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 provided by the invention has relatively high electron mobility, can promote the balance of electron and hole concentration in a luminescent layer, improves the luminous efficiency and service life of the device when being applied to an electron transport layer or a hole barrier layer of the organic electroluminescent device, and further improves the performance when being applied to the luminescent layer as a main body. Meanwhile, since the compound provided by the invention has high carrier generation capability, when the compound is applied to a charge generation layer of a laminated device, the luminous efficiency of the device is improved, and the service life of the device is prolonged. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

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 Light-Emitting Diodes (OLEDs), also known as organic electroluminescent devices (OLEDs), are current-generating organic light-emitting devices. OLED displays offer far greater advantages than LCDs: they are thinner and lighter, boast significantly higher brightness, lower power consumption, faster response times, improved clarity, greater flexibility, and higher luminous efficiency. These advantages make them well-suited to meeting consumers' evolving demands for display technology.

[0003] OLEDs primarily emit light through the injection and recombination of charge carriers, with the intensity of the light being proportional to the injected current. Under the influence of an electric field, holes generated at the anode and electrons generated at the cathode migrate, injecting into the hole transport layer and electron transport layer, respectively, before migrating to the light-emitting layer. When these two materials meet in the light-emitting layer, they generate energy excitons, which excite the luminescent molecules and produce visible light. An OLED device primarily consists of a substrate, cathode, anode, hole injection layer, electron injection layer, hole transport layer, electron transport layer, electron blocking layer, hole blocking layer, and light-emitting layer. However, due to the inherent electron-rich nature of organic molecules, their hole transport capacity is often superior to their electron transport capacity. Therefore, designing excellent electron transport materials, hole blocking materials, and n-type host materials with electron transport properties is crucial to improving OLED luminescence efficiency and extending device life.

[0004] With the widespread adoption of OLEDs in small and medium-sized displays, medium and large-sized OLED screens are placing higher demands on brightness and lifespan, leading to the emergence of stacked OLED structures. Stacked OLEDs connect two or more light-emitting units in series via an n-type or p-type charge generation layer (connector layer). By designing and optimizing appropriate charge generation layer materials, the performance and stability of light-emitting devices can be improved.

[0005] After years of development, the OLED device structure system has become increasingly mature, but as new display applications have put higher requirements on the brightness and lifespan of OLED devices, the development of better OLED materials and more optimal OLED device structures has become the focus of current research. Summary of the Invention

[0006] In response to the problems existing in the prior art, the present invention provides a fluorene compound and an organic electroluminescent device thereof. Since the fluorene compound provided by the present invention has high electron mobility and charge generation ability, it can effectively balance holes and electrons. By applying it to the electron transport region or n-type charge generation layer, an organic electroluminescent device with high efficiency and long life can be developed, which solves the problems of low luminous efficiency and short service life of organic electroluminescent devices in the prior art.

[0007] Specifically, it has the general formula shown in Structural Formula 1,

[0008]

[0009] Wherein, Ar1 is selected from any one of a C3-C15 alicyclic group substituted or unsubstituted by R1, a fused ring group of a C3-C15 alicyclic ring and a C6-C30 aromatic ring substituted or unsubstituted by R1, a C6-C30 aryl group substituted or unsubstituted by R1, a C2-C30 heteroaryl group substituted or unsubstituted by R1, and a C1-C25 heterocycloalkyl group substituted or unsubstituted by R1;

[0010] The R1 is selected from any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, and at least one R1 is selected from cyano;

[0011] Ar2 is selected from any one of a substituted or unsubstituted C3-C15 alicyclic group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted C2-C25 heterocycloalkyl group;

[0012] The x are identically or differently selected from C(R2) or N atoms, the x at the bonding site is selected from C, and at least one x is selected from N atoms;

[0013] R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0014] The R aAny one selected from the following groups or their combinations:

[0015]

[0016] The v is selected from C (R3) or N atoms, the v at the bonding site is selected from C;

[0017] Said Y1 is selected from an O atom, a S atom or N(R4);

[0018] Said Y2 is selected from O atom, S atom, N(R5) or C(R6 R7);

[0019] The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0020] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, and at least one R3 is selected from any one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C9 alicyclic group;

[0021] R4 and R5 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0022] R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or R6 and R7 are connected to form a substituted or unsubstituted ring;

[0023] The R b Any one selected from substituted or unsubstituted C1-C15 alkyl or the following groups or combinations thereof,

[0024]

[0025] The z are selected from C(R8) or N atoms, the z at the bonding site is selected from C;

[0026] The ring B is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0027] Said Y3 is selected from O atom, S atom or N(R 11 );

[0028] Said Y4 is selected from C(R 12 ) or N atom, Y4 at the bonding site is selected from C;

[0029] The R8, R 12 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R8 are connected to each other to form a substituted or unsubstituted ring;

[0030] The R9, R 10 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R9 and R 10 Connected to each other to form a substituted or unsubstituted ring;

[0031] The R 11 Any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0032] The R b It can be a single bond to L0;

[0033] The R c 、R d independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, or the two adjacent R c, two R d are connected to each other to form a substituted or unsubstituted ring; said n1 is independently selected from 0, 1, 2, 3 or 4;

[0034] The L0, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic group and C6-C30 aromatic ring condensed group, or any combination thereof.

[0035] The present invention also provides an organic electroluminescent device comprising an anode, an organic layer and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the fluorene compound of the present invention.

[0036] Beneficial effects:

[0037] The present invention provides a fluorene compound having high electron mobility and capable of promoting the balance of electron and hole concentrations in the light-emitting layer. When applied to the electron transport layer or hole blocking layer of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved. When applied as an n-type host to the light-emitting layer of an OLED, the fluorene compound not only improves the brightness and efficiency of the device but also further enhances its performance by optimizing the device structure. Furthermore, because the compound of the present invention has a high carrier generation capability, its application in the n-type charge generation layer of a stacked organic electroluminescent device further improves the luminous efficiency and service life of the organic electroluminescent device. DETAILED DESCRIPTION

[0038] 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.

[0039] In the compounds of the present invention, any atom not designated as a specific isotope includes any stable isotope of that atom, and includes atoms at both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain approximately 0.0156 atomic % deuterium per hydrogen atom.

[0040] As used herein, the terms "H" and "hydrogen" refer to hydrogen atoms in a chemical structure containing no more than the natural abundance of deuterium or tritium atoms, e.g., no more than 0.0156 atomic % of deuterium. "D" and "deuterium" refer to deuterium with an abundance above the natural abundance, e.g., any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, e.g., approximately 95 atomic % of the deuterium content. As used herein, "H" or "hydrogen" is represented by omitting unillustrated hydrogen atoms.

[0041] Examples of the halogen according to the present invention may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0042] The "C8-C30" in the "substituted or unsubstituted C8-C30 fused aryl group" of the present invention refers to the number of carbon atoms in the unsubstituted "fused aryl group" and does not include the number of carbon atoms in the substituent. The "C1-C15" in the "substituted or unsubstituted C1-C15 alkyl group" refers to the number of carbon atoms in the unsubstituted "alkyl group" and does not include the number of carbon atoms in the substituent. And so on.

[0043] The fused aryl group described in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from two or more aromatic hydrocarbons. In this case, the two or more rings can be attached to each other simply or in a condensed form. The number of carbon atoms in the fused aryl group is C8 to C30, preferably C8 to C15. The fused aryl group includes, but is not limited to, the following groups: phenanthrenyl, anthracenyl, fluoranthenyl, pyrenyl, triphenylene, perylene, etc.

[0044] The alkyl group herein refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has a carbon number of C1 to C15, preferably C1 to C10. Examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and tridecyl.

[0045] The chain alkyl group having more than three carbon atoms described in the present invention includes its isomers. For example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on.

[0046] The alicyclic group described herein refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which may be fully or partially unsaturated. Examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, and cycloheptene. Multiple monocyclic hydrocarbons can be linked in various ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; and several rings can be linked together to form a cage-like structure. Examples include, but are not limited to, adamantane, norbornane, and camphane.

