A triarylamine derivative based on fluorenyl heterocycle and its organic electroluminescent device

Abstract

The present invention provides a triarylamine derivative based on a fluorenyl heterocycle and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The novel organic compound of the present invention has an appropriate HOMO energy level and T1 value, which is conducive to the injection and transmission of electrons; in addition, the compound has a high glass transition temperature (Tg), and has good film-forming properties and thermal stability. When used as a hole transport layer / hole transport auxiliary layer material in an OLED device, under the action of an external electric field, the film-forming stability is good, and the hole injection and transmission balance inside the device can be effectively improved, the luminous efficiency of the device is improved, the driving voltage of the device is reduced, and the service life of the device is extended. The preparation method of the triarylamine derivative based on a fluorenyl heterocycle described in the present invention is simple and low-cost, and has good application effects and industrialization prospects when applied to organic electroluminescent devices.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent materials, and in particular to a triarylamine derivative based on a fluorenyl heterocycle and an organic electroluminescent device thereof. Background Art

[0002] Organic electroluminescent display technology is a third-generation display technology currently believed to replace some LCD products within the next 20 years. OLEDs (Organic Light Emitting Diodes), a rising star in display devices, are being hailed as "dream displays."

[0003] Compared with traditional display devices, OLEDs have the characteristics of simple structure, fast response speed, diverse luminous colors, low power consumption and wide viewing angle. In practical applications, they have the advantages of good flexibility and suitability for the production of large-area display devices. They are generally considered by industry insiders to be the most promising display technology.

[0004] Currently, the vast majority of OLEDs are multilayer sandwich-type, dual-carrier DC injection devices. Their efficiency and lifetime are closely related to the device structure. OLEDs typically consist of a transparent, high-work-function conductive anode (ITO), a low-work-function metal cathode (such as a Mg:Ag alloy), and an organic functional layer. Between the cathode and anode lies a single or multiple organic functional layer. In practical devices, to improve device luminescence performance, the organic functional layer typically adopts a multilayer structure, primarily comprising a hole transport layer (HTL), an emitting layer (EML), and an electron transport layer (ETL). Under the influence of an applied electric field, electrons and holes generated at the cathode and anode are injected into the organic functional layer between the two stages. These injected electrons and holes migrate through the electron transport layer and hole transport layer toward the emitting layer, where they recombine to form excitons. When the excitons transition back to their ground state, luminescence occurs, a phenomenon known as electroluminescence.

[0005] As a new solid-state lighting method, OLEDs still face many challenges in terms of luminescence performance and manufacturing technology. Current hole transport materials generally suffer from poor thermal stability, low HOMO values, and low triplet energy levels, all of which affect device performance and lifetime. Therefore, it is crucial to develop hole transport materials with good film-forming properties and thermal stability, high hole mobility, and an appropriate HOMO energy level, while also matching the work function of ITO. Summary of the Invention

[0006] In response to the problems existing in the prior art, the present invention provides a triarylamine derivative based on a fluorenyl heterocycle and an organic electroluminescent device thereof. The triarylamine derivative based on a fluorenyl heterocycle provided by the present invention is applied to the hole transport layer of the device, which can effectively improve the luminous efficiency and service life of OLEDs.

[0007] Specifically, the present invention provides a triarylamine derivative based on a fluorenyl heterocycle, wherein the triarylamine derivative based on a fluorenyl heterocycle is represented by the following formula I:

[0008]

[0009] Wherein, the W is selected from O, S or N(R2);

[0010] R1 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0011] R2 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0012] The k1 is selected from 0, 1, 2, 3 or 4; when k1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to form a substituted or unsubstituted ring;

[0013] The Ar1 is selected from the group shown in Formula 1-a or Formula 1-b, and the * represents a connection site;

[0014]

[0015] The R a 、R b Same or different from each other, R a and R bAt least one of them is selected from the group shown in 1-c, and the rest are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring;

[0016] The R3 groups are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0017] The X is selected from O, S or N (R c );

[0018] Said Y is selected from CH or N; and X and Y cannot be selected from N at the same time;

[0019] Said T is selected from CH or N;

[0020] The R c Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0021] R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0022] The n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;

[0023] The n3 is selected from 0, 1, 2, 3, 4 or 5; when n3 is greater than 1, two or more R5 are the same or different from each other, or two adjacent R5 are connected to each other to form a substituted or unsubstituted ring;

[0024] The L3 is selected from one of a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof;

[0025] The Ar2 is selected from one or a combination of the following groups:

[0026]

[0027] wherein said z are the same or different and are selected from CH or N;

[0028] Said p is selected from O, S or N (R d );

[0029] Said q is selected from CH or N;

[0030] The M1 is selected from O, S, N (R e )、Si(R f ) Any one of 2;

[0031] The M2 and M3 are the same or different and are selected from single bond, O, S, C (R g R h )、N(R e )、Si(R f ) Any one of 2;

[0032] The R d Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0033] The R eOne selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0034] The R f One selected from the group consisting of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0035] The R g 、R h the same or different selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or R g 、R h are connected to form a substituted or unsubstituted ring;

[0036] R6 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0037] The p1 is selected from 0, 1, 2, 3, 4 or 5; the p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the p3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the p4 is selected from 0, 1, 2, 3 or 4; when two or more R6 are present, the two or more R6 are the same or different, or two adjacent R6 are connected to form a substituted or unsubstituted ring;

[0038] The L0, L1 and L2 are the same or different and are selected from one of the following groups: a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof.

[0039] Beneficial effects

[0040] The fluorenol heterocycle-based triarylamine derivatives of Formula I provided by the present invention have appropriate HOMO energy levels, excellent heat resistance, and stability, effectively reducing the driving voltage to ensure efficient hole injection; and have high mobility, effectively improving hole transport performance. In summary, the fluorenol heterocycle-based triarylamine derivatives provided by the present invention, when used as hole transport layers in OLED devices, can effectively improve the device's luminous efficiency, driving voltage, and service life, and have good application prospects. DETAILED DESCRIPTION

[0041] The following will be combined with the technical solutions of the embodiments of the present invention to further clarify and fully illustrate. Obviously, the embodiments described are only part of the embodiments of the present invention, rather than all the embodiments. After reading this invention, those skilled in the art will be able to modify the various equivalent forms of the present invention within the scope of the present invention.

[0042] In this manual, It means the portion to which another substituent is attached. Can be attached at any optional position of the attached group / fragment.

[0043] In this specification, when the position of a substituent or a connection site on a ring is not fixed, it means that it can be connected to any of the optional sites of the ring. For example, Can represent Can represent Can represent And so on.

[0044] Examples of the halogen according to the present invention may include fluorine, chlorine, bromine and iodine.

[0045] The alkyl group described in the present invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 20 carbon atoms, more preferably 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, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but is not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.

[0046] The heterocycloalkyl group of the present invention is a general term for a group in which one or more carbon atoms in a cycloalkyl group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. The heterocycloalkyl group may include, but is not limited to, tetrahydropyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothienyl, etc.

[0047] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R n )3 groups, wherein each R n The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each R n The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 8 carbon atoms. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 7 carbon atoms. Preferably, each R nThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples of the substituted or unsubstituted silyl group may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentanylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.

[0048] The cycloalkyl group of the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from a cyclic alkane molecule, which can be a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, or a bridged ring cycloalkyl group. Preferably, it has 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, fenchyl, isobornyl, etc., but is not limited thereto.

[0049] The aryl group described herein refers to a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. The aryl group may be a monocyclic aryl group, a polycyclic aryl group, or a condensed ring aryl group. The aryl group preferably has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic aromatic group refers to an aromatic group having only one aromatic ring in the molecule, for example, phenyl, etc., but not limited thereto; the polycyclic aromatic group refers to an aromatic group containing two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited thereto; the fused-ring aromatic group refers to an aromatic group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirofluorenyl, spirobifluorenyl, etc., but not limited thereto.

[0050] The heteroaryl group of the present invention is a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atoms, and preferably has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The attachment point of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzo Quinoxalinyl, o-phenanthrolinyl, naphthyridinyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthryl, spirofluorenylthioanthryl, etc., but are not limited thereto.

[0051] The arylene group described herein refers to the divalent group remaining after removing two hydrogen atoms from the aromatic carbon nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene group, a polycyclic arylene group, or a condensed-ring arylene group, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic arylene group includes, but is not limited to, phenylene groups; the polycyclic arylene group includes, but is not limited to, biphenylene groups and terphenylene groups; specific examples include, but are not limited to, naphthylene groups, anthrylene groups, phenanthrenyl groups, pyrenyl groups, triphenylene groups, and fluoranthenyl groups.

[0052] The heteroarylene group is a general term for a divalent group in which at least one carbon atom in an arylene group is replaced by a heteroatom, and the heteroatom includes but is not limited to oxygen, sulfur, nitrogen or phosphorus atoms. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The attachment site of the heteroarylene group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group or a condensed-ring heteroarylene group. Specific examples of the monocyclic and condensed-ring heteroarylene groups may include pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, dibenzocarbazolylene, etc., but are not limited thereto; specific examples of the polycyclic heteroarylene groups may include bipyridylene, bipyrimidylene, phenylpyridylene, etc., but are not limited thereto.

[0053] The alicyclic group described herein is a general term for a monovalent group obtained by removing a hydrogen atom from an alicyclic hydrocarbon molecule, and may be a cycloalkyl group, a cycloalkenyl group, or the like, preferably having 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and particularly preferably 5 to 7 carbon atoms. The alicyclic group may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl.

