An organic electroluminescent device

CN116234343BActive Publication Date: 2026-09-11CHANGCHUN HYPERIONS TECH CO LTD
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Patent Information

Application Number
CN202310267117.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-03-17
Publication Date
2026-09-11
Estimated Expiration
2043-03-17

AI Technical Summary

Technical Problem

[0004]鉴于目前的器件存在驱动电压较高,以及能级匹配问题导致的发光性能差、寿命短等缺点,因此亟待开发一种能级匹配好、发光性能优良的有机电致发光器件

Benefits of technology

[0014] This invention applies the first compound shown in formula (I) and the second compound shown in formula (II) simultaneously to the hole transport region of a device. In particular, when the two organic functional layers to which they are applied are adjacent (for example, the first compound is used as a hole transport layer and the second compound is used as a light-emitting auxiliary layer, and the two layers are adjacent), the two organic functional layers have a good energy level matching degree and interface transport capability. On the one hand, this improves the charge transport efficiency and reduces the probability of excitons in the light-emitting layer migrating to the interface between the light-emitting layer and the hole transport region, effectively avoiding interface luminescence and preventing the accelerated aging of the organic functional layer material due to factors such as interface luminescence, thereby improving the luminescence efficiency of the device, extending the device's lifespan, and reducing the device's driving voltage. On the other hand, the first compound and the second compound described in this invention each have good thermal and chemical stability, and when the two organic functional layers to which they are applied are adjacent, the contact surface between the two organic functional layers has excellent adhesion and stability, improving the device's stability and further extending the device's lifespan.

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Abstract

The application belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescence device. The application uses a first compound shown in formula (I) as a hole transport layer, uses a second compound shown in formula (II) as a light-emitting auxiliary layer, and the two layers are adjacent, and the two organic functional layers have good energy level matching degree and interface transmission capacity. On the one hand, the charge transmission efficiency is improved, the probability of exciton migration in the light-emitting layer to the interface between the light-emitting layer and the hole transport region is reduced, the interface light emission is effectively avoided, the light-emitting efficiency of the device is improved, the service life of the device is prolonged, and the driving voltage of the device is reduced. On the other hand, the stability of the first compound and the second compound is good respectively, when the two organic functional layers of the two compounds are adjacent, the contact surface between the two organic functional layers has excellent fitting degree and smoothness, and the service life of the device is further prolonged.
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Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have advantages such as light weight, small size, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They can meet consumers' new demands for display technology and have a promising application prospect in the fields of lighting and display.

[0003] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes, a cathode and an anode, containing a luminescent material. When a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode, respectively, recombine in the emissive layer to form excitons, releasing energy. These excitons migrate, transferring energy to the guest material. Electrons in the guest material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons migrate back to the stable ground state, releasing energy as light, producing the luminescence phenomenon. To improve the performance of OLED devices, such as driving voltage, luminous efficiency, color purity, and lifespan, additional organic functional layers are added between the anode and the emissive layer, and between the cathode and the emissive layer. Generally, the organic functional layer between the anode and the emissive layer acts as a hole transport region, while the organic functional layer between the cathode and the emissive layer acts as an electron transport region. The hole transport region includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer. The electron transport region includes one or more of the following: an electron injection layer, an electron transport layer, and a hole blocking layer. To further improve the luminous efficiency and lifespan of the device, a capping layer is often provided on the outer side of the electrode on the light-emitting side.

[0004] Given the shortcomings of current devices, such as high driving voltage and poor luminescence performance and short lifetime caused by energy level matching problems, there is an urgent need to develop an organic electroluminescent device with good energy level matching and excellent luminescence performance. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides an organic electroluminescent device with low driving voltage, high luminous efficiency, and long lifespan, comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region includes a hole transport layer and a light-emitting auxiliary layer. The hole transport layer contains a first compound represented by formula (I), and the light-emitting auxiliary layer contains a second compound represented by formula (II).

[0006]

[0007] Wherein, L is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring fused with a C3-C6 aliphatic ring;

[0008] The L1 to L4 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a C3 to C6 aliphatic ring;

[0009] The Ar1 to Ar4, Ar 101 ~Ar 106 The group is independently selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring fused with a substituted or unsubstituted C3-C6 aliphatic ring, and at least one of the following Ar1-Ar4 is selected from one of the following: a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthraceneyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylene group;

[0010] The L mentioned 101 ~L 109 It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C6 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene.

[0011] The a mentioned 101 Choose from 0, 1, 2, or 3;

[0012] The R mentioned 101Each time it appears, it is selected from the same or different groups selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C30 aryl group, and a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C6 aliphatic ring.

[0013] Beneficial effects:

[0014] This invention applies the first compound shown in formula (I) and the second compound shown in formula (II) simultaneously to the hole transport region of a device. In particular, when the two organic functional layers to which they are applied are adjacent (for example, the first compound is used as a hole transport layer and the second compound is used as a light-emitting auxiliary layer, and the two layers are adjacent), the two organic functional layers have a good energy level matching degree and interface transport capability. On the one hand, this improves the charge transport efficiency and reduces the probability of excitons in the light-emitting layer migrating to the interface between the light-emitting layer and the hole transport region, effectively avoiding interface luminescence and preventing the accelerated aging of the organic functional layer material due to factors such as interface luminescence, thereby improving the luminescence efficiency of the device, extending the device's lifespan, and reducing the device's driving voltage. On the other hand, the first compound and the second compound described in this invention each have good thermal and chemical stability, and when the two organic functional layers to which they are applied are adjacent, the contact surface between the two organic functional layers has excellent adhesion and stability, improving the device's stability and further extending the device's lifespan. Detailed Implementation

[0015] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0016] 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.

[0017] The halogen atoms mentioned in this invention refer to fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0018] The alkyl group described in this invention refers to a hydrocarbon 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 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0019] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0020] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentenyl or cyclohexenyl.

[0021] The cycloalkynyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkynyl molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropynyl, cyclobutynyl, cyclopentynyl, cyclohexynyl, cycloheptynyl, etc., but are not limited thereto. The aforementioned cycloalkyl group is preferably cyclopentynyl or cyclohexynyl.

[0022] The heterocyclic group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. The heteroatom includes nitrogen, oxygen, sulfur, silicon, etc., preferably nitrogen, oxygen, or sulfur. It preferably contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It preferably has 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic group is preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0023] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0024] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0025] The term "group formed by the fusion of aromatic and aliphatic rings" as used in this invention refers to the general term for a monovalent group formed by the fusion of an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) and the removal of one hydrogen atom. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzocyclopropyl, benzocyclobutyl, indenyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentenyl, naphthocyclohexyl, etc., but are not limited thereto.

[0026] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0027] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0028] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0029] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0030] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: halogen atom, deuterium atom, tritium atom, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C1-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl ... C30 cycloalkynyl, substituted or unsubstituted C3-C30 heterocyclic group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium atom, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocyclic group, C6-C30 The aryl, C3-C30 heteroaryl, and silyl groups, when substituted with multiple substituents, have the multiple substituents being the same or different from each other; preferably, this means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, norbornene. The following substances are used: methyl, methoxy, ethoxy, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, where, when substituted with multiple substituents, the multiple substituents may be the same or different from each other.

[0031] The "substituents containing deuterium atoms" described in this invention include: deuterated C1-C12 alkyl groups; deuterated C3-C10 cycloalkyl groups; deuterated C3-C10 cycloalkenyl groups; deuterated C6-C30 aryl groups; deuterated C2-C30 heteroaryl groups; C6-C30 aryl groups substituted with one or more of deuterium, deuterated C1-C12 alkyl groups, deuterated C6-C12 aryl groups, and deuterated C2-C30 heteroaryl groups; and C2-C30 heteroaryl groups substituted with one or more of deuterium, deuterated C1-C12 alkyl groups, deuterated C6-C12 aryl groups, and deuterated C2-C30 heteroaryl groups. For example, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclopropane, deuterated cyclobutane, deuterated cyclopentane, deuterated cyclohexane, deuterated adamantane, deuterated norbornel, deuterated cyclopropenyl, deuterated cyclobutenyl, deuterated cyclopentenyl, deuterated cyclohexenyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl. Deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated spirodifluorenyl, deuterated spiro-cyclopentane-fluorenyl, deuterated spiro-cyclohexane-fluorenyl, deuterated spiro-adamantane-fluorenyl, deuterated 9-methyl-9-phenylfluorenyl, deuterated dibenzofuran, deuterated dibenzothiophene, deuterated N-phenylcarbazole, etc.

[0032] In the instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the group / fragment to which it is attached. For example express And so on.

[0033] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0034] The linked ring structure described in this invention refers to the interconnection of various groups by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following example:

[0035]

[0036]

[0037] In this invention, the bonded ring can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. It can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring. Examples may include benzene, naphthalene, indene, fluorene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0038] Furthermore, two groups attached to the same nitrogen atom can be linked together to form a ring, as shown in the following example:

[0039]

[0040] In this invention, the ring formed by two groups connected to the same nitrogen atom can be carbazole, or a group in which one or two benzene rings of carbazole are fused with benzene rings or naphthalene rings.

[0041] This invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region includes a hole transport layer and a light-emitting auxiliary layer. The hole transport layer contains a first compound represented by formula (I), and the light-emitting auxiliary layer contains a second compound represented by formula (II).

