An organic electroluminescent device

Abstract

The application provides an organic electroluminescent device, and belongs to the technical field of organic electroluminescent devices.The organic electroluminescent device can effectively prevent the diffusion of the electrons / holes transferred to the light-emitting layer to the hole / electron transport region, so that the probability of the recombination of the holes and the electrons in the light-emitting layer into excitons is increased, and the recombination region of the excitons can be closer to the center of the light-emitting layer, so that the light-emitting efficiency of the organic electroluminescent device is greatly improved, and the irreversible decomposition reaction caused by oxidation due to the diffusion of the electrons / holes is avoided, so that the service life of the organic electroluminescent device is prolonged.The organic electroluminescent device has good application effect and industrialization prospect.

Description

Technical Field

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

[0002] Organic light-emitting devices (OLEDs) are self-emissive display devices that convert electrical energy into light energy by applying electrical energy to organic electroluminescent materials. Their advantages include wider viewing angles, higher contrast ratios, and faster response times. OLEDs typically consist of an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include hole transport regions, electron transport regions, and an emissive layer. Hole transport regions may include hole injection layers, hole transport layers, electron blocking layers, and emissive auxiliary layers, while electron transport regions may include electron injection layers, electron transport layers, and hole blocking layers.

[0003] The light-emitting principle of OLEDs is that holes from the anode and electrons from the cathode migrate in the organic layer and are injected into the light-emitting layer after a voltage is applied. High-energy excitons are generated through the recombination of holes and electrons. When the excitons return from the excited state to the ground state, they emit radiation decay, and the decayed energy is emitted in the form of light, thus making the device emit light.

[0004] However, current OLED devices suffer from the following problems: after holes / electrons are transported to the emissive layer, they accumulate and then diffuse into the electron / hole transport region. This reduces the probability of holes and electrons recombinating into excitons in the emissive layer, and the exciton recombination region is deviated from the center of the emissive layer, resulting in a decrease in luminous efficiency. Furthermore, the diffusion of holes / electrons affects device lifetime and reduces device performance. To improve device characteristics, blocking layers are currently used to prevent the movement and diffusion of electrons / holes; however, in practice, satisfactory results have not yet been achieved. Summary of the Invention

[0005] To address the aforementioned problems, this invention provides an organic electroluminescent device that not only possesses high luminous efficiency but also a long lifespan.

[0006] This invention provides an organic electroluminescent device, comprising an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the hole transport region comprises the structure shown in Formula 1.

[0007]

[0008] In Formula 1, Ar1 and Ar2, whether the same or different, are selected from the structures shown below.

[0009]

[0010] The same or different R1 to R4 are selected from any one of hydrogen, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, and substituted or unsubstituted C6 to C18 aryl;

[0011] The same or different a1 is selected from 0, 1, 2 or 3; the same or different a2 is selected from 0, 1, 2, 3 or 4; the same or different a3 and a4 are selected from 0, 1, 2, 3, 4 or 5; when there are two or more R1, the two or more R1 are the same or different from each other, or adjacent R1 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or adjacent R2 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or adjacent R3 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R4, the two or more R4 are the same or different from each other, or adjacent R4 are connected to each other to form a substituted or unsubstituted ring;

[0012] The Ar3 is selected from any of the structures shown below.

[0013]

[0014] The same or different R5 is selected from any one of hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C18 aryl;

[0015] The same or different b1 is selected from 0, 1, 2, 3, 4 or 5; the same or different b2 is selected from 0, 1, 2, 3 or 4; the same or different b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R5, the two or more R5 are the same or different from each other;

[0016] The L1 to L3 are the same or different and are selected from any one of the single-bonded, substituted or unsubstituted C6 to C18 aryl groups;

[0017] The electron transport region includes the structure shown in Equation 2.

[0018]

[0019] A is selected from any of the structures shown below.

[0020]

[0021] The x that is the same or different is selected from CR6 or N;

[0022] The Ra, Rb, Rc, and R6 are the same or different and are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0023] The La is selected from any one of single-bonded, substituted or unsubstituted C6 to C18 aryl groups;

[0024] The B is selected from the structure shown below.

[0025]

[0026] The z that are the same or different are selected from CR7 or N;

[0027] X1 is selected from any one of O, S, and NR8;

[0028] The same or different R7 and Rd are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0029] The R8s, whether identical or different, are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0030] The L b L c L d The same or different is selected from any one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, and substituted or unsubstituted terphenylene.

[0031] The beneficial effects of this invention are:

[0032] The organic electroluminescent device provided by this invention has a hole transport region comprising a structure of Formula 1 and an electron transport region comprising a structure of Formula 2. It can effectively block the diffusion of electrons / holes transferred to the light-emitting layer to the hole / electron transport region, thereby increasing the probability of holes and electrons recombinating into excitons inside the light-emitting layer. At the same time, it allows the exciton recombination region to be closer to the center of the light-emitting layer, greatly improving the luminous efficiency of the electroluminescent device and avoiding irreversible decomposition reactions caused by oxidation due to electron / hole diffusion, thus extending the service life of the electroluminescent device. Attached Figure Description

[0033] Figure 1 This is a cross-sectional view of the structure of an organic electroluminescent device 20 according to an embodiment of the present invention. Detailed Implementation

[0034] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some, not all, of the embodiments of the present invention. Furthermore, the embodiments and features in the embodiments of the present invention can be combined with each other without conflict. Based on the described embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0035] Unless otherwise defined, the technical or scientific terms used in this invention shall have the ordinary meaning understood by one of ordinary skill in the art to which this invention pertains. The terms "comprising" or "including," and similar terms used in this invention, mean that the device or object preceding the term encompasses the device or object listed following the term and its equivalents, without excluding other devices or objects. Terms such as "connected" or "linked" are not limited to physical or mechanical connections, but may include electrical connections, whether direct or indirect. Terms such as "inner," "outer," "upper," and "lower" are used only to indicate relative positional relationships; when the absolute position of the described object changes, the relative positional relationship may also change accordingly.

[0036] 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.

[0037] In this instruction manual, This refers to the portion that is connected to another substituent.

[0038] In this instruction manual, This refers to the portion that is connected to another substituent.

[0039] 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.

[0040] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent or Can represent And so on.

[0041] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine;

[0042] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0043] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto.

[0044] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, anthracene, phenanthrene, pyrene, triphenylene, perylene, etc., but are not limited thereto.

[0045] The heteroaryl group described in this invention refers to a monovalent group formed by removing a hydrogen atom from the nuclear atom of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatom may be one or more of N, O, S, Si, and P, and may be a monocyclic heteroaryl or a fused-ring heteroaryl. Preferably, it has 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 3 to 12 carbon atoms, and most preferably 3 to 8 carbon atoms. Examples include pyrroleyl, pyridyl, pyrimidinyl, triazineyl, thiopheneyl, furanyl, indoleyl, quinolinyl, isoquinolinyl, oxazolyl, thiazolyl, and imidyl. Azolyl, benzothiophenyl, benzofuranyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, pyridoxazolyl, pyridoxiazolyl, pyridimidazolyl, pyrimidinoxazolyl, pyrimidinoxazolyl, pyrimidinoxazolyl, pyrimidinoxazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenazinyl, quinoxolinyl, quinazolinyl, quinolinooxazolyl, quinolinothiazolyl, quinolinoimidazolyl, purinel, 2-purinel, N-imidazolyl, etc., but not limited to these.

[0046] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. Apart from being divalent groups, they are subject to the same description of aryl groups as described above.

[0047] The heteroaryl group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the nuclear atom of an aromatic heterocycle composed of carbon and heteroatoms. Apart from being divalent groups, they are subject to the above description of heteroaryl groups.

[0048] The term "substitution" as used in this invention refers to the replacement of hydrogen atoms in a compound group with other atoms or groups, and the substitution position is not limited.

[0049] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl groups, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl groups. The substituted or unsubstituted C6-C30 aromatic amino group, substituted or unsubstituted C6-C30 aryloxy group, preferably protium, deuterium, tritium, halogen atom, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, C2-C25 heteroaryl, and specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, and n-propyl. Isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, phenyl, tolyl, mesitylene, pentadeuteryl, biphenyl, naphthyl, anthracene, phenanthrene, benzophenanthrene, pyrene, triphenylene alkyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, carbazole, 9-phenylcarbazole, spirodifluorenyl, carbazole-indole, pyrrole, furanyl, thiophene, indole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazinyl The substituents include, but are not limited to, azole, thiazolyl, imidazole, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, pyridinozolyl, pyridinozothiazolyl, pyridinozothiazolyl, pyrimidinozolyl, pyrimidinozothiazolyl, pyrimidinozolyl, quinolinyl, isoquinolinyl, quinolinozolyl, quinolinozothiazolyl, quinolinozolyl, phenothiazinyl, phenothiazinyl, acridineyl, etc. Alternatively, when there are two or more substituents, adjacent substituents may bond to form a ring; when there are two or more substituents, the two or more substituents may be the same as or different from each other.