[0054] The fused alicyclic and aromatic ring radical of the present invention refers to a monovalent group formed by fusion of an alicyclic ring and an aromatic ring, with one hydrogen atom removed. Preferably, the fused alicyclic and aromatic ring radical has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused alicyclic and aromatic ring radical may include, but is not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, and benzocycloheptenyl.

[0055] The fused alicyclic and heteroaromatic ring radicals described herein are a general term for monovalent groups formed by fusion of an alicyclic ring and a heteroaromatic ring, with one hydrogen atom removed. Preferably, the fused alicyclic and heteroaromatic ring radicals have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and particularly preferably 5 to 12 carbon atoms. The fused ring group of the alicyclic ring and the heteroaromatic ring may include a pyridocyclopropyl group, a pyridocyclobutyl group, a pyridocyclopentyl group, a pyridocyclohexyl group, a pyridobenzocycloheptyl group, a pyrimidocyclopropyl group, a pyrimidocyclobutyl group, a pyrimidocyclopentyl group, a pyrimidocyclohexyl group, a pyrimidobenzocycloheptyl group, a dibenzofuranocyclopropyl group, a dibenzofuranocyclobutyl group, a dibenzofuranocyclopentyl group, a dibenzofuranocyclohexyl group, a dibenzofuranocycloheptyl group, a dibenzothienocyclopropyl group, a dibenzothienocyclobutyl group, a dibenzothienocyclopentyl group, a dibenzothienocyclohexyl group, a dibenzothienocycloheptyl group, a carbazocyclopropyl group, a carbazocyclobutyl group, a carbazocyclopentyl group, a carbazocyclohexyl group, a carbazocycloheptyl group, and the like, but is not limited thereto.

[0056] The fused cyclic radical of an alicyclic ring and an aromatic ring described in the present invention is a general term for a divalent group formed by condensing an alicyclic ring and an aromatic ring and removing two hydrogen atoms. Preferably, the fused cyclic radical has 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused cyclic radical of an alicyclic ring and an aromatic ring may include, but is not limited to, benzocyclopropylene, benzocyclobutylene, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentenylene, benzocyclohexenylene, benzocycloheptenylene, naphthocyclopropylene, naphthocyclobutylene, naphthocyclopentylene, naphthocyclohexylene, and the like.

[0057] The sub-condensed cyclic group of the alicyclic ring and heteroaromatic ring described in the present invention refers to a general term for a divalent group obtained by removing two hydrogen atoms after the alicyclic ring and the heteroaromatic ring are fused together. Preferably, it has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The sub-condensed cyclic group of the alicyclic ring and heteroaromatic ring may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, sub-condensed cyclic group Dibenzofuranocyclopropyl, dibenzofuranocyclobutylene, dibenzofuranocyclopentylene, dibenzofuranocyclohexylene, dibenzofuranocycloheptylene, dibenzothienocyclopropylene, dibenzothienocyclobutylene, dibenzothienocyclopentylene, dibenzothienocyclohexylene, dibenzothienocycloheptylene, carbazolylcyclopropylene, carbazolylcyclobutylene, carbazolylcyclopentylene, carbazolylcyclohexylene, carbazolylcycloheptylene, etc., but are not limited to these.

[0058] The “substituted…” mentioned in the present invention, such as “substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted silyl, substituted aryl, substituted heteroaryl, substituted fused ring of aliphatic ring and aromatic ring, substituted alkylene, substituted cycloalkylene, substituted arylene, substituted heteroarylene”, refers to independently being mono- or poly-substituted by the following groups: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, etc., but not limited thereto, or two adjacent substituents may be connected to form a ring. Preferably, the following radicals are mono- or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, perylenyl, pyrenyl, benzyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazine, carbazolyl, acridinyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, etc., but are not limited thereto.

[0059] In this specification, "connected to form a substituted or unsubstituted ring" means that adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by combining adjacent groups can be connected to another ring to form a spiro structure. The following examples are shown:

[0060]

[0061] In this specification, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but is not limited thereto.

[0062] The present invention provides a triarylamine derivative based on a fluorenyl heterocycle, wherein the triarylamine derivative based on a fluorenyl heterocycle is represented by the following formula I:

[0063]

[0064] Wherein, the W is selected from O, S or N(R2);

[0065] R1 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0066] R2 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0067] The k1 is selected from 0, 1, 2, 3 or 4; when k1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to form a substituted or unsubstituted ring;

[0068] The Ar1 is selected from the group shown in Formula 1-a or Formula 1-b, and the * represents a connection site;

[0069]

[0070] The R a 、R b Same or different from each other, R a and R b At least one of them is selected from the group shown in 1-c, and the rest are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring;

[0071] The R3 groups are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0072] The X is selected from O, S or N (R c );

[0073] Said Y is selected from CH or N; and X and Y cannot be selected from N at the same time;

[0074] Said T is selected from CH or N;

[0075] The R c Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0076] R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0077] The n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;

[0078] The n3 is selected from 0, 1, 2, 3, 4 or 5; when n3 is greater than 1, two or more R5 are the same or different from each other, or two adjacent R5 are connected to each other to form a substituted or unsubstituted ring;

[0079] The L3 is selected from one of a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof;

[0080] The Ar2 is selected from one or a combination of the following groups:

[0081]

[0082] wherein said z are the same or different and are selected from CH or N;

[0083] Said p is selected from O, S or N (R d );

[0084] Said q is selected from CH or N;

[0085] The M1 is selected from O, S, N (R e )、Si(R f ) Any one of 2;

[0086] The M2 and M3 are the same or different and are selected from single bond, O, S, C (R g R h )、N(R e )、Si(R f ) Any one of 2;

[0087] The R d Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0088] The R e One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0089] The R fOne selected from the group consisting of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0090] The R g 、R h the same or different selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or R g 、R h are connected to form a substituted or unsubstituted ring;

[0091] R6 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0092] The p1 is selected from 0, 1, 2, 3, 4 or 5; the p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the p3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the p4 is selected from 0, 1, 2, 3 or 4; when two or more R6 are present, the two or more R6 are the same or different, or two adjacent R6 are connected to form a substituted or unsubstituted ring;

[0093] The L0, L1 and L2 are the same or different and are selected from one of the following groups: a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof.

[0094] Preferably, R2 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, any one of a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropanyl group, a substituted or unsubstituted benzocyclobutanyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted dihydroindanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptanyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, and a substituted or unsubstituted quinoxalinyl group;

[0095] Preferably, the R a 、R b Not Formula 1-c hour:

[0096] selected from hydrogen, deuterium, tritium, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted any one of benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0097] Preferably, in formula 1-b, the Ra is not hour:

[0098] It is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring sub-condensed ring group, and a substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring sub-condensed ring group.

[0099] Preferably, in formula 1-b, the Ra is not hour:

[0100] Selected from single bonds, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenylene, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylenefluorenylene, pyridinylene, pyrimidinylene, triazinylene, furanylene, thienylene, bipyridinylene, bipyrimidinylene, phenylpyridine, quinolylene, isoquinolylene, indolylene, benzothienylene, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzodibenzofuranylene, dibenzothienylene, benzodibenzothienylene, carbazolylene, benzocarbazolylene, acridinylene, 9,10-dihydroacridinylene, phenoxazinylene, phenothiazinylene, phenoxathiylene.

[0101] Preferably, the triarylamine derivative based on fluorenyl heterocycle is selected from at least one of Formula I-1 to Formula I-5:

[0102]

[0103] Preferably, the 1-a is selected from one of the following groups:

[0104]

[0105] Preferably, the 1-c One selected from the following groups:

[0106]

[0107] Said T is selected from CH or N;

[0108] The R c Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0109] R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0110] The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R5, the two or more R5 are the same or different, or two adjacent R5 are connected to form a substituted or unsubstituted ring;

[0111] The L3 is selected from one of a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof;

[0112] Preferably, at most 3 of the 4 Ts in each ring are selected from N, or at most 2 are selected from N, or at most one is selected from N.

[0113] Further preferably, the 1-c One selected from the following groups:

[0114]

[0115]

[0116]

[0117] n0 is selected from 0, 1 or 2; n1 is selected from 0, 1, 2 or 3; n2 is selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4 or 5; n4 is selected from 0 or 1; n5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; n7 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0118] The R c Any one selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0119] R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C60 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0120] The L3 is selected from one of a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring sub-condensed ring group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring sub-condensed ring group, or a combination thereof;

[0121] Preferably, the R c selected from hydrogen, deuterium, tritium, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted dihydroindanyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptanyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0122] Preferably, R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof;

[0123] Preferably, L3 is selected from single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylenefluorenyl, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, bipyridylene, bipyrimidylene, phenylpyridine, quinolylene, isoquinolylene yl, indolylene, benzothiophenylene, benzofurylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofurylene, benzodibenzofurylene, dibenzothiophenylene, benzodibenzothiophenylene, carbazolylene, benzocarbazolylene, acridinylene, 9,10-dihydroacridinylene, phenoxazinylene, phenothiazinylene, phenoxathiylene;

[0124] In the present invention, when the 1-c When it is Ra of formula 1-b or the corresponding position of formula I-3, I-5, another connection site is in the ring Any one of C.

