifetime of the device were measured, and the results are shown in Table 1:

[0311] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0312]

[0313]

[0314] According to Table 1, compared with comparative devices 1-2, the organic electroluminescent device of the present invention has a lower driving voltage, higher luminous efficiency, and longer service life, which indicates that the oxazole derivative of Formula 1 of the present invention is a high-performance electron transport material.

[0315] Example 41: Fabrication of Organic Electroluminescent Device 41

[0316] First, the ITO glass substrate is rinsed twice in distilled water and ultrasonically washed for 30 minutes. Then, it is rinsed twice more in distilled water and ultrasonically washed for 10 minutes. After the distilled water rinsing, it is ultrasonically washed in sequence with isopropanol, acetone and methanol solvents. Then, it is dried on a hot plate heated to 120°C. The dried substrate is then transferred to a plasma cleaner and washed for 5 minutes before being transferred to an evaporation machine.

[0317] On the ITO anode, material HI-1 was vacuum-deposited as a hole injection layer with a thickness of 10 nm; on the hole injection layer, material HT-1 was vacuum-deposited as a hole transport layer with a thickness of 110 nm; on the hole transport layer, material GH-1:GH-2:GD-1 (mass ratio) of 47:47:3 was vacuum-deposited as a light-emitting layer with a thickness of 25 nm; on the light-emitting layer, material compound 11 was vacuum-deposited as a hole blocking layer with a thickness of 8 nm; on the hole blocking layer, material ET-1 was vacuum-deposited as an electron transport layer with a thickness of 25 nm; on the electron transport layer, material LiF was vacuum-deposited as an electron injection layer with a thickness of 1 nm; and on the electron injection layer, material Al was vacuum-deposited as a cathode with a thickness of 120 nm.

[0318] Examples 42-60: Fabrication of Organic Electroluminescent Devices 42-60

[0319] In Example 41, compound 15 in the hole blocking layer was replaced with compounds 18, 27, 29, 43, 69, 70, 72, 102, 109, 125, 144, 162, 203, 226, 378, 420, 675, 687, and 752, respectively. The other steps were the same as those for the preparation of organic electroluminescent device 41, resulting in organic electroluminescent devices 42-60.

[0320] Comparative Examples 3-4: Fabrication of Comparative Organic Electroluminescent Devices 3-4

[0321] By replacing compound 15 in the hole blocking layer of Example 41 with R-1 and R-2 respectively, and following the same steps as the preparation method of organic electroluminescent device 41, comparative organic electroluminescent devices 3-4 were obtained.

[0322] After completing the fabrication of the organic electroluminescent device according to the above steps, the driving voltage, luminous efficiency, and lifetime of the device were measured, and the results are shown in Table 2:

[0323] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0324]

[0325]

[0326] According to Table 2, compared with comparative devices 3-4, the organic electroluminescent device of the present invention has a lower driving voltage, higher luminous efficiency, and longer service life, which indicates that the oxazole derivative of Formula 1 of the present invention has good hole blocking ability.

[0327] Example 61: Fabrication of Organic Electroluminescent Device 61

[0328] On the ITO anode, HI-2 material was vacuum-deposited as a hole injection layer with a thickness of 60 nm; on the hole injection layer, HT-2 material was vacuum-deposited as a hole transport layer with a thickness of 40 nm; on the hole transport layer, compound 15:RH-1:RD-1 = 48:48:4 (mass ratio) was vacuum-deposited as a light-emitting layer with a thickness of 35 nm; on the light-emitting layer, ET-2 material was vacuum-deposited as an electron transport layer with a thickness of 30 nm; on the electron transport layer, LiF material was vacuum-deposited as an electron injection layer with a thickness of 1.1 nm; and on the electron injection layer, Al material was vacuum-deposited as a cathode with a thickness of 150 nm.

[0329] Examples 62-80: Fabrication of Organic Electroluminescent Devices 62-80

[0330] In Example 61, compound 15 in the light-emitting layer was replaced with compounds 18, 27, 29, 43, 69, 70, 72, 102, 109, 125, 144, 162, 203, 226, 378, 420, 675, 687, and 752, respectively. The other steps were the same as those for the preparation of organic electroluminescent device 61, resulting in organic electroluminescent devices 82-100.

[0331] Comparative Examples 5-6: Fabrication of Comparative Organic Electroluminescent Devices 5-6

[0332] By replacing compound 15 in the light-emitting layer of Example 61 with R-1 and R-2 respectively, and following the same steps as the preparation method of organic electroluminescent device 61, comparative organic electroluminescent devices 5-6 were obtained.

[0333] After completing the fabrication of the organic electroluminescent device according to the above steps, the driving voltage, luminous efficiency, and lifetime of the device were measured, and the results are shown in Table 3:

[0334] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0335]

[0336]

[0337] According to Table 3, compared with comparative devices 5-6, the organic electroluminescent device of the present invention has a lower driving voltage, higher luminous efficiency, longer service life, and superior device performance.

[0338] 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 oxazole derivative, characterized in that, It is represented by the following equation 1, Among them, the Choose from one of the structures shown below. R1 is independently selected from hydrogen and deuterium; The m1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; X is selected from O, S, or N(R) a ); The R a Selected from one of the aryl groups of C6 to C12, whether substituted or unsubstituted; The ring B is selected from one of the following groups. ； The R3 is independently selected from one of hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, and substituted or unsubstituted pentyl. The n1 is selected from 1, 2, or 3; the n2 is selected from 1 or 2; At least one of Ar1 and Ar2 is selected from formula A, and the remainder is selected from one of the following groups. The R4 is independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl groups; The y1 is selected from 1, 2, 3, 4 or 5; the y2 is selected from 1, 2, 3, 4, 5, 6 or 7; the y3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; Formula A is selected from one of the following groups. Alternatively, Ar1 and Ar2 may both be selected from one of the following groups: The R2 is independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; The R2' is independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl groups; x1 is selected from 1, 2, 3 or 4; x2 is selected from 1, 2 or 3; x3 is selected from 1, 2, 3, 4, 5 or 6; x4 is selected from 1, 2, 3, 4 or 5; x5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; x6 is selected from 1, 2, 3, 4, 5, 6 or 7. The L is selected from a single bond or one of the following groups: The L1 and L2 are independently selected from single bonds or one of the following groups. The R5 is independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl groups; The z1 is selected from 1, 2, 3 or 4; the z2 is selected from 1, 2, 3, 4, 5 or 6; the z3 is selected from 1, 2 or 3; the z5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the z6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. The substituents represented by "substituted or unsubstituted" are selected from deuterium, methyl, ethyl, propyl, and butyl.

2. The oxazole derivative according to claim 1, characterized in that, The Choose from one of the structures shown below. 。 3. The oxazole derivative according to claim 1, characterized in that, The ring B is selected from one of the following groups. The R3 is independently selected from hydrogen and deuterium.

4. The oxazole derivative according to claim 1, characterized in that, Formula A is selected from one of the following groups. 。 5. The oxazole derivative according to claim 1, characterized in that, At least one of Ar1 and Ar2 is selected from formula A, and the remainder is selected from one of the following groups. 。 6. The oxazole derivative according to claim 1, characterized in that, The L is selected from a single bond or one of the following groups: 。 7. An oxazole derivative, characterized in that, The oxazole derivative is selected from at least one of the structures shown below. 。 8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a cathode, an organic functional layer, and an anode, wherein the organic functional layer contains the oxazole derivative as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic functional layer includes at least one of an electron transport region and a light-emitting layer, wherein the electron transport region and at least one of the light-emitting layers contain the oxazole derivative according to any one of claims 1 to 7.

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