Fluorene compound and organic electroluminescent device thereof

Abstract

The invention provides a fluorene compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. When the fluorene compound is used as an electron transport material, the transport rate of electrons in a device can be improved, and the hole and electron recombination probability is improved, so that the luminous efficiency of the device is improved, and the service life of the device is prolonged; when the compound is used as a hole blocking material, electrons can be promoted to be effectively injected into a light-emitting layer, a certain blocking effect on holes is achieved, the light-emitting efficiency of a device can be effectively improved, and the service life of the device is prolonged. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of panel display, lighting sources, organic thin film transistors and the like and has good application effects and industrialization prospects.

Description

Technical Field

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

[0002] With the rapid development of science and technology, emerging industries such as new energy, new materials, information technology, and biotechnology have rapidly emerged, profoundly changing people's work and lives. Organic light-emitting diodes (OLEDs), based on information technology and new materials, are now widely used in small and medium-sized displays such as mobile phone screens and data meters. At the same time, large-scale full-color flat-panel display technology is also gradually maturing. OLEDs have undoubtedly become a strong competitor to second-generation liquid crystal displays (LCDs), and we believe that OLEDs will capture a larger and larger market share in the future.

[0003] Organic electroluminescence is a low-voltage, high-current injection-type luminescence. Because it has the properties of a light-emitting diode, it is often called an organic light-emitting diode (OLED). The luminescence mechanism is as follows: under the drive of an external voltage, electrons enter the electron transport layer from the cathode, and holes enter the hole transport layer from the anode. The two recombine in the light-emitting layer to produce excitons, which then radiatively transition back to the ground state and emit light. The luminescence process can be summarized as the following four steps: (1) injection of carriers; (2) transport of carriers in the organic layer; (3) recombination of positive and negative charge carriers to form excitons; and (4) radiative transition of excitons to emit light.

[0004] Based on the device structure, organic electroluminescent materials can be broadly categorized as follows: electrode materials, electrode modification materials, hole and electron transport materials, and luminescent materials. Electron transport materials inject electrons and balance carriers. They possess appropriate LUMO and HOMO energy levels to reduce the injection barrier and operating voltage. Their high electron mobility directs carrier recombination away from the cathode, increasing the exciton generation rate. The hole blocking layer, located between the electron transport layer and the luminescent layer, possesses hole-blocking capabilities, blocking holes from the anode at the interface of the device's luminescent layer. This increases the probability of electron-hole recombination at the interface, thereby enhancing the device's luminous efficiency.

[0005] However, most of the electron transport layer materials currently used do not have good electron mobility, which makes it difficult to improve the luminous efficiency of the device; the hole blocking material cannot effectively lower the energy level barrier and block hole transport; the charge generation layer material cannot effectively connect the light-emitting layers in series, resulting in device loss and affecting the device's luminous efficiency and service life.

[0006] Therefore, in view of the current application requirements for each functional layer and the optoelectronic characteristics of the device, it is necessary to select more suitable electron transport materials, hole blocking materials, and charge generation layer materials with higher performance to achieve the comprehensive characteristics of high efficiency, long life and low voltage of the device. Summary of the Invention

[0007] In order to solve the above problems, the present invention aims to provide a fluorene compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and extend the service life of the device.

[0008] The present invention provides a fluorene compound having a structure represented by Formula I:

[0009]

[0010] Wherein, said z is independently selected from any one of CH and N;

[0011] The x is independently selected from C(R n ), any one of N, and at least one of the x is selected from N;

[0012] The m is selected from 0 or 1; the n is selected from 0 or 1; and the m and n are not selected from 0 or 1 at the same time;

[0013] The R1, R2, R3, R n independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, and at least one of R1, R2, and R3 is selected from Formula II;

[0014]

[0015] The R x Any one independently selected from substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0016] Said q is selected from 1, 2, 3, 4 or 5;

[0017] The a is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring;

[0018] The b is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;

[0019] The L is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0020]

[0021] The u is independently selected from any one of CH and N;

[0022] Said Y1 and Y2 are independently selected from O, S, N (R u )

[0023] Said Y3 is selected from O, S, N (R u )

[0024] Said Y4 and Y5 are independently selected from O, S, C(R m R t )、N(R u )

[0025] The ring C is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0026] The R g 、R g 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C11 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C11 heteroaromatic ring;

[0027] The R m 、R tindependently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R m 、R t are connected to form a substituted or unsubstituted ring;

[0028] The R u Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0029] The h is selected from 1, 2, 3 or 4;

[0030] 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 or 2; when there are two or more R g When two or more R g The same or different from each other, or two adjacent R g are connected to each other to form a substituted or unsubstituted ring;

[0031] The g'1 is selected from 0, 1 or 2; when there are two or more R g ', two or more R g 'same or different from each other;

[0032] The Ar1 and Ar2 are independently selected from any one of the following groups:

[0033]

[0034] The v is independently selected from any one of CH and N;

[0035] The y is independently selected from any one of CH and N, and at least two of the y are selected from N;

[0036] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0037] Said X1 and X2 are independently selected from O, S, N (R v )

[0038] Said X3 is selected from S, C(Rp R q )、N(R z )

[0039] Said X4 and X5 are independently selected from O, S, C(R p R q )、N(R z )

[0040] The R c 、R c 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring;

[0041] The R c " is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C1-C25 heterocycloalkyl;

[0042] The R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring;

[0043] The R v 、R z Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0044] Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3 or 4; said c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c5 is selected from 0, 1 or 2; said c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said c7 is selected from 0, 1, 2 or 3; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0045] The c'0 is selected from 0 or 1; the c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; when there are two or more R c ', two or more R c 'same or different from each other;

[0046] The c"1 is selected from 0, 1, 2 or 3; the c"2 is selected from 0, 1, 2, 3 or 4; the c"3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R c ", two or more R c ” are the same as or different from each other;

[0047] The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused sub-cyclic group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused sub-cyclic group;

[0048] It does not contain the following compounds:

[0049]

[0050] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, wherein the organic layer comprises at least one of the fluorene compounds described in the present invention.

[0051] Beneficial effects

[0052] The present invention provides a fluorene compound, which has the function of transmitting electrons. When used as an electron transport material, it can increase the transmission rate of electrons in a device, balance the transmission efficiency of holes and electrons, increase the probability of hole and electron recombination, thereby improving the luminous efficiency of the device and extending the service life of the device; when used as a hole-blocking material, the compound can reduce the energy level barrier, promote the effective injection of electrons into the light-emitting layer, and has a certain blocking effect on holes, which can effectively improve the luminous efficiency of the device and extend the service life of the device. The preparation method of the compound provided by the present invention is simple, the raw materials are easily available, can meet industrialization needs, and has good industrialization prospects. DETAILED DESCRIPTION

[0053] The following is a clear and complete description of the technical solutions of the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, rather than all the embodiments. After reading this invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the present invention.

[0054] In the present specification, "-*" means a portion connected to another substituent. "-*" can be connected to any optional position of the group / fragment to which it is connected.

[0055] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the rings. For example, Can represent Can represent And so on.

[0056] In the present specification, when the position of a substituent or a bonding site on a ring is not fixed, it means that it can be bonded to any of the optional sites of the ring.

[0057] For example, Can represent Can represent Can represent And so on.

[0058] The term "linked to form a ring" as used herein refers to two groups being linked to each other via a chemical bond and optionally aromatized. For example:

[0059]

[0060] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0061] Examples of the halogen atom according to the present invention may include fluorine, chlorine, bromine and iodine.

[0062] The alkyl group described in the present invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from an alkane molecule, and can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. 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, dodecyl, etc.; the branched-chain alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc.

[0063] The cycloalkyl group herein refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and bornyl.

[0064] The heterocycloalkyl group of the present invention refers to a group formed by removing a hydrogen atom from a heterocyclic molecule whose ring atoms contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, O, S, N, Si, or P atoms. The group preferably has 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. The heterocycloalkyl group includes, but is not limited to, piperidinyl, piperazinyl, tetrahydropyrrolyl, oxiranyl, thiothioranyl, morpholinyl, and thiomorpholinyl.

[0065] The "substituted or unsubstituted silyl group" described in the present invention refers to a -Si(R)3 group, wherein each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring. Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, or substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, phenyl, biphenyl, or naphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-tert-butylsilyl, tricyclopentanylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.

[0066] The aryl group described in the present invention refers to the general term for a monovalent group obtained by removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. It can be a monocyclic aryl group, a polycyclic aryl group or a condensed aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group having only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, quaterphenyl, etc., but not limited thereto; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, such as naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, 9,9'-spirobifluorenyl, etc., but are not limited thereto.