[0125] Preferably, Ar2 is selected from one or a combination of the following groups:

[0126]

[0127] The R t One selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0128] The R i 、R j the same or different ones selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0129] The R k One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0130] R6 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, or a combination thereof;

[0131] Said p1 is selected from 0, 1, 2, 3, 4, or 5; said p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said p3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said p4 is selected from 0, 1, 2, 3, or 4; said p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; said p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; said p7 is selected from 0, 1, or 2; said p8 is selected from 0, 1, 2, or 3; said p9 is selected from 0, 1, 2, 3, 4, 5, or 6; said p 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said p 11 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R6 are present, the two or more R6 are the same as or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring;

[0132] Preferably, the R t selected from hydrogen, deuterium, tritium, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted dihydroindanyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptanyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof, or two adjacent R t are connected to each other to form a substituted or unsubstituted ring;

[0133] Preferably, the R i 、R jthe same or different selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocyclopropanyl, a substituted or unsubstituted benzocyclobutanyl, a substituted or unsubstituted benzocyclobutenyl, a substituted or unsubstituted dihydroindanyl, a substituted or unsubstituted indanyl, a substituted or unsubstituted tetrahydronaphthyl, a substituted or unsubstituted dihydronaphthyl, a substituted or unsubstituted benzocycloheptanyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted quinoxalinyl, or a combination thereof;

[0134] Preferably, the R k selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof, or two adjacent R k are connected to each other to form a substituted or unsubstituted ring;

[0135] Preferably, R6 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof.

[0136] Preferably, L0, L1 and L2 are selected from a single bond or one or a combination of the following groups:

[0137]

[0138] wherein said e are the same or different and are selected from CH or N;

[0139] The M4 and M5 are the same or different and are selected from O, S, N (R o )

[0140] The R o One selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0141] The R p 、Rq the same or different ones selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0142] R7 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0143] The r1 is selected from 0, 1, 2, 3 or 4; the r2 is selected from 0, 1, 2, 3, 4, 5 or 6; the r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R7 are present, the two or more R7 are the same as or different from each other, or two adjacent R7 are connected to each other to form a substituted or unsubstituted ring.

[0144] Preferably, L0, L1 and L2 are selected from a single bond or one or a combination of the following groups:

[0145]

[0146]

[0147] The R s One selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0148] The R vthe same or different ones selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, or a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

[0149] R7 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring, or a combination thereof;

[0150] wherein R0 is selected from 0, 1 or 2; R4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; R5 is selected from 0, 1, 2 or 3; R6 is selected from 0 or 1; R7 is selected from 0, 1, 2, 3, 4 or 5; R8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R7s are present, the two or more R7s are the same or different from each other, or two adjacent R7s are connected to form a substituted or unsubstituted ring;

[0151] Preferably, the R sselected from hydrogen, deuterium, tritium, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted dihydroindanyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptanyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof, or two adjacent R s are connected to each other to form a substituted or unsubstituted ring;

[0152] Preferably, the R vselected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof, or two adjacent R v are connected to each other to form a substituted or unsubstituted ring;

[0153] Preferably, R7 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof.

[0154] Most preferably, the triarylamine derivative based on fluorenyl heterocycle is selected from at least one of the following structures:

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] The above lists some specific structural forms of the fluorenyl heterocyclic triarylamine derivatives represented by Chemical Formula I of the present invention. However, the present invention is not limited to these listed chemical structures. All derivatives based on the structure shown in Chemical Formula I and having substituents as defined above are included.

[0176] The present invention also provides an organic electroluminescent device, which comprises at least one of the triarylamine derivatives based on fluorenyl heterocycles described in the present invention.

[0177] Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode or on the outside of one or more electrodes of the anode and the cathode, and the organic layer comprises at least one of the triarylamine derivatives based on fluorenyl heterocycles described in the present invention.

[0178] More preferably, the organic electroluminescent device of the present invention may include one or more organic layers, which may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a capping layer. Specifically, the organic layer located between the anode and the cathode may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and the like. The organic layer located outside one or more of the anode and cathode electrodes may include a capping layer, etc. The organic layer may be formed by a single-layer structure or a multi-layer structure of stacked organic layers. At the same time, each organic layer may also include one or more multi-layer structures. For example, the hole transport layer includes a first hole transport layer and a second hole transport layer. However, the structure of the organic electroluminescent device is not limited to this and may include fewer or more organic layers.

[0179] Further preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport layer, and the hole transport layer comprises at least one of the triarylamine derivatives based on fluorenyl heterocycles described in the present invention.

[0180] Most preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, and at least one of the first hole transport layer and the second hole transport layer comprises at least one of the triarylamine derivatives based on fluorenyl heterocycles described in the present invention.

[0181] The anode material of the present invention is preferably a material with a high work function. The anode can be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited thereto.

[0182] The hole injection layer material described in the present invention is preferably a material with a high work function, which can be selected from any one or more of the following structures: metal porphyrins, oligothiophenes, aromatic amine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers, but is not limited thereto. Preferably, the hole injection layer material can be selected from 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (abbreviated as: 2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as: MTDATA), copper phthalocyanine (II) (abbreviated as: CuPc), N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-biphenyl-4,4'-diamine (abbreviated as: DNTPD), etc. It can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances.

[0183] The hole transport layer of the present invention may include a first hole transport layer material and a second hole transport layer material, preferably a material having high hole mobility. In addition to the triarylamine derivatives based on fluorenyl heterocycles described in the present invention, any one or more of the following structures may be selected: carbazole derivatives, triarylamine derivatives, biphenylenediamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but are not limited thereto.

[0184] The light-emitting layer material of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, and may use two host materials to form a dual host material. The guest material may be a fluorescent compound, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazole vinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)picolinoyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), etc. The host material preferably uses a substance having a higher LUMO and a lower HOMO than that of the guest material, such as a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative or a benzimidazole derivative, a fused aromatic compound such as a carbazole derivative or anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative, examples of which 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-benzimidazol-2-yl)benzene (TPBI), TPD, 4,4'-di(9-carbazole)biphenyl (CBP), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), and 9,10-di(2-naphthyl)anthracene (ADN), but are not limited thereto.

[0185] The hole blocking layer material of the present invention is preferably a material that can effectively block holes, and can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, etc., but is not limited thereto.

[0186] The electron transport layer material described in the present invention is preferably a material with high electron mobility, which can be selected from any one or more of the following structures: metal chelates, oxazolidinone derivatives, thiazole derivatives, diazole derivatives, azabenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but is not limited to these. It can be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances.

[0187] The electron injection layer material of the present invention preferably has a low work function and can be selected from any one or more of the following structures: metals, 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, metal complexes, and other substances with high electron injection properties. Examples include, but are not limited to, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, 8-hydroxyquinoline cesium, tris(8-hydroxyquinoline)aluminum, and the like.

[0188] The cathode of the present invention preferably has a material with a low work function, and the cathode can be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but are not limited thereto.

[0189] The covering layer of the present invention includes a first covering layer and / or a second covering layer. When the first covering layer or the second covering 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 covering layer and the second covering layer are included, it can be a multi-layer structure composed of a single substance or different substances. The covering layer material can be organic or inorganic, for example, it can be metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsC l , CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, but not limited to these.

[0190] The organic layers, cathode, anode, and capping layer can be formed using any of the following methods: vacuum deposition, inkjet printing, sputtering, plasma deposition, spin coating, dipping, or screen printing. The thickness of each layer is not particularly limited, provided that good device performance is achieved. The organic layers are preferably formed using, but are not limited to, vacuum deposition, inkjet printing, or spin coating.

[0191] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, specifically lighting light sources, smartphone displays, tablet computer displays, organic solar cells, smart wearable device displays, VR, vehicle-mounted systems, and automobile taillights.

[0192] Preparation and characterization of compounds

[0193] Description of raw materials, reagents and characterization equipment:

[0194] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. They may be commercially available products or prepared using methods well known to those skilled in the art.

[0195] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0196] Elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5–10 mg;

[0197] The following is a method for preparing the compound represented by Chemical Formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of Chemical Formula I can be prepared by the reaction scheme shown below, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc., and the type and position of the substituent or the number of the substituents can be changed according to techniques known in the art.

[0198] Synthesis route

[0199] Preparation of compounds of formula I:

[0200]

[0201] The X1 to X2 are independently selected from any one of I, Br, and Cl; the definitions of W, Ar1 to Ar2, L0, and L1 to L2 are the same as those above.

[0202] Synthesis Example 1: Preparation of Intermediate B-3

[0203]

[0204] Preparation of intermediate A-3:

[0205] Under nitrogen, a-3 (35.47 g, 180.00 mmol) was dissolved in 165 ml of anhydrous tetrahydrofuran. The solution was maintained at -78°C, and 75 ml of a 2.5 M n-butyllithium hexane solution was slowly added dropwise. After the addition was complete, the mixture was stirred for 3 h. b-3 (19.36 g, 180.00 mmol) was dissolved in 270 ml of tetrahydrofuran and slowly added dropwise. The reaction solution was maintained at -78°C and stirred for 1.5 h. Dilute hydrochloric acid was added to terminate the reaction, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure. The mixture was purified by silica gel column chromatography (petroleum ether:dichloromethane = 6:1) to obtain intermediate A-3 (30.99 g, 91% yield); HPLC purity ≥99.79%. Mass spectrum: m / z: 189.0778 (theoretical value: 189.0790).

