Fluorene compound and organic electroluminescent device thereof

Abstract

The invention provides a fluorene compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The fluorene compound shown in the formula 1 has good photoelectric properties, and when the fluorene compound serves as an electron transport material or a hole blocking material to be applied to an organic electroluminescent device, the performance of the device is remarkably improved, and specifically, the performance is low in driving voltage, high in luminous efficiency, long in service life and the like. In addition, the fluorene compound shown in the formula 1 is an n-type charge generation material with good performance, the luminous efficiency of the laminated organic electroluminescent device is effectively improved, and the service life of the laminated organic electroluminescent device is effectively prolonged.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent materials, in particular to a fluorene compound and an organic electroluminescent device thereof. Background Art

[0002] Organic electroluminescent devices (OLEDs), as a new generation of display technology, offer many superior properties compared to traditional display technologies, such as self-luminescence, wide viewing angles, fast response times, ultra-thinness, ultra-lightness, high contrast, high brightness, and flexible displays. In recent years, as OLED technology continues to mature, its application scope has continued to expand, and it is currently primarily used in smart watches, smartphones, laptops, tablets, TVs, smart wearable devices, virtual reality (VR), and automotive displays.

[0003] OLEDs often use a sandwich structure, where the organic functional layers are sandwiched between the anode and cathode on either side of the device. The organic functional layers primarily include: hole injection layer (HIL), hole transport layer (HTL), light-emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL), etc. In addition, a capping layer (CPL) is introduced outside the device's electrodes, and a charge generation layer (CGL) exists between the two light-emitting units. Under the action of an external electric field, holes and electrons are injected from the anode and cathode, respectively, and transported through the hole transport layer and electron transport layer, respectively, to the light-emitting layer. There, they combine to form excitons, which then emit light through radiative decay.

[0004] In recent years, after continuous development, although a large number of OLED materials have been researched and developed, at the same time, there are also higher requirements for the performance of OLED devices. Therefore, it is necessary to continuously research and develop organic electroluminescent materials with better performance to meet the requirements of the industry. Summary of the Invention

[0005] In view of the problems existing in the prior art, the present invention provides a fluorene compound and an organic electroluminescent device thereof.

[0006] The present invention provides a fluorene compound represented by the following formula 1:

[0007]

[0008] Wherein, the X is the same or different and is selected from C(R x ) or N, and at least one is selected from N; said R xthe same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0009] The Ar is selected from one of the groups shown below,

[0010]

[0011] The a1 is selected from an integer of 0 to 4, the a2 is selected from an integer of 0 to 5, and the f0 is selected from an integer of 0 to 2;

[0012] The R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0013] The R 1a the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0014] The E's are the same or different and are selected from C(R e ) or N,

[0015] The F are the same or different and are selected from C(R e ) or N, and at least one F is selected from N,

[0016] The R e The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R e bonded to each other to form a substituted or unsubstituted ring;

[0017] The ring A is selected from a substituted or unsubstituted C3-C30 alicyclic ring;

[0018] Said X1 is selected from O, S or N(R x1 ), wherein X2 is selected from O, S or N(R x2 ), wherein Y1 is selected from CH or N; wherein R x1 、R x2 independently selected from one of hydrogen, deuterium, tritium, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0019] The Y is the same or different and is selected from C(R y ) or N; said R y The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R y bonded to each other to form a substituted or unsubstituted ring;

[0020] The Z are the same or different and are selected from C(R z ) or N; said R z The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R z bonded to each other to form a substituted or unsubstituted ring;

[0021] The R0 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0022] Ar0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0023] The L0 and L1 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof;

[0024] The L2 is selected from a single bond, one of the following groups or a combination thereof,

[0025]

[0026] The W are the same or different and are selected from C(R w ) or N; said R w The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R w bonded to each other to form a substituted or unsubstituted ring;

[0027] The X0 is selected from O, S or N (R x0 ), the R x0 One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0028] The b is selected from integers of 0-3.

[0029] The present invention also provides an organic electroluminescent device, which contains the fluorene compound of the present invention.

[0030] Beneficial Effects: The fluorene compound of Formula 1 of the present invention exhibits excellent optoelectronic properties. Its use as an electron transport material or hole-blocking material in organic electroluminescent devices significantly improves device performance, specifically demonstrating lower driving voltage, higher luminous efficiency, and longer service life. Furthermore, the fluorene compound of Formula 1 of the present invention is also a highly effective n-type charge-generating material, effectively improving the luminous efficiency and service life of stacked organic electroluminescent devices. DETAILED DESCRIPTION

[0031] The present invention is further illustrated below with reference to specific examples. It should be understood that these examples are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, modifications of various equivalent forms of the present invention made by those skilled in the art all fall within the scope of protection claimed in this application.

[0032] In the compounds herein, any atom not designated as a specific isotope encompasses any stable isotope of that atom, including atoms at both their natural and unnatural isotopic abundances. As used herein, "H," "hydrogen," and "hydrogen atom" refer to isotopes having different numbers of neutrons, including protium, deuterium, and tritium.

[0033] In this specification, the halogen includes fluorine, chlorine, bromine and iodine.

[0034] In the present specification, when the position of a substituent on a ring is not fixed, it means that the substituent can be attached to any of the corresponding optional positions of the ring.

[0035] For example, Can represent Can represent Can represent And so on.

[0036] In this specification, "two adjacent groups are bonded to form a ring" means that the adjacent groups are bonded to 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 the combination of adjacent groups can be connected to another ring to form a spiro structure. The following examples are shown:

[0037]

[0038] 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.

[0039] In this specification, the term "an integer selected from 0 to M" refers to any integer selected from 0 to M, including 0, 1, 2, ... M-2, M-1, and M. For example, the term "b is an integer selected from 0 to 3" means that b is selected from 0, 1, 2, or 3. And so on.

[0040] In this specification, the term "unsubstituted ZZ group" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms of the ZZ group are not replaced by substituents. For example, the term "unsubstituted aryl group" in the context of a "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atoms of the aryl group are not replaced by substituents. The same applies by analogy.

[0041] In this specification, "CXX-CYY" in a "substituted or unsubstituted ZZ group of CXX-CYY" represents the number of carbon atoms in the unsubstituted "ZZ group." If the "ZZ group" has a substituent, the number of carbon atoms in the substituent is not included. For example, "C6-C60" in a "substituted or unsubstituted C6-C60 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group." If the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. The same applies analogously.

[0042] In this specification, the "substituted" in the "substituted or unsubstituted" refers to the replacement of at least one hydrogen atom on the group by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen replaced by the substituent may be any position. The substituents represented by the "substituted" in the "substituted or unsubstituted" include the following groups: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted C3-C15 heterocyclic group, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, etc. Preferred are the following groups: deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, isobornyl, fenchyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, benzothiophene, dibenzothiophene, benzodibenzothiophene, indolyl, carbazolyl, benzocarbazolyl, spirofluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, etc. In addition, each of the above substituents may be substituted or unsubstituted, and two adjacent substituents may be bonded to form a ring.

[0043] In this specification, the alkyl group refers to a hydrocarbon group formed by missing one hydrogen atom from an alkane molecule, and the alkyl group includes straight-chain alkyl groups and branched-chain alkyl groups. Examples of the alkyl group may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc., but are not limited thereto. A chain alkyl group containing three or more carbon atoms includes its isomers, such as a propyl group includes n-propyl and isopropyl, a butyl group includes n-butyl, sec-butyl, isobutyl and tert-butyl, and so on. The number of carbon atoms in the alkyl group is 1 to 30, preferably 1 to 20, preferably 1 to 15, and more preferably 1 to 10.

[0044] In this specification, a cycloalkyl group refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. Such cycloalkyl groups include monocyclic cycloalkyl groups, polycyclic cycloalkyl groups, and bridged cycloalkyl groups. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, and bornyl groups. The cycloalkyl group has 3 to 30 carbon atoms, preferably 3 to 20, more preferably 3 to 15, and more preferably 3 to 10.

[0045] In this specification, the "silyl group" refers to -Si(R t )3 groups, wherein each R t The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, etc. Preferably, each R tthe same or different selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, 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 cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornene The alkyl radical may include, but is not limited to, a substituted or unsubstituted phenyl radical, a substituted or unsubstituted biphenyl radical, a substituted or unsubstituted naphthyl radical, a substituted or unsubstituted dihydroindenyl radical, a substituted or unsubstituted indenyl radical, a substituted or unsubstituted tetrahydronaphthyl radical, a substituted or unsubstituted dihydronaphthyl radical, a substituted or unsubstituted benzocyclobutane radical, a substituted or unsubstituted benzocyclobutenyl radical, a substituted or unsubstituted benzocyclopropane radical, a substituted or unsubstituted pyridyl radical, a substituted or unsubstituted pyrimidinyl radical, a substituted or unsubstituted pyrazinyl radical, a substituted or unsubstituted pyridazinyl radical, etc. Examples thereof include, but are not limited to, trimethylsilyl radical, triethylsilyl radical, triisopropylsilyl radical, tri-tert-butylsilyl radical, dimethylethylsilyl radical, dimethylisopropylsilyl radical, dimethyltert-butylsilyl radical, tricyclopentanylsilyl radical, tricyclohexylsilyl radical, triphenylsilyl radical, tribiphenylsilyl radical, tripyridylsilyl radical, etc.