[0047] The aryl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, and condensed ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, fluorenyl, spirobifluorenyl, spiroanthrafluorenyl, benzofluorenyl, benzospirobifluorenyl, and the like.

[0048] The fused alicyclic and aromatic ring groups of the present invention refer to a monovalent group formed by fusion of an alicyclic and aromatic rings and removal of one hydrogen atom. Examples of the fused alicyclic and aromatic ring groups include, but are not limited to, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclobutenyl, benzocycloheptanyl, and benzocycloheptenyl. The alicyclic rings have a carbon number of C3 to C15, preferably C3 to C10. The aromatic rings have a carbon number of C6 to C30, preferably C6 to C18, and more preferably C6 to C12.

[0049] The heteroaryl group described herein refers to a monovalent group in which at least one carbon atom in the aromatic nucleus of an aromatic group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2-C30, preferably C2-C15, and more preferably C2-C10. The heteroatoms include, but are not limited to, O, S, N, Si, B, P, and the like. The heteroaryl group includes monocyclic heteroaryl groups and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, furyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, and the like.

[0050] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k )3 groups, wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each R kThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. The "alkylsilyl" group is at least one substituent R of a silyl group (-SiH3) k is an alkyl group, and preferred alkylsilyl groups include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the "arylsilyl group" is at least one substituent R of the silyl group (-SiH3) k is an aryl group, and preferred arylsilyl groups specifically include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and the like, but are not limited thereto.

[0051] The arylene group described in the present invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon nucleus in an aromatic hydrocarbon molecule. The number of carbon atoms in the arylene group is C6 to C30, preferably C6 to C20, and more preferably C6 to C10. 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 include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, perylene, pyrenylene, indenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, spirobifluorenylene, benzospirobifluorenylene, etc.

[0052] The sub-fused ring group of an alicyclic ring and an aromatic ring described in the present invention refers to a general term for a divalent group remaining after the alicyclic ring and aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-fused ring group of an alicyclic ring and an aromatic ring may include, but are not limited to, indanylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropanediylene, benzocyclobutanediylene, benzocyclobutenylene, naphthocyclopentanediylene, etc. The number of carbon atoms in the alicyclic ring is C3-C15, preferably C3-C10. The number of carbon atoms in the aromatic ring is C6-C30, preferably C6-C18.

[0053] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The number of carbon atoms in the heteroarylene group is C2 to C30, preferably C2 to C20, and more preferably C2 to C10. The heteroatoms include, but are not limited to, the following atoms: O, S, N, Si, B, P, etc. 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, but are not limited to, the following groups: pyridylene, pyrimidylene, quinolylene, isoquinolylene, furylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thienylene, benzothienylene, dibenzothienylene, benzodibenzothienylene, etc.

[0054] The "unsubstituted" in the "substituted or unsubstituted" of the present invention means that the hydrogen atoms on the group are not replaced by any substituents, and "substituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different, and the position of the hydrogen atoms replaced by the substituents may be arbitrary.

[0055] The substituent group represented by "substituted" in the above "substituted or unsubstituted" is selected from one of the following groups, a deuterium atom, a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C12 cycloalkane group alkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, Ethyl-substituted cyclobutanyl, deuterated cyclobutanyl, cyclopentanyl, methyl-substituted cyclopentanyl, ethyl-substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl-substituted cyclohexanyl, ethyl-substituted cyclohexanyl, n-propyl-substituted cyclohexanyl, n-butyl-substituted cyclohexanyl, cyclohexane-substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, Piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthrenyl, deuterated phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl; when substituted with multiple substituents, the multiple substituents may be the same or different.

[0056] In the present specification, when the bond at a substituent or a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the rings.

[0057] For example, Can be represented Can be represented And so on.

[0058] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring.

[0059] For example, Can be represented Can represent Can be represented And so on.

[0060] In the present invention, "two adjacent groups can be connected to each other to form a substituted or unsubstituted ring" means that the adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. The following examples are shown:

[0061]

[0062] In the present invention, the ring formed by connection can be a five-membered ring, a six-membered ring or a condensed ring, such as benzene, naphthalene, phenanthrene, triphenylene, cyclopentane, cyclohexane, cyclopentene, cyclohexene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but is not limited thereto.

[0063] In the present invention, at least one means one, two, three, four, five, six or more.

[0064] The present invention provides a fluorene compound having the general formula shown in Structural Formula 1.

[0065]

[0066] Wherein, Ar1 is selected from any one of a C3-C15 alicyclic group substituted or unsubstituted by R1, a fused ring group of a C3-C15 alicyclic ring and a C6-C30 aromatic ring substituted or unsubstituted by R1, a C6-C30 aryl group substituted or unsubstituted by R1, a C2-C30 heteroaryl group substituted or unsubstituted by R1, and a C1-C25 heterocycloalkyl group substituted or unsubstituted by R1;

[0067] The R1 is selected from any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, and at least one R1 is selected from cyano;

[0068] Ar2 is selected from any one of a substituted or unsubstituted C3-C15 alicyclic group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted C2-C25 heterocycloalkyl group;

[0069] The x are identically or differently selected from C(R2) or N atoms, the x at the bonding site is selected from C, and at least one x is selected from N atoms;

[0070] R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0071] The R a Any one selected from the following groups or their combinations:

[0072]

[0073] The v is selected from C (R3) or N atoms, the v at the bonding site is selected from C;

[0074] Said Y1 is selected from an O atom, a S atom or N(R4);

[0075] Said Y2 is selected from O atom, S atom, N(R5) or C(R6 R7);

[0076] The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0077] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, and at least one R3 is selected from any one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C9 alicyclic group;

[0078] R4 and R5 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0079] R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or R6 and R7 are connected to form a substituted or unsubstituted ring;

[0080] The R b Any one selected from substituted or unsubstituted C1-C15 alkyl or the following groups or combinations thereof,

[0081]

[0082] The z are selected from C(R8) or N atoms, the z at the bonding site is selected from C;

[0083] The ring B is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0084] Said Y3 is selected from O atom, S atom or N(R 11 );

[0085] Said Y4 is selected from C(R 12 ) or N atom, Y4 at the bonding site is selected from C;

[0086] The R8, R 12independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R8 are connected to each other to form a substituted or unsubstituted ring;

[0087] The R9, R 10 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R9 and R 10 Connected to each other to form a substituted or unsubstituted ring;

[0088] The R 11 Any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0089] The R b It can be a single bond to L0;

[0090] The R c 、R d independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, or the two adjacent R c , two R d are connected to each other to form a substituted or unsubstituted ring; said n1 is independently selected from 0, 1, 2, 3 or 4;

[0091] The L0, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic group and C6-C30 aromatic ring condensed group, or any combination thereof.

[0092] Preferably, the formula 1 is selected from any one of the following structures:

[0093]

[0094] The n1 is independently selected from 0, 1, 2, 3 or 4; the n2 is independently selected from 0, 1, 2 or 3;

[0095] Preferably, the Select any one of the following groups, * represents the connection site:

[0096]

[0097] Preferably, the R2 are the same or different and are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, silyl or any combination thereof.

