Fluorene-containing amine compound and organic electroluminescent device thereof

Abstract

The invention provides a fluorene-containing amine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The fluorene-containing amine compound disclosed by the invention has relatively high hole transport capacity and proper HOMO energy level, and when the fluorene-containing amine compound is applied to a hole transport layer or an electron blocking layer of an organic electroluminescent device, the luminous efficiency of the device is effectively improved, and the service life of the device is effectively prolonged; the fluorene-containing amine compound provided by the invention has a relatively high refractive index, and when the fluorene-containing amine compound is applied to a covering layer of the organic electroluminescent device, the luminous efficiency is effectively improved, so that the luminous efficiency of the organic electroluminescent device is further improved, and the service life of the organic electroluminescent device is further prolonged. In conclusion, the fluorene-containing amine compound provided by the invention can be widely applied to the fields of panel display, illumination light sources and the like, and has a good application prospect.

Description

Technical Field

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

[0002] Organic Light-Emitting Diode (OLED) technology is known as a flat display technology with fantastic display characteristics. Because its light-emitting mechanism is similar to that of light-emitting diodes (LEDs), it is also called organic light-emitting diodes. Compared with traditional liquid crystal displays, this new display technology has the advantages of being thinner and lighter, actively emitting light, having a wide viewing angle, high definition, fast response, low energy consumption, low temperature, excellent shock resistance, potentially low manufacturing costs, flexibility and environmentally friendly design. It is recognized by the industry as the most ideal and promising next-generation display technology.

[0003] OLED is a current-type semiconductor light-emitting device based on organic materials. Its typical structure is to make a layer of organic light-emitting material on ITO glass as the light-emitting layer, and there is a metal electrode with low work function above the light-emitting layer. When a voltage is applied to the electrode, the light-emitting layer generates light radiation. The electroluminescence of organic materials belongs to injection-type compound luminescence. Its luminescence mechanism is that the holes and electrons generated by the positive and negative electrodes are compounded into excitons in the light-emitting material, and the energy of the excitons is transferred to the light-emitting molecules, so that the electrons in the light-emitting molecules are excited to the excited state, which is an unstable state. The de-excitation process produces visible light. In order to enhance the injection and transmission capabilities of electrons and holes, a hole transport layer and an electron blocking layer are usually added between ITO and the light-emitting layer, or / and an electron transport layer and a hole blocking layer are added between the light-emitting layer and the metal electrode to improve the luminescence efficiency. In addition, a covering layer can be added on the outside of the organic electroluminescent device, which can effectively avoid the total reflection of light inside the device, improve the light extraction efficiency of the device, and thus improve the luminescence efficiency of the device. In order to further improve the luminous efficiency of the device, two or more independent light-emitting units are connected in series through a charge generation layer (CGL) to develop a higher-performance stacked OLED. The electrons and holes generated by the CGL are injected into adjacent light-emitting units respectively, and recombine into excitons in the light-emitting units to emit light. In addition, n-type doped layers / p-type doped layers are often used as connecting layers between light-emitting units.

[0004] However, due to the incomplete development of organic light-emitting materials at this stage, there are still many problems with organic electroluminescent devices. For example, the hole mobility of the hole transport material is low, which will lead to charge imbalance in the light-emitting layer; the refractive index and glass transition temperature of the cover layer material are low, which affects the luminous efficiency; the energy level of the electron blocking layer and the adjacent light-emitting layer does not match, and the charge generation efficiency of the p-type charge generation layer material is low. These factors restrict the development of OLED devices. Therefore, it is necessary to further develop higher-performance hole transport materials, electron blocking materials, cover layer materials, and p-type charge generation layer materials to improve the luminous efficiency and service life of organic electroluminescent devices. Summary of the invention

[0005] The object of the present invention is to provide an amine compound containing fluorene and an organic electroluminescent device thereof. When the amine compound containing fluorene provided by the present invention is applied to the hole transport region, p-type charge generation layer or covering layer of the organic electroluminescent device, an organic electroluminescent device with high efficiency and long life can be developed, thereby solving the problems of low luminous efficiency and short service life of the organic electroluminescent device in the prior art.

[0006] Specifically, the present invention provides a fluorene-containing amine compound having the general formula shown in Structural Formula 1,

[0007]

[0008] Wherein, the Ar 1 is selected from the group shown in Formula 2; 2 A group selected from the group shown in Formula 3;

[0009] The ring A is selected from a substituted or unsubstituted C3-C8 monocyclic alicyclic group;

[0010] The R 1 , R 2 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R 1 Between the two R 2 are connected to each other to form a substituted or unsubstituted ring; said a is selected from 1, 2, 3 or 4; said b is selected from 1, 2 or 3;

[0011] The R 3Any one selected from 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, and a substituted or unsubstituted C2-C30 heteroaryl group;

[0012] The R 4 Any one selected from a substituted or unsubstituted C6-C30 aromatic group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted C2-C30 heteroaromatic group;

[0013] The R 5 , R 6 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R 5 Between the two R 6 are connected to each other to form a substituted or unsubstituted ring; said c is selected from 1, 2, 3 or 4; said d is selected from 1, 2, 3 or 4;

[0014] The X is selected from O, S or N (R 8 );

[0015] The R 8 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, 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;

[0016] The ring B is selected from any one of a C6-C30 aryl group substituted or unsubstituted by a deuterium atom, and a C2-C30 heteroaryl group substituted or unsubstituted by a deuterium atom;

[0017] The R 7 are selected from hydrogen or deuterium, the same or different; said e is selected from 1 or 2;

[0018] The L 1 , L 2 , L 3Any one independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring condensed group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0019] 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-containing amine compound of the present invention.

[0020] Beneficial effects:

[0021] The fluorene-containing amine compound of the present invention has a high hole transport ability and a suitable HOMO energy level. When the fluorene-containing amine compound is applied to the hole transport layer or the electron blocking layer of the organic electroluminescent device, the luminous efficiency and the service life of the device are effectively improved; and the fluorene-containing amine compound of the present invention has a high refractive index. When applied to the covering layer of the organic electroluminescent device, the light extraction efficiency is effectively improved, so that the luminous efficiency and the service life of the organic electroluminescent device are further improved. DETAILED DESCRIPTION

[0022] The present invention is further explained below in conjunction with specific embodiments. It should be understood that these embodiments 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, various equivalent forms of modifications to the present invention by those skilled in the art all fall within the scope of protection required by this application.

[0023] In the compounds of the present invention, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain about 0.0156 atomic % deuterium per hydrogen atom.

[0024] In the present invention, the use of "H" and "hydrogen" means that the hydrogen atoms in the chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95 atomic % of which is deuterium. "T" and "tritium" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95% of which is tritium. In the present invention, the omitted hydrogen represents "H" or "hydrogen".