[0046] In this specification, the aryl group refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, or a combination thereof. Examples of the aryl group include phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, pyrenyl, perylene, The aryl group may include, but is not limited to, fluoranyl, benzofluorenyl, spiroanthracenefluorenyl, etc. The number of carbon atoms in the aryl group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0047] In this specification, the fused polycyclic group refers to a monovalent group comprising at least two rings, in which at least one aromatic ring and at least one non-aromatic ring are fused to each other. Examples of the fused polycyclic group may include benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the fused polycyclic group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0048] In this specification, the heteroaryl group refers to a general term for a group in which one or more carbon atoms in an aryl group are replaced by a heteroatom, and the heteroatom includes, but is not limited to, atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, and silicon. The heteroaryl group includes a monocyclic heteroaryl group, a fused ring heteroaryl group, or a combination thereof. Examples of the heteroaryl group may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, carbazolyl, benzocarbazolyl, spirofluorenylxanthenyl, spirofluorenylthioanthenyl, spirofluorenylazaanthenyl, etc. The heteroaryl group may have 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 25 carbon atoms, and even more preferably 2 to 18 carbon atoms.

[0049] In this specification, the arylene group refers to the general term for a divalent group left after removing two hydrogen atoms from the aromatic carbon nucleus of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group, or a combination thereof. Examples of the arylene group may include phenylene, biphenylene, terphenylene, quaterphenylene, pentphenylene, naphthylene, phenanthrenyl, anthracene, triphenylene, pyrenyl, fluoranthenyl, perylene, phenanthrenyl ... The arylene group may include, but is not limited to, benzofluorenyl, fluorenyl, benzofluorenyl, spiroanthracenefluorenyl, etc. The number of carbon atoms in the arylene group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 10.

[0050] In this specification, the sub-fused polycyclic group refers to a divalent group including at least two rings, in which at least one aromatic ring and at least one non-aromatic ring are fused to each other. Examples of the fused polycyclic group may include benzocyclopropanediyl, benzocyclobutanediyl, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the fused polycyclic group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0051] In this specification, the heteroarylene group refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc., but is not limited thereto. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a condensed-ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group include pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, benzothiophenylene, dibenzothiophenylene, benzodibenzothiophenylene, indolylene, carbazolylene, benzocarbazolylene, etc., but are not limited thereto. The number of carbon atoms in the heteroarylene group is 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 2 to 18.

[0052] The present invention provides a fluorene compound represented by the following formula 1:

[0053]

[0054] Wherein, the X is the same or different and is selected from C(R x ) or N, and at least one is selected from N; said R x the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0055] The Ar is selected from one of the groups shown below,

[0056]

[0057] The a1 is selected from an integer of 0 to 4, the a2 is selected from an integer of 0 to 5, and the f0 is selected from an integer of 0 to 2;

[0058] The R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0059] The R 1athe same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0060] The E's are the same or different and are selected from C(R e ) or N,

[0061] The F are the same or different and are selected from C(R e ) or N, and at least one F is selected from N,

[0062] The R e The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R e bonded to each other to form a substituted or unsubstituted ring;

[0063] The ring A is selected from a substituted or unsubstituted C3-C30 alicyclic ring;

[0064] Said X1 is selected from O, S or N(R x1 ), wherein X2 is selected from O, S or N(R x2 ), wherein Y1 is selected from CH or N; wherein R x1 、R x2 independently selected from one of hydrogen, deuterium, tritium, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0065] The Y is the same or different and is selected from C(R y ) or N; said R y The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R y bonded to each other to form a substituted or unsubstituted ring;

[0066] The Z are the same or different and are selected from C(R z ) or N; said R z The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R z bonded to each other to form a substituted or unsubstituted ring;

[0067] The R0 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

[0068] Ar0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0069] The L0 and L1 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof;

[0070] The L2 is selected from a single bond, one of the following groups or a combination thereof,

[0071]

[0072] The W are the same or different and are selected from C(R w ) or N; said R w The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R w bonded to each other to form a substituted or unsubstituted ring;

[0073] The X0 is selected from O, S or N (R x0 ), the R x0 One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0074] The b is selected from integers of 0-3.

[0075] Preferably, the Ar is selected from one of the groups shown below,

[0076]

[0077]

[0078] a1 is selected from integers of 0 to 4, a2 is selected from integers of 0 to 5, a3 is selected from integers of 0 to 3, a4 is selected from integers of 0 to 7, a5 is selected from integers of 0 to 9, a6 is selected from integers of 0 to 6, a7 is selected from integers of 0 to 2, a8 is selected from integers of 0 to 8, a9 is selected from integers of 0 to 10, and f0 is selected from integers of 0 to 2;

[0079] The R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl;

[0080] The R 1a the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0081] The R e The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Re bonded to each other to form a substituted or unsubstituted ring;

[0082] The R e1 The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R e1 bonded to each other to form a substituted or unsubstituted ring;

[0083] Said X1 is selected from O, S or N(R x1 ), wherein X2 is selected from O, S or N(R x2 ); the R x1 、R x2 independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl.

[0084] Preferably, the One selected from the following groups,

[0085]

[0086] The b1 is selected from an integer of 0 to 4, the b2 is selected from an integer of 0 to 6, and the b3 is selected from an integer of 0 to 3;

[0087] The R z the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R z bonded to each other to form a substituted or unsubstituted ring;

[0088] Ar0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0089] The L0 is selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 condensed polycyclic group, and a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof.

[0090] Preferably, the wherein R0 is the same or different and is selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl ... substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted spirofluorenoxanthenyl , substituted or unsubstituted spirofluorenthioanthracenyl, substituted or unsubstituted spirofluorenazanthracenyl, substituted or unsubstituted spiroanthracenyl, 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 quinazoline, substituted or unsubstituted quinoxalinyl.

[0091] Preferably, the One selected from the following groups,

[0092]

[0093]

[0094] The c1 is selected from an integer of 0 to 5, and the c2 is selected from an integer of 0 to 4;

[0095] The R2 are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2 are bonded to each other to form a substituted or unsubstituted ring;

[0096] Said X3 is selected from O, S, N (R x3 ) or C(R x3 )2, the R x3 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x3 They are bonded to each other to form a substituted or unsubstituted ring.

[0097] Preferably, L0 and L1 are independently selected from a single bond, one of the following groups, or a combination thereof:

[0098]

[0099] The Q is the same or different and is selected from C(R q ) or N;

[0100] The R q the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R q bonded to each other to form a substituted or unsubstituted ring;

[0101] The X4 is selected from C(R x4 )2、O、S or N(R x4 ), the R x4 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rx4 bonded to each other to form a substituted or unsubstituted ring;

[0102] The L 01 , L 02 independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzocyclobutene group, a substituted or unsubstituted benzocyclobutenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted dihydroindenylene group, a substituted or unsubstituted dihydronaphthylene group, a substituted or unsubstituted tetrahydronaphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, and a substituted or unsubstituted pyridazinylene group;

[0103] The a is selected from integers of 0-4.

[0104] Preferably, L0 and L1 are independently selected from a single bond, one of the following groups, or a combination thereof:

[0105]

[0106] The d is selected from an integer of 0 to 4, the d1 is selected from an integer of 0 to 3, and the d2 is selected from an integer of 0 to 2;

[0107] The R q the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R q bonded to each other to form a substituted or unsubstituted ring;

[0108] The R x4 The same or different R is selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x4 bonded to each other to form a substituted or unsubstituted ring;

[0109] The L 01 , L 02independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzocyclobutanediyl group, a substituted or unsubstituted benzocyclobutenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted dihydroindenylene group, a substituted or unsubstituted dihydronaphthylene group, a substituted or unsubstituted tetrahydronaphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, and a substituted or unsubstituted pyridazinylene group.

[0110] Preferably, L2 is selected from a single bond, one of the following groups, or a combination thereof:

[0111]

[0112] The e is selected from an integer of 0 to 4, the e1 is selected from an integer of 0 to 3, and the e2 is selected from an integer of 0 to 2;

[0113] The R w The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R w bonded to each other to form a substituted or unsubstituted ring;

[0114] The R x0 One selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl.