[0098] Preferably, in the formula 1 Any one selected from the following groups:

[0099]

[0100]

[0101]

[0102] The R b any one selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and silyl;

[0103] Said R3 is the same or different and is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, furanyl, thiophenyl, phenyl Any one or more of oxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted by multiple substituents, the multiple substituents are the same or different, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, and at least one R3 is selected from the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, and triphenylsilyl;

[0104] The R8, R 12 any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, wherein when substituted by multiple substituents, the multiple substituents are the same or different, or two adjacent R8 are connected to form a substituted or unsubstituted ring;

[0105] The R c 、R dR is selected from any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl. In the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R c Between the two R d They are connected to each other to form a substituted or unsubstituted ring;

[0106] The n1 is independently selected from 0, 1, 2, 3 or 4; the n2 is independently selected from 0, 1, 2 or 3;

[0107] a1 is independently selected from 1, 2, 3, 4, or 5; a2 is independently selected from 1, 2, 3, 4, 5, 6, or 7; a3 is independently selected from 1, 2, 3, or 4; a4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; a5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a6 is independently selected from 1, 2, or 3; a7 is independently selected from 1 or 2; a8 is independently selected from 1, 2, 3, 4, 5, or 6; a9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13;

[0108] Said b1 is independently selected from 1, 2, 3, 4 or 5; said b2 is independently selected from 1, 2, 3, 4, 5, 6 or 7; said b3 is independently selected from 1, 2, 3 or 4; said b4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; said b7 is independently selected from 1, 2 or 3; said b8 is independently selected from 1 or 2; said b9 is independently selected from 1, 2, 3, 4, 5 or 6.

[0109] Preferably, Ar1 is selected from any one of the following groups or combinations thereof:

[0110]

[0111] The t is selected from C (R1) or N atoms, the t at the bonding site is selected from C;

[0112] The T1 is selected from O atom, S atom or N(R 14 );

[0113] The T2 is selected from O atoms, S atoms, N (R 15 ) or C(R 16 R 17 );

[0114] The ring Q is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0115] Said R1 is independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, Any one or more of triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted with multiple substituents, the multiple substituents are the same or different, or the two adjacent R1s are connected to form a substituted or unsubstituted ring, and at least one R1 is selected from cyano;

[0116] The R 14 、R 15 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; said R 15 It may be a single bond to L1;

[0117] The R 16 、R 17 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; or said R 16 and R17 They are connected to each other to form a substituted or unsubstituted ring.

[0118] More preferably, Ar1 is selected from any one of the following groups or combinations thereof:

[0119]

[0120] Said R1 is the same or different and is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl any one or more, In the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring, and at least one R1 is selected from cyano, wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, deuterated methyl, deuterated tert-butyl, deuterated isopropyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, and quinoxalinyl;

[0121] The R 14 、R 15 、R 16 、R 17any one or more of hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other, or said R 16 and R 17 are connected to each other to form a substituted or unsubstituted ring;

[0122] The R f any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same or different;

[0123] Said c1 is independently selected from 1, 2, 3, 4 or 5; said c2 is independently selected from 1, 2, 3 or 4; said c3 is independently selected from 1 or 2; said c4 is independently selected from 1, 2 or 3; said c5 is independently selected from 1, 2, 3, 4, 5, 6 or 7; said c6 is independently selected from 1, 2, 3, 4, 5 or 6; said c7 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said c8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0124] Preferably, Ar1 has one, two, three or four R1 selected from cyano.

[0125] Preferably, Ar2 is selected from any one of the following groups or combinations thereof:

[0126]

[0127] The p is the same or different and is selected from C(R 18 ) or a N atom, and p at the bonding site is selected from C;

[0128] The Q1 is selected from O atom, S atom or N(R 19 );

[0129] The Q2 is independently selected from O atoms, S atoms, N (R 20 ) or C(R 21 R 22 );

[0130] The ring E is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0131] The R 18 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R 18 are connected to each other to form a substituted or unsubstituted ring;

[0132] The R 19 、R 20 、R 21 、R 22 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R 21 and R 22 are connected to each other to form a substituted or unsubstituted ring, or R 21 and R 22 One of them is a single bond connected to L2.

[0133] More preferably, Ar2 is selected from any one of the following groups or combinations thereof:

[0134]

[0135] The R 18R is independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, silyl or any combination thereof; or the two adjacent R 18 They can be connected to each other to form a substituted or unsubstituted ring;

[0136] The R g independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, fluorenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, silyl, or any combination thereof;

[0137] The R 19 、R 20 、R 21 、R 22 independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, fluorenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, silyl or a combination thereof, or any one of the R 21 and R 22 are connected to each other to form a substituted or unsubstituted ring;

[0138] The d1 is independently selected from 0, 1, 2, 3, 4, or 5; the d2 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d4 is independently selected from 0, 1, 2, 3, or 4; the d5 is independently selected from 0, 1, or 2; the d6 is independently selected from 0, 1, 2, or 3; the d7 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0139] Preferably, Ar2 has one, two, three or four R 18 Selected from cyano.

[0140] Preferably, L0, L1, and L2 are independently selected from a single bond, a group as shown below, or any one of their combinations:

[0141]

[0142] The r are identical or different selected from C(R 23 ) or a N atom, and r at the bonding site is selected from C;

[0143] Said E1 is selected from O atom, S atom, N(R 24 ) or C(R 25 R 26 );

[0144] Said E2 is selected from O atom, S atom or N(R 27 );

[0145] The ring G is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0146] The R 23 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R 23 are connected to each other to form a substituted or unsubstituted ring;

[0147] The R 24 、R 25 、R 26 、R 27independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R 25 and R 26 They are connected to each other to form a substituted or unsubstituted ring.

[0148] More preferably, L0, L1, and L2 are independently selected from a single bond, a group as shown below, or any one of their combinations:

[0149]

[0150]

[0151] Most preferably, the fluorene compound represented by Formula 1 is selected from any one of the chemical structures shown below:

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] The above lists some specific chemical structures of the fluorene compounds of structural formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. All fluorene compounds based on structural formula 1 and having substituents as defined above should be included.

[0178] Furthermore, the present invention also provides an organic electroluminescent device, comprising an anode, an organic layer and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the fluorene compound described in the present invention.

[0179] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one layer of a hole transport region, a light-emitting layer, and an electron transport region, and at least one layer of the electron transport region or the light-emitting layer contains the fluorene compound described in the present invention.

[0180] Preferably, the organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region or a covering layer, and an n-type charge generation layer and a p-type charge generation layer are arranged in the middle of each light-emitting layer, and the n-type charge generation layer contains the fluorene compound described in the present invention.

[0181] Preferably, the organic layer comprises an electron transport region, and the electron transport region comprises at least one of the fluorene compounds described in the present invention.

[0182] Preferably, the organic layer comprises an electron transport region, the electron transport region comprises an electron transport layer, and the electron transport layer comprises at least one of the fluorene compounds described in the present invention.

[0183] Preferably, the organic layer comprises an electron transport region, the electron transport region comprises a hole blocking layer, and the hole blocking layer comprises at least one of the fluorene compounds described in the present invention.

[0184] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the fluorene compounds described in the present invention.

[0185] Preferably, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises at least one of the compounds described in the present invention.

[0186] Preferably, the organic electroluminescent device described in the present invention is a single-layer organic electroluminescent device or a stacked organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the stacked organic electroluminescent device is an organic electroluminescent device formed by connecting N (N≥2) independent light-emitting units in series through a charge generation layer.

[0187] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, wherein an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0188] Preferably, the organic electroluminescent device described in the present invention is a stacked organic electroluminescent device, wherein a first light-emitting unit emitting light of a first color, an Nth light-emitting unit emitting light of an Nth color, and a charge generation layer for uniformly controlling the charge between the first light-emitting unit and the Nth light-emitting unit are formed between the anode and the cathode, wherein the charge generation layer includes an n-type charge generation layer arranged adjacent to the first light-emitting unit and a p-type charge generation layer arranged adjacent to the Nth light-emitting unit.

[0189] Preferably, the n-type charge generation layer contains the fluorene compound of the present invention, or the n-type charge generation layer can be formed by doping the fluorene compound of the present invention with other materials.

[0190] Preferably, the thickness of the electron transport layer is 5 to 80 nm.

[0191] More preferably, the thickness of the electron transport layer is 10 to 50 nm.

[0192] More preferably, the thickness of the electron transport layer is 15 to 40 nm.

[0193] Preferably, the hole blocking layer has a thickness of 1 to 100 nm.

[0194] More preferably, the hole blocking layer has a thickness of 2 to 60 nm.

[0195] More preferably, the hole blocking layer has a thickness of 5 to 45 nm.