[0042]

[0043] Wherein, L is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring fused with a C3-C6 aliphatic ring;

[0044] The L1 to L4 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a C3 to C6 aliphatic ring;

[0045] The Ar1 to Ar4, Ar 101 ~Ar 106 The group is independently selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring fused with a substituted or unsubstituted C3-C6 aliphatic ring, and at least one of the following Ar1-Ar4 is selected from one of the following: a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthraceneyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylene group;

[0046] The L mentioned 101 ~L 109 It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C6 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene.

[0047] The a mentioned 101 Choose from 0, 1, 2, or 3;

[0048] The R mentioned 101 Each time it appears, it is selected from the same or different groups selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C30 aryl group, and a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C6 aliphatic ring.

[0049] Preferably, the substituent in "substituted or unsubstituted" is selected from deuterium atom; halogen atom; cyano group; C1-C12 straight-chain or branched alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, and deuterated biphenyl group; A C3-C12 cycloalkyl group substituted or unsubstituted with one or more of the groups consisting of deuterated biphenyl groups; a C3-C12 cycloalkenyl group substituted or unsubstituted with one or more of the groups consisting of deuterium, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; a C3-C12 cycloalkenyl group substituted or unsubstituted with one or more of the groups consisting of deuterium, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl The group consisting of one or more substituted or unsubstituted C6-C30 aryl groups; the group consisting of one or more substituted or unsubstituted C2-C30 heteroaryl groups from the group consisting of a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; the group consisting of one or more substituted or unsubstituted C6-C30 aryl groups from the group consisting of a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group. A group consisting of one or more substituted or unsubstituted C6-C30 aromatic rings fused with C3-C7 aliphatic rings; a silyl group consisting of one or more substituted or unsubstituted silyl groups from the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl, wherein the substituents are one or more, and when there are multiple substituents, the multiple substituents are the same or different, and when there are multiple substituents, two adjacent substituents can be linked to form substituted or unsubstituted saturated or unsaturated C3-C6 carbon rings.

[0050] Preferably, the substituents in "substituted or unsubstituted" are selected from the group consisting of deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano; methyl; deuterated methyl; ethyl; deuterated ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; deuterated tert-butyl; cyclopropane groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclopropane groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, isopropyl, n-butyl, etc. Cyclobutyl groups substituted or unsubstituted with one or more of the following groups: tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclobutyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclopentyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, and deuterated tert-butyl. Cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of alkyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclopropenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclopropenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated... Cyclobutenyl groups substituted or unsubstituted with one or more of the group consisting of biphenyl; cyclopentenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclohexenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl.Adamantyl alkyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; norbornene alkyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; A phenyl group substituted or unsubstituted with one or more of the following groups: methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl Anthracene group substituted or unsubstituted with one or more of the group consisting of propyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; phenanthryl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; phenanthryl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterium. Triphenylene oxide substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; fluorenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl;A dibenzothiophene group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; A carbazoyl group substituted or unsubstituted with one or more of the group consisting of trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; or a carbazoyl group substituted or unsubstituted with one of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. The following are substituted or unsubstituted indanyl groups: a tetrahydronaphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a tetrahydronaphthyl group substituted or unsubstituted with one of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, n-butyl. The silyl group is selected from the group consisting of one or more substituted or unsubstituted alkyl groups, including methyl, tert-butyl, deuterated methyl, trifluoromethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. The substituted group can be one or more, and when there are multiple substituted groups, the multiple substituted groups may be the same or different. When there are multiple substituted groups, adjacent substituted groups can be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring.

[0051] Preferably, the L is selected from one of the following structures:

[0052]

[0053] Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0054] The R mentioned11 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C6 aliphatic ring;

[0055] The R mentioned 12 R 13 Independently selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or the aforementioned R. 12 With R 13 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C10 carbon rings.

[0056] Preferably, the R 11 Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano group; methyl group; ethyl group; n-propyl group; isopropyl group; n-butyl group; tert-butyl group; deuterated methyl group; deuterated ethyl group; deuterated isopropyl group; deuterated tert-butyl group; trifluoromethyl group; cyclopropane group; cyclobutane group; cyclopentane group; cyclohexane group; cycloheptane group; cyclopentenyl group; cyclohexenyl group; adamantyl group; norbornel group; deuterated group. A phenyl group consisting of one or more substituted or unsubstituted atoms from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel; a phenyl group substituted or unsubstituted with one atom; A naphthyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; a biphenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl.

[0057] Preferably, the R 12 R 13 The phenyl group independently selected from the group consisting of methyl; ethyl; isopropyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; phenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; phenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl A naphthyl group substituted or unsubstituted with one or more of the group consisting of alkyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; or a biphenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl, or the aforementioned R. 12 With R 13 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C10 carbon rings.

[0058] Preferably, the L is selected from one of the following structures:

[0059]

[0060]

[0061] Preferably, the L is selected from one of the following structures:

[0062]

[0063] Preferably, L1 to L4 are independently selected from a single bond or one of the following structures:

[0064]

[0065] Wherein, the a 11 b 11 c 11 d 11 e 11 R 11 R12 R 13 All are as described in this invention.

[0066] Preferably, L1 to L4 are independently selected from a single bond or one of the following structures:

[0067]

[0068] Preferably, L1 to L4 are independently selected from a single bond or one of the following structures:

[0069]

[0070] Preferably, the Ar1 to Ar4 and Ar 101 ~Ar 106 Independently selected from one of the structures shown below, and at least one of Ar1 to Ar4 is selected from a C6 to C30 aryl group or a group formed by the fusion of a C6 to C30 aromatic ring and a C3 to C6 aliphatic ring, substituted or unsubstituted, from the group consisting of one or more of the substituents described below: substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene.

[0071]

[0072] Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0073] The R mentioned 21 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by the fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or two adjacent R groups. 21 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C6 carbon rings.

[0074] Preferably, the R 21Each time it appears, it is selected, either identically or differently, from the group consisting of hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; trifluoromethyl; cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; cyclopropane, cyclobutane, cyclopentyl, cyclohexenyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; Cyclobutyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, norbornel group; cyclobutane groups substituted or unsubstituted with one of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group. Cyclopentyl groups substituted or unsubstituted with one or more of the group consisting of alkyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and deuterium groups. Cycloheptyl groups substituted or unsubstituted with one or more of the following groups: methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; cyclopentenyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl.A cyclohexenyl group substituted or unsubstituted by one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; a cyclohexenyl group substituted or unsubstituted by one of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl. Adamantyl group substituted or unsubstituted with one or more of the group consisting of cyclohexenyl, adamantyl, and norbornyl; norbornyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; norbornyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated ...tert-butyl, A phenyl group substituted or unsubstituted with one or more of the following groups: butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, and n-propyl. Anthracene group substituted or unsubstituted with one or more of the following groups: cyclopropane, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; phenanthrene group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl;A biphenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; One or more substituted or unsubstituted triphenyl groups composed of the following groups: fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornel group.

[0075] Preferably, the Ar1 to Ar4 and Ar 101 ~Ar 106 Independently selected from one of the structures shown below, and at least one of Ar1 to Ar4 is selected from a C6 to C30 aryl group or a group formed by the fusion of a C6 to C30 aromatic ring and a C3 to C6 aliphatic ring, substituted or unsubstituted, from the group consisting of one or more of the substituents described below: substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene.

[0076]

[0077]

[0078]

[0079] Preferably, at least one of Ar1 to Ar4 is selected from one of the following structures:

[0080]

[0081] Wherein, the a 22 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above. 22 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 22 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 22 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e mentioned 22 Each time it appears, it is selected from 1, 2, 3 or 4, either the same or different;

[0082] The R mentioned22 Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; deuterated ethyl; isopropyl; deuterated isopropyl; tert-butyl; deuterated tert-butyl; adamantyl group substituted or unsubstituted with one or more of deuterium atom, methyl, ethyl, isopropyl, and tert-butyl; norbornyl group substituted or unsubstituted with one or more of deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl. The following structures contain an anthracene group substituted or unsubstituted with one or more of the following: a deuterium atom, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, and norbornyl group; a phenanthrene group substituted or unsubstituted with one or more of the following: a deuterium atom, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, and norbornyl group; and a triphenylene group substituted or unsubstituted with one or more of the following: a deuterium atom, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, and norbornyl group, wherein each of the above structures contains at least one R. 22 The following are selected from naphthyl groups substituted or unsubstituted with one or more of the following: deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; anthraceneyl groups substituted or unsubstituted with one or more of the following: deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; phenanthrene groups substituted or unsubstituted with one or more of the following: deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; and triphenylene groups substituted or unsubstituted with one or more of the following: deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl.

[0083] The R mentioned 23Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; halogen atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; deuterated ethyl; isopropyl; deuterated isopropyl; tert-butyl; deuterated tert-butyl; adamantyl alkyl group substituted or unsubstituted with one or more of deuterium atom, methyl, ethyl, isopropyl, and tert-butyl; norbornyl alkyl group substituted or unsubstituted with one or more of deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl alkyl, and norbornyl alkyl. A substituted or unsubstituted naphthyl group; an anthracene group substituted or unsubstituted by one or more of a deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, or norbornyl; a phenanthrene group substituted or unsubstituted by one or more of a deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, or norbornyl; or a triphenylene group substituted or unsubstituted by one or more of a deuterium atom, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, or norbornyl.