[0067] The heteroaryl group described in the present invention refers to a general term for a group obtained after one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom. It can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed ring heteroaryl group, and the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon, and phosphorus atoms. It preferably has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the condensed ring heteroaryl group may include quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzo Quinoxalinyl, o-phenanthrolinyl, naphthyridinyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthryl, spirofluorenylthioanthryl, etc., but are not limited thereto.

[0068] The arylene group described in the present invention refers to the general term for a divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group, or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes, but is not limited to, a phenylene group; the polycyclic arylene group includes, but is not limited to, a biphenylene group, a terphenylene group, and the like; specific examples may include, but are not limited to, a naphthylene group, an anthrylene group, a phenanthrenyl group, a pyrenyl group, a triphenylene group, a fluoranthenyl group, and the like.

[0069] The heteroarylene group described in the present invention is a general term for groups obtained by replacing one or more aromatic carbon atoms in an arylene group with heteroatoms, wherein the heteroatoms include but are not limited to O, S, N, Si, or P atoms. Preferably, the group has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. Specific examples of the monocyclic and condensed-ring heteroarylene groups include, but are not limited to, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, and dibenzocarbazolylene. Specific examples of the polycyclic heteroarylene groups include, but are not limited to, bipyridylene, bipyrimidylene, and phenylpyridylene.

[0070] The fused alicyclic and aromatic ring radical described herein is a general term for a monovalent group formed by condensing an alicyclic ring with an aromatic ring and removing one hydrogen atom. Preferably, the fused alicyclic and aromatic ring radical has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused alicyclic and aromatic ring radical may include, but is not limited to, benzocyclopropanyl, benzocyclobutanyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, and benzocycloheptenyl.

[0071] The sub-fused cyclic group of the alicyclic ring and the aromatic ring described in the present invention refers to the general term for the divalent group obtained after the alicyclic ring and the aromatic ring are fused together and two hydrogen atoms are removed. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused cyclic group of the alicyclic ring and the heteroaromatic ring may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptanyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopent ...propyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocycloheptanyl, dibenzofuranocyclopropyl, dibenzofurano cyclopentyl, dibenzofuranyl, dibenzofuranylcyclopentyl, dibenzofuranylcyclohexyl, dibenzofuranylcycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, carbazolylcyclopropyl, carbazolylcyclobutyl, carbazolylcyclopentyl, carbazolylcyclohexyl, carbazolylcycloheptyl, etc., but are not limited thereto.

[0072] The fused ring group of a heterocycloalkane and an aromatic ring of the present invention refers to a general term for a monovalent group obtained by condensing a heterocycloalkane and an aromatic ring and removing one hydrogen atom. Preferably, the fused ring group has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused ring group of a heterocycloalkane and an aromatic ring may include benzopyrrolyl, naphthopyrrolyl, phenanthropyrrolyl, benzazetidinyl, benzazepanyl, benzopiperidinyl, naphthopiperidinyl, phenanthropiperidinyl, etc., but is not limited thereto.

[0073] The fused ring group of an alicyclic ring and a heteroaromatic ring of the present invention refers to a general term for a monovalent group obtained by removing a hydrogen atom after an alicyclic ring and a heteroaromatic ring are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. The fused ring group of an alicyclic ring and a heteroaromatic ring may include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, carbazolylcyclopropyl, carbazolylcyclobutyl, carbazolylcyclopentyl, carbazolylcyclohexyl, carbazolylcycloheptyl, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, and the like, but are not limited thereto.

[0074] The sub-condensed cyclic group of the alicyclic ring and heteroaromatic ring described in the present invention refers to the general term for a divalent group obtained by removing two hydrogen atoms after the alicyclic ring and the heteroaromatic ring are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. The sub-condensed cyclic group of the alicyclic ring and heteroaromatic ring may include dibenzofuranocyclopropylidene, dibenzofuranocyclobutylidene, dibenzofuranocyclopentylidene, dibenzofuranocyclohexylidene, dibenzofuranocycloheptylidene, dibenzothienocyclopropylidene, dibenzothienocyclobutylidene, dibenzothieno ...hexylidene, dibenzofuranocyclohexylidene, dibenzothienocyclohexylidene, dibenzothienocyclohexylidene, dibenzothienocyclopentylidene, dibenzofuranocyclohexylidene, dibenzofuranocyclohexylidene, dibenzothienocyclohexylidene, dibenzothienocyclohexylidene, dibenzothienocyclohexylidene, dibenzothienocyclohexylidene, dibenzoth Thienocyclohexyl, dibenzothienocycloheptyl, carbazolylcyclopropyl, carbazolylcyclobutyl, carbazolylcyclopentyl, carbazolylcyclohexyl, carbazolylcycloheptyl, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, etc., but not limited to these.

[0075] The substituents in the "substituted or unsubstituted" of the present invention can be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, etc., but are not limited thereto, or two adjacent substituents can be connected to form a ring. Deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C12 alkoxy, and specific examples include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, perylene, pyrenyl, fluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9 ,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazolindolyl, pyrrolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, benzocyclobutane, benzocyclobutene, benzocyclopentane, benzocyclopentene, benzocyclohexane, benzocyclohexene, etc., but are not limited thereto. When there are multiple substituents, the multiple substituents may be the same as or different from each other; or adjacent substituents may be connected to form a ring.

[0076] In the present invention, the term "at least one" includes one, two, three, four or more. The term "two or more" includes two, three, four or more, where permitted.

[0077] The present invention provides a fluorene compound, wherein the fluorene compound is selected from the structure represented by formula I:

[0078]

[0079] Wherein, said z is independently selected from any one of CH and N;

[0080] The x is independently selected from C(Rn ), any one of N, and at least one of the x is selected from N;

[0081] The m is selected from 0 or 1; the n is selected from 0 or 1; and the m and n are not selected from 0 or 1 at the same time;

[0082] The R1, R2, R3, R n independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, and at least one of R1, R2, and R3 is selected from Formula II;

[0083]

[0084] The R x Any one independently selected from substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0085] Said q is selected from 1, 2, 3, 4 or 5;

[0086] The a is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring;

[0087] The b is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;

[0088] The L is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0089]

[0090] The u is independently selected from any one of CH and N;

[0091] Said Y1 and Y2 are independently selected from O, S, N (R u )

[0092] Said Y3 is selected from O, S, N (R u )

[0093] Said Y4 and Y5 are independently selected from O, S, C(R m R t )、N(R u )

[0094] The ring C is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0095] The R g 、R g 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C11 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C11 heteroaromatic ring;

[0096] The R m 、R t independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R m 、R t are connected to form a substituted or unsubstituted ring;

[0097] The R u Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0098] The h is selected from 1, 2, 3 or 4;

[0099] 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 or 2; when there are two or more R g When two or more R g The same or different from each other, or two adjacent R g are connected to each other to form a substituted or unsubstituted ring;

[0100] The g'1 is selected from 0, 1 or 2; when there are two or more R g ', two or more R g 'same or different from each other;

[0101] The Ar1 and Ar2 are independently selected from any one of the following groups:

[0102]

[0103] The v is independently selected from any one of CH and N;

[0104] The y is independently selected from any one of CH and N, and at least two of the y are selected from N;

[0105] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0106] Said X1 and X2 are independently selected from O, S, N (R v )

[0107] Said X3 is selected from S, C(R p R q )、N(R z )

[0108] Said X4 and X5 are independently selected from O, S, C(R p R q )、N(R z )

[0109] The R c 、R c 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring;

[0110] The R c " is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C1-C25 heterocycloalkyl;

[0111] The R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring;

[0112] The R v 、R z Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0113] Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3 or 4; said c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c5 is selected from 0, 1 or 2; said c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said c7 is selected from 0, 1, 2 or 3; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0114] The c'0 is selected from 0 or 1; the c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; when there are two or more R c ', two or more R c 'same or different from each other;

[0115] The c"1 is selected from 0, 1, 2 or 3; the c"2 is selected from 0, 1, 2, 3 or 4; the c"3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R c", two or more R c ” are the same as or different from each other;

[0116] The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused sub-cyclic group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused sub-cyclic group;

[0117] It does not contain the following compounds:

[0118]

[0119] Preferably, the fluorene compound is selected from any one of the following structures:

[0120]

[0121] The definitions of R1, R2, R3, a, b, z, x, Ar1, Ar2, L1, and L2 are the same as those in Formula I.

[0122] Preferably, R1, R2, and R3 are independently selected from the group consisting of formula II, hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl , triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, Any one of dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl.

[0123] More preferably, R1, R2, and R3 are independently selected from Formula II.

[0124] More preferably, R1 and R2 are independently selected from Formula II.

[0125] More preferably, R1 and R3 are independently selected from Formula II.

[0126] More preferably, R2 and R3 are independently selected from Formula II.

[0127] More preferably, the R1 is selected from Formula II.

[0128] More preferably, said R2 is selected from Formula II.