[0206] Preparation of intermediate B-3:

[0207] Under nitrogen, 106.25 ml of a 1.6 M methyllithium solution in diethyl ether was added to the reaction flask. The solution was maintained at -78°C, and 68 ml of a 2.5 M n-butyllithium solution in hexane was slowly added dropwise. After the addition was complete and the mixture was stirred for 1 hour, A-3 (32.17 g, 170.00 mmol) was dissolved in 245 ml of tetrahydrofuran and slowly added dropwise. The reaction solution was warmed from -78°C to 0°C and stirred. Dilute hydrochloric acid was added to terminate the reaction, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate = 7:1) to obtain B-3 (18.79 g, 69% yield); HPLC purity ≥99.83%. Mass spectrum: m / z: 160.0540 (theoretical value: 160.0524).

[0208] Synthesis Example 2: Preparation of Intermediate B-14

[0209]

[0210] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-14 to obtain Intermediate B-14 (18.24 g). The solid purity was ≥99.87% as determined by HPLC. Mass spectrum: m / z: 160.0511 (theoretical value: 160.0524).

[0211] Synthesis Example 3: Preparation of Intermediate B-16

[0212]

[0213] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-16 to obtain Intermediate B-16 (19.06 g). The solid purity was ≥99.84% as determined by HPLC. Mass spectrum: m / z: 160.0537 (theoretical value: 160.0524).

[0214] Synthesis Example 4: Preparation of Intermediate B-27

[0215]

[0216] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-27 to obtain Intermediate B-27 (21.17 g). The solid purity was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 194.0122 (theoretical value: 194.0135).

[0217] Synthesis Example 5: Preparation of Intermediate B-42

[0218]

[0219] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-42 to obtain Intermediate B-42 (17.97 g). The solid purity was ≥99.83% as determined by HPLC. Mass spectrum: m / z: 160.0536 (theoretical value: 160.0524).

[0220] Synthesis Example 6: Preparation of Intermediate B-51

[0221]

[0222] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-51 to obtain Intermediate B-51 (22.50 g). The solid purity was ≥99.87% as determined by HPLC. Mass spectrum: m / z: 194.0150 (theoretical value: 194.0135).

[0223] Synthesis Example 7: Preparation of Intermediate B-101

[0224]

[0225] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-101 to obtain Intermediate B-101 (19.47 g). The solid purity was ≥99.82% as determined by HPLC. Mass spectrum: m / z: 176.0284 (theoretical value: 176.0296).

[0226] Synthesis Example 8: Preparation of Intermediate B-250

[0227]

[0228] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-250 to obtain Intermediate B-250 (25.81 g). The solid purity was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 237.0779 (theoretical value: 237.0790).

[0229] Synthesis Example 9: Preparation of Intermediate B-350

[0230]

[0231]

[0232] Preparation of intermediate A'-350:

[0233] Under nitrogen protection, a'-350 (31.40 g, 200 mmol) was dissolved in 180 ml of anhydrous tetrahydrofuran. 80 ml of 2.5 M n-butyl hexane solution was slowly added dropwise to the solution at -78°C, and then stirred for 3 h to obtain a tetrahydrofuran solution of A'-350.

[0234] Preparation of intermediate B-350:

[0235] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-350 (25.31 g). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 222.0669 (theoretical value: 222.0681).

[0236] Synthesis Example 10: Preparation of Intermediate B-357

[0237]

[0238] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-42, and methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-357 (25.69 g). HPLC analysis of the solid showed a purity of ≥99.87%. Mass spectrum: m / z: 222.0694 (theoretical value: 222.0681).

[0239] Synthesis Example 11: Preparation of Intermediate B-378

[0240]

[0241] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-378, and methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-378 (28.80 g). HPLC analysis of the solid showed a purity of ≥99.82%. Mass spectrum: m / z: 256.0301 (theoretical value: 256.0291).

[0242] Synthesis Example 12: Preparation of Intermediate B-383

[0243]

[0244] Preparation of intermediate A'-383:

[0245] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a'-383 to obtain a tetrahydrofuran solution of A'-383.

[0246] Preparation of intermediate B-383:

[0247] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, methyllithium was replaced with an equal molar amount of A'-383 to obtain Intermediate B-383 (29.67 g). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrum m / z: 256.0280 (theoretical value: 256.0291).

[0248] Synthesis Example 13: Preparation of Intermediate B-388

[0249]

[0250] Preparation of intermediate A'-388:

[0251] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal mole of a'-388 to obtain a tetrahydrofuran solution of A'-388.

[0252] Preparation of intermediate B-388:

[0253] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-16, and methyllithium was replaced with an equal molar amount of A'-388 to obtain Intermediate B-388 (33.37 g). HPLC analysis of the solid showed a purity of ≥99.86%. Mass spectrum: m / z: 306.0460 (theoretical value: 306.0448).

[0254] Synthesis Example 14: Preparation of Intermediate B-397

[0255]

[0256] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-42, and methyllithium was replaced with an equal molar amount of A'-391 to obtain Intermediate B-397 (28.80 g). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrum: m / z: 256.0280 (theoretical value: 256.0291).

[0257] Synthesis Example 15: Preparation of Intermediate B-402

[0258]

[0259] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-402, and methyllithium was replaced with an equal molar amount of A'-391 to obtain Intermediate B-402 (35.46 g). HPLC analysis of the solid showed a purity of ≥99.83%. Mass spectrum: m / z: 306.0460 (theoretical value: 306.0448).

[0260] Synthesis Example 16: Preparation of Intermediate B-417

[0261]

[0262]

[0263] Preparation of intermediate A'-417:

[0264] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a'-417 to obtain a tetrahydrofuran solution of A'-417.

[0265] Preparation of intermediate B-417:

[0266] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, methyllithium was replaced with an equal molar amount of A'-417 to obtain Intermediate B-417 (30.58 g). The solid purity was ≥99.89% as determined by HPLC. Mass spectrum m / z: 260.0555 (theoretical value: 260.0542).

[0267] Synthesis Example 17: Preparation of Intermediate B-434

[0268]

[0269] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 2, intermediate B-434 (28.36 g) was obtained by replacing a-3 with an equal molar amount of a-434 and replacing methyllithium with an equal molar amount of A'-350. The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 256.0303 (theoretical value: 256.0291).

[0270] Synthesis Example 18: Preparation of Intermediate B-450

[0271]

[0272] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-450, and methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-450 (28.36 g). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrum: m / z: 238.0440 (theoretical value: 238.0452).

[0273] Synthesis Example 19: Preparation of Intermediate B-521

[0274]

[0275] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-101, and methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-521 (27.14 g). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrum m / z: 238.0441 (theoretical value: 238.0452).

[0276] Synthesis Example 20: Preparation of Intermediate B-566

[0277]

[0278]

[0279] Preparation of intermediate A'-566:

[0280] According to the same preparation method as that of intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-3 to obtain a tetrahydrofuran solution of A'-566.

[0281] Preparation of intermediate B-566:

[0282] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, methyllithium was replaced with an equal molar amount of A'-566 to obtain Intermediate B-566 (28.53 g). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrum m / z: 262.0644 (theoretical value: 262.0630).

[0283] Synthesis Example 21: Preparation of Intermediate B-571

[0284]

[0285] Preparation of intermediate A'-571:

[0286] According to the same preparation method as that of intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-42 to obtain a tetrahydrofuran solution of A'-571.

[0287] Preparation of intermediate B-571:

[0288] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-42, and methyllithium was replaced with an equal molar amount of A'-571 to obtain Intermediate B-571 (30.32 g). The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrum: m / z: 262.0641 (theoretical value: 262.0630).

[0289] Synthesis Example 22: Preparation of Intermediate B-573

[0290]

[0291] Preparation of intermediate A'-573:

[0292] According to the same preparation method as that of intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-16 to obtain a tetrahydrofuran solution of A'-573.

[0293] Preparation of intermediate B-573:

[0294] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, methyllithium was replaced with an equal molar amount of A'-573 to obtain Intermediate B-573 (30.32 g). The purity of the solid was ≥99.82% as determined by HPLC. Mass spectrum: m / z: 262.0617 (theoretical value: 262.0630).

[0295] Synthesis Example 23: Preparation of Intermediate B-588

[0296]

[0297] Preparation of intermediate A'-588:

[0298] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a'-588 to obtain a tetrahydrofuran solution of A'-588.

[0299] Preparation of intermediate B-588:

[0300] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-42, and methyllithium was replaced with an equal molar amount of A'-588 to obtain Intermediate B-588 (31.78 g). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrum: m / z: 296.0252 (theoretical value: 296.0240).

[0301] Synthesis Example 24: Preparation of Intermediate B-604

[0302]

[0303] Preparation of intermediate A'-604:

[0304] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-604 to obtain a tetrahydrofuran solution of A'-604.

[0305] Preparation of intermediate B-604:

[0306] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, except that a-3 was replaced with an equal molar amount of a-604 and methyllithium was replaced with an equal molar amount of A'-604, intermediate B-604 (34.53 g) was obtained. The purity of the solid was ≥99.85% as determined by HPLC. Mass spectrum: m / z: 294.0185 (theoretical value: 294.0173).

[0307] Synthesis Example 25: Preparation of Intermediate B-647

[0308]

[0309]

[0310] Preparation of intermediate A'-647:

[0311] According to the same preparation method as that of the intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-647 to obtain a tetrahydrofuran solution of A'-647.