[0084] Preferably, at least one of Ar1 to Ar4 is selected from one of the following structures:

[0085]

[0086]

[0087] Wherein, the a 24 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 24 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the e 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the g mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, either the same or different.

[0088] The R mentioned 24 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group.

[0089] Preferably, at least one of Ar1 to Ar4 is selected from one of the following structures:

[0090]

[0091]

[0092] Preferably, "at least one of Ar1 to Ar4" includes one, two, three or four of Ar1 to Ar4, specifically including: Ar1; Ar2; Ar3; Ar4; Ar1 ​​and Ar2; Ar1 ​​and Ar3; Ar1 ​​and Ar4; Ar2 and Ar3; Ar2 and Ar4; Ar3 and Ar4; Ar1, Ar2 and Ar3; Ar1, Ar2 and Ar4; Ar2, Ar3 and Ar4; Ar1, Ar2, Ar3 and Ar4.

[0093] Preferably, the L 101 ~L 109 Independently selected from a single bond or one of the following structures:

[0094]

[0095] Wherein, the a 11 b 11 c 11 d 11 e 11 R 11 R 12 R 13 All as described in this invention;

[0096] The R mentioned 14 It is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, and substituted or unsubstituted phenanthryl.

[0097] Preferably, the R 14A phenyl group selected from the group consisting of one or more substituted or unsubstituted phenyl groups, including deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, naphthyl, anthracene, and phenanthrene groups; a phenyl group substituted or unsubstituted with one of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, etc. The naphthyl group is substituted or unsubstituted with one or more of the group consisting of butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, and naphthyl; substituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, and naphthyl. Or unsubstituted anthracene group; substituted or unsubstituted phenanthrene group substituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; substituted or unsubstituted phenanthrene group substituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl. A biphenyl group substituted or unsubstituted with one or more of the following groups: trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantane, and norbornyl; or a triphenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantane, and norbornyl.

[0098] Preferably, the L 101 ~L 109 Independently selected from a single bond or one of the following structures:

[0099]

[0100] Preferably, the L 101 ~L 109 Independently selected from a single bond or one of the following structures:

[0101]

[0102]

[0103] Preferably, the R 101 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted sec-butyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopropane group, substituted or unsubstituted cyclobutane group, substituted or unsubstituted cyclopentane group, substituted or unsubstituted cyclohexane group, substituted or unsubstituted cycloheptane group, substituted or unsubstituted cyclopropene group, substituted or unsubstituted cyclobutenyl group, substituted or unsubstituted cyclopentenyl group, substituted or unsubstituted cyclohexenyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, and substituted or unsubstituted naphthyl group.

[0104] Preferably, the R 101Each time it appears, it is selected, either identically or differently, from the group consisting of hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; trifluoromethyl; cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; cyclopropane, cyclobutane, cyclopentyl, cyclohexenyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; Cyclobutyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, norbornel group; cyclobutane groups substituted or unsubstituted with one of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group. Cyclopentyl groups substituted or unsubstituted with one or more of the group consisting of alkyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and deuterium groups. Cycloheptyl groups substituted or unsubstituted with one or more of the group consisting of methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; adamantyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl.The norbornyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; A phenyl group substituted or unsubstituted with one or more of the group consisting of fluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl.

[0105] Preferably, the R 101 Each time it appears, it is selected, either identically or differently, from one of the following structures: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, or the structure shown below:

[0106]

[0107] Preferably, the first compound is selected from the structures shown in formulas (IA) to (IH):

[0108]

[0109]

[0110] Wherein, L, L2 to L4 are all as described in this invention;

[0111] The a mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 31 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 31 Each time it appears, it is selected from 0, 1, or 2, either the same or different.

[0112] The R mentioned 31Each time it appears, it is selected from one of the following, either identically or differently: hydrogen atom, deuterium atom, methyl, isopropyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, methyl-substituted norbornyl, ethyl-substituted adamantyl, ethyl-substituted norbornyl, isopropyl-substituted adamantyl, isopropyl-substituted norbornyl, tert-butyl-substituted adamantyl, and tert-butyl-substituted norbornyl.

[0113] The Ar2 to Ar4 are independently selected from one of the following structures:

[0114]

[0115] The a mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 41 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the d mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the e 41 Each time it appears, it is selected from 0, 1, 2, 3 or 4, either the same or different.

[0116] The R mentioned 41 Each time it appears, it is selected from one of the following, either identically or differently: hydrogen atom, deuterium atom, methyl, isopropyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, methyl-substituted norbornyl, ethyl-substituted adamantyl, ethyl-substituted norbornyl, isopropyl-substituted adamantyl, isopropyl-substituted norbornyl, tert-butyl-substituted adamantyl, and tert-butyl-substituted norbornyl.

[0117] The L1' to L4' are independently selected from one of the following: a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a C3 to C6 aliphatic ring, or a divalent group.

[0118] Preferably, L1' to L4' are independently selected from one of the following structures:

[0119]

[0120] Wherein, the a11 b 11 c 11 d 11 e 11 R 11 R 12 R 13 All are as described in this invention.

[0121] Preferably, L1' to L4' are independently selected from one of the following structures:

[0122]

[0123] Preferably, L1' to L4' are independently selected from one of the following structures:

[0124]

[0125]

[0126] Preferably, the Ar2 to Ar4 are independently selected from one of the following structures:

[0127]

[0128]

[0129]

[0130] Preferably, the first compound is selected from the structures shown in formulas (IJ) to (IT):

[0131]

[0132] Wherein, L1~L4 and Ar1~Ar4 are as described in this invention;

[0133] The a mentioned 51 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 51 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 51 Each time it appears, it is selected from 0, 1, or 2, either the same or different.

[0134] The R mentioned 51 With the aforementioned R 31 Same definition;

[0135] The R mentioned 52 R 53Independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, tert-butyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, or R 52 With R 53 They connect to form substituted or unsubstituted saturated or unsaturated C5-C6 carbon rings.

[0136] Preferably, the second compound is selected from the structure shown in formula (II-A) or formula (II-B):

[0137]

[0138] Wherein, the L 101 ~L 109 Ar 101 ~Ar 106 All as described in this invention;

[0139] The R mentioned 101 Each time it appears, it is selected from hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C12 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, and at least one R. 101 It is not a hydrogen atom.

[0140] Preferably, the second compound is selected from the structure shown in formula (II-C) or formula (II-D):

[0141]

[0142] Wherein, the L 101 ~L 109 Ar 101 ~Ar 106 All as described in this invention;

[0143] The R mentioned 101 Each time it appears, it is selected, either identically or differently, from one of the following structures: hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, or the structure shown below, and at least one R. 101 Not a hydrogen atom:

[0144]

[0145] Preferably, the first compound is selected from one of the following structures:

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] Preferably, the second compound is selected from one of the following compounds:

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] The above only lists some specific structural forms of the first compound shown in formula (I) and the second compound shown in formula (II). However, the present invention is not limited to these listed chemical structures. Any chemical structures based on formula (I) and formula (II) with substituents as defined above should be included.

[0174] The first compound represented by formula (I) of this invention can be prepared by the following synthetic route:

[0175] Synthesis Route 1:

[0176]

[0177] Wherein, L, L1~L4, Ar1~Ar4 are as described in this invention;

[0178] Z1 and Z2 are independently selected from chlorine atoms, bromine atoms, or iodine atoms.

[0179] In synthetic route one, compound (aa) can be reacted with aromatic amine compounds (bb) and (cc) in one or two steps via the Buchwald–Hartwig reaction to obtain the first compound shown in formula (I).

[0180] The second compound represented by formula (II) of this invention can be prepared by any of the following synthetic routes:

[0181] Synthesis Route 2:

[0182]

[0183] Synthesis Route 3:

[0184]

[0185] Combining synthesis route two with synthesis route three yields the following synthesis route:

[0186] Synthesis Route 4:

[0187]

[0188] Synthesis Route 5:

[0189]

[0190] Wherein, the L 101 ~L 109 a 101 R 101 Ar 101 ~Ar 106All are as described in this invention; X1 to X3 are independently selected from chlorine atoms, bromine atoms, or iodine atoms; when L 101 When selected from a single bond, Y1 is selected from hydrogen; when L... 101 When Y1 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene group, Y1 is selected from... When L 102 When selected from a single bond, Y2 is selected from hydrogen; when L... 102 When Y2 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene group, Y2 is selected from... When L 103 When selected from a single bond, Y3 is selected from hydrogen; when L... 103 When Y3 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene group, Y3 is selected from...

[0191] In synthetic route two, compound (A) can be reacted with aromatic amine compounds (B), (C), and (D) in one or more steps via a Buchwald–Hartwig reaction or a Suzuki coupling reaction to obtain the compound shown in formula (II).

[0192] In synthetic route three, compound (E) can react with compounds (F), (G), and (H) in one or more steps via the Buchwald–Hartwig reaction to obtain the compound shown in formula (II).

[0193] In synthetic route four, compound (J) can react with compounds (F) and (G) in one or two steps via a Buchwald-Hartwig reaction to obtain intermediate (K); then, intermediate (K) reacts with compound (D) via a Buchwald-Hartwig reaction or a Suzuki coupling reaction to obtain the compound shown in formula (II).

