Fluorene compound and organic electroluminescent device thereof

Abstract

The invention provides a fluorene compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The fluorene compound provided by the invention has relatively high electron mobility, an energy level matched with an adjacent functional layer, and good film-forming property and thermal stability. When the compound is applied to an organic electroluminescent device as an electron transport layer material, the transmission efficiency of electrons in the device can be effectively improved, the recombination probability of holes and electrons in a light-emitting layer is improved, the driving voltage of the device can be effectively reduced, the light-emitting efficiency of the device is improved, and the service life of the device is prolonged. Meanwhile, when the fluorene compound is used as a hole blocking layer material in the organic electroluminescent device, holes can be effectively prevented from being diffused to one side of an electron transmission region, the holes are effectively limited in a luminescent layer region, and the performance of the organic electroluminescent device is further improved.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, specifically to a fluorene compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a next-generation display and lighting technology, possess advantages such as self-illumination, high contrast, wide viewing angle, low power consumption, and flexibility. They have been widely applied in smartphones, televisions, wearable devices, and other fields, becoming one of the core development directions of the display industry. A typical OLED device structure includes an anode, a cathode, and various organic functional layers disposed between the anode and cathode, such as a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). The synergistic effect of these functional layers enables efficient carrier injection, transport, and recombination, directly determining the device's luminous efficiency, lifetime, and stability.

[0003] In OLED device structures, the core function of the electron transport layer material is to efficiently transport electrons to the emissive layer. Its electron mobility, energy level matching, and chemical stability significantly impact device performance. Currently, these materials generally suffer from lower electron mobility than hole mobility, causing the exciton recombination region to shift towards the electron transport layer. When holes penetrate the emissive layer into the electron transport layer, it reduces the device's luminous efficiency, accelerates device aging, and shortens its lifespan. To balance electron and hole transport rates and improve OLED device performance, a hole blocking layer is typically added between the electron transport layer and the emissive layer. This layer optimizes energy level alignment, lowers the electron injection barrier, promotes efficient electron entry into the emissive layer, and effectively blocks further hole diffusion, thus confining the carrier recombination region within the emissive layer. This helps improve exciton utilization efficiency, thereby enhancing the device's luminous performance and lifespan. However, existing hole blocking materials still suffer from poor energy level matching with the emissive layer, failure to effectively lower the injection barrier, and limited hole blocking capabilities, adversely affecting device efficiency and lifespan.

[0004] As OLED technology advances towards higher resolution, higher brightness, longer lifespan, and greater flexibility, the development of existing electron transport layer materials and hole blocking layer materials has become a key factor restricting device upgrades. Therefore, developing electron transport layer materials and hole blocking layer materials with high electron mobility, good hole blocking capability, excellent stability, and good energy level matching has become an important research direction in the current OLED field. Summary of the Invention

[0005] To address the problems existing in the prior art, the present invention provides a fluorene compound and its organic electroluminescent device, which can reduce the driving voltage of the organic electroluminescent device and significantly improve the luminous efficiency and lifespan of the organic electroluminescent device.

[0006] This invention provides a fluorene compound having the structure shown in Formula I.

[0007] In Formula I, L is selected from any one of substituted C6-C30 arylene, substituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, and substituted C6-C30 heteroarylene. At least one of the "substituted" groups in L is selected from the group of formula II, and the remainder is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C4-C30 heteroaryl group and combination thereof; The L2 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroarylene, and combinations thereof.

[0008] The L3 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group and combination thereof; Ar1 is selected from formula III-1 or formula III-2. When Ar1 is selected from formula III-2, L3 is not selected from single bonds. X is selected from O, S, N(R) c Any one of the following; The v and a may be the same or different from each other, and are independently selected from CH or N atoms. When v and a are bonded to other groups, the v and a are selected from C atoms. The R a Rb R1 and R2 may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; or R2 may be the same as or different from each other, and are independently selected from any one of the following: hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C30 alkyl, substituted or unsubstituted ... alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, a R b They can connect to each other to form substituted or unsubstituted rings; or R a R b Either of them can be directly bonded to L1; The R c It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The Rs may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When there are two or more R1s, the two or more R1s are the same or different from each other; or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The m is selected from 0, 1, 2, 3 or 4. When there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to form a substituted or unsubstituted benzene ring, pyridine ring or pyrimidine ring.

[0009] 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 either the anode or the cathode, and the organic layer comprises any one or more of the fluorene compounds described in the present invention.

[0010] Beneficial effects: The fluorene compounds provided by this invention possess suitable energy levels and excellent electron transport properties. When used as electron transport materials, they can enhance the electron migration rate in devices, effectively balance the transport efficiency of holes and electrons, reduce the exciton recombination region shift caused by carrier transport imbalance, and thus increase the recombination probability of holes and electrons within the emissive layer, enhancing the device's luminous efficiency and extending its lifespan. When used as hole-blocking materials, they can promote electron injection into the emissive layer by lowering the energy level barrier and effectively block hole diffusion into the electron transport layer, confining the exciton recombination process within the emissive layer, further improving the device's luminous efficiency and lifespan. Detailed Implementation

[0011] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0012] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0013] In the instruction manual, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0014] In this invention, when the position of the substituent on the aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the aromatic ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0015] In this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , And so on.

[0016] In this invention, "two adjacent groups connecting to form a ring" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining adjacent groups with each other and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Specific examples are shown below:

[0017] In this invention, the ring formed by the 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 the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a spiro ring, or a fused ring, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, indene, phenanthrene, pyrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, etc., but is not limited to these.

[0018] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0019] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, trifluoromethyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylboron, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6 ~C30 aryloxy group, substituted or unsubstituted C6~C30 arylamino group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 arylboryl group, substituted or unsubstituted silyl group, preferably deuterium, halogen, cyano, nitro, trifluoromethyl, C1~C12 alkyl group, C3~C12 cycloalkyl group, C2~C12 alkenyl group, C6~C30 aryl group, C2~C30 heteroaryl group, silyl group, where the substituted group is the same as or different from each other when substituted by multiple substituents;Preferably, it means not being substituted or being substituted by one or more substituents selected from the group consisting of: deuterium, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated cyclobutane, cyclopentane Alkyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, vinyl, isopropenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornane alkyl, deuterated norbornelyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl The following groups are included: yl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazole, benzofuranyl, benzothiophene, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzooxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the substituents may be identical or different from each other, and adjacent substituents may be linked to form a ring.

[0020] The halogens described in this invention include fluorine, chlorine, bromine, and iodine.

[0021] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, and most preferably 1 to 6. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl groups. The branched alkyl group includes, but is not limited to, isomers of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups.

[0022] The alkenyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl group or a branched alkenyl group. The alkenyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, and most preferably 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited thereto.

[0023] The cycloalkyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from a cyclic alkane molecule. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, and most preferably 3 to 10. The cycloalkyl group includes monocyclic, polycyclic, and bridged cycloalkyl groups. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, fentanyl, isocamphenyl, etc., but are not limited thereto.

[0024] The silyl group mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom from a silane molecule, which can be formed by -Si(R) k )3 groups represent, where each R k The same or different are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 12, and most preferably 1 to 6. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, and most preferably 3 to 10. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and most preferably 6 to 12. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, etc.