[0050] The linking to form a substituted or unsubstituted ring, as described in this invention, refers to two groups linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0051]

[0052] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring. Examples may include benzene, pyridine, pyrimidine, naphthalene, fluorene, cyclopentene, cyclohexene, cyclopentane, cyclohexane, cyclohexane, benzobenzene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0053] The embodiments of the organic electroluminescent device of the present invention will be described below with reference to the accompanying drawings. However, the embodiments of the present invention may be modified into other forms, and the scope of the present invention is not limited to the embodiments described below.

[0054] Figure 1 This is a cross-sectional view schematically illustrating the structure of an organic electroluminescent device 20 according to an embodiment of the present invention.

[0055] Reference Figure 1 The organic electroluminescent device 20 of the present invention includes an anode 1, a cathode 2, a light-emitting layer 3 located between the anode 1 and the cathode 2, a hole transport region 4 located between the anode 1 and the light-emitting layer 3, and an electron transport region 5 located between the light-emitting layer 3 and the cathode 2.

[0056] The organic electroluminescent device 20 of the present invention provides hole transport region 4 and electron transport region 5 on both sides of the light-emitting layer 3. The hole transport region 4 includes a structure of type 1, which can effectively improve the hole transport rate and block electrons diffusing from the light-emitting layer side. The electron transport region 5 includes a structure of type 2, which can effectively improve the electron transport rate and block holes diffusing from the light-emitting layer side. The arrangement of hole transport region 4 and electron transport region 5 can not only effectively confine holes and electrons inside the light-emitting layer 3 and increase the recombination probability of holes and electrons, but also reduce the device oxidation problem caused by the diffusion of holes and electrons to both sides, thereby improving the luminous efficiency and service life of the organic electroluminescent device 20.

[0057] The following describes in more detail the configuration of the organic electroluminescent device 20 having the hole transport region 4 and the electron transport region 5.

[0058] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0059] anode

[0060] In the organic electroluminescent device 20 of the present invention, the anode 1 preferably uses a high work function material (work function greater than 4.0 eV) that can promote hole injection into other functional layers. Specific examples of anode 1 materials that can be used in the present invention may include metals, such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides, such as indium tin oxide-silver-indium tin oxide (ITO-Ag-ITO); conductive polymers, such as poly(3-methylthiophene), polypyrrole, polyaniline, poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), etc., but are not limited thereto.

[0061] Organic layer

[0062] In the organic electroluminescent device 20 of the present invention, the organic layer can be used without limitation with the conventional configuration used in organic electroluminescent devices, and it can include one or more of the group consisting of hole transport region 4, light-emitting layer 3 and electron transport region 5.

[0063] Hole transport region

[0064] In the organic electroluminescent device 20 of the present invention, the hole transport region 4 is included to move holes injected from the anode 1 to the light-emitting layer 3.

[0065] The hole transport region 4 includes the structure shown in Formula 1.

[0066]

[0067] In Formula 1, Ar1 and Ar2, whether the same or different, are selected from the structures shown below.

[0068]

[0069] The same or different R1 to R4 are selected from any one of hydrogen, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, and substituted or unsubstituted C6 to C18 aryl;

[0070] The same or different a1 is selected from 0, 1, 2 or 3; the same or different a2 is selected from 0, 1, 2, 3 or 4; the same or different a3 and a4 are selected from 0, 1, 2, 3, 4 or 5; when there are two or more R1, the two or more R1 are the same or different from each other, or adjacent R1 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or adjacent R2 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or adjacent R3 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R4, the two or more R4 are the same or different from each other, or adjacent R4 are connected to each other to form a substituted or unsubstituted ring;

[0071] The Ar3 is selected from any of the structures shown below.

[0072]

[0073] The same or different R5 is selected from any one of hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C18 aryl;

[0074] The same or different b1 is selected from 0, 1, 2, 3, 4 or 5; the same or different b2 is selected from 0, 1, 2, 3 or 4; the same or different b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R5, the two or more R5 are the same or different from each other;

[0075] The L1 to L3 are the same or different and are selected from any one of the single-bonded, substituted or unsubstituted C6 to C18 aryl groups.

[0076] Preferably, Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below.

[0077]

[0078]

[0079] The R9, whether identical or different, is selected from any one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, tolyl, tert-butylphenyl, adamantylphenyl, biphenyl, and naphthyl;

[0080] The same or different c1 is selected from 0, 1, 2, 3, 4 or 5; the same or different c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R9, the two or more R9 are the same or different from each other.

[0081] Preferably, the Ar3, whether identical or different, is selected from any of the structures shown below.

[0082]

[0083] Preferably, the L1 to L3, whether identical or different, are selected from single bonds or any of the structures shown below.

[0084]

[0085] The R 12 The same or different from any one selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl;

[0086] The same or different values ​​of e1 are selected from 0, 1, 2, 3, or 4; the same or different values ​​of e2 are selected from 0, 1, 2, or 3; the same or different values ​​of e3 are selected from 0, 1, 2, 3, 4, or 5; the same or different values ​​of e4 are selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... 12 At that time, two or more R 12 They may be the same as or different from each other.

[0087] Preferably, the structure of Formula 1 is selected from any one of the following structures.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] The hole transport region 4 may include an electron blocking layer 6, and at least one of a hole injection layer 8 and a hole transport layer 7.

[0096] The hole transport region 4, based on the light-emitting layer 3, may have a structure comprising an electron blocking layer 6, a hole injection layer 8, a hole transport layer 7, an electron blocking layer 6 and a hole injection layer 8, a hole transport layer 7 and a hole injection layer 8, an electron blocking layer 6 and a hole transport layer 7, or a structure comprising an electron blocking layer 6, a hole transport layer 7, and a hole injection layer 8. Preferably, the hole transport region 4 includes an electron blocking layer 6, a hole transport layer 7, and a hole injection layer 8.

[0097] The hole injection layer 8 described in this invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used in the hole injection layer 8 in this invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, and phenazine compounds, such as copper phthalocyanine (CuPc), titanium phthalocyanine, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), and N,N,N',N'-tetra(4-methoxyphenyl) Benzidine (MeO-TPD), diquinoxolino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), etc., but not limited to these.

[0098] The hole transport layer 7 described in this invention preferably uses a material with good hole transport performance. Specific examples of materials that can be used in the hole transport layer 7 in this invention may include diphenylamine compounds, triphenylamine compounds, fluorene compounds, and carbazole compounds, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), etc., but are not limited thereto. Preferably, the hole transport layer 7 of the present invention is selected from the structure shown in Formula 1.

[0099] The electron blocking layer 6 described in this invention is preferably made of a material with good electron blocking properties. Specific examples of electron blocking layer 6 materials that can be used in this invention may include diphenylamine compounds, triphenylamine compounds, fluorene compounds, triaromatic amine compounds, and carbazole compounds, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), etc., but are not limited thereto. Preferably, the electron blocking layer 6 of the present invention is selected from the structure shown in Formula 1.

