CN113788759A - Triarylamine compound containing fluorene group and organic electroluminescent device thereof - Google Patents

Triarylamine compound containing fluorene group and organic electroluminescent device thereof Download PDF

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CN113788759A
CN113788759A CN202111095326.3A CN202111095326A CN113788759A CN 113788759 A CN113788759 A CN 113788759A CN 202111095326 A CN202111095326 A CN 202111095326A CN 113788759 A CN113788759 A CN 113788759A
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substituted
deuterated
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butyl
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CN113788759B (en
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杜明珠
孙敬
周雯庭
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound containing fluorene groups and an organic electroluminescent device thereof. The triarylamine compound containing fluorene groups provided by the invention has good hole mobility, proper HOMO energy level and T1 value, high glass transition temperature (Tg), good thermal stability, excellent intermolecular arrangement, difficult crystallization under the action of an external electric field, and good stability of film formation, and can be used as a hole transport material applied to an OLED device to improve the luminous efficiency of the device, reduce the driving voltage of the device and prolong the service life of the device. In addition, the triarylamine compound containing fluorene groups also has higher refractive index, and can be applied to OLED devices as a covering layer, so that the luminous efficiency and the service life of the devices are improved. In conclusion, the triarylamine compound containing fluorene group provided by the invention is an OLED material with excellent performance and wide application.

Description

Triarylamine compound containing fluorene group and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound containing fluorene groups and an organic electroluminescent device thereof.
Background
Organic Light-Emitting diodes (OLEDs) are considered to be one of the most developed display technologies, and compared with conventional liquid crystal displays (LEDs), the Organic Light-Emitting diodes have the advantages of small thickness, Light weight, wide viewing angle, short response time, wide temperature range, low energy consumption, high efficiency, good color purity, flexibility and the like, and are widely used in the fields of illumination and display.
The OLED device is of a sandwich structure and comprises a cathode, an anode and an organic layer arranged between the cathode and the anode, wherein the organic layer can be further divided into a hole transmission area, an electron transmission area, a light emitting area and the like according to different functions. The mechanism of action is that under the action of an external electric field, holes and electrons are respectively injected from an anode and a cathode, enter a light-emitting region through a hole transmission region and an electron transmission region, are combined in the light-emitting region to generate excitons and release energy, the excitons migrate under the action of the electric field and transfer the energy to a luminescent substance in the light-emitting region, the electrons in luminescent substance molecules are transited from a ground state to an excited state and then return to the ground state from the excited state, and in the process, the energy is released in the form of light.
The hole transport region mainly plays a role in injecting and transporting holes, and can be subdivided into a hole injection layer, a hole transport layer, a light-emitting auxiliary layer and the like. Hole transport materials generally should have high hole mobility, good thermal stability, good film-forming properties, and appropriate energy levels. The aromatic amine compound is one of the most widely applied hole transport materials in the field of OLED at present, and the compound can well meet the properties of the hole transport materials, and the structure of the compound can be changed to different degrees, so that the hole transport materials with different functions can be obtained. For example, according to differences in properties such as the Highest Occupied Molecular Orbital (HOMO), triplet level (T1), hole injection ability, and hole transport ability of the aromatic amine compound, the aromatic amine compounds of different structures are applied to different organic layers, some of which are used for the hole transport layer, some of which are used for the hole injection layer, some of which are used for the light emission auxiliary layer, and some of which are used for a plurality of organic layers. The development of hole transport materials with excellent performance and wide application is a challenge for OLED workers.
In order to further improve the performance of the OLED device, a covering layer is further added on the side of the cathode away from the anode by those skilled in the art, so that the OLED device has a higher refractive index while isolating harmful factors such as air, moisture, ultraviolet rays and the like, thereby improving the light emitting efficiency and the service life of the device. However, the types of currently used cover materials having excellent performance and wide applications are limited, and development is urgently needed.
Disclosure of Invention
The invention provides a triarylamine compound containing fluorene groups, which has high hole mobility, good thermal stability, good film-forming property, appropriate energy level, high refractive index and a structure shown in a formula (I):
Figure BDA0003268999140000011
wherein A is selected from saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11;
b, C, E, F is independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl and substituted or unsubstituted phenanthryl;
ar is1One selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted sec-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group;
ar is2、Ar3Independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, -NR1R2In the formula (I), the R is1、R2Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted carbazolyl, when the number of the substituent groups in the substituted or unsubstituted phenyl is more than two, adjacent substituent groups can be connected to form one of substituted or unsubstituted saturated or unsaturated aliphatic ring of C3-C10 and substituted or unsubstituted benzene ring;
said L1～L3Independently selected from one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene and substituted or unsubstituted biphenylene.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer comprises a hole transmission area, a light-emitting layer and an electron transmission area, and the hole transmission area contains more than one of the triarylamine compounds containing fluorene groups.
The invention further provides an organic electroluminescent device which comprises an anode, a cathode, an organic layer arranged between the anode and the cathode, and a covering layer arranged on the side of the cathode, which is far away from the anode, wherein the covering layer contains more than one of the triarylamine compounds containing fluorene groups.
Has the advantages that:
the triarylamine compound containing fluorene group in the formula (I) provided by the invention has good hole mobility, proper HOMO energy level and T1 value, high glass transition temperature (Tg), good thermal stability, excellent arrangement among molecules, difficult crystallization under the action of an external electric field, and good film forming stability, and can be applied to OLED devices as a hole transport material, thereby improving the luminous efficiency of the devices, reducing the driving voltage of the devices, and prolonging the service life of the devices.
In addition, the triarylamine compound containing fluorene group in the formula (I) also has higher refractive index, and can be applied to OLED devices as a covering layer, so that the luminous efficiency and the service life of the devices are improved.
In conclusion, the triarylamine compound containing fluorene group provided by the invention is an OLED material with excellent performance and wide application.
Detailed Description
The following will clearly and completely describe the technical solutions of the specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
The alicyclic ring in the present invention refers to a cyclic hydrocarbon having aliphatic properties, and can be divided into saturated alicyclic rings and unsaturated alicyclic rings, for example, the saturated alicyclic rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornane, adamantane and the like, but are not limited thereto; the unsaturated aliphatic ring includes, but is not limited to, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like. The alicyclic ring may also be classified into monocyclic and polycyclic rings, for example, monocyclic rings include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclopropene, cycloheptene, etc., but are not limited thereto; the polycyclic ring may be further divided into two forms of a spiro ring in which two rings share one carbon atom and a bridged ring in which two carbon atoms on the ring are connected by a carbon bridge, and the rings are connected to each other to form a cage structure, which is also a polycyclic structure, and the commonly used polycyclic rings include norbornane, adamantane and the like, but are not limited thereto. The above alicyclic ring preferably has 3 to 15 carbon atoms. The alicyclic ring is more preferably cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopentene, cyclohexene, 1-adamantane, 2-adamantane, norbornane.
The straight-chain or branched alkyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a straight-chain or branched alkane molecule, and includes, but is not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and the like.
The cycloalkyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a cycloalkane molecule, and includes, but is not limited to, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a norbornyl group, an adamantyl group, and the like.
The straight-chain or branched alkenyl group in the present invention means a hydrocarbon group obtained by removing one hydrogen atom from a straight-chain or branched olefin molecule, and includes, but is not limited to, a vinyl group, an n-propenyl group, an isopropenyl group, an n-butenyl group, an isobutenyl group, a sec-butenyl group, and the like.
The cycloalkenyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a cycloolefin molecule, and includes, but is not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like.
The straight-chain or branched alkynyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a straight-chain or branched alkyne molecule, and includes, but is not limited to, ethynyl, n-propynyl, n-butynyl, and the like.
The cycloalkynyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a molecule of cycloalkyne, such as, but not limited to, cyclopropynyl, cyclobutynyl, cyclopentynyl, cyclohexynyl, cycloheptynyl, and the like.
Alkoxy in the context of the present invention means-O-alkyl, wherein alkyl is as previously defined.
The term "alicyclic heterocyclic group" as used herein means a group formed by removing one hydrogen atom from an alicyclic heterocyclic molecule in which ring-constituting atoms contain at least one hetero atom in addition to carbon atoms, and the hetero atom includes a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, etc., preferably a nitrogen atom, an oxygen atom, a sulfur atom, and particularly preferably a nitrogen atom. Preferably 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. Preferably 3 to 15 atoms, more preferably 3 to 12 atoms, and particularly preferably 5 to 6 atoms. Examples may include ethylene oxide, ethylene sulfide, propylidene, tetrahydropyrrole, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl, and the like, but are not limited thereto. The above-mentioned lipid heterocyclic group is preferably tetrahydropyrrolyl, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl.
The aryl group in the present invention is a general term for the remaining groups of aromatic hydrocarbon molecules, from which one hydrogen atom is removed from one aromatic nucleus carbon, and may be a monocyclic aryl group or a condensed ring aryl group, wherein the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, etc., and the condensed ring aryl group may include a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a triphenylene group, etc., but is not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group in which one or more aromatic nuclear carbons in an aryl group are replaced with a heteroatom including, but not limited to, oxygen, sulfur or nitrogen atom, the heteroaryl group may be a monocyclic heteroaryl group or a fused ring heteroaryl group, the monocyclic heteroaryl group may be exemplified by pyridyl, pyrimidyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrrolyl and the like, the fused ring heteroaryl group may be exemplified by quinolyl, carbazolyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, benzopyrimidinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl and the like, but not limited thereto.
The aryloxy group in the present invention means an-O-aryl group, wherein the aryl group is as previously defined.
The "substitution" as referred to herein means that a hydrogen atom in some functional groups is replaced with another atom or functional group (i.e., substituent), and the substituted position is not limited as long as the position is a position at which a hydrogen atom is substituted, and when two or more are substituted, two or more substituents may be the same as or different from each other.