[0312] Preparation of intermediate B-647:

[0313] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, intermediate B-647 (37.58 g) was obtained by replacing a-3 with an equal molar amount of a-647 and methyllithium with an equal molar amount of A'-647. HPLC analysis of the solid showed a purity of ≥99.83%. Mass spectrum: m / z: 362.0956 (theoretical value: 362.0943).

[0314] Synthesis Example 26: Preparation of Intermediate B-673

[0315]

[0316] Preparation of intermediate A'-673:

[0317] According to the same preparation method as that of intermediate A'-350 in Synthesis Example 9, a'-350 was replaced with an equal molar amount of a-450 to obtain a tetrahydrofuran solution of A'-673.

[0318] Preparation of intermediate B-673:

[0319] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-450, and methyllithium was replaced with an equal molar amount of A'-673 to obtain Intermediate B-673 (33.03 g). HPLC analysis of the solid showed a purity of ≥99.84%. Mass spectrum: m / z: 294.0161 (theoretical value: 294.0173).

[0320] Synthesis Example 27: Preparation of Intermediate B-716

[0321]

[0322] Following the same preparation method as that of Intermediate B-3 in Synthesis Example 1, a-3 was replaced with an equal molar amount of a-716, and methyllithium was replaced with an equal molar amount of A'-350 to obtain Intermediate B-716 (33.24 g). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrum: m / z: 315.0730 (theoretical value: 315.0718).

[0323] Synthesis Example 28: Preparation of Compound 3

[0324]

[0325] Preparation of intermediate C-3:

[0326] C-3 (39.49 g, 110.00 mmol) was dissolved in 205 ml of anhydrous tetrahydrofuran. Under nitrogen, the temperature of the solution was maintained at -78°C. 44 ml of a 2.5 M hexane solution of n-butyllithium was slowly added dropwise to the solution. After the addition was complete, the mixture was stirred for 1 hour. B-3 (17.62 g, 110.00 mmol) was then dissolved in 138 ml of tetrahydrofuran and slowly added dropwise. The reaction solution was maintained at -78°C and stirred for 2 hours. The mixture was then allowed to reach room temperature and stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in glacial acetic acid (165 ml). Concentrated hydrochloric acid solution (31%, 16.5 ml) was added, and the mixture was reacted under reflux for 4.5 hours and stirred at room temperature overnight. After the reaction, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent removed under reduced pressure. The mixture was recrystallized from isopropanol to obtain intermediate C-3 (30.55 g, 74% yield); HPLC purity ≥99.84%. Mass spectrum m / z: 374.0320 (theoretical value: 374.0306).

[0327] Preparation of intermediate D-3:

[0328] Under nitrogen, C-3 (18.76 g, 50.00 mmol), M-3 (9.31 g, 55.00 mmol), palladium acetate (0.12 g, 0.55 mmol), tri-tert-butylphosphine (0.22 g, 1.10 mmol), sodium tert-butoxide (6.25 g, 65.00 mmol), and toluene (450 ml) were added to a reaction flask and stirred at reflux for 7 h. The mixture was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from ethyl acetate / petroleum ether (3:1) to give D-3 (16.23 g, 70% yield); HPLC purity ≥99.87%. Mass spectrum: m / z: 463.1951 (theoretical value: 463.1936).

[0329] Preparation of compound 3:

[0330] Under nitrogen, D-3 (13.91 g, 30.00 mmol), e-3 (7.41 g, 30.00 mmol), sodium tert-butoxide (3.46 g, 36.00 mmol), trisdibenzylideneacetone dipalladium (0.27 g, 0.30 mmol), tri-tert-butylphosphine (0.12 g, 0.60 mmol), and toluene (200 ml) were added to a reaction flask and reacted under reflux for 8 h. After the reaction, the mixture was cooled to room temperature, water was added, and the organic phase was separated and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was recrystallized from toluene / ethanol (4:1) to obtain compound 3 (14.93 g, 79% yield); HPLC purity ≥99.97%. Mass spectrum m / z: 629.2369 (theoretical value: 629.2355). Theoretical element content (%): C 46 H 31 NO2: C, 87.73; H, 4.96; N, 2.22. Measured element content (%): C, 87.78; H, 5.00; N, 2.19.

[0331] Synthesis Example 29: Preparation of Compound 14

[0332]

[0333] Following the same preparation method as that used in Example 28 for compound 3, B-3 was replaced with an equal molar amount of B-14, and M-3 was replaced with an equal molar amount of M-14 to obtain compound 14 (14.95 g). HPLC analysis revealed a solid purity of ≥99.93%. Mass spectrum: m / z: 638.2907 (theoretical value: 638.2920). Theoretical element content (%): C 46 H 22 D9NO2: C, 86.49; H, 6.31; N, 2.19. Measured element content (%): C, 86.54; H, 6.27; N, 2.22. Synthesis Example 30: Preparation of Compound 16

[0334]

[0335] Compound 16 (16.32 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-16 and M-3 was replaced with an equal molar amount of M-16. HPLC analysis revealed a solid purity of ≥99.96%. Mass spectrum: m / z: 679.2523 (theoretical value: 679.2511). Theoretical element content (%): C 50 H 33 NO2: C, 88.34; H, 4.89; N, 2.06. Measured element content (%): C, 88.39; H, 4.92; N, 2.09.

[0336] Synthesis Example 31: Preparation of Compound 27

[0337]

[0338] Compound 27 (15.10 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-27, C-3 was replaced with an equal molar amount of C-27, M-3 was replaced with an equal molar amount of M-27, and e-3 was replaced with an equal molar amount of e-27. HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrum m / z: 653.2342 (theoretical value: 653.2355). Theoretical element content (%): C 48 H 31 NO2: C, 88.18; H, 4.78; N, 2.14. Measured element content (%): C, 88.23; H, 4.82; N, 2.09.

[0339] Synthesis Example 32: Preparation of Compound 42

[0340]

[0341] Preparation of intermediate M-42:

[0342] Under nitrogen, m-42 (21.68 g, 110.00 mmol), n-42 (15.06 g, 110.00 mmol), K2CO3 (27.36 g, 198.00 mmol), Pd(PPh3)4 (1.27 g, 1.10 mmol), 320 ml of ethanol, and 320 ml of water were added to 960 ml of toluene. The mixture was stirred and heated under reflux for 6.5 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 mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from toluene / methanol (volume ratio 9:1) to obtain intermediate M-42 (17.50 g, yield 76%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrum m / z: 209.1216 (theoretical value: 209.1204).

[0343] Preparation of compound 42:

[0344] Following the same preparation method as in Example 28, Compound 3 was prepared by replacing B-3 with an equal molar amount of B-42 and M-3 with an equal molar amount of M-42 to obtain Compound 42 (15.87 g). HPLC analysis revealed a solid purity of ≥99.98%. Mass spectrum: m / z: 669.2680 (theoretical value: 669.2668). Theoretical element content (%): C 49 H 35NO2: C, 87.86; H, 5.27; N, 2.09. Measured element content (%): C, 87.91; H, 5.23; N, 2.12.

[0345] Synthesis Example 33: Preparation of Compound 44

[0346]

[0347] Following the same preparation method as in Example 28, Compound 3 was synthesized, with M-3 replaced by an equal molar amount of M-44 and e-3 replaced by an equal molar amount of e-27 to obtain Compound 44 (15.29 g). HPLC analysis revealed a solid purity of ≥99.92%. Mass spectrum: m / z: 670.2380 (theoretical value: 670.2367). Theoretical element content (%): C 48 H 30 DNO3: C, 85.95; H, 4.81; N, 2.09. Measured element content (%): C, 85.90; H, 4.77; N, 2.12.

[0348] Synthesis Example 34: Preparation of Compound 51

[0349]

[0350] Preparation of intermediate C-51:

[0351] C-27 (30.81 g, 110.00 mmol) was dissolved in 205 ml of anhydrous tetrahydrofuran. Under nitrogen, the temperature of the solution was maintained at -78°C. 44 ml of a 2.5 M hexane solution of n-butyllithium was slowly added dropwise to the solution. After the addition was complete, the mixture was stirred for 1 hour. B-51 (21.41 g, 110.00 mmol) was then dissolved in 138 ml of tetrahydrofuran and slowly added dropwise. The reaction solution was maintained at -78°C and stirred for 1 hour. The mixture was then allowed to reach room temperature and stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in glacial acetic acid (165 ml). Concentrated hydrochloric acid solution (31%, 16.5 ml) was added, and the mixture was reacted under reflux for 4 hours and stirred at room temperature overnight. After the reaction, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent removed under reduced pressure. The mixture was recrystallized from isopropanol to obtain intermediate C-51 (26.56 g, 73% yield); HPLC purity ≥99.85%. Mass spectrum m / z: 330.0824 (theoretical value: 330.0811).

[0352] Preparation of intermediate E-51:

[0353] Under nitrogen, intermediate C-51 (24.81 g, 75.00 mmol), d-51 (15.06 g, 75.00 mmol), Pd(PPh3)4 (0.87 g, 0.75 mmol), K2CO3 (20.73 g, 150.00 mmol), 300 mL of ethanol, and 300 mL of water were added to 900 mL of toluene. The mixture was stirred and heated under reflux for 6 h. After the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake, which was rinsed with ethanol and recrystallized from toluene to obtain intermediate E-51 (24.04 g, 71% yield). HPLC analysis of the solid revealed a purity of ≥99.87%. Mass spectrum: m / z: 450.0633 (theoretical value: 450.0619).

