CN117384120A - Fluorene-containing triarylamine compound and organic electroluminescent device thereof - Google Patents

Fluorene-containing triarylamine compound and organic electroluminescent device thereof Download PDF

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CN117384120A
CN117384120A CN202311315435.0A CN202311315435A CN117384120A CN 117384120 A CN117384120 A CN 117384120A CN 202311315435 A CN202311315435 A CN 202311315435A CN 117384120 A CN117384120 A CN 117384120A
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substituted
unsubstituted
ring
group
alicyclic
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刘喜庆
孙敬
周雯庭
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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Abstract

In order to solve the problems in the prior art of the existing organic electroluminescent materials and devices, the invention provides a fluorene-containing triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The fluorene-containing triarylamine compound provided by the invention has higher glass transition temperature and good film forming property, can form a uniform amorphous film without pinholes, has good thermal stability after film forming, can effectively avoid the damage of a contact surface of a material layer caused by crystallization due to heating in the working process, and simultaneously has higher hole mobility and proper HOMO energy level so as to facilitate effective hole injection in the working process; in addition, the compound has high film refractive index in the visible light range and regular molecular orientation in the film. The organic light-emitting diode is used as a second hole transport layer or a cover layer material to be applied to an organic light-emitting diode, so that the light-emitting efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

Fluorene-containing triarylamine compound and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a triarylamine compound containing fluorene and an organic electroluminescent device thereof.
Background
In recent years, organic electroluminescent devices (OLEDs, organic Light Emitting Diode) are a new generation of display technology, and have been widely focused at home and abroad due to their characteristics of self-luminescence, wide viewing angle, short reaction time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, flexible size design, flexible shape design, simple preparation method, etc., and have become a research hotspot in academia and industry. In addition, the flexibility of the organic material enables the future flat panel display to have portable, light and thin and impact-resistant properties, so that the organic electroluminescent material and the device have wide application prospect.
Currently, most OLEDs employ multi-layer sandwich type dual-carrier direct current injection devices, which are generally classified into double-layer, three-layer and multi-layer device structures, because of the disadvantage of the single-layer structure, and the efficiency and the service life of the OLEDs are closely related to the device structure. Conventional OLEDs are composed of a cathode (low work function metal), an anode (ITO), and an organic functional layer between the two electrodes, which generally includes a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), a capping layer (CPL), and the like. Under the drive of an applied voltage, electrons and holes are respectively injected from the cathode and the anode to the HOMO energy level of the electron transport layer and the LUMO energy level of the hole transport layer, and due to the existence of extremely poor energy, electrons at the HOMO energy level and holes at the LUMO energy level continuously migrate to the light-emitting layer, then are recombined in the light-emitting layer to form excitons, and emit light after radiation relaxation.
The hole transport material is used as one of important components of the organic electroluminescent device, and has the basic functions of improving the transport efficiency of holes in the device, effectively blocking electrons in the luminescent layer and realizing the maximum recombination of carriers; meanwhile, the energy barrier of holes in the injection process is reduced, and the injection efficiency of the holes is improved, so that the brightness, the efficiency and the service life of the device are improved. Therefore, the main research direction of the hole transport material mainly aims at two problems, namely, the hole transport capacity is improved, the hole transport material has proper HOMO orbit energy level so as to ensure effective injection and transport of holes between an anode and a hole layer and between the hole layer and a light-emitting layer, and the heat stability and the film forming property of the material are improved by adjusting the structure of the material. Therefore, it is important to develop a hole transport layer type material having a high mobility and an appropriate HOMO orbital level.
Because of the great gap between the external quantum efficiency and the internal quantum efficiency of OLEDs, the development of OLEDs is greatly restricted. Therefore, attention has been paid to how to reduce the total reflection effect in OLEDs and to increase the proportion of light coupled into the device front to the external space (light extraction efficiency). The simplest and most effective method is to form a cover layer on the transparent electrode as a light extraction functional layer, which can be used for reducing total reflection loss and waveguide loss in OLEDs and improving light coupling-out efficiency. Therefore, in order to achieve the combination of high efficiency, long life, and low voltage characteristics of the device, it is a primary task of those skilled in the industry to develop high performance materials that can be applied to the capping layer.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a triarylamine compound containing fluorene and an organic electroluminescent device thereof, which can effectively improve the luminous efficiency, the driving voltage and the service life of OLEDs.
Specifically, the invention provides a fluorene-containing triarylamine compound, which is represented by the following formula I:
the R is 0 、R 1 Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
said n 0 Selected from 0, 1, 2, 3 or 4; when n is 0 Above 1, two or more R 0 Are identical or different from each other, or adjacent two R 0 Are connected with each other to form a substituted or unsubstituted ring;
said n 1 Selected from 0, 1, 2, 3 or 4; when n is 1 Above 1, two or more R 1 Are identical or different from each other, or adjacent two R 1 Are connected with each other to form a substituted or unsubstituted ring;
the Ar is selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of C6-C60, a substituted or unsubstituted heteroaryl group of C2-C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and an aromatic ring of C6-C60, and a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C60 and a heteroaromatic ring of C2-C30;
the Ar is as follows 1 Any one or a combination of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C30 alicyclic ring, and a condensed ring group of a C6-C60 aromatic ring;
the Ar is as follows 2 Selected from the group represented by formula 1-a or 1-b, wherein the ring A is selected from any one of C6-C30 aryl, C2-C30 heteroaryl;
the X is selected from O, S or N (R) a )；
The Y is independently selected from O or S;
each z is independently selected from CH or N; z fused to ring a is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The L is 0 One or a combination of a substituted or unsubstituted arylene group of C6-C60, a substituted or unsubstituted heteroarylene group of C2-C60, a substituted or unsubstituted fused ring group of an alicyclic ring of C3-C30 and an aromatic ring of C6-C60, and a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and a heteroaromatic ring of C2-C60;
the L is 1 、L 2 Each independently selected from one or a combination of a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60;
the X is selected from N (R) a ) When the L is 2 Not selected from single bonds.
The invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode or on the side of the cathode away from the anode, wherein the organic layer comprises the fluorene-containing triarylamine compound.
Advantageous effects
The fluorene-containing triarylamine compound shown in the formula I has higher glass transition temperature and good thermal stability, so that crystallization is avoided from generating heat in the working process, a uniform amorphous film without pinholes can be formed, damage to the contact surface of a material layer can be avoided, and the compound has a proper HOMO orbit energy level, so that injection and transmission of holes between an electrode/an organic layer and an organic layer/an organic layer interface are ensured, and the efficiency and the service life of a device can be effectively improved; in addition, the compound has higher refractive index, good thermal conductivity and light transmittance in the visible light range, and can obviously improve the light coupling-out efficiency of the device.
In conclusion, the fluorene-containing triarylamine compound provided by the invention has higher mobility and refractive index, higher glass transition temperature, and good film forming property and thermal stability, and can effectively improve the luminous efficiency of an organic electroluminescent device and prolong the service life of the device when being applied to a second hole transport layer or a cover layer of the organic electroluminescent device.
Detailed Description
In the following, a technical solution with embodiments of the present invention will be further clarified and fully elucidated, and it will be apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.
In the present description of the invention,meaning a moiety attached to another substituent. />May be attached at any optional position of the attached group/fragment.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to any of the two or more rings, in particular to any of the corresponding selectable sites of the rings. For example, the number of the cells to be processed, Can indicate-> Can indicate->And so on.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring. For example, the number of the cells to be processed,can indicate-> Can indicate-> Can represent And so on.
Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.
The alkyl group according to the present invention means a generic term for monovalent groups remaining after removal of one hydrogen atom in an alkane molecule, and may be a straight-chain alkyl group, a branched alkyl group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 15 carbon atoms, still more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms, including but 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 alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably, but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc.
As used herein, "substituted or unsubstituted silyl" refers to-Si (R k ) 3 A group wherein each R k Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano,Halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R k Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, particularly preferably 1 to 8 carbon atoms. The cycloalkyl radicals preferably have 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 3 to 10 carbon atoms, particularly preferably 3 to 7 carbon atoms. Preferably, each R k Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.