[0025] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, fused-ring aryl, or a combination thereof. The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and most preferably 6 to 12. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this.

[0026] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule. The aliphatic ring preferably has 3 to 20 carbon atoms, more preferably 3 to 15, and most preferably 3 to 10. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0027] The fused cyclic group of aromatic and aliphatic rings described in this invention refers to a monovalent group formed by removing one hydrogen atom after an aromatic ring and an aliphatic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and most preferably 6 to 12. The aliphatic ring has 3 to 20 carbon atoms, more preferably 3 to 15, and most preferably 3 to 10. Examples of the fused cyclic group of aromatic and aliphatic rings include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0028] The heteroaryl group described in this invention refers to a group obtained by substituting at least one aromatic carbon atom in an aryl group with a heteroatom. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, silicon, selenium, boron, and phosphorus atoms. The heteroaryl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20, and most preferably 3 to 12. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or a combination thereof. The monocyclic heteroaryl groups include furanyl, thienyl, oxazolyl, pyrrolyl, imidazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, phenylfuranyl, phenylthienyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothienyl, benzofuranyl, benzothiazolyl, indolyl, benzooxazolyl, dibenzooxazolyl, benzoimidazolyl, dibenzoimidazolyl, benzotriazolyl, benzothiazolyl, dibenzoxazolyl, etc. Furanyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazoyl, benzocarbazoyl, indocarbazoyl, benzofuranocarbazoyl, benzothiophenocarbazoyl, acridineyl, 9,10-dihydroacridyl, naphridyl, indolyl, phenoxazinyl, phenthiazinyl, phenoxthiazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazoline, benzoquinazoline, quinoxolinyl, benzoquinoxolinyl, o-phenanthroline, spirofluorenexanthyl, spirofluorenethionthanthyl, etc., but not limited to these.

[0029] The arylene group described in this invention refers to the collective term for divalent groups remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be described using the same principles as the aryl group described above, except that the arylene group is a divalent group.

[0030] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The above description of heteroaryl groups can be applied to it, the difference being that the heteroaryl group is a divalent group.

[0031] The fused cyclic groups of aromatic and aliphatic rings described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused aromatic and aliphatic rings. The above description of fused cyclic groups of aromatic and aliphatic rings can be applied, the difference being that the fused cyclic groups of aromatic and aliphatic rings are divalent groups.

[0032] This invention provides a fluorene compound having the structure shown in Formula I.

[0033] In Formula I, L is selected from any one of substituted C6-C30 arylene, substituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, and substituted C6-C30 heteroarylene. At least one of the "substituted" groups in L is selected from the group of formula II, and the remainder is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C4-C30 heteroaryl group and combination thereof; The L2 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroarylene, and combinations thereof.

[0034] The L3 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group and combination thereof; Ar1 is selected from formula III-1 or formula III-2. When Ar1 is selected from formula III-2, L3 is not selected from single bonds. X is selected from O, S, N(R) c Any one of the following; The v and a may be the same or different from each other, and are independently selected from CH or N atoms. When v and a are bonded to other groups, the v and a are selected from C atoms. The R a R b R1 and R2 may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; or R2 may be the same as or different from each other, and are independently selected from any one of the following: hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C30 alkyl, substituted or unsubstituted ... alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, a R b They can connect to each other to form substituted or unsubstituted rings; or R a R b Either of them can be directly bonded to L1; The R c It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The Rs may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When there are two or more R1s, the two or more R1s are the same or different from each other; or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The m is selected from 0, 1, 2, 3 or 4. When there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to form a substituted or unsubstituted benzene ring, pyridine ring or pyrimidine ring.

[0035] Preferably, the Selected from any one of the following groups, ; The v may be the same as or different from each other, and are selected from CH or N atoms. When v is bonded to other groups, the v is selected from C atoms. The Y is selected from O, S, C(R) x R y ), N(R z Any one of the following; The ring A is selected from substituted or unsubstituted C3~C12 aliphatic rings; The R a R b R1 may be the same as or different from each other, and is independently selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1~C20 alkyl, substituted or unsubstituted C2~C20 alkenyl, substituted or unsubstituted C3~C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aromatic ring and C3~C20 aliphatic ring fused ring group, substituted or unsubstituted C2~C30 heteroaryl; a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The R x R y They may be identical or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R x R y They can connect with each other to form substituted or unsubstituted rings; The R z Selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused-ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R z It can be directly bonded to L1; The L a It is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, and combinations thereof.

[0036] Preferably, each six-membered ring containing v has at most 3, or at most 2, or at most 1 selected N atom.

[0037] Preferably, the Selected from any one of the following groups,

[0038] ; R1 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrimidinyl, etc. Azinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl, or indoleyl; or two adjacent R1 groups forming a substituted or unsubstituted benzene ring or naphthyl ring; The number b1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the number b2 is selected from 0, 1, 2, 3, or 4; the number b3 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the number b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the number b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the number b8 is selected from 0, 1, or 2; the number b9 is selected from 0, 1, 2, 3, 4, or 5; the number b...10 The value b is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, wherein b 12 Choose from 0, 1, 2, or 3.

[0039] Preferably, L3 is selected from any one or a combination of the following groups, either single-bonded, substituted, or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, trimethyleneene, pyridylene, pyrazinylene, pyridazinylene, quinolinylene, isoquinolinylene, quinazolinylene, quinoxalinylene, naphthidylene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiopheneyl. In L3, "substituted or unsubstituted," the substituent is selected from deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, and dibenzothiophene. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0040] Preferably, Formula II is selected from any one of the following groups.

[0041]

[0042]

[0043] .

[0044] Preferably, the Ar1 group is selected from any one of the following groups:

[0045]

[0046]

[0047] ; X is selected from O, S, N(R)c Any one of the following; The R2 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl. , pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl or indoleyl, or two adjacent R2s connected to form a substituted or unsubstituted benzene ring, pyridine ring or pyrimidine ring; The R c Selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrimidinyl The following are listed: pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiophene, or indoleyl. c1 is selected from 0, 1, 2, 3 or 4, c2 is selected from 0, 1, 2 or 3, and c3 is selected from 0, 1 or 2.

[0048] Preferably, L2 is selected from single bonds or any one of the following groups:

[0049] ; The y and t1 may be the same or different from each other, and are independently selected from C(R4) or N atoms. When y is bonded to other groups, the y is selected from C atoms. The t2 is selected from O, S, N(R) d Any one of the following; The t3 is selected from O, S, N(R) d ), C(R e Any one of 2; The R d It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The R4, R e They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl. When two or more R4s are present, the two or more R4s may be the same as or different from each other, or two adjacent R4s may be connected to each other to form substituted or unsubstituted rings. The d1 is selected from 0 or 1.