[0129] More preferably, said R3 is selected from Formula II.

[0130] Preferably, the fluorene compound is selected from any one of the following structures:

[0131]

[0132]

[0133] a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; when two or more R2 are present, the two or more R2 are the same or different, or two adjacent R2 are connected to form a substituted or unsubstituted ring;

[0134] b1 is selected from 0, 1, 2, 3 or 4; b2 is selected from 0, 1, 2 or 3; b3 is selected from 0, 1 or 2; when two or more R3 are present, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to form a substituted or unsubstituted ring;

[0135] The R1, R2, R3, R x , z, x, q, Ar1, Ar2, L, L1, and L2 are defined the same as in Formula I.

[0136] Preferably, the R xindependently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl.

[0137] Preferably, L is selected from the following groups: single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, anthracene, phenanthrenyl, triphenylene, pyrenyl, perylene, fluoranthenyl, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, dibenzocarbazolylene any one of oxazolyl, benzodibenzofuranyl, benzodibenzothiophenylyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzoxazolyl, dibenzothiazolyl, dibenzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, bipyridyl, bipyrimidyl, phenylpyridyl, and phenylpyrimidyl.

[0138] Preferably, the Select any one of the following structures:

[0139]

[0140] The R n independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylol, cyclohexyl, cycloheptyl, cyclohex ... any one of methylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;

[0141] The n1 is selected from 0, 1 or 2; the n2 is selected from 0 or 1; when there are two or more R n When two or more R n the same as or different from each other;

[0142] The definitions of Ar1, Ar2, L1, and L2 are the same as those in Formula I.

[0143] Preferably, L is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0144]

[0145]

[0146] The u is independently selected from any one of CH and N;

[0147] The R g 、R g independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthiocyclopropyl, benzocyclobutyl, naphthiocyclobutyl, benzocyclopentyl, naphthiocyclopentyl, benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl , triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, Any one of dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl;

[0148] The R m 、R tindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-3 ...

[0149] The R u independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, cyclohexyl, cyclohept ... any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;

[0150] The g'1 is selected from 0, 1 or 2; the g'2 is selected from 0, 1, 2, 3 or 4; the g'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the g'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the g'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R g ', two or more R g ' are the same as or different from each other.

[0151] More preferably, L is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0152]

[0153] Preferably, the formula II Any one selected from the following groups:

[0154]

[0155]

[0156] More preferably, the formula III Any one selected from the following groups:

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] More preferably, the formula IV Any one selected from the following groups:

[0164]

[0165] Preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0166]

[0167]

[0168] The R c 、R c independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, benzocyclopropyl, naphthiocyclopropyl, benzocyclobutyl, naphthiocyclobutyl, benzocyclopentyl, naphthiocyclopentyl, benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl;

[0169] The R c" is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, and triethylsilyl;

[0170] The R p 、R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-3 ...

[0171] The R v 、R z independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, cyclohexyl, cyclohept ... any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;

[0172] The L' is selected from the following groups: single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, triphenylene, pyrenylene, perylene, fluoranthenylene, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothiophenylene, benzocarbazolylene, dibenzofuranylene, dibenzothiophenylene ... Any one of carbazolyl, benzodibenzofuranyl, benzodibenzothiophenylyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzoxazolyl, dibenzothiazolyl, dibenzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, bipyridyl, bipyrimidyl, phenylpyridyl, and phenylpyrimidyl;

[0173] Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3 or 4; said c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c5 is selected from 0, 1 or 2; said c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said c7 is selected from 0, 1, 2 or 3; said c8 is selected from 0, 1, 2, 3, 4, 5 or 6; said c9 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c 10 Selected from 0 or 1; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0174] The c'0 is selected from 0 or 1; the c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R c ', two or more R c 'same or different from each other;

[0175] The c"1 is selected from 0, 1, 2 or 3; the c"2 is selected from 0, 1, 2, 3 or 4; the c"3 is selected from 0, 1, 2, 3, 4 or 5; the c"4 is selected from 0, 1 or 2; the c"5 is selected from 0 or 1; when there are two or more R c ", two or more R c " are the same as or different from each other.

[0176] More preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] Preferably, L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0184]

[0185]

[0186] The r is independently selected from any one of CH and N;

[0187] The Y a 、Y b Independently selected from O, S, N(R s )

[0188] The Y c 、Y d 、Y e Independently selected from O, S, C(R i R j )、N(R k )

[0189] The ring B is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0190] The R f 、R f'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C11 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C11 heteroaromatic ring;

[0191] The R i 、R j independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R i 、R j are connected to form a substituted or unsubstituted ring;

[0192] The R s 、R k Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0193] Said p is selected from 1, 2, 3 or 4;

[0194] The f1 is selected from 0, 1, 2, 3 or 4; the f2 is selected from 0, 1, 2, 3, 4, 5 or 6; the f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the f4 is selected from 0, 1 or 2; when there are two or more R f When two or more R f The same or different from each other, or two adjacent R f are connected to each other to form a substituted or unsubstituted ring;

[0195] The f'1 is selected from 0, 1 or 2; when there are two or more R f ', two or more R f ' are the same as or different from each other.

[0196] More preferably, L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0197]

[0198]

[0199] The R f 、R f independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthiocyclopropyl, benzocyclobutyl, naphthiocyclobutyl, benzocyclopentyl, naphthiocyclopentyl, benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl , triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, Any one of dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl;

[0200] The R i 、R jindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-3 ...

[0201] The R s 、R k independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, cyclohexyl, cyclohept ... any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;

[0202] The f'1 is selected from 0, 1 or 2; the f'2 is selected from 0, 1, 2, 3 or 4; the f'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the f'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the f'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R f ', two or more R f ' are the same as or different from each other.

[0203] More preferably, L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0204]

[0205]

[0206] Preferably, the L1-Ar1 and L2-Ar2 are the same or different from each other, more preferably different. Most preferably, the formula I is selected from any one of the following structures:

[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] The above lists some specific structural forms of the fluorene compounds represented by Chemical Formula I of the present invention, but the present invention is not limited to these listed chemical structures. All chemical structures based on the structure shown in Chemical Formula I and with substituents as defined above should be included.

[0235] The present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, wherein the organic layer comprises at least one of the fluorene compounds described in the present invention.

[0236] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of an electron transport layer, a hole blocking layer, a light-emitting layer, and a charge generation layer, and at least one of the electron transport layer, the hole blocking layer, the light-emitting layer, and the charge generation layer includes at least one of the fluorene compounds described in the present invention.

[0237] More preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises at least one of the fluorene compounds described in the present invention.

[0238] More preferably, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises at least one of the fluorene compounds described in the present invention.

[0239] More preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the fluorene compounds described in the present invention.

[0240] More preferably, the light-emitting layer comprises a host material, and the host material comprises at least one of the aromatic amine compounds described in the present invention.

[0241] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer includes at least one of the fluorene compounds described in the present invention.

[0242] More preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the N-type charge generation layer contains at least one of the fluorene compounds described in the present invention.

[0243] The anode of the present invention preferably has a material with a high work function. The anode can be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode can be selected from metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0244] The hole injection layer of the present invention preferably comprises a material having a good hole-accepting ability. Examples of the material include metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers. Examples include, but are not limited to, 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), hexacyanohexaazatriphenylene, and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane.

[0245] The hole transport layer of the present invention preferably has a material with high hole mobility. It may include biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazatriphenylene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc. For example, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-di(4-biphenyl)-N,N'-diphenylbenzidine, etc., but is not limited thereto.

[0246] The electron blocking layer of the present invention preferably comprises a material having good hole transport and electron blocking capabilities. Examples include aromatic amine derivatives, carbazole derivatives, and the like. Examples include, but are not limited to, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) and N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD).

[0247] The light-emitting layer of the present invention can use red, green or blue light-emitting materials, and generally includes a host material and a dopant material. The light-emitting layer material may include multiple host materials and multiple dopant materials. The host material of the light-emitting layer needs to have bipolar charge transport properties and appropriate energy levels to effectively transfer the excitation energy to the guest light-emitting material. In addition to using the fluorene compound provided by the present invention alone as the host material, the fluorene compound provided by the present invention can also be used in combination with a p-type host material as an n-type host material. The host material may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, distyryl aryl derivatives, stilbene derivatives, etc. For example, ADN, Alq3, BAlq, TPBi, TPD, CBP, TCTA, etc., but are not limited thereto. The fluorene compound of the present invention is preferred. The doping material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The fluorescent luminescent material is a compound that emits light in a singlet excited state, including aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc., such as BCzVBi, DPAVBi, etc. Phosphorescent luminescent materials can also be used, including metal complexes such as iridium complexes, osmium complexes, platinum complexes, such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc., but are not limited to these.