The cycloalkyl refers to the general term that monovalent groups are remained after one hydrogen atom is removed from a cyclic alkane molecule, and the cycloalkyl can be monocyclic cycloalkyl, polycyclic cycloalkyl or bridged cycloalkyl. Preferably from 3 to 20 carbon atoms, more preferably from 3 to 18 carbon atoms, even more preferably from 3 to 12 carbon atoms, particularly preferably from 3 to 6 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphene, fenchyl, isobornyl, and the like.
The aryl refers to the general term that monovalent groups are left after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic compound molecule, and the aryl can be monocyclic aryl, polycyclic aryl or condensed ring aryl. Preferably from 6 to 60 carbon atoms, more preferably from 6 to 30 carbon atoms, even more preferably from 6 to 18 carbon atoms, particularly preferably from 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetrabiphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, and the like, but are not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, and specific examples may include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirofluorenyl, spirobifluorenyl, and the like.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably having 2 to 30 carbon atoms, more preferably having 2 to 18 carbon atoms, and particularly preferably having 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused ring heteroaryl group may include, but are not limited to, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorene oxaanthracenyl, spirofluorene thianthrenyl, and the like.
The arylene group according to the present invention is a generic term for divalent radicals remaining after removal of two hydrogen atoms from the aromatic nucleus carbon 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 60 carbon atoms, more preferably having 6 to 30 carbon atoms, even more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; specific examples may include, but are not limited to, naphthylene, anthrylene, phenanthrylene, pyreylene, triphenylene, fluoranthenylene, and the like.
By heteroarylene is meant that at least one carbon atom in the arylene group is replaced with a heteroatom, which includes but is not limited to oxygen, sulfur, nitrogen, or phosphorus atoms, leaving the generic term for divalent radicals. Preferably from 2 to 60 carbon atoms, more preferably from 2 to 30 carbon atoms, even more preferably from 2 to 18 carbon atoms, particularly preferably from 2 to 12 carbon atoms. The attachment site of the heteroarylene group may be on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. Specific examples of the monocyclic and condensed ring heteroarylene groups may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, a carbazolylene group, a benzofuranylene group, a benzothienyl group, a benzocarbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzocarbazolylene group, and the like; specific examples of the polycyclic heteroarylene group may include bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but are not limited thereto.
The fused ring group of the alicyclic ring and the aromatic ring refers to the general term that after the alicyclic ring and the aromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 6 to 60 carbon atoms, more preferably having 6 to 30 carbon atoms, still more preferably having 6 to 18 carbon atoms, and particularly preferably having 6 to 12 carbon atoms, and the fused ring group of the alicyclic and aromatic rings may include, but is not limited to, benzocyclopropane group, benzocyclobutane group, benzocyclobutene group, indanyl group, indenyl group, tetrahydronaphthyl group, dihydronaphthyl group, benzocycloheptane group, benzocycloheptenyl group, and the like.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the sum of monovalent groups obtained by removing one hydrogen atom after the alicyclic ring and the heteroaromatic ring are fused together. Preferably from 5 to 30 carbon atoms, more preferably from 5 to 18 carbon atoms, particularly preferably from 5 to 12 carbon atoms. The fused cyclic group of the alicyclic and heteroaromatic ring may include, but is not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidbenzocycloheptyl, dibenzofuran-cyclopropyl, dibenzofuran-cyclobutyl, dibenzofuran-cyclopentyl, dibenzofuran-cyclohexyl, dibenzofuran-cycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-cyclobutyl, dibenzothiophene-cyclopentyl, dibenzothiophene-cyclohexyl, dibenzothiophene-cycloheptyl, carbazole-cyclopropyl, carbazole-cyclobutyl, carbazole-cyclopentyl, carbazole-cyclohexyl, carbazole-cycloheptyl, and the like.
The term "fused ring-sub-group" as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring to an aromatic ring and then removing two hydrogen atoms. Preferably having 6 to 30 carbon atoms, more preferably having 6 to 25 carbon atoms, still more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms, and the fused-back ring group of the alicyclic ring and the aromatic ring may include, but is not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic term of bivalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing two hydrogen atoms. Preferably having 3 to 30 carbon atoms, more preferably having 3 to 20 carbon atoms, still more preferably having 3 to 18 carbon atoms, particularly preferably having 3 to 12 carbon atoms, and the fused-back ring group of the alicyclic ring and the heteroaromatic ring may include a pyrido-cyclopropyl group, a pyrido-cyclobutyl group, a pyrido-cyclopentyl group, a pyrido-cyclohexyl group, a pyrido-benzoheptyl group, a pyrimido-cyclopropyl group, a pyrimido-cyclobutyl group, a pyrimido-cyclopentyl group, a pyrimido-cyclohexyl group, a pyrimido-benzocycloheptyl group, a dibenzofuran-cyclopropyl group, a dibenzofuran-cyclobutyl group, a dibenzofuran-cyclopentyl group, a dibenzofuran-cyclohexyl group, a dibenzofuran-cycloheptyl group, a dibenzothiophene-cyclopropyl group, a dibenzothiophene-cyclopentyl group, a dibenzothiophene-cyclohexyl group, a dibenzothiophene-cycloheptyl group, a carbazole-cyclopropyl group, a carbazole-benzocarbazole-cyclobutyl group, a carbazole-cyclopentyl group, a carbazolo-cyclohexyl group, a carbazolo-cycloheptyl group, and the like, but is not limited thereto.
The "substituted … …" such as "substituted alkyl group, substituted cycloalkyl group, substituted aryl group, substituted heteroaryl group, substituted alicyclic and aromatic ring condensed ring group, substituted arylene group, substituted heteroarylene group, alicyclic and aromatic ring condensed ring group, alicyclic and heteroaromatic ring condensed ring group" as referred to in the present invention means that it is independently mono-or poly-substituted with: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and the like, but are not limited thereto, or two adjacent substituents may be linked to form a ring. Preferably mono-or polysubstituted by: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, perylenyl, pyrenyl, benzyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, phenothiazinyl, phenoxazinyl, indolyl, and the like, but are not limited thereto.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be a three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, condensed ring or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole or the like, but is not limited thereto.
The invention provides a fluorene-containing triarylamine compound, which has a structure shown in a formula I:
the R is 0 、R 1 Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said n 0 Selected from 0, 1, 2, 3 or 4; when n is 0 Above 1, two or more R 0 Are identical or different from each other, or adjacent two R 0 Are connected with each other to form a substituted or unsubstituted ring;
said n 1 Selected from 0, 1, 2, 3 or 4; when n is 1 Above 1, two or more R 1 Are identical or different from each other, or adjacent two R 1 Are connected with each other to form a substituted or unsubstituted ring;
the Ar is selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of C6-C60, a substituted or unsubstituted heteroaryl group of C2-C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and an aromatic ring of C6-C60, and a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C60 and a heteroaromatic ring of C2-C30;
the Ar is as follows 1 Any one or a combination of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C30 alicyclic ring, and a condensed ring group of a C6-C60 aromatic ring;
the Ar is as follows 2 Selected from the group represented by formula 1-a or 1-b, wherein the ring A is selected from any one of C6-C30 aryl, C2-C30 heteroaryl;
The X is selected from O, S or N (R) a )；
The Y is independently selected from O or S;
each z is independently selected from CH or N; z fused to ring a is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the L is 0 One or a combination of a substituted or unsubstituted arylene group of C6-C60, a substituted or unsubstituted heteroarylene group of C2-C60, a substituted or unsubstituted fused ring group of an alicyclic ring of C3-C30 and an aromatic ring of C6-C60, and a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and a heteroaromatic ring of C2-C60;
the L is 1 、L 2 Each independently selected from one or a combination of a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60;
The X is selected from N (R) a ) When the L is 2 Not selected from single bonds.
Preferably, ar is selected from any one or a combination of the following groups:
each t is independently selected from CH or N;
the Y is 1 Selected from O, S or N (R) b )；
The Y is 2 Selected from CH or N;
the Y is 3 Independently selected from O or S;
the Y is 4 Selected from O, S, C (R) c R d )、N(R e ) Any one of them;
the R is b 、R e Each independently selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is c 、R d Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R c 、R d Form a substituted or unsubstituted ring;
the R is 2 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 2 Are connected with each other to form a substituted or unsubstituted ring;
the a 1 Selected from 0,1. 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3, 4 or 5.