[0050] Preferably, L2 is selected from single bonds or any one of the following groups: ; The R4 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, tri- Phenylidene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiophene, or indoleyl; f1 is selected from 0, 1, 2, 3 or 4; f2 is selected from 0, 1, 2, 3, 4, 5 or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; f5 is selected from 0, 1 or 2; f6 is selected from 0, 1, 2 or 3; f7 is selected from 0, 1, 2, 3, 4 or 5; and f8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0051] Preferably, L1 is selected from single bonds or any of the following groups: ; The R5 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, tri- Phenylidene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiophene, or indoleyl; The g1 is selected from 0, 1, 2, 3 or 4; the g2 is selected from 0, 1, 2, 3, 4, 5 or 6; the g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the g5 is selected from 0, 1, 2 or 3; the g6 is selected from 0, 1 or 2; the g7 is selected from 0, 1, 2, 3, 4 or 5; and the g8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0052] Preferably, the L is selected from any one of the following groups: ; At least one R6 in each group is selected from a group of formula II, and the remaining R6 are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups, as shown below: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, etc. Norborneol alkyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl or indoleyl; h1 is selected from 0, 1, 2, 3 or 4; h2 is selected from 0, 1, 2, 3, 4, 5 or 6; h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; h4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; h5 is selected from 0, 1, 2, 3, 4 or 5; h6 is selected from 0, 1, 2 or 3; h7 is selected from 0, 1 or 2; and h8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0053] Preferably, each group has one, two, three or more R6 groups selected from groups of formula II.

[0054] More preferably, the L is selected from any one of the following groups:

[0055]

[0056]

[0057] ; Most preferably, Formula I is selected from any one of the following compounds.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] .

[0245] The above are only some specific examples of fluorene compounds of Formula I of the present invention. However, the present invention is not limited to these chemical structures. All compounds with Formula I as the parent structure and whose substituents fall within the scope defined by the present invention are within the protection scope of the present invention.

[0246] The preparation method of the fluorene compounds shown in Formula I of this invention is not particularly limited, and conventional methods well known to those skilled in the art can be used, such as the Miyaura borylation reaction, the Suzuki coupling reaction, etc. The fluorene compounds shown in Formula I of this invention can be prepared using the synthetic route shown below, but are not limited thereto.

[0247] Preparation of compound I:

[0248] When L is selected In this case, raw material A can be prepared by the following synthetic route, but is not limited to this:

[0249] Preparation of raw material c:

[0250] Preparation of raw material d: or

[0251] The X a X b X c X d X e X f X g X hWhether the same or different, they can be independently selected from Cl, Br, and I.

[0252] Alternatively, the order of the above reactions can be changed to obtain the fluorene compounds represented by Formula I of the present invention.

[0253] 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 either the anode or the cathode, and the organic layer comprises at least one of the fluorene compounds described in the present invention.

[0254] Preferably, the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a capping layer containing at least one of the fluorene compounds described in this invention.

[0255] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The electron transport region is located between the light-emitting layer and the cathode, and the electron transport region contains at least one of the fluorene compounds described in this invention.

[0256] More preferably, the electron transport region comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the fluorene compounds described in this invention.

[0257] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer, which includes at least one of the fluorene compounds described in this invention.

[0258] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole-blocking layer, which includes at least one of the fluorene compounds described in this invention.

[0259] Preferably, the light-emitting layer comprises at least one of the fluorene compounds described in this invention.

[0260] The organic electroluminescent devices described in this invention are typically fabricated on a substrate. The selection of the substrate material prioritizes stability during the formation of the electrodes and organic layers, and preferably uses materials that do not undergo deformation or chemical changes. Specific examples of substrate materials usable in this invention include, but are not limited to, glass, quartz, plastics, polymer films, and silicon.

[0261] This invention does not impose any particular limitation on the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The following describes each organic layer and the electrodes on both sides of the organic electroluminescent device: The anode of this invention preferably has a high work function, improving hole injection efficiency. The anode material includes, but is not limited to, transparent conductive metal oxides, metals, metal alloys, and conductive polymers. Specific examples may include vanadium, copper, silver, gold, magnesium-silver (Mg-Ag), aluminum-lithium (Al-Li), zinc oxide (ZnO), tin oxide (SnO2), indium tin oxide (ITO), indium zinc oxide (IZO), ZnO / Al, SnO2 / Sb, ITO / Ag / ITO, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, polyaniline, etc., but are not limited to these.

[0262] The hole injection layer described in this invention preferably uses a material with good hole injection capability, which can effectively reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer. The hole injection material includes arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, etc. Specific examples may include copper phthalocyanine (CuPc), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), etc., but is not limited to these.

[0263] The hole transport layer described in this invention is preferably made of a material with high hole mobility. The hole transport material includes, but is not limited to, carbazole derivatives, triarylamine derivatives, benzidine derivatives, fluorene derivatives, phthalocyanine compounds, etc. 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), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 1,3,5 Tris(9-carbazolyl)benzene (TCB), 4,4',4”-tris(carbazolyl-9-yl)triphenylamine (TCTA), etc., but not limited to these.

[0264] The electron blocking layer of this invention is preferably made of a material with good hole transport and electron blocking capabilities, which can effectively transport holes and restrict electrons from escaping to the interface of the light-emitting layer. The electron blocking material includes, but is not limited to, aromatic amine derivatives, carbazole derivatives, fluorene derivatives, etc. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), etc., but is not limited to these.

[0265] The light-emitting layer of the present invention may be composed of only the guest material, or it may be in the form of dispersing the guest material in the host material, wherein the host material may be composed of a single material or multiple materials.

[0266] In this invention, the host material must possess bipolar charge transport characteristics and have appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, fused polycyclic aromatic compounds, aromatic amine derivatives, carbazole derivatives, stilbeneylaryl derivatives, anthracene derivatives, and pyrene derivatives. Specific examples may include, but are not limited to, 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 1,3-bis(N-carbazole)benzene (MCP), 9,10-bis(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN), tris(8-hydroxyquinoline)aluminum (Alq3), etc.

[0267] In this invention, the guest material can be a fluorescent material, a phosphorescent material, or a TADF material, or a combination of fluorescent and phosphorescent materials. The guest material includes, but is not limited to, aromatic amine derivatives, boron nitrogen compounds, fluoranthene derivatives, pyrene derivatives, perylene derivatives, and metal complexes. Specific examples may include tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), etc., but is not limited to these.

[0268] The hole-blocking layer of this invention is preferably made of a material with good electron transport and hole blocking capabilities, which can effectively transport electrons and restrict the escape of holes to the interface of the light-emitting layer. The hole-blocking layer material includes metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, aziridine derivatives, triazole derivatives, etc., but is not limited to these. Specific examples may include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine (TmPyPB), fluorene compounds of this invention, etc., but are not limited to these. Fluorene compounds of this invention are preferred.

[0269] The electron transport layer of this invention is preferably made of a material with high electron mobility. The electron transport material includes, but is not limited to, imidazole derivatives, phenanthroline derivatives, pyridine derivatives, quinoline derivatives, azabenzene derivatives, oxazole derivatives, thiazole derivatives, and metal complexes. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridylquinoline-2-yl)benzene (TPyQB), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), and fluorene compounds of this invention, but are not limited to these. Fluorene compounds of this invention are preferred.