The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, halogen atom, amino group, cyano group, nitro group, substituted or unsubstituted C1 to C30 linear or branched alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C2 to C30 linear or branched alkenyl group, substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted linear or branched C2 to C30 alkynyl group, substituted or unsubstituted C30 to C30 cycloalkynyl group, substituted or unsubstituted C30 to C30 alkoxy group, substituted or unsubstituted C30 to C30 alicyclic group, substituted or unsubstituted C30 to C30 aryl group, substituted or unsubstituted C30 to C30 aryloxy group, substituted or unsubstituted C30 to C30 heteroaryl group, preferably deuterium atom, halogen atom, amino group, cyano group, nitro group, C30 to C30 linear or branched alkyl group, C30 to C30 cycloalkyl group, C30 to C30 branched C30 alkenyl group, or C30 to C30 branched cycloalkenyl group, A linear or branched alkynyl group having 2 to C12 carbon atoms, a cycloalkynyl group having 3 to C12 carbon atoms, an alkoxy group having 1 to C12 carbon atoms, an alicyclic heterocyclic group having 2 to C12 carbon atoms, an aryl group having 6 to C30 carbon atoms, and a heteroaryl group having 2 to C30 carbon atoms, wherein when the substituents are substituted with a plurality of groups, the substituents may be the same or different; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, chlorine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopropylalkyl group, cyclobutylalkyl group, cyclopentylalkyl group, cyclohexylalkyl group, cycloheptylalkyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, adamantyl group, norbornyl group, vinyl group, methoxy group, ethoxy group, tetrahydropyrrolyl group, piperidinyl group, morpholinyl group, thiomorpholinyl group, piperazinyl group, phenyl group, pentadeutenanth group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, dibenzofuranyl group, dibenzothienyl group, phenylcarbazolyl group, in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other.
In the present specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,
Figure BDA0003268999140000041
can represent
Figure BDA0003268999140000042
And so on.
The linking to form a ring structure according to the present invention means that the respective groups are linked to each other by a chemical bond, and optionally form a double bond, and may constitute an aromatic group, as exemplified below:
Figure BDA0003268999140000043
Figure BDA0003268999140000051
the invention provides a triarylamine compound containing fluorene groups, which has a structure shown in a formula (I):
Figure BDA0003268999140000052
wherein A is selected from saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11;
b, C, E, F is independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl and substituted or unsubstituted phenanthryl;
ar is1One selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted sec-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group;
ar is2、Ar3Independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, -NR1R2In the formula (I), the R is1、R2Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted carbazolyl, when the number of the substituent in the substituted or unsubstituted phenyl is more than two, adjacent two substituents can be connected to form substituted or unsubstituted saturated or saturated C3-C10One of an unsaturated aliphatic ring, a substituted or unsubstituted benzene ring;
said L1～L3Independently selected from one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene and substituted or unsubstituted biphenylene.
Preferably, the triarylamine compound containing a fluorene group has a structure represented by formula (II):
Figure BDA0003268999140000053
a, B, C, E, F, Ar as described1、Ar2、Ar3、L1～L3All as described above.
Preferably, the substituent in the "substituted or unsubstituted" is selected from the group consisting of deuterium atom, fluorine atom, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropyl group, deuterated cyclopropyl group, methyl-substituted cyclopropyl group, ethyl-substituted cyclopropyl group, cyclobutyl group, deuterated cyclobutyl group, methyl-substituted cyclobutyl group, ethyl-substituted cyclobutyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, ethyl-substituted cyclopentyl group, cyclohexyl group, deuterated cyclohexyl group, methyl-substituted cyclohexyl group, ethyl-substituted cyclohexyl group, n-propyl-substituted cyclohexyl group, n-butyl-substituted cyclohexyl group, cyclohexane-substituted cyclohexyl group, Vinyl, deuterated vinyl, cyclopentenyl, deuterated cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl.
Preferably, A is selected from one of the following structures:
Figure BDA0003268999140000061
wherein ". mark" represents a position where ring A shares a carbon atom with a five-membered carbocyclic ring;
a is selected from one of 0,1, 2,3 and 4, b is selected from one of 0,1 and 2, c is selected from one of 0,1, 2,3, 4,5 and 6, d is selected from one of 0,1, 2,3, 4,5, 6,7 and 8, e is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9 and 10, f is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13 and 14, g is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11 and 12, h is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13, 14, 15 and 16;
said R21Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropyl group, a deuterated cyclopropyl group, a methyl-substituted cyclopropyl group, an ethyl-substituted cyclopropyl group, a cyclobutyl group, a deuterated cyclobutyl group, a methyl-substituted cyclobutyl group, an ethyl-substituted cyclobutyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl groupThe cyclohexane group, the n-propyl group-substituted cyclohexane group, the n-butyl group-substituted cyclohexane group, the cyclohexane group-substituted cyclohexane group, the cyclopentenyl group, the deuterated cyclopentenyl group, the methyl group-substituted cyclopentenyl group, the ethyl group-substituted cyclopentenyl group, the cyclohexenyl group, the deuterated cyclohexenyl group, the adamantyl group, the deuterated adamantyl group, the methyl group-substituted adamantyl group, the ethyl group-substituted adamantyl group, the norbornyl group, the deuterated norbornyl group, the methyl group-substituted norbornyl group, the ethyl group-substituted norbornyl group, the tetrahydropyrrolyl group, the deuterated tetrahydropyrrolyl group, the piperidyl group, the deuterated piperidyl group, the morpholinyl group, the deuterated morpholinyl group, the thiomorpholinyl group, the deuterium-substituted thiomorpholinyl group, the methyl group-substituted piperazinyl group, the ethyl group-substituted piperazinyl group, the phenyl group-substituted piperazinyl group, the deuterated phenyl group-substituted piperazinyl group, the naphthyl group-substituted piperazinyl group, the deuterated naphthyl group-substituted piperazinyl group, One of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, when a plurality of R exist21They may be the same or different.
Preferably, R is21Selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, a n-propyl-substituted cyclohexyl group, a n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornylOne of alkyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, when a plurality of R exist21They may be the same or different.
Preferably, R is21Selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, a n-propyl-substituted cyclohexyl group, a n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, when a plurality of R's are present21They may be the same or different.
Preferably, R is21One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group and a deuterated tert-butyl group, when a plurality of R's are present21They may be the same or different.
Preferably, R is21One selected from hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl and deuterated ethyl, when a plurality of R exist21They may be the same or different.
Preferably, R is21Selected from hydrogen atoms or deuterium atoms.
Preferably, R is21Selected from hydrogen atoms.
Preferably, A is selected from one of the following structures:
Figure BDA0003268999140000081
preferably, the B, C, E, F is independently selected from one of the following structures:
Figure BDA0003268999140000082
wherein, the
Figure BDA0003268999140000083
Represents a position attached to a carbon atom on the five-membered carbon ring;
i is selected from one of 0,1, 2,3 and 4, j is selected from one of 0,1, 2,3, 4,5 and 6, and k is selected from one of 0,1, 2,3, 4,5, 6,7 and 8;
said R22Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, an n-propyl-substituted cyclohexyl group, an n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, a, First of allA group-substituted cyclopentenyl group, an ethyl-substituted cyclopentenyl group, a cyclohexenyl group, a deuterated cyclohexenyl group, an adamantyl group, a deuterated adamantyl group, a methyl-substituted adamantyl group, an ethyl-substituted adamantyl group, a norbornyl group, a deuterated norbornyl group, a methyl-substituted norbornyl group, an ethyl-substituted norbornyl group, a tetrahydropyrrolyl group, a deuterated tetrahydropyrrolyl group, a piperidinyl group, a deuterated piperidinyl group, a morpholinyl group, a deuterated morpholinyl group, a thiomorpholinyl group, a deuterated thiomorpholinyl group, a methyl-substituted piperazinyl group, an ethyl-substituted piperazinyl group, a phenyl-substituted piperazinyl group, a deuterated phenyl-substituted piperazinyl group, a naphthyl-substituted piperazinyl group, a deuterated naphthyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, when one of R's is present22They may be the same or different.
Preferably, R is22Selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, a n-propyl-substituted cyclohexyl group, a n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, when a plurality of R's are present22They may be the same or different.
Preferably, R is22One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group and a deuterated phenyl group, when a plurality of R's are present22They may be the same or different.
Preferably, the B, C, E, F is independently selected from one of the following structures:
Figure BDA0003268999140000091
wherein, the
Figure BDA0003268999140000095
i、j、R22All as described above.
Preferably, the B, C, E, F is independently selected from one of the following structures:
Figure BDA0003268999140000092
wherein, the
Figure BDA0003268999140000096
As described above.
Preferably, said B, C, E, F is independently selected from
Figure BDA0003268999140000093
Wherein, the
Figure BDA0003268999140000097
As described above.
Preferably, Ar is1Selected from hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuteriumIsopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, tert-butyl, deuterated tert-butyl, isobutyl, deuterated isobutyl, one of the following groups:
Figure BDA0003268999140000094
wherein, l is selected from one of 0,1, 2,3, 4 and 5, m is selected from one of 0,1, 2,3, 4,5, 6 and 7, n is selected from one of 0,1, 2,3, 4,5, 6,7,8 and 9, o is selected from one of 0,1, 2,3 and 4, and p is selected from one of 0,1, 2,3, 4,5, 6,7 and 8;
said R23One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group and a deuterated tert-butyl group, when a plurality of R's are present23Where they are the same or different,
said R11、R12Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, wherein the two can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11.