[0115] Preferably, the fluorene compound is selected from at least one of the structures shown below:

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] The above lists some specific chemical structures of the fluorene compounds of Formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. All groups based on the structure shown in Formula 1 and having substituents as defined above should be included.

[0165] The present invention also provides an organic electroluminescent device, which contains the fluorene compound described in the present invention.

[0166] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer located between the anode and the cathode, and the organic layer contains the fluorene compound of the present invention.

[0167] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprises an electron transport region, and the electron transport region contains the fluorene compound of the present invention.

[0168] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes at least one of an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer contains the above-mentioned fluorene compound of the present invention.

[0169] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes an electron transport layer, and the electron transport layer contains the fluorene compound of the present invention.

[0170] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes an electron transport region, the electron transport region includes a hole blocking layer, and the hole blocking layer contains the fluorene compound of the present invention.

[0171] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer contains the fluorene compound of the present invention.

[0172] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a light-emitting layer, the light-emitting layer contains a host material and a doping material, and the host material contains the fluorene compound of the present invention.

[0173] Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer located between the anode and the cathode, the organic layer comprises a charge generation layer, and the charge generation layer contains the fluorene compound of the present invention.

[0174] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a charge generation layer, the charge generation layer includes an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer contains the above-mentioned fluorene compound of the present invention.

[0175] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a first light-emitting unit, a second light-emitting unit, and a charge generation layer, the charge generation layer is located between the first light-emitting unit and the second light-emitting unit, the charge generation layer includes an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer contains the above-mentioned fluorene compound of the present invention.

[0176] Preferably, the organic electroluminescent device comprises an anode, a cathode and a covering layer, wherein the covering layer is located on the side of the cathode facing away from the anode, and the covering layer contains the fluorene compound of the present invention.

[0177] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a hole transport region, and the hole transport region comprises a star-shaped compound of formula 2.

[0178]

[0179] The Ar 21 ~Ar 26 One independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 fused polycyclic group, or a substituted or unsubstituted C2-C60 heteroaryl group;

[0180] The L 21 ~L 26 independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof;

[0181] The L 11 ~L 13 independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof;

[0182] The f is selected from an integer of 0 to 3;

[0183] The R 01 The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R 01 They are bonded to each other to form a substituted or unsubstituted ring.

[0184] Preferably, the star-shaped compound of formula 2 is selected from at least one of the structures shown below:

[0185]

[0186] Preferably, the Ar 21 ~Ar 26Independently selected from one of the groups shown below,

[0187]

[0188] The g1 is selected from an integer of 0 to 5, the g2 is selected from an integer of 0 to 4, and the f1 is selected from an integer of 0 to 2;

[0189] The V's are the same or different and are selected from CH or N;

[0190] The R 02 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R 02 bonded to each other to form a substituted or unsubstituted ring;

[0191] The X5 is selected from C(R x5 )2、O、S or N(R x5 ), wherein X6 is selected from O, S or N(R x6 ), the R x5 、R x6 independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R x5 bonded to each other to form a substituted or unsubstituted ring;

[0192] The R 1b The same or different ones are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl.

[0193] Preferably, the Ar 21 ~Ar 26 Independently selected from one of the groups shown below,

[0194]

[0195]

[0196]

[0197] The g1 is selected from an integer of 0 to 5, the g2 is selected from an integer of 0 to 4, the g3 is selected from an integer of 0 to 3, the g4 is selected from an integer of 0 to 7, the g5 is selected from an integer of 0 to 9, the g6 is selected from an integer of 0 to 6, the g7 is selected from an integer of 0 to 2, the g8 is selected from an integer of 0 to 8, the g9 is selected from an integer of 0 to 10, and the g 10 An integer selected from 0 to 12, wherein g 11 An integer selected from 0 to 14, wherein f1 is an integer selected from 0 to 2;

[0198] The R 02 the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0199] The R x5 、R x6 independently selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl;

[0200] The R g the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0201] The R 1b The same or different ones are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl.

[0202] Preferably, the L 21 ~L 26Independently selected from a single bond, one of the following groups or a combination thereof,

[0203]

[0204] The R 03 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R 03 bonded to each other to form a substituted or unsubstituted ring;

[0205] Said X7 is selected from C(R x7 )2、O、S or N(R x7 ), the R x7 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x7 bonded to each other to form a substituted or unsubstituted ring;

[0206] The h1 is selected from integers of 0 to 4; and the g is selected from integers of 0 to 3.

[0207] Preferably, the L 21 ~L 26 Independently selected from a single bond, one of the following groups or a combination thereof,

[0208]

[0209] The h1 is selected from an integer of 0 to 4, the h2 is selected from an integer of 0 to 3, the h3 is selected from an integer of 0 to 2, the h4 is selected from an integer of 0 to 6, and the h5 is selected from an integer of 0 to 8;

[0210] The R 03 the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0211] The R x7the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x7 bonded to each other to form a substituted or unsubstituted ring;

[0212] The R h The same or different ones are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl.

[0213] Preferably, the L 11 ~L 13 independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted benzofluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzodibenzofuranyl group, a substituted or unsubstituted benzothiazolin ... The present invention is a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted benzodibenzothiophenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted benzocarbazolylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted dihydroindenylene group, a substituted or unsubstituted dihydronaphthylene group, a substituted or unsubstituted tetrahydronaphthylene group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutenylene group, and a substituted or unsubstituted benzocycloheptanylene group.

[0214] Preferably, the R 01the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, 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 cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted The present invention further comprises one of naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, and substituted or unsubstituted benzocycloheptyl.

[0215] Preferably, the star-shaped compound is selected from at least one of the structures shown below:

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] The above lists some specific chemical structures of the star-shaped compounds of Formula 2 of the present invention, but the present invention is not limited to these listed chemical structures. All chemical structures based on the structure shown in Formula 2 and with substituents as defined above should be included.

[0237] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region contains the above-mentioned fluorene compound of the present invention, and the hole transport region contains the above-mentioned star-shaped compound of the present invention.

[0238] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region includes at least one of a hole blocking layer and an electron transport layer, the hole blocking layer is located between the light-emitting layer and the electron transport layer, at least one of the hole blocking layer and the electron transport layer contains the above-mentioned fluorene compound of the present invention, and the hole transport region contains the above-mentioned star-shaped compound of the present invention.

[0239] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region includes a hole blocking layer, the hole blocking layer contains the above-mentioned fluorene compound of the present invention, and the hole transport region contains the above-mentioned star-shaped compound of the present invention.

[0240] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region includes an electron transport layer, the electron transport layer contains the above-mentioned fluorene compound of the present invention, and the hole transport region contains the above-mentioned star-shaped compound of the present invention.

[0241] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region contains the above-mentioned fluorene compound of the present invention, the hole transport region includes at least one of a hole transport layer and a light-emitting auxiliary layer, the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer, and at least one of the hole transport layer and the light-emitting auxiliary layer contains the above-mentioned star-shaped compound of the present invention.

[0242] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region contains the above-mentioned fluorene compound of the present invention, the hole transport region includes a hole transport layer, and the hole transport layer contains the above-mentioned star-shaped compound of the present invention.

[0243] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the electron transport region contains the above-mentioned fluorene compound of the present invention, the hole transport region includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer contains the above-mentioned star-shaped compound of the present invention.

[0244] Preferably, the thickness of the hole blocking layer, electron transport layer, hole transport layer and luminescence auxiliary layer may be 1 nm to 1 μm, preferably 1 nm to 800 nm, more preferably 5 nm to 500 nm, and most preferably 10 nm to 100 nm.

[0245] The functional layers of the organic electroluminescent device of the present invention may further comprise at least one of the following functional layers: a hole injection layer, a hole transport layer, a luminescence-assisting layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer, a charge generation layer, a capping layer, etc., but are not limited thereto. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, luminescent properties, charge generation properties, or light extraction properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film layer may be composed of only one material or multiple materials.

[0246] The present invention does not particularly limit the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The following is an introduction to the organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:

[0247] In the specification, the anode needs to have a material with a higher work function in order to inject holes into the organic layer. The anode includes but is not limited to the materials described below, metals or their alloys, metal oxides, laminated materials, etc. Specific examples may include silver (Ag), platinum (Pt), aluminum (Al), nickel (Ni), copper (Cu), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), indium tin oxide (ITO), etc., but are not limited thereto. The film thickness of the anode is 1 nm to 1 μm, preferably 10 nm to 500 nm, and more preferably 50 nm to 200 nm.

[0248] In this specification, the cathode needs to have a low work function to inject electrons into the organic layer. The cathode includes, but is not limited to, the materials described below, metals or their alloys, laminated materials, etc. Specific examples include, but are not limited to, magnesium (Mg), silver (Ag), magnesium:silver (Mg:Ag), magnesium:ytterbium (Mg:Yb), aluminum (Al), gold (Au), etc. The cathode film thickness is 1nm to 500nm, preferably 1nm to 200nm, and more preferably 5nm to 50nm.