[0025] Examples of the halogen according to the present invention may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0026] The "C1-C15" in the "substituted or unsubstituted C1-C15 alkyl" of the present invention refers to the number of carbon atoms in the unsubstituted "alkyl", excluding the number of carbon atoms in the substituent. The "C6-C30" in the "substituted or unsubstituted C6-C30 aryl" refers to the number of carbon atoms in the unsubstituted "aryl", excluding the number of carbon atoms in the substituent. And so on.

[0027] The alkyl group described in the present invention refers to a monovalent group formed by missing a hydrogen atom from an alkane molecule. The number of carbon atoms of the alkyl group is C1 to C15, preferably C1 to C10. Examples of the alkyl group include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0028] The chain alkyl group with more than three carbon atoms described in the present invention includes its isomers, for example, propyl group includes n-propyl group and isopropyl group, butyl group includes n-butyl group, sec-butyl group, isobutyl group and tert-butyl group, and so on.

[0029] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k ) 3 A group in which 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, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring. Preferably, 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 C3-C30 cycloalkyl. The number of carbon atoms in 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 in 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 in 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 kThe 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" refers to silyl (-SiH 3 ) at least one substituent R k is an alkyl group, and preferred alkylsilyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the “arylsilyl group” is a silyl group (-SiH 3 ) at least one substituent R k is an aryl group, and preferred arylsilyl groups specifically include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and the like, but are not limited thereto.

[0030] 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 a monocyclic aryl group, a polycyclic aryl group, and a condensed ring aryl group. The number of carbon atoms of the aryl group is C6 to C30, preferably C6 to C20, further preferably C6 to C15, and further preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups, phenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, naphthyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, phenanthryl, triphenylene, anthracenyl, pyrenyl, fluorenyl, spirobifluorenyl, spiroanthracenyl, benzofluorenyl, benzospirobifluorenyl, etc.

[0031] The alicyclic group described in the present invention refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which may be completely unsaturated or partially unsaturated. For example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but not limited thereto. Multiple monocyclic hydrocarbons can also be connected in a variety of ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure, such as adamantane, norbornane, camphane, etc., but not limited thereto.

[0032] The fused ring group of an alicyclic ring and an aromatic ring of the present invention refers to a general term for a monovalent group after an alicyclic ring and an aromatic ring are fused together and a hydrogen atom is removed. Examples of the fused ring group of an alicyclic ring and an aromatic ring may include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3 to C15, preferably C3 to C10. The carbon number of the aromatic ring is C6 to C30, preferably C6 to C18, and more preferably C6 to C12.

[0033] 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 of 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, pyrenyl, indenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, etc.

[0034] The sub-fused ring group of the alicyclic ring and the aromatic ring described in the present invention refers to the general term for the divalent group left after the alicyclic ring and the aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-fused ring of the alicyclic ring and the aromatic ring may include indenylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropanediylene, benzocyclobutanediylene, benzocyclobutenylene, naphthocyclopentanediylene, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3 to C15, preferably C3 to C10. The carbon number of the aromatic ring is C6 to C30, preferably C6 to C18.

[0035] 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 of the heteroarylene group is C2 to C30, preferably C2 to C20, and preferably C2 to C10. The heteroatoms include, but are not limited to, the atoms shown below, 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 groups described below, pyridylene, pyrimidylene, quinolylene, isoquinolylene, furylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thienylene, benzothienylene, dibenzothienylene, benzodibenzothienylene, etc.

[0036] The term "substituted or unsubstituted" as used herein means not substituted or substituted by one or more substituents selected from the group consisting of 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, or 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-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, or a substituted or unsubstituted silyl group. C12 cycloalkyl, 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 cyclopropane butanyl, 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, cycloheptanyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornanyl, methyl-substituted norbornanyl, ethyl-substituted norbornanyl, deuterated norbornanyl, tetrahydropyrrole The invention also includes but is not limited to: 1,2-dimethyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1

[0037] In this specification, when a substituent or a bond at 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 ring. For example, Can be expressed Can be expressed And so on.

[0038] 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.

[0039] For example, Can be expressed Can be expressed Can be expressed And so on.

[0040] 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:

[0041]

[0042] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0043] The present invention provides a fluorene-containing amine compound having the general formula shown in Structural Formula 1:

[0044]

[0045] Wherein, the Ar 1 is selected from the group shown in Formula 2; 2 A group selected from the group shown in Formula 3;

[0046] The ring A is selected from a substituted or unsubstituted C3-C8 monocyclic alicyclic group;

[0047] The R 1 , R 2 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R 1 Between the two R 2 are connected to each other to form a substituted or unsubstituted ring; said a is selected from 1, 2, 3 or 4; said b is selected from 1, 2 or 3;

[0048] The R 3 Any one selected from 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, and a substituted or unsubstituted C2-C30 heteroaryl group;

[0049] The R 4 Any one selected from a substituted or unsubstituted C6-C30 aromatic group, a fused ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted C2-C30 heteroaromatic group;

[0050] The R 5 , R 6 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R 5 Between the two R 6 are connected to each other to form a substituted or unsubstituted ring; said c is selected from 1, 2, 3 or 4; said d is selected from 1, 2, 3 or 4;

[0051] The X is selected from O, S or N (R 8 );

[0052] The R8 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, 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;

[0053] The ring B is selected from any one of a C6-C30 aryl group substituted or unsubstituted by a deuterium atom, and a C2-C30 heteroaryl group substituted or unsubstituted by a deuterium atom;

[0054] The R 7 are selected from hydrogen or deuterium, the same or different; said e is selected from 1 or 2;

[0055] The L 1 , L 2 , L 3 Any one independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring condensed group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0056] Preferably, the ring A is selected from any one of the following groups:

[0057]

[0058] The R 9 The same or different ones are any one selected from hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, 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;

[0059] The f 1 Independently selected from 1, 2, 3 or 4; said f 2 Independently selected from 1, 2, 3, 4, 5 or 6; said f 3 Independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said f 4 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said f 5 independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; when there are two or more R 9 When two or more R 9The same or different from each other.

[0060] Preferably, the R 9 the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted 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, dihydro Any one of naphthyl, anthracenyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl and silyl, when substituted with multiple substituents, the multiple substituents are the same or different from each other.