Preferably, R11、R12Can be connected to form one of saturated or unsaturated fatty rings of substituted or unsubstituted C3-C7 or one of saturated or unsaturated fatty rings of substituted or unsubstituted C5-C6.
Preferably, Ar is1One selected from a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, and the group shown below:
Figure BDA0003268999140000101
preferably, Ar is1One selected from methyl and the following groups:
Figure BDA0003268999140000102
preferably, Ar is1One selected from a hydrogen atom, a methyl group, and a group represented by:
Figure BDA0003268999140000103
preferably, Ar is1One selected from methyl and the following groups:
Figure BDA0003268999140000104
preferably, Ar is1One selected from methyl and the following groups:
Figure BDA0003268999140000105
preferably, Ar is1Selected from methyl or
Figure BDA0003268999140000106
Preferably, Ar is2、Ar3Independently selected from one of the following groups:
Figure BDA0003268999140000111
wherein, a is1One selected from 0,1, 2,3, 4 and 5, and b1Selected from 0,1,2.3, 4,5, 6,7, c1One selected from 0,1, 2,3 and 4, and d1One selected from 0,1, 2 and 3, and e1One selected from 0,1, 2,3, 4,5, 6,7, 8;
said R31Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, an n-propyl-substituted cyclohexyl group, an n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, a, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, when one of a plurality of R's is present31When they are the same, they may be different, and two adjacent R's are31Can be connected to form a saturated or unsaturated aliphatic ring of C3-C6;
said R32Selected from hydrogen atom, deuterium atom, fluorine atom, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuteratedN-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopropane, deuterated cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, deuterated cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, deuterated cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cyclopentenyl, deuterated cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, Adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, when one of more R's is present32When used, they may be the same or different;
said R33One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present33When they are the same or different, and two adjacent R' s33Can be connected to form a saturated or unsaturated aliphatic ring of substituted or unsubstituted C3-C6;
said R34Selected from hydrogen atoms, deuterium atomsOne of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, when a plurality of R exist34When they are the same, they may be different, and two adjacent R's are34Can be connected to form one of substituted or unsubstituted benzene ring, and substituted or unsubstituted saturated or unsaturated aliphatic ring of C3-C6;
said R301、R302Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, wherein the two can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11;
said L31、L32Independently selected from one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene and substituted or unsubstituted biphenylene;
ar is31、Ar32Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.
Preferably, R301、R302Can be connected to form one of saturated or unsaturated fatty rings of substituted or unsubstituted C3-C7 or one of saturated or unsaturated fatty rings of substituted or unsubstituted C5-C6.
Preferably, Ar is2、Ar3Independently selected from one of the following groups:
Figure BDA0003268999140000121
Figure BDA0003268999140000131
wherein, a is2One selected from 0,1, 2,3, 4 and 5, and b2One selected from 0,1, 2 and 3, and c2One selected from 0,1, 2,3, 4,5 and 6, d2One selected from 0,1, 2,3, 4,5, 6,7 and 8, and e2One selected from 0,1, 2,3 and 4, and f2One selected from 0 and 1, and g2One selected from 0,1, 2,3, 4,5, 6 and 7, and h2One selected from 0,1, 2,3, 4,5, 6,7,8 and 9, and the i2One selected from 0,1, 2,3, 4,5, 6,7,8, 9 and 10, and j is2One selected from 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13, 14;
said R41Selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, a n-propyl-substituted cyclohexyl group, a n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenylAlkenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, when there is one of more R's, when there is more than one R's present41When they are the same, they may be different, and two adjacent R's are41Can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C6;
said R42One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present42When used, they may be the same or different;
said R43One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present43When used, they may be the same or different;
said R44One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present44When they are the same, they may be different, and two adjacent R's are44Can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C6;
said R45One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present45When the two or more substituents are the same or different, they may be linked to form one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted saturated or unsaturated aliphatic ring having C3 to C6;
said R46One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group and a deuterated tert-butyl group, when a plurality of R's are present46They may be the same or different.
Preferably, Ar is2、Ar3Independently selected from one of the following groups:
Figure BDA0003268999140000141
Figure BDA0003268999140000151
Figure BDA0003268999140000161
Figure BDA0003268999140000171
preferably, said L1～L3Independently selected from single bond, one of the following groups:
Figure BDA0003268999140000172
wherein, a is3One selected from 0,1, 2,3 and 4, and b3One selected from 0,1, 2,3 and 4, and c3One selected from 0,1, 2;
said R51One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present51They may be the same or different.
Preferably, said L1～L3Independently selected from single bond, one of the following groups:
Figure BDA0003268999140000173
preferably, said L1～L3Independently selected from single bond, one of the following groups:
Figure BDA0003268999140000174
preferably, said L1～L3Independently selected from single bond, one of the following groups:
Figure BDA0003268999140000175
preferably, said L1～L3Independently selected from single bond, one of the following groups:
Figure BDA0003268999140000176
preferably, said L1～L3Independently selected from single bonds or
Figure BDA0003268999140000177
Preferably, said L1～L3Are all selected from single bonds.
Most preferably, the triarylamine compound containing a fluorene group is selected from one of the following compounds:
Figure BDA0003268999140000181
Figure BDA0003268999140000191
Figure BDA0003268999140000201
Figure BDA0003268999140000211
Figure BDA0003268999140000221
Figure BDA0003268999140000231
Figure BDA0003268999140000241
Figure BDA0003268999140000251
Figure BDA0003268999140000261
Figure BDA0003268999140000271
Figure BDA0003268999140000281
Figure BDA0003268999140000291
Figure BDA0003268999140000301
the above description only illustrates some specific structural forms of the triarylamine compound having a fluorene group represented by formula (I), but the present invention is not limited to these listed chemical structures, and all the substituents are defined as above and included on the basis of formula (I).
The triarylamine compound containing fluorene group shown in formula (I) can be prepared by the following synthetic route:
Figure BDA0003268999140000302
wherein the X, Y, Z is independently selected from chlorine atom, bromine atom or iodine atom, the A, B, C, E, F, Ar1、Ar2、Ar3、L1～L3All as described above.
Firstly, a trihalogenated compound (aa) and a cycloalkanone compound (bb) undergo a cyclization reaction to obtain an intermediate (cc); then, the intermediate (cc) is cyclized again with the compound (dd) to give an intermediate (M); and finally, carrying out Buchwald reaction on the intermediate (M) and a secondary amine compound (N) to obtain the triarylamine compound containing the fluorene group shown in the formula (I). The secondary amine compound (N) can be synthesized by a conventional method. The reaction conditions in the above synthetic route, such as reaction solvent, catalyst, ligand, base and the like, may be any of conventional methods, and are not particularly limited. The preparation method has the advantages of easily available raw materials, simple preparation process and excellent reaction yield.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer comprises a hole transmission area, a light-emitting layer and an electron transmission area, and the hole transmission area contains more than one of the triarylamine compounds containing fluorene groups.
Preferably, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light emission auxiliary layer.
Preferably, the hole transport region comprises a hole injection layer and a hole transport layer; more preferably, one of the hole injection layer and the hole transport layer contains one or more of the triarylamine compounds containing a fluorene group according to the present invention; more preferably, the hole injection layer and the hole transport layer each contain one or more of the triarylamine compounds containing a fluorene group according to the present invention.
Preferably, the hole transport region comprises a hole injection layer, a hole transport layer and a light-emitting auxiliary layer; more preferably, one of the hole injection layer, the hole transport layer and the light-emitting auxiliary layer contains one or more of the triarylamine compounds containing a fluorene group according to the present invention; more preferably, the luminescence auxiliary layer contains one or more of the triarylamine compounds containing a fluorene group according to the present invention.
The hole injection layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, allyl compounds, and other substances having high hole injection properties can be used, examples include, but are not limited to, 4',4 ″ -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyano-dimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), and triarylamine compounds containing a fluorene group as described herein. Preferably, the hole injection layer has a single-layer structure composed of a host material and a dopant material, the host material may be a triarylamine compound, preferably the triarylamine compound containing a fluorene group according to the present invention, and the dopant material may be an allyl compound. More preferably, the mass ratio of the host material to the doping material is 100: 1-100: 10.
The hole transport layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Aromatic amine compounds in which two or more triarylamine structures are linked by a single bond or a bridge structure may be used, and other aromatic compounds having a hole mobility of 10 may also be used-6cm2Examples of the substance having a structure of/Vs or more include, but are not limited to, 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' -tris (N, N-diphenylamino) triphenylamine (TDATA), and triarylamine compounds having a fluorene group as described in the present invention. Preferably, the hole transport layer uses the triarylamine compound containing a fluorene group according to the present invention.
The light-emitting auxiliary layer of the present invention may have a single-layer structure formed of a single substance, or may have a single-layer structure or a multi-layer structure formed of different substances. Aromatic amine compounds, spirofluorene derivatives, dibenzofuran derivatives in which two or more triarylamine structures are connected by a single bond or a bridge structure may be used, and other materials having suitable HOMO and T1 energy levels may be used, and examples thereof include TPD, NPB, N4, N4-bis ([1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1, 1': 4', 1' -terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine, N- ([1,1' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluorene-2-amine, N-bis ([1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, triarylamine compounds containing a fluorene group as described herein, but not limited thereto. Preferably, the luminescence auxiliary layer uses the triarylamine compound containing a fluorene group according to the present invention.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode, an organic layer arranged between the anode and the cathode, and a covering layer arranged on the side of the cathode, which is far away from the anode, wherein the covering layer contains more than one of the triarylamine compounds containing fluorene groups.