Still more preferably, ar is selected from any one or a combination of the following groups:
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is m Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R m Form a substituted or unsubstituted ring;
the R is 2 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and aromatic ring of C6-C30, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and heteroaromatic ring of C2-C30, or adjacent two R 2 Are connected with each other to form a substituted or unsubstituted ring;
the a 0 Selected from 0, 1 or 2; the a 1 Selected from 0, 1, 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3, 4 or 5; the a 3 Selected from 0, 1, 2, 3, 4, 5 or 6; the a 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the a 6 Selected from 0, 1, 2 or 3; the a 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the a 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the a 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Preferably, said R b Selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylalkyl, cyclobutylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, and mixtures thereof 9, 9-dimethylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-tert-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphthyl, deutero-anthryl, deutero-phenanthryl, deutero-triphenylenyl, deutero-pyridyl, deutero-pyrimidinyl, deutero-quinolinyl, deutero-isoquinolinyl, deuterated benzofurals Pyranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteromethyl-substituted isopropyl-substituted phenyl, deuteromethyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, any one of triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, said R m Independently selected from hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butylButyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylyl, cyclobutanyl, cyclopentylalkyl, cyclohexenyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, Ethyl substituted naphthyl, isopropyl substituted phenyl, isopropyl substituted biphenyl, isopropyl substituted naphthyl, tert-butyl substituted adamantyl, tert-butyl substituted phenyl, tert-butyl substituted biphenyl, tert-butyl substituted naphthyl, tert-butyl substituted phenanthryl, tert-butyl substituted 9, 9-dimethylfluorenyl, tert-butyl substituted 9, 9-diphenylfluorenyl, tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, triphenylsilyl substituted phenyl, trimethylsilyl substituted naphthyl, adamantyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuteromethyl substituted phenyl, deuteromethyl substituted biphenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, phenyl substituted phenyl, benzofuransubstituted phenyl, benzothiophene substituted phenyl, pyridine substituted phenyl, quinoline substituted phenyl, benzoquinoline substituted phenyl, quinoline substituted phenyl, or benzoquinoline substituted phenyl.
Preferably, said R 2 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutanyl, cyclopentylalkyl, cyclohexenyl, cycloheptanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinylQuinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, benzodibenzofuranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthracenyl, deuterated phenanthrenyl, thiazolyl, and the like deuterated triphenylene, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl Any one of alkyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteroethyl-substituted biphenyl, deuteroethyl-substituted phenyl, deuteroethyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, the Ar 1 Any one or a combination of the following groups:
the R is f Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R f To form a substituted or unsubstituted carbocyclic ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each otherForming a substituted or unsubstituted ring;
said b 0 Selected from 0, 1, 2 or 3; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4 or 5; said b 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 7 Selected from 0, 1 or 2.
Still preferably, the Ar 1 Any one or a combination of the following groups:
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the R is 3 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptylalkyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-tert-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-n-propyl, deutero-norbornyl Naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylenyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylenyl, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroisopropyl-substituted phenyl, deuteroisopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylsubstituted phenyl, or two adjacent R 3 Are connected with each other to form a substituted or unsubstituted ring;
said b 0 Selected from 0, 1, 2 or 3; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4 or 5; said b 3 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 7 Selected from 0, 1 or 2;said b 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Preferably, the Ar 2 Selected from one of the following groups represented by formulae 1-a, 1-b:
each z is independently selected from CH or N;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring.
Preferably, said R a Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylalkyl, cyclobutanyl, cyclopentylalkyl, cycloheptylalkyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropylalkyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptylalkyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthridinyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9' -spirobifluorenylBenzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthracenyl, deuterated phenanthrenyl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteromethyl-substituted phenyl Any one of deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, the Ar 2 Selected from one of the following groups represented by formulae 1-a, 1-b:
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preferably, the L 0 Selected from any one or a combination of the following groups 1 ～L 2 Each independently selected from a single bond or one or a combination of the groups shown below:
each r is independently selected from CH or N;
the Y is 5 Selected from O, S or N (R) x )；
The Y is 6 Selected from CH or N;
the Y is 7 Selected from O, S, C (R) p R q )、N(R z ) Any one of them;
the R is x 、R z Each independently selected from the group consisting of substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, and substituted or unsubstituted C6-to-up Any one of aryl group of C30, substituted or unsubstituted heteroaryl group of C2-C30, fused ring group of substituted or unsubstituted alicyclic ring of C3-C30 and aromatic ring of C6-C30, fused ring group of substituted or unsubstituted alicyclic ring of C3-C30 and heteroaromatic ring of C2-C30;
the R is p 、R q Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R p 、R q Form a substituted or unsubstituted ring;
the R is 4 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the X is selected from N (R) a ) When the L is 2 Not selected from single bonds;
said e 0 Selected from 0, 1 or 2; said e 1 Selected from 0, 1, 2, 3 or 4; said e 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 5 Selected from 0, 1, 2 or 3.
Still preferably, the L 0 Selected from any one or a combination of the following groups 1 ～L 2 Each independently selected from a single bond or one or a combination of the groups shown below:
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the R is n Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R n Form a substituted or unsubstituted ring;
the R is 5 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and aromatic ring of C6-C30, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and heteroaromatic ring of C2-C30, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
the X is selected from N (R) a ) When the L is 2 Not selected from single bonds;
said e 0 Selected from 0, 1 or 2; said e 1 Selected from 0, 1, 2, 3 or 4; said e 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 5 Selected from 0, 1, 2 or 3; said e 6 Selected from 0, 1, 2, 3, 4 or 5; said e 7 Selected from 0, 1, 2, 3, 4, 5, 6 or 7.
Preferably, said R n Each independently selectFrom hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthryl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl Phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteroesopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, said R 5 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenylBenzocyclohexenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, and the like 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, and dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, and deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylyl, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, Trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroisopropyl-substituted phenyl, deuteroisopropyl-substituted biphenyl, deuteroitertiarybutyl-substituted phenyl, deuteroitertiarybutyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, the L 0 Any one or a combination of the following groups:
said e 0 Selected from 0, 1 or 2; said e 1 Selected from 0, 1, 2, 3 or 4; said e 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 5 Selected from 0, 1, 2 or 3; said e 6 Selected from 0, 1, 2, 3, 4 or 5.
Preferably, said R 5 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl,cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzohexenyl, naphthyl, anthryl, phenanthrenyl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9' -spirobifluorenyl, benzo 9,9' -dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deuteroisopropyl, deutero-n-butyl, deuteroisobutyl, deutero-sec-butyl, deutero-tert-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphthyl, deutero-anthryl, deutero-phenanthryl, deutero-triphenylyl, deutero-pyridinyl, deutero-pyrimidinyl, deutero-quinolinyl, deutero-isoquinolinyl, deutero-benzofuranyl, deutero-benzothienyl, deutero-benzoxazolyl, deutero-benzothiazolyl, deutero-benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl Substituted 9, 9-dimethylfluorenyl, tert-butyl substituted 9, 9-diphenylfluorenyl, tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, triphenylsilyl substituted phenyl, trimethylsilyl substituted naphthyl, adamantyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuteromethyl substituted phenyl, deuteromethyl substituted biphenyl, deuteromethyl substituted phenyl, deuteroisopropyl substituted biphenyl, deuteromethyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, triphenylyl substituted phenyl, benzofuran substituted phenyl, benzothiophene substituted phenyl, pyridine substituted phenyl, pyrimidine substituted phenyl, quinoline substituted phenyl, isoquinoline substituted phenyl, quinazoline substituted phenyl, quinoxaline substituted phenyl, benzoxazole substituted phenyl, benzothiazole substituted phenyl, benzimidazole substituted phenyl.
Most preferably, the fluorene-containing triarylamine compound is selected from any one of the structures shown below:
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The above list of some specific structural forms of the fluorene-containing triarylamine compound represented by formula I according to the present invention, but the present invention is not limited to these listed chemical structures, and substituents are included as defined above, even when the structure represented by formula I is used as a basis.
The invention also provides an organic electroluminescent device which comprises at least one of the fluorene-containing triarylamine compounds.
Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or positioned on one side of the cathode away from the anode, and the organic layer comprises at least one of the fluorene-containing triarylamine compounds.