[0061] Preferably, the formula 2 is selected from any one of the following groups:

[0062]

[0063] The R 5 , R 6 independently selected from hydrogen, deuterium, cyano, halogen, nitro, 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, 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, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl, when substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R 5 Between the two R 6 are connected to each other to form a substituted or unsubstituted ring; said c is selected from 1, 2, 3 or 4; said d is selected from 1, 2, 3 or 4;

[0064] The R aThe same or different R 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 C2-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; in the case of being substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R a are connected to each other to form a substituted or unsubstituted ring;

[0065] The R b 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, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, silyl, in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other;

[0066] The g 1 Independently selected from 1, 2, 3, 4 or 5; said g 2 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said g 3 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said g 4 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; 5 Independently selected from 1, 2, 3 or 4; said g 6 Independently selected from 1, 2, 3, 4, 5, 6 or 7; said g 7 Independently selected from 1, 2 or 3; said g 8 Independently selected from 1, 2, 3, 4, 5 or 6; said g 9 Independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said g 10 Independently selected from 1 or 2; said g 11 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0067] Preferably, the R aat least one of deuterium, cyano, halogen, nitro, substituted or unsubstituted 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, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, silyl, in the case of being substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R a They are connected to each other to form a substituted or unsubstituted ring.

[0068] Preferably, the formula 3 is selected from any one of the following groups:

[0069]

[0070]

[0071] The X is selected from O, S or N (R 8 );

[0072] The R 7 are identically or differently selected from hydrogen or deuterium; said e is independently selected from 1 or 2;

[0073] The R c are identically or differently selected from hydrogen or deuterium; said h 1 Independently selected from 1, 2 or 3; said h 2 Independently selected from 1, 2, 3, 4 or 5; said h 3 Independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said h 4 Independently selected from 1 or 2; said h 5 Independently selected from 1, 2, 3 or 4; said h 6 Independently selected from 1, 2, 3, 4, 5 or 6;

[0074] The R 8selected from the group consisting of hydrogen, deuterium, 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, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydro Any one of naphthyl, dihydronaphthyl, anthracenyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl and silyl.

[0075] Preferably, the L 1 , L 2 , L 3 Independently selected from a single bond or any one of the following groups or combinations thereof:

[0076]

[0077] The z are selected from CH or N atoms the same or differently; the z at the bonding site is selected from C;

[0078] The R 11 The same or different groups are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 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;

[0079] The Y 1 independently selected from O atoms, S atoms, C(R f R g ) or N(R d );

[0080] The Y 2 independently selected from an O atom, a S atom or a N(R h );

[0081] The ring D is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0082] The R f , R gis independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, or the R f and R g are connected to each other to form a substituted or unsubstituted ring;

[0083] The R d , R h Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group;

[0084] The 1 Independently selected from 1, 2, 3 or 4; said j 2 Independently selected from 1, 2 or 3; said j 3 Independently selected from 1 or 2.

[0085] More preferably, the L 1 , L 2 , L 3 Independently selected from a single bond or any one of the following groups or combinations thereof:

[0086]

[0087] The R 11 , R 12 R is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, 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 3 are connected to each other to form a substituted or unsubstituted ring;

[0088] The R d , R hindependently 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, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, silyl or any combination thereof;

[0089] The 1 Selected from 1, 2, 3 or 4; said j 2 Selected from 1, 2 or 3; 3 Selected from 1 or 2; said j 4 Selected from 1, 2, 3, 4 or 5; 5 Selected from 1, 2, 3, 4, 5 or 6; 6 Selected from 1, 2, 3, 4, 5, 6, 7 or 8.

[0090] Further preferably, the L 1 , L 2 , L 3 Independently selected from a single bond or any one of the following groups or combinations thereof:

[0091]

[0092]

[0093] Most preferably, the fluorene-containing amine compound represented by Formula 1 is selected from any one of the chemical structures shown below:

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] Some specific chemical structures of the fluorene-containing amine compounds of structural formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all fluorene-containing amine compounds based on structural formula 1 and having substituents as defined above should be included.

[0113] 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-containing amine compound represented by Formula 1 of the present invention.

[0114] 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, an n-type charge generation layer, a p-type charge generation layer, and an electron transport region, and at least one layer of the hole transport region or the p-type charge generation layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0115] Preferably, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, the hole injection layer is located between the anode and the cathode, the hole transport layer is located between the hole injection layer and the cathode, the electron blocking layer is located between the hole transport layer and the cathode, and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0116] Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer comprises the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0117] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0118] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the second hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0119] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer and the second hole transport layer contain the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0120] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer and the third hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0121] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the first hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0122] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the second hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0123] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the third hole transport layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0124] Preferably, the thickness of the hole transport layer is 30 nm to 200 nm.

[0125] Preferably, the thickness of the first hole transport layer is 30 nm to 200 nm, and the thickness of the second hole transport layer is 3 nm to 100 nm.

[0126] Preferably, the thickness of the first hole transport layer is 60 nm to 180 nm.

[0127] Further preferably, the thickness of the first hole transport layer is 80 nm to 140 nm.

[0128] More preferably, the thickness of the first hole transport layer is 100 nm to 120 nm.

[0129] Preferably, the second hole transport layer has a thickness of 5 nm to 90 nm.

[0130] Further preferably, the thickness of the second hole transport layer is 40nm to 80nm (red light); the thickness of the second hole transport layer is 20nm to 60nm (green light); and the thickness of the second hole transport layer is 5nm to 30nm (blue light).

[0131] More preferably, the thickness of the second hole transport layer is 50nm to 70nm (red light); the thickness of the second hole transport layer is 30nm to 50nm (green light); the thickness of the second hole transport layer is 5nm to 25nm (blue light).

[0132] Preferably, the thickness of the third hole transport layer is 5 nm to 150 nm.

[0133] More preferably, the thickness of the third hole transport layer is 10 nm to 100 nm.

[0134] 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.

[0135] 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.

[0136] 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, and an n-type charge generation layer and a p-type charge generation layer are included between adjacent light-emitting units.

[0137] Preferably, the organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region and 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 p-type charge generation layer contains the fluorene-containing amine compound shown in Formula 1 of the present invention.

[0138] Preferably, the p-type charge generation layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention, or the p-type charge generation layer can be formed by doping the fluorene-containing amine compound of the present invention with other materials.

[0139] Preferably, the organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a covering layer, wherein the covering layer is located on the side of the cathode away from the anode, and the covering layer contains the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0140] The organic electroluminescent device of the present invention is usually formed on a substrate. The substrate may be any substrate that does not change when forming the electrode or the organic layer, for example, a substrate of glass, quartz, plastic, polymer film, silicon, etc. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.

[0141] The present invention has no particular limitation on 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 introduced respectively as follows:

[0142] The anode of the present invention preferably uses a metal, alloy, conductive compound, and mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide, indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (such as titanium nitride) can be cited, but are not limited to these.

[0143] 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, formed between the anode and the light-emitting layer, or formed between the hole transport layer and the anode. Materials such as polycyano conjugated organics, radialene compounds, phthalocyanine metal complexes, fluorene-containing amine compounds, polymers, etc. Specifically, for example, metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, and conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto, and may also include other compounds capable of p-doping.