[0196] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material, as long as it remains unchanged during the formation of the electrodes and the organic layer. For example, it can be made of glass, plastic, polymer film, silicon, or the like. If the substrate is opaque, the opposing electrode is preferably transparent or translucent.

[0197] 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 organic layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are respectively introduced below:

[0198] The anode of the present invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with a large work function (specifically, 4.0 eV or greater). Materials used for the anode of the present invention may include metals or their alloys, metal oxides, laminated materials, conductive polymers, and combinations of metals and oxides. Examples include, but are not limited to, nickel (Ni), platinum (Pt), vanadium (V), silver (Ag), gold (Au), zinc oxide (ZnO), indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (In2O3), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polypyrrole, polyaniline, and zinc oxide:aluminum (ZnO:Al).

[0199] The hole injection material of the present invention is preferably a material capable of reducing the interface barrier between the anode and the hole transport layer. Materials such as those described below include polycyano conjugated organic compounds, radialene compounds, phthalocyanine metal complexes, aromatic amine derivatives, polymers, and the like. Specific examples may include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and polyaniline-based and polythiophene-based conductive polymers, but are not limited thereto, and may also include other compounds capable of p-doping.

[0200] The hole transport material of the present invention is preferably a material capable of receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer, and has high hole mobility and good stability. The hole transport material of the present invention is located between the anode and the light-emitting layer, or, if a hole injection layer is present, between the hole injection layer and the light-emitting layer. Examples of such materials include aromatic amine compounds, carbazole derivatives, anthracene derivatives, and polymers. Specific examples may include N-([1,1'-biphenyl]-4-yl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan-4-amine, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N4,N4-di([1,1'-biphenyl]-4-yl)-N4'-([1,1':4',1'-terphenyl]-4-yl)- )-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine, N,N,N',N'-tetraphenylbiphenyl diamine, 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 9,10-diphenylanthracene (abbreviated as DPAnth), p-phenylenevinylene (PPV), etc., but are not limited thereto.

[0201] The electron blocking layer of the present invention preferably uses a material whose absolute value of the difference between the HOMO value of the hole transport layer and that of the hole transport layer is greater than or equal to 0.07 eV and less than or equal to 0.35 eV. Specific examples may include fluorene compounds, spirofluorene derivatives, furan derivatives and the like, such as TPD, NPB, N4, N4-bis ([1,1'-biphenyl]-4-yl) -N4'-phenyl N4'-[1,1': 4', 1"- Terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluoren-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited thereto.

[0202] The light-emitting layer of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, wherein the host material may be composed of one or more materials.

[0203] As the host material of the light-emitting layer of the present invention, it can include fused aromatic ring derivatives, heterocyclic compounds, etc., such as 9,10-di(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tri(pyrene-1-yl)benzene (TPB3), 1,3,5-tri(carbazol-9-yl)benzene (TCP), 14,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), the fluorene compound of the present invention, etc., but is not limited thereto. The fluorene compound represented by Formula 1 of the present invention is preferred.

[0204] As the guest material of the light-emitting layer of the present invention, it can include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as 4,4'-bis(4-(9H-carbazol-9-yl)phenylvinyl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-anthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenyltetracene (Rubrene), coumarin 545T (C-525T) tris(2-phenyl-3-methyl-pyridine)iridium (Ir(3mppy)3), bis(2-(naphthalene-2-yl)pyridine)(acetylacetone)iridium(III) (Ir(npy)2acac), tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), etc., but is not limited thereto.

[0205] The hole blocking layer material of the present invention needs to have good hole blocking ability so as to block holes in the light-emitting layer, such as the following materials, imidazole derivatives, phenanthroline derivatives, metal complexes, triazine derivatives, etc. Specific examples may include 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluoren-2-yl)4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine, the fluorene compounds of the present invention, etc., but are not limited thereto. Preferably, the fluorene compound represented by Formula 1 of the present invention is used.

[0206] The electron transport layer material of the present invention preferably has a material with good electron transport ability and good stability. The materials described below, imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, quinoline derivatives, oxadiazole derivatives, triazole derivatives, metal complexes, etc. Specific examples may include 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene, 2-(3-(phenanthren-9-yl)-5- (pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 1,3,5-tris(4-(pyridin-4-yl)quinolin-2-yl)benzene (TPyQB), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinolinolato)(4-phenylphenol)aluminum(III) (BAlq), lithium 8-hydroxyquinolinate (LiQ), and the fluorene compounds of the present invention, but not limited thereto. The fluorene compounds of Formula 1 of the present invention are preferred.

[0207] The electron injection layer material of the present invention is preferably a material capable of reducing the interface barrier between the cathode and the electron transport layer. Alkali metals such as lithium (Li), cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), rare earth metals such as europium (Eu), ytterbium (Yb), and compounds containing these metals can be used. As such a compound, for example: alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals can be cited. In addition, a variety of these compounds can also be used in combination.

[0208] The cathode of the present invention is preferably made of a conductor with a low work function to facilitate electron injection, and can be, for example, a metal, metal oxide, and / or a conductive polymer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; and multilayered materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but are not limited thereto.

[0209] The covering layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The covering layer material may be an organic or inorganic substance with an appropriate refractive index, such as a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic hydrocarbon compound, aromatic amine compound, etc. Specific examples may include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-bis(9-carbazole)biphenyl (CBP), etc., but are not limited thereto.

[0210] The n-type charge generation material of the present invention can be selected from the following materials or one of their combinations: tris-(8-hydroxyquinolinolato)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-phenolato)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3 -(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternating-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), the fluorene compounds described in the present invention, etc., but are not limited thereto. In addition, an auxiliary N-type charge generation material may also be included. For example, the auxiliary N-type charge generation material may be an alkali metal such as, but not limited to, Li, Cs, K, Rb, Na, or Fr, or an alkaline earth metal such as, but not limited to, Be, Mg, Ca, Sr, Ba, or Ra. Fluorene compounds represented by Formula 1 of the present invention are preferred.

[0211] The p-type charge generation material of the present invention may include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N' -bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS) and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc., but are not limited thereto.

[0212] 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.

[0213] The organic electroluminescent device of the present invention is mainly used in the field of information display technology, and is widely used in various information displays, such as tablet computers, flat-screen TVs, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable devices, etc.

[0214] Synthesis Example

[0215] 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.

[0216] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0217] There are no particular limitations on the preparation method of the fluorene compound of Structural Formula 1 of the present invention, and conventional methods known to those skilled in the art may be employed. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the fluorene compound of Structural Formula 1 of the present invention can be prepared using the synthetic route shown below.

[0218] Synthesis route:

[0219]

[0220] Said X1, X2, and X3 are halogen atoms, for example, they can be the same or different and selected from the following halogen atoms, I, Br, and Cl.

[0221] Synthesis Example 1: Preparation of Intermediate d-4

[0222]

[0223] Preparation of intermediate d-4: Under nitrogen, m-4 (34.90 g, 140.00 mmol), pinacol diboron (35.55 g, 140.00 mmol), Na2CO3 (29.68 g, 280.00 mmol), Pd(dppf)Cl2 (1.02 g, 1.40 mmol), and 900 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred at reflux for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, the solvent was concentrated by distillation under reduced pressure, the crystals were cooled, filtered, and then recrystallized from ethyl acetate to obtain intermediate d-4 (43.28 g, 78% yield); HPLC purity ≥99.85%. Mass spectrum: m / z: 396.2261 (theoretical value: 396.2248).

[0224] According to the above synthesis method, other intermediates required for the present invention are synthesized. The relevant raw materials are shown in Table 1:

[0225] Table 1:

[0226]

[0227]

[0228] Synthesis Example 2: Preparation of Intermediate d-110

[0229]

[0230] Preparation of intermediate p-1100: Under nitrogen, m-72 (41.13 g, 100.00 mmol), n-110 (15.60 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred at reflux for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene / ethanol (10:1) to obtain intermediate p-110 (32.78 g, 74% yield). HPLC purity ≥99.75%. Mass spectrum: m / z: 442.1488 (theoretical value: 442.1475).