The covering layer comprises a first covering layer and/or a second covering layer, and when the first covering layer or the second covering layer is included, the covering layer can be a single-layer structure formed by a single substance or a single-layer structure formed by different substances; when the first cover layer and the second cover layer are included, they are a multilayer structure made of a single substance or different substances. The coating material may be an organic or inorganic material, and may be, for example, a metal halide, an oxide, a nitride, an oxynitride, a sulfide, a selenide, an aromatic compound, a heteroaromatic compound, an arylamine compound, or the like, and examples thereof include LiF, CsF, MgF2、CaF2、CsCl、CuI、V2O5、WO3、MoO3、TiO2、ZrO、ZnO、SiO2SiN, ZnS, the triarylamine compound having a fluorene group according to the present invention, but not limited thereto. It is preferable to use one or more of the triarylamine compounds having a fluorene group according to the present invention.
The light-emitting layer of the invention can only contain a guest material, can also adopt a form that the guest material is dispersed in a host material, and can form a double host by using two host materialsA bulk material. As the guest material, a fluorescent compound such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative and the like can be used, and examples thereof include 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro-1, 1,7, 7-tetramethyl-1H, 5H,11H- [ 1H]Benzopyran [6,7,8-ij]Quinolizin-11-one (C545T), 4' -bis (9-ethyl-3-carbazolenyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl]Examples of the phosphorescent material include biphenyl (DPAVBi), a metal complex such as an iridium complex, an osmium complex, and a platinum complex, and bis (4, 6-difluorophenylpyridine-N, C2) picolinatoiridium (FIrpic), tris (2-phenylpyridine) iridium (ir (ppy)3) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)2(acac)) and the like. The host material is preferably a material having a higher LUMO and a lower HOMO than the guest material, and examples thereof include a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, and an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and include 8-hydroxyquinoline aluminum (Alq)3) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), TPD, 4' -bis (9-Carbazole) Biphenyl (CBP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), and the like, but are not limited thereto.
The electron transport region comprises at least one of an electron injection layer, an electron transport layer and a hole blocking layer.
The electron injection layer can be a single-layer structure formed by a single substance, or a single-layer structure or a multi-layer structure formed by different substances, and one or more of the following substances can be selected: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances having a high electron-injecting property. Examples include Li, Ca, Sr, LiF, CsF, CaF2、BaO、Li2CO3、CaCO3、Li2C2O4、Cs2C2O4、CsAlF4LiOx, Yb, Tb, etc., but are not limited thereto.
The electron transport layer of the present invention may have a single-layer structure composed of a single substance, or a single-layer structure or a multilayer structure composed of different substances, and aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, and the like, which have high electron transport properties, may be used3Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq2) BAlq, 2- (4-biphenyl) -5-phenyl oxadiazole (PBD), and the like, but is not limited thereto.
The hole-blocking layer of the present invention may have a single-layer structure made of a single substance, or may have a single-layer structure or a multi-layer structure made of different substances. The selected material requires the T1 energy level to be higher than that of the light-emitting layer so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material is lower than that of the host material of the light-emitting layer, so that the hole blocking effect is achieved. Further, the electron mobility of the hole blocking layer material used is 10-6cm2and/Vs or above, the electron transmission is facilitated. Triazine derivatives, azabenzene derivatives and the like are preferable.
Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer;
preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer;
preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer and an electron injection layer;
preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The anode of the present invention may be a reflective anode, such as silver (Ag), magnesium (Mg), aluminum (Al),The reflective film formed of gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or an alloy thereof may also have a layer structure which has a high work function and is transparent or translucent, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), Aluminum Zinc Oxide (AZO), Indium Gallium Oxide (IGO), indium oxide (In)2O3) Or tin oxide (SnO)2) The layer structure formed depends on the type of device to be produced, for example, a bottom-emitting device (anode-side light emission) and a transparent or semitransparent anode, for example, a top-emitting device (cathode-side light emission) and a reflective anode.
The cathode can be a thin film with a low work function made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium silver alloy and the like, and can be made into a reflecting electrode, a transparent electrode or a semitransparent electrode by adjusting the thickness of the film, wherein the reflecting cathode is required to be made if a bottom emitting device is required to be prepared, and the transparent or semitransparent cathode is required to be made if a top emitting device is required to be prepared.
The organic layers, the cathode, the anode and the cover layer can be prepared by any one of vacuum evaporation, ink-jet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing and the like, and the film thickness of each layer is not particularly limited so as to obtain good device performance. The respective organic layers are preferably prepared by a method of vacuum evaporation, inkjet printing, or spin coating.
The thickness of each of the organic layer and the capping layer is usually 5nm to 100um, preferably 10nm to 200 nm. The thickness of the anode and the cathode is adjusted according to the required transparency.
The organic electroluminescent device provided by the invention can be applied to the field of OLED illumination and the field of OLED display, and can be specifically listed as a large-size display such as a smart phone display screen, a tablet computer display screen, an intelligent wearable device display screen, a television and the like, VR (virtual reality) and an automobile tail lamp and the like.
The technical scheme and technical effects of the present invention are further described below by examples and comparative examples.
The mass spectrum of the compound of the invention uses a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer of Watts corporation of England, and chloroform is used as a solvent;
the elemental analysis was carried out by using a Vario EL cube type organic element analyzer of Elementar, Germany, and the sample mass was 5 to 10 mg.
Synthesis example 1: preparation of Compound 27
Figure BDA0003268999140000341
Preparation of intermediate N-1:
toluene (600mL), ee-1(16.92g, 100.00mmol), ff-1(29.12g, 100.00mmol), palladium acetate (0.34g, 1.50mmol), sodium tert-butoxide (19.22g, 200.00mmol) and tri-tert-butylphosphine (16mL of a 1.0M solution in toluene) were added to the reaction flask and refluxed for 2 hours under nitrogen. After the reaction is completed, the temperature of the system is reduced to room temperature. The reaction was filtered through celite, the filtrate was concentrated, recrystallized from toluene/methanol 5/1, the reaction was filtered with suction, the filter cake was washed with methanol and collected to give N-1(32.26g, 85% yield), ms m/z: 379.2312 (theoretical value: 379.2300).
Preparation of intermediate cc-1:
aa-1(68.80g, 197.15mmol) and 180mL of tetrahydrofuran solvent were charged into a reaction flask, cooled to-78 ℃ under nitrogen protection, 29.25mL of a n-hexane mixed solution (3.38M) containing n-butyllithium was added, stirring was carried out for 50 minutes, 128.25mL of a tetrahydrofuran solution containing bb-1(15.14g, 180.00mmol) was added dropwise, stirring was continued at-78 ℃ for 50 minutes, and then, after warming to room temperature, stirring was continued for 3 hours. The organic layer was extracted and separated by adding a saturated ammonium chloride solution, the solvent was evaporated, the obtained residue was transferred to a reaction flask, 428mL of acetic anhydride and 18mL of hydrochloric acid were added, stirring was carried out at 100 ℃ for 3 hours, then the reaction solution was poured into 180mL of ice water to precipitate a solid, a solid crude product was obtained by filtration, and purification were carried out by passing through a silica gel column (n-hexane/ethyl acetate: 30/1) to obtain cc-1(42.69g, yield 82%), ms m/z: 288.0485 (theoretical value: 288.0473).
Preparation of intermediate M-1:
cc-1(38.01g, 131.43mmol) and 120mL of tetrahydrofuran solvent were charged into a reaction flask, cooled to-78 ℃ under nitrogen protection, 19.50mL of a n-hexane mixed solution (2.25M) containing n-butyllithium was added, stirring was carried out for 50 minutes, 85.50mL of a tetrahydrofuran solution containing dd-1(31.00g, 120.00mmol) was added dropwise, stirring was continued at-78 ℃ for 50 minutes, and then, after warming to room temperature, stirring was continued for 3 hours. Adding saturated ammonium chloride solution for extraction and separation of an organic layer, evaporating a solvent, transferring obtained residues into a reaction bottle, adding 12mL hydrochloric acid, stirring at 100 ℃ for 3 hours, pouring a reaction solution into 120mL ice water to separate out solids, filtering to obtain a solid crude product, and purifying and refining by a silica gel column (n-hexane/ethyl acetate) to obtain M-1(30.30g, yield 51%), mass spectrum M/z: 494.1817 (theoretical value: 494.1801).
Preparation of compound 27:
toluene (600mL), M-1(29.70g, 60.00mmol), N-1(25.05g, 66.00mmol), tris (dibenzylideneacetone) dipalladium (0.82g, 0.90mmol), sodium tert-butoxide (11.53g, 120.00mmol) and tri-tert-butylphosphine (8mL of a 1.0M solution in toluene) were added to a reaction flask and the reaction was refluxed for 2 hours under nitrogen. After the reaction, the temperature of the system is reduced to room temperature, the mixture is filtered by using kieselguhr, the filtrate is concentrated, the mixture is recrystallized by using toluene/methanol (20/1%), the recrystallized solid is obtained by suction filtration and elution by using methanol, and the compound 27(33.69g, the yield is 67%) is obtained, and the purity of the solid is not less than 99.82% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 837.4347 (theoretical value: 837.4335). Theoretical element content (%) C64H55N: c, 91.71; h, 6.61; n, 1.67. Measured elemental content (%): c, 91.72; h, 6.63; n, 1.68.
Synthesis example 2: preparation of Compound 45
Figure BDA0003268999140000351
Compound 45(36.42g, 72% yield) was obtained by the same procedure except that ee-1, ff-1 and N-1 in Synthesis example 1 were sequentially replaced with equimolar amounts of ee-2, ff-2 and N-2, and the solid purity ≧ 99.85% by HPLC. Mass spectrum m/z: 842.3675 (theoretical value: 842.3661). Theoretical element content (%)C64H46N2: c, 91.18; h, 5.50; and N, 3.32. Measured elemental content (%): c, 91.21; h, 5.49; and N, 3.31.