[0248] The hole blocking layer of the present invention preferably has good electron transport properties and a material that blocks or limits hole transport, and can generally be formed using the same conditions as the hole injection layer. In addition to the fluorene compounds provided by the present invention, aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymer compounds, etc., such as TPBi, BAlq, BCP, TmPyPB, etc., but are not limited thereto. The fluorene compounds of the present invention are preferred.

[0249] The electron transport layer of the present invention preferably has a material with high electron mobility and can be a single-layer structure or a multilayer structure. In addition to the fluorene compounds provided by the present invention, metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other aromatic heterocyclic compounds, polymer compounds, etc., such as Alq3, BeBq2, BAlq, PBD, ZnPBO, PBD, BPhen, etc., but are not limited thereto. The fluorene compounds of the present invention are preferred.

[0250] The electron injection layer of the present invention preferably has a material with good electron-accepting ability. It can include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron-injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiO, Yb, Tb, 8-hydroxyquinoline cesium, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0251] The cathode of the present invention is preferably a low work function material. It may include a metal, a metal alloy, or a multilayer structure, such as Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.

[0252] The cover layer material of the present invention preferably has a high refractive index. Examples include metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, and aromatic amine compounds, such as, but not limited to, Alq3, NPD, CBP, LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, and ZnS.

[0253] The P-type charge generation layer material of the present invention includes an organic material doped with a metal or a P-type dopant. For example, the metal may include an alloy of one or two of the group consisting of aluminum (Al), copper (Cu), iron (Fe), lead (Pb), zinc (Zn), gold (Au), platinum (Pt), tungsten (W), indium (In), molybdenum (Mo), nickel (Ni), and titanium (Ti). The P-type dopant may include F4-TCNQ, iodine (I), ferric chloride (FeCl3), ferric fluoride (FeF3), and antimony chloride (SbCl5). The host may include at least one selected from the group consisting of NPB, TPD, TNB, and HAT-CN, but is not limited thereto.

[0254] In addition to the fluorene compounds provided herein, the N-type charge generation layer materials described herein may also include N-type dopant organic materials such as alkali metals such as Li, Na, K, Rb, Cs, and Fr; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, and Ra; Group 15 metals such as Bi (bismuth) and Sb (antimony); lanthanide metals such as La (lanthanum), Ce (cerium), Pr (praseodymium), Nd (neodymium), Pm (promethium), Sm (samarium), and Gd (gadolinium); and compounds of one or more of the above metals. Alternatively, organic N-type dopants with electron-donating properties that can donate at least a portion of the electron charge to an organic host to form a charge transfer complex with the organic host may be used. Examples include, but are not limited to, BEDT-TTF and TTF. Fluorene compounds of the present invention are preferred.

[0255] The following is a method for preparing the compound represented by Chemical Formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of Chemical Formula I can be prepared by the reaction scheme shown below. The substituents can be bonded using methods known in the art, and the type and position of the substituents or the number of substituents can be varied according to techniques known in the art.

[0256] [Synthetic route]

[0257] Preparation of compounds of formula I:

[0258]

[0259] Xa, Xb, Xc, Xd, and Xe are each independently selected from any one of Cl, Br, and I; the definitions of R1, R2, R3, a, b, z, L1, L2, Ar1, Ar2, x, m, and n are the same as those above.

[0260] Description of raw materials, reagents and characterization equipment:

[0261] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. They may be commercially available products or prepared by methods well known to those skilled in the art.

[0262] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0263] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0264] [Synthesis Example 1] Synthesis of Compound 10

[0265]

[0266] Synthetic intermediate d-10

[0267] Under nitrogen protection, e-10 (71.24 g, 120 mmol), f-10 (30.47 g, 120 mmol), KOAc (23.55 g, 240 mmol) were added to the reaction flask, and then 600 mL of DMF solution was added. After the air was replaced with nitrogen three times, Pd(dppf)Cl2 (0.88 g, 1.2 mmol) was added and the reaction was stirred for 8 h. After the reaction was completed, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (600 mL×3 times). The organic phase was separated and dried over anhydrous magnesium sulfate. The obtained solid was recrystallized and purified using n-hexane: ethyl acetate = 9:1 (v / v) to obtain d-10 (66.12 g, yield 86%), HPLC purity ≧99.68%, mass spectrum m / z: 640.2953 (theoretical value: 640.2969).

[0268] Synthetic intermediate A-10

[0269] Under nitrogen protection, a-10 (18.44 g, 100.00 mmol), b-10 (12.19 g, 100.00 mmol), Na2CO3 (15.90 g, 150.00 mmol), Pd(OAC)2 (0.22 g, 1.00 mmol), P(t-Bu)3 (4.00 mL of 0.50 M toluene solution, 2.00 mmol), and 800 mL of toluene / ethanol / water (2:1:1) were added to the reaction flask and stirred at reflux for 9 hours. After the reaction, the mixture was cooled to room temperature, a small amount of distilled water was added, the organic phase was separated, filtered on silica gel, and the solvent was evaporated under reduced pressure. The crude product obtained after filtration was recrystallized from ethyl acetate to obtain intermediate A-10 (16.95 g, yield 75%); HPLC analysis of the solid purity was ≥99.79%. Mass spectrum m / z: 224.9852 (theoretical value: 224.9861).

[0270] Synthetic intermediate B-10

[0271] Under nitrogen, a reaction flask was charged with A-10 (13.56 g, 60.00 mmol), C-10 (11.88 g, 60.00 mmol), Na2CO3 (9.54 g, 90.00 mmol), Pd(PPh3)4 (0.69 g, 0.60 mmol), and 800 mL of toluene / ethanol / water (2:1:1). The mixture was stirred and reacted at reflux for 10 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain intermediate B-10 (14.85 g, 72% yield). The solid purity was ≥99.84% as determined by HPLC. Mass spectrum: m / z: 343.0889 (theoretical value: 343.0876).

[0272] Synthesis of compound 10

[0273] Under nitrogen, a reaction flask was added with B-10 (10.31 g, 30.00 mmol), d-10 (19.22 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(dppf)Cl2 (0.22 g, 0.30 mmol), and 500 mL of toluene / ethanol / water (2:1:1). The mixture was stirred and reacted under reflux for 14 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain compound 10 (17.02 g, 69% yield). The purity of the solid was ≥99.94% by HPLC. Mass spectrum m / z: 821.3244 (theoretical value: 821.3226). Theoretical element content (%): C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured element content (%): C, 86.23; H, 5.25; N, 5.12.

[0274] [Synthesis Example 2] Synthesis of Compound 72

[0275]

[0276] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-72, c-10 was replaced with an equal molar amount of c-72, and d-10 was replaced with an equal molar amount of b-10 to obtain compound 72 (14.36 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 621.2615 (theoretical value: 621.2600). Theoretical element content (%): C 43 H 35 N3Si: C, 83.05; H, 5.67; N, 6.76. Measured element content (%): C, 83.06; H, 5.68; N, 6.73.

[0277] [Synthesis Example 3] Synthesis of Compound 84

[0278]

[0279] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-84, b-10 was replaced with an equal molar amount of b-84, c-10 was replaced with an equal molar amount of d-84, and d-10 was replaced with an equal molar amount of b-84 to obtain compound 84 (17.01 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 765.3377 (theoretical value: 765.3391). Theoretical element content (%): C 49 H 51 N3Si3: C, 76.81; H, 6.71; N, 5.48. Measured element content (%): C, 76.83; H, 6.72; N, 5.45.

[0280] [Synthesis Example 4] Synthesis of Compound 94

[0281]

[0282] Preparation of intermediate e-94:

[0283] THF (400 mL) and g-94 (41.47 g, 155.00 mmol) were added to the reaction flask in sequence. After cooling to -78°C, a 15% n-butyllithium hexane solution (75 ml, 150.00 mmol) was slowly added dropwise at this temperature, stirred to dissolve, and reacted for 1 hour. h-94 (45.67 g, 150.00 mmol) was dissolved in THF (125 mL) and added dropwise. After the addition was complete, the reaction mixture was stirred for another hour and then warmed to room temperature overnight. The solvent was evaporated under reduced pressure, and acetic acid (225 mL) and fuming HCl (25 mL) were added to the concentrated solution. The mixture was heated to reflux for 5 hours and stirred at room temperature overnight. The resulting suspension was diluted with water and extracted with DCM. The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated to dryness to obtain a crude product, which was recrystallized from isopropanol to afford e-94 (58.44 g, 82% yield). HPLC analysis of the solid revealed a purity of ≥99.76%. Mass spectrum: m / z: 474.1586 (theoretical value: 474.1571).

[0284] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-94, c-10 was replaced with an equal molar amount of d-94, and d-10 was replaced with an equal molar amount of b-10 to obtain compound 94 (14.72 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 671.2772 (theoretical value: 671.2757). Theoretical element content (%): C 47 H 37 N3Si: C, 84.02; H, 5.55; N, 6.25. Measured element content (%): C, 84.03; H, 5.57; N, 6.24.