[0354] Preparation of intermediate D-51:

[0355] Under nitrogen, E-51 (22.57 g, 50.00 mmol), M-51 (9.5 g, 55.00 mmol), palladium acetate (0.12 g, 0.55 mmol), tri-tert-butylphosphine (0.22 g, 1.10 mmol), sodium tert-butoxide (10.57 g, 110.00 mmol), and toluene (440 ml) were added to a reaction flask and stirred at reflux for 8 h. The mixture was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from ethyl acetate / petroleum ether (3:1) to obtain D-51 (27.24 g, 72% yield); HPLC purity ≥99.89%. Mass spectrum: m / z: 544.2576 (theoretical value: 544.2563).

[0356] Preparation of compound 51:

[0357] Under nitrogen, D-51 (16.34 g, 30.00 mmol), e-3 (7.4 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), trisdibenzylideneacetone dipalladium (0.2 g, 0.30 mmol), tri-tert-butylphosphine (0.12 g, 0.60 mmol), and toluene (200 ml) were added to a reaction flask and reacted under reflux for 9 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the organic phase was separated and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was recrystallized from toluene / ethanol (4:1) to obtain compound 51 (17.06 g, 80% yield); HPLC purity ≥99.95%. Mass spectrum m / z: 710.2970 (theoretical value: 710.2982). Theoretical element content (%): C 52 H 30D5NO2: C, 87.86; H, 5.67; N, 1.97. Measured element content (%): C, 87.91; H, 5.71; N, 2.00.

[0358] Synthesis Example 35: Preparation of Compound 77

[0359]

[0360] Preparation of intermediate M-77:

[0361] Following the same preparation method as that of intermediate M-42 in Synthesis Example 32, intermediate M-77 (22.09 g) was obtained by replacing intermediate M-42 with an equal molar amount of m-77. The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrum: m / z: 271.1123 (theoretical value: 271.1109).

[0362] Preparation of compound 77:

[0363] Compound 77 (18.17 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-42, c-3 was replaced with an equal molar amount of c-77, M-3 was replaced with an equal molar amount of M-77, and e-3 was replaced with an equal molar amount of e-27. HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrum m / z: 747.2356 (theoretical value: 747.2344). Theoretical element content (%): C 52 H 33 N3OS: C, 83.51; H, 4.45; N, 5.62. Measured element content (%): C, 83.46; H, 4.49; N, 5.59.

[0364] Synthesis Example 36: Preparation of Compound 101

[0365]

[0366] Compound 101 (18.79 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-101, M-3 was replaced with an equal molar amount of M-101, and e-3 was replaced with an equal molar amount of e-101. HPLC analysis of the solid showed a purity of ≥99.91%. Mass spectrum m / z: 834.3130 (theoretical value: 834.3117). Theoretical element content (%): C 58 H 34 D7NOSSi: C, 83.41; H, 5.79; N, 1.68. Measured element content (%): C, 83.36; H, 5.83; N, 1.71.

[0367] Synthesis Example 37: Preparation of Compound 197

[0368]

[0369] Compound 197 (17.25 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-16, M-3 was replaced with an equal molar amount of M-197, and e-3 was replaced with an equal molar amount of e-197. The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum: m / z: 746.3310 (theoretical value: 746.3297). Theoretical element content (%): C 55 H 42 N2O: C, 88.44; H, 5.67; N, 3.75. Measured element content (%): C, 88.39; H, 5.71; N, 3.72.

[0370] Synthesis Example 38: Preparation of Compound 250

[0371]

[0372] Compound 250 (16.87 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-250 and M-3 was replaced with an equal molar amount of M-250. HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum m / z: 711.2921 (theoretical value: 711.2934). Theoretical element content (%): C 51 H 29 D5N2O2: C, 86.05; H, 5.52; N, 3.94. Measured element content (%): C, 86.00; H, 5.48; N, 3.97.

[0373] Synthesis Example 39: Preparation of Compound 350

[0374]

[0375] Compound 350 (15.64 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-350 and M-3 was replaced with an equal molar amount of M-350. HPLC analysis of the solid showed a purity of ≥99.98%. Mass spectrum m / z: 620.2501 (theoretical value: 620.2512). Theoretical element content (%): C 45 H 24 D5NO2: C, 87.07; H, 5.52; N, 2.26. Measured element content (%): C, 87.12; H, 5.47; N, 2.30.

[0376] Synthesis Example 40: Preparation of Compound 357

[0377]

[0378] Following the same preparation method as compound 3 in Example 28, B-3 was replaced with an equal molar amount of B-357 to obtain compound 357 (17.02 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 691.2525 (theoretical value: 691.2511). Theoretical element content (%): C 51 H 33 NO2: C, 88.54; H, 4.81; N, 2.02. Measured element content (%): C, 88.49; H, 4.77; N, 1.99.

[0379] Synthesis Example 41: Preparation of Compound 368

[0380]

[0381] Preparation of intermediate M-368:

[0382] Following the same preparation method as that of intermediate M-42 in Synthesis Example 32, intermediate M-368 (20.71 g) was obtained by replacing m-42 with an equal molar amount of m-368. The purity of the solid was ≥99.89% as determined by HPLC. Mass spectrum: m / z: 241.1275 (theoretical value: 241.1287).

[0383] Preparation of compound 368:

[0384] Following the same preparation method as in Example 28, Compound 3 was prepared by replacing B-3 with an equal molar amount of B-357 and M-3 with an equal molar amount of M-368 to obtain Compound 368 (17.42 g). HPLC analysis revealed a solid purity of ≥99.95%. Mass spectrum: m / z: 763.2923 (theoretical value: 763.2907). Theoretical element content (%): C 54 H 41 NO2Si: C, 84.89; H, 5.41; N, 1.83. Measured element content (%): C, 84.94; H, 5.37; N, 1.80.

[0385] Synthesis Example 42: Preparation of Compound 371

[0386]

[0387] Preparation of intermediate M-371:

[0388] Following the same preparation method as that of intermediate M-42 in Synthesis Example 32, intermediate M-371 (25.70 g) was obtained by replacing m-42 with an equal molar amount of m-371. The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrum: m / z: 303.1998 (theoretical value: 303.1987).

[0389] Preparation of compound 371:

[0390] Compound 371 (18.59 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-357 and M-3 was replaced with an equal molar amount of M-371. HPLC analysis of the solid showed a purity of ≥99.93%. Mass spectrum m / z: 825.3621 (theoretical value: 825.3607). Theoretical element content (%): C 61 H 47 NO2: C, 88.70; H, 5.74; N, 1.70. Measured element content (%): C, 88.65; H, 5.70; N, 1.73.

[0391] Synthesis Example 43: Preparation of Compound 378

[0392]

[0393] Compound 378 (17.74 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-378 and M-3 was replaced with an equal molar amount of M-378. HPLC analysis of the solid showed a purity of ≥99.93%. Mass spectrum m / z: 767.2840 (theoretical value: 767.2824). Theoretical element content (%): C 57 H 37 NO2: C, 89.15; H, 4.86; N, 1.82. Measured element content (%): C, 89.20; H, 4.90; N, 1.79.

[0394] Synthesis Example 44: Preparation of Compound 383

[0395]

[0396] Following the same preparation method as in Example 28, Compound 3 was prepared by replacing B-3 with an equal molar amount of B-383 and C-3 with an equal molar amount of C-27 to obtain Compound 383 (17.02 g). HPLC analysis revealed a solid purity of ≥99.96%. Mass spectrum: m / z: 691.2524 (theoretical value: 691.2511). Theoretical element content (%): C 51 H 33NO2: C, 88.54; H, 4.81; N, 2.02. Measured element content (%): C, 88.49; H, 4.78; N, 1.98.

[0397] Synthesis Example 45: Preparation of Compound 388

[0398]

[0399] Compound 388 (18.37 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-388, C-3 was replaced with an equal molar amount of C-27, and M-3 was replaced with an equal molar amount of M-388. The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum: m / z: 755.2448 (theoretical value: 755.2460). Theoretical element content (%): C 55 H 33 NO3: C, 87.40; H, 4.40; N, 1.85. Measured element content (%): C, 87.35; H, 4.44; N, 1.88.

[0400] Synthesis Example 46: Preparation of Compound 391

[0401]

[0402] Compound 391 (18.77 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-383, C-3 was replaced with an equal molar amount of C-391, and M-3 was replaced with an equal molar amount of M-391. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 833.3340 (theoretical value: 833.3328). Theoretical element content (%): C 59 H 47 NO2S: C, 84.96; H, 5.68; N, 1.68. Measured element content (%): C, 85.01; H, 5.72; N, 1.65.

[0403] Synthesis Example 47: Preparation of Compound 393

[0404]

[0405] Compound 393 (16.82 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-350 and M-3 was replaced with an equal molar amount of M-393. The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 700.3063 (theoretical value: 700.3076). Theoretical element content (%): C 51 H 24D9NO2: C, 87.40; H, 6.04; N, 2.00. Measured element content (%): C, 87.35; H, 5.99; N, 1.96.

[0406] Synthesis Example 48: Preparation of Compound 397

[0407]

[0408] Compound 397 (18.27 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-397, C-3 was replaced with an equal molar amount of C-27, and M-3 was replaced with an equal molar amount of M-397. HPLC analysis of the solid showed a purity of ≥99.92%. Mass spectrum: m / z: 780.2791 (theoretical value: 780.2777). Theoretical element content (%): C 57 H 36 N2O2: C, 87.67; H, 4.65; N, 3.59. Measured element content (%): C, 87.72; H, 4.61; N, 3.62.