[0194] In synthetic route five, compound (L) reacts with compound (B) via a Buchwald–Hartwig reaction or a Suzuki coupling reaction to give intermediate (M); then, intermediate (M) reacts with compounds (G) and (H) via a one-step or two-step Buchwald–Hartwig reaction to give the compound shown in formula (II).

[0195] All the above reaction routes employ commonly used reaction types in organic synthesis. There are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.), and conventional methods and operations can be used. The above preparation methods utilize readily available raw materials, have simple processes, and yield excellent results. The first compound shown in formula (I) and the second compound shown in formula (II) provided by this invention can also be synthesized using other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0196] Preferably, the hole transport layer is located between the anode and the light-emitting layer, and the light-emitting auxiliary layer is located between the light-emitting layer and the hole transport layer.

[0197] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole transport layer is located between the anode and the light-emitting layer, the light-emitting auxiliary layer is located between the light-emitting layer and the hole transport layer, and the hole injection layer is located between the anode and the hole transport layer.

[0198] Preferably, the organic electroluminescent device further includes a capping layer, which is located on the side of the cathode away from the anode or on the side of the anode away from the cathode. When the organic electroluminescent device is a top-emitting device (emitting light from the cathode side), the capping layer is located on the side of the cathode away from the anode; when the organic electroluminescent device is a bottom-emitting device (emitting light from the anode side), the capping layer is located on the side of the anode away from the cathode.

[0199] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used. Examples include 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), the first compound shown in formula (I) of this invention, and other materials. The second compound, compound p-1, compound p-2, and compound p-3 shown in formula (II) are used, but are not limited thereto. Preferably, the hole injection layer is a monolayer structure composed of a matrix material and a dopant material. The matrix material can be a triarylamine compound, such as the first compound shown in formula (I) and the second compound shown in formula (II). The dopant material can be an axialene compound, such as compound p-1, compound p-2, and compound p-3. More preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:50. Even more preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:10.

[0200]

[0201] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Examples of substances with a density of / Vs or higher include N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), the first compound shown in formula (I) of the present invention, and the second compound shown in formula (II) of the present invention, but are not limited thereto. Preferably, the hole transport layer uses the first compound shown in formula (I) of the present invention and the second compound shown in formula (II) of the present invention. More preferably, the hole transport layer uses the first compound shown in formula (I) of the present invention.

[0202] The luminescent auxiliary layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'- Spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, the first compound shown in formula (I) of the present invention, and the second compound shown in formula (II) of the present invention, but not limited thereto. Preferably, the light-emitting auxiliary layer uses the first compound shown in formula (I) of the present invention and the second compound shown in formula (II) of the present invention. More preferably, the light-emitting auxiliary layer uses the second compound shown in formula (II) of the present invention.

[0203] The luminescent layer of the present invention may contain only a guest material, or the guest material may be dispersed in a host material, and two host materials may be used to form a dual host material. The guest material may be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material. Examples include metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, and aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(1-phenyl-1H-benzimidazole-2-yl)benzene (TPBI), TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), and 9,10-bis(2-naphthyl)anthracene (ADN), but not limited to these.

[0204] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0205] Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron transport layer is located between the light-emitting layer and the cathode, and the electron injection layer is located between the electron transport layer and the cathode.

[0206] Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron transport layer is located between the light-emitting layer and the cathode, the electron injection layer is located between the electron transport layer and the cathode, and the hole blocking layer is located between the light-emitting layer and the electron transport layer.

[0207] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0208] The electron transport layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can use aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, triazine derivatives, phenanthroline derivatives, polymers, etc. with high electron transport properties. Examples include Alq3, bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, 2-(4-biphenyl)-5-phenyloxadiazole (PBD), etc., but are not limited to these.

[0209] The hole-blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The selected material must have a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10. -6 cm 2 A concentration of / Vs or higher facilitates electron transport. Triazine derivatives and azirene derivatives are preferred.

[0210] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer;

[0211] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer;

[0212] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer;

[0213] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0214] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0215] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0216] The capping layer of this invention includes a first capping layer and / or a second capping layer. When the first or second capping layer is included, it can be a single-layer structure composed of a single substance or a single-layer structure composed of different substances. When the first and second capping layers are included, it is a multi-layer structure composed of a single substance or different substances. The capping layer material can be organic or inorganic, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, and CP-4, but are not limited thereto.

[0217]

[0218] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0219] The thickness of each of the aforementioned organic layers and capping layers is typically between 5 nm and 100 μm, preferably between 10 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0220] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0221] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0222] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments Ltd., UK, with chloroform as the solvent.

[0223] 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.

[0224] Synthesis Example 1: Synthesis of Compound I-28

[0225]

[0226] Under nitrogen protection, aa-28 (7.08 g, 30.00 mmol), bb-28 (25.29 g, 60.00 mmol), and sodium tert-butoxide (11.53 g, 120.00 mmol) were dissolved in 300 mL of toluene. Palladium acetate (0.13 g, 0.60 mmol) and tri-tert-butylphosphine (4.80 mL of 0.50 M toluene solution, 2.40 mmol) were added with stirring, and the mixture was refluxed for 8 hours. After cooling, the mixture was filtered through a diatomaceous earth / silica gel funnel. The organic solvent was removed from the filtrate by vacuum distillation. The concentrate was recrystallized from toluene, and the result was filtered to obtain compound I-28 (18.99 g, yield 69%). HPLC analysis showed a solid purity of 99.92%. Mass spectrometry m / z: 916.3832 (theoretical value: 916.3817). Theoretical elemental content (%) C 70 H 48 N2: C, 91.67; H, 5.28; N, 3.05. Measured elemental content (%): C, 91.64; H, 5.24; N, 3.08.

[0227] Synthesis Example 2: Synthesis of Compound I-30

[0228]

[0229] Preparation of intermediate cc-30:

[0230] Under nitrogen protection, aa-30 (14.15 g, 50.00 mmol), bb-30 (22.38 g, 50.00 mmol), and sodium tert-butoxide (9.61 g, 100.00 mmol) were dissolved in 300 mL of toluene. Pd₂(dba)₃ (0.23 g, 0.25 mmol) and tri-tert-butylphosphine (4.00 mL of 0.50 M toluene solution, 2.00 mmol) were added with stirring, and the mixture was refluxed for 7.5 h. After cooling, the mixture was filtered through a diatomaceous earth / silica gel funnel. The organic solvent was removed from the filtrate by vacuum distillation. The concentrate was recrystallized from toluene, and the result was filtered to obtain compound cc-30 (21.39 g, 71% yield). HPLC analysis showed a solid purity of 99.83%. Mass spectrometry m / z: 601.1416 (theoretical value: 601.1405).

[0231] Preparation of compound I-30:

[0232] Under nitrogen protection, cc-30 (18.08 g, 30.00 mmol), dd-30 (13.01 g, 30.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) were dissolved in 200 mL of toluene. Pd₂(dba)₃ (0.14 g, 0.15 mmol) and tri-tert-butylphosphine (2.40 mL of 0.50 M toluene solution, 1.20 mmol) were added with stirring, and the mixture was refluxed for 6 hours. After cooling, the mixture was filtered through a diatomaceous earth / silica gel funnel. The organic solvent was removed from the filtrate by vacuum distillation. The concentrate was recrystallized from toluene, and the result was filtered to obtain compound I-30 (19.20 g, yield 67%). HPLC analysis showed a solid purity of 99.95%. Mass spectrometry m / z: 954.4901 (theoretical value: 954.4913). Theoretical elemental content (%) C 72 H 62 N2: C, 90.53; H, 6.54; N, 2.93. Measured elemental content (%): C, 90.57; H, 6.51; N, 2.96.

[0233] Synthesis Example 3: Synthesis of Compound I-48

[0234]

[0235] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-48, bb-48, and dd-48, respectively, to obtain compound I-48 (17.20 g, yield 68%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 842.3645 (theoretical value: 842.3661). Theoretical elemental content (%) C 64 H 46N2: C, 91.18; H, 5.50; N, 3.32. Measured elemental content (%): C, 91.14; H, 5.53; N, 3.36.

[0236] Synthesis Example 4: Synthesis of Compound I-58

[0237]

[0238] Following the same preparation method as compound I-30 in Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, bb-58, and dd-48, respectively, to obtain compound I-58 (17.45 g, yield 69%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 842.3647 (theoretical value: 842.3661). Theoretical elemental content (%) C 64 H 46 N2: C, 91.18; H, 5.50; N, 3.32. Measured element content (%): C, 91.15; H, 5.52; N, 3.36.

[0239] Synthesis Example 5: Synthesis of Compound I-71

[0240]

[0241] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, bb-71, and dd-48, respectively, to obtain compound I-71 (17.16 g, yield 70%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 816.3514 (theoretical value: 816.3504). Theoretical elemental content (%) C 62 H 44 N2: C, 91.14; H, 5.43; N, 3.43. Measured element content (%): C, 91.16; H, 5.40; N, 3.47.