[0144] 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 holes to the light-emitting layer, and has a material with high hole mobility and a material with good stability. The hole transport material of the present invention is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of the hole injection layer, and can be a single layer structure or a multilayer structure. The compound of the present invention can be used for the hole transport layer alone or in combination with the following compounds. As the hole transport layer material, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc. can be used. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro- 9,9'-bis(9-carbazolyl)-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (t-BuDNA), 9,10-di(2-naphthyl)anthracene (DNA), 9,10-diphenylanthracene (DPAnth), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), fluorene-containing amine compounds represented by Formula 1 of the present invention, etc., but are not limited thereto. Preferably, the fluorene-containing amine compounds represented by Formula 1 of the present invention are used.

[0145] The triplet state (T1) energy level of the preferred material of the electron blocking layer described in the present invention is higher than the T1 energy level of the main material in the light-emitting layer, which can play a role in blocking the energy loss of the light-emitting layer material; the HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the main material of the light-emitting layer, which is conducive to the injection of holes from the positive electrode into the light-emitting layer, and at the same time, the electron blocking layer material is required to have a high hole mobility, which is conducive to hole transport and reduces the application power of the device; the LUMO energy level of the electron blocking layer material is higher than the LUMO energy level of the main material of the light-emitting layer, which plays a role in electron blocking, that is, the electron blocking layer material is required to have a wide bandgap width (Eg). The electron blocking layer material that meets the above conditions can be a triarylamine derivative, a fluorene derivative, a spirofluorene derivative, a dibenzofuran derivative, a carbazole derivative, etc. For example, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine; dibenzofuran derivatives, such as N, N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, the fluorene-containing amine compound shown in Formula 1 of the present invention, etc., but are not limited thereto. The fluorene-containing amine compound shown in Formula 1 of the present invention is preferred.

[0146] The light-emitting layer of the present invention may contain only the guest material, or may be in the form of the guest material dispersed in the host material, wherein the host material may be composed of one or more materials.

[0147] As the main 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 (TPB 3), 1,3,5-tri(carbazole-9-yl)benzene (TCP), 14,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole azole (DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (BSPB), etc., but are not limited to these.

[0148] As the guest material of the light-emitting layer of the present invention, aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., for example, 4,4'-bis(4-(9H-carbazole-9-yl)phenylvinyl)biphenyl (BSB 4 ), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF 3 )、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)(acetylacetonate)iridium(III)(Ir(npy) 2 acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy) 3 ), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)picolinate (FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)picolinate (Ir(CF3ppy) 2 (pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) acetylacetonate (FIracac), etc., but not limited thereto.

[0149] 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-tri(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-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc., but are not limited thereto.

[0150] The electron transport layer material of the present invention preferably has a material with good electron transport ability and good stability. It can be a single-layer structure or a multilayer structure. The materials described below include 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- pyridinyl)phenyl] (TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene, 2-(3-(phenanthrene-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-hydroxyquinolinato)(4-phenylphenol)aluminum(III) (BAlq), 8-hydroxyquinolinate lithium (LiQ), tris(8-hydroxyquinolinato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinolinato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), etc., but are not limited to these.

[0151] The electron injection layer material of the present invention is preferably a material that can reduce 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. In addition, a variety of these compounds can also be used in combination.

[0152] The cathode of the present invention preferably uses metals, alloys, conductive compounds and mixtures thereof with a small work function (specifically, a work function of 3.8 eV or less). The materials used for the cathode of the present invention may include: metals or their alloys, multilayer structure materials, etc., for example, silver (Ag), aluminum (Al), magnesium (Mg), tin (Sb), magnesium silver (Mg:Ag), calcium / magnesium (Ca / Mg), etc., but are not limited thereto.

[0153] The anode and cathode of the present invention can be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the anode and cathode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0154] The cover 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 cover 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 compound, heteroaromatic compound, aromatic amine compound, etc. Specific examples may include LiF, CsF, MgF 2 , CaF 2 、CsCl、CuI、V 2 O 5 , WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 , tris(8-hydroxyquinoline)aluminum(III) (Alq 3 ), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), fluorene-containing amine compounds represented by Formula 1 of the present invention, etc., but are not limited thereto. Preferably, the fluorene-containing amine compounds represented by Formula 1 of the present invention are used.

[0155] The n-type charge generation material of the present invention can be selected from the following materials or one of their combinations: tris-(8-hydroxyquinolinate)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, quinoline lithium (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-phenolate)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]-alternate-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), etc., but are not limited thereto. In addition, auxiliary N-type charge generation materials 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.

[0156] 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-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, the fluorene-containing amine compound represented by Formula 1 of the present invention, etc., but not limited thereto, preferably the fluorene-containing amine compound represented by Formula 1 of the present invention.

[0157] There is no particular restriction on the preparation method of each thin film in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. can be used, but are not limited thereto. There is no particular restriction on the film thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated. On the contrary, if it is too thick, a high driving voltage is required and the efficiency is deteriorated. Therefore, it is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[0158] 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, televisions, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable devices, lighting equipment, etc.

[0159] Synthesis Example

[0160] Raw materials and reagents: The present invention has no particular restrictions on the raw materials or reagents used in the following synthetic examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0161] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0162] There is no particular limitation on the preparation method of the fluorene-containing amine compound of structural formula 1 of the present invention, and conventional methods known to those skilled in the art can be used, such as carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the fluorene-containing amine compound of structural formula 1 of the present invention can be prepared by the synthetic route shown below.

[0163] Intermediate preparation route:

[0164]

[0165] Compound synthesis route 1:

[0166]

[0167] Compound Synthesis Route 2:

[0168]

[0169] Compound synthesis route 3:

[0170]

[0171] The X 1 , X 2 , X 3 is a halogen atom, for example, which may be the same or different and is selected from the halogen atoms described below, I, Br, Cl.

[0172] Synthesis Example 1: Preparation of Intermediate C-404

[0173]

[0174] Under nitrogen protection, raw material c-321 (9.80 g, 46.00 mmol), raw material n-404 (7.19 g, 46.00 mmol), tetrakistriphenylphosphine palladium (0.64 g, 0.55 mmol), potassium carbonate (12.72 g, 92.00 mmol) and 250 mL toluene, 125 mL ethanol, 125 mL water were added to the reaction bottle, the mixture was stirred, heated under reflux for 4.5 hours, after the reaction was completed, the reaction solution was cooled to room temperature, the filter cake was filtered, and the filter cake was rinsed with ethanol, and the filter cake was recrystallized with toluene to obtain intermediate C-404 (8.78 g, yield 78%); HPLC purity ≥99.88%. Mass spectrum m / z: 244.0125 (theoretical value: 244.0113).