[0100] Emissive layer

[0101] In the organic electroluminescent device 20 of the present invention, the light-emitting layer 3 is a layer in which holes and electrons meet to form excitons. Depending on the material constituting the light-emitting layer 3, the color of the light emitted by the organic electroluminescent device can be changed. The light-emitting layer 3 comprises a host material and a dopant material, and their mixing ratio can be appropriately adjusted within a range known in the art. Based on the total weight of the light-emitting layer 3, the light-emitting layer 3 may contain 70 to 99.9 parts by weight of the host material and 0.1 to 30 parts by weight of the dopant material. Preferably, when the light-emitting layer 3 is blue fluorescent, green fluorescent, or red fluorescent, the light-emitting layer 3 may contain 80 to 99.9 parts by weight of the host material and 0.1 to 20 parts by weight of the dopant material. Preferably, when the light-emitting layer 3 is blue fluorescent, green fluorescent, or red phosphorescent, it may contain 70 to 99 parts by weight of the host material and 1 to 30 parts by weight of the dopant material. The host material comprising the light-emitting layer 3 of the present invention can be a host material known in the art, which can be an alkali metal coordination compound, an alkaline earth metal coordination compound, or a condensed aromatic ring derivative, etc. Specific examples of host materials that can be used in the present invention may include one or more combinations of aluminum coordination compounds, beryllium coordination compounds, anthracene derivatives, pyrene derivatives, triphenylene derivatives, carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives, such as 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazole)biphenyl (CPB), 9,9'-(1 3-Phenyl)di-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (α-ADN), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazole)benzene (TCP), 2-tert-butyl 2,7-Bis[9,9-bis(4-methylphenyl)-2-fluorenyl]-9,9-bis(4-methylphenyl)fluorenyl (TDAF), 2-methyl-9,10-bis(2-naphthyl)anthracene (MADN), 9,9',10,10'-tetraphenyl-2,2'-bianthracene (TPBA), 10,10'-bis(4-biphenyl)-9,9'-bianthracene (BANE), 4 4'-Di[10-(1-naphthyl)9-anthrayl]biphenyl (BUBH-3), 1-(7-(9,9'-anthrayl)-9,9-dimethyl-9H-2-fluorenyl)pyrene (BAnFPye), 9,10-diphenylanthracene (ADP), 2-methyl-9,10-di(1-naphthyl)anthracene (MAD-1N), 4,4',4"-tris(9-carbazolyl)triphenylamine (TCTA), 4,4'-bis(9-carbazolyl)-2,2'-Dimethylbiphenyl (CDBP), 2,7-bis(9-carbazolyl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(9-carbazolyl)-9,9-spirodifluorene (Spiro-CBP), 9,9-bis[4-(9-carbazolyl)-phenyl]fluorene (FL-2CBP), 2,6-bis(3-(9H-9-carbazolyl)phenyl)pyridine (26DCzPPy), 3,5-bis(9H-9-carbazolyl)biphenyl (Ph-MCP), 3-(3-(9H-9-carbazolyl)phenyl)benzofuran[2,3-b]pyridine Pyridine (PCz-BFP), 2,6-bis(9H-9-carbazolyl)pyridine (PYD-2Cz), 3-(4-(9H-9-carbazolyl)phenyl)-9-(4,6-diphenyl-1,3,5-2-triazinyl)-9H-carbazole (CPCBPTz), 4,6-bis(3-(9H-9-carbazolyl)phenyl)pyrimidine (46DCzPPM), 9-(3,5-bis(2-triphenyl-yl)phenyl)-9H-carbazole (DTP-mCP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), etc., but not limited to these. The doping material contained in the light-emitting layer 3 of the present invention can be a doping material known in the art, which can be a red doping material, a green doping material, or a blue doping material. The red dopant can be one or a combination of more than one of octaethylporphyrin platinum(II) (PtOEP), tris(2-phenylisoquinoline)iridium(Ir(piq)3), and bis(2-(2'-benzothiophene)-pyridine-N,C3')(acetylacetone)iridium(Btp2Ir(acac)); the green dopant can be tris(2-phenylpyridine)iridium(Ir(ppy)3), bis(2-phenylpyridine)(acetylacetone)iridium(III) (Ir(ppy)2(acac)), tris(2-(4-tolyl)phenylpyridine)iridium(Ir(mppy)3), 10-(2-benzothiazolyl)-1 The blue doped material may be one or more of the following: 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]-quinazin-11-one (C545T); the blue doped material may be one or more of the following: bis[3,5-difluoro-2-(2-pyridyl)phenyl(pyridinyl)iridium(III) (F2Irpic), 4,4'-bis(2,2'-diphenylvinyl-1-yl)biphenyl (DPVBi), 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0102] The light-emitting layer 3 of this invention can be a single layer composed of one substance, a single layer composed of multiple different substances, or a multilayer consisting of two or more layers, each composed of different substances. When the light-emitting layer 3 has multiple layers, the organic electroluminescent element can emit light of various colors.

[0103] The organic electroluminescent device of the present invention can comprise a plurality of light-emitting layer stacks, each including at least one of the light-emitting layers 3. The plurality of light-emitting layers in the light-emitting layer stack can each emit light of a different color or emit light of the same color. That is, the emission color can be changed according to the material constituting the light-emitting layer. For example, the plurality of light-emitting layer stacks can include materials that emit blue, green, red, yellow, white, etc., and can be formed using phosphorescent or fluorescent materials. In this case, the colors emitted by each light-emitting layer can be complementary colors. Alternatively, the colors can be selected according to a combination of colors that emit white light.

[0104] Electronic transmission area

[0105] In the organic electroluminescent device 20 of the present invention, the electron transport region 5 serves to move electrons injected from the cathode 2 to the light-emitting layer 3.

[0106] The electron transport region 5 of the present invention includes the structure shown in Formula 2.

[0107]

[0108] A is selected from any of the structures shown below.

[0109]

[0110] The x that is the same or different is selected from CR6 or N;

[0111] The Ra, Rb, Rc, and R6 are the same or different and are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0112] The La is selected from any one of single-bonded, substituted or unsubstituted C6 to C18 aryl groups;

[0113] The B is selected from the structure shown below.

[0114]

[0115] The z that are the same or different are selected from CR7 or N;

[0116] X1 is selected from any one of O, S, and NR8;

[0117] The same or different R7 and Rd are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0118] The R8s, whether identical or different, are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0119] The L b L c L d The same or different is selected from any one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, and substituted or unsubstituted terphenylene.

[0120] Preferably, the structure of Formula 2 is selected from any one of the structures shown in Formulas 2-1 to 2-6 below.

[0121]

[0122] Preferably, the x values ​​that are the same or different are selected from CR6 or N;

[0123] The R6 is the same as or different from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted norbornel, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, and substituted or unsubstituted imidazolyl.

[0124] Preferably, A is selected from any of the following structures.

[0125]

[0126]

[0127] The x that is the same or different is selected from CR6 or N;

[0128] The R6, R 10 The same or different are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl;

[0129] The R6 may be substituted by one or more substituents, which may be the same or different and are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.

[0130] The R 10 It can be substituted by one or more substituents, wherein the same or different substituents are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents are the same or different from each other;

[0131] The values ​​of d1 (same or different) are selected from 0, 1, 2, 3, 4, or 5; the values ​​of d2 (same or different) are selected from 0, 1, 2, 3, or 4; the values ​​of d3 (same or different) are selected from 0, 1, 2, 3, 4, 5, 6, or 7; the values ​​of d4 (same or different) are selected from 0, 1, 2, 3, 4, 5, or 6; the values ​​of d5 (same or different) are selected from 0, 1, 2, 3, 4, or 5; the values ​​of d6 (same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the values ​​of d7 (same or different) are selected from 0, 1, or 2; when there are two or more R... 10 At that time, two or more R 10 They may be the same as or different from each other.

[0132] In this invention, preferably, among the multiple x (4 x) on the same ring, at most 2 or at most 1 x are selected from N, and the rest are selected from CR6.

[0133] Preferably, B is selected from any of the following structures:

[0134]

[0135] X1 is selected from any one of O, S, and NR8;

[0136] The R8 group, whether identical or different, is selected from any one of methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, tolyl, deuterated phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl.

[0137] The R7, whether identical or different, is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl.

[0138] The R7 may be substituted by one or more substituents, which may be the same or different and are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.

[0139] The m1 that is the same or different is selected from 0, 1, 2, 3 or 4; the m2 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 that is the same or different is selected from 0, 1, 2 or 3; the m5 that is the same or different is selected from 0, 1, 2, 3, 4 or 5; the m6 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m7 that is the same or different is selected from 0, 1 or 2; the m8 that is the same or different is selected from 0 or 1; when there are two or more R7, the two or more R7 are the same or different from each other.

[0140] Preferably, the L b L c L d The same or different ones are selected from single bonds or any of the structures shown below.

[0141]

[0142] The R 11 The same or different are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl;

[0143] The n1 that is the same or different is selected from 0, 1, 2, 3 or 4; the n2 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R 11 At that time, two or more R 11 They may be the same as or different from each other.

[0144] Preferably, the structure of Formula 2 is selected from any one of the following structures.

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] The electron transport region 5 includes a hole blocking layer 9, and at least one of an electron injection layer 11 and an electron transport layer 10.

[0156] The electron transport region 5, based on the light-emitting layer 3, may have a structure comprising a hole blocking layer 9, an electron injection layer 11, an electron transport layer 10, a hole blocking layer 9 and an electron injection layer 11, an electron transport layer 10 and an electron injection layer 11, a hole blocking layer 9 and an electron transport layer 10, or a structure comprising a hole blocking layer 9, an electron transport layer 10, and an electron injection layer 11. Preferably, the electron transport region 5 includes a hole blocking layer 9, an electron transport layer 10, and an electron injection layer 11.

[0157] In the organic electroluminescent device 20 of the present invention, the hole blocking layer 9 is preferably made of a material with good hole blocking performance. Specific examples of hole blocking layer 9 materials that can be used in the present invention may include imidazole, triazole, phenanthroline derivatives, quinoline, etc., such as 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4, Examples of suitable hole-blocking layers include, but are not limited to, 6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthyl-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), and 8-hydroxyquinoline-lithium (LiQ). Preferably, the hole-blocking layer 9 is selected from the structure shown in Formula 2.

[0158] In the organic electroluminescent device 20 of the present invention, the electron transport layer 10 preferably uses a material with strong electron-withdrawing ability and low HOMO and LUMO energy levels. Specific examples of electron transport layer 10 materials that can be used in the present invention may include imidazole, triazole, phenanthroline derivatives, quinoline, etc., such as 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4 Examples of electron transport layers include, but are not limited to, 4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthyl-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), and 8-hydroxyquinoline-lithium (LiQ). Preferably, the electron transport layer 10 is selected from the structure shown in Formula 2.

[0159] In the organic electroluminescent device 20 of the present invention, the electron injection layer 11 is preferably made of a material with a small barrier difference with the adjacent organic transport material and has the effect of injecting electrons from the cathode. Specific examples of electron injection layer 11 materials that can be used in the present invention may include alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF2), metal oxides (such as Al2O3, MoO3), but are not limited thereto.