[0285] [Synthesis Example 5] Synthesis of Compound 116

[0286]

[0287] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-116, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 116 (16.03 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 702.3214 (theoretical value: 702.3227). Theoretical element content (%): C 49 H 34 D5N3Si: C, 83.72; H, 6.31; N, 5.98. Measured element content (%): C, 83.74; H, 6.32; N, 5.94.

[0288] [Synthesis Example 6] Synthesis of Compound 127

[0289]

[0290] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-127, c-10 was replaced with an equal molar amount of c-127, and d-10 was replaced with an equal molar amount of d-127 to obtain compound 127 (16.38 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 747.3053 (theoretical value: 747.3070). Theoretical element content (%): C 53 H 41 N3Si: C, 85.10; H, 5.53; N, 5.62. Measured element content (%): C, 85.13; H, 5.51; N, 5.61.

[0291] [Synthesis Example 7] Synthesis of Compound 132

[0292]

[0293] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-132, c-10 was replaced with an equal molar amount of c-127, and d-10 was replaced with an equal molar amount of d-132 to obtain compound 132 (16.12 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 697.2929 (theoretical value: 697.2913). Theoretical element content (%): C 49 H 39 N3Si: C, 84.32; H, 5.63; N, 6.02. Measured element content (%): C, 84.34; H, 5.64; N, 6.01.

[0294] [Synthesis Example 8] Synthesis of Compound 138

[0295]

[0296] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-138, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 138 (17.18 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 773.3238 (theoretical value: 773.3226). Theoretical element content (%): C 55 H 43 N3Si: C, 85.34; H, 5.60; N, 5.43. Measured element content (%): C, 85.33; H, 5.62; N, 5.41.

[0297] [Synthesis Example 9] Synthesis of Compound 148

[0298]

[0299] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-148, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 148 (17.00 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 797.3245 (theoretical value: 797.3226). Theoretical element content (%): C 57 H 43 N3Si: C, 85.78; H, 5.43; N, 5.27. Measured element content (%): C, 85.75; H, 5.46; N, 5.25.

[0300] [Synthesis Example 10] Synthesis of Compound 169

[0301]

[0302] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-169, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 169 (16.14 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 736.3010 (theoretical value: 736.3022). Theoretical element content (%): C 51 H 40 N4Si: C, 83.12; H, 5.47; N, 7.60. Measured element content (%): C, 83.13; H, 5.46; N, 7.64.

[0303] [Synthesis Example 11] Synthesis of Compound 172

[0304]

[0305] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-172, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 172 (15.96 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 738.2831 (theoretical value: 738.2815). Theoretical element content (%): C 50 H 38 N4OSi: C, 81.27; H, 5.18; N, 7.58. Measured element content (%): C, 81.29; H, 5.15; N, 7.57.

[0306] [Synthesis Example 12] Synthesis of Compound 189

[0307]

[0308] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of d-84, c-10 was replaced with an equal molar amount of b-10, and d-10 was replaced with an equal molar amount of d-84 to obtain Compound 189 (17.94 g). The solid purity was ≥99.90% as determined by HPLC. Mass spectrum m / z: 933.3948 (theoretical value: 933.3935). Theoretical element content (%): C 65 H 55 N3Si2: C, 83.56; H, 5.93; N, 4.50. Measured element content (%): C, 83.52; H, 5.96; N, 4.52.

[0309] [Synthesis Example 13] Synthesis of Compound 197

[0310]

[0311] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-197, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 197 (17.55 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 859.3366 (theoretical value: 859.3383). Theoretical element content (%): C 62 H 45 N3Si: C, 86.58; H, 5.27; N, 4.89. Measured element content (%): C, 86.56; H, 5.28; N, 4.86.

[0312] [Synthesis Example 14] Synthesis of Compound 211

[0313]

[0314] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-211, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 211 (18.13 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 862.3472 (theoretical value: 862.3492). Theoretical element content (%): C 61 H 46 N4Si: C, 84.88; H, 5.37; N, 6.49. Measured element content (%): C, 84.85; H, 5.38; N, 6.45.

[0315] [Synthesis Example 15] Synthesis of Compound 215

[0316]

[0317] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-215, and D-10 was replaced with an equal molar amount of D-84 to obtain Compound 215 (17.87 g). The solid purity was ≥99.89% as determined by HPLC. Mass spectrum m / z: 875.3347 (theoretical value: 875.3332). Theoretical element content (%): C 62 H 45 N3OSi: C, 85.00; H, 5.18; N, 4.80. Measured element content (%): C, 85.04; H, 5.15; N, 4.82.

[0318] [Synthesis Example 16] Synthesis of Compound 221

[0319]

[0320] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of c-127, c-10 was replaced with an equal molar amount of c-72, and d-10 was replaced with an equal molar amount of c-127 to obtain compound 221 (17.18 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 773.3237 (theoretical value: 773.3226). Theoretical element content (%): C 55 H 43 N3Si: C, 85.34; H, 5.60; N, 5.43. Measured element content (%): C, 85.32; H, 5.63; N, 5.42.

[0321] [Synthesis Example 17] Synthesis of Compound 257

[0322]

[0323] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of c-127, c-10 was replaced with an equal molar amount of c-257, and d-10 was replaced with an equal molar amount of d-84 to obtain compound 257 (18.18 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 829.2956 (theoretical value: 829.2947). Theoretical element content (%): C 57 H 43 N3SSi: C, 82.47; H, 5.22; N, 5.06. Measured element content (%): C, 82.46; H, 5.24; N, 5.05.

[0324] [Synthesis Example 18] Synthesis of Compound 275

[0325]

[0326] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-275, c-10 was replaced with an equal molar amount of d-84, and d-10 was replaced with an equal molar amount of b-275 to obtain compound 275 (18.36 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 873.3557 (theoretical value: 873.3539). Theoretical element content (%): C 63 H 47 N3Si: C, 86.56; H, 5.42; N, 4.81. Measured element content (%): C, 86.53; H, 5.43; N, 4.84.

[0327] [Synthesis Example 19] Synthesis of Compound 278

[0328]

[0329] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-278, c-10 was replaced with an equal molar amount of d-84, and d-10 was replaced with an equal molar amount of b-278 to obtain compound 278 (17.26 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 821.3239 (theoretical value: 821.3226). Theoretical element content (%): C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured element content (%): C, 86.24; H, 5.25; N, 5.12.

[0330] [Synthesis Example 20] Synthesis of Compound 279

[0331]

[0332] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-279, b-10 was replaced with an equal molar amount of b-279, c-10 was replaced with an equal molar amount of c-279, and d-10 was replaced with an equal molar amount of d-84 to obtain Compound 279 (17.64 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 827.3315 (theoretical value: 827.3332). Theoretical element content (%): C 58 H 45 N3OSi: C, 84.12; H, 5.48; N, 5.07. Measured element content (%): C, 84.14; H, 5.45; N, 5.06.

[0333] [Synthesis Example 21] Synthesis of Compound 298

[0334]

[0335] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-298, c-10 was replaced with an equal molar amount of d-84, and d-10 was replaced with an equal molar amount of b-298 to obtain compound 298 (18.02 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 833.2370 (theoretical value: 833.2355). Theoretical element content (%): C 55 H 39 N3S2Si: C, 79.20; H, 4.71; N, 5.04. Measured element content (%): C, 79.23; H, 4.72; N, 5.01.

[0336] [Synthesis Example 22] Synthesis of Compound 307

[0337]

[0338] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-307, c-10 was replaced with an equal molar amount of c-307, and d-10 was replaced with an equal molar amount of d-307 to obtain compound 307 (16.45 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 711.2918 (theoretical value: 711.2901). Theoretical element content (%): C 46 H 42 FN3Si2: C, 77.60; H, 5.95; N, 5.90. Measured element content (%): C, 77.62; H, 5.91; N, 5.93.

[0339] [Synthesis Example 23] Synthesis of Compound 319

[0340]

[0341] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-319, c-10 was replaced with an equal molar amount of c-127, and d-10 was replaced with an equal molar amount of d-307 to obtain compound 319 (17.85 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 825.3949 (theoretical value: 825.3935). Theoretical element content (%): C 56 H 55 N3Si2: C, 81.41; H, 6.71; N, 5.09. Measured element content (%): C, 81.44; H, 6.70; N, 5.08.

[0342] [Synthesis Example 24] Synthesis of Compound 402

[0343]

[0344] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-402, c-10 was replaced with an equal molar amount of c-402, and d-10 was replaced with an equal molar amount of d-402 to obtain compound 402 (17.26 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 809.3606 (theoretical value: 809.3622). Theoretical element content (%): C 55 H 51 N3Si2: C, 81.54; H, 6.35; N, 5.19. Measured element content (%): C, 81.55; H, 6.32; N, 5.17.