[0175] According to the above synthesis method, other intermediates required for the present invention are synthesized, and the relevant raw materials are shown in Table 101:

[0176] Table 101:

[0177]

[0178] Synthesis Example 2: Preparation of Compound 9

[0179]

[0180] Preparation of intermediate I-9:

[0181] Under nitrogen protection, raw material a-9 (13.71 g, 55.00 mmol), raw material b-9 (21.85 g, 55.00 mmol), Pd(OAc) were added to the reaction bottle. 2 (0.12 g, 0.55 mmol), P(t-Bu) 3 (1.10mL, 0.55mmol, 0.5M in toluene solution), NaOt-Bu (10.57g, 110.00mmol) and 300mL toluene solvent, stir the mixture, and heat the mixed solution of the above reactants under reflux for 5.5h. After the reaction is completed, cool to room temperature, add distilled water, extract with dichloromethane, stand and separate, collect the organic layer, dry it with anhydrous magnesium sulfate, filter, concentrate the filtrate by vacuum distillation, cool and crystallize, filter, and recrystallize the obtained solid with toluene: ethanol = 9:1 to obtain intermediate I-9 (24.58g, yield 79%), HPLC purity ≧99.86%. Mass spectrum m / z: 565.2785 (theoretical value: 565.2770).

[0182] Preparation of compound 9:

[0183] Under nitrogen protection, intermediate I-9 (18.10 g, 32.00 mmol), raw material c-9 (6.30 g, 32.00 mmol), Pd 2 (dba) 3(0.29g, 0.32mmol), BINAP (0.40g, 0.64mmol), NaOt-Bu (6.15g, 64.00mmol) and 160mL toluene solvent, stir the mixture, and heat the mixed solution of the above reactants under reflux for 4h. After the reaction is completed, cool to room temperature, add distilled water, extract with dichloromethane, stand and separate, collect the organic layer, dry it with anhydrous magnesium sulfate, filter, concentrate the filtrate by vacuum distillation, cool and crystallize, filter, and recrystallize the obtained solid with toluene to obtain compound 3 (16.37g, yield 75%), HPLC purity ≧99.97%. Mass spectrum m / z: 681.3021 (theoretical value: 681.3032). Theoretical element content (%) C 51 H 39 NO: C, 89.83; H, 5.77; N, 2.05. Measured element content (%): C, 89.85; H, 5.75; N, 2.07.

[0184] Synthesis Example 3: Preparation of Compound 30

[0185]

[0186] According to the same preparation method as compound 9 in Synthesis Example 2, a-9 was replaced by an equal mole of a-30, and the other steps were the same to obtain compound 30 (16.03 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 667.2861 (theoretical value: 667.2875). Theoretical element content (%) C 50 H 37 NO: C, 89.92; H, 5.58; N, 2.10. Measured element content (%): C, 89.90; H, 5.61; N, 2.07.

[0187] Synthesis Example 4: Preparation of Compound 33

[0188]

[0189] According to the same preparation method as compound 9 in Synthesis Example 2, b-9 was replaced by an equal molar amount of b-33, and the other steps were the same to obtain compound 33 (16.70 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 695.3170 (theoretical value: 695.3188). Theoretical element content (%) C 52 H 41 NO: C, 89.75; H, 5.94; N, 2.01. Measured element content (%): C, 89.77; H, 5.91; N, 2.03.

[0190] Synthesis Example 5: Preparation of Compound 56

[0191]

[0192] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 was replaced by an equal molar amount of b-56, and the other steps were the same to obtain compound 56 (17.25 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 709.3355 (theoretical value: 709.3345). Theoretical element content (%) C 53 H 43 NO: C, 89.67; H, 6.11; N, 1.97. Measured element content (%): C, 89.64; H, 6.13; N, 1.95.

[0193] Synthesis Example 6: Preparation of Compound 67

[0194]

[0195] According to the same preparation method of compound 9 in Synthesis Example 2, a-9 and b-9 were replaced by equimolar a-67 and b-67 respectively, and the other steps were the same to obtain compound 67 (19.06 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 793.4296 (theoretical value: 793.4284). Theoretical element content (%) C 59 H 55 NO: C, 89.24; H, 6.98; N, 1.76. Measured element content (%): C, 89.21; H, 6.96; N, 1.79.

[0196] Synthesis Example 7: Preparation of Compound 147

[0197]

[0198] According to the same preparation method as compound 9 in Synthesis Example 2, c-9 was replaced by an equal molar amount of c-147, and the other steps were the same to obtain compound 147 (18.19 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 757.3358 (theoretical value: 757.3345). Theoretical element content (%) C 57 H 43 NO: C, 90.32; H, 5.72; N, 1.85. Measured element content (%): C, 90.29; H, 5.75; N, 1.83.

[0199] Synthesis Example 8: Preparation of Compound 151

[0200]

[0201] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-151, b-151, c-151, respectively, and the other steps were the same to obtain compound 147 (17.38 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 743.3165 (theoretical value: 743.3188). Theoretical element content (%) C 56 H 41 NO: C, 90.41; H, 5.56; N, 1.88. Measured element content (%): C, 90.38; H, 5.53; N, 1.85. Synthesis Example 9: Preparation of Compound 166

[0202]

[0203] According to the same preparation method as compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-166 and c-166, respectively, and the other steps were the same to obtain compound 166 (17.47 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 768.3944 (theoretical value: 768.3925). Theoretical element content (%) C 56 H 32 D 10 N 2 O: C, 87.46; H, 6.81; N, 3.64. Measured element content (%): C, 87.43; H, 6.79; N, 3.62.

[0204] Synthesis Example 10: Preparation of Compound 182

[0205]

[0206] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-33 and c-182, respectively, and the other steps were the same to obtain compound 182 (18.65 g); HPLC purity ≥ 99.98%. Mass spectrum m / z: 771.3515 (theoretical value: 771.3501). Theoretical element content (%) C 58 H 45 NO: C, 90.24; H, 5.88; N, 1.81. Measured element content (%): C, 90.27; H, 5.91; N, 1.78.

[0207] Synthesis Example 11: Preparation of Compound 185

[0208]

[0209] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-56 and c-185, respectively, and the other steps were the same to obtain compound 185 (18.75 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 785.3672 (theoretical value: 785.3658). Theoretical element content (%) C 59 H 47 NO: C, 90.16; H, 6.03; N, 1.78. Measured element content (%): C, 90.14; H, 6.05; N, 1.80.

[0210] Synthesis Example 12: Preparation of Compound 201

[0211]

[0212] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-201 and c-151, respectively, and the other steps were the same to obtain compound 201 (20.61 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 869.4585 (theoretical value: 869.4597). Theoretical element content (%) C 65 H 59 NO: C, 89.72; H, 6.83; N, 1.61. Measured element content (%): C, 89.69; H, 6.85; N, 1.58.