[0249] In this specification, the hole injection layer has the function of reducing the interface barrier between the anode and the hole transport layer and improving the hole injection capability. The hole injection material includes, but is not limited to, the following materials: metal oxides, phthalocyanine compounds, aromatic amine compounds, low molecular weight organic compounds such as conjugated organic materials containing polycyano groups, polymer materials, and the like. Specific examples include, but are not limited to, silver oxide (AgO), copper phthalocyanine (CuPc), 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triyldiazonitrile (cyanodimethylphthalimide))tris(2,3,5,6-tetrafluorobenzonitrile), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), and the like. The hole injection layer has a thickness of 0.1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 1 nm to 500 nm.

[0250] In this specification, the hole transport layer has the function of improving the transport efficiency of holes in the device and blocking electrons in the light-emitting layer. The hole transport layer includes but is not limited to the following materials, aromatic amine derivatives, carbazole derivatives, polymers, etc. Specific examples may include N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N-([1, 1'-biphenyl]-4-yl)-9, 9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, 9, 9'-(1, 3-phenyl)di-9H-carbazole (MCP), 4, 4'-cyclohexylbis[N, N-bis(4-methylphenyl)aniline] (TAPC), N, N'-diphenyl-N, N'-bis(3 -methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetrakis(diphenylamino)-9,9-spirobifluorene (Spiro-TAD), 1,3,5-tri(9-carbazolyl)benzene (TCB), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), poly(4-vinyltriphenylamine) (PVTPA), etc., but not limited thereto. The hole transport layer has a thickness of 1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 5 nm to 500 nm.

[0251] In this specification, the light-emitting layer may contain one or more materials, and may include a host material and a dopant material. The doping ratio of the host material to the dopant material may vary depending on the materials used. Typically, the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%. The light-emitting layer has a thickness of 1 nm to 500 nm, preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.

[0252] The main material of the light-emitting layer can be one material or two or more materials. The main material includes but is not limited to the following materials, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 9-(4-(dibenzo[b,d]furan-1-yl)phenyl)-7-phenyl-7,9-dihydrobenzo[g]indole[2,3-b]carbazole, 9-(3-(dibenzo[b,d]furan-2-yl)phenyl)-7-phenyl-7,9-dihydro Benzo[g]indole[2,3-b]carbazole, 9,9'-bis([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole, 2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(4-(triphenyl-2-yl)phenyl)-1,3,5-triazine, 2,4-diphenyl-6-(3-(triphenyl-2-yl)phenyl)-1,3,5-triazine, 2-([1,1'-biphenyl] -3-yl)-4,6-bis(dibenzo[b,d]furan-2-yl)-1,3,5-triazine, 9-(naphthalene-1-yl)-10-(4-(naphthalene-2-yl)phenyl)anthracene, 4,4-bis(9-carbazole)biphenyl (CBP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), 2,7-bis(carbazol-9-yl)-9,9-spirobifluorene (Spiro-2CBP), 3,3'- Bis(dibenzothiophen-4-yl)-1,1'-biphenyl (m-BPDBT), 9,10-di-2-naphthoanthracene (AND), 9,10-di(naphthalene-1-yl)anthracene, 1,4-bis(9-phenyl-9H-fluoren-9-yl)benzene (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9Hcarbazole (CzSi), etc., but are not limited thereto.

[0253] The doping material may be a fluorescent material, a phosphorescent material, a TADF material or a combination thereof, and the doping material includes but is not limited to the following materials: metal complexes, aromatic amine derivatives, styrylamine compounds, condensed aromatic compounds, heterocyclic compounds, etc. Specific examples of doping materials may include bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (FIrPic), bis(2-phenylpyridinium)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridinium)iridium (Ir(ppy)3), bis(1-phenyl-isoquinolinato)(acetylacetonato)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinolinato)iridium (Ir(piq)3), bis[9,9-dimethyl-2-(2-quinolinyl)-9H-fluoren-3-yl](2,4-pentanedione)iridium (Ir(flq)2(acac)), N 1 ,N 6 -bis(dibenzo[b,d]furan-4-yl)-N 1 ,N 6 -diphenylpyrene-1,6-diamine, 2,5,8,11-tetra-tert-butylperylene (TBPe), 1,4-bis(4-(9H-carbazol-9-yl)phenyl)benzene (BCzSB), 4,4'-bis[4-(di-p-tolylamino)phenyl]biphenyl (DPAVBi), coumarin 545T, 4-(dicyanomethylidene)-2-methyl-6-(4-dimethylaminophenyl)-4H-pyran (DCM), etc., but are not limited thereto.

[0254] In this specification, the hole blocking layer has the function of blocking holes in the light-emitting layer and increasing the binding rate of electrons and holes. The hole blocking layer material may include imidazole derivatives, phenanthroline derivatives, triazole derivatives, rare earth complexes, oxazole derivatives, triazine derivatives, etc., such as 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(8-hydroxy-2-methylquinolinol)-(4-phenylphenoxy)aluminum (BAlq), etc., but is not limited thereto. The hole blocking layer has a thickness of 0.01 nm to 500 nm, preferably 0.1 nm to 200 nm, and more preferably 0.1 nm to 100 nm.

[0255] In this specification, the electron transport layer has the function of improving the transmission efficiency of electrons in the device and blocking holes in the light-emitting layer. The electron transport layer includes but is not limited to the following materials, metal complexes, heteroaromatic compounds, etc. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3, 5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 8-(4-(4,6-di(naphthalene-2-yl)-1,3,5-triazine-2-yl)phenyl)quinoline, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, etc., but not limited thereto. The electron transport layer has a thickness of 1 nm to 1 μm, preferably 1 nm to 800 nm, and more preferably 5 nm to 500 nm.

[0256] In this specification, the electron injection layer has the function of reducing the interface barrier between the cathode and the electron transport and improving the electron injection ability. The electron injection layer material includes but is not limited to the following materials, metals, metal compounds, metal oxides, etc. Specific examples may include lithium (Li), lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), lithium oxide (Li2O), cesium carbonate (Cs2CO3), etc., but are not limited thereto. The electron injection layer film thickness is 0.01nm to 200nm, preferably 0.1nm to 100nm, and more preferably 0.1nm to 50nm.

[0257] In this specification, the cover layer has the function of coupling out light trapped within the device. Materials for the cover layer include, but are not limited to, the following materials: metal compounds, aromatic amine derivatives, carbazole derivatives, and the like. Specific examples include tris(8-hydroxyquinolinolato)aluminum(III) (Alq3), N,N'-di(naphthalene-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), and 4,4'-bis(9-carbazole)biphenyl (CBP).

[0258] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0259] The organic electroluminescent device of the present invention is mainly used in the fields of information display technology and lighting, and is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smart watches, VR, car systems, digital cameras, wearable devices, etc.

[0260] Synthesis Example

[0261] Raw materials and reagents: The present invention has no particular limitations on the raw materials or reagents used in the following synthetic examples. They can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent grade.

[0262] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0263] There are no particular limitations on the preparation method of the fluorene compound of Formula 1 of the present invention, and conventional methods known to those skilled in the art may be employed. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The fluorene compound of Formula 1 of the present invention may be prepared, for example, using the synthetic route shown below.

[0264]

[0265] There are no particular limitations on the preparation method of the star-shaped compound of Formula 2 of the present invention, and conventional methods known to those skilled in the art may be employed. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The star-shaped compound of Formula 2 of the present invention can be prepared, for example, using the synthetic route shown below.

[0266]

[0267] Said Xn is a halogen, for example, Xn are the same or different and are selected from Cl, Br, and I.

[0268] Synthesis Example 1:

[0269]

[0270] Under nitrogen protection, a-2 (16.60 g, 90.00 mmol), b-2 (15.48 g, 90.00 mmol), K2CO3 (18.66 g, 135.00 mmol), Pd(PPh3)4 (1.04 g, 0.9 mmol), and 700 mL of toluene / ethanol / water (2:1:1) were added to the reaction flask, and the reaction was stirred at 60°C for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, a small amount of distilled water was added, the organic phase was separated, and the mixture was filtered through silica gel. The solvent was evaporated under reduced pressure, and the crude product obtained after filtration was recrystallized with ethyl acetate to obtain intermediate A-2 (15.66 g, yield 63%); HPLC purity ≧99.80%.