[0270] The electron injection layer of this invention is preferably made of a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. The electron injection material includes alkali metals, alkaline earth metals, rare earth metals, oxides, halides, and organic complexes containing these metals. Specific examples include lithium (Li), ytterbium (Yb), terbium (Tb), lithium fluoride (LiF), calcium fluoride (CaF2), lithium 8-hydroxyquinoline (Liq), lithium oxide (Li2O), barium oxide (BaO), cesium carbonate (Cs2CO3), and fluorene compounds as described in this invention, but are not limited thereto. Fluorene compounds as described in this invention are preferred.

[0271] The cathode of the present invention is preferably made of a material with a low work function. The cathode material includes metals, alloys, metal oxides, etc., and specific examples may include lithium (Li), magnesium (Mg), silver (Ag), aluminum (Al), indium (In), tin (Sn), LiF / Al, Mg / Ag, etc., but are not limited thereto.

[0272] The capping layer described in this invention is provided on the outside of either the anode or the cathode, and preferably uses a material with a high refractive index that contributes to improving the light efficiency of the organic light-emitting device, especially the external light-emitting efficiency. The capping layer material includes, but is not limited to, metal oxides, metal nitrides, metal fluorides, aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the capping layer material may include, but are not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), zirconium oxide (ZrO), zinc oxide (ZnO), silicon dioxide (SiO2), cesium fluoride (CsF), lithium fluoride (LiF), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), etc.

[0273] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0274] The preparation method of each thin film in the organic electroluminescent device of the present invention is not particularly limited. Vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, dip coating, etc. can be used, but are not limited to these.

[0275] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0276] The organic electroluminescent device provided by this invention can be widely used in electronic devices and lighting, specifically in products such as mobile phones, tablets, smart wearable devices, televisions, VR devices, and in-vehicle systems.

[0277] The following embodiments are provided to illustrate specific implementations of the present invention in more detail, but are merely illustrative examples, and the scope of this specification is not limited to these embodiments.

[0278] Preparation and characterization of compounds: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.

[0279] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0280] Synthesis Example 1: Preparation of Intermediate e-296

[0281] Under a nitrogen atmosphere, d-45 (35.55 g, 80.00 mmol), g-296 (20.37 g, 88.00 mmol), potassium carbonate (16.58 g, 120.00 mmol), 300 mL toluene, 150 mL ethanol, and 150 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.04 g, 0.90 mmol) was added. The reaction system was heated and stirred, and refluxed for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from the filter cake using a toluene:ethanol ratio of 6:1 to obtain intermediate e-296 (28.89 g, yield 77%); HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 468.1631 (theoretical value: 468.1645).

[0282] Synthesis Example 2: Preparation of Intermediate e-500

[0283] Following the preparation method of Synthesis Example 1, d-45 was replaced with an equimolar amount of d'-500 to obtain intermediate e-500 (19.08 g), with an HPLC purity ≥99.76%. Mass spectrometry m / z: 305.0959 (theoretical value: 305.0971).

[0284] Synthesis Example 3: Preparation of Intermediate e-677

[0285] Following the preparation method of Synthesis Example 1, d-45 was replaced with an equimolar amount of d'-677 to obtain intermediate e-677 (31.50 g), with an HPLC purity ≥99.79%. Mass spectrometry m / z: 517.1585 (theoretical value: 517.1597).

[0286] Synthesis Example 4: Preparation of Intermediate d-166

[0287] Under a nitrogen atmosphere, e-166 (24.26 g, 60.00 mmol), pinacol diboronate (16.76 g, 66.00 mmol), and potassium acetate (11.78 g, 120.00 mmol) were added sequentially to the reaction flask. Subsequently, 360 mL of DMF was added, and after purging the air three times with nitrogen, 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (Pd(dppf)Cl2) (0.53 g, 0.72 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added to the system, and the mixture was extracted with ethyl acetate (400 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization with n-hexane:ethyl acetate = 8:1 to give product d-166 (21.94 g, 81%); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 451.2712 (theoretical value: 451.2700).

[0288] Synthesis Example 5: Preparation of Intermediate d-241

[0289] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-241 to obtain intermediate d-241 (26.98 g), with an HPLC purity ≥99.82%. Mass spectrometry m / z: 576.3189 (theoretical value: 576.3200).

[0290] Synthesis Example 6: Preparation of Intermediate d-259

[0291] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-259 to obtain intermediate d-259 (21.69 g), with an HPLC purity ≥99.87%. Mass spectrometry m / z: 446.2154 (theoretical value: 446.2166).

[0292] Synthesis Example 7: Preparation of Intermediate c-291

[0293] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-291 to obtain intermediate c-291 (16.39 g), with an HPLC purity of ≥99.85%. Mass spectrometry m / z: 325.1772 (theoretical value: 325.1787).

[0294] Synthesis Example 8: Preparation of Intermediate d-296

[0295] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-296 to obtain intermediate d-296 (25.90 g), with HPLC purity ≥99.79%. Mass spectrometry m / z: 560.2901 (theoretical value: 560.2887).

[0296] Synthesis Example 9: Preparation of Intermediate C-358

[0297] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-358 to obtain intermediate c-358 (16.20 g), with an HPLC purity of ≥99.81%. Mass spectrometry m / z: 325.1802 (theoretical value: 325.1787).

[0298] Synthesis Example 10: Preparation of Intermediate C-467

[0299] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-467 to obtain intermediate c-467 (16.38 g), with an HPLC purity of ≥99.86%. Mass spectrometry m / z: 321.1547 (theoretical value: 321.1536).

[0300] Synthesis Example 11: Preparation of Intermediate d-500

[0301] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-500 to obtain intermediate d-500 (18.83 g), with an HPLC purity of ≥99.84%. Mass spectrometry m / z: 397.2227 (theoretical value: 397.2213).

[0302] Synthesis Example 12: Preparation of Intermediate d-677

[0303] Following the preparation method of Synthesis Example 4, e-166 was replaced with an equimolar amount of e-677 to obtain intermediate d-677 (28.53 g), with an HPLC purity ≥99.87%. Mass spectrometry m / z: 609.2826 (theoretical value: 609.2839).

[0304] Synthesis Example 13: Preparation of Compound 35

[0305] Preparation of intermediate A-35: Under a nitrogen atmosphere, a-35 (28.56 g, 90.00 mmol), b-35 (27.35 g, 99.00 mmol), potassium carbonate (24.88 g, 180.00 mmol), 420 mL toluene, 140 mL ethanol, and 140 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.39 g, 1.20 mmol) was added. The mixture was stirred, and the system was heated under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 5:1 to obtain intermediate A-35 (22.93 g, yield 75%). HPLC analysis showed that the solid purity was ≥99.83%. Mass spectrometry m / z: 337.9884 (theoretical value: 337.9893).

[0306] Preparation of intermediate B-35: Under a nitrogen atmosphere, A-35 (20.38 g, 60.00 mmol), c-35 (26.16 g, 66.00 mmol), potassium carbonate (16.59 g, 120.00 mmol), 400 mL tetrahydrofuran, and 100 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.91 g, 0.78 mmol) was added. The mixture was stirred, and the reaction system was heated under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 8:1 to obtain intermediate B-35 (24.13 g, yield 76%). HPLC analysis showed that the solid purity was ≥99.87%. Mass spectrometry m / z: 528.1796 (theoretical value: 528.1789).