Synthetic example 3: preparation of Compound 67
Figure BDA0003268999140000352
Compound 67(33.23g, 65% yield) was obtained by the same procedure except that ee-1, ff-1, N-1 and bb-1 in Synthesis example 1 were replaced with equimolar amounts of ee-2, ff-3, N-3 and bb-3 in that order, and the purity by HPLC ≧ 99.73%. Mass spectrum m/z: 851.4014 (theoretical value: 851.4003). Theoretical element content (%) C64H37D8NO: c, 90.21; h, 6.27; n, 1.64. Measured elemental content (%): c, 90.25; h, 6.26; n, 1.65.
Synthetic example 4: preparation of Compound 117
Figure BDA0003268999140000353
Compound 117(32.28g, 61% yield) was obtained by the same procedure except that ee-1, ff-1, N-1 and bb-1 in Synthesis example 1 were replaced with equimolar amounts of ee-4, ff-4, N-4 and bb-4 in that order, and the purity by HPLC ≧ 99.64%. Mass spectrum m/z: 881.3282 (theoretical value: 881.3294). Theoretical element content (%) C66H43NO2: c, 89.87; h, 4.91; n, 1.59. Measured elemental content (%): c, 89.88; h, 4.95; n, 1.57.
Synthesis example 5: preparation of Compound 164
Figure BDA0003268999140000354
Synthesis examples 1 were repeated except for replacing ee-1, ff-1, N-1 and bb-1 with equimolar amounts of ee-4, ff-5, N-5 and bb-5 in that order to give 164(35.29g, 66% yield) as compound, and purity ≧ 99.58% by HPLC. Mass spectrum m/z: 890.4246 (theoretical value: 890.4236). Theoretical element content (%) C66H54N2O: c, 88.95; h, 6.11; and N, 3.14. Measured elemental content (%): c, 88.96; h, 6.15; and N, 3.13.
Synthetic example 6: preparation of Compound 169
Figure BDA0003268999140000361
Ff-1 and N-1 in synthesis example 1 were replaced with equimolar amounts of ff-6 and N-6 in this order, and the same procedures were repeated to give 169(35.39g, 73% yield) of compound having a solid purity of 99.85% or more by HPLC. Mass spectrum m/z: 807.3514 (theoretical value: 807.3501). Theoretical element content (%) C61H45NO: c, 90.67; h, 5.61; n, 1.73. Measured elemental content (%): c, 90.71; h, 5.60; n, 1.72.
Synthetic example 7: preparation of Compound 178
Figure BDA0003268999140000362
Compound 178(33.75g, 62% yield) was obtained by the same procedure except that ee-1, ff-1, N-1, aa-1 and bb-1 in Synthesis example 1 were sequentially replaced with equimolar amounts of ee-2, ff-7, N-7, aa-7 and bb-5, and the purity by HPLC ≧ 99.66%. Mass spectrum m/z: 906.3985 (theoretical value: 906.3974). Theoretical element content (%) C69H50N2: c, 91.36; h, 5.56; and N, 3.09. Measured elemental content (%): c, 91.37; h, 5.58; and N, 3.08.
Synthesis example 8: preparation of Compound 241
Figure BDA0003268999140000363
Ee-1, ff-1, N-1 and bb-1 in Synthesis example 1 were replaced with equimolar amounts of ee-8, ff-8, N-8 and bb-8 in that order, and the same procedure was repeated to obtain compound 241(34.66g, product obtained in the same manner as above)The rate is 66%), and the purity of the solid is not less than 99.74% by HPLC detection. Mass spectrum m/z: 874.4298 (theoretical value: 874.4287). Theoretical element content (%) C66H54N2: c, 90.58; h, 6.22; and N, 3.20. Measured elemental content (%): c, 90.59; h, 6.21; and N, 3.21.
Synthetic example 9: preparation of Compound 308
Figure BDA0003268999140000371
Ff-1, N-1 and bb-1 in Synthesis example 1 were replaced with equimolar amounts of ff-9, N-9 and bb-9 in the same manner, to give compound 308(36.05g, yield 71%), and purity ≧ 99.85% by HPLC. Mass spectrum m/z: 845.4033 (theoretical value: 845.4022). Theoretical element content (%) C65H51N: c, 92.27; h, 6.08; n, 1.66. Measured elemental content (%): c, 92.26; h, 6.09; n, 1.65.
Synthetic example 10: preparation of Compound 316
Figure BDA0003268999140000372
Ff-1 and N-1 in Synthesis example 1 were replaced with equimolar amounts of ff-4 and N-10 in this order, and the same procedures were repeated to give compound 316(34.06g, yield 66%) having a solid purity of not less than 99.72% by HPLC. Mass spectrum m/z: 859.3827 (theoretical value: 859.3814). Theoretical element content (%) C65H49NO: c, 90.77; h, 5.74; n, 1.63. Measured elemental content (%): c, 90.81; h, 5.73; n, 1.64.
Synthetic example 11: preparation of Compound 362
Figure BDA0003268999140000373
Ff-1, bb-1, and N-1 in Synthesis example 1 were sequentially replaced with equimolar amounts of ff-11, bb-11, and N-11, and the same procedure was followed to obtain compound 362(34.72g, yield)65%) and the purity of the solid is not less than 99.64% by HPLC. Mass spectrum m/z: 889.3756 (theoretical value: 889.3742). Theoretical element content (%) C66H51And NS: c, 89.05; h, 5.77; n, 1.57. Measured elemental content (%): c, 89.09; h, 5.78; n, 1.55.
Synthetic example 12: preparation of Compound 380
Figure BDA0003268999140000374
Compound 380(33.75g, 68% yield) was obtained by the same procedure except that ff-1, bb-1 and N-1 in Synthesis example 1 were replaced with equal molar amounts of ff-12, bb-12 and N-12 in that order, and had a solid purity of 99.84% or higher by HPLC. Mass spectrum m/z: 826.3954 (theoretical value: 826.3941). Theoretical element content (%) C62H38D7NO: c, 90.04; h, 6.34; n, 1.69. Measured elemental content (%): c, 90.08; h, 6.32; n, 1.68.
Synthetic example 13: preparation of Compound 404
Figure BDA0003268999140000381
Compound 404(34.75g, 63% yield) was obtained by the same procedure except that ee-1, ff-1, N-1 and bb-1 in Synthesis example 1 were replaced with equimolar amounts of ee-13, ff-13, N-13 and bb-13 in that order, and the purity by HPLC ≧ 99.55%. Mass spectrum m/z: 918.3987 (theoretical value: 918.3974). Theoretical element content (%) C70H50N2: c, 91.47; h, 5.48; and N, 3.05. Measured elemental content (%): c, 91.48; h, 5.47; and N, 3.07.
Synthesis example 14: preparation of Compound 473
Figure BDA0003268999140000382
Bb-1 and N-1 in Synthesis example 1 were replaced with equimolar amounts of bb-14 and N-10 in the same manner as above, and the other steps were repeated to obtainBy the reaction of the compound 473(34.58g, 67% yield), the solid purity is > 99.79% by HPLC. Mass spectrum m/z: 859.3822 (theoretical value: 859.3814). Theoretical element content (%) C65H49NO: c, 90.77; h, 5.74; n, 1.63. Measured elemental content (%): c, 90.81; h, 5.75; n, 1.61.
Synthetic example 15: preparation of Compound 528
Figure BDA0003268999140000383
Compound 528(32.18g, 64% yield) was obtained by the same procedure except that ee-1, ff-1 and N-1 in Synthesis example 1 were sequentially replaced with equal molar amounts of ee-15, ff-4 and N-15, and the solid purity ≧ 99.84% by HPLC. Mass spectrum m/z: 837.3986 (theoretical value: 837.3971). Theoretical element content (%) C63H51NO: c, 90.29; h, 6.13; n, 1.67. Measured elemental content (%): c, 90.28; h, 6.12; n, 1.71.
Synthetic example 16: preparation of Compound 546
Figure BDA0003268999140000384
Ff-1 and N-1 in synthesis example 1 were replaced with equimolar amounts of ff-16 and N-16 in this order, and the same procedures were repeated to give compound 546(33.98g, yield 66%) with a solid purity of 99.78% by HPLC. Mass spectrum m/z: 857.4033 (theoretical value: 857.4022). Theoretical element content (%) C66H51N: c, 92.38; h, 5.99; n, 1.63. Measured elemental content (%): c, 92.39; h, 5.97; n, 1.64.
Synthetic example 17: preparation of Compound 550
Figure BDA0003268999140000391
The same procedures were repeated except for replacing ee-1, ff-1 and N-1 in Synthesis example 1 with equimolar amounts of ee-13, ff-17 and N-17 to obtain a compound550(35.11g, yield 65%), and purity ≧ 99.70% by HPLC. Mass spectrum m/z: 899.4480 (theoretical value: 899.4491). Theoretical element content (%) C69H57N: c, 92.06; h, 6.38; n, 1.56. Measured elemental content (%): c, 92.08; h, 6.37; n, 1.57.
Synthetic example 18: preparation of Compound 575
Figure BDA0003268999140000392
Compound 575(33.82g, 62% yield) was obtained by the same procedure except that ee-1, ff-1 and N-1 in Synthesis example 1 were sequentially replaced with equimolar amounts of ee-2, ff-18 and N-18, and the purity by HPLC ≧ 99.68%. Mass spectrum m/z: 908.4143 (theoretical value: 908.4130). Theoretical element content (%) C69H52N2: c, 91.15; h, 5.57; and N, 3.08. Measured elemental content (%): c, 91.17; h, 5.59; and N, 3.09.