[0242] Synthesis Example 6: Synthesis of Compound I-73

[0243]

[0244] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-73 and bb-73, respectively, to obtain compound I-73 (17.95 g, yield 67%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 892.3830 (theoretical value: 892.3817). Theoretical elemental content (%) C 68 H48 N2: C, 91.45; H, 5.42; N, 3.14. Measured element content (%): C, 91.41; H, 5.46; N, 3.11.

[0245] Synthesis Example 7: Synthesis of Compound I-97

[0246]

[0247] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-97 and bb-97, respectively, to obtain compound I-97 (15.34 g, yield 69%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 740.3178 (theoretical value: 740.3191). Theoretical elemental content (%) C 56 H 40 N2: C, 90.78; H, 5.44; N, 3.78. Measured elemental content (%): C, 90.74; H, 5.41; N, 3.83.

[0248] Synthesis Example 8: Synthesis of Compound I-106

[0249]

[0250] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-106 and bb-71, respectively, to obtain compound I-106 (15.78 g, yield 71%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 740.3180 (theoretical value: 740.3191). Theoretical elemental content (%) C 56 H 40 N2: C, 90.78; H, 5.44; N, 3.78. Measured elemental content (%): C, 90.75; H, 5.40; N, 3.84.

[0251] Synthesis Example 9: Synthesis of Compound I-130

[0252]

[0253] Following the same preparation method as compound I-30 in Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, bb-130, and dd-48, respectively, to obtain compound I-130 (16.95 g, yield 67%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 842.3676 (theoretical value: 842.3661). Theoretical elemental content (%) C 64H 46 N2: C, 91.18; H, 5.50; N, 3.32. Measured element content (%): C, 91.14; H, 5.47; N, 3.36.

[0254] Synthesis Example 10: Synthesis of Compound I-139

[0255]

[0256] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-73 and bb-139, respectively, to obtain compound I-139 (16.65 g, yield 66%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 841.3513 (theoretical value: 841.3504). Theoretical elemental content (%) C 64 H 44 N2: C, 91.40; H, 5.27; N, 3.33. Measured elemental content (%): C, 91.42; H, 5.23; N, 3.30.

[0257] Synthesis Example 11: Synthesis of Compound I-145

[0258]

[0259] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-145 and bb-145, respectively, to obtain compound I-145 (16.92 g, yield 64%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 880.3806 (theoretical value: 880.3817). Theoretical elemental content (%) C 67 H 48 N2: C, 91.33; H, 5.49; N, 3.18. Measured elemental content (%): C, 91.31; H, 5.45; N, 3.13.

[0260] Synthesis Example 12: Synthesis of Compound I-150

[0261]

[0262] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-150, bb-71, and dd-150, respectively, to obtain compound I-150 (15.93 g, yield 65%). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 816.3517 (theoretical value: 816.3504). Theoretical elemental content (%) C62 H 44 N2: C, 91.14; H, 5.43; N, 3.43. Measured element content (%): C, 91.18; H, 5.46; N, 3.41.

[0263] Synthesis Example 13: Synthesis of Compound I-156

[0264]

[0265] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-156, bb-58, and bb-28, respectively, to obtain compound I-156 (17.43 g, yield 67%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 866.3650 (theoretical value: 866.3661). Theoretical elemental content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured elemental content (%): C, 91.45; H, 5.38; N, 3.21.

[0266] Synthesis Example 14: Synthesis of Compound I-174

[0267]

[0268] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-174, bb-58, and bb-71, respectively, to obtain compound I-174 (16.91 g, yield 65%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 866.3652 (theoretical value: 866.3661). Theoretical elemental content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured elemental content (%): C, 91.46; H, 5.37; N, 3.20.

[0269] Synthesis Example 15: Synthesis of Compound I-187

[0270]

[0271] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-187, dd-48, and bb-187, respectively, to obtain compound I-187 (16.39 g, yield 63%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 866.3670 (theoretical value: 866.3661). Theoretical elemental content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured elemental content (%): C, 91.40; H, 5.32; N, 3.26.

[0272] Synthesis Example 16: Synthesis of Compound I-204

[0273]

[0274] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-204 and bb-71, respectively, to obtain compound I-204 (16.56 g, yield 61%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 904.3831 (theoretical value: 904.3817). Theoretical elemental content (%) C 69 H 48 N2: C, 91.56; H, 5.35; N, 3.09. Measured elemental content (%): C, 91.53; H, 5.37; N, 3.04.

[0275] Synthesis Example 17: Synthesis of Compound I-265

[0276]

[0277] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, dd-145, and dd-265, respectively, to obtain compound I-265 (16.04 g, yield 64%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 834.4621 (theoretical value: 834.4634). Theoretical elemental content (%) C 62 H 26 D 18 N2: C, 89.17; H, 7.48; N, 3.35. Measured elemental content (%): C, 89.20; H, 7.43; N, 3.32.

[0278] Synthesis Example 18: Synthesis of Compound I-282

[0279]

[0280] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-73 and bb-282, respectively, to obtain compound I-282 (15.18 g, yield 67%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 754.4085 (theoretical value: 754.4070). Theoretical elemental content (%) C 56 H 26 D 14 N2: C, 89.08; H, 7.21; N, 3.71. Measured elemental content (%): C, 89.04; H, 7.24; N, 3.75.

[0281] Synthesis Example 19: Synthesis of Compound I-312

[0282]

[0283] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-312 and dd-48, respectively, to obtain compound I-312 (17.57 g, yield 65%). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 900.4332 (theoretical value: 900.4320). Theoretical elemental content (%) C 68 H 40 D8N2: C, 90.63; H, 6.26; N, 3.11. Measured elemental content (%): C, 90.66; H, 6.22; N, 3.13.

[0284] Synthesis Example 20: Synthesis of Compound I-416

[0285]

[0286] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-312 and bb-416, respectively, to obtain compound I-416 (17.66 g, yield 62%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 948.4302 (theoretical value: 948.4320). Theoretical elemental content (%) C 72 H 40 D8N2: C, 91.10; H, 5.95; N, 2.95. Measured elemental content (%): C, 91.12; H, 5.91; N, 2.98.

[0287] Synthesis Example 21: Synthesis of Compound I-431

[0288]

[0289] Following the same preparation method as compound I-28 in Example 1, aa-28 and bb-28 were replaced with equimolar amounts of aa-431 and bb-431, respectively, to obtain compound I-431 (15.38 g, yield 64%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 800.3960 (theoretical value: 800.3976). Theoretical elemental content (%) C 60 H 32 D 10 N2: C, 89.96; H, 6.54; N, 3.50. Measured elemental content (%): C, 89.92; H, 6.51; N, 3.52.

[0290] Synthesis Example 22: Synthesis of Compound I-449

[0291]

[0292] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-449, bb-449, and dd-449, respectively, to obtain compound I-449 (16.52 g, yield 62%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 887.4992 (theoretical value: 887.4979). Theoretical elemental content (%) C 66 H 25 D 21 N2: C, 89.25; H, 7.60; N, 3.15. Measured elemental content (%): C, 89.29; H, 7.62; N, 3.12.

[0293] Synthesis Example 23: Synthesis of Compound I-476

[0294]

[0295] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, bb-58, and dd-476, respectively, to obtain compound I-476 (17.42 g, yield 67%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 892.3826 (theoretical value: 892.3817). Theoretical elemental content (%) C 68 H 48 N2: C, 91.45; H, 5.42; N, 3.14. Measured element content (%): C, 91.49; H, 5.45; N, 3.11.

[0296] Synthesis Example 24: Synthesis of Compound I-499

[0297]

[0298] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-58, bb-58, and dd-499, respectively, to obtain compound I-499 (17.17 g, yield 66%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 866.3645 (theoretical value: 866.3661). Theoretical elemental content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured elemental content (%): C, 91.46; H, 5.37; N, 3.19.

[0299] Synthesis Example 25: Synthesis of Compound I-511

[0300]

[0301] Following the same preparation method as compound I-30 in Synthesis Example 2, aa-30, bb-30, and dd-30 were replaced with equimolar amounts of aa-156, bb-511, and dd-511, respectively, to obtain compound I-511 (15.26 g, yield 64%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 794.3586 (theoretical value: 794.3599). Theoretical elemental content (%) C 60 H 38 D4N2: C, 90.65; H, 5.83; N, 3.52. Measured elemental content (%): C, 90.69; H, 5.85; N, 3.49.

[0302] Synthesis Example 26: Synthesis of Compound II-6

[0303]

[0304] Preparation of intermediate CC-6:

[0305] Under nitrogen protection, AA-6 (22.59 g, 100.00 mmol), BB-6 (32.14 g, 100.00 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) were added to 400 mL of toluene. Pd(dppf)Cl2 (0.73 g, 1.00 mmol) was added with stirring, and the mixture was heated under reflux for 6 h. After the reaction was complete, the reaction solution was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was then carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene / methanol (11:3) to obtain intermediate CC-6 (36.38 g, 79%). HPLC analysis showed the solid purity to be ≥99.85%. Mass spectrometry m / z: 465.1040 (theoretical value: 465.1051).