[0307] Preparation of compound 35: Under a nitrogen atmosphere, B-35 (15.87 g, 30.00 mmol), d-35 (15.65 g, 33.00 mmol), potassium carbonate (8.29 g, 60 mmol), P(t-Bu)3 (0.5 M toluene solution) (1.4 mL, 0.70 mmol), and 300 mL of tetrahydrofuran were added to a reaction flask. After purging the air three times with nitrogen, tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.32 g, 0.35 mmol) was added. The mixture was refluxed and stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene to obtain compound 35 (18.67 g, 30.00 mmol). g, yield 74%; HPLC analysis showed solid purity ≥ 99.94%. Mass spectrometry m / z: 840.2982 (theoretical value: 840.2994). Theoretical elemental content (%) C 59 H 44 N₂SSi: C, 84.25; H, 5.27; N, 3.33. Measured elemental content (%): C, 84.22; H, 5.28; N, 3.32.

[0308] Synthesis Example 14: Preparation of Compound 45

[0309] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-45, yielding compound 45 (16.56 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 735.2968 (theoretical value: 735.2957). Theoretical elemental content (%) C 53 H 41 NOSi: C, 86.49; H, 5.62; N, 1.90. Measured elemental content (%): C, 86.51; H, 5.63; N, 1.92.

[0310] Synthesis Example 15: Preparation of Compound 97

[0311] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-97, yielding compound 97 (16.12 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 735.2948 (theoretical value: 735.2957). Theoretical elemental content (%) C 53 H 41NOSi: C, 86.49; H, 5.62; N, 1.90. Measured elemental content (%): C, 86.47; H, 5.61; N, 1.91.

[0312] Synthesis Example 16: Preparation of Compound 103

[0313] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-103 to obtain compound 103 (16.45 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 740.3261 (theoretical value: 740.3271). Theoretical elemental content (%) C 53 H 36 D5NOSi: C, 85.90; H, 6.26; N, 1.89. Measured elemental content (%): C, 85.88; H, 6.27; N, 1.91.

[0314] Synthesis Example 17: Preparation of Compound 166

[0315] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-166, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-166, yielding compound 166 (15.83 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 742.3387 (theoretical value: 742.3397). Theoretical elemental content (%) C 53 H 34 D7NOSi: C, 85.67; H, 6.51; N, 1.89. Measured elemental content (%): C, 85.64; H, 6.53; N, 1.91.

[0316] Synthetic Example 18: Preparation of Compound 175

[0317] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-166, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-175, yielding compound 175 (16.21 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 749.3125 (theoretical value: 749.3114). Theoretical elemental content (%) C 54 H 43NOSi: C, 86.48; H, 5.78; N, 1.87. Measured elemental content (%): C, 86.47; H, 5.76; N, 1.89.

[0318] Synthesis Example 19: Preparation of Compound 241

[0319] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-241 to obtain compound 241 (17.35 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 791.3596 (theoretical value: 791.3583). Theoretical elemental content (%) C 57 H 49 NOSi: C, 86.43; H, 6.24; N, 1.77. Measured elemental content (%): C, 86.45; H, 6.22; N, 1.78.

[0320] Synthesis Example 20: Preparation of Compound 259

[0321] Preparation of compound 259: According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-259, yielding compound 259 (15.72 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 737.2849 (theoretical value: 737.2862). Theoretical elemental content (%) C 51 H 39 N3OSi: C, 83.01; H, 5.33; N, 5.69. Measured elemental content (%): C, 82.98; H, 5.31; N, 5.71.

[0322] Synthesis Example 21: Preparation of Compound 265

[0323] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-265, yielding compound 265 (17.45 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 785.3125 (theoretical value: 785.3114). Theoretical elemental content (%) C57 H 43 NOSi: C, 87.10; H, 5.51; N, 1.78. Measured elemental content (%): C, 87.08; H, 5.53; N, 1.81.

[0324] Synthesis Example 22: Preparation of Compound 288

[0325] According to the preparation method in Synthesis Example 13, c-35 was replaced with an equimolar amount of c-288, and d-35 was replaced with an equimolar amount of d-288 to obtain compound 288 (16.88 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 749.3103 (theoretical value: 749.3114). Theoretical elemental content (%) C 54 H 43 NOSi: C, 86.48; H, 5.78; N, 1.87. Measured elemental content (%): C, 86.51; H, 5.77; N, 1.89.

[0326] Synthesis Example 23: Preparation of Compound 291

[0327] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-291, and d-35 was replaced with an equimolar amount of d-45, yielding compound 291 (17.09 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 739.3196 (theoretical value: 739.3208). Theoretical elemental content (%) C 53 H 37 D4NOSi: C, 86.02; H, 6.13; N, 1.89. Measured elemental content (%): C, 86.04; H, 6.14; N, 1.92.

[0328] Synthesis Example 24: Preparation of Compound 296

[0329] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-296, and d-35 was replaced with an equimolar amount of d-296, yielding compound 296 (16.32 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 776.3231 (theoretical value: 776.3223). Theoretical elemental content (%) C 55 H44 N₂OSi: C, 85.01; H, 5.71; N, 3.61. Measured elemental content (%): C, 84.98; H, 5.69; N, 3.63.

[0330] Synthesis Example 25: Preparation of Compound 358

[0331] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-358, and d-35 was replaced with an equimolar amount of d-358, yielding compound 358 (16.43 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 739.3221 (theoretical value: 739.3208). Theoretical elemental content (%) C 53 H 37 D4NOSi: C, 86.02; H, 6.13; N, 1.89. Measured elemental content (%): C, 86.04; H, 6.11; N, 1.92.

[0332] Synthesis Example 26: Preparation of Compound 396

[0333] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-396, yielding compound 396 (16.07 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 733.2795 (theoretical value: 733.2801). Theoretical elemental content (%) C 53 H 39 NOSi: C, 86.73; H, 5.36; N, 1.91. Measured elemental content (%): C, 86.72; H, 5.34; N, 1.93.

[0334] Synthesis Example 27: Preparation of Compound 398

[0335] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-166, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-396, yielding compound 398 (15.63 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 733.2813 (theoretical value: 733.2801). Theoretical elemental content (%) C 53 H39 NOSi: C, 86.73; H, 5.36; N, 1.91. Measured elemental content (%): C, 86.75; H, 5.35; N, 1.92.

[0336] Synthesis Example 28: Preparation of Compound 421

[0337] According to the preparation method in Synthesis Example 13, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-421 to obtain compound 421 (17.74 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 809.3128 (theoretical value: 809.3114). Theoretical elemental content (%) C 59 H 43 NOSi: C, 87.48; H, 5.35; N, 1.73. Measured elemental content (%): C, 87.45; H, 5.34; N, 1.75.

[0338] Synthesis Example 29: Preparation of Compound 422

[0339] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-422, and d-35 was replaced with an equimolar amount of d-396, yielding compound 422 (17.25 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 809.3123 (theoretical value: 809.3114). Theoretical elemental content (%) C 59 H 43 NOSi: C, 87.48; H, 5.35; N, 1.73. Measured elemental content (%): C, 87.49; H, 5.33; N, 1.71.