[0271] Under nitrogen protection, A-2 (13.81 g, 50.00 mmol), c-2 (18.11 g, 50.00 mmol), Na2CO3 (10.60 g, 100.00 mmol), Pd(PPh3)4 (578 mg, 0.50 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to the reaction flask, and the reaction was stirred at 60°C for 9 hours. After the reaction was completed, it was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized from toluene to obtain intermediate B-2 (18.97 g, yield 68%); HPLC purity ≧99.87%.

[0272] Under nitrogen, a reaction flask was added with B-2 (11.16 g, 20.00 mmol), d-2 (3.88 g, 20.00 mmol), K2CO3 (5.53 g, 40.00 mmol), Pd(dppf)Cl2 (146 mg, 0.20 mmol), and 400 mL of toluene / ethanol / water (2:1:1). The mixture was stirred and reacted under reflux for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain compound 2 (9.94 g, 74% yield); HPLC purity ≥99.96%. Mass spectrum m / z: 671.2749 (theoretical value: 671.2757). Theoretical element content (%): C 47 H 37 N3Si: C, 84.02; H, 5.55; N, 6.25. Measured element content (%): C, 84.05; H, 5.56; N, 6.23.

[0273] Synthesis Example 2:

[0274]

[0275] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-22, and the other steps were the same to obtain compound 22 (11.87 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 823.3392 (theoretical value: 823.3383). Theoretical element content (%) C 59 H 45 N3Si: C, 85.99; H, 5.50; N, 5.10. Measured element content (%): C, 85.95; H, 5.53; N, 5.12.

[0276] Synthesis Example 3:

[0277]

[0278]

[0279] Following the preparation method of Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-38 and c-38, respectively, and the other steps were the same to obtain compound 38 (11.17 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 797.3218 (theoretical value: 797.3226). Theoretical element content (%) C 57 H 43 N3Si: C, 85.78; H, 5.43; N, 5.27. Measured element content (%): C, 85.77; H, 5.44; N, 5.25.

[0280] Synthesis Example 4:

[0281]

[0282] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-69, and the other steps were the same to obtain compound 69 (10.83 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 721.2921 (theoretical value: 721.2913). Theoretical element content (%) C 51 H 39 N3Si: C, 84.84; H, 5.45; N, 5.82. Measured element content (%): C, 84.81; H, 5.42; N, 5.85.

[0283] Synthesis Example 5:

[0284]

[0285] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-74 and d-74, respectively, and the other steps were the same to obtain compound 74 (12.13 g) with HPLC purity ≥99.97%. Mass spectrum m / z: 797.3235 (theoretical value: 797.3226). Theoretical element content (%) C 57 H 43 N3Si: C, 85.78; H, 5.43; N, 5.27. Measured element content (%): C, 85.74; H, 5.42; N, 5.29.

[0286] Synthesis Example 6:

[0287]

[0288] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-88 and d-88, respectively, and the other steps were the same to obtain compound 88 (12.21 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 847.3375 (theoretical value: 847.3383). Theoretical element content (%) C 61 H 45 N3Si: C, 86.39; H, 5.35; N, 4.95. Measured element content (%): C, 86.37; H, 5.31; N, 4.97.

[0289] Synthesis Example 7:

[0290]

[0291] Following the preparation method of Synthesis Example 1, a-2 and b-2 were replaced with equimolar amounts of a-90 and b-90, respectively, and the other steps were the same to obtain compound 90 (11.64 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 796.3281 (theoretical value: 796.3274). Theoretical element content (%) C 58 H 44 N2Si: C, 87.40; H, 5.56; N, 3.51. Measured element content (%): C, 87.42; H, 5.53; N, 3.53.

[0292] Synthesis Example 8:

[0293]

[0294] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-97, and the other steps were the same to obtain compound 97 (11.43 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 771.3079 (theoretical value: 771.3070). Theoretical element content (%) C 55 H 41 N3Si: C, 85.57; H, 5.35; N, 5.44. Measured element content (%): C, 85.52; H, 5.36; N, 5.41.

[0295] Synthesis Example 9:

[0296]

[0297] Following the preparation method of Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-97 and c-106, respectively, and the other steps were the same to obtain compound 106 (11.51 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 821.3216 (theoretical value: 821.3226). Theoretical element content (%) C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured element content (%): C, 86.23; H, 5.25; N, 5.14.

[0298] Synthesis Example 10:

[0299]

[0300] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-118, and the other steps were the same to obtain compound 118 (11.65 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 797.3217 (theoretical value: 797.3226). Theoretical element content (%) C 57 H 43 N3Si: C, 85.78; H, 5.43; N, 5.27. Measured element content (%): C, 85.74; H, 5.41; N, 5.29.

[0301] Synthesis Example 11:

[0302]

[0303] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-130, and the other steps were the same to obtain compound 130 (11.19 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 745.2921 (theoretical value: 745.2913). Theoretical element content (%) C53 H 39 N3Si: C, 85.33; H, 5.27; N, 5.63. Measured element content (%): C, 85.35; H, 5.24; N, 5.61.

[0304] Synthesis Example 12:

[0305]

[0306] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-144, and the other steps were the same to obtain compound 144 (11.67 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 821.3236 (theoretical value: 821.3226). Theoretical element content (%) C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured element content (%): C, 86.25; H, 5.26; N, 5.14.

[0307] Synthesis Example 13:

[0308]

[0309] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-149, and the other steps were the same to obtain compound 149 (11.27 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 771.3078 (theoretical value: 771.3070). Theoretical element content (%) C 55 H 41 N3Si: C, 85.57; H, 5.35; N, 5.44. Measured element content (%): C, 85.59; H, 5.33; N, 5.45.

[0310] Synthesis Example 14:

[0311]

[0312] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-158, and the other steps were the same to obtain compound 158 (11.11 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 711.2715 (theoretical value: 711.2706). Theoretical element content (%) C 49 H 37 N3OSi: C, 82.67; H, 5.24; N, 5.90. Measured element content (%): C, 82.63; H, 5.22; N, 5.93.

[0313] Synthesis Example 15:

[0314]

[0315] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-170, and the other steps were the same to obtain Compound 170 (11.98 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 787.3011 (theoretical value: 787.3019). Theoretical element content (%) C 55 H 41 N3OSi: C, 83.83; H, 5.24; N, 5.33. Measured element content (%): C, 83.86; H, 5.22; N, 5.37.

[0316] Synthesis Example 16:

[0317]

[0318] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-181, and the other steps were the same to obtain Compound 181 (11.73 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 761.2853 (theoretical value: 761.2862). Theoretical element content (%) C 53 H 39 N3OSi: C, 83.54; H, 5.16; N, 5.51. Measured element content (%): C, 83.56; H, 5.17; N, 5.55.

[0319] Synthesis Example 17:

[0320]

[0321] Following the preparation method of Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-196 and c-196, respectively, and the other steps were the same to obtain compound 196 (11.67 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 767.3324 (theoretical value: 767.3332). Theoretical element content (%) C 53 H 45 N3OSi: C, 82.88; H, 5.91; N, 5.47. Measured element content (%): C, 82.85; H, 5.92; N, 5.49.

[0322] Synthesis Example 18:

[0323]

[0324] Following the preparation method of Synthesis Example 1, b-2 and c-2 were replaced with equal moles of b-215 and c-215, respectively, and the other steps were the same to obtain compound 215 (10.63 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 727.2484 (theoretical value: 727.2477). Theoretical element content (%) C 49 H 37 N3SSi: C, 80.84; H, 5.12; N, 5.77. Measured element content (%): C, 80.87; H, 5.15; N, 5.72.

[0325] Synthesis Example 19:

[0326]

[0327] Following the preparation method of Synthesis Example 1, a-2 and b-2 were replaced with equimolar amounts of a-240 and b-240, respectively, and the other steps were the same to obtain Compound 240 (11.55 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 801.2893 (theoretical value: 801.2885). Theoretical element content (%) C 57 H 43 NSSi: C, 85.35; H, 5.40; N, 1.75. Measured element content (%): C, 85.31; H, 5.42; N, 1.77.

[0328] Synthesis Example 20:

[0329]

[0330] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-242, and the other steps were the same to obtain compound 242 (11.49 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 786.3170 (theoretical value: 786.3179). Theoretical element content (%) C 55 H 42 N4Si: C, 83.93; H, 5.38; N, 7.12. Measured element content (%): C, 83.96; H, 5.37; N, 7.17.

[0331] Synthesis Example 21:

[0332]

[0333] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-253 and d-74, respectively, and the other steps were the same to obtain compound 253 (12.77 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 862.3483 (theoretical value: 862.3492). Theoretical element content (%) C 61 H 46 N4Si: C, 84.88; H, 5.37; N, 6.49. Measured element content (%): C, 84.85; H, 5.39; N, 6.48.