Synthetic example 19: preparation of Compound 593
Figure BDA0003268999140000393
Preparation of intermediate N-24:
toluene (900mL), ee-19(13.97g, 150.00mmol), ff-6(37.06g, 150.00mmol), palladium acetate (0.51, 2.25mmol), potassium tert-butoxide (33.66g, 300.00mmol) and tri-tert-butylphosphine (24mL of a 1.0M solution in toluene) were added to the reaction flask and refluxed for 2 hours under nitrogen. After the reaction was completed, the temperature of the system was decreased to room temperature, the reaction solution was filtered with celite, the filtrate was concentrated, and recrystallized with toluene/methanol 10/3, the reaction solution was suction filtered, the filter cake was washed with methanol, and the filter cake was collected to obtain N-24(35.01g, yield 90%), ms m/z: 259.0987 (theoretical value: 259.0997).
Preparation of intermediate hh-19:
toluene (750mL), N-24(32.41g, 125.00mmol), gg-19(23.93g, 125.00mmol), palladium acetate (0.42g, 1.88mmol), potassium tert-butoxide (28.05g, 250.00mmol) and tri-tert-butylphosphine (20mL of a 1.0M solution in toluene) were added to the reaction flask and refluxed for 3 hours under nitrogen. After the reaction was completed, the temperature of the system was decreased to room temperature, the reaction solution was filtered with celite, the filtrate was concentrated, and it was recrystallized with toluene/methanol 4/1, the reaction solution was suction-filtered, the filter cake was washed with methanol, and the filter cake was collected to obtain hh-19(40.68g, yield 88%), ms m/z: 369.0934 (theoretical value: 369.0920).
Preparation of compound 593:
compound 593(36.39g, 65% yield) was obtained by the same procedure except that ee-1, ff-1, bb-1 and N-1 in Synthesis example 1 were replaced with equimolar amounts of ee-13, hh-19, bb-19 and N-19, respectively, and the purity by HPLC ≧ 99.82%. Mass spectrum m/z: 932.3779 (theoretical value: 932.3767). Theoretical element content (%) C70H48N2O: c, 90.10; h, 5.18; and N, 3.00. Measured elemental content (%): c, 90.07; h, 5.22; and N, 3.03.
Synthesis example 20: preparation of Compound 599
Figure BDA0003268999140000401
Compound 599(34.23g, 61% yield) was obtained by the same procedure except that ee-1, ff-1 and N-1 in Synthesis example 1 were sequentially replaced with equal molar amounts of ee-2, ff-20 and N-20, and the solid purity ≧ 99.65% by HPLC. Mass spectrum m/z: 934.4298 (theoretical value: 934.4287). Theoretical element content (%) C71H54N2: c, 91.18; h, 5.82; and N, 3.00. Measured elemental content (%): c, 91.21; h, 5.81; and N, 3.02.
Synthetic example 21: preparation of Compound 622
Figure BDA0003268999140000402
Compound 622(36.36g, 66% yield) was obtained in the same manner as in the previous step except that ee-1, ff-1 and N-1 in Synthesis example 1 were replaced with equimolar amounts of ee-21, ff-21 and N-21 in this order,the purity of the solid is not less than 99.67 percent by HPLC detection. Mass spectrum m/z: 917.4739 (theoretical value: 917.4726). Theoretical element content (%) C69H47D7N2: c, 90.25; h, 6.69; and N, 3.05. Measured elemental content (%): c, 90.26; h, 6.72; and N, 3.04.
Synthetic example 22: preparation of Compound 637
Figure BDA0003268999140000403
By the same procedures except for replacing ee-1, ff-1, N-1 and dd-1 in synthetic example 1 with equal molar amounts of ee-19, ff-22, N-22 and dd-22 in this order, compound 637(39.58g, yield 72%) with a solid purity ≧ 99.68% by HPLC was obtained. Mass spectrum m/z: 915.4819 (theoretical value: 915.4804). Theoretical element content (%) C70H61N: c, 91.76; h, 6.71; n, 1.53. Measured elemental content (%): c, 91.77; h, 6.69; n, 1.56.
Synthetic example 23: preparation of Compound 648
Figure BDA0003268999140000411
Compound 648(34.02g, 66% yield) was obtained in the same manner as in Synthesis example 1 except that ee-1, ff-1, N-1, cc-1 and dd-1 were replaced with equimolar amounts of ee-23, ff-23, N-23, cc-19 and dd-22 in that order, and the purity by HPLC ≧ 99.72% was obtained. Mass spectrum m/z: 858.4011 (theoretical value: 858.4022). Theoretical element content (%) C66H42D5N: c, 92.27; h, 6.10; n, 1.63. Measured elemental content (%): c, 92.24; h, 6.12; n, 1.62.
Synthetic example 24: preparation of Compound 650
Figure BDA0003268999140000412
The cc-1, dd-1 and N-1 in Synthesis example 1 were substituted by equimolar amounts in this ordercc-5, dd-24 and N-9, and the other steps are the same, so that the compound 650(34.95g, yield 69%) is obtained, and the purity of the solid is ≧ 99.75% by HPLC. Mass spectrum m/z: 843.3881 (theoretical value: 843.3865). Theoretical element content (%) C65H49N: c, 92.49; h, 5.85; n, 1.66. Measured elemental content (%): c, 92.50; h, 5.87; n, 1.65.
Synthetic example 25: preparation of compound 659
Figure BDA0003268999140000413
Compound 659(36.23g, 67% yield) was obtained by the same procedure except that ee-1, ff-1, N-1, cc-1 and dd-1 in Synthesis example 1 were replaced with equimolar amounts of ee-23, ff-25, N-25, cc-5 and dd-22, respectively, and the purity by HPLC ≧ 99.64%. Mass spectrum m/z: 900.4506 (theoretical value: 900.4492). Theoretical element content (%) C69H48D5N: c, 91.96; h, 6.49; n, 1.55. Measured elemental content (%): c, 91.95; h, 6.52; n, 1.56.
Synthetic example 26: preparation of Compound 665
Figure BDA0003268999140000414
Compound 665(34.27g, 70% yield) was obtained by the same procedure except for replacing ee-1, ff-1, N-1, cc-1 and dd-1 in Synthesis example 1 with equimolar amounts of ee-2, ff-26, N-26, cc-8 and dd-26 in that order, and had a solid purity ≧ 99.78% by HPLC. Mass spectrum m/z: 815.3541 (theoretical value: 815.3552). Theoretical element content (%) C63H45N: c, 92.73; h, 5.56; n, 1.72. Measured elemental content (%): c, 92.70; h, 5.58; and N, 1.70.
Synthetic example 27: preparation of Compound 680
Figure BDA0003268999140000421
In the same manner as in Synthesis example 1, cc-1, dd-1 and N-1 were replaced with equimolar amounts of cc-9, dd-27 and N-9 in that order to obtain compound 680(36.56g, yield 68%), and purity ≧ 99.72% by HPLC. Mass spectrum m/z: 895.4162 (theoretical value: 895.4178). Theoretical element content (%) C69H53N: c, 92.48; h, 5.96; n, 1.56. Measured elemental content (%): c, 92.45; h, 5.97; n, 1.58.
Synthetic example 28: preparation of Compound 686
Figure BDA0003268999140000422
Compound 686(35.89g, 65% yield) was obtained in the same manner as in Synthesis example 1 except that ee-1, ff-1, N-1, cc-1 and dd-1 were replaced with equimolar amounts of ee-2, ff-28, N-28, cc-9 and dd-22 in this order, and the purity by HPLC ≧ 99.64%. Mass spectrum m/z: 919.4191 (theoretical value: 919.4178). Theoretical element content (%) C71H53N: c, 92.67; h, 5.81; n, 1.52. Measured elemental content (%): c, 92.69; h, 5.79; n, 1.54.
Synthetic example 29: preparation of Compound 732
Figure BDA0003268999140000423
By replacing aa-1, bb-1 and N-1 in Synthesis example 1 with equal molar amounts of aa-29, bb-29 and N-11 in that order, compound 732(33.70g, 69% yield) was obtained with equal molar amounts of aa-29, bb-29 and N-11, and the solid purity ≧ 99.65% by HPLC. Mass spectrum m/z: 813.3379 (theoretical value: 813.3367). Theoretical element content (%) C60H39D4And NS: c, 88.52; h, 5.82; n, 1.72. Measured elemental content (%): c, 88.53; h, 5.80; n, 1.75.
Synthetic example 30: preparation of compound 763
Figure BDA0003268999140000424
Preparation of intermediate N-30:
intermediate N-30(30.36g, 84% yield) was obtained by substituting ee-1 and ff-1 in Synthesis example 1 for the equimolar amounts of ee-19 and ff-30 in that order, and following the procedure for the preparation of intermediate N-1 in Synthesis example 1, Mass Spectrometry m/z: 361.1845 (theoretical value: 361.1830).
Preparation of intermediate A-1:
intermediate M-1(110.00mmol, 54.46g), hh-1(121.00mmol, 30.73g), Pd (dppf) Cl2(3.30mmol，2.41g)，K2CO3(330.00mmol, 45.61g), DMF (500mL) was added to the flask and refluxed for 3 hours under nitrogen. After the reaction is finished, cooling the system to room temperature, adding 750mL of water to generate a precipitate, filtering, washing and drying the precipitate to obtain a precipitate, dissolving the precipitate in 500mL of ethyl acetate, filtering to remove insoluble substances, collecting filtrate, removing the solvent by rotary evaporation, and drying to obtain an intermediate A-1(56.62g, yield 80%); mass spectrum m/z: 586.3057 (theoretical value: 586.3043).