[0409] Synthesis Example 49: Preparation of Compound 402

[0410]

[0411] Compound 402 (17.96 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-402, c-3 was replaced with an equal molar amount of c-27, M-3 was replaced with an equal molar amount of M-402, and e-3 was replaced with an equal molar amount of e-77. HPLC analysis revealed a solid purity of ≥99.96%. Mass spectrum: m / z: 757.2451 (theoretical value: 757.2439). Theoretical element content (%): C 55 H 35 NOS: C, 87.16; H, 4.65; N, 1.85. Measured element content (%): C, 87.21; H, 4.61; N, 1.88.

[0412] Synthesis Example 50: Preparation of Compound 407

[0413]

[0414] Compound 407 (18.09 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-387, M-3 was replaced with an equal molar amount of M-407, and e-3 was replaced with an equal molar amount of e-407. HPLC analysis of the solid showed a purity of ≥99.92%. Mass spectrum: m / z: 782.2402 (theoretical value: 782.2392). Theoretical element content (%): C56 H 34 N2OS: C, 85.91; H, 4.38; N, 3.58. Measured element content (%): C, 85.96; H, 4.34; N, 3.61.

[0415] Synthesis Example 51: Preparation of Compound 417

[0416]

[0417] Compound 417 (16.66 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-417, C-3 was replaced with an equal molar amount of C-27, and E-3 was replaced with an equal molar amount of E-77. The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrum: m / z: 711.2522 (theoretical value: 711.2534). Theoretical element content (%): C 51 H 29 D4NOS: C, 86.04; H, 5.24; N, 1.97. Measured element content (%): C, 85.99; H, 5.28; N, 2.00.

[0418] Synthesis Example 52: Preparation of Compound 434

[0419]

[0420] Preparation of intermediate M-434:

[0421] Following the same preparation method as that of intermediate M-42 in Synthesis Example 32, intermediate M-434 (24.71 g) was obtained by replacing m-42 with an equal molar amount of m-434. The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrum: m / z: 284.1303 (theoretical value: 284.1313).

[0422] Preparation of compound 434:

[0423] Compound 434 (18.52 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-434, C-3 was replaced with an equal molar amount of C-27, M-3 was replaced with an equal molar amount of M-434, and E-3 was replaced with an equal molar amount of E-77. HPLC analysis revealed a solid purity of ≥99.93%. Mass spectrum: m / z: 822.2716 (theoretical value: 822.2705). Theoretical element content (%): C 59 H 38 N2OS: C, 86.10; H, 4.65; N, 3.40. Measured element content (%): C, 86.05; H, 4.69; N, 3.37.

[0424] Synthesis Example 53: Preparation of Compound 450

[0425]

[0426] Following the same preparation method as compound 3 in Example 28, B-3 was replaced with an equal molar amount of B-450 to obtain compound 450 (16.78 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 707.2296 (theoretical value: 707.2283). Theoretical element content (%): C 51 H 33 NOS: C, 86.53; H, 4.70; N, 1.98. Measured element content (%): C, 86.48; H, 4.66; N, 2.01.

[0427] Synthesis Example 54: Preparation of Compound 521

[0428]

[0429] Compound 521 (17.78 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-521, c-3 was replaced with an equal molar amount of c-77, M-3 was replaced with an equal molar amount of M-521, and e-3 was replaced with an equal molar amount of e-77. HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum m / z: 779.1764 (theoretical value: 779.1775). Theoretical element content (%): C 53 H 33 NS3: C, 81.61; H, 4.26; N, 1.80. Measured element content (%): C, 81.56; H, 4.30; N, 1.77.

[0430] Synthesis Example 55: Preparation of Compound 543

[0431]

[0432] Following the same preparation method as in Example 28, Compound 3 was prepared by replacing B-3 with an equal molar amount of B-350 and e-3 with an equal molar amount of e-543 to obtain Compound 543 (18.97 g). HPLC analysis revealed a solid purity of ≥99.98%. Mass spectrum: m / z: 842.3284 (theoretical value: 842.3297). Theoretical element content (%): C 63 H 42 N2O: C, 89.76; H, 5.02; N, 3.32. Measured element content (%): C, 89.81; H, 4.98; N, 3.35.

[0433] Synthesis Example 56: Preparation of Compound 556

[0434]

[0435] Preparation of intermediate e-556:

[0436] Under nitrogen, intermediate f-556 (40.95 g, 110.00 mmol), d-51 (22.09 g, 110.00 mmol), Pd(PPh3)4 (1.27 g, 1.10 mmol), K2CO3 (30.41 g, 220.00 mmol), 300 mL of ethanol, and 300 mL of water were added to 900 mL of toluene. The mixture was stirred and heated under reflux for 6 h. After the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake, which was rinsed with ethanol and recrystallized from toluene to obtain intermediate e-556 (34.52 g, 70% yield). HPLC analysis of the solid revealed a purity of ≥99.86%. Mass spectrum: m / z: 447.0637 (theoretical value: 447.0623).

[0437] Preparation of compound 556:

[0438] Compound 556 (19.34 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-450, M-3 was replaced with an equal molar amount of M-556, and e-3 was replaced with an equal molar amount of e-556. The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrum m / z: 882.3080 (theoretical value: 882.3069). Theoretical element content (%): C 65 H 42 N2S: C, 88.40; H, 4.79; N, 3.17. Measured element content (%): C, 88.35; H, 4.82; N, 3.20.

[0439] Synthesis Example 57: Preparation of Compound 566

[0440]

[0441] Compound 566 (17.36 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-566, C-3 was replaced with an equal molar amount of C-566, and M-3 was replaced with an equal molar amount of M-538. HPLC analysis of the solid showed a purity of ≥99.98%. Mass spectrum m / z: 705.2319 (theoretical value: 705.2304). Theoretical element content (%): C 51 H 31NO3: C, 86.79; H, 4.43; N, 1.98. Measured element content (%): C, 86.84; H, 4.39; N, 2.01.

[0442] Synthesis Example 58: Preparation of Compound 571

[0443]

[0444] Following the same preparation method as compound 3 in Example 28, B-3 was replaced with an equal molar amount of B-571 to obtain compound 571 (16.25 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 731.2474 (theoretical value: 731.2460). Theoretical element content (%): C 53 H 33 NO3: C, 86.98; H, 4.55; N, 1.91. Measured element content (%): C, 86.93; H, 4.59; N, 1.88.

[0445] Synthesis Example 59: Preparation of Compound 573

[0446]

[0447] Compound 573 (18.67 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-573 and M-3 was replaced with an equal molar amount of M-573. HPLC analysis of the solid showed a purity of ≥99.97%. Mass spectrum m / z: 787.3072 (theoretical value: 787.3086). Theoretical element content (%): C 57 H 41 NO3: C, 86.89; H, 5.24; N, 1.78. Measured element content (%): C, 86.94; H, 5.20; N, 1.81.

[0448] Synthesis Example 60: Preparation of Compound 586

[0449]

[0450] Compound 586 (17.37 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-571 and M-3 was replaced with an equal molar amount of M-42. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 771.2761 (theoretical value: 771.2773). Theoretical element content (%): C 56 H 37NO3: C, 87.14; H, 4.83; N, 1.81. Measured element content (%): C, 87.09; H, 4.89; N, 1.78.

[0451] Synthesis Example 61: Preparation of Compound 588

[0452]

[0453] Compound 588 (18.77 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-588, C-3 was replaced with an equal molar amount of C-27, and E-3 was replaced with an equal molar amount of E-588. HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum m / z: 781.2630 (theoretical value: 781.2617). Theoretical element content (%): C 57 H 35 NO3: C, 87.56; H, 4.51; N, 1.79. Measured element content (%): C, 87.61; H, 4.47; N, 1.82.

[0454] Synthesis Example 62: Preparation of Compound 604

[0455]

[0456] Compound 604 (18.49 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-604, C-3 was replaced with an equal molar amount of C-77, M-3 was replaced with an equal molar amount of M-604, and E-3 was replaced with an equal molar amount of E-604. HPLC analysis of the solid showed a purity of ≥99.92%. Mass spectrum m / z: 789.1920 (theoretical value: 789.1909). Theoretical element content (%): C 53 H 31 N3OS2: C, 80.58; H, 3.96; N, 5.32. Measured element content (%): C, 80.63; H, 4.00; N, 5.29.

[0457] Synthesis Example 63: Preparation of Compound 647

[0458]

[0459] Following the same preparation method as in Example 28, Compound 3 was synthesized, with B-3 replaced by an equal molar amount of B-647 and e-3 replaced by an equal molar amount of e-647 to obtain Compound 647 (17.81 g). HPLC analysis revealed a solid purity of ≥99.96%. Mass spectrum: m / z: 847.2558 (theoretical value: 847.2545). Theoretical element content (%): C 61 H37 NO2S: C, 86.40; H, 4.40; N, 1.65. Measured element content (%): C, 86.36; H, 4.35; N, 1.68.

[0460] Synthesis Example 64: Preparation of Compound 673

[0461]

[0462] Compound 673 (17.98 g) was obtained by the same preparation method as in Example 28, except that B-3 was replaced with an equal molar amount of B-673, M-3 was replaced with an equal molar amount of M-673, and e-3 was replaced with an equal molar amount of e-77. HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum m / z: 855.2074 (theoretical value: 855.2088). Theoretical element content (%): C 59 H 37 NS3: C, 82.77; H, 4.36; N, 1.64. Measured element content (%): C, 82.82; H, 4.40; N, 1.67.