Preferably, the organic electroluminescent device according to the present invention may include one or more organic layers, the organic layers may include a hole transport region, a light emitting layer, an electron transport region, and a capping layer, and particularly, the organic layers between the anode and the cathode may include a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, etc., and the organic layers on a side of the cathode facing away from the anode may include a capping layer. The organic layer may be formed of a single-layer structure or a multilayer structure in which the above organic layers are stacked; meanwhile, each organic layer may further include one or more layers, for example, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer. However, the structure of the organic electroluminescent device is not limited thereto, and may include fewer or more organic layers.
Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a hole transport region, a luminescent layer, an electron transport region and a cover layer, the luminescent layer is positioned between the anode and the cathode, the hole transport region is positioned between the anode and the luminescent layer, the hole transport region comprises a hole injection layer and a hole transport layer, the hole transport layer is positioned between the hole injection layer and the luminescent layer, and the hole transport layer comprises at least one of the fluorene-containing triarylamine compounds.
Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the hole injection layer and the light emitting layer, the second hole transport layer is located between the first hole transport layer and the light emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises at least one of the fluorene-containing triarylamine compound according to the present invention; preferably, the first hole transport layer comprises at least one of the fluorene-containing triarylamine compounds of the present invention; preferably, the second hole transport layer comprises at least one of the fluorene-containing triarylamine compounds of the present invention; preferably, at least one of the fluorene-containing triarylamine compounds of the present invention is contained in the first hole transport layer and the second hole transport layer.
Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer and a third hole transport layer, the first hole transport layer is located between the hole injection layer and the light emitting layer, the second hole transport layer is located between the first hole transport layer and the light emitting layer, the third hole transport layer is located between the second hole transport layer and the light emitting layer, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer comprises at least one of the fluorene-containing triarylamine compounds of the present invention; preferably, the first hole transport layer comprises at least one of the fluorene-containing triarylamine compounds of the present invention; preferably, the second hole transport layer contains at least one of the fluorene-containing triarylamine compounds according to the present invention; preferably, the third hole transport layer contains at least one of the fluorene-containing triarylamine compounds according to the present invention; preferably, at least one of the fluorene-containing triarylamine compounds of the present invention is contained in the first hole transport layer and the third hole transport layer; preferably, at least one of the fluorene-containing triarylamine compound according to the present invention is contained in the second hole transport layer and the third hole transport layer; preferably, at least one of the fluorene-containing triarylamine compound according to the present invention is contained in the first hole transport layer, the second hole transport layer, and the third hole transport layer.
Preferably, the organic layer is located on one side of the cathode away from the anode, and the organic layer comprises a cover layer, and the cover layer contains at least one of the fluorene-containing triarylamine compounds according to the present invention.
Preferably, the cover layer of the present invention may have a single-layer structure, a two-layer structure or a multi-layer structure, and the cover layer material of the present invention is at least one selected from the fluorene-containing triarylamine compounds of the present invention.
The anode material of the present invention is preferably a material having a high work function. The anode may 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 may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2 ) Zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may have a single-layer structure of Al or a three-layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
The hole injection layer material, preferably a material with a high work function, can be selected from any one or more of the following structures: metalloporphyrins, oligothiophenes, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto, as the hole transport layer of the present invention, materials having high hole mobility are preferable. Specific examples thereof include materials such as diphenylamines, fluorenes, carbazoles, biphenyldiamines, etc., and examples thereof include N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4'4 "-tris (N, N-diphenylamino) triphenylamine (TDATA), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4',4" -tris (carbazol-9-yl) triphenylamine (TCTA), etc., but are not limited thereto.
The hole transport layer material of the present invention, in addition to the fluorene-containing triarylamine compound of the present invention, is preferably a material having high hole mobility, and may be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanines, hexanitrile hexaazabenzophenanthrenes, quinacridones, anthraquinones, polyanilines, polythiophenes, polyvinylcarbazoles, and the like, but are not limited thereto.
The light-emitting layer material of the present invention may be a red, green or blue light-emitting material, and generally comprises a guest (doped) material and a host material, wherein the guest material may be a simple fluorescent material or a phosphorescent material, or may be a combination of fluorescent and phosphorescent materials. The host material of the light-emitting layer needs to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and examples thereof include distyrylaryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives. The guest material may be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but are not limited thereto.
The hole blocking layer material is generally preferably a material capable of effectively blocking holes, and can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, and the like, but are not limited thereto.
The electron transport layer material, preferably a material with high electron mobility, according to the present invention may be selected from any one or more of the following structures: the metal chelate compound, the oxaoxazole derivative, the thiazole derivative, the diazole derivative, the azabenzene derivative, the diazene derivative, the silicon-containing heterocyclic compound, the boron-containing heterocyclic compound, the cyano compound, the quinoline derivative, the phenanthroline derivative, the benzimidazole derivative, and the like are not limited thereto, and may be a single structure composed of a single substance, a single layer structure or a multilayer structure composed of different substances.
The electron injection layer material, preferably a material with a low work function, can be selected from any one or more of the following structures: a metal, an alkali metal, an alkaline earth metal, an alkali metal halide, an alkaline earth metal halide, an alkali metal oxide, an alkaline earth metal oxide, an alkali metal salt, an alkaline earth metal salt, a metal complex, or other substances having high electron injection properties. Examples can be cited as Li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, and the like, but is not limited thereto.
The cathode material according to the present invention, preferably a material having a low work function, may be selected from transmissive electrodes, semi-reflective electrodes or reflective electrodes. When the cathode is a transmissive electrode, the material used to form the cathode may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.
The coating layer material of the present invention is preferably a material having an optical coupling effect, in addition to the fluorene-containing triarylamine compound of the present invention. Specific examples canComprising the following steps: examples of the metal halide, metal oxide, metal nitride, aromatic amine derivative, carbazole derivative, oxazole derivative and the like include LiF, csF, mgF 2 、CaF 2 、CsCl、CuI、V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、Alq 3 But is not limited thereto.
The organic layers, the cathode, the anode and the cover layer can be prepared by any one method of vacuum evaporation, ink-jet printing, sputtering, plasma, spin coating, dipping and screen printing, and the thickness of each layer is not particularly limited, so that good device performance can be obtained. Each of the organic layers described above is preferably prepared using a method of vacuum evaporation, inkjet printing, or spin coating, but is not limited thereto.
The organic electroluminescent device is mainly applied to the technical field of information display, and is widely applied to various information displays in the aspect of information display, such as a tablet personal computer, a flat television, a mobile phone, a smart watch, a digital camera, VR, a vehicle-mounted system, wearable equipment and the like.
The following is one preparation method of the compound represented by the formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compounds of formula I may be prepared by the reaction schemes shown below, using conventional methods well known to those skilled in the art. The main reaction type involved in the invention is Suzuki coupling reaction and Miyaura boric acid esterification reaction.
Synthetic examples
Preparation of the compound of formula I:
the X is 1 ～X 2 Each is independently selected from any one of I, br and Cl; ar to Ar are as described above 2 、L 0 ～L 2 、R 0 ～R 1 、n 0 ～n 1 The definition of (2) is the same as the definition described above.
Raw materials and reagents:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and the reagents used in the invention are all reagent pure.
Instrument:
the mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;
synthesis example 1: preparation of raw material c-115
Into a reaction flask were charged n-115 (13.79 g,70.00 mmol), m-115 (14.45 g,70.00 mmol), pd (PPh) under nitrogen 3 ) 4 (0.81 g,0.70 mmol) and K 2 CO 3 (19.35 g,140.00 mmol) and 400mL of toluene/ethanol/water (2:1:1) mixed solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 5h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected and dried over anhydrous magnesium sulfate, filtration was performed, the filtrate was concentrated by distillation under reduced pressure, and recrystallization was performed with toluene, and the material c-115 (16.39 g, yield 84%) was obtained after drying, and the purity of the solid was not less than 99.72% by HPLC detection. Mass spectrum m/z:278.0486 (theory: 278.0498).
The raw materials were replaced correspondingly, and the raw materials c were prepared according to the preparation method of the raw materials c-115 in synthetic example 1, and the raw materials are shown in the following table:
synthesis example 2: preparation of Compound 17
Preparation of intermediate A-17:
a-17 (4.66 g,50.00 mmol), b-17 (26.58 g,50.00 mmol), pd (OAc) were added to the flask under nitrogen 2 (0.13g，0.60mmol)、P(t-Bu) 3 (2.00 mL of a 0.5M toluene solution, 1.00 mmol), naOt-Bu (9.61 g,100.00 mmol) and 300mL of toluene solvent, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected and dried over anhydrous magnesium sulfate, filtration was performed, the filtrate was concentrated by distillation under reduced pressure, and recrystallization was performed with toluene/ethanol (4:1) to obtain intermediate A-17 (21.75 g, yield 80%) with HPLC purity of 99.86%. Mass spectrum m/z:543.2916 (theory: 543.2926).