[0334] Synthesis Example 22:

[0335]

[0336] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-268, and the other steps were the same to obtain compound 268 (11.41 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 791.3483 (theoretical value: 791.3493). Theoretical element content (%) C 55 H 37 D5N4Si: C, 83.40; H, 5.98; N, 7.07. Measured element content (%): C, 83.45; H, 5.96; N, 7.08.

[0337] Synthesis Example 23:

[0338]

[0339] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-272, and the other steps were the same to obtain compound 272 (11.43 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 804.3076 (theoretical value: 804.3085). Theoretical element content (%) C 55 H 41 FN4Si: C, 82.06; H, 5.13; N, 6.96. Measured element content (%): C, 82.09; H, 5.15; N, 6.94.

[0340] Synthesis Example 24:

[0341]

[0342] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-242 and d-273, respectively, and the other steps were the same to obtain compound 273 (12.10 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 863.3453 (theoretical value: 863.3444). Theoretical element content (%) C 60 H 45 N5Si: C, 83.40; H, 5.25; N, 8.10. Measured element content (%): C, 83.45; H, 5.24; N, 8.12.

[0343] Synthesis Example 25:

[0344]

[0345] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-289, and the other steps were the same to obtain compound 289 (9.66 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 661.2559 (theoretical value: 661.2549). Theoretical element content (%) C 45 H 35 N3OSi: C, 81.66; H, 5.33; N, 6.35. Measured element content (%): C, 81.63; H, 5.37; N, 6.32.

[0346] Synthesis Example 26:

[0347]

[0348] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-337, and the other steps were the same to obtain compound 337 (10.64 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 738.2824 (theoretical value: 738.2815). Theoretical element content (%) C 50 H 38 N4OSi: C, 81.27; H, 5.18; N, 7.58. Measured element content (%): C, 81.23; H, 5.16; N, 7.59.

[0349] Synthesis Example 27:

[0350]

[0351] Following the preparation method of Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-390 and c-390, respectively, and the other steps were the same to obtain compound 390 (11.62 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 853.2939 (theoretical value: 853.2947). Theoretical element content (%) C 59 H 43 N3SSi: C, 82.96; H, 5.07; N, 4.92. Measured element content (%): C, 82.98; H, 5.03; N, 4.95.

[0352] Synthesis Example 28:

[0353]

[0354] Following the preparation method of Synthesis Example 1, compound 392 (11.79 g) was obtained by replacing b-2 and c-2 with equimolar amounts of b-392 and c-392, respectively, with the remaining steps remaining the same. The HPLC purity was ≥99.91%. Mass spectrum m / z: 829.2955 (theoretical value: 829.2947). Theoretical element content (%): C 57 H 43 N3SSi: C, 82.47; H, 5.22; N, 5.06. Measured element content (%): C, 82.45; H, 5.21; N, 5.03.

[0355] Synthesis Example 29:

[0356]

[0357]

[0358] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-413, and the other steps were the same to obtain compound 413 (10.94 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 738.2822 (theoretical value: 738.2815). Theoretical element content (%) C 50 H 38 N4OSi: C, 81.27; H, 5.18; N, 7.58. Measured element content (%): C, 81.23; H, 5.16; N, 7.59.

[0359] Synthesis Example 30:

[0360]

[0361] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equal moles of b-452 and d-452, respectively, and the other steps were the same to obtain compound 452 (12.13 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 830.2889 (theoretical value: 830.2899). Theoretical element content (%) C 56 H 42 N4SSi: C, 80.93; H, 5.09; N, 6.74. Measured element content (%): C, 80.95; H, 5.08; N, 6.71.

[0362] Synthesis Example 31:

[0363]

[0364] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-469, and the other steps were the same to obtain compound 469 (9.47 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 622.2544 (theoretical value: 622.2553). Theoretical element content (%) C 42 H 34 N4Si: C, 80.99; H, 5.50; N, 9.00. Measured element content (%): C, 80.95; H, 5.52; N, 9.05.

[0365] Synthesis Example 32:

[0366]

[0367] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-558, and the other steps were the same to obtain compound 558 (10.65 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 749.2984 (theoretical value: 749.2975). Theoretical element content (%) C 51 H 39 N5Si: C, 81.68; H, 5.24; N, 9.34. Measured element content (%): C, 81.64; H, 5.25; N, 9.36.

[0368] Synthesis Example 33:

[0369]

[0370] Following the preparation method of Synthesis Example 1, b-2 was replaced with an equal molar amount of b-571, and the other steps were the same to obtain compound 571 (10.27 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 722.2875 (theoretical value: 722.2866). Theoretical element content (%) C50 H 38 N4Si: C, 83.07; H, 5.30; N, 7.75. Measured element content (%): C, 83.05; H, 5.34; N, 7.73.

[0371] Synthesis Example 34:

[0372]

[0373] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-584 and d-74, respectively, and the other steps were the same to obtain compound 584 (12.05 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 813.3530 (theoretical value: 813.3539). Theoretical element content (%) C 58 H 47 N3Si: C, 85.57; H, 5.82; N, 5.16. Measured element content (%): C, 85.59; H, 5.83; N, 5.13.

[0374] Synthesis Example 35:

[0375]

[0376] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-644 and d-74, respectively, and the other steps were the same to obtain compound 644 (12.75 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 849.3529 (theoretical value: 849.3539). Theoretical element content (%) C 61 H 47 N3Si: C, 86.18; H, 5.57; N, 4.94. Measured element content (%): C, 86.14; H, 5.55; N, 4.97.

[0377] Synthesis Example 36:

[0378]

[0379] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-684 and d-74, respectively, and the other steps were the same to obtain compound 684 (11.84 g) with HPLC purity ≥99.97%. Mass spectrum m / z: 778.3547 (theoretical value: 778.3540). Theoretical element content (%) C 55 H 38 D5N3Si: C, 84.79; H, 6.21; N, 5.39. Measured element content (%): C, 84.77; H, 6.23; N, 5.36.

[0380] Synthesis Example 37:

[0381]

[0382] Following the preparation method of Synthesis Example 1, compound 693 (11.86 g) was obtained by replacing b-2 with an equal molar amount of d-74 and following the same other steps. HPLC purity was ≥99.95%. Mass spectrum m / z: 769.3301 (theoretical value: 769.3309). Theoretical element content (%): C 52 H 47 N3Si2: C, 81.10; H, 6.15; N, 5.46. Measured element content (%): C, 81.14; H, 6.16; N, 5.42.

[0383] Synthesis Example 38:

[0384]

[0385] Following the preparation method of Synthesis Example 1, a-2 and b-2 were replaced with equimolar amounts of a-240 and b-749, respectively, and the other steps were the same to obtain compound 749 (11.28 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 751.3642 (theoretical value: 751.3634). Theoretical element content (%) C 55 H 49 NSi: C, 87.84; H, 6.57; N, 1.86. Measured element content (%): C, 87.87; H, 6.52; N, 1.83.

[0386] Synthesis Example 39:

[0387]

[0388] Following the preparation method of Synthesis Example 1, b-2 and d-2 were replaced with equimolar amounts of b-196 and d-770, respectively, and the remaining steps were the same to obtain compound 770 (12.57 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 897.3184 (theoretical value: 897.3175). Theoretical element content (%) C 64 H 43 N3OSi: C, 85.59; H, 4.83; N, 4.68. Measured element content (%): C, 85.57; H, 4.86; N, 4.67.

[0389] Synthesis Example 40:

[0390]

[0391] Following the preparation method of Synthesis Example 1, compound 825 (11.36 g) was obtained, with HPLC purity ≥ 99.93%, by replacing b-2, c-2, and d-2 with equimolar amounts of b-825, c-825, and d-74, respectively. The remaining steps were the same. Mass spectrum m / z: 799.3122 (theoretical value: 799.3131). Theoretical element content (%): C 55 H 41 N5Si: C, 82.57; H, 5.17; N, 8.75. Measured element content (%): C, 82.52; H, 5.16; N, 8.77.

[0392] Synthesis Example 41:

[0393]

[0394] Following the preparation method of Synthesis Example 1, compound 838 (9.82 g) was obtained, with HPLC purity ≥ 99.94%. Compound b-2, c-2, and d-2 were replaced with equimolar amounts of b-838, c-838, and d-74, respectively. The remaining steps were the same, yielding compound 838. Theoretical element content (%) was C. 49 H 40 N4Si: C, 82.55; H, 5.66; N, 7.86. Measured element content (%): C, 82.58; H, 5.67; N, 7.82.

[0395] Synthesis Example 42:

[0396]

[0397] Under nitrogen, d1-10 (9.03 g, 40 mmol), e-10 (12.85 g, 40 mmol), sodium tert-butoxide (5.76 g, 60 mmol), Pd(dppf)Cl2 (292 mg, 0.4 mmol), and toluene (250 ml) were added to a reaction flask and stirred at reflux for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / methanol (4:1) to obtain D-10 (14.36 g, 77%); HPLC purity was ≥99.87%.