[0231] Preparation of intermediate d-110: Under nitrogen, p-110 (26.58 g, 60.00 mmol), pinacol diboron (15.24 g, 60.00 mmol), NaCO (12.72 g, 120.00 mmol), Pd(dppf)Cl (0.44 g, 0.60 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred at reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, the solvent was concentrated by distillation under reduced pressure, the crystals were cooled, filtered, and then recrystallized from ethyl acetate to obtain intermediate d-110 (23.09 g, 72% yield); HPLC purity ≥99.79%. Mass spectrum: m / z: 534.2730 (theoretical value: 534.2745).

[0232] According to the above synthesis method, other intermediates required for the present invention are synthesized. The relevant raw materials are shown in Table 2:

[0233] Table 2:

[0234]

[0235]

[0236] Synthesis Example 3: Preparation of Compound 4

[0237]

[0238] Preparation of Intermediate A-4: Under nitrogen, a-4 (14.69 g, 100.00 mmol), b-4 (18.44 g, 100.00 mmol), KCO (20.73 g, 150.00 mmol), Pd(PPh) (1.16 g, 1.00 mmol), and 500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred at reflux for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene / ethanol (10:1) to obtain Intermediate A-4 (19.58 g, 78% yield). HPLC purity ≥99.76%. Mass spectrum: m / z: 249.9803 (theoretical value: 249.9813).

[0239] Preparation of Intermediate B-4: Under nitrogen, a reaction flask was charged with A-4 (15.06 g, 60.00 mmol), c-4 (7.32 g, 60.00 mmol), Na2CO3 (10.60 g, 100.00 mmol), Pd(dppf)Cl2 (0.44 g, 0.60 mmol), and 400 mL of toluene / ethanol / water (2:1:1). The mixture was stirred at reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene / ethanol (9:1) to obtain Intermediate B-4 (13.17 g, 75% yield). HPLC purity ≥99.88%. Mass spectrum: m / z: 292.0516 (theoretical value: 292.0533).

[0240] Preparation of compound 4: Under nitrogen protection, B-4 (11.71 g, 40.00 mmol), d-4 (15.85 g, 40.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), X-phos (0.19 g, 0.40 mmol), and 300 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask and stirred at reflux for 5.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain compound 4 (14.96 g, yield 71%), HPLC purity ≥ 99.95%, mass spectrum m / z: 526.2157 (theoretical value: 526.2139). Theoretical element content (%) C 37 H 26 N4: C, 84.38; H, 4.98; N, 10.64. Measured element content (%): C, 84.36; H, 4.96; N, 10.65.

[0241] Synthesis Example 4: Preparation of Compound 22

[0242]

[0243] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal mole of d-22 to obtain compound 22 (16.72 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 588.2314 (theoretical value: 588.2330). Theoretical element content (%) C 42 H 28 N4: C, 85.69; H, 4.79; N, 9.52. Measured element content (%): C, 85.71; H, 4.80; N, 9.50.

[0244] Synthesis Example 5: Preparation of Compound 72

[0245]

[0246] Following the same preparation method as in Synthesis Example 3, a-4, b-4, c-4, and d-4 were replaced with equimolar amounts of a-72, b-72, a-72, and d-72, respectively, to obtain compound 72 (22.31 g) with HPLC purity ≥ 99.96%. Mass spectrum m / z: 763.2965 (theoretical value: 763.2987). Theoretical element content (%): C 57 H 37 N3: C, 89.62; H, 4.88; N, 5.50. Measured element content (%): C, 89.63; H, 4.90; N, 5.48.

[0247] Synthesis Example 6: Preparation of Compound 86

[0248]

[0249] Following the same preparation method as in Synthesis Example 3, a-4, b-4, c-4, and d-4 were replaced with equimolar amounts of a-86, b-72, a-86, and d-72, respectively, to obtain compound 86 (22.19 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 763.2977 (theoretical value: 763.2987). Theoretical element content (%): C 57 H 37 N3: C, 89.62; H, 4.88; N, 5.50. Measured element content (%): C, 89.60; H, 4.89; N, 5.49.

[0250] Synthesis Example 7: Preparation of Compound 110

[0251]

[0252] Following the same preparation method as in Synthesis Example 3, a-4, b-4, c-4, and d-4 were replaced with equimolar amounts of a-72, b-72, a-72, and d-110, respectively, to obtain compound 110 (24.87 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 839.3317 (theoretical value: 839.3300). Theoretical element content (%): C 63 H 41 N3: C, 90.08; H, 4.92; N, 5.00. Measured element content (%): C, 90.10; H, 4.89; N, 5.03.

[0253] Synthesis Example 8: Preparation of Compound 137

[0254]

[0255] Following the same preparation method as in Synthesis Example 3, b-4 and d-4 were replaced with equimolar amounts of b-137 and d-1137, respectively, to obtain compound 137 (17.89 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 629.2846 (theoretical value: 629.2831). Theoretical element content (%): C 46 H 35 N3: C, 87.73; H, 5.60; N, 6.67. Measured element content (%): C, 87.72; H, 5.58; N, 6.66.

[0256] Synthesis Example 9: Preparation of Compound 175

[0257]

[0258] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-72 to obtain compound 175 (17.43 g) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 588.2332 (theoretical value: 588.2314). Theoretical element content (%) C 42 H 28 N4: C, 85.69; H, 4.79; N, 9.52. Measured element content (%): C, 85.70; H, 4.81; N, 9.49.

[0259] Synthesis Example 10: Preparation of Compound 180

[0260]

[0261] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-137 to obtain compound 180 (17.91 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 630.2793 (theoretical value: 630.2783). Theoretical element content (%) C 45 H 34 N4: C, 85.68; H, 5.43; N, 8.88. Measured element content (%): C, 85.70; H, 5.41; N, 8.87.

[0262] Synthesis Example 11: Preparation of Compound 181

[0263]

[0264] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-181 to obtain compound 181 (18.11 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 646.2538 (theoretical value: 646.2553). Theoretical element content (%) C 44 H 34 N4Si: C, 81.70; H, 5.30; N, 8.66. Measured element content (%): C, 81.68; H, 5.29; N, 8.67.

[0265] Synthesis Example 12: Preparation of Compound 217

[0266]

[0267] Following the same preparation method as in Synthesis Example 3, a-4, c-4, and d-4 were replaced with equimolar amounts of a-217, a-217, and d-217, respectively, to obtain compound 217 (19.12 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 663.2185 (theoretical value: 663.2171). Theoretical element content (%): C 45 H 25 N7: C, 81.43; H, 3.80; N, 14.77. Measured element content (%): C, 81.46; H, 3.78; N, 14.76.

[0268] Synthesis Example 13: Preparation of Compound 342

[0269]

[0270] Following the same preparation method as in Synthesis Example 3, compound 342 (20.30 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-342 and d-72, respectively. HPLC purity was ≥99.93%. Mass spectrum m / z: 704.2950 (theoretical value: 704.2940). Theoretical element content (%): C 51 H 36 N4: C, 86.90; H, 5.15; N, 7.95. Measured element content (%): C, 86.88; H, 5.16; N, 7.93.

[0271] Synthesis Example 14: Preparation of Compound 351

[0272]

[0273] Following the same preparation method as in Synthesis Example 3, compound 351 (24.28 g) was obtained by replacing c-4 and d-4 with equimolar amounts of d-72 and d-72, respectively. HPLC purity was ≥99.91%. Mass spectrum m / z: 842.3425 (theoretical value: 842.3409). Theoretical element content (%): C 62 H 42 N4: C, 88.33; H, 5.02; N, 6.65. Measured element content (%): C, 88.31; H, 5.03; N, 6.67.