[0340] Synthesis Example 30: Preparation of Compound 423

[0341] According to the preparation method in Synthesis Example 13, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-423 to obtain compound 423 (16.46 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 783.2944 (theoretical value: 783.2957). Theoretical elemental content (%) C 57 H 41NOSi: C, 87.32; H, 5.27; N, 1.79. Measured elemental content (%): C, 87.34; H, 5.29; N, 1.81.

[0342] Synthesis Example 31: Preparation of Compound 436

[0343] According to the preparation method in Synthesis Example 13, b-35 was replaced with an equimolar amount of b-436, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-436, yielding compound 436 (17.66 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 805.3184 (theoretical value: 805.3196). Theoretical elemental content (%) C 56 H 47 NOSi2: C, 83.43; H, 5.88; N, 1.74. Measured elemental content (%): C, 83.41; H, 5.89; N, 1.76.

[0344] Synthesis Example 32: Preparation of Compound 438

[0345] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-396, yielding compound 438 (14.61 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 657.2502 (theoretical value: 657.2489). Theoretical elemental content (%) C 47 H 35 NOSi: C, 85.81; H, 5.36; N, 2.13. Measured elemental content (%): C, 85.79; H, 5.37; N, 2.11.

[0346] Synthesis Example 33: Preparation of Compound 445

[0347] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-445, yielding compound 445 (17.52 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 845.4039 (theoretical value: 845.4053). Theoretical elemental content (%) C 61 H 55NOSi: C, 86.58; H, 6.55; N, 1.66. Measured elemental content (%): C, 86.59; H, 6.57; N, 1.64.

[0348] Synthesis Example 34: Preparation of Compound 462

[0349] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-462, yielding compound 462 (18.34 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 814.3414 (theoretical value: 814.3428). Theoretical elemental content (%) C 59 H 38 D5NOSi: C, 86.94; H, 5.93; N, 1.72. Measured elemental content (%): C, 86.96; H, 5.91; N, 1.69.

[0350] Synthesis Example 35: Preparation of Compound 465

[0351] According to the preparation method in Synthesis Example 13, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-465 to obtain compound 465 (15.01 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 735.2723 (theoretical value: 735.2706). Theoretical elemental content (%) C 51 H 37 N3OSi: C, 83.23; H, 5.07; N, 5.71. Measured elemental content (%): C, 83.24; H, 5.09; N, 5.69.

[0352] Synthesis Example 36: Preparation of Compound 467

[0353] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-467, and d-35 was replaced with an equimolar amount of d-396, yielding compound 467 (16.07 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 733.2812 (theoretical value: 733.2801). Theoretical elemental content (%) C 53 H 39NOSi: C, 86.73; H, 5.36; N, 1.91. Measured elemental content (%): C, 86.70; H, 5.38; N, 1.89.

[0354] Synthesis Example 37: Preparation of Compound 481

[0355] According to the preparation method in Synthesis Example 13, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-481 to obtain compound 481 (13.77 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 611.2653 (theoretical value: 611.2644). Theoretical elemental content (%) C 43 H 37 NOSi: C, 84.41; H, 6.10; N, 2.29. Measured elemental content (%): C, 84.39; H, 6.13; N, 2.32.

[0356] Synthesis Example 38: Preparation of Compound 486

[0357] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-486, yielding compound 486 (13.40 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 611.2629 (theoretical value: 611.2644). Theoretical elemental content (%) C 43 H 37 NOSi: C, 84.41; H, 6.10; N, 2.29. Measured elemental content (%): C, 84.43; H, 6.08; N, 2.28.

[0358] Synthesis Example 39: Preparation of Compound 500

[0359] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-500, and d-35 was replaced with an equimolar amount of d-500, yielding compound 500 (14.99 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 693.3231 (theoretical value: 693.3224). Theoretical elemental content (%) C 48 H 35D5N2OSi: C, 83.08; H, 6.53; N, 4.04. Measured elemental content (%): C, 83.07; H, 6.55; N, 4.02

[0360] Synthesis Example 40: Preparation of Compound 567

[0361] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-567, yielding compound 567 (16.78 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 735.2969 (theoretical value: 735.2957). Theoretical elemental content (%) C 53 H 41 NOSi: C, 86.49; H, 5.62; N, 1.90. Measured elemental content (%): C, 86.51; H, 5.59; N, 1.91.

[0362] Synthetic Example 41: Preparation of Compound 634

[0363] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-634, yielding compound 634 (16.65 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 749.2737 (theoretical value: 749.2750). Theoretical elemental content (%) C 53 H 39 NO2Si: C, 84.88; H, 5.24; N, 1.87. Measured elemental content (%): C, 84.86; H, 5.25; N, 1.89.

[0364] Synthesis Example 42: Preparation of Compound 639

[0365] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-166, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-639, yielding compound 639 (16.20 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 749.2761 (theoretical value: 749.2750). Theoretical elemental content (%) C 53 H 39NO2Si: C, 84.88; H, 5.24; N, 1.87. Measured elemental content (%): C, 84.91; H, 5.25; N, 1.84.

[0366] Synthesis Example 43: Preparation of Compound 640

[0367] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-640, yielding compound 640 (15.97 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 749.2737 (theoretical value: 749.2750). Theoretical elemental content (%) C 53 H 39 NO2Si: C, 84.88; H, 5.24; N, 1.87. Measured elemental content (%): C, 84.90; H, 5.26; N, 1.88.

[0368] Synthesis Example 44: Preparation of Compound 651

[0369] According to the preparation method in Synthesis Example 13, b-35 was replaced with an equimolar amount of b-651, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-634, yielding compound 651 (15.75 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 749.2763 (theoretical value: 749.2750). Theoretical elemental content (%) C 53 H 39 NO2Si: C, 84.88; H, 5.24; N, 1.87. Measured elemental content (%): C, 84.85; H, 5.22; N, 1.89.

[0370] Synthesis Example 45: Preparation of Compound 664

[0371] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-664, c-35 was replaced with an equimolar amount of c-664, and d-35 was replaced with an equimolar amount of d-634, yielding compound 664 (17.68 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 841.2846 (theoretical value: 841.2835). Theoretical elemental content (%) C 59 H 43NOSSi: C, 84.15; H, 5.15; N, 1.66. Measured elemental content (%): C, 84.13; H, 5.14; N, 1.65.

[0372] Synthesis Example 46: Preparation of Compound 672

[0373] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-672, yielding compound 672 (16.76 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 775.3259 (theoretical value: 775.3270). Theoretical elemental content (%) C 56 H 45 NOSi: C, 86.67; H, 5.84; N, 1.80. Measured elemental content (%): C, 86.66; H, 5.82; N, 1.79.

[0374] Synthesis Example 47: Preparation of Compound 677

[0375] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-97, and d-35 was replaced with an equimolar amount of d-677, yielding compound 677 (18.07 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 824.3236 (theoretical value: 824.3223). Theoretical elemental content (%) C 59 H 44 N₂OSi: C, 85.89; H, 5.38; N, 3.40. Measured elemental content (%): C, 85.91; H, 5.37; N, 3.42.