Preparation of intermediate M-30:
intermediate A-1(91.80mmol, 53.85g), gg-1(90.00mmol, 17.23g), Pd (dppf) Cl2(1.80mmol, 1.32g), KOAc (180.00mmol, 17.67g), and 300mL of toluene, 100mL of ethanol, and 100mL of water were added to the reaction flask, and the mixture was stirred and refluxed for 3.5 hours under nitrogen. After the reaction is finished, the temperature of the system is reduced to room temperature, a filter cake is obtained by suction filtration, the filter cake is washed by ethanol, and finally the filter cake is filtered by toluene/ethanol (10: 1 recrystallization to give intermediate M-30(38.55g, 75% yield); mass spectrum m/z: 570.2129 (theoretical value: 570.2114).
Preparation of compound 763:
by substituting N-1 in synthesis example 1 with N-30 in equimolar amounts, 763(35.49g, 66% yield) was obtained, and the purity of solid was ≧ 99.72% by HPLC. Mass spectrum m/z: 895.4188 (theoretical value: 895.4178). Theoretical element content (%) C69H53N: c, 92.48; h, 5.96; n, 1.56. Measured elemental content (%): c, 92.47; h, 5.97; n, 1.59.
Synthetic example 31: preparation of compound 769
Figure BDA0003268999140000431
Compound 769(33.93g, 67% yield) was obtained by the same procedure except that ee-19, ff-30 and N-30 in Synthesis example 30 were sequentially replaced with equal molar amounts of ee-2, ff-31 and N-31, and the purity by HPLC ≧ 99.75%. Mass spectrum m/z: 843.3876 (theoretical value: 843.3865). Theoretical element content (%) C65H49N: c, 92.49; h, 5.85; n, 1.66. Measured elemental content (%): c, 92.48; h, 5.86; n, 1.68.
Synthetic example 32: preparation of Compound 771
Figure BDA0003268999140000432
N-30 and gg-1 in Synthesis example 30 were sequentially replaced with equimolar amounts of N-26 and gg-2, and the same procedures were repeated to give compound 771(33.26g, yield 64%) having a solid purity of 99.72% by HPLC. Mass spectrum m/z: 865.3718 (theoretical value: 865.3709). Theoretical element content (%) C67H47N: c, 92.91; h, 5.47; n, 1.62. Measured elemental content (%): c, 92.92; h, 5.46; n, 1.65.
Synthetic example 33: preparation of Compound 773
Figure BDA0003268999140000441
Preparation of intermediate M-33:
by substituting ee-1, ff-1, N-1 and bb-1 in Synthesis example 1 for equimolar amounts of ee-19, ff-3, N-33 and bb-33 in that order, according to the method for preparing intermediate M-1 in Synthesis example 1, intermediate M-33(29.82g) was obtained, and mass M/z: 506.1819 (theoretical value: 506.1801).
Preparation of compound 773:
substitution of N-30 in Synthesis example 30 successively to equimolarThe same procedure was repeated except for using N-33 in an amount of mol to give 773(34.40g, yield 65%) having a purity of 99.68% by HPLC. Mass spectrum m/z: 881.3667 (theoretical value: 881.3658). Theoretical element content (%) C67H47NO: c, 91.23; h, 5.37; n, 1.59. Measured elemental content (%): c, 91.27; h, 5.36; n, 1.58.
Synthesis example 34: preparation of Compound 775
Figure BDA0003268999140000442
Compound 775(37.14g, 68% yield) obtained by substituting ee-19, ff-30 and N-30 in Synthesis example 30 with equal molar amounts of ee-13, ff-4 and N-34 in that order and using the same procedure as above, had a solid purity ≧ 99.64% by HPLC. Mass spectrum m/z: 909.3983 (theoretical value: 909.3971). Theoretical element content (%) C69H51NO: c, 91.06; h, 5.65; n, 1.54. Measured elemental content (%): c, 91.07; h, 5.69; n, 1.52.
Synthetic example 35: preparation of Compound 784
Figure BDA0003268999140000443
In the same manner as in Synthesis example 1, cc-1, dd-1 and N-1 were replaced with equimolar amounts of cc-5, dd-35 and N-6 in that order to obtain 784(37.58g, 73% yield) having a solid purity of 99.76% or more by HPLC. Mass spectrum m/z: 857.3672 (theoretical value: 857.3658). Theoretical element content (%) C65H47NO: c, 90.98; h, 5.52; n, 1.63. Measured elemental content (%): c, 90.94; h, 5.53; n, 1.61.
The organic materials in the preparation examples are purified by sublimation, and the purity is over 99.99 percent. The ITO glass substrate and the ITO/Ag/ITO glass substrate used in the preparation examples were commercially available.
The following are other compounds used in the preparation examples in addition to the triarylamine compound containing a fluorene group of the present invention:
Figure BDA0003268999140000451
a combined IVL test system is formed by test software, a computer, a K2400 digital source meter of Keithley company in the United states and a PR788 spectral scanning luminance meter of Photo Research company in the United states, and the device prepared by the invention is tested at the current density of 15mA/cm at the atmospheric pressure and the room temperature2Luminous efficiency and driving voltage at the time of the formation of the electrodes. The lifetime (luminance decay to 95% of the initial luminance) of the devices prepared according to the invention was tested at atmospheric pressure and room temperature using the McScience M6000 OLED lifetime test system. The test results are shown in tables 1 to 4.
Comparative device preparation example 1: comparison device 1
Firstly, the ITO glass substrate is ultrasonically cleaned for 20 minutes by deionized water for 2 times, then is ultrasonically cleaned for 20 minutes by isopropanol, acetone and methanol in sequence, is exposed in ultraviolet rays and ozone for 30 minutes, and is finally placed in vacuum evaporation equipment for standby.
Evaporating each organic material layer and the cathode layer by layer on the ITO glass substrate, and specifically comprises the following steps: a. 2-TNATA is taken as a hole injection layer and has the thickness of 55 nm; b. HT-1 is used as a hole transport layer and has the thickness of 35 nm; c. TBADN and BD (97: 3 by mass) as a light-emitting layer, and the thickness of the layer was 25 nm; d. TPBi is taken as a hole blocking layer and has the thickness of 25 nm; e. liq is used as an electron transport layer and has the thickness of 30 nm; f. LiF is used as an electron injection layer and has the thickness of 0.2 nm; g. al is used as a cathode and the thickness is 110 nm.
Comparative device preparation examples 2 to 3: comparison device 2-3
HT-1 is replaced by HT-2 and HT-3 respectively, and other steps are the same as those of the comparative device preparation example 1, so that comparative devices 2-3 can be obtained.
Device preparation examples 1 to 35: light emitting device 1 to 35
HT-1 was replaced with the triarylamine compound containing a fluorene group described in synthesis examples 1 to 35, respectively, and the remaining steps were the same as in comparative device preparation example 1, to obtain light emitting devices 1 to 35.
TABLE 1
Figure BDA0003268999140000461
Figure BDA0003268999140000471
Comparative device preparation example 4: comparison device 4
Firstly, the ITO glass substrate is ultrasonically cleaned for 20 minutes by deionized water for 2 times, then is ultrasonically cleaned for 20 minutes by isopropanol, acetone and methanol in sequence, is exposed in ultraviolet rays and ozone for 30 minutes, and is finally placed in vacuum evaporation equipment for standby.
Evaporating each organic material layer and the cathode layer by layer on the ITO glass substrate, and specifically comprises the following steps: a. HT-1 and F4-TCNQ (mass ratio of 100:2) as hole injection layers with a thickness of 50 nm; b. NPB is used as a hole transport layer and has the thickness of 40 nm; c. TBADN and BD (96: 4 by mass) as a light-emitting layer, and the thickness of the layer was 30 nm; d. BAlq is used as a hole blocking layer and has the thickness of 25 nm; e. the Bphen is used as an electron transport layer and has the thickness of 30 nm; f. LiF is used as an electron injection layer and has the thickness of 0.2 nm; g. al as a cathode and having a thickness of 100 nm.
Comparative device preparation examples 5 to 6: comparison devices 5-6
HT-1 is replaced by HT-2 and HT-3 respectively, and other steps are the same as those of the comparative device preparation example 4, so that comparative devices 5-6 can be obtained.
Device preparation examples 36 to 70: light emitting devices 36-70
HT-1 was replaced with the triarylamine compound containing a fluorene group described in synthesis examples 1 to 35, respectively, and the remaining steps were the same as in comparative device preparation example 3, to obtain light-emitting devices 36 to 70.
TABLE 2
Figure BDA0003268999140000472
Figure BDA0003268999140000481
Comparative device preparation example 7: comparison device 7
Firstly, the ITO glass substrate is ultrasonically cleaned for 20 minutes by deionized water for 2 times, then is ultrasonically cleaned for 20 minutes by isopropanol, acetone and methanol in sequence, is exposed in ultraviolet rays and ozone for 30 minutes, and is finally placed in vacuum evaporation equipment for standby.
Evaporating each organic material layer and the cathode layer by layer on the ITO glass substrate, and specifically comprises the following steps: a. 2-TNATA is used as a hole injection layer and has the thickness of 45 nm; b. alpha-NPD is used as a hole transport layer and has the thickness of 40 nm; c. HT-1 is used as a luminescence auxiliary layer and has the thickness of 30 nm; d. MCBP and Ir (ppy)3(the mass ratio is 92: 8) as a light-emitting layer, and the thickness is 30 nm; e. TPBi is used as a hole blocking layer and has the thickness of 15 nm; f. liq is used as an electron transport layer and has the thickness of 35 nm; g. LiF is used as an electron injection layer and has the thickness of 0.2 nm; h. al as a cathode and having a thickness of 140 nm.
Comparative device preparation examples 8 to 9: comparison device 8-9
HT-1 is replaced by HT-2 and HT-3 respectively, and other steps are the same as those of the comparative device preparation example 7, so that comparative devices 8-9 can be obtained.