[0160] cathode

[0161] In the organic electroluminescent device 20 of the present invention, the cathode 2 is preferably made of a low work function material that can promote electron injection into the organic layer. Specific examples of cathode 2 materials that can be used in the present invention may include metals such as aluminum, magnesium, silver, indium, tin, titanium and their alloys; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, etc., but are not limited thereto.

[0162] The organic electroluminescent device 20 of the present invention may further include a capping layer. The capping layer of the present invention preferably uses a material that can improve the optical coupling effect. Specific examples of capping layer materials that can be used in the present invention may include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, etc., but are not limited thereto.

[0163] The organic electroluminescent device 20 of the present invention may further include a substrate. Preferably, the substrate is made of a material that does not change during the formation of electrodes and other functional layers. Specific examples of substrate materials that can be used in the present invention include glass, quartz, plastic, polymer films, silicon, etc., but are not limited thereto. The substrate may be retained in a light-emitting device or electronic device utilizing the organic electroluminescent device of the present invention, or it may not be retained in the final product but only serve as a support during the manufacturing process of the organic electroluminescent device.

[0164] However, the structure of the organic electroluminescent device 20 described in this invention is not limited thereto. The organic electroluminescent device 20 described in this invention can be selected and combined according to the device parameter requirements and material characteristics. Some organic layers can be added or omitted, and organic layers with the same function can be made into a stacked structure of two or more layers.

[0165] The organic electroluminescent device 20 of the present invention can be either a top-emitting device or a bottom-emitting device. The difference between the two lies in whether the light emission direction of the device is through the substrate or away from the substrate. For a bottom-emitting device, the light emission direction is through the substrate; for a top-emitting device, the light emission direction is away from the substrate.

[0166] The organic electroluminescent device 20 of the present invention can have either an upright structure or an inverted structure. The difference between the two lies in the order in which the organic layers are fabricated. Specifically, in the upright structure, a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, a hole transport layer, a hole injection layer, and an anode are formed sequentially on the substrate. In the inverted structure, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode are formed sequentially on the substrate.

[0167] The organic electroluminescent device 20 of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.

[0168] The organic electroluminescent device 20 described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0169] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0170] This invention also provides a method for preparing compounds represented by Formulas 1 and 2, but the preparation method of this invention is not limited thereto. The core structure of the compounds of Formulas 1 and 2 can be prepared by the reaction routes shown below, the substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0171] Preparation of Formula 1:

[0172]

[0173] Preparation of Formula 2:

[0174]

[0175] Xa and Xb, whether the same or different, are selected from I, Br, and Cl;

[0176] Description of raw materials, reagents, and characterization equipment:

[0177] The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; 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 the present invention are of reagent purity.

[0178] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0179] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0180] Synthesis Example 1: Preparation of Compounds 1-6

[0181]

[0182] Preparation of intermediate 1-6-A:

[0183] Under nitrogen protection, 1-6-a (21.17 g, 60 mmol), 1-6-b (20.01 g, 60 mmol), sodium tert-butoxide (11.53 g, 120 mmol), and Pd(dppf)Cl2 (0.44 g, 0.60 mmol) were added sequentially to a reaction flask. 400 mL of toluene was added to dissolve them, and the mixture was heated to reflux for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, washed three times with distilled water, allowed to stand, and separated. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The obtained solid was recrystallized from ethyl acetate to give intermediate 1-6-A (33.92 g, yield 87%). HPLC analysis showed the solid purity to be ≥99.85%. Mass spectrometry m / z: 649.2783 (theoretical value: 649.2770).

[0184] Preparation of compounds 1-6:

[0185] Under nitrogen protection, intermediates 1-6-A (19.50 g, 30 mmol), 1-6-c (6.74 g, 30 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), BINAP (0.37 g, 0.60 mmol), and sodium tert-butoxide (4.81 g, 50 mmol) were added sequentially to a reaction flask. 300 mL of toluene was added, and the mixture was stirred to dissolve. The mixture was heated under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, washed three times with distilled water, allowed to stand, and separated. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The resulting solid was recrystallized from toluene to give compound 1-6 (21.37 g, 85% yield). HPLC analysis showed the solid purity to be ≥99.98%. Mass spectrometry m / z: 837.4351 (theoretical value: 837.4335). Theoretical element content (%) C 64 H 55 N: C, 91.71; H, 6.61; N, 1.67. Measured elemental content (%): C, 91.71; H, 6.59; N, 1.69.

[0186] Synthetic Example 2: Preparation of Compounds 1-25

[0187]

[0188] According to the preparation method in Example 1, equimolar amounts of 1-6-c were replaced with equimolar amounts of 1-25-c to obtain compound 1-25 (22.39 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 909.4321 (theoretical value: 909.4335). Theoretical elemental content (%) C 70 H 55 N: C, 92.37; H, 6.09; N, 1.54. Measured element content (%): C, 92.35; H, 6.10; N, 1.55.

[0189] Synthetic Example 3: Preparation of Compounds 1-56

[0190]

[0191] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-56-a, 1-56-b, and 1-56-c, respectively, to obtain compound 1-56 (22.62 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 953.4035 (theoretical value: 953.4022). Theoretical elemental content (%) C 74 H 51 N: C, 93.14; H, 5.39; N, 1.47. Measured element content (%): C, 93.10; H, 5.42; N, 1.48.

[0192] Synthetic Example 4: Preparation of Compounds 1-88

[0193]

[0194] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-88-a, 1-88-b, and 1-88-c, respectively, to obtain compound 1-88 (22.39 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 909.4324 (theoretical value: 909.4335). Theoretical elemental content (%) C 70 H 55 N: C, 92.37; H, 6.09; N, 1.54. Measured elemental content (%): C, 92.34; H, 6.13; N, 1.53.

[0195] Synthetic Example 5: Preparation of Compounds 1-96

[0196]

[0197] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-96-a, 1-96-b, and 1-96-c, respectively, to obtain compound 1-96 (23.04 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 947.4508 (theoretical value: 947.4491). Theoretical elemental content (%) C 73 H 57 N: C, 92.46; H, 6.06; N, 1.48. Measured elemental content (%): C, 92.48; H, 6.01; N, 1.51.

[0198] Synthetic Example 6: Preparation of Compounds 1-112

[0199]

[0200] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-112-a, 1-88-b, and 1-112-c, respectively, to obtain compound 1-112 (24.68 g), with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 1067.5448 (theoretical value: 1067.5430). Theoretical elemental content (%) C 82 H 69 N: C, 92.18; H, 6.51; N, 1.31. Measured element content (%): C, 92.22; H, 6.52; N, 1.26.

[0201] Synthetic Example 7: Preparation of Compounds 1-115

[0202]

[0203] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-115-a, 1-96-b, and 1-115-c, respectively, to obtain compound 1-115 (20.69 g), with an HPLC purity ≥ 99.99%. Mass spectrometry m / z: 801.3411 (theoretical value: 801.3396).

[0204] Theoretical element content (%) C 62 H 43 N: C, 92.85; H, 5.40; N, 1.75. Measured element content (%): C, 92.86; H, 5.39; N, 1.75.

[0205] Synthetic Example 8: Preparation of Compounds 1-121

[0206]

[0207] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-A and 1-6-c were replaced with equimolar amounts of 1-115-A and 1-121-c, respectively, to obtain compound 1-121 (21.63 g), with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 857.4039 (theoretical value: 857.4022). Theoretical elemental content (%) C 66 H 51 N: C, 92.38; H, 5.99; N, 1.63. Measured element content (%): C, 92.37; H, 6.01; N, 1.62.

[0208] Synthetic Example 9: Preparation of Compounds 1-143

[0209]

[0210] Preparation of intermediate 1-143-a:

[0211] Under nitrogen protection, 1-143-d (16.34 g, 95 mmol), 1-143-e (38.86 g, 90 mmol), potassium carbonate (18.66 g, 135 mmol), and Pd(PPh3)4 (1.04 g, 0.90 mmol) were added sequentially to a reaction flask. 400 mL of a toluene / ethanol / water (3:1:1) mixed solvent was added, and the mixture was stirred. The reaction system was heated under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give intermediate 1-143-a (37.08 g, 86% yield). HPLC analysis showed the solid purity to be ≥99.76%. Mass spectrometry m / z: 478.1472 (theoretical value: 478.1488).

[0212] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-143-a, 1-96-b, and 1-143-c, respectively, to obtain compound 1-143 (22.19 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 901.3721 (theoretical value: 901.3709).

[0213] Theoretical element content (%) C 70 H 47 N: C, 93.20; H, 5.25; N, 1.55. Measured element content (%): C, 93.16; H, 5.26; N, 1.58.

[0214] Synthetic Example 10: Preparation of Compounds 1-148

[0215]

[0216] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-148-a, 1-96-b, and 1-148-c, respectively, to obtain compound 1-148 (23.08 g), with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 985.4634 (theoretical value: 985.4648).