[0345] [Synthesis Example 25] Synthesis of Compound 446

[0346]

[0347] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-446, and D-10 was replaced with an equal molar amount of D-446 to obtain Compound 446 (17.43 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 829.3841 (theoretical value: 829.3852). Theoretical element content (%): C 59 H 51 N3Si: C, 85.36; H, 6.19; N, 5.06. Measured element content (%): C, 85.38; H, 6.16; N, 5.04.

[0348] [Synthesis Example 26] Synthesis of Compound 475

[0349]

[0350] Preparation of intermediate e-475:

[0351] Under argon, b-84 (23.29 g, 120.00 mmol), j-475 (51.81 g, 120.00 mmol), tetrakistriphenylphosphine palladium (1.39 g, 1.20 mmol), potassium acetate (23.55 g, 240.00 mmol), and 710 mL of a 3:1:1 toluene / ethanol / water mixture were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3.5 hours. After the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake, which was rinsed with ethanol and recrystallized from toluene to obtain intermediate e-475 (50.52 g, 84% yield). HPLC analysis of the solid revealed a purity of ≥99.73%. Mass spectrum: m / z: 500.1738 (theoretical value: 500.1727).

[0352] According to the preparation method of Synthesis Example 1, e-10 was replaced with an equal molar amount of e-475, b-10 was replaced with an equal molar amount of b-475, c-10 was replaced with an equal molar amount of d-475, and d-10 was replaced with an equal molar amount of b-475 to obtain compound 475 (18.36 g). The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum m / z: 849.3526 (theoretical value: 849.3539). Theoretical element content (%): C 61 H 47 N3Si: C, 86.18; H, 5.57; N, 4.94. Measured element content (%): C, 86.16; H, 5.58; N, 4.91.

[0353] [Synthesis Example 27] Synthesis of Compound 486

[0354]

[0355] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-486, and D-10 was replaced with an equal molar amount of B-10 to obtain Compound 486 (14.18 g). The purity of the solid was ≥99.99% as determined by HPLC. Mass spectrum m / z: 621.2612 (theoretical value: 621.2600). Theoretical element content (%): C 43 H 35 N3Si: C, 83.05; H, 5.67; N, 6.76. Measured element content (%): C, 83.08; H, 5.65; N, 6.73.

[0356] [Synthesis Example 28] Synthesis of Compound 512

[0357]

[0358] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of c-127, c-10 was replaced with an equal molar amount of c-512, and d-10 was replaced with an equal molar amount of c-486 to obtain compound 512 (17.98 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 831.4023 (theoretical value: 831.4009). Theoretical element content (%): C 59 H 53 N3Si: C, 85.16; H, 6.42; N, 5.05. Measured element content (%): C, 85.14; H, 6.45; N, 5.03.

[0359] [Synthesis Example 29] Synthesis of Compound 673

[0360]

[0361] Synthetic intermediate A-673

[0362] Under nitrogen, a-673 (16.34 g, 60.00 mmol), b-673 (23.88 g, 120.00 mmol), K2CO3 (12.44 g, 90.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred and reacted at reflux for 8 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain intermediate A-673 (20.71 g, 82% yield). The solid purity was ≥99.85% as determined by HPLC. Mass spectrum: m / z: 420.1158 (theoretical value: 420.1142).

[0363] Synthesis of compound 673

[0364] Under nitrogen, A-673 (12.63 g, 30.00 mmol), d-84 (15.50 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), Pd(dppf)Cl2 (0.22 g, 0.30 mmol), and 480 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask and stirred at reflux for 10 hours. After the reaction, the mixture was cooled to room temperature, filtered, and washed with distilled water. The resulting solid was then recrystallized from toluene to obtain compound 673 (17.44 g, 75% yield); HPLC analysis of the solid revealed a purity of ≥99.96%. Mass spectrum: m / z: 774.3166 (theoretical value: 774.3179). Theoretical element content (%): C 54 H 42 N4Si: C, 83.68; H, 5.46; N, 7.23. Measured element content (%): C, 83.64; H, 5.47; N, 7.25.

[0365] [Synthesis Example 30] Synthesis of Compound 722

[0366]

[0367] According to the preparation method of Synthesis Example 29, b-673 was replaced with an equal molar amount of b-722, and d-84 was replaced with an equal molar amount of d-307 to obtain Compound 722 (19.96 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 1022.4217 (theoretical value: 1022.4200). Theoretical element content (%): C 71 H 58 N4Si2: C, 83.32; H, 5.71; N, 5.47. Measured element content (%): C, 83.35; H, 5.72; N, 5.44.

[0368] [Synthesis Example 31] Synthesis of Compound 796

[0369]

[0370] According to the preparation method of Synthesis Example 29, b-673 was replaced with an equal molar amount of c-127, and d-84 was replaced with an equal molar amount of c-486 to obtain compound 796 (16.93 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 772.3259 (theoretical value: 772.3274). Theoretical element content (%): C 56 H 44 N2Si: C, 87.01; H, 5.74; N, 3.62. Measured element content (%): C, 87.04; H, 5.71; N, 3.63.

[0371] [Synthesis Example 32] Synthesis of Compound 808

[0372]

[0373] According to the preparation method of Synthesis Example 29, b-673 was replaced with an equal molar amount of b-808, and d-84 was replaced with an equal molar amount of c-486 to obtain compound 808 (15.14 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 700.2533 (theoretical value: 700.2546). Theoretical element content (%): C 48 H 36 N2O2Si: C, 82.25; H, 5.18; N, 4.00. Measured element content (%): C, 82.26; H, 5.16; N, 4.02.

[0374] [Synthesis Example 33] Synthesis of Compound 844

[0375]

[0376] Preparation of intermediate e-844:

[0377] THF (400 mL) and g-94 (41.17 g, 155.00 mmol) were added to the reaction flask in sequence. After cooling to -78°C, a 15% n-butyllithium hexane solution (75 ml, 150.00 mmol) was slowly added dropwise at this temperature, stirred to dissolve, and reacted for 1 hour. h-844 (40.26 g, 150.00 mmol) was dissolved in THF (125 mL) and added dropwise. After the addition was complete, the reaction mixture was stirred for another hour and then warmed to room temperature overnight. The solvent was evaporated under reduced pressure, and acetic acid (225 mL) and fuming HCl (25 mL) were added to the concentrated solution. The mixture was heated to reflux for 5 hours and stirred at room temperature overnight. The resulting suspension was diluted with water and extracted with DCM. The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated to dryness to obtain a crude product, which was recrystallized from isopropanol to afford e-844 (57.30 g, 87% yield). HPLC analysis of the solid revealed a purity of ≥99.78%. Mass spectrum: m / z: 438.1561 (theoretical value: 438.1571).

[0378] Synthetic intermediate d-844

[0379] Under nitrogen protection, e-844 (52.69 g, 120 mmol), f-10 (30.47 g, 120 mmol), KOAc (23.55 g, 240 mmol) were added to the reaction flask, and then 600 mL of DMF solution was added. After the air was replaced with nitrogen three times, Pd(dppf)Cl2 (0.88 g, 1.2 mmol) was added and the reaction was stirred for 8 h. After the reaction was completed, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (600 mL×3 times). The organic phase was separated and dried over anhydrous magnesium sulfate. The obtained solid was recrystallized and purified using n-hexane: ethyl acetate = 9:1 (v / v) to give d-844 (54.12 g, yield 85%), HPLC purity ≧99.91%, mass spectrum m / z: 530.2830 (theoretical value: 530.2812).

[0380] According to the preparation method of Synthesis Example 29, a-673 was replaced with an equal molar amount of a-844, b-673 was replaced with an equal molar amount of b-10, and d-84 was replaced with an equal molar amount of d-844 to obtain compound 844 (14.64 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 633.2863 (theoretical value: 633.2852). Theoretical element content (%): C 46 H 39 NSi: C, 87.16; H, 6.20; N, 2.21. Measured element content (%): C, 87.15; H, 6.22; N, 2.24.

[0381] [Synthesis Example 34] Synthesis of Compound 852

[0382]

[0383] Synthetic intermediate d-852

[0384] Under nitrogen protection, e-852 (61.39 g, 120 mmol), f-10 (30.47 g, 120 mmol), KOAc (23.55 g, 240 mmol) were added to the reaction flask, and then 600 mL of DMF solution was added. After the air was replaced by nitrogen three times, Pd(dppf)Cl2 (0.88 g, 1.2 mmol) was added and the reaction was stirred for 8 h. After the reaction was completed, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (600 mL×3 times). The organic phase was separated and dried over anhydrous magnesium sulfate. The obtained solid was recrystallized and purified using n-hexane: ethyl acetate = 9:1 (v / v) to obtain d-852 (55.64 g, yield 83%), HPLC purity ≧99.92%, mass spectrum m / z: 558.3110 (theoretical value: 558.3125).