[0376] Synthesis Example 48: Preparation of Compound 693

[0377] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-265, c-35 was replaced with an equimolar amount of c-693, and d-35 was replaced with an equimolar amount of d-693, yielding compound 693 (14.30 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 652.2919 (theoretical value: 652.2910). Theoretical elemental content (%) C 45 H 40N₂OSi: C, 82.78; H, 6.18; N, 4.29. Measured elemental content (%): C, 82.76; H, 6.16; N, 4.32.

[0378] Synthesis Example 49: Preparation of Compound 696

[0379] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-45, and d-35 was replaced with an equimolar amount of d-696, yielding compound 696 (14.57 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 703.3256 (theoretical value: 703.3270). Theoretical elemental content (%) C 50 H 45 NOSi: C, 85.31; H, 6.44; N, 1.99. Measured elemental content (%): C, 85.29; H, 6.45; N, 2.02.

[0380] Synthesis Example 50: Preparation of Compound 816

[0381] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-816, and d-35 was replaced with an equimolar amount of d-816, yielding compound 816 (17.04 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 799.2721 (theoretical value: 799.2729). Theoretical elemental content (%) C 57 H 41 NSSi: C, 85.57; H, 5.17; N, 1.75. Measured elemental content (%): C, 85.55; H, 5.19; N, 1.76.

[0382] Synthesis Example 51: Preparation of Compound 950

[0383] According to the preparation method in Synthesis Example 13, a-35 was replaced with an equimolar amount of a-45, c-35 was replaced with an equimolar amount of c-950, and d-35 was replaced with an equimolar amount of d-950, yielding compound 950 (17.77 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 833.3105 (theoretical value: 833.3114). Theoretical elemental content (%) C 61 H 43NOSi: C, 87.84; H, 5.20; N, 1.68. Measured elemental content (%): C, 87.86; H, 5.19; N, 1.65.

[0384] Synthesis Example 52: Preparation of Compound 1020

[0385] Preparation of intermediate B-1020: Under a nitrogen atmosphere, A-1020 (15.82 g, 60.00 mmol), c-1020 (19.48 g, 66.00 mmol), potassium carbonate (16.59 g, 120.00 mmol), 400 mL tetrahydrofuran, and 100 mL water were added sequentially to a reaction flask. After purging the air three times with nitrogen, tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.91 g, 0.78 mmol) was added. The mixture was stirred, and the reaction system was heated under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 8:1 to obtain intermediate B-1020 (15.41 g, yield 73%). HPLC analysis showed that the solid purity was ≥99.86%. Mass spectrometry m / z: 351.0835 (theoretical value: 351.0846).

[0386] Preparation of compound 1020: Under a nitrogen atmosphere, B-1020 (10.56 g, 30.00 mmol), d-1020 (15.59 g, 33.00 mmol), potassium carbonate (8.29 g, 60 mmol), P(t-Bu)3 (0.5 M toluene solution) (1.4 mL, 0.70 mmol), and 300 mL of tetrahydrofuran were added to a reaction flask. After purging the air three times with nitrogen, tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.32 g, 0.35 mmol) was added. The mixture was refluxed and stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain compound 1020 (14.89 g, 14.80 mmol). g, yield 75%); HPLC analysis showed solid purity ≥ 99.95%. Mass spectrometry m / z: 661.2814 (theoretical value: 661.2801). Theoretical elemental content (%) C 47 H 39 NOSi: C, 85.28; H, 5.94; N, 2.12. Measured elemental content (%): C, 85.29; H, 5.96; N, 2.11.

[0387] Device Examples

[0388] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO / Ag / ITO glass substrate used in the device fabrication examples was purchased commercially.

[0389] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter, to test the driving voltage and luminous efficiency of the organic electroluminescent device. Using a McScience M6000 OLED lifetime testing system, the lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature, with a current density of 10 mA / cm². 2 .

[0390] Device Example 1: Fabrication of a Red Organic Light Emitting Device

[0391] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned with acetone, methanol and isopropanol for 20 minutes each in sequence. After that, it is treated with ultraviolet-ozone for 30 minutes. Finally, the substrate is placed in a vacuum evaporation equipment for later use.

[0392] The following layers were deposited sequentially on the aforementioned ITO / Ag / ITO glass substrate: a. HT-1 and PD-1 (mass ratio 97:3) as a hole injection layer, with a deposition thickness of 15 nm. b. HT-1 as a hole transport layer, with a deposition thickness of 80 nm. c. HT-2 as an electron blocking layer, with a deposition thickness of 70 nm. d. RH-1 as the first host material, RH-2 as the second host material, and RD-1 as the guest material (mass ratio 48:48:4), with a light-emitting layer thickness of 35 nm. e. Compound 35 and Liq (mass ratio 1:1) as an electron transport layer, with a deposition thickness of 30 nm. f. LiF layer as an electron injection layer, with a deposition thickness of 1 nm. g. Mg and Ag in a mass ratio of 1:9, with a deposition thickness of 15 nm. h. CP-1 as a capping layer, with a deposition thickness of 80 nm.

[0393]

[0394]

[0395]

[0396] Device Examples 2-40: Fabrication of Red Organic Light Emitting Devices

[0397] Organic electroluminescent devices were prepared by replacing compound 35 in Device Example 1 with compounds 45, 97, 103, 166, 175, 241, 259, 265, 288, 291, 296, 358, 396, 398, 421, 422, 423, 436, 438, 445, 462, 465, 467, 481, 486, 500, 567, 634, 639, 640, 651, 664, 672, 677, 693, 696, 816, 950, and 1020 as the electron transport layer, while maintaining the same fabrication process.

[0398] Comparative Device Examples 1-3: Fabrication of Red Organic Light Emitting Devices

[0399] Organic electroluminescent devices were fabricated by replacing compound 35 in device example 1 with R-1, R-2, and R-3 as the electron transport layer, while keeping the rest of the fabrication process exactly the same.

[0400] Table 1: Test data on the luminescence characteristics of organic electroluminescent devices prepared in Device Examples 1-40 and Comparative Device Examples 1-3

[0401]

[0402] As shown in Table 1, the fluorene compounds described in this invention have high electron mobility. When used as electron transport layer materials for organic electroluminescent devices, they can reduce the electron injection transport barrier and drive voltage, and improve the binding efficiency of holes and electrons, thereby enhancing the luminous efficiency and lifetime of organic electroluminescent devices.

[0403] Device Example 41: Fabrication of a Green Organic Light Emitting Device

[0404] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned with acetone, methanol and isopropanol for 20 minutes each in sequence. After that, it is treated with ultraviolet-ozone for 30 minutes. Finally, the substrate is placed in a vacuum evaporation equipment for later use.