[0217] Theoretical element content (%) C 76 H 59 N: C, 92.55; H, 6.03; N, 1.42. Measured elemental content (%): C, 92.54; H, 6.03; N, 1.43.

[0218] Synthetic Example 11: Preparation of Compounds 1-166

[0219]

[0220] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-166-a, 1-166-b, and 1-166-c, respectively, to obtain compound 1-166 (22.56 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 927.3848 (theoretical value: 927.3865).

[0221] Theoretical element content (%) C 72 H 49 N: C, 93.17; H, 5.32; N, 1.51. Measured elemental content (%): C, 93.14; H, 5.31; N, 1.55.

[0222] Synthetic Example 12: Preparation of Compounds 1-191

[0223]

[0224] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-191-a, 1-88-b, and 1-191-c, respectively, to obtain compound 1-191 (23.39 g), with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 1011.4822 (theoretical value: 1011.4804). Theoretical elemental content (%) C 78 H 61N: C, 92.54; H, 6.07; N, 1.38. Measured elemental content (%): C, 92.51; H, 6.09; N, 1.39.

[0225] Synthesis Example 13: Preparation of Compound 1-202

[0226]

[0227] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-202-a, 1-88-b, and 1-202-c, respectively, to obtain compound 1-202 (21.63 g), with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 857.4035 (theoretical value: 857.4022).

[0228] Theoretical element content (%) C 66 H 51 N: C, 92.38; H, 5.99; N, 1.63. Measured element content (%): C, 92.37; H, 6.01; N, 1.62.

[0229] Synthetic Example 14: Preparation of Compounds 1-211

[0230]

[0231] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-211-a, 1-56-b, and 1-211-c, respectively, to obtain compound 1-211 (22.70 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 933.4322 (theoretical value: 933.4335).

[0232] Theoretical element content (%) C 72 H 55 N: C, 92.57; H, 5.93; N, 1.50. Measured element content (%): C, 92.58; H, 5.95; N, 1.47.

[0233] Synthetic Example 15: Preparation of Compounds 1-216

[0234]

[0235] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-216-a, 1-88-b, and 1-216-c, respectively, to obtain compound 1-216 (24.22 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 1061.4978 (theoretical value: 1061.4961). Theoretical elemental content (%) C 82 H 63 N: C, 92.70; H, 5.98; N, 1.32. Measured element content (%): C, 92.64; H, 6.01; N, 1.35.

[0236] Synthetic Example 16: Preparation of Compounds 1-227

[0237]

[0238] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-227-a, 1-88-b, and 1-227-c, respectively, to obtain compound 1-227 (22.85 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 963.4819 (theoretical value: 963.4804).

[0239] Theoretical element content (%) C 74 H 61 N: C, 92.17; H, 6.38; N, 1.45. Measured element content (%): C, 92.17; H, 6.39; N, 1.44.

[0240] Synthetic Example 17: Preparation of Compounds 1-236

[0241]

[0242] According to the preparation method in Example 1, equimolar amounts of 1-6-A and 1-6-c were replaced with equimolar amounts of 1-202-A and 1-236-c, respectively, to obtain compound 1-236 (22.56 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 927.3848 (theoretical value: 927.3865). Theoretical elemental content (%) C 72 H 49 N: C, 93.17; H, 5.32; N, 1.51. Measured elemental content (%): C, 93.19; H, 5.34; N, 1.47.

[0243] Synthetic Example 18: Preparation of Compounds 1-255

[0244]

[0245] According to the preparation method in Synthesis Example 9, equimolar amounts of 1-143-d, 1-143-e, 1-96-b, and 1-143-c were replaced with equimolar amounts of 1-255-d, 1-255-e, 1-56-b, and 1-255-c, respectively, to obtain compound 1-255 (24.68 g) with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 1141.5571 (theoretical value: 1141.5587). Theoretical elemental content (%) C 88 H 71 N: C, 92.51; H, 6.26; N, 1.23. Measured element content (%): C, 92.49; H, 6.29; N, 1.22.

[0246] Synthetic Example 19: Preparation of Compounds 1-263

[0247]

[0248] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a and 1-6-c were replaced with equimolar amounts of 1-263-a and 1-263-c, respectively, to obtain compound 1-263 (23.91 g), with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 1047.5732 (theoretical value: 1047.5743). Theoretical elemental content (%) C 80 H 73 N: C, 91.65; H, 7.02; N, 1.34. Measured elemental content (%): C, 91.62; H, 7.03; N, 1.36.

[0249] Synthetic Example 20: Preparation of Compounds 1-268

[0250]

[0251] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-268-a, 1-268-b, and 1-143-c, respectively, to obtain compound 1-268 (21.82 g), with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 875.3565 (theoretical value: 875.3552). Theoretical elemental content (%) C 68 H 45 N: C, 93.22; H, 5.18; N, 1.60. Measured elemental content (%): C, 93.27; H, 5.17; N, 1.56.

[0252] Synthetic Example 21: Preparation of Compounds 1-276

[0253]

[0254] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a and 1-6-c were replaced with equimolar amounts of 1-276-a and 1-276-c, respectively, to obtain compound 1-276 (23.90 g), with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 1061.4946 (theoretical value: 1061.4961). Theoretical elemental content (%) C 82 H 63 N: C, 92.70; H, 5.98; N, 1.32. Measured elemental content (%): C, 92.67; H, 6.01; N, 1.32.

[0255] Synthesis Example 22: Preparation of Compounds 1-283

[0256]

[0257] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-112-a, 1-283-b, and 1-283-c, respectively, to obtain compound 1-283 (22.49 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 913.4631 (theoretical value: 913.4648).

[0258] Theoretical element content (%) C 70 H 59 N: C, 91.96; H, 6.51; N, 1.53. Measured element content (%): C, 91.97; H, 6.49; N, 1.54.

[0259] Synthesis Example 23: Preparation of Compounds 1-286

[0260]

[0261] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-286-a, 1-56-b, and 1-286-c, respectively, to obtain compound 1-286 (22.99 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 945.4347 (theoretical value: 945.4335).

[0262] Theoretical element content (%) C 73 H 55 N: C, 92.66; H, 5.86; N, 1.48. Measured element content (%): C, 92.62; H, 5.85; N, 1.53.

[0263] Synthesis Example 24: Preparation of Compounds 1-298

[0264]

[0265] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-298-a, 1-96-b, and 1-115-c, respectively, to obtain compound 1-298 (23.17 g), with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 989.4980 (theoretical value: 989.4961).

[0266] Theoretical element content (%) C 76 H 63 N: C, 92.17; H, 6.41; N, 1.41. Measured element content (%): C, 92.17; H, 6.42; N, 1.40.

[0267] Synthesis Example 25: Preparation of Compound 1-301

[0268]

[0269] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-191-a, 1-301-b, and 1-301-c, respectively, to obtain compound 1-301 (23.34 g), with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 1009.4661 (theoretical value: 1009.4648). Theoretical elemental content (%) C 78 H 59 N: C, 92.73; H, 5.89; N, 1.39. Measured element content (%): C, 92.70; H, 5.91; N, 1.40.

[0270] Synthetic Example 26: Preparation of Compounds 1-315

[0271]

[0272] Preparation of intermediate 1-315-c:

[0273] Under nitrogen protection, 1-315-f (16.14 g, 63 mmol), 1-315-g (14.49 g, 60 mmol), potassium carbonate (12.44 g, 90 mmol), and Pd(PPh3)4 (0.69 g, 0.60 mmol) were added sequentially to a reaction flask. 400 mL of a toluene / ethanol / water (3:1:1) mixed solvent was added, and the mixture was stirred. The reaction system was heated under reflux for 3.5 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered. The resulting solid was recrystallized from toluene to give intermediate 1-315-c (18.80 g, yield 84%). HPLC analysis showed the solid purity to be ≥99.82%. Mass spectrometry m / z: 372.1633 (theoretical value: 372.1645).

[0274] According to the preparation method in Synthesis Example 1, equimolar amounts of 1-6-a, 1-6-b, and 1-6-c were replaced with equimolar amounts of 1-315-a, 1-283-b, and 1-315-c, respectively, to obtain compound 1-315 (24.93 g), with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 1137.5288 (theoretical value: 1137.5274). Theoretical elemental content (%) C 88 H 67 N: C, 92.84; H, 5.93; N, 1.23. Measured element content (%): C, 92.85; H, 5.96; N, 1.19.

[0275] Synthetic Example 27: Preparation of Compounds 2-19

[0276]

[0277] Preparation of intermediate 2-1-A:

[0278] Under nitrogen protection, intermediates 2-1-a (21.43 g, 90.00 mmol), 2-1-b (17.23 g, 90.00 mmol), Pd(PPh3)4 (1.13 g, 0.98 mmol), and Na2CO3 (13.78 g, 130.00 mmol), along with 300 mL of toluene, 100 mL of ethanol, and 100 mL of water, were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3.5 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 the filter cake with ethyl acetate to obtain intermediate 2-1-A (23.87 g, yield 87%); HPLC purity ≥98.75%. Mass spectrometry m / z: 304.1008 (theoretical value: 304.1019).