[0385] According to the preparation method of Synthesis Example 29, a-673 was replaced with an equal molar amount of a-844, b-673 was replaced with an equal molar amount of b-10, and d-84 was replaced with an equal molar amount of d-852 to obtain compound 852 (15.49 g). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 661.3182 (theoretical value: 661.3165). Theoretical element content (%): C 48 H 43 NSi: C, 87.09; H, 6.55; N, 2.12. Measured element content (%): C, 87.07; H, 6.54; N, 2.16.

[0386] [Synthesis Example 35] Synthesis of Compound 884

[0387]

[0388] According to the preparation method of Synthesis Example 29, a-673 was replaced with an equal molar amount of a-844, and b-673 was replaced with an equal molar amount of b-884 to obtain Compound 884 (16.03 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 721.2925 (theoretical value: 721.2913). Theoretical element content (%): C 51 H 39 N3Si: C, 84.84; H, 5.45; N, 5.82. Measured element content (%): C, 84.86; H, 5.42; N, 5.85.

[0389] [Synthesis Example 36] Synthesis of Compound 891

[0390]

[0391] According to the preparation method of Synthesis Example 29, a-673 was replaced with an equal molar amount of a-844, and b-673 was replaced with an equal molar amount of b-891 to obtain Compound 891 (18.88 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 885.2649 (theoretical value: 885.2668). Theoretical element content (%): C 59 H 43 N3S2Si: C, 79.96; H, 4.89; N, 4.74. Measured element content (%): C, 79.94; H, 4.86; N, 4.78.

[0392] [Synthesis Example 37] Synthesis of Compound 996

[0393]

[0394] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of D-84, and D-10 was replaced with an equal molar amount of B-10 to obtain Compound 996 (14.55 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 621.2609 (theoretical value: 621.2600). Theoretical element content (%): C 43 H 35 N3Si: C, 83.05; H, 5.67; N, 6.76. Measured element content (%): C, 83.06; H, 5.64; N, 6.73.

[0395] [Synthesis Example 38] Synthesis of Compound 999

[0396]

[0397] According to the preparation method of Synthesis Example 1, C-10 was replaced with an equal molar amount of C-999, and D-10 was replaced with an equal molar amount of C-486 to obtain Compound 999 (14.50 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 635.2743 (theoretical value: 635.2757). Theoretical element content (%): C 44 H 37 N3Si: C, 83.11; H, 5.87; N, 6.61. Measured element content (%): C, 83.12; H, 5.85; N, 6.64.

[0398] [Synthesis Example 39] Synthesis of Compound 1002

[0399]

[0400] According to the preparation method of Synthesis Example 29, a-673 was replaced with an equal molar amount of a-1002, and b-673 was replaced with an equal molar amount of c-127 to obtain Compound 1002 (15.98 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 771.3330 (theoretical value: 771.3321). Theoretical element content (%): C 57 H 45 NSi: C, 88.67; H, 5.88; N, 1.81. Measured element content (%): C, 88.66; H, 5.84; N, 1.83.

[0401] [Device Example]

[0402] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to test the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System.

[0403] [Example 1]

[0404] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol and then dried. After drying, it was transferred to a plasma cleaning machine. After washing, the substrate was transferred to an evaporation machine. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was evaporated on the anode to form a thickness of HT-1 was evaporated on the hole injection layer to form a hole injection layer with a thickness of EB-1 is evaporated on the hole transport layer to form a hole transport layer with a thickness of The electron blocking layer is deposited on the electron blocking layer. The light-emitting layer is formed with GH-1 as the main material of the light-emitting layer and doped with 6wt% GD-1 to form a thickness of The compound 10 of the present invention and LiQ (mass ratio 1:1) were evaporated on the light-emitting layer to form a layer with a thickness of LiF is evaporated on the electron transport layer to form an electron transport layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.

[0405]

[0406] [Examples 2 to 39]

[0407] Compound 72, compound 84, compound 94, compound 116, compound 127, compound 132, compound 138, compound 148, compound 169, compound 172, compound 189, compound 197, compound 211, compound 215, compound 221, compound 257, compound 275, compound 278, compound 279, compound 298, compound 307, compound 319, compound 402, compound 446, compound 475, compound 486, compound 512, compound 673, compound 722, compound 796, compound 808, compound 844, compound 852, compound 884, compound 891, compound 996, compound 999, and compound 1002 of the present invention were used to replace compound 10 in Example 1 as electron transport layer materials. Except that, an organic electroluminescent device was prepared by the same preparation method as in Example 1.

[0408] [Comparative Examples 1 to 5]

[0409] Organic electroluminescent devices were prepared by the same preparation method as in Example 1 except that Compound 10 in Example 1 was replaced by Compound P-1, Compound P-2, Compound P-3, Compound P-4 and Compound P-5 as electron transport layer materials.

[0410] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments 1 to 39 and comparative examples 1 to 5 are shown in Table 1 below.

[0411] Table 1:

[0412]

[0413]

[0414]

[0415] The results in Table 1 show that when the fluorene compounds of the present invention are applied to the electron transport layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-1 to P-5. The fluorene compounds of the present invention are electron transport layer materials with good performance.

[0416] [Example 40]

[0417] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol and then dried. After drying, it was transferred to a plasma cleaning machine. After washing, the substrate was transferred to a vapor deposition machine. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was evaporated on the anode to form a thickness of HT-1 was evaporated on the hole injection layer to form a hole injection layer with a thickness of EB-2 is evaporated on the hole transport layer to form a hole transport layer with a thickness of The electron blocking layer is deposited on the electron blocking layer. The light-emitting layer is formed with BH-2 as the main material of the light-emitting layer and BD-2 doped with 4 wt% to form a thickness of The compound 10 of the present invention is evaporated on the luminescent layer to form a luminescent layer with a thickness of ET-2:LiQ (mass ratio 1:1) was evaporated on the hole blocking layer to form a hole blocking layer with a thickness of LiF is evaporated on the electron transport layer to form an electron transport layer with a thickness of The electron injection layer is formed by evaporating Mg:Ag (mass ratio 1:9) on the electron injection layer to form a layer with a thickness of CP-2 is evaporated on the cathode layer to form a thickness of Thus, an organic light-emitting device is formed.

[0418]

[0419] [Examples 41 to 78]

[0420] Compound 72, compound 84, compound 94, compound 116, compound 127, compound 132, compound 138, compound 148, compound 169, compound 172, compound 189, compound 197, compound 211, compound 215, compound 221, compound 257, compound 275, compound 278, compound 279, compound 298, compound 307, compound 319, compound 402, compound 446, compound 475, compound 486, compound 512, compound 673, compound 722, compound 796, compound 808, compound 844, compound 852, compound 884, compound 891, compound 996, compound 999, and compound 1002 of the present invention were used to replace compound 10 in Example 40 as hole blocking layer materials. Except that, an organic electroluminescent device was prepared by the same preparation method as in Example 40.

[0421] [Comparative Examples 6 to 8]

[0422] Organic electroluminescent devices were prepared by the same preparation method as in Example 40, except that Compound P-6, Compound P-7 and Compound P-8 were used instead of Compound 10 in Example 40 as hole blocking layer materials.

[0423] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments 40 to 78 of the present invention and the comparative embodiments 6 to 8 are shown in Table 2 below.

[0424] Table 2:

[0425]

[0426]

[0427] The results in Table 2 show that when the fluorene compounds of the present invention are applied to the hole blocking layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-6 to P-8. The compounds of the present invention are hole blocking layer materials with good performance.

[0428] [Example 79]

[0429] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol and then dried. After drying, it was transferred to a plasma cleaning machine. After washing, the substrate was transferred to a vapor deposition machine. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was evaporated on the anode to form a thickness of Hole injection layer 1. HT-1 is evaporated on the hole injection layer 1 to form a hole injection layer with a thickness of The hole transport layer 1 is formed by evaporating an electron blocking layer EB-3 on the hole transport layer 1 to form a hole transport layer 1 having a thickness of The electron blocking layer 1 is deposited on the electron blocking layer 1. The light emitting layer 1 is formed by evaporating BH-3 as the main material of the light emitting layer and doping 5wt% of BD-3 to form a thickness of ET-3:LiQ (mass ratio 1:1) was evaporated on the light-emitting layer 1 to form a layer with a thickness of The electron transport layer 1 is formed by evaporating the compound 84 of the present invention and doping 5 wt% of Yb on the electron transport layer 1 to form a layer with a thickness of HT-1:TCNQ (mass ratio of 80:20) was evaporated on the N-type charge generation layer to form a layer with a thickness of HT-1 is evaporated on the P-type charge generation layer to form a P-type charge generation layer with a thickness of The hole transport layer 2 is formed by evaporating an electron blocking layer EB-3 on the hole transport layer 2 to form a hole transport layer 2 having a thickness of The electron blocking layer 2 is deposited on the electron blocking layer 2. The light emitting layer 2 is formed by evaporating BH-3 as the main material of the light emitting layer and doping 5wt% of BD-3 to form a thickness of ET-3:LiQ (mass ratio 1:1) was evaporated on the light-emitting layer 2 to form a thickness of The electron transport layer 2 is formed by evaporating LiF on the electron transport layer 2 to form a layer with a thickness of The electron injection layer is formed by evaporating Mg:Ag (mass ratio 1:9) on the electron injection layer to form a layer with a thickness of CP-2 is evaporated on the cathode layer to form a thickness of Thus, an organic light-emitting device is formed.