[0213] Synthesis Example 13: Preparation of Compound 213

[0214]

[0215] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-213, b-213, c-213, respectively, and the other steps were the same to obtain compound 213 (17.95 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 803.3568 (theoretical value: 803.3583). Theoretical element content (%) C 58 H 49 NOSi: C, 86.63; H, 6.14; N, 1.74. Measured element content (%): C, 86.66; H, 6.12; N, 1.71.

[0216] Synthesis Example 14: Preparation of Compound 224

[0217]

[0218] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-224, b-224, c-224, respectively, and the other steps were the same to obtain compound 224 (18.41 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 845.4525 (theoretical value: 845.4535). Theoretical element content (%) C 63 H 51 D 4 NO: C, 89.43; H, 7.03; N, 1.66. Measured element content (%): C, 89.45; H, 7.01; N, 1.64.

[0219] Synthesis Example 15: Preparation of Compound 233

[0220]

[0221] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-233, b-233, c-233, respectively, and other steps were the same to obtain compound 233 (17.80 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 805.3356 (theoretical value: 805.3345). Theoretical element content (%) C 61 H 43 NO: C, 90.90; H, 5.38; N, 1.74. Measured element content (%): C, 90.88; H, 5.41; N, 1.70. Synthesis Example 16: Preparation of Compound 249

[0222]

[0223] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-249, b-249, c-249, respectively, and the other steps were the same to obtain compound 249 (19.22 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 849.3447 (theoretical value: 849.3429). Theoretical element content (%) C 63 H 47 NS: C, 89.01; H, 5.57; N, 1.65. Measured element content (%): C, 89.03; H, 5.55; N, 1.67. Synthesis Example 17: Preparation of Compound 294

[0224]

[0225] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-294, b-249, c-294, respectively, and the other steps were the same to obtain compound 294 (16.30 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 697.2819 (theoretical value: 697.2803). Theoretical element content (%) C 51 H 39 NS: C, 87.77; H, 5.63; N, 2.01. Measured element content (%): C, 87.75; H, 5.65; N, 2.04.

[0226] Synthesis Example 18: Preparation of Compound 306

[0227]

[0228] According to the same preparation method as compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-306 and c-306, respectively, and the other steps were the same to obtain compound 306 (17.36 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 774.3505 (theoretical value: 774.3512). Theoretical element content (%) C 54 H 42 D 5 NSSi: C, 83.67; H, 6.76; N, 1.81. Measured element content (%): C, 83.65; H, 6.73; N, 1.84.

[0229] Synthesis Example 19: Preparation of Compound 316

[0230]

[0231] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-316, b-316, c-316, respectively, and the other steps were the same to obtain compound 316 (17.81 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 797.3526 (theoretical value: 797.3511). Theoretical element content (%) C 56 H 51 NSSi: C, 84.27; H, 6.44; N, 1.75. Measured element content (%): C, 84.30; H, 6.41; N, 1.76.

[0232] Synthesis Example 20: Preparation of Compound 321

[0233]

[0234] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-321, b-321, c-321, respectively, and other steps were the same to obtain compound 321 (17.55 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 739.3286 (theoretical value: 739.3273). Theoretical element content (%) C 54 H 45 NS: C, 87.65; H, 6.13; N, 1.89. Measured element content (%): C, 87.62; H, 6.15; N, 1.90.

[0235] Synthesis Example 21: Preparation of Compound 327

[0236]

[0237] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-56 and c-327, respectively, and the other steps were the same to obtain compound 327 (17.90 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 801.3429 (theoretical value: 801.3429). Theoretical element content (%) C 59 H 47 NS: C, 88.35; H, 5.91; N, 1.75. Measured element content (%): C, 88.32; H, 5.89; N, 1.76.

[0238] Synthesis Example 22: Preparation of Compound 373

[0239]

[0240] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-373, b-33, c-373, respectively, and the other steps were the same to obtain compound 373 (18.40 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 787.3255 (theoretical value: 787.3273). Theoretical element content (%) C 58 H 45 NS: C, 88.40; H, 5.76; N, 1.78. Measured element content (%): C, 88.38; H, 5.74; N, 1.81.

[0241] Synthesis Example 23: Preparation of Compound 399

[0242]

[0243] According to the same preparation method of compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-294, b-399, c-399, respectively, and the other steps were the same to obtain compound 399 (16.98 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 757.2815 (theoretical value: 757.2803). Theoretical element content (%) C 56 H 39 NS: C, 88.74; H, 5.19; N, 1.85. Measured element content (%): C, 88.71; H, 5.22; N, 1.83.

[0244] Synthesis Example 24: Preparation of Compound 404

[0245]

[0246] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-294, b-249, C-404, respectively, and other steps were the same to obtain compound 404 (17.34 g); HPLC purity ≥ 99.91%. Mass spectrum m / z: 773.3130 (theoretical value: 773.3116). Theoretical element content (%) C 57 H 43 NS: C, 88.45; H, 5.60; N, 1.81. Measured element content (%): C, 88.42; H, 5.58; N, 1.79.

[0247] Synthesis Example 25: Preparation of Compound 427

[0248]

[0249] According to the same preparation method as compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-427 and c-427, respectively, and the other steps were the same to obtain compound 427 (19.09 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 949.4665 (theoretical value: 949.4681). Theoretical element content (%) C 70 H 63 NS: C, 88.47; H, 6.68; N, 1.47. Measured element content (%): C, 88.50; H, 6.70; N, 1.45.

[0250] Synthesis Example 26: Preparation of Compound 464

[0251]

[0252] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 and c-9 were replaced by equimolar amounts of b-464 and c-464, respectively, and the other steps were the same to obtain compound 464 (16.64 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 711.2943 (theoretical value: 711.2960). Theoretical element content (%) C 52 H 41 NS: C, 87.72; H, 5.80; N, 1.97. Measured element content (%): C, 87.69; H, 5.83; N, 1.95.

[0253] Synthesis Example 27: Preparation of Compound 503

[0254]

[0255] According to the same preparation method of compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-294, b-503, c-503, respectively, and other steps were the same to obtain compound 503 (18.01 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 839.3318 (theoretical value: 839.3334). Theoretical element content (%) C 60 H 45 N 3 S: C, 85.78; H, 5.40; N, 5.00. Measured element content (%): C, 85.80; H, 5.37; N, 5.04.

[0256] Synthesis Example 28: Preparation of Compound 507

[0257]

[0258] According to the same preparation method of compound 9 in Synthesis Example 2, c-9 was replaced by an equal mole of c-507, and the other steps were the same to obtain compound 507 (17.93 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 756.3518 (theoretical value: 756.3504). Theoretical element content (%) C 57 H 44 N 2 :C, 90.44;H, 5.86;N, 3.70. Measured element content (%): C, 90.41;H, 5.87;N, 3.68.