[0279] Preparation of intermediate 2-1-B:

[0280] Under nitrogen protection, intermediate 2-1-A (21.34 g, 70.00 mmol), pinacol diboronate (17.78 g, 70.00 mmol), KOAc (15.51 g, 158.00 mmol), Pd(dppf)Cl2 (0.86 g, 1.17 mmol), and 1,4-dioxane (500 mL) were added sequentially to a reaction flask. The mixture was then heated to reflux temperature and reacted for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, and 500 mL of distilled water was added. The mixture was then extracted with ethyl acetate (600 mL × 3). The organic layer was dried over anhydrous MgSO4, and the ethyl acetate was removed by rotary evaporation. The mixture was then recrystallized from toluene:methanol (20:3) and dried to obtain intermediate 2-1-B (23.58 g, 85% yield); HPLC purity ≥99.82%. Mass spectrometry m / z: 396.2278 (theoretical value: 396.2261).

[0281] Preparation of compound 2-19:

[0282] Under nitrogen protection, intermediates 2-1-B (11.89 g, 30.00 mmol), 2-1-c (6.89 g, 30.00 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), tri-tert-butylphosphine (1.44 mL of 0.5 M toluene solution, 0.72 mmol), K2CO3 (6.63 g, 48.00 mmol), and 300 mL of tetrahydrofuran were added sequentially to a reaction flask. The mixture was stirred, and the reaction system was heated under reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 2-19 (11.40 g, yield 82%); HPLC purity ≥99.98%. Mass spectrometry m / z: 463.1948 (theoretical value: 463.1936). Theoretical elemental content (%) C 34 H 25 NO: C, 88.09; H, 5.44; N, 3.02. Measured elemental content (%): C, 88.11; H, 5.45; N, 3.01.

[0283] Synthesis Example 28: Preparation of Compounds 2-26

[0284]

[0285] Preparation of intermediate 2-26-a:

[0286] Under nitrogen protection, 2-26-g (43.55g, 120.00mmol), pinacol diboronate (30.47g, 120.00mmol), Pd(PPh3)4 (1.73g, 1.50mmol), K2CO3 (34.55g, 250.00mmol), and DMF (600mL) were added sequentially to the reaction flask. The mixture was then heated to reflux temperature and reacted for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and 750mL of distilled water was added. The mixture was then extracted with ethyl acetate (750mL × 3). The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The mixture was then recrystallized from toluene:ethanol = 25:1 and dried to obtain intermediate 2-26-a (47.99g, yield 88%); HPLC purity ≥98.68%. Mass spectrometry m / z: 454.3055 (theoretical value: 454.3043).

[0287] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-26-a and 2-26-c, respectively, to obtain compound 2-26 (13.72 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 601.3269 (theoretical value: 601.3283). Theoretical elemental content (%) C 44 H 35 D4NO: C, 87.81; H, 7.20; N, 2.33. Measured elemental content (%): C, 87.78; H, 7.19; N, 2.35.

[0288] Synthetic Example 29: Preparation of Compounds 2-37

[0289]

[0290] According to the preparation method of Synthesis Example 27, equimolar amounts of 2-1-b and 2-1-c were replaced with equimolar amounts of 2-37-b and 2-37-c, respectively, to obtain compound 2-37 (11.07 g); HPLC purity ≥ 99.99%. Mass spectrometry m / z: 444.2125 (theoretical value: 444.2109). Theoretical elemental content (%) C 31 H 16 D6N2O: C, 83.75; H, 6.35; N, 6.30. Measured elemental content (%): C, 83.77; H, 6.34; N, 6.28.

[0291] Synthesis Example 30: Preparation of Compounds 2-40

[0292]

[0293] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-40-a, 2-40-b, and 2-40-c, respectively, to obtain compound 2-40 (13.21 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 564.2189 (theoretical value: 564.2202). Theoretical elemental content (%) C 41 H 28 N₂O: C, 87.21; H, 5.00; N, 4.96. Measured elemental content (%): C, 87.19; H, 4.98; N, 4.97.

[0294] Synthetic Example 31: Preparation of Compounds 2-45

[0295]

[0296] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-45-a, 2-45-b, and 2-45-c, respectively, to obtain compound 2-45 (11.99 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 493.2109 (theoretical value: 493.2092). Theoretical elemental content (%) C 34 H 19 D4N3O: C, 82.73; H, 5.51; N, 8.51. Measured elemental content (%): C, 82.76; H, 5.49; N, 8.48.

[0297] Synthetic Example 32: Preparation of Compounds 2-56

[0298]

[0299] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a were replaced with equimolar amounts of 2-56-a to obtain compound 2-56 (11.73 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 476.2768 (theoretical value: 476.2752). Theoretical elemental content (%) C 34 H 12 D 13 NO: C, 85.67; H, 8.03; N, 2.94. Measured elemental content (%): C, 85.66; H, 8.05; N, 2.97.

[0300] Synthesis Example 33: Preparation of Compounds 2-77

[0301]

[0302] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-77-a and 2-77-c, respectively, to obtain compound 2-77 (13.74 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 594.2678 (theoretical value: 594.2689). Theoretical elemental content (%) C 44 H 22 D7NO: C, 88.86; H, 6.10; N, 2.36. Measured elemental content (%): C, 88.87; H, 6.08; N, 2.34.

[0303] Synthetic Example 34: Preparation of Compounds 2-86

[0304]

[0305] Preparation of intermediate 2-86-B:

[0306] According to the preparation method of Synthesis Example 27, equimolar amounts of 2-1-a were replaced with equimolar amounts of 2-86-a to obtain intermediate 2-86-B (31.33 g, yield 86%), with HPLC purity ≥ 99.72%. Mass spectrometry m / z: 520.2592 (theoretical value: 520.2574).

[0307] Preparation of intermediate 2-86-D:

[0308] Under nitrogen protection, intermediates 2-86-B (26.02 g, 50.00 mmol), 2-86-c (15.43 g, 50.00 mmol), Pd(PPh3)4 (0.62 g, 0.54 mmol), Na2CO3 (7.63 g, 72.00 mmol), 300 mL toluene, 100 mL ethanol, and 100 mL water were added sequentially to a reaction flask. The mixture was stirred and refluxed for 6 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 the filter cake with ethyl acetate to obtain intermediate 2-86-D (25.51 g, yield 82%); HPLC purity ≥98.85%. Mass spectrometry m / z: 621.1845 (theoretical value: 621.1859).

[0309] Preparation of compound 2-86:

[0310] Under nitrogen protection, intermediates 2-86-D (18.66 g, 30.00 mmol), 2-86-d (3.72 g, 30.00 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), tri-tert-butylphosphine (1.44 mL of 0.5 M toluene solution, 0.72 mmol), K2CO3 (6.63 g, 48.00 mmol), and 300 mL of tetrahydrofuran were added sequentially to a reaction flask. The mixture was stirred, and the reaction system was heated under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 2-86 (14.98 g, yield 75%); HPLC purity ≥99.92%. Mass spectrometry m / z: 665.2480 (theoretical value: 665.2467). Theoretical elemental content (%) C 48 H 31 N3O: C, 86.59; H, 4.69; N, 6.31. Measured elemental content (%): C, 86.61; H, 4.70; N, 6.29.

[0311] Synthetic Example 35: Preparation of Compounds 2-91

[0312]

[0313] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-91-a, 2-91-b, and 2-91-c, respectively, to obtain compound 2-91 (13.86 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 599.3021 (theoretical value: 599.3002). Theoretical elemental content (%) C 44 H 17 D12NO: C, 88.11; H, 6.89; N, 2.34. Measured elemental content (%): C, 88.09; H, 6.92; N, 2.36.

[0314] Synthesis Example 36: Preparation of Compound 2-113

[0315]

[0316] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-86-a, 2-113-b, and 2-113-c, respectively, to obtain compound 2-113 (16.00 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 740.2925 (theoretical value: 740.2907). Theoretical elemental content (%) C 56 H 32D3NO: C, 90.78; H, 5.17; N, 1.89. Measured elemental content (%): C, 90.81; H, 5.15; N, 1.90.

[0317] Synthetic Example 37: Preparation of Compound 2-134

[0318]

[0319] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-134-a and 2-134-c, respectively, to obtain compound 2-134 (14.46 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 642.2702 (theoretical value: 642.2719). Theoretical elemental content (%) C 48 H 26 D5NO: C, 89.69; H, 5.64; N, 2.18. Measured elemental content (%): C, 89.71; H, 5.65; N, 2.17.

[0320] Synthetic Example 38: Preparation of Compound 2-155

[0321]

[0322] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-155-a, 2-155-b, and 2-91-c, respectively, to obtain compound 2-155 (13.92 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 610.2064 (theoretical value: 610.2045). Theoretical elemental content (%) C 45 H 26 N₂O: C, 88.50; H, 4.29; N, 4.59. Measured elemental content (%): C, 88.49; H, 4.31; N, 4.62.