[0398] Under nitrogen, D-10 (9.33 g, 20 mmol), f-10 (6.77 g, 40 mmol), sodium tert-butoxide (4.61 g, 48 mmol), Pd2(dba)3 (183 mg, 0.2 mmol), tri-tert-butylphosphine (81 mg, 0.4 mmol), and toluene (150 ml) were added to a reaction flask and reacted under reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to obtain compound 2-10 (11.71 g, 80%); HPLC purity ≥99.97%. Mass spectrum m / z: 731.3305 (theoretical value: 731.3300). Theoretical element content (%): C 54 H 41 N3: C, 88.61; H, 5.65; N, 5.74. Measured element content (%): C, 88.65; H, 5.63; N, 5.71.

[0399] Synthesis Example 43:

[0400]

[0401] According to the preparation method of Synthesis Example 42, e-10 and f-10 were replaced with equimolar amounts of e-242 and f-242, respectively, to obtain compound 2-242 (14.03 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 887.4235 (theoretical value: 887.4239). Theoretical element content (%) C 66 H 53 N3: C, 89.25; H, 6.02; N, 4.73. Measured element content (%): C, 89.22; H, 6.05; N, 4.75.

[0402] Device Examples

[0403] In the present invention, the ITO substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, then ultrasonically cleaned twice with deionized water for 10 minutes each time. The substrate is then ultrasonically cleaned for 20 minutes each in acetone and isopropyl alcohol, followed by drying at 120°C. All organic materials are sublimated to a purity of over 99.99%.

[0404] 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 measure the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System. The test environment was ambient air and room temperature.

[0405] Example 1: Preparation of organic electroluminescent device 1

[0406] HT-1:HI-1=97:3 (wt%) was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 60 nm; HT-2 was vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; RH-1 and RH-2 were vacuum evaporated on the second hole transport layer at a ratio of 1:1 (wt%), and the dopant Ir(piq)3 was evaporated at a doping amount of 7 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 30 nm; BCP was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; the compound 2 of the present invention was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; Liq was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0407] Examples 2 to 30: Preparation of organic electroluminescent devices 2 to 30

[0408] The compound 2 in the electron transport layer of Example 1 was replaced by compound 22, compound 38, compound 69, compound 74, compound 88, compound 90, compound 97, compound 106, compound 118, compound 158, compound 170, compound 181, compound 196, compound 215, compound 240, compound 242, compound 253, compound 268, compound 273, compound 289, compound 337, compound 390, compound 392, compound 413, compound 452, compound 469, compound 584, compound 693, and compound 770, respectively. The other steps were the same to obtain organic electroluminescent devices 2 to 30.

[0409] Comparative Examples 1-2: Preparation of Comparative Organic Electroluminescent Devices 1-2

[0410] The compound 2 in the electron transport layer of Example 1 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 and 2.

[0411]

[0412] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 1 to 30 of the present invention and Comparative Examples 1 to 2 are shown in Table 1.

[0413] Table 1

[0414]

[0415]

[0416] As can be seen from Table 1, the fluorene compound of Formula 1 of the present invention is used as an electron transport material in an organic electroluminescent device, and the performance of the device is significantly improved, specifically, the driving voltage is lower, the luminous efficiency is significantly higher, and the service life is longer.

[0417] Example 31: Preparation of organic electroluminescent device 31

[0418] HT-1:HI-1=97:3 (wt%) was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 60 nm; HT-2 was vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; RH-3 and RH-4 were vacuum evaporated on the second hole transport layer at a ratio of 1:1 (wt%), and the dopant Ir(piq)2(acac) was added at a ratio of 1:1 (wt%). Based on the total amount of the host and the dopant, 8 wt% of the doping amount was evaporated to form a light-emitting layer with a thickness of 30 nm; the compound 2 of the present invention was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; ET-1:Liq = 1:1 (wt%) was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; Liq was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0419] Examples 32-60: Preparation of organic electroluminescent devices 32-60

[0420] The compound 2 in the hole blocking layer of Example 31 was replaced with compound 22, compound 38, compound 69, compound 74, compound 88, compound 97, compound 106, compound 118, compound 158, compound 170, compound 181, compound 196, compound 215, compound 242, compound 253, compound 268, compound 272, compound 273, compound 289, compound 337, compound 390, compound 392, compound 413, compound 452, compound 469, compound 558, compound 571, compound 693, and compound 770, respectively, and the other steps were the same to obtain organic electroluminescent devices 32 to 60.

[0421] Comparative Examples 2 to 4: Preparation of Comparative Organic Electroluminescent Devices 2 to 4

[0422] The compound 2 in the hole blocking layer of Example 31 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 2 to 4.

[0423]

[0424] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 31 to 60 of the present invention and Comparative Examples 2 to 4 are shown in Table 2.

[0425] Table 2

[0426]

[0427]

[0428] As can be seen from Table 2, the fluorene compound of Formula 1 of the present invention is used as a hole-blocking material in an organic electroluminescent device, and the performance of the device is significantly improved, specifically, the driving voltage is lower, the luminous efficiency is significantly higher, and the service life is longer.

[0429] Example 61: Preparation of organic electroluminescent device 61

[0430] HT-1:HI-1=97:3 (wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 60 nm; the compound 2-29 of the present invention was vacuum-deposited on the hole transport layer as a luminescent auxiliary layer with a thickness of 15 nm; GH-1 and GH-2 were vacuum-deposited on the luminescent auxiliary layer at a ratio of 1:1 (wt%), and the dopant Ir(ppy)3 was added to the main body. and a doping amount of 10 wt% of the total amount of the dopant to form a light-emitting layer with a thickness of 30 nm; the compound 2 of the present invention was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; ET-2:Liq=1:1 (wt%) was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; Liq was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0431] Examples 62-90: Preparation of organic electroluminescent devices 62-90

[0432] The compound 2 in the hole blocking layer of Example 61 was replaced by compound 22, compound 38, compound 69, compound 74, compound 88, compound 97, compound 106, compound 118, compound 130, compound 144, compound 149, compound 158, compound 170, compound 181, compound 196, compound 215, compound 242, compound 253, compound 289, compound 392, compound 413, compound 452, compound 644, compound 684, compound 693, compound 749, compound 770, compound 825, and compound 838, respectively; the compound 2-29 in the light-emitting auxiliary layer was replaced by compound 2-32, compound 2-258, compound 2-39, compound 2-40, compound 2-59, compound 2-60, compound 2-71, compound 2-80, compound 2-91, compound 2-92, compound 2-93, compound 2-94, compound 2-95, compound 2-97, compound 2-98, compound 2-99, compound 3-100, compound 3-111, compound 3-112, compound 3-113 Compound 2-30, compound 2-19, compound 2-272, compound 2-8, compound 2-281, compound 2-10, compound 2-63, compound 2-2, compound 2-120, compound 2-140, compound 2-322, compound 2-355, compound 2-319, compound 2-290, compound 2-365, compound 2-242, compound 2-357, compound 2-167, compound 2-179, compound 2-422, compound 2-151, compound 2-102, compound 2-124, compound 2-336, compound 2-225, compound 2-399, compound 2-202, and the other steps are the same to obtain organic electroluminescent devices 62 to 90.

[0433] Comparative Example 5: Preparation of Comparative Organic Electroluminescent Device 5

[0434] HT-1:HI-1=97:3 (wt%) was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 75 nm; GH-1 and GH-2 were vacuum evaporated on the hole transport layer at a ratio of 1:1 (wt%), and the dopant Ir(ppy)3 was evaporated at a doping amount of 10 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 30 nm; the compound 88 of the present invention was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; ET-2:Liq=1:1 (wt%) was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; Liq was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0435] Comparative Examples 6 to 8: Preparation of Comparative Organic Electroluminescent Devices 6 to 8

[0436] Comparative organic electroluminescent devices 6 to 8 were obtained by replacing compound 88 in the hole blocking layer of comparative example 5 with compound 181, compound 392, and compound 749, respectively, and following the same other steps.

[0437] Comparative Example 9: Preparation of Comparative Organic Electroluminescent Device 9

[0438] HT-1:HI-1=97:3 (wt%) was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 60 nm; the compound 2-167 of the present invention was vacuum-deposited on the hole transport layer as a luminescent auxiliary layer with a thickness of 15 nm; GH-1 and GH-2 were vacuum-deposited on the luminescent auxiliary layer at a ratio of 1:1 (wt%), and the dopant Ir(ppy)3 was evaporated at a doping amount of 10 wt% based on the total amount of the host and the dopant to form a luminescent layer with a thickness of 30 nm; ET-2:Liq=1:1 (wt%) was vacuum-deposited on the luminescent layer as an electron transport layer with a thickness of 40 nm; Liq was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0439] Comparative Examples 10-12: Preparation of Comparative Organic Electroluminescent Devices 10-12

[0440] The comparative organic electroluminescent devices 10 to 12 were obtained by replacing the compound 2-167 in the luminescent auxiliary layer of Comparative Example 9 with the compound 2-272, the compound 2-336, and the compound 2-355, respectively, and following the same other steps.