Preparation of compound 17:
the reaction flask was charged with intermediate A-17 (19.80 g,30.00 mmol), c-17 (4.71 g,30.00 mmol), pd under nitrogen 2 (dba) 3 (0.37 g,0.40 mmol), X-Phos (0.38 g,0.80 mmol), naOt-Bu (5.77 g,60.00 mmol) and 200ml toluene solvent, the mixture was stirred, and the mixture of the above reactants was heated under reflux for 7h. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, and recrystallizing with toluene to obtain compound 17 (16.32 g, 74%) with HPLC purity of > 99.96%. Mass spectrum m/z:735.3514 (theory: 735.3501). Theoretical element content (%) C 55 H 45 NO: c,89.76; h,6.16; n,1.90. Measured element content (%): c,89.72; h,6.18; n,1.93.
Synthesis example 3: preparation of Compound 25
The same preparation as in Synthesis example 2 was repeated except that b-17 was replaced with equimolar b-25 and c-17 was replaced with equimolar c-25 to obtain Compound 25 (16.06 g), and the purity of the solid was ≡ 99.93% by HPLC. Mass spectrum m/z:753.3021 (theory: 753.3032). Theoretical element content (%) C 57 H 39 NO: c,90.81; h,5.21; n,1.86. Measured element content (%): c,90.85; h,5.23; n,1.82.
Synthesis example 4: preparation of Compound 54
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-54 and b-17 was replaced with equimolar b-54 to obtain compound 54 (14.64 g), and the purity of the solid was ≡ 99.96% by HPLC. Mass spectrum m/z:677.2727 (theory: 677.2719). Theoretical element content (%) C 51 H 35 NO: c,90.37; h,5.20; n,2.07. Measured element content (%): c,90.34; h,5.24; n,2.05.
Synthesis example 5: preparation of Compound 57
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-54, b-17 was replaced with equimolar b-57, and c-17 was replaced with equimolar c-57 to obtain compound 57 (16.35 g), and the purity of the solid was ≡ 99.92% by HPLC detection. Mass spectrum m/z:789.3989 (theory: 789.3971). Theoretical element content (%) C 59 H 51 NO: c,89.70; h,6.51; n,1.77. Measured element content (%): c,89.73; h,6.54; n,1.73.
Synthesis example 6: preparation of Compound 75
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-75 and b-17 was replaced with equimolar b-75 to obtain Compound 75 (16.35 g), and the purity of the solid was ≡ 99.95% by HPLC. Mass spectrum m/z:686.3273 (theory: 686.3284). Theoretical element content (%) C 51 H 26 D 9 NO: c,89.18; h,6.45; n,2.04. Measured element content (%): c,89.15; h,6.43; n,2.07.
Synthesis example 7: preparation of Compound 80
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-80 and b-17 was replaced with equimolar b-54 to obtain Compound 80 (16.43 g), and the purity of the solid was ≡ 99.97% by HPLC. Mass spectrum m/z:749.3128 (theory: 749.3114). Theoretical element content (%) C 54 H 43 NOSi: c,86.48; h,5.78; n,1.87. Measured element content (%): c,86.44; h,5.76; n,1.93.
Synthesis example 8: preparation of Compound 85
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-85, b-17 was replaced with equimolar b-85, and c-17 was replaced with equimolar c-85 to obtain Compound 85 (15.66 g), and the purity of the solid was ≡ 99.92% by HPLC. Mass spectrum m/z:790.3939 (theory: 790.3923). Theoretical element content (%) C 58 H 50 N 2 O: c,88.06; h,6.37; n,3.54. Measured element content (%): c,88.09; h,6.34; n,3.58.
Synthesis example 9: preparation of Compound 88
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-88, b-17 was replaced with equimolar b-88, and c-17 was replaced with equimolar c-88 to obtain compound 88 (13.93 g), and the purity of the solid was ≡ 99.94% by HPLC. Mass spectrum m/z:682.3020 (theory: 682.3032). Theoretical element content (%) C 51 H 30 D 5 NO: c,89.70; h,5.90; n,2.05. Measured element content (%): c,89.73; h,5.93; n,2.01.
Synthesis example 10: preparation of Compound 91
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-54, b-17 was replaced with equimolar b-91, and c-17 was replaced with equimolar c-91 to obtain Compound 91 (13.66 g), and the purity of the solid was ≡ 99.95% by HPLC detection. Mass spectrum m/z:679.2607 (theory: 679.2624). Theoretical element content (%) C 49 H 33 N 3 O: c,86.57; h,4.89; n,6.18. Measured element content (%): c,86.54; h,4.92; n,6.15.
Synthesis example 11: preparation of Compound 104
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-104, b-17 was replaced with equimolar b-54, and c-17 was replaced with equimolar c-88 to obtain compound 104 (16.14 g), and the purity of the solid was ≡ 99.93% by HPLC. Mass spectrum m/z:677.2730 (theory: 677.2719). Theoretical element content (%) C 51 H 35 NO: c,90.37; h,5.20; n,2.07. Measured element content (%): c,90.34; h,5.26; n,2.03.
Synthesis example 12: preparation of Compound 115
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-115, b-17 was replaced with equimolar b-115, and c-17 was replaced with equimolar c-115, to obtain compound 115 (15.16 g), and the purity of the solid was ≡ 99.97% by HPLC. Mass spectrum m/z:701.2738 (theory: 701.2719). Theoretical element content (%) C 53 H 35 NO: c,90.70; h,5.03; n,2.00. Measured element content (%): c,90.67; h,5.06; n,1.96.
Synthesis example 13: preparation of Compound 124
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-124, b-17 was replaced with equimolar b-124, and c-17 was replaced with equimolar c-88 to obtain Compound 124 (16.77 g), and the purity of the solid was ≡ 99.92% by HPLC. Mass spectrum m/z:833.3101 (theory: 833.3114). Theoretical element content (%) C 61 H 43 NOSi: c,87.84; h,5.20; n,1.68. Measured element content (%): c,87.81; h,5.16; n,1.71.
Synthesis example 14: preparation of Compound 129
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-129 and b-17 was replaced with equimolar b-129 to obtain compound 129 (17.14 g), and the purity of the solid was ≡ 99.95% by HPLC. Mass spectrum m/z:771.3510 (theory: 771.3501). Theoretical element content (%) C 58 H 45 NO: c,90.24; h,5.88; n,1.81. Measured element content (%): c,90.27; h,5.92; n,1.78.
Synthesis example 15: preparation of Compound 136
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-136 and b-17 was replaced with equimolar b-54 to obtain compound 136 (15.51 g), and the purity of the solid was ≡ 99.93% by HPLC. Mass spectrum m/z:717.3017 (theory: 717.3032). Theoretical element content (%) C 54 H 39 NO: c,90.34; h,5.48; n,1.95. Measured element content (%): c,90.32; h,5.53; n,1.92.
Synthesis example 16: preparation of Compound 140
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-136, b-17 was replaced with equimolar b-54, and c-17 was replaced with equimolar c-140 to obtain compound 140 (15.16 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:721.3292 (theory: 721.3283). Theoretical element content (%) C 54 H 35 D 4 NO: c,89.84; h,6.00; n,1.94. Measured element content (%): c,89.87; h,5.96; n,1.98.
Synthesis example 17: preparation of Compound 142
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-142, b-17 was replaced with equimolar b-54, and c-17 was replaced with equimolar c-142 to obtain compound 142 (16.62 g), and the purity of the solid was ≡ 99.93% by HPLC. Mass spectrum m/z:851.4139 (theory: 851.4127). Theoretical element content (%) C 64 H 53 NO: c,90.21; h,6.27; n,1.64. Measured element content (%): c,90.18; h,6.31; n,1.67.