[0405] The following layers were deposited sequentially on the aforementioned ITO / Ag / ITO glass substrate: a. HT-1 and PD-1 (mass ratio 97:3) as a hole injection layer, with a deposition thickness of 15 nm. b. HT-1 as a hole transport layer, with a deposition thickness of 80 nm. c. HT-3 as an electron blocking layer, with a deposition thickness of 35 nm. d. GH-1 as the first host material, GH-2 as the second host material, and GD-1 as the guest material (mass ratio 47:47:6), with a light-emitting layer thickness of 35 nm. e. Compound 35 as a hole blocking layer, with a deposition thickness of 10 nm. f. ET-1 and Liq (mass ratio 1:1) as an electron transport layer, with a deposition thickness of 30 nm. g. LiF layer as an electron injection layer, with a deposition thickness of 1 nm. h. Mg and Ag with a mass ratio of 1:9, with a deposition thickness of 15 nm. i. CP-1 is used as a capping layer, and the thickness of the vapor-deposited film is 65 nm.

[0406]

[0407]

[0408]

[0409] Device Examples 42-80: Fabrication of Green Organic Light Emitting Devices

[0410] Organic electroluminescent devices were prepared by replacing compound 35 in device example 41 with compounds 45, 97, 103, 166, 175, 241, 259, 265, 288, 291, 296, 358, 396, 398, 421, 422, 423, 436, 438, 445, 462, 465, 467, 481, 486, 500, 567, 634, 639, 640, 651, 664, 672, 677, 693, 696, 816, 950, and 1020 as hole blocking layers, while maintaining the same fabrication process.

[0411] Comparative Device Examples 4-6: Fabrication of Green Organic Light Emitting Devices

[0412] Organic electroluminescent devices were fabricated by replacing compound 35 in device example 41 with R-4, R-5, and R-6 as hole blocking layers, while keeping the rest of the fabrication process exactly the same.

[0413] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 41-80 and Comparative Device Examples 4-6

[0414]

[0415] As shown in Table 2, the fluorene compounds described in this invention can effectively block holes from migrating to the electron transport layer, reduce the electron injection transport barrier, lower the driving voltage, avoid excessive local voltage leading to increased device power consumption, extend device lifespan, and improve luminous efficiency.

[0416] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A fluorene compound, characterized in that, The fluorene compounds have the following structures; In Formula I, L is selected from any one of substituted C6-C30 arylene, substituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, and substituted C6-C30 heteroarylene. At least one of the "substituted" groups in L is selected from the group of formula II, and the remainder is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C4-C30 heteroaryl group and combination thereof; The L2 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring, substituted or unsubstituted C2-C30 heteroarylene, and combinations thereof. The L3 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group and combination thereof; Ar1 is selected from formula III-1 or formula III-2. When Ar1 is selected from formula III-2, L3 is not selected from single bonds. X is selected from O, S, N(R) c Any one of the following; The v and a may be the same or different from each other, and are independently selected from CH or N atoms. When v and a are bonded to other groups, the v and a are selected from C atoms. The R a R b R1 and R2 may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; or R2 may be the same as or different from each other, and are independently selected from any one of the following: hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C30 alkyl, substituted or unsubstituted ... alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, substituted alkyl, a R b They can connect to each other to form substituted or unsubstituted rings; or R a R b Either of them can be directly bonded to L1; The R c It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The Rs may be the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; The n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When there are two or more R1s, the two or more R1s are the same or different from each other; or two adjacent R1s can be connected to each other to form substituted or unsubstituted rings. The m is selected from 0, 1, 2, 3 or 4. When there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s can be connected to each other to form substituted or unsubstituted benzene rings, pyridine rings or pyrimidine rings.

2. The fluorene compound according to claim 1, characterized in that, The Selected from any one of the following groups; The v may be the same as or different from each other, and are independently selected from CH or N atoms. When v is bonded to other groups, the v is selected from C atoms. The Y is selected from O, S, C(R) x R y ), N(R z Any one of the following; The ring A is selected from substituted or unsubstituted C3~C12 aliphatic rings; The R a R b R1 may be the same as or different from each other, and is independently selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1~C20 alkyl, substituted or unsubstituted C2~C20 alkenyl, substituted or unsubstituted C3~C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aromatic ring and C3~C20 aliphatic ring fused ring group, substituted or unsubstituted C2~C30 heteroaryl; a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The R x R y They may be identical or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R x R y They can connect with each other to form substituted or unsubstituted rings; The R z Selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused-ring group of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R z It can be directly bonded to L1; The L a It is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, and combinations thereof.

3. The fluorene compound according to claim 1, characterized in that, The Selected from any one of the following groups; ； R1 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrimidinyl, etc. Azinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl, or indoleyl; or two adjacent R1 groups forming a substituted or unsubstituted benzene ring or naphthyl ring; The number b1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the number b2 is selected from 0, 1, 2, 3, or 4; the number b3 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the number b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the number b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the number b8 is selected from 0, 1, or 2; the number b9 is selected from 0, 1, 2, 3, 4, or 5; the number b... 10 The value b is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, wherein b 12 Choose from 0, 1, 2, or 3.

4. The fluorene compound according to claim 1, characterized in that, Formula II is selected from any one of the following groups; 。 5. The fluorene compound according to claim 1, characterized in that, The Ar1 formula is selected from any one of the following groups; X is selected from O, S, N(R) c Any one of the following; The R2 is selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl. , pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl or indoleyl, or two adjacent R2s connected to form a substituted or unsubstituted benzene ring, pyridine ring or pyrimidine ring; The R c Selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrimidinyl The following are listed: pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiophene, or indoleyl. c1 is selected from 0, 1, 2, 3 or 4, c2 is selected from 0, 1, 2 or 3, and c3 is selected from 0, 1 or 2.

6. The fluorene compound according to claim 1, characterized in that, The L2 is selected from a single bond or any of the following groups; The y and t1 may be the same or different from each other, and are independently selected from C(R4) or N atoms. When y is bonded to other groups, the y is selected from C atoms. The t2 is selected from O, S, N(R) d Any one of the following; The t3 is selected from O, S, N(R) d ), C(R e Any one of 2; The R d It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; The R4, R e They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C20 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl. When two or more R4s are present, the two or more R4s may be the same as or different from each other, or two adjacent R4s may be connected to each other to form substituted or unsubstituted rings. The d1 is selected from 0 or 1.

7. The fluorene compound according to claim 1, characterized in that, The L is selected from any one of the following groups; At least one R6 in each group is selected from a group of formula II, and the remaining R6 are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, or C3-C12 cycloalkyl groups, as shown below: methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, etc. Norborneol alkyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, fluorenyl, carbazoleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, benzothiopheneyl or indoleyl; h1 is selected from 0, 1, 2, 3 or 4; h2 is selected from 0, 1, 2, 3, 4, 5 or 6; h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; h4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; h5 is selected from 0, 1, 2, 3, 4 or 5; h6 is selected from 0, 1, 2 or 3; h7 is selected from 0, 1 or 2; and h8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

8. The fluorene compound according to claim 1, characterized in that, The fluorene compounds are selected from any one of the structures shown below; 。 9. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, an organic layer, and a cathode. The organic layer is located between the anode and the cathode or outside either the anode or the cathode. The organic layer contains at least one of the fluorene compounds as described in any one of claims 1-8.

10. An organic electroluminescent device according to claim 9, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the fluorene compounds according to any one of claims 1-8.

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