[0323] Synthetic Example 39: Preparation of Compound 2-159

[0324]

[0325] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-159-a and 2-159-c, respectively, to obtain compound 2-159 (16.16 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 747.3516 (theoretical value: 747.3501). Theoretical elemental content (%) C 56 H 45NO: C, 89.92; H, 6.06; N, 1.87. Measured elemental content (%): C, 89.93; H, 6.04; N, 1.85.

[0326] Synthetic Example 40: Preparation of Compound 2-175

[0327]

[0328] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-175-a, 2-175-b, and 2-37-c, respectively, to obtain compound 2-175 (17.37 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 838.2970 (theoretical value: 838.2984). Theoretical elemental content (%) C 63 H 38 N₂O: C, 90.19; H, 4.57; N, 3.34. Measured elemental content (%): C, 90.22; H, 4.55; N, 3.36.

[0329] Synthesis Example 41: Preparation of Compound 2-222

[0330]

[0331] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-222-a, 2-222-b, and 2-222-c, respectively, to obtain compound 2-222 (14.44 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 641.2528 (theoretical value: 641.2515). Theoretical elemental content (%) C 47 H 23 D5N2O: C, 87.96; H, 5.18; N, 4.37. Measured elemental content (%): C, 87.98; H, 5.20; N, 4.34.

[0332] Synthesis Example 42: Preparation of Compound 2-252

[0333]

[0334] Preparation of intermediate 2-252-E:

[0335] Under nitrogen protection, intermediates 2-252-e (26.85 g, 150.00 mmol), 2-252-f (46.14 g, 150.00 mmol), Pd(PPh3)4 (1.88 g, 1.63 mmol), Na2CO3 (23.00 g, 217.00 mmol), 300 mL toluene, 100 mL ethanol, and 100 mL water were added sequentially to a reaction flask. The mixture was stirred and 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 the filter cake with ethyl acetate to obtain intermediate 2-252-E (48.32 g, yield 89%); HPLC purity ≥98.59%. Mass spectrometry m / z: 361.1628 (theoretical value: 361.1615).

[0336] Preparation of intermediate 2-252-a:

[0337] Under nitrogen protection, intermediate 2-252-E (43.43 g, 120.00 mmol), pinacol diboronic acid ester (30.47 g, 120.00 mmol), KOAc (26.50 g, 270.00 mmol), Pd(dppf)Cl2 (1.46 g, 2.00 mmol), and 1,4-dioxane (500 mL) were added sequentially to a reaction flask. The mixture was then heated to reflux temperature and reacted for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, and 500 mL of distilled water was added. The mixture was then extracted with ethyl acetate (600 mL × 3). The organic layer was dried over anhydrous MgSO4, and the ethyl acetate was removed by rotary evaporation. The mixture was then recrystallized from toluene:methanol = 40:1 and dried to obtain intermediate 2-1-a (47.34 g, yield 87%); HPLC purity ≥99.67%. Mass spectrometry m / z: 453.2845 (theoretical value: 453.2856).

[0338] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-252-a and 2-252-c, respectively, to obtain compound 2-252 (13.97 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 612.2632 (theoretical value: 612.2617). Theoretical elemental content (%) C 44 H 24 D7NS: C, 86.23; H, 6.25; N, 2.29. Measured elemental content (%): C, 86.24; H, 6.23; N, 2.32.

[0339] Synthetic Example 43: Preparation of Compound 2-281

[0340]

[0341] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a and 2-1-c were replaced with equimolar amounts of 2-281-a and 2-281-c, respectively, to obtain compound 2-281 (13.26 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 566.1803 (theoretical value: 566.1817). Theoretical elemental content (%) C 40 H 26 N2S: C, 84.78; H, 4.62; N, 4.94. Measured elemental content (%): C, 84.81; H, 4.61; N, 4.96.

[0342] Synthesis Example 44: Preparation of Compound 2-301

[0343]

[0344] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-301-a, 2-301-b, and 2-301-c, respectively, to obtain compound 2-301 (15.59 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 711.2948 (theoretical value: 711.2960). Theoretical elemental content (%) C 52 H 41 NS: C, 87.72; H, 5.80; N, 1.97. Measured elemental content (%): C, 87.75; H, 5.78; N, 1.98.

[0345] Synthetic Example 45: Preparation of Compound 2-335

[0346]

[0347] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-155-a, 2-335-b, and 2-335-c, respectively, to obtain compound 2-335 (13.46 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 582.2147 (theoretical value: 582.2130). Theoretical elemental content (%) C 41 H 30 N2S: C, 84.50; H, 5.19; N, 4.81. Measured elemental content (%): C, 84.49; H, 5.22; N, 4.78.

[0348] Synthetic Example 46: Preparation of Compound 2-357

[0349]

[0350] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-357-a, 2-113-b, and 2-357-c, respectively, to obtain compound 2-357 (16.26 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 752.2296 (theoretical value: 752.2286). Theoretical elemental content (%) C 55 H 32 N2S: C, 87.74; H, 4.28; N, 3.72. Measured elemental content (%): C, 87.76; H, 4.30; N, 3.69.

[0351] Synthesis Example 47: Preparation of Compound 2-381

[0352]

[0353] According to the preparation method in Synthesis Example 28, equimolar amounts of 2-26-g, 2-1-b, and 2-26-c were replaced with equimolar amounts of 2-381-g, 2-40-b, and 2-381-c, respectively, to obtain compound 2-381 (16.17 g); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 758.2519 (theoretical value: 758.2504). Theoretical elemental content (%) C 53 H 34 N4S: C, 83.88; H, 4.52; N, 7.38. Measured elemental content (%): C, 83.91; H, 4.49; N, 7.40.

[0354] Synthetic Example 48: Preparation of Compound 2-396

[0355]

[0356] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-396-a, 2-301-b, and 2-396-c, respectively, to obtain compound 2-396 (12.15 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 512.2239 (theoretical value: 512.2222). Theoretical elemental content (%) C 38 H 24 D2N2: C, 89.03; H, 5.50; N, 5.46. Measured elemental content (%): C, 89.05; H, 5.49; N, 5.48.

[0357] Synthesis Example 49: Preparation of Compound 2-425

[0358]

[0359] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-b and 2-1-c were replaced with equimolar amounts of 2-425-b and 2-425-c, respectively, to obtain compound 2-425 (13.17 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 562.2423 (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, 89.67; H, 5.34; N, 5.01.

[0360] Synthesis Example 50: Preparation of Compound 2-463

[0361]

[0362] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-463-a, 2-301-b, and 2-463-c, respectively, to obtain compound 2-463 (14.94 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 672.3367 (theoretical value: 672.3350). Theoretical elemental content (%) C 50 H 24 D 10 N2: C, 89.25; H, 6.59; N, 4.16. Measured elemental content (%): C, 89.28; H, 6.61; N, 4.14.

[0363] Synthetic Example 51: Preparation of Compound 2-492

[0364]

[0365] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-492-a, 2-222-b, and 2-492-c, respectively, to obtain compound 2-492 (14.89 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 661.2532 (theoretical value: 661.2518). Theoretical elemental content (%) C 49 H 31 N3: C, 88.93; H, 4.72; N, 6.35. Measured elemental content (%): C, 88.95; H, 4.69; N, 6.33.

[0366] Synthesis Example 52: Preparation of Compound 2-511

[0367]

[0368] According to the preparation method in Synthesis Example 27, equimolar amounts of 2-1-a, 2-1-b, and 2-1-c were replaced with equimolar amounts of 2-511-a, 2-40-b, and 2-396-c, respectively, to obtain compound 2-511 (16.24 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 751.3838 (theoretical value: 751.3820). Theoretical elemental content (%) C 56 H 21 D 15 N2: C, 89.44; H, 6.83; N, 3.73. Measured elemental content (%): C, 89.46; H, 6.82; N, 3.75.

[0369] [Device Examples 1-30]

[0370] The ITO glass substrate was 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 was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. HI was vacuum-deposited as a hole injection layer with a thickness of 15 nm on an ITO substrate; HT was vacuum-deposited as a hole transport layer with a thickness of 80 nm on the hole injection layer; compounds 1-6 of this invention were vacuum-deposited as electron blocking layers with a thickness of 40 nm on the hole transport layer; RH-1:RD-1 = 96:4 (mass ratio) was vacuum-deposited as a light-emitting layer with a thickness of 20 nm on the electron blocking layer; compounds 2-45 of this invention were vacuum-deposited as hole blocking layers with a thickness of 15 nm on the light-emitting layer; ET 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 70 nm on the electron injection layer.

[0371]

[0372] Device Examples 2-30: Compounds 1-25, 1-56, 1-88, 1-96, 1-112, 1-115, 1-121, 1-148, 1-143, 1-166, 1-191, 1-202, 1-211, 1-216, 1-227, 1-236, 1-255, 1-263, 1-268, 1-276, 1-283, 1-286, 1-298, 1-315, and 1-301 of the present invention were used to replace compounds 1-6 of the present invention in Device Example 1 as electron blocking layer materials, respectively. Compounds 2-134, 2-335, 2-159, 2-113, 2-511, 2-357, 2-91, 2-381, 2-463, 2-281, 2-222, 2-155, 2-37, 2-252, 2-26, 2-492, 2-425, 2-56, 2-175, 2-77, 2-86, 2-301, 2-40, 2-19, and 2-396 were used as the hole-blocking layer material to replace compound 2-45 of the present invention in Device Example 1. Otherwise, organic electroluminescent devices were prepared using the same steps as in Device Example 1.