[0306] Preparation of compound II-6:

[0307] Under nitrogen protection, CC-6 (13.99 g, 30.00 mmol), DD-6 (14.72 g, 60.00 mmol), and sodium tert-butoxide (10.38 g, 108.00 mmol) were added to 200 mL of toluene. Pd2(dba)3 (0.55 g, 0.60 mmol) and P(t-Bu)3 (2.40 mL of 0.5 M toluene solution, 1.20 mmol) were added with stirring. The mixture was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, extracted with dichloromethane and 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. Recrystallization from toluene yielded compound II-6 (20.42 g, 77%), with a solid purity ≥99.93% as determined by HPLC. Mass spectrometry m / z: 883.3941 (theoretical value: 883.3926). Theoretical element content (%) C 66 H 49 N3: C, 89.66; H, 5.59; N, 4.75. Measured elemental content (%): C, 89.70; H, 5.54; N, 4.78.

[0308] Synthesis Example 27: Synthesis of Compound II-21

[0309]

[0310] Following the same preparation method as compound II-6 in Synthesis Example 26, BB-6 was replaced with an equimolar amount of BB-21, and DD-6 was replaced with an equimolar amount of DD-21 to obtain compound II-21 (16.31 g, 77%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 705.3156 (theoretical value: 705.3144). Theoretical elemental content (%) C 52 H 39 N3: C, 88.48; H, 5.57; N, 5.95. Measured element content (%): C, 88.44; H, 5.62; N, 5.91.

[0311] Synthesis Example 28: Synthesis of Compound II-97

[0312]

[0313] Under nitrogen protection, AA-97 (12.59 g, 40.00 mmol), BB-97 (30.04 g, 120.00 mmol), and sodium tert-butoxide (20.76 g, 216.00 mmol) were added to 400 mL of toluene. Pd₂(dba)₃ (1.10 g, 1.20 mmol) and P(t-Bu)₃ (4.80 mL of 0.5 M toluene solution, 2.40 mmol) were added with stirring. The mixture was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, and extracted with dichloromethane and distilled water. The mixture was 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 upon cooling, filtered, and the resulting solid was recrystallized from toluene to give compound II-97 (24.69 g, 75%). HPLC analysis showed the solid purity to be ≥99.95%. Mass spectrometry m / z: 822.4569 (theoretical value: 822.4555). Theoretical elemental content (%) C 60 H 30 D 15 N3: C, 87.55; H, 7.34; N, 5.11. Measured element content (%): C, 87.60; H, 7.37; N, 5.15.

[0314] Synthesis Example 29: Synthesis of Compound II-132

[0315]

[0316] Following the same preparation method as compound II-97 in Synthesis Example 28, AA-97 was replaced with an equimolar amount of AA-132, and BB-97 was replaced with an equimolar amount of DD-6 to obtain compound II-132 (22.71 g, 70%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 810.3815 (theoretical value: 810.3802). Theoretical elemental content (%) C 60 H 42 D3N3: C, 88.85; H, 5.96; N, 5.18. Measured elemental content (%): C, 88.89; H, 5.94; N, 5.21.

[0317] Synthesis Example 30: Synthesis of Compound II-170

[0318]

[0319] Preparation of intermediate FF-170:

[0320] Following the same preparation method as intermediate CC-6 in Synthesis Example 26, AA-6 was replaced with an equimolar amount of EE-170, and BB-6 was replaced with an equimolar amount of BB-170 to obtain intermediate FF-170 (38.92 g, yield 78%). The solid purity was ≥99.82% as determined by HPLC. Mass spectrometry m / z: 339.1443 (theoretical value: 339.1431).

[0321] Preparation of intermediate CC-170:

[0322] Under nitrogen protection, FF-170 (34.93 g, 70.00 mmol), AA-6 (17.78 g, 70.00 mmol), K2CO3 (17.41 g, 126.00 mmol), Pd(PPh3)4 (0.81 g, 0.70 mmol), 140 mL of ethanol, and 140 mL of water were added to 420 mL of toluene. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene / methanol (9:1 v / v) to give intermediate CC-170 (21.58 g, 70% yield). The purity of the solid was ≥99.89% as determined by HPLC. Mass spectrometry m / z: 439.0884 (theoretical value: 439.0895).

[0323] Preparation of compound II-170:

[0324] Following the same preparation method as compound II-6 in Synthesis Example 26, CC-6 was replaced with an equimolar amount of CC-170, and DD-6 was replaced with an equimolar amount of BB-170, yielding compound II-170 (17.65 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 805.3470 (theoretical value: 805.3457). Theoretical elemental content (%) C 60 H 43 N3: C, 89.41; H, 5.38; N, 5.21. Measured elemental content (%): C, 89.46; H, 5.34; N, 5.24.

[0325] Synthesis Example 31: Synthesis of Compound II-184

[0326]

[0327] Following the same preparation method as compound II-170 in Synthesis Example 30, BB-170 was replaced with an equimolar amount of BB-184 to obtain compound II-184 (17.06 g, yield 69%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 823.4881 (theoretical value: 823.4865). Theoretical elemental content (%) C 60 H 61 N3: C, 87.44; H, 7.46; N, 5.10. Measured elemental content (%): C, 87.48; H, 7.41; N, 5.13.

[0328] Synthesis Example 32: Synthesis of Compound II-242

[0329]

[0330] Following the same preparation method as compound II-170 in Synthesis Example 30, BB-170 in the preparation of intermediate FF-170 was replaced with an equimolar amount of BB-242, EE-170 was replaced with an equimolar amount of EE-242, and BB-170 in compound II-170 was replaced with an equimolar amount of DD-242, yielding compound II-242 (16.87 g, yield 71%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 791.4072 (theoretical value: 791.4085). Theoretical elemental content (%) C 58 H 33 D 10 N3: C, 87.95; H, 6.74; N, 5.31. Measured elemental content (%): C, 87.91; H, 6.79; N, 5.34.

[0331] Synthesis Example 33: Synthesis of Compound II-266

[0332]

[0333] Following the same preparation method as compound II-170 in Synthesis Example 30, BB-170 in the preparation of intermediate FF-170 was replaced with an equimolar amount of BB-266, EE-170 was replaced with an equimolar amount of EE-266, and BB-170 in compound II-170 was replaced with an equimolar amount of DD-21, yielding compound II-266 (17.51 ​​g, yield 68%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 857.3783 (theoretical value: 857.3770). Theoretical elemental content (%) C 64 H 47 N3: C, 89.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 89.63; H, 5.49; N, 4.94.

[0334] Synthesis Example 34: Synthesis of Compound II-280

[0335]

[0336] Following the same preparation method as compound II-170 in Synthesis Example 30, BB-170 in the preparation of intermediate FF-170 was replaced with an equimolar amount of DD-21, and EE-170 was replaced with an equimolar amount of EE-280. Similarly, BB-170 in compound II-170 was replaced with an equimolar amount of DD-21, yielding compound II-280 (17.74 g, yield 66%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 895.3940 (theoretical value: 895.3926). Theoretical elemental content (%) C 67 H 49 N3: C, 89.80; H, 5.51; N, 4.69. Measured elemental content (%): C, 89.85; H, 5.47; N, 4.72.

[0337] Synthesis Example 35: Synthesis of Compound II-282

[0338]

[0339] Following the same preparation method as compound II-170 in Synthesis Example 30, BB-170 in the preparation of intermediate FF-170 was replaced with an equimolar amount of DD-21, EE-170 was replaced with an equimolar amount of EE-282, and BB-170 in compound II-170 was replaced with an equimolar amount of DD-6, yielding compound II-282 (18.86 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 897.3731 (theoretical value: 897.3719). Theoretical elemental content (%) C 66 H 47 N3O: C, 88.26; H, 5.28; N, 4.68. Measured elemental content (%): C, 88.30; H, 5.33; N, 4.64.

[0340] Synthesis Example 36: Synthesis of Compound II-295

[0341]

[0342] Preparation of intermediate FF-295:

[0343] Following the same preparation method as intermediate CC-6 in Synthesis Example 26, AA-6 was replaced with an equimolar amount of EE-170, and BB-6 was replaced with an equimolar amount of BB-295 to obtain intermediate FF-295 (26.34 g, yield 80%). The solid purity was ≥99.79% as determined by HPLC. Mass spectrometry m / z: 329.1575 (theoretical value: 329.1587).

[0344] Preparation of intermediate CC-295:

[0345] Under nitrogen protection, FF-295 (23.04 g, 70.00 mmol), AA-295 (9.46 g, 35.00 mmol), K2CO3 (17.41 g, 126.00 mmol), Pd(PPh3)4 (0.81 g, 0.70 mmol), 140 mL of ethanol, and 140 mL of water were added to 420 mL of toluene. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The mixture was cooled to allow crystals to form, filtered, and the resulting solid was recrystallized from toluene / methanol (9:1 v / v) to give intermediate CC-295 (18.55 g, 78% yield). The purity of the solid was determined by HPLC to be ≥99.88%. Mass spectrometry m / z: 678.2816 (theoretical value: 678.2802).

[0346] Preparation of compound II-295:

[0347] Under nitrogen protection, CC-295 (16.98 g, 25.00 mmol), DD-295 (6.13 g, 25.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) were added to 200 mL of toluene. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and P(t-Bu)₃ (1.20 mL of 0.5 M toluene solution, 0.60 mmol) were added with stirring. The mixture was heated under reflux for 4 h. After the reaction was complete, the mixture was cooled to room temperature, and extracted with dichloromethane and distilled water. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Recrystallization from toluene yielded compound II-295 (16.21 g, 73%), with a solid purity ≥ 99.94% as determined by HPLC. Mass spectrometry m / z: 887.4252 (theoretical value: 887.4239). Theoretical elemental content (%) C 66 H 53 N3: C, 89.25; H, 6.02; N, 4.73. Measured elemental content (%): C, 89.29; H, 5.99; N, 4.77.