[0441]

[0442] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 61 to 90 of the present invention and Comparative Examples 5 to 12 are shown in Table 3.

[0443] Table 3

[0444]

[0445]

[0446]

[0447] As can be seen from Table 3, the organic electroluminescent device containing the fluorene compound of Formula 1 of the present invention in the hole blocking layer and the star-shaped compound of Formula 2 in the luminescence auxiliary layer has significantly improved device performance, specifically, lower driving voltage, higher luminous efficiency, and longer service life.

[0448] Example 91: Preparation of organic electroluminescent device 91

[0449] HAT-CN was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 5 nm; NPB was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 53 nm; BH-1:BD-1=96:4 (wt%) was vacuum evaporated on the first hole transport layer to form a first light-emitting layer with a thickness of 35 nm; ET-3 was vacuum evaporated on the first light-emitting layer as a first electron transport layer with a thickness of 25 nm; Compound 2 of the present invention:Li=98:2 (wt%) was vacuum evaporated on the first electron transport layer as an n-type charge generation layer with a thickness of 15 nm; HAT-CN was vacuum evaporated on the layer as a p-type charge generation layer with a thickness of 15 nm; NPB was vacuum evaporated on the p-type charge generation layer as a second hole transport layer with a thickness of 50 nm; BH-1:BD-1=96:4 (wt%) was vacuum evaporated on the second hole transport layer to form a second light-emitting layer with a thickness of 35 nm; ET-3 was vacuum evaporated on the second light-emitting layer as a second electron transport layer with a thickness of 30 nm; LiF was vacuum evaporated on the second electron transport layer as an electron injection layer with a thickness of 1.1 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0450] Examples 92-105: Preparation of organic electroluminescent devices 92-105

[0451] The compound 2 in the n-type charge generation layer in Example 91 was replaced with compound 22, compound 38, compound 69, compound 74, compound 88, compound 90, compound 97, compound 106, compound 118, compound 130, compound 144, compound 149, compound 558, and compound 571, respectively, and the other steps were the same to obtain organic electroluminescent devices 92 to 105.

[0452] Comparative Example 13: Preparation of Comparative Organic Electroluminescent Device 13

[0453] The comparative organic electroluminescent device 13 was obtained by replacing the compound 2 in the n-type charge generation layer in Example 91 with R-3 and following the same other steps.

[0454]

[0455] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 91 to 105 of the present invention and Comparative Example 13 are shown in Table 4.

[0456] Table 4 Luminescence characteristics test data of organic electroluminescent devices

[0457]

[0458] As can be seen from Table 4, when the fluorene compound of Formula 1 of the present invention is used as an n-type charge generating material of a stacked organic electroluminescent device, the organic electroluminescent device exhibits excellent performance, specifically, high luminous efficiency and long service life.

[0459] 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 fluorene compound, characterized in that: It is expressed by the following formula 1: Wherein, the X is the same or different and is selected from C(R x ) or N, and at least one is selected from N; said R x the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl; The Ar is selected from one of the groups shown below, The a1 is selected from an integer of 0 to 4, the a2 is selected from an integer of 0 to 5, and the f0 is selected from an integer of 0 to 2; The R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl; The R 1a the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl; The E's are the same or different and are selected from C(R e ) or N, The F are the same or different and are selected from C(R e ) or N, and at least one F is selected from N, The R e The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R e bonded to each other to form a substituted or unsubstituted ring; The ring A is selected from a substituted or unsubstituted C3-C30 alicyclic ring; Said X1 is selected from O, S or N(R x1 ), wherein X2 is selected from O, S or N(R x2 ), wherein Y1 is selected from CH or N; wherein R x1 、R x2 independently selected from one of hydrogen, deuterium, tritium, 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 C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl; The Y is the same or different and is selected from C(R y ) or N; said R y The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R y bonded to each other to form a substituted or unsubstituted ring; The Z are the same or different and are selected from C(R z ) or N; said R z The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R z bonded to each other to form a substituted or unsubstituted ring; The R0 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl; Ar0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl; The L0 and L1 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof; The L2 is selected from a single bond, one of the following groups or a combination thereof, The W are the same or different and are selected from C(R w ) or N; said R w The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R w bonded to each other to form a substituted or unsubstituted ring; The X0 is selected from O, S or N (R x0 ), the R x0 One selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl; The b is selected from integers of 0-3.

2. The fluorene compound according to claim 1, characterized in that The Ar is selected from one of the groups shown below, a1 is selected from integers of 0 to 4, a2 is selected from integers of 0 to 5, a3 is selected from integers of 0 to 3, a4 is selected from integers of 0 to 7, a5 is selected from integers of 0 to 9, a6 is selected from integers of 0 to 6, a7 is selected from integers of 0 to 2, a8 is selected from integers of 0 to 8, a9 is selected from integers of 0 to 10, and f0 is selected from integers of 0 to 2; The R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl; The R 1a the same or different ones selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl; The R e The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R e bonded to each other to form a substituted or unsubstituted ring; The R e1 The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R e1 bonded to each other to form a substituted or unsubstituted ring; Said X1 is selected from O, S or N(R x1 ), wherein X2 is selected from O, S or N(R x2 ); the R x1 、R x2 independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl.

3. The fluorene compound according to claim 1, characterized in that described One selected from the following groups, The b1 is selected from an integer of 0 to 4, the b2 is selected from an integer of 0 to 6, and the b3 is selected from an integer of 0 to 3; The R z the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R z bonded to each other to form a substituted or unsubstituted ring; Ar0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl; The L0 is selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 condensed polycyclic group, and a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof.

4. The fluorene compound according to claim 1, characterized in that described wherein R0 is the same or different and is selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl ... substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted spirofluorenoxanthenyl , substituted or unsubstituted spirofluorenthioanthracenyl, substituted or unsubstituted spirofluorenazanthracenyl, substituted or unsubstituted spiroanthracenyl, 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 quinazoline, substituted or unsubstituted quinoxalinyl.

5. The fluorene compound according to claim 1, characterized in that The L0 and L1 are independently selected from a single bond, one of the following groups or a combination thereof, The Q is the same or different and is selected from C(R q ) or N; The R q the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R q bonded to each other to form a substituted or unsubstituted ring; The X4 is selected from C(R x4 )2、O、S or N(R x4 ), the R x4 the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x4 bonded to each other to form a substituted or unsubstituted ring; The L 01 , L 02 independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzocyclobutene group, a substituted or unsubstituted benzocyclobutenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted dihydroindenylene group, a substituted or unsubstituted dihydronaphthylene group, a substituted or unsubstituted tetrahydronaphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, and a substituted or unsubstituted pyridazinylene group; The a is selected from integers of 0-4.

6. The fluorene compound according to claim 1, characterized in that The L0 and L1 are independently selected from a single bond, one of the following groups or a combination thereof, The d is selected from an integer of 0 to 4, the d1 is selected from an integer of 0 to 3, and the d2 is selected from an integer of 0 to 2; The R q the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R q bonded to each other to form a substituted or unsubstituted ring; The R x4 The same or different R is selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x4 bonded to each other to form a substituted or unsubstituted ring; The L 01 、L 02 independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzocyclobutanediyl group, a substituted or unsubstituted benzocyclobutenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted dihydroindenylene group, a substituted or unsubstituted dihydronaphthylene group, a substituted or unsubstituted tetrahydronaphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, and a substituted or unsubstituted pyridazinylene group.

7. The fluorene compound according to claim 1, characterized in that The L2 is selected from a single bond, one of the following groups or a combination thereof, The e is selected from an integer of 0 to 4, the e1 is selected from an integer of 0 to 3, and the e2 is selected from an integer of 0 to 2; The R w The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R w bonded to each other to form a substituted or unsubstituted ring; The R x0 One selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl.

8. The fluorene compound according to claim 1, characterized in that The fluorene compound is selected from at least one of the structures shown below:

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device contains the fluorene compound according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes a hole transport region, and the hole transport region contains a star-shaped compound of formula 2. The Ar 21 ~Ar 26 One independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 fused polycyclic group, or a substituted or unsubstituted C2-C60 heteroaryl group; The L 21 ~L 26 independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof; The L 11 ~L 13 independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof; The f is selected from an integer of 0 to 3; The R 01 The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent R 01 They are bonded to each other to form a substituted or unsubstituted ring.

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