[0274] Synthesis Example 15: Preparation of Compound 368

[0275]

[0276] Following the same preparation method as in Synthesis Example 3, compound 368 (18.51 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-368 and d-137, respectively. HPLC purity was ≥99.92%. Mass spectrum m / z: 670.2720 (theoretical value: 670.2733). Theoretical element content (%): C 47 H 34 N4O: C, 84.15; H, 5.11; N, 8.35. Measured element content (%): C, 84.12; H, 5.12; N, 8.37.

[0277] Synthesis Example 16: Preparation of Compound 377

[0278]

[0279] Following the same preparation method as in Synthesis Example 3, compound 368 (20.51 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-368 and d-137, respectively. HPLC purity was ≥99.91%. Mass spectrum m / z: 753.2877 (theoretical value: 753.2892). Theoretical element content (%): C 54 H 35 N5: C, 86.03; H, 4.68; N, 9.29. Measured element content (%): C, 86.05; H, 4.66; N, 9.30.

[0280] Synthesis Example 17: Preparation of Compound 378

[0281]

[0282] Following the same preparation method as in Synthesis Example 3, compound 368 (18.61 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-368 and d-137, respectively. HPLC purity was ≥99.94%. Mass spectrum m / z: 664.2645 (theoretical value: 664.2627). Theoretical element content (%): C 48 H 32 N4: C, 86.72; H, 4.85; N, 8.43. Measured element content (%): C, 86.74; H, 4.83; N, 8.41.

[0283] Synthesis Example 18: Preparation of Compound 379

[0284]

[0285] Following the same preparation method as in Synthesis Example 3, compound 379 (21.34 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-379 and d-137, respectively. HPLC purity was ≥99.95%. Mass spectrum m / z: 730.3078 (theoretical value: 730.3096). Theoretical element content (%): C 53 H 38 N4: C, 87.09; H, 5.24; N, 7.67. Measured element content (%): C, 87.11; H, 5.22; N, 7.68.

[0286] Synthesis Example 19: Preparation of Compound 413

[0287]

[0288] Following the same preparation method as in Synthesis Example 3, a-4, c-4, and d-4 were replaced with equimolar amounts of a-72, c-413, and d-137, respectively, to obtain compound 413 (22.10 g) with HPLC purity ≥ 99.97%. Mass spectrum m / z: 756.3241 (theoretical value: 756.3253). Theoretical element content (%): C 55 H 40 N4: C, 87.27; H, 5.33; N, 7.40. Measured element content (%): C, 87.29; H, 5.32; N, 7.39.

[0289] Synthesis Example 20: Preparation of Compound 414

[0290]

[0291] Following the same preparation method as in Synthesis Example 3, a-4, c-4, and d-4 were replaced with equimolar amounts of a-414, c-414, and d-72, respectively, to obtain compound 414 (18.80 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 643.2769 (theoretical value: 643.2784). Theoretical element content (%): C 46 H 25 D5N4: C, 85.82; H, 5.48; N, 8.70. Measured element content (%): C, 85.80; H, 5.50; N, 8.68.

[0292] Synthesis Example 21: Preparation of Compound 469

[0293]

[0294] Following the same preparation method as in Synthesis Example 3, a-4, c-4, and d-4 were replaced with equimolar amounts of a-414, c-414, and d-72, respectively, to obtain compound 414 (21.34 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 740.2957 (theoretical value: 740.2940). Theoretical element content (%): C 54 H 36 N4: C, 87.54; H, 4.90; N, 7.56. Measured element content (%): C, 87.52; H, 4.88; N, 7.60.

[0295] Synthesis Example 22: Preparation of Compound 479

[0296]

[0297] Following the same preparation method as in Synthesis Example 3, a-4, c-4, and d-4 were replaced with equimolar amounts of a-414, c-414, and d-72, respectively, to obtain compound 414 (21.34 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 740.2925 (theoretical value: 740.2940). Theoretical element content (%): C 54 H 36 N4: C, 87.54; H, 4.90; N, 7.56. Measured element content (%): C, 87.51; H, 4.89; N, 7.59.

[0298] Synthesis Example 23: Preparation of Compound 489

[0299]

[0300] Following the same preparation method as in Synthesis Example 3, a-4 was replaced with an equal molar amount of c-133 to obtain compound 489 (20.72 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 732.3236 (theoretical value: 732.3253). Theoretical element content (%) C 53 H 40 N4: C, 86.85; H, 5.50; N, 7.64. Measured element content (%): C, 86.88; H, 5.48; N, 7.63.

[0301] Synthesis Example 24: Preparation of Compound 498

[0302]

[0303] Following the same preparation method as in Synthesis Example 3, a-4 and d-4 were replaced with equimolar amounts of a-498 and d-498, respectively, to obtain compound 498 (20.82 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 722.2883 (theoretical value: 722.2866). Theoretical element content (%) C 50 H 38 N4Si: C, 83.07; H, 5.30; N, 7.75. Measured element content (%): C, 83.05; H, 5.28; N, 7.78.

[0304] Synthesis Example 25: Preparation of Compound 513

[0305]

[0306] Following the same preparation method as in Synthesis Example 3, compound 513 (23.63 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-513 and d-513, respectively. HPLC purity was ≥99.92%. Mass spectrum m / z: 831.2974 (theoretical value: 831.2998). Theoretical element content (%): C 59 H 37 N5O: C, 85.18; H, 4.48; N, 8.42. Measured element content (%): C, 85.20; H, 4.46; N, 8.39.

[0307] Synthesis Example 26: Preparation of Compound 521

[0308]

[0309] Following the same preparation method as in Synthesis Example 3, compound 521 (20.42 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-521 and d-521, respectively. HPLC purity was ≥99.98%. Mass spectrum m / z: 689.2561 (theoretical value: 689.2579). Theoretical element content (%): C 49 H 31 N5: C, 85.32; H, 4.53; N, 10.15. Measured element content (%): C, 85.30; H, 4.55; N, 10.16.

[0310] Synthesis Example 27: Preparation of Compound 568

[0311]

[0312] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-568 to obtain compound 568 (19.53 g) with HPLC purity ≥ 99.95%. Mass spectrum m / z: 668.2869 (theoretical value: 668.2878). Theoretical element content (%) C 48 H 28 D4N4: C, 86.20; H, 5.42; N, 8.38. Measured element content (%): C, 86.19; H, 5.40; N, 8.40.

[0313] Synthesis Example 28: Preparation of Compound 634

[0314]

[0315] Following the same preparation method as in Synthesis Example 3, compound 634 (23.05 g) was obtained by replacing c-4 and d-4 with equimolar amounts of c-634 and d-634, respectively. HPLC purity was ≥99.91%. Mass spectrum m / z: 822.3738 (theoretical value: 822.3722). Theoretical element content (%): C 60 H 46 N4: C, 87.56; H, 5.63; N, 6.81. Measured element content (%): C, 87.55; H, 5.61; N, 6.84.

[0316] Synthesis Example 29: Preparation of Compound 653

[0317]

[0318] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-653 to obtain compound 653 (21.92 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 782.3425 (theoretical value: 782.3409). Theoretical element content (%) C 57 H 42 N4: C, 87.44; H, 5.41; N, 7.16. Measured element content (%): C, 87.41; H, 5.43; N, 7.18.

[0319] Synthesis Example 30: Preparation of Compound 737

[0320]

[0321] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-769 to obtain compound 769 (24.05 g) with HPLC purity ≥ 99.92%. Mass spectrum m / z: 858.3735 (theoretical value: 858.3722). Theoretical element content (%) C 63 H 46 N4: C, 88.08; H, 5.40; N, 6.52. Measured element content (%): C, 88.10; H, 5.39; N, 6.51.

[0322] Synthesis Example 31: Preparation of Compound 771

[0323]

[0324] Following the same preparation method as in Synthesis Example 3, d-4 was replaced with an equal molar amount of d-309 to obtain compound 771 (22.04 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 790.3078 (theoretical value: 790.3096). Theoretical element content (%) C58 H 38 N4: C, 88.07; H, 4.84; N, 7.08. Measured element content (%): C, 88.04; H, 4.86; N, 7.09.