[0259] Synthesis Example 29: Preparation of Compound 601

[0260]

[0261] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-601, b-601, c-601, respectively, and the other steps were the same to obtain compound 601 (17.09 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 798.3992 (theoretical value: 798.3974). Theoretical element content (%) C 60 H 50 N 2 :C, 90.19;H, 6.31;N, 3.51. Measured element content (%): C, 90.21;H, 6.29;N, 3.52.

[0262] Synthesis Example 30: Preparation of Compound 603

[0263]

[0264] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-321, b-321, c-603, and other steps were the same to obtain compound 603 (17.09 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 874.4275 (theoretical value: 874.4287). Theoretical element content (%) C 66 H 54 N 2 :C, 90.58;H, 6.22;N, 3.20. Measured element content (%): C, 90.60;H, 6.21;N, 3.18.

[0265] Synthesis Example 31: Preparation of Compound 641

[0266]

[0267] According to the same preparation method as compound 9 in Synthesis Example 2, a-9, b-9, c-9 were replaced by equimolar a-641, b-33, c-641, respectively, and other steps were the same to obtain compound 641 (18.43 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 824.4138 (theoretical value: 824.4130). Theoretical element content (%) C 62 H 52 N 2 :C, 90.25;H, 6.35;N, 3.40. Measured element content (%): C, 90.22;H, 6.37;N, 3.38.

[0268] Synthesis Example 32: Preparation of Compound 665

[0269]

[0270] According to the same preparation method of compound 9 in Synthesis Example 2, b-9 was replaced by an equal mole of b-665, and the other steps were the same to obtain compound 665 (18.00 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 771.3511 (theoretical value: 771.3501). Theoretical element content (%) C 58 H 45 NO: C, 90.24; H, 5.88; N, 1.81. Measured element content (%): C, 90.27; H, 5.90; N, 1.78.

[0271] Device Embodiment

[0272] In the present invention, the ITO glass substrate is ultrasonically cleaned twice with 5% glass cleaning liquid, each time for 20 minutes, and then ultrasonically cleaned twice with deionized water, each time for 10 minutes. Acetone and isopropyl ketone are ultrasonically cleaned for 20 minutes in sequence, and dried at 120°C. The organic materials are all sublimated, and the purity is above 99.99%.

[0273] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0274] The device is prepared by 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 separately. 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 should be maintained at 5×10 -5 Pa, the organic layer and the 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.

[0275] Example 1: Preparation of organic electroluminescent device 1

[0276] ITO was used as an anode on a glass substrate; 20 nm of HT-1:HI-1 (mixed in a mass ratio of 95%:5%) was vacuum-deposited on the anode to form a hole injection layer; 35 nm of the compound 9 of the present invention was vacuum-deposited on the hole injection layer to form a hole transport layer; 35 nm of BH-1:BD-1 (mixed in a mass ratio of 97%:3%) was vacuum-deposited on the hole transport layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum-deposited on the light-emitting layer to form an electron transport layer; 1.0 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.

[0277] Examples 2 to 31: Preparation of organic electroluminescent devices 2 to 31

[0278] The compound 9 in the hole transport layer of Example 1 was replaced by compound 30, compound 33, compound 56, compound 67, compound 147, compound 151, compound 166, compound 182, compound 185, compound 201, compound 213, compound 224, compound 233, compound 249, compound 294, compound 306, compound 316, compound 321, compound 327, compound 373, compound 399, compound 404, compound 427, compound 464, compound 503, compound 507, compound 601, compound 603, compound 641, and compound 665, respectively, and the other steps were the same to obtain organic electroluminescent devices 2 to 31.

[0279] Comparative Examples 1 to 3: Preparation of Comparative Organic Electroluminescent Devices 1 to 3

[0280] The compound 9 in the hole transport layer of Example 1 was replaced by R-1, R-2, and R-3 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 to 3.

[0281]

[0282]

[0283] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 31 of the present invention and Comparative Examples 1 to 3 are shown in Table 1.

[0284] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0285]

[0286]

[0287] Note: T95 refers to the current density of 10mA / cm2 Under the condition, the time taken for the device brightness to decay to 95%;

[0288] It can be concluded from Table 1 that, compared with Comparative Examples 1 to 3, when the fluorene-containing amine compound represented by Formula 1 of the present invention is used in the hole transport layer of the organic electroluminescent device, the efficiency of the organic electroluminescent device is effectively improved, and the service life of the device is improved, which further indicates that the compound of the present invention has excellent hole transport ability.

[0289] Example 32: Preparation of organic electroluminescent device 32

[0290] ITO is used as an anode on a glass substrate; 20 nm of HT-1:HI-1 (mixed in a mass ratio of 96%:4%) is vacuum evaporated on the anode to form a hole injection layer; 40 nm of compound HT-1 is vacuum evaporated on the hole injection layer to form a first hole transport layer; the compound 9 of the present invention is vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; 32 nm of GH-1:GH-2:GD-1 (mixed in a mass ratio of 48:48:4) is vacuum evaporated on the second hole transport layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) is vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF is vacuum evaporated on the electron transport layer to form an electron injection layer; 120 nm of Al is vacuum evaporated on the electron injection layer to form a cathode.

[0291] Examples 33-62: Preparation of organic electroluminescent devices 33-62

[0292] The compound 9 in the second hole transport layer of Example 32 is replaced by compound 30, compound 33, compound 56, compound 67, compound 147, compound 151, compound 166, compound 182, compound 185, compound 201, compound 213, compound 224, compound 233, compound 249, compound 294, compound 306, compound 316, compound 321, compound 327, compound 373, compound 399, compound 404, compound 427, compound 464, compound 503, compound 507, compound 601, compound 603, compound 641, and compound 665, respectively, and the other steps are the same to obtain organic electroluminescent devices 33 to 62.

[0293] Comparative Examples 4 to 6: Preparation of Comparative Organic Electroluminescent Devices 4 to 6

[0294] The compound 9 in the second hole transport layer of Example 32 was replaced by R-4, R-5, and R-6 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4 to 6.

[0295]

[0296]

[0297] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 32 to 62 of the present invention and Comparative Examples 4 to 6 are shown in Table 2.

[0298] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0299]

[0300]

[0301] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0302] It can be seen from the results in Table 2 that when the fluorene-containing amine compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device and is used as a second hole transport layer material in the hole transport region, the performance of the device is significantly improved compared with Comparative Examples 4 to 6, showing the advantages of high luminous efficiency and long service life, indicating that it has a good synergistic effect.