[0373] Comparative Examples 1-20: Comparative compounds 1, 2, 3, 1-112, 1-202, 1-301, 1-25, 1-121, 1-236, NPB, 1-112, 1-202, and 1-236 were used to replace compounds 1-6 of the present invention in Device Example 1 as electron blocking layer materials, respectively. Compounds 2-91, 2-155, 2-357, and 2-202 were used respectively. Compounds 2-37, 2-335, 2-357, 2-134, 2-492, Comparative Compound 4, Comparative Compound 5, 2-91, 2-335, 2-37, Alq3, 2-37, 2-91, 2-155, and 2-335 were used as the hole-blocking layer material in the alternative compound 2-45 of the present invention in Device Example 1. Otherwise, the organic electroluminescent device was prepared using the same steps as in Device Example 1.

[0374] Comparative Example 21: The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. HI was vacuum-deposited on the ITO substrate as a hole injection layer with a thickness of 15 nm; HT was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 80 nm; RH-1:RD-1 = 96:4 (mass ratio) was vacuum-deposited on the hole transport layer as a light-emitting layer with a thickness of 20 nm; compound 2-37 of this invention was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 15 nm; ET was vacuum-deposited on the hole blocking layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 70 nm.

[0375] Comparative Examples 22-24: Compound 2-91, Compound 2-155, and Compound 2-335 of the present invention were used to replace Compound 2-37 of the present invention in Comparative Example 21 as electron blocking layer materials, respectively. Otherwise, organic electroluminescent devices were prepared using the same steps as in Comparative Example 21.

[0376] Comparative Example 25: The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. HI was vacuum-deposited on the ITO substrate as a hole injection layer with a thickness of 15 nm; HT was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 80 nm; compounds 1-25 of this invention were vacuum-deposited on the hole transport layer as an electron blocking layer with a thickness of 40 nm; RH-1:RD-1 = 96:4 (mass ratio) was vacuum-deposited on the electron blocking layer as a light-emitting layer with a thickness of 20 nm; ET was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 70 nm.

[0377] Comparative Examples 26-28: Compounds 1-112, 1-202, and 1-301 of the present invention were used to replace Compound 1-25 of the present invention in Comparative Example 25 as hole blocking layer materials, respectively. Otherwise, organic electroluminescent devices were prepared using the same steps as in Comparative Example 25.

[0378] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0379] The luminescence characteristics of the obtained organic electroluminescent devices are shown in Table 1. Table 1 shows the luminescence characteristics of the organic electroluminescent devices prepared by the compounds prepared in the embodiments of the invention and the comparative materials.

[0380] Table 1. Luminescence characteristics test of organic electroluminescent devices

[0381]

[0382]

[0383]

[0384] As can be seen from the results in Table 1, compared with comparative examples 1 to 28, device examples 1 to 26 have higher luminous efficiency and longer device lifetime.

[0385] 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, comprising an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, characterized in that, The hole transport region includes the structure shown in Equation 1. In Formula 1, Ar1 and Ar2, whether the same or different, are selected from the structures shown below. The same or different R1 to R4 are selected from any one of hydrogen, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, and substituted or unsubstituted C6 to C18 aryl; The same or different a1 is selected from 0, 1, 2 or 3; the same or different a2 is selected from 0, 1, 2, 3 or 4; the same or different a3 and a4 are selected from 0, 1, 2, 3, 4 or 5; when there are two or more R1, the two or more R1 are the same or different from each other, or adjacent R1 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R2, the two or more R2 are the same or different from each other, or adjacent R2 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R3, the two or more R3 are the same or different from each other, or adjacent R3 are connected to each other to form a substituted or unsubstituted ring; when there are two or more R4, the two or more R4 are the same or different from each other, or adjacent R4 are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from any of the structures shown below. The same or different R5 is selected from any one of hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C18 aryl; The same or different b1 is selected from 0, 1, 2, 3, 4 or 5; the same or different b2 is selected from 0, 1, 2, 3 or 4; the same or different b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R5, the two or more R5 are the same or different from each other; The L1 to L3 are the same or different and are selected from any one of the single-bonded, substituted or unsubstituted C6 to C18 aryl groups; The electron transport region includes the structure shown in Equation 2. A-L b -L c -L d -B Formula 2 A is selected from any of the structures shown below. The x that is the same or different is selected from CR6 or N; The Ra, Rb, Rc, and R6 are the same or different and are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The La is selected from any one of single-bonded, substituted or unsubstituted C6 to C18 aryl groups; The B is selected from the structure shown below. The z that are the same or different are selected from CR7 or N; X1 is selected from any one of O, S, and NR8; The same or different R7 and Rd are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The R8s, whether identical or different, are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups. The L b L c L d The same or different is selected from any one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, and substituted or unsubstituted terphenylene.

2. The organic electroluminescent device according to claim 1, characterized in that, The Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below. The R9, whether identical or different, is selected from any one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, tolyl, tert-butylphenyl, adamantylphenyl, biphenyl, and naphthyl; The same or different c1 is selected from 0, 1, 2, 3, 4 or 5; the same or different c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R9, the two or more R9 are the same or different from each other.

3. An organic electroluminescent device according to claim 1, characterized in that, The Ar3, whether identical or different, is selected from any of the structures shown below.

4. An organic electroluminescent device according to claim 1, characterized in that, The L1 to L3, whether identical or different, are selected from single bonds or any of the structures shown below. The R 12 The same or different from any one selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl; The same or different values ​​of e1 are selected from 0, 1, 2, 3, or 4; the same or different values ​​of e2 are selected from 0, 1, 2, or 3; the same or different values ​​of e3 are selected from 0, 1, 2, 3, 4, or 5; the same or different values ​​of e4 are selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... 12 At that time, two or more R 12 They may be the same as or different from each other.

5. An organic electroluminescent device according to claim 1, characterized in that, The structure in Formula 1 is selected from any one of the structures shown below.

6. An organic electroluminescent device according to claim 1, characterized in that, The structure described in Formula 2 is selected from any one of the structures shown in Formulas 2-1 to 2-6 below. The x that is the same or different is selected from CR6 or N; The R6 is the same as or different from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted norbornel, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, and substituted or unsubstituted imidazolyl.

7. An organic electroluminescent device according to claim 1, characterized in that, A is selected from any of the structures shown below. The x that is the same or different is selected from CR6 or N; The R6, R 10 The same or different are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; The R6 is either unsubstituted or substituted with one or more substituents, wherein the substituents are the same or different and are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents are the same or different from each other; The R 10 It is either unsubstituted or substituted with one or more substituents, wherein the same or different substituents are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents are the same or different from each other; The values ​​of d1 (same or different) are selected from 0, 1, 2, 3, 4, or 5; the values ​​of d2 (same or different) are selected from 0, 1, 2, 3, or 4; the values ​​of d3 (same or different) are selected from 0, 1, 2, 3, 4, 5, 6, or 7; the values ​​of d4 (same or different) are selected from 0, 1, 2, 3, 4, 5, or 6; the values ​​of d5 (same or different) are selected from 0, 1, 2, 3, 4, or 5; the values ​​of d6 (same or different) are selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the values ​​of d7 (same or different) are selected from 0, 1, or 2; when there are two or more R... 10 At that time, two or more R 10 They may be the same as or different from each other.

8. An organic electroluminescent device according to claim 1, characterized in that, The B is selected from any of the structures shown below. X1 is selected from any one of O, S, and NR8; The R8 group, whether identical or different, is selected from any one of methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, tolyl, deuterated phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl. The R7, whether identical or different, is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornelalkyl, adamantylalkyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl. The R7 is either unsubstituted or substituted with one or more substituents, wherein the substituents are the same or different and are selected from any one of deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, norbornel, adamantyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl; when two or more substituents are present, the two or more substituents are the same or different from each other; The m1 that is the same or different is selected from 0, 1, 2, 3 or 4; the m2 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 that is the same or different is selected from 0, 1, 2 or 3; the m5 that is the same or different is selected from 0, 1, 2, 3, 4 or 5; the m6 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m7 that is the same or different is selected from 0, 1 or 2; the m8 that is the same or different is selected from 0 or 1; when there are two or more R7, the two or more R7 are the same or different from each other.

9. An organic electroluminescent device according to claim 1, characterized in that, The L b L c L d The same or different ones are selected from single bonds or any of the structures shown below. The R 11 The same or different are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl; The n1 that is the same or different is selected from 0, 1, 2, 3 or 4; the n2 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R 11 At that time, two or more R 11 They may be the same as or different from each other.

10. An organic electroluminescent device according to claim 1, characterized in that, The structure in Equation 2 is selected from any one of the structures shown below.

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