[0325] Device Examples

[0326] In the present invention, the ITO glass 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%.

[0327] 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 luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System. The test environment was atmospheric and room temperature.

[0328] The device is prepared using a vacuum evaporation system, which is completed by continuous evaporation under uninterrupted vacuum conditions. The materials used are placed in different evaporation source quartz crucibles, and the temperature of the evaporation source can be controlled individually. The thermal evaporation rate of organic materials is generally set at 0.1nm / s, and the evaporation rate of electrode metals is 0.4~0.6nm / s. The processed glass substrate is placed in the OLED vacuum coating machine. During the film production process, the system vacuum degree should be maintained at 5×10 -5 Pa, the organic layer and metal electrode are evaporated separately by replacing the mask plate, the evaporation speed is detected by Inficon's SQM160 quartz crystal film thickness detector, and the film thickness is detected by a quartz crystal oscillator.

[0329] Example 1: Preparation of organic electroluminescent device 1

[0330] ITO is used as an anode on a glass substrate; 20 nm of HT-1:HI-1 (mixed in a mass ratio of 97%:3%) is vacuum evaporated on the anode to form a hole injection layer; 110 nm of HT-1 is vacuum evaporated on the hole injection layer to form a hole transport layer; 10 nm of EB-1 is vacuum evaporated on the hole transport layer to form an electron blocking layer; 36 nm of BH-1:BD-1 (mixed in a mass ratio of 96%:4%) is vacuum evaporated on the electron blocking layer to form a light-emitting layer; 35 nm of the compound 4 of the present invention:Liq (mixed in a mass ratio of 1:1) is vacuum evaporated on the light-emitting layer to form an electron transport layer; 0.8 nm of LiF is vacuum evaporated on the electron transport layer to form an electron injection layer; and 120 nm of Al is vacuum evaporated on the electron injection layer to form a cathode.

[0331] Examples 2 to 30: Preparation of organic electroluminescent devices 2 to 30

[0332] The compound 4 in the first hole transport layer of Example 1 was replaced by compound 22, compound 72, compound 75, compound 86, compound 110, compound 137, compound 180, compound 181, compound 217, compound 342, compound 351, compound 368, compound 377, compound 378, compound 379, compound 413, compound 414, compound 469, compound 479, compound 489, compound 498, compound 513, compound 521, compound 568, compound 634, compound 653, compound 737, compound 769, and compound 771, respectively. The other steps were the same to obtain organic electroluminescent devices 2 to 30.

[0333] Comparative Examples 1 to 3: Preparation of Comparative Organic Electroluminescent Devices 1 to 3

[0334] Comparative organic electroluminescent devices 1 to 3 were obtained by replacing compound 4 in the electron transport layer of Example 1 with R-1, R-2, and R-3, respectively, and following the same other steps.

[0335]

[0336] 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 3 are shown in Table 1.

[0337] Table 1 Luminescence characteristics test data of organic electroluminescent devices

[0338]

[0339]

[0340] Note: T95 refers to the current density of 10mA / cm 2Under the condition of , the time taken for the device brightness to decay to 95%;

[0341] It can be seen from Table 1 that, compared with Comparative Examples 1 to 3, when the fluorene compound represented by Formula 1 of the present invention is used in the electron transport layer of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved.

[0342] Example 31: Preparation of organic electroluminescent device 31

[0343] ITO was used as an anode on a glass substrate; 50 nm of 2-TNATA was vacuum-deposited on the anode to form a hole injection layer; 120 nm of NPB was vacuum-deposited on the hole injection layer to form a hole transport layer; 30 nm of GH-1:GH-2:GD-1 (mixed in a mass ratio of 48%:48%:4%) was vacuum-deposited on the hole transport layer to form a light-emitting layer; 30 nm of compound 4 of the present invention was vacuum-deposited on the light-emitting layer to form a hole blocking layer; 32 nm of ET-1:Liq (mixed in a mass ratio of 1:1) was vacuum-deposited on the hole blocking layer to form an electron transport layer; 1.2 nm of LiF was vacuum-deposited on the electron transport layer to form an electron injection layer; and 120 nm of Al was vacuum-deposited on the electron injection layer to form a cathode.

[0344] Examples 32-60: Preparation of organic electroluminescent devices 32-60

[0345] The compound 4 in the hole blocking layer of Example 31 was replaced by compound 22, compound 72, compound 75, compound 86, compound 110, compound 137, compound 180, compound 181, compound 217, compound 342, compound 351, compound 368, compound 377, compound 378, compound 379, compound 413, compound 414, compound 469, compound 479, compound 489, compound 498, compound 513, compound 521, compound 568, compound 634, compound 653, compound 737, compound 769, and compound 771, respectively, and the other steps were the same to obtain organic electroluminescent devices 32 to 60.

[0346] Comparative Examples 4 to 6: Preparation of Comparative Organic Electroluminescent Devices 4 to 6

[0347] The compound 4 in the hole blocking layer of Example 31 was replaced by R-1, R-4, and R-5, respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4 to 6.

[0348]

[0349] 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 4 to 6 are shown in Table 2.

[0350] Table 2 Luminescence characteristics test data of organic electroluminescent devices

[0351]

[0352]

[0353] Note: T95 refers to the current density of 10mA / cm 2 Under the condition of , the time taken for the device brightness to decay to 95%;

[0354] From the results in Table 2, it can be seen that when the fluorene compounds of the present invention are used in organic electroluminescent devices as hole blocking layer materials, the performance of the devices is significantly improved compared with Comparative Examples 4 to 6, showing the advantages of high luminous efficiency and long service life.

[0355] Example 61: Preparation of organic electroluminescent device 61

[0356] On a glass substrate, ITO was used as an anode; 50 nm of 2-TNATA was vacuum-deposited on the anode to form a hole injection layer; 100 nm of NPB was vacuum-deposited on the hole injection layer to form a hole transport layer 1; 30 nm of BH-2:BD-2 (mixed in a mass ratio of 95%:5%) was vacuum-deposited on the hole transport layer 1 to form a light-emitting layer 1; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum-deposited on the light-emitting layer 1 to form an electron transport layer 1; 10 nm of the present invention compound 72:Li (mixed in a mass ratio of 97%:3%) was vacuum-deposited on the electron transport layer 1 to form an n-type charge generation layer; 10 nm of the compound NPB:HAT-CN of the present invention (mixed in a mass ratio of 90%:10%) was vacuum evaporated to form a p-type charge generation layer; 100 nm of HT-1 was vacuum evaporated on the p-type charge generation layer to form a hole transport layer 2; 30 nm of BH-2:BD-2 (mixed in a mass ratio of 95%:5%) was vacuum evaporated on the hole transport layer 2 to form a light-emitting layer 2; 28 nm of ET-2:LiQ (mixed in a mass ratio of 1:1) was vacuum evaporated on the light-emitting layer 2 to form an electron transport layer 2; 1.0 nm of LiF was vacuum evaporated on the electron transport layer 2 to form an electron injection layer; and 120 nm of Al was vacuum evaporated on the electron injection layer to form a cathode.

[0357]

[0358] Examples 62-80: Preparation of organic electroluminescent devices 62-80

[0359] The compound 72 in the n-type charge generation layer of Example 61 was replaced with compound 75, compound 86, compound 110, compound 137, compound 180, compound 181, compound 342, compound 351, compound 368, compound 377, compound 378, compound 379, compound 413, compound 414, compound 469, compound 521, compound 568, compound 653, and compound 737, respectively. The other steps were the same to obtain organic electroluminescent devices 62 to 80.

[0360] Comparative Examples 7-8: Preparation of Comparative Organic Electroluminescent Devices 7-8

[0361] Comparative organic electroluminescent devices 7 to 8 were obtained by replacing compound 4 in the n-type charge generation layer of Example 61 with Bphen and R-6, respectively, and following the same other steps.

[0362] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 61 to 80 of the present invention and Comparative Examples 7 to 8 are shown in Table 3.