[0303] Example 63: Preparation of organic electroluminescent device 63

[0304] ITO / Ag / ITO was used as an anode on a glass substrate; 20 nm of HI-2:HI-1 (mixed in a mass ratio of 95%:5%) was vacuum evaporated on the anode to form a hole injection layer; 45 nm of HI-2 was vacuum evaporated on the hole injection layer to form a hole transport layer; 25 nm of RH-1:RD-1 (mixed in a mass ratio of 96%:4%) was vacuum evaporated on the hole transport layer to form a light-emitting layer; 20 nm of ET-2:LiQ (mixed in a mass ratio of 1:1) was vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF was vacuum evaporated on the electron transport layer to form an electron injection layer; 10 nm of Mg and Ag (mass ratio of 1:9) were vacuum evaporated on the electron injection layer to form a cathode, and 100 nm of compound 9 was vacuum evaporated on the cathode to form a covering layer.

[0305] Examples 64 to 82: Preparation of organic electroluminescent devices 64 to 82

[0306] The compound 9 in the covering layer of Example 63 is replaced by compound 33, compound 56, compound 67, compound 147, compound 151, compound 166, compound 182, compound 185, compound 201, compound 249, compound 306, compound 321, compound 327, compound 373, compound 404, compound 464, compound 507, compound 601, and compound 603, respectively, and the other steps are the same to obtain organic electroluminescent devices 64-82.

[0307] Comparative Examples 10-11: Preparation of Comparative Organic Electroluminescent Devices 10-11

[0308] The compound 9 in the covering layer of Example 63 was replaced by R-7 and R-8 respectively, and the other steps were the same to obtain comparative examples 10 to 11.

[0309]

[0310] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 63 to 82 of the present invention and Comparative Examples 10 to 11 are shown in Table 3.

[0311] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0312]

[0313] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0314] It can be seen from the results in Table 3 that when the fluorene-containing amine compound of the present invention is applied to the covering layer of an organic electroluminescent device, the luminous efficiency and service life of the device are greatly improved. In summary, the fluorene-containing amine compound provided by the present invention is a class of OLED materials with excellent performance and has a good application prospect.

[0315] 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-containing amine compound, characterized in that: Having the general formula shown in Structural Formula 1, Wherein, Ar1 is selected from the group shown in Formula 2; Ar2 is selected from the group shown in Formula 3; The ring A is selected from a substituted or unsubstituted C3-C8 monocyclic alicyclic group; The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, 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 the two adjacent R1s and two R2s are connected to each other to form a substituted or unsubstituted ring; a is selected from 1, 2, 3 or 4; b is selected from 1, 2 or 3; The R3 is selected from any one of 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 group and a C6-C30 aromatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group; The R4 is selected from any one of a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C30 aromatic ring fused ring, and a substituted or unsubstituted C2-C30 heteroaromatic group; The R5 and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R5s and two R6s are connected to each other to form a substituted or unsubstituted ring; c is selected from 1, 2, 3 or 4; d is selected from 1, 2, 3 or 4; Said X is selected from O, S or N(R8); The R8 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group; The ring B is selected from any one of a C6-C30 aryl group substituted or unsubstituted by a deuterium atom, and a C2-C30 heteroaryl group substituted or unsubstituted by a deuterium atom; The R7 is the same or different and is selected from hydrogen or deuterium; the e is selected from 1 or 2; The L1, L2, and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring condensed sub-ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

2. The fluorene-containing amine compound according to claim 1, characterized in that: The ring A is selected from any one of the following groups: The R9s are the same or different and are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, hydroxyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl; The f1 is independently selected from 1, 2, 3 or 4; the f2 is independently selected from 1, 2, 3, 4, 5 or 6; the f3 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; the f4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the f5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; when two or more R9 are present, the two or more R9 are the same or different from each other.

3. The fluorene-containing amine compound according to claim 1, characterized in that: The formula 2 is selected from any one of the following groups: Said R5, R6 are 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, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, tri Any one or more of oxazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R5s and the two R6s are connected to each other to form a substituted or unsubstituted ring; the c is selected from 1, 2, 3 or 4; the d is selected from 1, 2, 3 or 4; The R a The same or different R 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 C2-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; in the case of being substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R a are connected to each other to form a substituted or unsubstituted ring; The R b 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, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, silyl, in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; The g1 is independently selected from 1, 2, 3, 4 or 5; the g2 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the g3 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the g4 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the g5 is independently selected from 1, 2, 3 or 4; the g6 is independently selected from 1, 2, 3, 4, 5, 6 or 7; the g7 is independently selected from 1, 2 or 3; the g8 is independently selected from 1, 2, 3, 4, 5 or 6; the g9 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; the g 10 Independently selected from 1 or 2; said g 11 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

4. The fluorene-containing amine compound according to claim 3, characterized in that: The R a at least one of the following groups is selected from deuterium, cyano, halogen, nitro, 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, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, silyl, in the case of being substituted by multiple substituents, the multiple substituents are the same or different; or the two adjacent R a They are connected to each other to form a substituted or unsubstituted ring.

5. The fluorene-containing amine compound according to claim 1, characterized in that: The formula 3 is selected from any one of the following groups: Said X is selected from O, S or N(R8); The R7 are the same or different and are selected from hydrogen or deuterium; the e is independently selected from 1 or 2; The R c are identically or differently selected from hydrogen or deuterium; said h1 is independently selected from 1, 2 or 3; said h2 is independently selected from 1, 2, 3, 4 or 5; said h3 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said h4 is independently selected from 1 or 2; said h5 is independently selected from 1, 2, 3 or 4; said h6 is independently selected from 1, 2, 3, 4, 5 or 6; The R8 is selected from hydrogen, deuterium, substituted or unsubstituted 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, Any one of tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl and silyl.

6. The fluorene-containing amine compound according to claim 1, characterized in that: The L1, L2, and L3 are independently selected from a single bond or any one of the following groups or combinations thereof: The z are selected from CH or N atoms the same or differently; the z at the bonding site is selected from C; The R 11 The same or different groups are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 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; The Y1 is independently selected from an O atom, a S atom, a C(R f R g ) or N(R d ); The Y2 is independently selected from an O atom, a S atom or a N(R h ); The ring D is selected from a substituted or unsubstituted C3-C15 alicyclic group; The R f , R g is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, or the R f and R g are connected to each other to form a substituted or unsubstituted ring; The R d , R h Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group; The j1 is independently selected from 1, 2, 3 or 4; the j2 is independently selected from 1, 2 or 3; and the j3 is independently selected from 1 or 2.

7. The fluorene-containing amine compound according to claim 1, characterized in that: The fluorene-containing amine 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, characterized in that: The organic layer contains the fluorene-containing amine 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, an n-type charge generation layer, a p-type charge generation layer, and an electron transport region, and at least one layer of the hole transport region or the p-type charge generation layer contains the fluorene-containing amine compound described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a covering layer. The covering layer is located on the side of the cathode away from the anode. The covering layer contains the fluorene-containing amine compound according to any one of claims 1 to 7.

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