[0463] Synthesis Example 65: Preparation of Compound 716

[0464]

[0465] Following the same preparation method as in Example 28, Compound 3 was synthesized, with B-3 replaced by an equal molar amount of B-716 and M-3 replaced by an equal molar amount of M-716 to obtain Compound 716 (19.33 g). HPLC analysis revealed a solid purity of ≥99.97%. Mass spectrum: m / z: 858.2716 (theoretical value: 858.2705). Theoretical element content (%): C 62 H 38 N2OS: C, 86.69; H, 4.46; N, 3.26. Measured element content (%): C, 86.74; H, 4.50; N, 3.22.

[0466] [Device Example 1]

[0467] The ITO glass substrate was used as the anode, washed repeatedly in distilled water for 3 times, and ultrasonically washed for 15 minutes. After the distilled water washing was completed, ultrasonic washing was carried out in sequence with isopropyl alcohol, acetone, methanol and other solvents, dried at 120°C, and then sent to the vapor deposition machine.

[0468] Compound HI-1 was evaporated on a prepared ITO transparent electrode on a glass substrate as a hole injection layer with a thickness of 15 nm; compound 3 of the present invention was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 110 nm; main material RH and dopant RD (mass ratio of 92:8) were vacuum evaporated on the hole transport layer as a light-emitting layer with a thickness of 32 nm; compound HB-1 was evaporated on the light-emitting layer as a hole blocking layer with a thickness of 5 nm; compound ET-1 and LiQ (doping ratio of 1:1) were vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 35 nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.2 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm, to prepare an organic electroluminescent device.

[0469]

[0470] [Device Examples 2 to 38]

[0471] Compound 14, compound 16, compound 27, compound 42, compound 44, compound 51, compound 77, compound 101, compound 197, compound 250, compound 350, compound 357, compound 368, compound 371, compound 378, compound 383, compound 388, compound 391, compound 393, compound 397, compound 402, compound 407, compound 417, compound 434, compound 450, compound 521, compound 543, compound 556, compound 566, compound 571, compound 573, compound 586, compound 588, compound 604, compound 647, compound 673, and compound 716 of the present invention were used to replace compound 3 in device example 1 as hole transport layer materials. Except that, an organic electroluminescent device was prepared by the same preparation method as device example 1.

[0472] [Comparative Device Examples 1 to 4]

[0473] Comparative Examples 1 to 4: Preparation of Comparative Organic Electroluminescent Devices 1 to 4

[0474] The compound 3 in the hole transport layer of Example 1 was replaced by comparative compounds 1 to 4 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 to 4.

[0475] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to test the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System.

[0476] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the device examples 1 to 38 of the present invention and comparative examples 1 to 4 are shown in Table 1 below.

[0477] Table 1:

[0478]

[0479]

[0480] The results in Table 1 show that when the triarylamine derivatives based on fluorenyl heterocycles described in the present invention are used as the first hole transport layer of an organic electroluminescent device, they have high hole mobility, high glass transition temperature, and good thermal stability, which can effectively improve the luminous efficiency of the device and increase the life of the organic electroluminescent device. This shows that the triarylamine derivatives based on fluorenyl heterocycles described in the present invention are a class of OLED hole transport layer materials with excellent performance.

[0481] [Device Example 39]

[0482] The ITO glass substrate was used as the anode, washed repeatedly in distilled water for 3 times, and ultrasonically washed for 15 minutes. After the distilled water washing was completed, ultrasonic washing was carried out in sequence with isopropyl alcohol, acetone, methanol and other solvents, dried at 120°C, and then sent to the vapor deposition machine.

[0483] On a glass substrate, HI-2 and HT-1 (doping ratio of 97:3) were evaporated on a prepared ITO transparent electrode as a hole injection layer with a thickness of 13 nm; HT-1 was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 100 nm; the compound 3 of the present invention was vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 115 nm; the main material GH and the dopant GD (mass ratio of 92:8) were vacuum evaporated on the second hole transport layer as a light-emitting layer with a thickness of 35 nm; the compound HB-2 was evaporated on the light-emitting layer as a hole blocking layer with a thickness of 8 nm; the compound ET-2 and LiQ (doping ratio of 1:1) were vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.5 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 120 nm, to prepare an organic electroluminescent device.

[0484]

[0485] [Device Examples 39 to 76]

[0486] Compound 14, compound 16, compound 27, compound 42, compound 44, compound 51, compound 77, compound 101, compound 197, compound 250, compound 350, compound 357, compound 368, compound 371, compound 378, compound 383, compound 388, compound 391, compound 393, compound 397, compound 402, compound 407, compound 417, compound 434, compound 450, compound 521, compound 543, compound 556, compound 566, compound 571, compound 573, compound 586, compound 588, compound 604, compound 647, compound 673, and compound 716 of the present invention were used to replace compound 3 in device example 39 as the second hole transport layer material. Except for this, an organic electroluminescent device was prepared by the same preparation method as device example 39.

[0487] [Comparative Device Examples 5 to 8]

[0488] Comparative Examples 5 to 8: Preparation of Comparative Organic Electroluminescent Devices 5 to 8

[0489] The compound 3 in the second hole transport layer of Example 39 was replaced with comparative compounds 5 to 8 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 5 to 8.

[0490] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to test the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System.

[0491] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the device examples 39 to 76 of the present invention and comparative examples 5 to 8 are shown in Table 2 below.

[0492] Table 2:

[0493]

[0494]

[0495] The results in Table 2 show that when the triarylamine derivatives based on fluorenyl heterocycles described in the present invention are used as the second hole transport layer of an organic electroluminescent device, they have high hole mobility, high glass transition temperature, and good thermal stability, which can effectively improve the luminous efficiency of the device and increase the life of the organic electroluminescent device. This shows that the triarylamine derivatives based on fluorenyl heterocycles described in the present invention are a class of OLED hole transport layer materials with excellent performance.

[0496] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A triarylamine derivative based on a fluorenyl heterocycle, characterized in that: The molecular structure is shown in Formula I: Wherein, the W is selected from O, S or N(R2); R1 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; R2 is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; The k1 is selected from 0, 1, 2, 3 or 4; when k1 is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted benzene ring; The Ar1 is selected from the group shown in Formula 1-a or Formula 1-b, and the * represents a connection site; The R a 、R b Same or different from each other, R a and R b At least one of the groups is selected from the group shown in 1-c, and the rest are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; in formula 1-b, when Ra is not formula 1-c, it is selected from a single bond, substituted or unsubstituted: phenylene, biphenylene, and naphthylene; The R3 are the same or different and are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; The n 2a Selected from 0, 1, 2, 3 or 4; when n 2a When it is greater than 1, two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted benzene ring; The 1-c is selected from one of the following groups: n1 is selected from 0, 1, 2 or 3; n2 is selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4 or 5; n5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; n7 is selected from 0, 1, 2, 3, 4, 5 or 6; Said T is selected from CH; R5 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or a combination thereof; Said L3 is selected from a single bond; The Ar2 is selected from one or a combination of the following groups: The z are identically selected from CH; Said p is selected from O, S or N (R d ); Said q is selected from CH; Said p4 is selected from 0, 1, 2, 3 or 4; The R d Any one selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; The R t One selected from hydrogen, deuterium, tritium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; R6 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted terphenylsilyl, substituted or unsubstituted trinaphthylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, or a combination thereof; The R 6a One or a combination thereof is selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; Said p1 is selected from 0, 1, 2, 3, 4, or 5; said p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said p3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said p4 is selected from 0, 1, 2, 3, or 4; said p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; said p6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; said p7 is selected from 0, 1, or 2; said p8 is selected from 0, 1, 2, or 3; said p9 is selected from 0, 1, 2, 3, 4, 5, or 6; said p 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said p 11 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when two or more R6 are present, the two or more R6 are the same as or different from each other; The L0, L1 and L2 are selected from a single bond or one or a combination of the following groups: R7 is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or a combination thereof; The r1 is selected from 0, 1, 2, 3 or 4; when there are two or more R7, the two or more R7 are the same or different from each other; The term "substituted..." refers to single or multiple substitution by the following groups: deuterium, halogen atoms.

2. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that: The triarylamine derivative based on fluorenyl heterocycle is selected from at least one of Formula I-1 to Formula I-5:

3. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that: The 1-a is selected from one of the following groups:

4. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that The 1-c is selected from one of the following groups:

5. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that: The Ar2 is selected from one or a combination of the following groups:

6. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that: The Ar2 is selected from one or a combination of the following groups:

7. The triarylamine derivative based on fluorenyl heterocycle according to claim 1, characterized in that: The L0, L1 and L2 are selected from a single bond or one or a combination of the following groups: The R7 is selected from one of hydrogen, deuterium, and tritium, or a combination thereof.

8. A fluorenyl heterocyclic triarylamine derivative, characterized in that: The triarylamine derivative based on fluorenyl heterocycle is selected from at least one of the following structures:

9. An organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more of the anode and the cathode, characterized in that: The organic layer comprises a hole transport layer, and the hole transport layer comprises at least one of the fluorenyl heterocycle-based triarylamine derivatives according to any one of claims 1 to 8.

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