Device preparation examples 71 to 105: light emitting devices 71 to 105
HT-3 was replaced with the triarylamine compound containing a fluorene group described in synthesis examples 1 to 35, respectively, and the remaining steps were the same as in comparative device preparation example 5, to obtain light-emitting devices 71 to 105.
TABLE 3
Figure BDA0003268999140000491
Figure BDA0003268999140000501
Comparative device preparation example 10: comparison device 10
Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned for 20 minutes by deionized water for 2 times, then sequentially ultrasonically cleaned for 20 minutes by isopropanol, acetone and methanol, then exposed in ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
Evaporating each organic material layer and the cathode layer by layer on the ITO glass substrate, and specifically comprises the following steps: a. 2-TNATA is taken as a hole injection layer and has the thickness of 50 nm; b. alpha-NPD is used as a hole transport layer and has the thickness of 45 nm; c. CDBP and Ir (2-phq)3(95: 5 by mass) as a light-emitting layer, and the thickness is 35 nm; d. BAlq is used as a hole blocking layer and has the thickness of 20 nm; e. alq3As an electron transport layer, the thickness is 35 nm; f. LiF is used as an electron injection layer and has the thickness of 0.2 nm; g. mg and Ag (mass ratio of 1: 9) are used as cathodes, and the thickness is 12 nm; h: CP-1 was used as a capping layer with a thickness of 75 nm.
Comparative device preparation example 11: comparison device 11
Comparative device 11 was obtained by replacing CP-1 with CP-2 and the other steps were the same as in comparative device preparation example 10.
Device preparation examples 103 to 136: light emitting devices 103-136
CP-1 was replaced with the triarylamine compound containing fluorene groups of the present invention in synthesis examples 1 to 34, respectively, and the remaining steps were the same as in comparative device preparation example 7, to obtain light-emitting devices 103 to 136.
TABLE 4
Figure BDA0003268999140000502
Figure BDA0003268999140000511
Figure BDA0003268999140000521
The device data in tables 1-3 show that the triarylamine compound containing fluorene group in the formula (I) has high hole mobility, good thermal stability, film forming property and proper energy level, can improve the driving voltage, the luminous efficiency and the service life of the device when applied to a hole transport layer, a light-emitting auxiliary layer or a hole injection layer, and is a hole transport material with excellent performance.
The device data in table 4 show that the triarylamine compound containing fluorene group in formula (I) is applied to an OLED device as a covering layer, which improves the light emitting efficiency and the service life of the device, and indicates that it is also a kind of covering layer material with excellent performance.
In conclusion, the triarylamine compound containing fluorene group provided by the invention is an OLED material with excellent performance and wide application, and has good application prospect.
It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.

Claims (10)

1. A triarylamine compound containing fluorene groups is characterized in that the triarylamine compound containing fluorene groups has a structure shown in a formula (I):
Figure FDA0003268999130000011
wherein A is selected from saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11;
b, C, E, F is independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl and substituted or unsubstituted phenanthryl;
ar is1Selected from hydrogen atom, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstitutedOne of unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted sec-butyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthryl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, and substituted or unsubstituted carbazolyl group;
ar is2、Ar3Independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, -NR1R2In the formula (I), the R is1、R2Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl and substituted or unsubstituted carbazolyl, when the number of the substituent groups in the substituted or unsubstituted phenyl is more than two, adjacent substituent groups can be connected to form one of substituted or unsubstituted saturated or unsaturated aliphatic ring of C3-C10 and substituted or unsubstituted benzene ring;
said L1～L3Independently selected from one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene and substituted or unsubstituted biphenylene.
2. A triarylamine compound containing fluorene groups according to claim 1 wherein a is selected from one of the following structures:
Figure FDA0003268999130000012
Figure FDA0003268999130000021
wherein ". mark" represents a position where ring A shares a carbon atom with a five-membered carbocyclic ring;
a is selected from one of 0,1, 2,3 and 4, b is selected from one of 0,1 and 2, c is selected from one of 0,1, 2,3, 4,5 and 6, d is selected from one of 0,1, 2,3, 4,5, 6,7 and 8, e is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9 and 10, f is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13 and 14, g is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11 and 12, h is selected from one of 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13, 14, 15 and 16;
said R21Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, an n-propyl-substituted cyclohexyl group, an n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, a, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, and pharmaceutically acceptable salts thereof,Deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, when one of a plurality of R's is present21They may be the same or different.
3. A triarylamine compound containing fluorene groups according to claim 1 wherein a is selected from one of the following structures:
Figure FDA0003268999130000022
4. a triarylamine compound containing fluorene groups according to claim 1 wherein B, C, E, F is independently selected from one of the following structures:
Figure FDA0003268999130000031
wherein, the
Figure FDA0003268999130000032
Represents a position attached to a carbon atom on the five-membered carbon ring;
i is selected from one of 0,1, 2,3 and 4, j is selected from one of 0,1, 2,3, 4,5 and 6, and k is selected from one of 0,1, 2,3, 4,5, 6,7 and 8;
said R22Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, an n-propyl-substituted cyclohexyl group, an n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, a, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl-substituted piperazinyl, when one of a plurality of R's is present, when more than one R's are present22They may be the same or different.
5. The triarylamine compound containing a fluorene group according to claim 1, wherein Ar is Ar1Selected from the group consisting of hydrogen atom, deuterium atom, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, tert-butyl group, deuterated tert-butyl group, isobutyl group, deuterated isobutyl group, and the group represented by the formulaOne of the clusters:
Figure FDA0003268999130000033
wherein, l is selected from one of 0,1, 2,3, 4 and 5, m is selected from one of 0,1, 2,3, 4,5, 6 and 7, n is selected from one of 0,1, 2,3, 4,5, 6,7,8 and 9, o is selected from one of 0,1, 2,3 and 4, and p is selected from one of 0,1, 2,3, 4,5, 6,7 and 8;
said R23One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group and a deuterated tert-butyl group, when a plurality of R's are present23Where they are the same or different,
said R11、R12Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, wherein the two can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11.
6. The triarylamine compound containing a fluorene group according to claim 1, wherein Ar is Ar2、Ar3Independently selected from one of the following groups:
Figure FDA0003268999130000041
wherein, a is1One selected from 0,1, 2,3, 4 and 5, and b1One selected from 0,1, 2,3, 4,5, 6 and 7A, said c1One selected from 0,1, 2,3 and 4, and d1One selected from 0,1, 2 and 3, and e1One selected from 0,1, 2,3, 4,5, 6,7, 8;
said R31Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, an n-propyl-substituted cyclohexyl group, an n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cyclopentenyl group, a deuterated cyclopentenyl group, a, Methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, when one of a plurality of R's is present31When they are the same, they may be different, and two adjacent R's are31Can be connected to form a saturated or unsaturated aliphatic ring of C3-C6;
said R32Selected from hydrogen atom, deuterium atom, fluorine atom, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl groupPropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopropane, deuterated cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, deuterated cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, deuterated cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cyclopentenyl, deuterated cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, deuterated adamantyl, Methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, deuterated tetrahydropyrrolyl, piperidinyl, deuterated piperidinyl, morpholinyl, deuterated morpholinyl, thiomorpholinyl, deuterated thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, deuterated phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, deuterated naphthyl-substituted piperazinyl, when a plurality of R's are present32When used, they may be the same or different;
said R33One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present33When they are the same or different, and two adjacent R' s33Can be connected to form a saturated or unsaturated aliphatic ring of substituted or unsubstituted C3-C6;
said R34Selected from hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl and deuteriumOne of ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, when a plurality of R exist34When they are the same, they may be different, and two adjacent R's are34Can be connected to form one of substituted or unsubstituted benzene ring, and substituted or unsubstituted saturated or unsaturated aliphatic ring of C3-C6;
said R301、R302Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, wherein the two can be connected to form one of saturated or unsaturated aliphatic rings of substituted or unsubstituted C3-C11;
said L31、L32Independently selected from one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene and substituted or unsubstituted biphenylene;
ar is31、Ar32Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.
7. The triarylamine compound containing a fluorene group according to claim 1, wherein L is1～L3Independently selected from single bond, one of the following groups:
Figure FDA0003268999130000051
wherein, a is3One selected from 0,1, 2,3 and 4, and b3One selected from 0,1, 2,3 and 4, and c3One selected from 0,1, 2;
said R51One selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group and a deuterated naphthyl group, when a plurality of R's are present51They may be the same or different.
8. The triarylamine compound containing fluorene groups according to claim 1, wherein the triarylamine compound containing fluorene groups is selected from one of the following compounds:
Figure FDA0003268999130000061
Figure FDA0003268999130000071
Figure FDA0003268999130000081
Figure FDA0003268999130000091
Figure FDA0003268999130000101
Figure FDA0003268999130000111
Figure FDA0003268999130000121
Figure FDA0003268999130000131
Figure FDA0003268999130000141
Figure FDA0003268999130000151
Figure FDA0003268999130000161
Figure FDA0003268999130000171
Figure FDA0003268999130000181
9. an organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, and wherein the hole transport region contains at least one of the triarylamine compounds containing a fluorene group as defined in any one of claims 1 to 8.
10. An organic electroluminescent device comprising an anode, a cathode, an organic layer disposed between the anode and the cathode, and a cover layer disposed on the side of the cathode away from the anode, wherein the cover layer contains at least one triarylamine compound having a fluorene group as defined in any one of claims 1 to 8.
CN202111095326.3A 2021-09-17 2021-09-17 Triarylamine compound containing fluorene group and organic electroluminescent device thereof Active CN113788759B (en)

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CN113735809A (en) * 2021-09-25 2021-12-03 长春海谱润斯科技股份有限公司 Arylamine derivative and organic electroluminescent device thereof
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