Synthesis example 18: preparation of Compound 171
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-171, b-17 was replaced with equimolar b-75, and c-17 was replaced with equimolar c-171 to obtain compound 171 (18.09 g), and the purity of the solid was ≡ 99.97% by HPLC. Mass spectrum m/z:873.3957 (theory: 873.3971). Theoretical element content (%) C 66 H 51 NO: c,90.69; h,5.88; n,1.60. Measured element content (%): c,90.73; h,5.85; n,1.63.
Synthesis example 19: preparation of Compound 172
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The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-172, b-17 was replaced with equimolar b-172, and c-17 was replaced with equimolar c-172, to obtain compound 172 (15.22 g), and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:745.3355 (theory: 745.3345). Theoretical element content (%) C 56 H 43 NO: c,90.17; h,5.81; n,1.88. Measured element content (%): c,90.20; h,5.78; n,1.93.
Synthesis example 20: preparation of Compound 201
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-201 and b-17 was replaced with equimolar b-54 to obtain compound 201 (16.93 g), and the purity of the solid was ≡ 99.96% by HPLC. Mass spectrum m/z:841.3325 (theory: 841.3345). Theoretical element content (%) C 64 H 43 NO: c,91.29; h,5.15; n,1.66. Measured element content (%): c,91.32; h,5.13; n,1.69.
Synthesis example 21: preparation of Compound 220
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-220, b-17 was replaced with equimolar b-75, and c-17 was replaced with equimolar c-142 to obtain compound 220 (18.10 g), and the purity of the solid was ≡ 99.92% by HPLC. Mass spectrum m/z:913.3752 (theory: 913.3740). Theoretical element content (%) C 67 H 51 NOSi: c,88.02; h,5.62; n,1.53. Measured element content (%): c,88.06; h,5.58; n,1.57.
Synthesis example 22: preparation of Compound 256
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-256 and b-17 was replaced with equimolar b-54 to obtain compound 256 (18.40 g), and the purity of the solid was ≡ 99.94% by HPLC. Mass spectrum m/z:839.3173 (theory: 839.3188). Theoretical element content (%) C 64 H 41 NO: c,91.51; h,4.92; n,1.67. Measured element content (%): c,91.47; h,4.96; n,1.63.
Synthesis example 23: preparation of Compound 262
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-262, b-17 was replaced with equimolar b-262 and c-17 was replaced with equimolar c-142 to obtain compound 262 (18.85 g), and the purity of the solid was ≡ 99.92% by HPLC detection. Mass spectrum m/z:951.4424 (theory: 951.4440). Theoretical element content (%) C 72 H 57 NO: c,90.82; h,6.03; n,1.47. Measured element content (%): c,90.79; h,6.07; n,1.42.
Synthesis example 24: preparation of Compound 301
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-136, b-17 was replaced with equimolar b-75, and c-17 was replaced with equimolar c-301 to obtain Compound 301 (16.03 g), and the purity of the solid was ≡ 99.93% by HPLC detection. Mass spectrum m/z:741.3049 (theory: 741.3032). Theoretical element content (%) C 56 H 39 NO: c,90.66; h,5.30; n,1.89. Measured element content (%): c,90.70; h,5.33; n,1.85.
Synthesis example 25: preparation of Compound 317
The same preparation as in Synthesis example 2 was repeated except that b-17 was replaced with equimolar b-317 and c-17 was replaced with equimolar c-317 to obtain compound 317 (13.42 g), and the purity of the solid was ≡ 99.96% by HPLC. Mass spectrum m/z:667.2327 (theory: 667.2334). Theoretical element content (%) C 49 H 33 NS: c,88.12; h,4.98; n,2.10. Measured element content (%): c,88.08; h,5.01; n,2.14.
Synthesis example 26: preparation of Compound 324
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-324, b-17 was replaced with equimolar b-54, and c-17 was replaced with equimolar c-324 to obtain compound 324 (13.10 g), and the purity of the solid was ≡ 99.95% by HPLC detection. Mass spectrum m/z:661.2571 (theory: 661.2552). Theoretical element content (%) C 46 H 35 N 3 S: c,83.48; h,5.33; n,6.35. Measured element content (%): c,83.52; h,5.29; n,6.38.
Synthesis example 27: preparation of Compound 337
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-337, b-17 was replaced with equimolar b-337, and c-17 was replaced with equimolar c-337 to obtain compound 337 (14.01 g), and the purity of the solid was ≡ 99.93% by HPLC. Mass spectrum m/z:676.2888 (theory: 676.2899). Theoretical element content (%) C 49 H 24 D 9 NS: c,86.94; h,6.25; n,2.07. Measured element content (%): c,86.97; h,6.28; n,2.03.
Synthesis example 28: preparation of Compound 355
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-355, b-17 was replaced with equimolar b-355, and c-17 was replaced with equimolar c-355, to obtain compound 355 (17.39 g), and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:827.3578 (theory: 827.3586). Theoretical element content (%) C 61 H 49 NS: c,88.47; h,5.96; n,1.69. Measured element content (%): c,88.52; h,5.98; n,1.65.
Synthesis example 29: preparation of Compound 360
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-360, b-17 was replaced with equimolar b-360, and c-17 was replaced with equimolar c-360, to obtain Compound 360 (15.46 g), and the purity of the solid was ≡ 99.91% by HPLC. Mass spectrum m/z:792.2609 (theory: 792.2599). Theoretical element content (%) C 58 H 36 N 2 S：C,87.85；H,4.58；N,3.53。Measured element content (%): c,87.90; h,4.55; n,3.56.
Synthesis example 30: preparation of Compound 380
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-380, b-17 was replaced with equimolar b-380, and c-17 was replaced with equimolar c-317 to obtain compound 380 (14.25 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:719.2382 (theory: 719.2395). Theoretical element content (%) C 51 H 33 N 3 S: c,85.09; h,4.62; n,5.84. Measured element content (%): c,85.14; h,4.65; n,5.80.
Synthesis example 31: preparation of Compound 392
The same procedures as in Synthesis example 2 were repeated except for substituting a-17 with equimolar a-136, substituting b-17 with equimolar b-392 and substituting c-17 with equimolar c-392 to give compound 392 (16.77 g), whose solid purity was ≡ 99.94% by HPLC. Mass spectrum m/z:833.3109 (theory: 833.3116). Theoretical element content (%) C 62 H 43 NS: c,89.28; h,5.20; n,1.68. Measured element content (%): c,89.24; h,5.16; n,1.71.
Synthesis example 32: preparation of Compound 394
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-394, b-17 was replaced with equimolar b-394 and c-17 was replaced with equimolar c-355 to obtain compound 394 (16.40 g), and the purity of the solid was ≡ 99.91% by HPLC detection. Mass spectrum m/z:748.3857 (theory: 748.3869). Theoretical element content (% )C 54 H 40 D 7 NS: c,86.59; h,7.26; n,1.87. Measured element content (%): c,86.64; h,7.23; n,1.91.
Synthesis example 33: preparation of Compound 416
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-416, b-17 was replaced with equimolar b-416, and c-17 was replaced with equimolar c-355 to obtain compound 416 (17.76 g), and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:857.3125 (theory: 857.3116). Theoretical element content (%) C 64 H 43 NS: c,89.58; h,5.05; n,1.63. Measured element content (%): c,89.62; h,5.02; n,1.66.
Synthesis example 34: preparation of Compound 456
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-456, b-17 was replaced with equimolar b-456, and c-17 was replaced with equimolar c-317 to obtain compound 456 (18.59 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:967.4230 (theory: 967.4212). Theoretical element content (%) C 72 H 57 NS: c,89.31; h,5.93; n,1.45. Measured element content (%): c,89.26; h,5.96; n,1.42.
Synthesis example 35: preparation of Compound 468
The same preparation as in Synthesis example 2 was repeated except that b-17 was replaced with equimolar b-468 and c-17 was replaced with equimolar c-468 to obtain compound 468 (13.42 g), and the purity of the solid was ≡ 99.91% by HPLC. Mass spectrum m/z:677.2823 (theoretical value: 67) 7.2831). Theoretical element content (%) C 50 H 35 N 3 : c,88.60; h,5.20; n,6.20. Measured element content (%): c,88.55; h,5.23; n,6.16.