[0430]

[0431] [Examples 80 to 98]

[0432] Compound 94, Compound 116, Compound 169, Compound 172, Compound 189, Compound 197, Compound 211, Compound 257, Compound 275, Compound 279, Compound 298, Compound 307, Compound 319, Compound 512, Compound 673, Compound 796, Compound 808, Compound 844, and Compound 884 of the present invention were used to replace Compound 84 in Example 79 as N-type charge generation layer materials. Except for this, an organic electroluminescent device was prepared by the same preparation method as Example 79.

[0433] [Comparative Example 9]

[0434] An organic electroluminescent device was prepared by the same preparation method as in Example 79, except that Compound P-9 was used instead of Compound 84 in Example 79 as the material for the N-type charge generation layer.

[0435] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Examples 79 to 98 of the present invention and Comparative Example 9 are shown in Table 3 below.

[0436] Table 3:

[0437]

[0438]

[0439] The results in Table 3 show that when the fluorene compound of the present invention is applied to the N-type charge generation layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compound P-9. The compound of the present invention is an N-type charge generation layer material with good performance.

[0440] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A fluorene compound, characterized in that: The fluorene compound has a structure represented by Formula I: Wherein, said z is independently selected from any one of CH and N; The x is independently selected from C(R n ), any one of N, and at least one of the x is selected from N; The m is selected from 0 or 1; the n is selected from 0 or 1; and the m and n are not selected from 0 or 1 at the same time; The R1, R2, R3, R n independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, and at least one of R1, R2, and R3 is selected from Formula II; The R x Any one independently selected from substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said q is selected from 1, 2, 3, 4 or 5; The a is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring; The b is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring; The L is selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The u is independently selected from any one of CH and N; Said Y1 and Y2 are independently selected from O, S, N (R u ) Said Y3 is selected from O, S, N (R u ) Said Y4 and Y5 are independently selected from O, S, C(R m R t )、N(R u ) The ring C is selected from a substituted or unsubstituted C3-C10 alicyclic ring; The R g 、R g 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C11 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C11 heteroaromatic ring; The R m 、R t independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R m 、R t are connected to form a substituted or unsubstituted ring; The R u Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The h is selected from 1, 2, 3 or 4; 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 or 2; when there are two or more R g When two or more R g The same or different from each other, or two adjacent R g are connected to each other to form a substituted or unsubstituted ring; The g'1 is selected from 0, 1 or 2; when there are two or more R g ', two or more R g 'same or different from each other; The Ar1 and Ar2 are independently selected from any one of the following groups: The v is independently selected from any one of CH and N; The y is independently selected from any one of CH and N, and at least two of the y are selected from N; The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring; Said X1 and X2 are independently selected from O, S, N (R v ) Said X3 is selected from S, C(R p R q )、N(R z ) Said X4 and X5 are independently selected from O, S, C(R p R q )、N(R z ) The R c 、R c 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring; The R c " is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C1-C25 heterocycloalkyl; The R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring; The R v 、R z Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3 or 4; said c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c5 is selected from 0, 1 or 2; said c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said c7 is selected from 0, 1, 2 or 3; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring; The c'0 is selected from 0 or 1; the c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; when there are two or more R c ', two or more R c 'same or different from each other; The c"1 is selected from 0, 1, 2 or 3; the c"2 is selected from 0, 1, 2, 3 or 4; the c"3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R c ", two or more R c ” are the same as or different from each other; The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused sub-cyclic group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused sub-cyclic group; It does not contain the following compounds:

2. The fluorene compound according to claim 1, characterized in that The fluorene compound is selected from any one of the following structures: The definitions of R1, R2, R3, a, b, z, x, Ar1, Ar2, L1, and L2 are the same as those in Formula I.

3. The fluorene compound according to claim 1, characterized in that The fluorene compound is selected from any one of the following structures: a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; when two or more R2 are present, the two or more R2 are the same or different, or two adjacent R2 are connected to form a substituted or unsubstituted ring; b1 is selected from 0, 1, 2, 3 or 4; b2 is selected from 0, 1, 2 or 3; b3 is selected from 0, 1 or 2; when two or more R3 are present, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to form a substituted or unsubstituted ring; The R1, R2, R3, R x , z, x, q, Ar1, Ar2, L, L1, and L2 are defined the same as in Formula I.

4. The fluorene compound according to claim 1, characterized in that described Select any one of the following structures: The R n independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylol, cyclohexyl, cycloheptyl, cyclohex ... any one of methylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; The n1 is selected from 0, 1 or 2; the n2 is selected from 0 or 1; when there are two or more R n When two or more R n the same as or different from each other; The definitions of Ar1, Ar2, L1, and L2 are the same as those in Formula I.

5. The fluorene compound according to claim 1, characterized in that The Ar1 and Ar2 are independently selected from any one of the following groups: The R c 、R c independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, benzocyclopropyl, naphthiocyclopropyl, benzocyclobutyl, naphthiocyclobutyl, benzocyclopentyl, naphthiocyclopentyl, benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl; The R c " is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, and triethylsilyl; The R p 、R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro-1,2-dihydro-1,2-dihydro-1,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-3 ... The R v 、R z independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, cyclohexyl, cyclohept ... any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; The L' is selected from the following groups: single bond, substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, triphenylene, pyrenylene, perylene, fluoranthenylene, pyridylene, pyrimidylene, triazinylene, furylene, thienylene, carbazolylene, benzofuranylene, benzothiophenylene, benzocarbazolylene, dibenzofuranylene, dibenzothiophenylene ... Any one of carbazolyl, benzodibenzofuranyl, benzodibenzothiophenylyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzoxazolyl, dibenzothiazolyl, dibenzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, bipyridyl, bipyrimidyl, phenylpyridyl, and phenylpyrimidyl; Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3 or 4; said c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c5 is selected from 0, 1 or 2; said c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said c7 is selected from 0, 1, 2 or 3; said c8 is selected from 0, 1, 2, 3, 4, 5 or 6; said c9 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c 10 Selected from 0 or 1; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring; The c'0 is selected from 0 or 1; the c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R c ', two or more R c 'same or different from each other; The c"1 is selected from 0, 1, 2 or 3; the c"2 is selected from 0, 1, 2, 3 or 4; the c"3 is selected from 0, 1, 2, 3, 4 or 5; the c"4 is selected from 0, 1 or 2; the c"5 is selected from 0 or 1; when there are two or more R c ", two or more R c " are the same as or different from each other.

6. The fluorene compound according to claim 1, characterized in that The L1 and L2 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The r is independently selected from any one of CH and N; The Y a 、Y b Independently selected from O, S, N(R s ) The Y c 、Y d 、Y e Independently selected from O, S, C(R i R j )、N(R k ) The ring B is selected from a substituted or unsubstituted C3-C10 alicyclic ring; The R f 、R f 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C11 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C11 heteroaromatic ring; The R i 、R j independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R i 、R j are connected to form a substituted or unsubstituted ring; The R s 、R k Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said p is selected from 1, 2, 3 or 4; The f1 is selected from 0, 1, 2, 3 or 4; the f2 is selected from 0, 1, 2, 3, 4, 5 or 6; the f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the f4 is selected from 0, 1 or 2; when there are two or more R f When two or more R f The same or different from each other, or two adjacent R f are connected to each other to form a substituted or unsubstituted ring; The f'1 is selected from 0, 1 or 2; when there are two or more R f ', two or more R f ' are the same as or different from each other.

7. The fluorene compound according to claim 1, characterized in that The L1-Ar1 and L2-Ar2 are the same as or different from each other, and more preferably different from each other.

8. The fluorene compound according to claim 1, characterized in that The formula I is selected from any one of the following structures:

9. An organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on a side of the cathode facing away from the anode, wherein: The organic layer comprises at least one of the fluorene compounds according to any one of claims 1 to 8.

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

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