[0348] Synthesis Example 37: Synthesis of Compound II-301

[0349]

[0350] Following the same preparation method as compound II-295 in Synthesis Example 36, BB-295 was replaced with an equimolar amount of DD-21, EE-170 with an equimolar amount of EE-242, and DD-295 with an equimolar amount of DD-301, yielding compound II-301 (16.21 g, yield 77%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 841.4253 (theoretical value: 841.4241). Theoretical elemental content (%) C 62 H 35 D 10 N3: C, 88.43; H, 6.58; N, 4.99. Measured elemental content (%): C, 88.47; H, 6.53; N, 5.02.

[0351] Synthesis Example 38: Synthesis of Compound II-305

[0352]

[0353] Preparation of intermediate CC-305:

[0354] Following the same preparation method as intermediate CC-6 in Synthesis Example 26, AA-6 was replaced with an equimolar amount of EE-170, and BB-6 was replaced with an equimolar amount of DD-21 to obtain intermediate CC-305 (23.42 g, yield 81%). The solid purity was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 289.1290 (theoretical value: 289.1274).

[0355] Preparation of compound II-305:

[0356] Under nitrogen protection, CC-305 (21.69 g, 75.00 mmol), AA-97 (7.87 g, 25.00 mmol), K2CO3 (18.66 g, 135.00 mmol), Pd(PPh3)4 (0.87 g, 0.75 mmol), 150 mL of ethanol, and 150 mL of water were added to 450 mL of toluene. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene / methanol (9:1 v / v) to give compound II-305 (14.95 g, 74% yield). The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrometry m / z: 807.3631 (theoretical value: 807.3613). Theoretical elemental content (%) C 60 H 45 N3: C, 89.19; H, 5.61; N, 5.20. Measured element content (%): C, 89.23; H, 5.57; N, 5.25.

[0357] Synthesis Example 39: Synthesis of Compound II-314

[0358]

[0359] Following the same preparation method as compound II-97 in Synthesis Example 28, AA-97 was replaced with an equimolar amount of AA-314, and BB-97 was replaced with an equimolar amount of BB-314 to obtain compound II-314 (21.62 g, 70%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 771.3626 (theoretical value: 771.3613). Theoretical elemental content (%) C 57 H 45 N3: C, 88.68; H, 5.88; N, 5.44. Measured element content (%): C, 88.73; H, 5.84; N, 5.47.

[0360] Synthesis Example 40: Synthesis of Compound II-329

[0361]

[0362] Following the same preparation method as compound II-6 in Synthesis Example 26, AA-6 was replaced with an equimolar amount of AA-329, BB-6 with an equimolar amount of BB-242, and DD-6 with an equimolar amount of DD-21 to obtain compound II-329 (15.54 g, 79%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 655.2972 (theoretical value: 655.2987). Theoretical elemental content (%) C 48 H 37 N3: C, 87.91; H, 5.69; N, 6.41. Measured elemental content (%): C, 87.96; H, 5.65; N, 6.44.

[0363] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0364] The following are compounds other than the first compound shown in formula (I) and the second compound shown in formula (II) used in the device fabrication examples:

[0365]

[0366] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were measured. The lifetime of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature (brightness decay to 95% of initial brightness). The test results are shown in Table 1.

[0367] Comparative device fabrication example 1: Comparative device 1

[0368] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0369] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 60 nm; b) I-28 as a hole transport layer with a thickness of 75 nm; c) RH-1, RH-2, and Ir(dpm)(piq)2 (mass ratio of 64:32:4) as a light-emitting layer with a thickness of 30 nm; d) BAlq as a hole blocking layer with a thickness of 20 nm; e) NBphen and Liq (mass ratio of 7:3) as an electron transport layer with a thickness of 20 nm; f) LiF as an electron injection layer with a thickness of 0.1 nm; g) Mg and Ag (mass ratio of 1:9) as a cathode with a thickness of 15 nm; h) CP-4 as a capping layer with a thickness of 100 nm.

[0370] Comparative device fabrication examples 2-9: Comparative devices 2-9

[0371] By replacing I-28 in the hole transport layer with I-30, I-73, I-145, I-312, II-6, II-97, II-170, and II-305 respectively, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 9 can be obtained.

[0372] Device fabrication example 1: Light-emitting device 1

[0373] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0374] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 60 nm; b) I-28 as a hole transport layer with a thickness of 35 nm; c) II-6 as a light-emitting auxiliary layer with a thickness of 40 nm; d) RH-1, RH-2 and Ir(dpm)(piq)2 (mass ratio of 64:32:4) as a light-emitting layer with a thickness of 30 nm; e) BAlq as a hole blocking layer with a thickness of 20 nm; f) NBphen and Liq (mass ratio of 7:3) as an electron transport layer with a thickness of 20 nm; g) LiF as an electron injection layer with a thickness of 0.1 nm; h) Mg and Ag (mass ratio of 1:9) as a cathode with a thickness of 15 nm; i) CP-4 as a capping layer with a thickness of 100 nm.

[0375] Device fabrication example 2: Light-emitting device 2

[0376] By replacing II-6 in the light-emitting auxiliary layer with II-282, and following the same steps as in device fabrication example 1, light-emitting device 2 can be obtained.

[0377] Device fabrication example 3: Light-emitting device 3

[0378] By replacing I-28 in the hole transport layer with I-30 and II-6 in the light-emitting auxiliary layer with II-305, and following the same steps as in device fabrication example 1, light-emitting device 3 can be obtained.

[0379] Device fabrication example 4: Light-emitting device 4

[0380] By replacing I-28 in the hole transport layer with I-48 and II-6 in the light-emitting auxiliary layer with II-184, and following the same steps as in device fabrication example 1, the light-emitting device 4 can be obtained.

[0381] Device fabrication example 5: Light-emitting device 5

[0382] By replacing I-28 in the hole transport layer with I-58 and II-6 in the light-emitting auxiliary layer with II-21, and following the same steps as in device fabrication example 1, the light-emitting device 5 can be obtained.

[0383] Device fabrication example 6: Light-emitting device 6

[0384] By replacing I-28 in the hole transport layer with I-58 and II-6 in the light-emitting auxiliary layer with II-266, and following the same steps as in device fabrication example 1, the light-emitting device 6 can be obtained.

[0385] Device fabrication example 7: Light-emitting device 7

[0386] By replacing I-28 in the hole transport layer with I-71 and II-6 in the light-emitting auxiliary layer with II-97, and following the same steps as in device fabrication example 1, the light-emitting device 7 can be obtained.

[0387] Device fabrication example 8: Light-emitting device 8

[0388] By replacing I-28 in the hole transport layer with I-71 and II-6 in the light-emitting auxiliary layer with II-314, and following the same steps as in device fabrication example 1, the light-emitting device 8 can be obtained.

[0389] Device fabrication example 9: Light-emitting device 9

[0390] By replacing I-28 in the hole transport layer with I-73 and II-6 in the light-emitting auxiliary layer with II-97, and following the same steps as in device fabrication example 1, the light-emitting device 9 can be obtained.

[0391] Device fabrication example 10: Light-emitting device 10

[0392] By replacing I-28 in the hole transport layer with I-73 and II-6 in the light-emitting auxiliary layer with II-242, and following the same steps as in Device Fabrication Example 1, the light-emitting device 10 can be obtained.

[0393] Device fabrication example 11: Light-emitting device 11

[0394] By replacing I-28 in the hole transport layer with I-73 and II-6 in the light-emitting auxiliary layer with II-329, and following the same steps as in Device Fabrication Example 1, the light-emitting device 11 can be obtained.

[0395] Device fabrication example 12: Light-emitting device 12

[0396] By replacing I-28 in the hole transport layer with I-97 and II-6 in the light-emitting auxiliary layer with II-280, and following the same steps as in Device Fabrication Example 1, the light-emitting device 12 can be obtained.

[0397] Device fabrication example 13: Light-emitting device 13

[0398] By replacing I-28 in the hole transport layer with I-106 and II-6 in the light-emitting auxiliary layer with II-170, and following the same steps as in device fabrication example 1, the light-emitting device 13 can be obtained.

[0399] Device fabrication example 14: Light-emitting device 14

[0400] By replacing I-28 in the hole transport layer with I-130 and II-6 in the light-emitting auxiliary layer with II-295, and following the same steps as in Device Fabrication Example 1, the light-emitting device 14 can be obtained.

[0401] Device fabrication example 15: Light-emitting device 15

[0402] By replacing I-28 in the hole transport layer with I-139 and II-6 in the light-emitting auxiliary layer with II-266, and following the same steps as in device fabrication example 1, the light-emitting device 15 can be obtained.

[0403] Device Fabrication Example 16: Light Emitting Device 16

[0404] By replacing I-28 in the hole transport layer with I-145 and II-6 in the light-emitting auxiliary layer with II-132, and following the same steps as in Device Fabrication Example 1, the light-emitting device 16 can be obtained.