Synthesis example 36: preparation of Compound 470
The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-470, b-17 was replaced with equimolar b-470 and c-17 was replaced with equimolar c-470 to obtain compound 470 (17.72 g), and the purity of the solid was ≡ 99.95% by HPLC. Mass spectrum m/z:808.3801 (theory: 808.3817). Theoretical element content (%) C 61 H 48 N 2 : c,90.56; h,5.98; n,3.46. Measured element content (%): c,90.60; h,5.94; n,3.49.
Synthesis example 37: preparation of Compound 514
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The same preparation as in Synthesis example 2 was repeated except that a-17 was replaced with equimolar a-514, b-17 was replaced with equimolar b-514, and c-17 was replaced with equimolar c-514 to obtain compound 514 (17.19 g), and the purity of the solid was ≡ 99.97% by HPLC. Mass spectrum m/z:806.3680 (theory: 806.3661). Theoretical element content (%) C 61 H 46 N 2 : c,90.78; h,5.75; n,3.47. Measured element content (%): c,90.82; h,5.72; n,3.51.
Device embodiment
In the invention, an ITO glass substrate is ultrasonically cleaned by 5% glass cleaning liquid for 2 times, 20 minutes each time, and then by deionized water for 2 times, 10 minutes each time. After the distilled water is washed, sequentially ultrasonic washing is carried out for 20 minutes by using solvents such as acetone, isopropyl alcohol, methanol and the like, and the distilled water is dried at 120 ℃ and then is sent into a vapor deposition machine.
Test software, a computer, a K2400 digital source list manufactured by Keithley company in U.S. and a PR788 spectrum scanning luminance meter manufactured by Photoresearch company in U.S. are combined into a combined IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
The preparation of the device is completed by adopting a vacuum evaporation system and continuously evaporating under the condition of continuous vacuum. The materials are respectively arranged in quartz crucibles of different evaporation sources, and the temperature of the evaporation sources can be controlled independently. Placing the processed glass substrate into an OLED vacuum coating machine, wherein the vacuum degree of the system should be maintained at 5×10 during the film manufacturing process -5 Under Pa, the organic layer and the metal electrode were vapor deposited by replacing the mask plate, the vapor deposition rate was detected by using an Infinion SQM160 quartz crystal film thickness detector, and the film thickness was detected by using a quartz crystal oscillator.
Device example 1: preparation of organic electroluminescent device 1
ITO/Ag/ITO is used as an anode on a glass substrate; vacuum evaporating HI-1 on the anode to form a hole injection layer, wherein the evaporating thickness is 70nm; vacuum evaporating the compound 17 as a hole transport layer, wherein the thickness of the hole transport layer is 50nm; vacuum evaporating a main material GH and a doping substance GD (mass ratio is 92:8) on the hole transport layer to serve as a light-emitting layer, wherein the thickness of the light-emitting layer is 50nm; then vacuum evaporating ET-1 and Liq on the luminescent layer as electron transport layers (mass ratio is 1:1), wherein the thickness is 35nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.2nm; vacuum evaporating cathode Mg on the electron injection layer: ag (15 nm). Subsequently, CP-1 was evaporated on the cathode as a coating layer (55 nm) to prepare an organic electroluminescent device.
Examples 2 to 36: preparation of organic electroluminescent devices 2 to 36
The hole transport layers of example 1 were each replaced with a compound 25, a compound 54, a compound 57, a compound 75, a compound 80, a compound 85, a compound 88, a compound 91, a compound 104, a compound 115, a compound 124, a compound 129, a compound 136, a compound 140, a compound 142, a compound 171, a compound 172, a compound 201, a compound 220, a compound 256, a compound 262, a compound 301, a compound 317, a compound 324, a compound 337, a compound 355, a compound 360, a compound 380, a compound 392, a compound 394, a compound 416, a compound 456, a compound 468, a compound 470, a compound 514, and the other steps were the same, to obtain organic electroluminescent devices 2 to 36.
Comparative examples 1 to 4: preparation of comparative organic electroluminescent devices 1 to 4
The comparative organic electroluminescent devices 1 to 4 were obtained by changing the compound 17 in the hole transport layer of example 1 to the comparative compounds R-1, R-2, R-3 and R-4, respectively, in the same manner.
The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 1 to 36 and comparative examples 1 to 4 according to the present invention are shown in table 1.
Table 1 luminescence characteristic test data of organic electroluminescent device:
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as can be seen from the results in Table 1, when the fluorene-containing triarylamine compound of the present invention is used as a hole transport layer material of an organic electroluminescent device, the fluorene-containing triarylamine compound has a suitable HOMO orbital energy level, and can effectively ensure effective injection and transport of holes between the electrode and the organic layer and between the electrode and the organic layer interface; in addition, the compound has good mobility, film forming property and thermal stability, and can effectively improve the efficiency and service life of the device. The triarylamine compound containing fluorene is an OLEDs hole transport layer material with excellent performance.
Device example 37: preparation of organic electroluminescent device 37
ITO/Ag/ITO is used as an anode on a glass substrate; vacuum evaporating HI-1 on the anode to form a hole injection layer, wherein the evaporating thickness is 70nm; vacuum evaporation HT is carried out on the hole injection layer to serve as a first hole transport layer, and the thickness is 50nm; vacuum evaporating the compound 17 as a second hole transport layer with the thickness of 65nm on the first hole transport layer; vacuum evaporating a main material GH and a doping substance GD (mass ratio of 92:8) on the second hole transport layer to form a light-emitting layer, wherein the thickness of the light-emitting layer is 50nm; then vacuum evaporating ET-1 and Liq on the luminescent layer as electron transport layers (mass ratio is 1:1), wherein the thickness is 35nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.2nm; vacuum evaporating cathode Mg on the electron injection layer: ag (15 nm). Subsequently, CP-1 was evaporated on the cathode as a coating layer (55 nm) to prepare an organic electroluminescent device.
Examples 38 to 72: preparation of organic electroluminescent devices 38-72
The organic electroluminescent devices 38 to 72 were obtained by replacing compound 17 in the second hole-transporting layer of example 37 with compound 25, compound 54, compound 57, compound 75, compound 80, compound 85, compound 88, compound 91, compound 104, compound 115, compound 124, compound 129, compound 136, compound 140, compound 142, compound 171, compound 172, compound 201, compound 220, compound 256, compound 262, compound 301, compound 317, compound 324, compound 337, compound 355, compound 360, compound 380, compound 392, compound 394, compound 416, compound 456, compound 468, compound 470 and compound 514, respectively, and the other steps being the same.
Comparative examples 5 to 8: preparation of comparative organic electroluminescent devices 5 to 8
The comparative organic electroluminescent devices 5 to 8 were obtained by changing the compound 17 in the second hole transport layer of example 37 to the comparative compounds R-1, R-2, R-3 and R-4, respectively, in the same manner.
The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 38 to 72 of the present invention and comparative examples 5 to 8 are shown in table 2.
Table 2 luminescence characteristic test data of organic electroluminescent device:
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as can be seen from the results in Table 2, when the fluorene-containing triarylamine compound of the present invention is used as a material for a second hole transport layer of an organic electroluminescent device, the fluorene-containing triarylamine compound has a suitable HOMO orbital level, and can effectively ensure effective injection and transport of holes between an electrode and an organic layer and between interfaces of the organic layer; in addition, the compound has good mobility, film forming property and thermal stability, and can effectively improve the efficiency and service life of the device. The triarylamine compound containing fluorene is an OLEDs second hole transport layer material with excellent performance.
Device example 73: preparation of organic electroluminescent device 73
ITO/Ag/ITO is used as an anode on a glass substrate; vacuum evaporating HI-2 on the anode to form a hole injection layer, wherein the evaporating thickness is 70nm; vacuum evaporating HT-1 on the hole injection layer as a first hole transport layer, wherein the thickness is 50nm; vacuum evaporating HT-2 on the first hole transport layer to serve as a second hole transport layer, wherein the thickness of the second hole transport layer is 65nm; vacuum evaporating a main material RH and a doping substance RD (the mass ratio is 92:8) on the second hole transport layer to serve as a light-emitting layer, wherein the thickness of the light-emitting layer is 50nm; then, carrying out vacuum evaporation on the ET-2 and Liq serving as electron transport layers (the mass ratio is 1:1) on the luminescent layer, wherein the thickness is 35nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.2nm; vacuum evaporating cathode Mg on the electron injection layer: ag (15 nm). Subsequently, the compound 17 of the present invention was evaporated as a coating layer (55 nm) on a cathode to prepare an organic electroluminescent device.