[0363] Table 3 Luminescence characteristics test data of organic electroluminescent devices

[0364]

[0365]

[0366] Note: T95 refers to the current density of 10mA / cm 2 Under the condition of , the time taken for the device brightness to decay to 95%;

[0367] The results in Table 3 show that when the fluorene compounds of the present invention are used as n-type charge generation layer materials in organic electroluminescent devices, the luminous efficiency and service life of the organic electroluminescent devices are improved compared with those in Comparative Examples 7 to 8, and the fluorene compounds of the present invention are n-type charge generation layer materials for organic electroluminescent devices with good performance.

[0368] 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: Having the general formula shown in structural formula 1, Wherein, Ar1 is selected from any one of a C3-C15 alicyclic group substituted or unsubstituted by R1, a fused ring group of a C3-C15 alicyclic ring and a C6-C30 aromatic ring substituted or unsubstituted by R1, a C6-C30 aryl group substituted or unsubstituted by R1, a C2-C30 heteroaryl group substituted or unsubstituted by R1, and a C1-C25 heterocycloalkyl group substituted or unsubstituted by R1; The R1 is selected from any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, and at least one R1 is selected from cyano; Ar2 is selected from any one of a substituted or unsubstituted C3-C15 alicyclic group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a substituted or unsubstituted C2-C25 heterocycloalkyl group; The x are identically or differently selected from C(R2) or N atoms, the x at the bonding site is selected from C, and at least one x is selected from N atoms; R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group; The R a Any one selected from the following groups or their combinations: The v is selected from C (R3) or N atoms, the v at the bonding site is selected from C; Said Y1 is selected from an O atom, a S atom or N(R4); Said Y2 is selected from O atom, S atom, N(R5) or C(R6 R7); The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, and at least one R3 is selected from any one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C9 alicyclic group; R4 and R5 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group; R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or R6 and R7 are connected to form a substituted or unsubstituted ring; The R b Any one selected from substituted or unsubstituted C1-C15 alkyl or the following groups or combinations thereof, The z are selected from C(R8) or N atoms, the z at the bonding site is selected from C; The ring B is selected from a substituted or unsubstituted C3-C15 alicyclic group; Said Y3 is selected from O atom, S atom or N(R 11 ); Said Y4 is selected from C(R 12 ) or N atom, Y4 at the bonding site is selected from C; The R8, R 12 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R8 are connected to each other to form a substituted or unsubstituted ring; The R9, R 10 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R9 and R 10 Connected to each other to form a substituted or unsubstituted ring; The R 11 Any one selected from hydrogen, deuterium, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C15 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group; The R b It can be a single bond to L0; The R c 、R d independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, or the two adjacent R c , two R d are connected to each other to form a substituted or unsubstituted ring; said n1 is independently selected from 0, 1, 2, 3 or 4; The L0, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C15 alicyclic group and C6-C30 aromatic ring condensed group, or any combination thereof.

2. The fluorene compound according to claim 1, characterized in that In the formula 1 Any one selected from the following groups: The R b any one selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and silyl; Said R3 is the same or different and is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, furanyl, thiophenyl, phenyl Any one or more of oxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted by multiple substituents, the multiple substituents are the same or different, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, and at least one R3 is selected from the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, and triphenylsilyl; The R8, R 12 any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, wherein when substituted by multiple substituents, the multiple substituents are the same or different, or two adjacent R8 are connected to form a substituted or unsubstituted ring; The R c 、R d R is selected from any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl. In the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R c Between the two R d They are connected to each other to form a substituted or unsubstituted ring; The n1 is independently selected from 0, 1, 2, 3 or 4; the n2 is independently selected from 0, 1, 2 or 3; a1 is independently selected from 1, 2, 3, 4, or 5; a2 is independently selected from 1, 2, 3, 4, 5, 6, or 7; a3 is independently selected from 1, 2, 3, or 4; a4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; a5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a6 is independently selected from 1, 2, or 3; a7 is independently selected from 1 or 2; a8 is independently selected from 1, 2, 3, 4, 5, or 6; a9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; Said b1 is independently selected from 1, 2, 3, 4 or 5; said b2 is independently selected from 1, 2, 3, 4, 5, 6 or 7; said b3 is independently selected from 1, 2, 3 or 4; said b4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; said b7 is independently selected from 1, 2 or 3; said b8 is independently selected from 1 or 2; said b9 is independently selected from 1, 2, 3, 4, 5 or 6.

3. The fluorene compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups or combinations thereof: The t is selected from C (R1) or N atoms, the t at the bonding site is selected from C; The T1 is selected from O atom, S atom or N(R 14 ); The T2 is selected from O atoms, S atoms, N (R 15 ) or C(R 16 R 17 ); The ring Q is selected from a substituted or unsubstituted C3-C15 alicyclic group; Said R1 is independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, Any one or more of triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted with multiple substituents, the multiple substituents are the same or different, or the two adjacent R1s are connected to form a substituted or unsubstituted ring, and at least one R1 is selected from cyano; The R 14 、R 15 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; said R 15 It may be a single bond to L1; The R 16 、R 17 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; or said R 16 and R 17 They are connected to each other to form a substituted or unsubstituted ring.

4. The fluorene compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups or combinations thereof: Said R1 is the same or different and is selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl any one or more, In the case of being substituted by multiple substituents, the multiple substituents are the same or different, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring, and at least one R1 is selected from cyano, wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, deuterated methyl, deuterated tert-butyl, deuterated isopropyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, and quinoxalinyl; The R 14 、R 15 、R 16 、R 17 any one or more of hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other, or said R 16 and R 17 are connected to each other to form a substituted or unsubstituted ring; The R f any one or more of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same or different; Said c1 is independently selected from 1, 2, 3, 4 or 5; said c2 is independently selected from 1, 2, 3 or 4; said c3 is independently selected from 1 or 2; said c4 is independently selected from 1, 2 or 3; said c5 is independently selected from 1, 2, 3, 4, 5, 6 or 7; said c6 is independently selected from 1, 2, 3, 4, 5 or 6; said c7 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said c8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

5. The fluorene compound according to claim 1, characterized in that The Ar2 is selected from any one of the following groups or combinations thereof: The p is the same or different and is selected from C(R 18 ) or a N atom, and p at the bonding site is selected from C; The Q1 is selected from O atom, S atom or N(R 19 ); The Q2 is independently selected from O atoms, S atoms, N (R 20 ) or C(R 21 R 22 ); The ring E is selected from a substituted or unsubstituted C3-C15 alicyclic group; The R 18 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R 18 are connected to each other to form a substituted or unsubstituted ring; The R 19 、R 20 、R 21 、R 22 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or the adjacent R 21 and R 22 They are connected to each other to form a substituted or unsubstituted ring.

6. The fluorene compound according to claim 1, characterized in that The L0, L1, and L2 are independently selected from a single bond, the following groups, or any combination thereof: The r are identical or different selected from C(R 23 ) or a N atom, and r at the bonding site is selected from C; Said E1 is selected from O atom, S atom, N(R 24 ) or C(R 25 R 26 ); Said E2 is selected from O atom, S atom or N(R 27 ); The ring G is selected from substituted or unsubstituted C3-C15 alicyclic groups; The R 23 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R 23 are connected to each other to form a substituted or unsubstituted ring; The R 24 、R 25 、R 26 、R 27 independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or said R 25 and R 26 They are connected to each other to form a substituted or unsubstituted ring.

7. The fluorene compound according to claim 1, characterized in that The fluorene compound represented by Formula 1 is selected from any one of the following chemical structures:

8. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more of the anode and the cathode, wherein: The organic layer contains the fluorene compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode, and includes at least one layer of a hole transport region, a light-emitting layer, and an electron transport region. At least one layer of the electron transport region or the light-emitting layer contains the fluorene compound according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region or a covering layer, and an n-type charge generation layer and a p-type charge generation layer are arranged in the middle of each light-emitting layer. The n-type charge generation layer contains the fluorene compound according to any one of claims 1 to 7.

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