[0405] Device Fabrication Example 17: Light Emitting Device 17

[0406] By replacing I-28 in the hole transport layer with I-145 and II-6 in the light-emitting auxiliary layer with II-242, and following the same steps as in Device Fabrication Example 1, the light-emitting device 17 can be obtained.

[0407] Device fabrication example 18: Light-emitting device 18

[0408] By replacing I-28 in the hole transport layer with I-150 and II-6 in the light-emitting auxiliary layer with II-301, and following the same steps as in device fabrication example 1, the light-emitting device 18 can be obtained.

[0409] Device fabrication example 19: Light-emitting device 19

[0410] By replacing I-28 in the hole transport layer with I-156 and II-6 in the light-emitting auxiliary layer with II-184, and following the same steps as in device fabrication example 1, the light-emitting device 19 can be obtained.

[0411] Device fabrication example 20: Light-emitting device 20

[0412] By replacing I-28 in the hole transport layer with I-174 and II-6 in the light-emitting auxiliary layer with II-132, and following the same steps as in device fabrication example 1, the light-emitting device 20 can be obtained.

[0413] Device fabrication example 21: Light-emitting device 21

[0414] By replacing I-28 in the hole transport layer with I-187, and following the same steps as in Device Fabrication Example 1, the light-emitting device 21 can be obtained.

[0415] Device fabrication example 22: Light-emitting device 22

[0416] By replacing I-28 in the hole transport layer with I-204 and II-6 in the light-emitting auxiliary layer with II-21, and following the same steps as in device fabrication example 1, light-emitting device 22 can be obtained.

[0417] Device fabrication example 23: Light-emitting device 23

[0418] By replacing I-28 in the hole transport layer with I-204 and II-6 in the light-emitting auxiliary layer with II-266, and following the same steps as in device fabrication example 1, light-emitting device 23 can be obtained.

[0419] Device fabrication example 24: Light-emitting device 24

[0420] By replacing I-28 in the hole transport layer with I-265 and II-6 in the light-emitting auxiliary layer with II-282, and following the same steps as in Device Fabrication Example 1, the light-emitting device 24 can be obtained.

[0421] Device fabrication example 25: Light-emitting device 25

[0422] By replacing I-28 in the hole transport layer with I-282 and II-6 in the light-emitting auxiliary layer with II-170, and following the same steps as in device fabrication example 1, the light-emitting device 25 can be obtained.

[0423] Device Fabrication Example 26: Light Emitting Device 26

[0424] By replacing I-28 in the hole transport layer with I-282 and II-6 in the light-emitting auxiliary layer with II-280, and following the same steps as in Device Fabrication Example 1, the light-emitting device 26 can be obtained.

[0425] Device fabrication example 27: Light-emitting device 27

[0426] By replacing I-28 in the hole transport layer with I-312, and following the same steps as in Device Fabrication Example 1, the light-emitting device 27 can be obtained.

[0427] Device fabrication example 28: Light-emitting device 28

[0428] By replacing I-28 in the hole transport layer with I-312 and II-6 in the light-emitting auxiliary layer with II-170, and following the same steps as in Device Fabrication Example 1, the light-emitting device 28 can be obtained.

[0429] Device fabrication example 29: Light-emitting device 29

[0430] By replacing I-28 in the hole transport layer with I-312 and II-6 in the light-emitting auxiliary layer with II-314, and following the same steps as in device fabrication example 1, light-emitting device 29 can be obtained.

[0431] Device fabrication example 30: Light-emitting device 30

[0432] By replacing I-28 in the hole transport layer with I-416 and II-6 in the light-emitting auxiliary layer with II-184, and following the same steps as in Device Fabrication Example 1, the light-emitting device 30 can be obtained.

[0433] Device fabrication example 31: Light-emitting device 31

[0434] By replacing I-28 in the hole transport layer with I-431 and II-6 in the light-emitting auxiliary layer with II-301, and following the same steps as in device fabrication example 1, the light-emitting device 31 can be obtained.

[0435] Device fabrication example 32: Light-emitting device 32

[0436] By replacing I-28 in the hole transport layer with I-449 and II-6 in the light-emitting auxiliary layer with II-170, and following the same steps as in Device Fabrication Example 1, the light-emitting device 32 can be obtained.

[0437] Device fabrication example 33: Light-emitting device 33

[0438] By replacing I-28 in the hole transport layer with I-476, and following the same steps as in Device Fabrication Example 1, the light-emitting device 33 can be obtained.

[0439] Device fabrication example 34: Light-emitting device 34

[0440] By replacing I-28 in the hole transport layer with I-499 and II-6 in the light-emitting auxiliary layer with II-97, and following the same steps as in device fabrication example 1, the light-emitting device 34 can be obtained.

[0441] Device fabrication example 35: Light-emitting device 35

[0442] By replacing I-28 in the hole transport layer with I-511 and II-6 in the light-emitting auxiliary layer with II-305, and following the same steps as in Device Fabrication Example 1, the light-emitting device 35 can be obtained.

[0443] Table 1

[0444]

[0445]

[0446]

[0447] Based on the device data in Table 1, it can be concluded that using the first compound as the hole transport layer and the second compound as the light-emitting auxiliary layer can effectively reduce the driving voltage of the device, improve the luminous efficiency of the device, and extend the lifespan of the device.

[0448] 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 cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region including a hole transport layer and a light-emitting auxiliary layer, the hole transport layer being located between the anode and the light-emitting layer, and the light-emitting auxiliary layer being located between the light-emitting layer and the hole transport layer, characterized in that, The hole transport layer contains a first compound represented by formula (I), and the light-emitting auxiliary layer contains a second compound represented by formula (II): Wherein, L is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring fused with a C3-C6 aliphatic ring; The L1 to L4 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a C3 to C6 aliphatic ring; Ar1~Ar4, Ar 101 ~Ar 106 are independently selected from one of the following structures, Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different. The R mentioned 21 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by the fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or two adjacent R groups. 21 They connect to form substituted or unsubstituted saturated or unsaturated C3~C6 carbon rings; Furthermore, at least one of Ar1 to Ar4 is selected from the group consisting of a C6-C30 aryl group or a C6-C30 aromatic ring fused with a C3-C6 aliphatic ring, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene. The L mentioned 101 ~L 109 It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C6 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene. The a mentioned 101 Choose from 0, 1, 2, or 3; The R mentioned 101 Each time it appears, it is selected from the same or different groups selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C30 aryl group, and a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C6 aliphatic ring.

2. The organic electroluminescent device according to claim 1, characterized in that, The L is selected from one of the following structures: Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different. The R mentioned 11 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C6 aliphatic ring; The R mentioned 12 R 13 Independently selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or the aforementioned R. 12 With R 13 They connect to form substituted or unsubstituted saturated or unsaturated C3~C10 carbon rings.

3. The organic electroluminescent device according to claim 1, characterized in that, The L1 to L4 are independently selected from a single bond or one of the following structures: Wherein, the a 11 b 11 c 11 d 11 e 11 R 11 R 12 R 13 All are as described in claim 2.

4. The organic electroluminescent device according to claim 1, characterized in that, At least one of Ar1 to Ar4 is selected from one of the following structures: Wherein, the a 24 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 24 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the e 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the g mentioned 24 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, either the same or different. The R mentioned 24 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group.

5. The organic electroluminescent device according to claim 1, characterized in that, The L mentioned 101 ~L 109 Independently selected from a single bond or one of the following structures: Wherein, the a 11 b 11 c 11 d 11 e 11 R 11 R 12 R 13 All as described in claim 2; The R mentioned 14 It is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, and substituted or unsubstituted phenanthryl.

6. The organic electroluminescent device according to claim 1, characterized in that, The first compound is selected from one of the structures shown in formula (IA) to (IH): Wherein, L, L2~L4 are all as described in claim 1; The a mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 31 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 31 Each time it appears, it is selected from 0, 1, or 2, either the same or different. The R mentioned 31 Each time it appears, it is selected from one of the following, either identically or differently: hydrogen atom, deuterium atom, methyl, isopropyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, methyl-substituted norbornyl, ethyl-substituted adamantyl, ethyl-substituted norbornyl, isopropyl-substituted adamantyl, isopropyl-substituted norbornyl, tert-butyl-substituted adamantyl, and tert-butyl-substituted norbornyl. The Ar2 to Ar4 are independently selected from one of the following structures: The a mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 41 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the d mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the e mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3 or 4, either the same or different. The R mentioned 41 Each time it appears, it is selected from one of the following, either identically or differently: hydrogen atom, deuterium atom, methyl, isopropyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, methyl-substituted norbornyl, ethyl-substituted adamantyl, ethyl-substituted norbornyl, isopropyl-substituted adamantyl, isopropyl-substituted norbornyl, tert-butyl-substituted adamantyl, and tert-butyl-substituted norbornyl. The L1' to L4' are independently selected from one of the following: a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a C3 to C6 aliphatic ring, or a divalent group.

7. The organic electroluminescent device according to claim 1, characterized in that, The first compound is selected from one of the following structures: 。 8. The organic electroluminescent device according to claim 1, characterized in that, The second compound is selected from one of the following structures: 。 9. The organic electroluminescent device according to claim 1, characterized in that, The organic electroluminescent device also includes a capping layer.

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