Examples 74 to 108: preparation of organic electroluminescent devices 74-108
The organic electroluminescent devices 74 to 108 were obtained by replacing compound 17 in the cap layer of example 73 with compound 25, compound 54, compound 57, compound 75, compound 80, compound 85, compound 88, compound 91, compound 104, compound 115, compound 124, compound 129, compound 136, compound 140, compound 142, compound 171, compound 172, compound 201, compound 220, compound 256, compound 262, compound 301, compound 317, compound 324, compound 337, compound 355, compound 360, compound 380, compound 392, compound 394, compound 416, compound 456, compound 468, compound 470 and compound 514, respectively, and the other steps being the same.
Comparative examples 9 to 10: preparation of contrast organic electroluminescent devices 9 to 10
The compound 17 in the coating layer of example 73 was changed to the comparative compounds C-1 and C-2, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 9 to 10.
The results of the light emitting characteristics test of the organic electroluminescent devices prepared in examples 73 to 108 of the present invention and comparative examples 9 to 10 are shown in table 3.
Table 3 luminescence characteristic test data of organic electroluminescent device:
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as can be seen from the results in Table 3, when the fluorene-containing triarylamine compound of the present invention is used as a material for a cover layer of an organic electroluminescent device, the fluorene-containing triarylamine compound has good thermal conductivity, light transmittance and corrosion resistance; in addition, the structure has certain steric hindrance, the material is not easy to crystallize after being heated and cooled, the chemical property is stable, and the light extraction efficiency can be effectively improved. The fluorene-containing triarylamine compound is an OLEDs coating material with excellent performance.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (10)

1. The fluorene-containing triarylamine compound is characterized by having a general structural formula shown in formula 1:
the R is 0 、R 1 Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said n 0 Selected from 0, 1, 2, 3 or 4; when n is 0 Above 1, two or more R 0 Are identical or different from each other, or adjacent two R 0 Are connected with each other to form a substituted or unsubstituted ring;
said n 1 Selected from 0, 1, 2, 3 or 4; when n is 1 Above 1, two or more R 1 Are identical or different from each other, or adjacent two R 1 Are connected with each otherForming a substituted or unsubstituted ring;
the Ar is selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of C6-C60, a substituted or unsubstituted heteroaryl group of C2-C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and an aromatic ring of C6-C60, and a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C60 and a heteroaromatic ring of C2-C30;
the Ar is as follows 1 Any one or a combination of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C30 alicyclic ring, and a condensed ring group of a C6-C60 aromatic ring;
the Ar is as follows 2 Selected from the group represented by formula 1-a or 1-b, wherein the ring A is selected from any one of C6-C30 aryl, C2-C30 heteroaryl;
The X is selected from O, S or N (R) a )；
The Y is independently selected from O or S;
each z is independently selected from CH or N; z fused to ring a is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the L is 0 Selected from the group consisting of a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 or a combination thereof;
the L is 1 、L 2 Each independently selected from one or a combination of a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60;
The X is selected from N (R) a ) When the L is 2 Not selected from single bonds.
2. The fluorene-containing triarylamine compound according to claim 1, wherein Ar is selected from any one of the following groups or a combination thereof:
each t is independently selected from CH or N;
the Y is 1 Selected from O, S or N (R) b )；
The Y is 2 Selected from CH or N;
the Y is 3 Independently selected from O or S;
the Y is 4 Selected from O, S, C (R) c R d )、N(R e ) Any one of them;
the R is b 、R e Each independently selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is c 、R d Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted cycloalkyl of C3-C30, substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C2-C30, fused ring group of substituted or unsubstituted alicyclic ring of C3-C30 and aromatic ring of C6-C30, fused ring group of substituted or unsubstituted alicyclic ring of C3-C30 and heteroaromatic ring of C2-C30, or R c 、R d Form a substituted or unsubstituted ring;
the R is 2 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 2 Are connected with each other to form a substituted or unsubstituted ring;
the a 1 Selected from 0, 1, 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3, 4 or 5.
3. The fluorene-containing triarylamine compound according to claim 1, wherein Ar is selected from any one of the following groups or a combination thereof:
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is m Each independently selectFrom any of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring fused ring group, or R m Form a substituted or unsubstituted ring;
the R is 2 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and aromatic ring of C6-C30, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and heteroaromatic ring of C2-C30, or adjacent two R 2 Are connected with each other to form a substituted or unsubstituted ring;
the a 0 Selected from 0, 1 or 2; the a 1 Selected from 0, 1, 2, 3 or 4; the a 2 Selected from 0, 1, 2, 3, 4 or 5; the a 3 Selected from 0, 1, 2, 3, 4, 5 or 6; the a 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the a 6 Selected from 0, 1, 2 or 3; the a 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the a 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the a 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
4. The fluorene-containing triarylamine compound according to claim 1, wherein Ar 1 Any one or a combination of the following groups:
the R is f Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R f To form a substituted or unsubstituted carbocyclic ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said b 0 Selected from 0, 1, 2 or 3; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4 or 5; said b 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 7 Selected from 0, 1 or 2.
5. The fluorene-containing triarylamine compound according to claim 1, wherein Ar 1 Any one or a combination of the following groups:
the R is 3 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropyl, cyclobutanyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-tert-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphthyl, deutero-anthryl, deutero-phenanthryl, deutero-triphenylenyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthalene, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted biphenyl 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9 '-spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroesopropyl-substituted phenyl, deuteroesopropyl-substituted biphenyl, deuteroetert-butyl-substituted phenyl, deuteroeterbutyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylsubstituted phenyl, or two adjacent R' s 3 Are connected with each other to form a substituted or unsubstituted ring;
said b 0 Selected from 0, 1, 2 or 3; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4 or 5; said b 3 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said b 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b 7 Selected from 0, 1 or 2; said b 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
6. The fluorene-containing triarylamine compound according to claim 1, wherein Ar 2 Any one selected from the following groups:
each z is independently selected from CH or N;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring.
7. The fluorene-containing triarylamine compound according to claim 1, wherein said L 0 Selected from any one or a combination of the following groups 1 ～L 2 Each independently selected from a single bond or one or a combination of the groups shown below:
each r is independently selected from CH or N;
the Y is 5 Selected from O, S or N (R) x )；
The Y is 6 Selected from CH or N;
the Y is 7 Selected from O, S, C (R) p R q )、N(R z ) Any one of them;
the R is x 、R z Each independently selected from any one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, 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 C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is p 、R q Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30, a substituted or unsubstituted aryl group of C6-C30, a substituted or unsubstituted heteroaryl group of C2-C30, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and an aromatic ring of C6-C30, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and a heteroaromatic ring of C2-C30, or R p 、R q Form a substituted or unsubstituted ring;
the R is 4 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the X is selected from N (R) a ) When the L is 2 Not selected from single bonds;
said e 0 Selected from 0, 1 or 2; said e 1 Selected from 0, 1, 2, 3 or 4; said e 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 5 Selected from 0, 1, 2 or 3.
8. The fluorene-containing triarylamine compound according to claim 1, wherein said L 0 Selected from any one or a combination of the following groups 1 ～L 2 Each independently selected from a single bond or one or a combination of the groups shown below:
the R is n Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R n Form a substituted or unsubstituted ring;
the R is 5 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, F, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and aromatic ring of C6-C30, substituted or unsubstituted C3-C30 fused ring group of alicyclic ring and heteroaromatic ring of C2-C30, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
the X is selected from N (R) a ) When the L is 2 Not selected from single bonds;
said e 0 Selected from 0, 1 or 2; said e 1 Selected from 0, 1, 2, 3 or 4; said e 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 5 Selected from 0, 1, 2 or 3; said e 6 Selected from 0, 1, 2, 3, 4 or 5; said e 7 Selected from 0, 1, 2, 3, 4, 5, 6 or 7.
9. The fluorene-containing triarylamine compound according to claim 1, wherein the fluorene-containing triarylamine compound is selected from any one of the structures shown below:
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10. the invention also provides an organic electroluminescent device which comprises at least one of the fluorene-containing triarylamine compounds.
CN202311315435.0A 2023-10-11 2023-10-11 Fluorene-containing triarylamine compound and organic electroluminescent device thereof Pending CN117384120A (en)

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