CN115974822A - Arylamine compound and organic electroluminescent device thereof - Google Patents
Arylamine compound and organic electroluminescent device thereof Download PDFInfo
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Abstract
The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof. The arylamine compound provided by the invention has the advantages of high refractive index, high glass transition temperature, good thermal stability and chemical stability, can be used as a covering layer material applied to an OLED device, can effectively improve the light transmittance of the device, can resist high temperature, and can effectively isolate water vapor, oxygen and corrosive gas, thereby delaying the aging of the device, further improving the luminous efficiency of the device and prolonging the service life of the device.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof.
Background
Organic Light-Emitting diodes (OLEDs) have characteristics of being Light and thin in body state, wide in viewing angle, fast in response speed, wide in use temperature range, low in energy consumption, high in efficiency, good in color purity, high in definition, good in flexibility and the like, are widely used in the fields of illumination and display, and are considered to be one of display and illumination technologies with the greatest development prospects in the industry.
The classical OLED device is in a sandwich structure, a light emitting layer is sandwiched between a cathode and an anode, wherein the light emitting layer contains a luminescent substance (guest material), a certain working voltage is applied between the two electrodes, so that holes and electrons are respectively injected from the anode and the cathode and then reach the light emitting layer, excitons are generated through recombination to release energy, the excitons migrate under the action of an electric field to transfer the energy to the luminescent substance, electrons in the luminescent substance molecules jump from a ground state to an excited state, and the electrons return from the excited state to the ground state due to instability of the excited state, so that the energy is released in the form of light to generate a light emitting phenomenon. In order to improve the performance of the device, more organic functional layers are arranged between the anode and the light-emitting layer and between the cathode and the light-emitting layer, generally, a hole transport region is arranged between the anode and the light-emitting layer and mainly plays a role in injecting and transporting holes, and comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer and the like; an electron transport region is arranged between the cathode and the light-emitting layer, and mainly plays a role in injecting and transporting electrons, and comprises an electron injection layer, an electron transport layer, a hole blocking layer and the like.
In addition to the provision of the functional layer between the anode and the cathode, a cover layer is also provided on the outer side of the electrode on the light-emitting side (the side facing away from the electrode on the non-light-emitting side). In general, the cover layer has a high refractive index, and can improve light transmittance of the device, change the light emission direction, and the like, thereby improving the light emission efficiency, color purity, and the like of the device.
In order to further improve the performance of the OLED device, such as luminous efficiency, color purity, and lifetime, it is necessary to develop a cover material with excellent performance.
Disclosure of Invention
In order to solve the technical problems, the invention provides an arylamine compound which has good thermal stability and chemical stability and higher refractive index, can be used as a covering layer material to be applied to an OLED device, improves the performances of the OLED device such as luminous efficiency, service life and the like, and has a structure shown in a formula (I):
wherein, ar is 1 Selected from the structures of formula (I-A):
in the formula (I-A), X is selected from oxygen atom or sulfur atom; a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazineOne of an oxazoline group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted acridinyl group, and a substituted or unsubstituted triphenylene group; said R 1 、R 2 Independently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
ar is 3 Selected from the structures represented by the formula (I-B):
in the formula (I-B), Y is selected from oxygen atom or sulfur atom; the B and the C are independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted anthryl, and the B and the C are not selected from substituted or unsubstituted phenyl at the same time;
ar is 2 One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a structure shown in a formula (I-A) and a structure shown in a formula (I-B);
said L 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;
the substituent in the above "substituted or unsubstituted" is selected from deuterium atoms; a fluorine atom; a cyano group; C1-C4 alkyl substituted or unsubstituted by at least one of deuterium atom and fluorine atom; C5-C10 cycloalkyl substituted or unsubstituted with one or more members selected from the group consisting of deuterium atoms, fluorine atoms, cyano groups, and C1-C4 alkyl groups; C6-C12 aryl substituted or unsubstituted by at least one of deuterium atom, fluorine atom, cyano, C1-C4 alkyl and C5-C10 cycloalkyl; C2-C12 heteroaryl which is substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, C1-C4 alkyl group and C5-C10 cycloalkyl group.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a hole transmission area, a light-emitting layer, an electron transmission area and a covering layer of the cathode, wherein the hole transmission area, the light-emitting layer and the electron transmission area are arranged between the anode and the cathode, the covering layer is arranged on the side, away from the anode, of the cathode, and the organic layer contains more than one of the arylamine compounds.
Has the advantages that:
the arylamine compound provided by the invention has high refractive index, high glass transition temperature, good thermal stability and chemical stability, can be used as a covering layer material applied to an OLED device, can effectively improve the light transmittance of the device, can resist high temperature, and can effectively isolate water vapor, oxygen and corrosive gas, thereby delaying the aging of the device, further improving the luminous efficiency of the device and prolonging the service life of the device.
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.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom and includes atoms in both their natural isotopic abundance and unnatural abundance. In the case of hydrogen, all naturally occurring compounds contain about 0.0156 atomic% deuterium per hydrogen atom.
In the present invention, the use of "H" and "hydrogen atom" means that the hydrogen atom in the chemical structure contains no more than natural abundance of deuterium or tritium atoms, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atoms" refer to deuterium content in abundance above natural abundance, e.g., any value greater than 0.1 atomic%, greater than 1 atomic%, greater than 10 atomic%, e.g., where about 95 atomic% is deuterium. "T" and "tritium atom" refer to tritium content in abundance above natural abundance, e.g., any value greater than 0.1 atomic%, greater than 1 atomic%, greater than 10 atomic%, e.g., where about 95% is tritium. In the present invention, hydrogen not shown is omitted to mean "H" or "hydrogen atom".
The halogen atom in the present invention means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, the isomeric form of n-pentyl, the isomeric form of n-hexyl, the isomeric form of n-heptyl, the isomeric form of n-octyl, the isomeric form of n-nonyl, the isomeric form of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
The cycloalkyl group in the present invention means a hydrocarbon group formed by dropping one hydrogen atom from a cycloalkane molecule, and preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, and the like. The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group or a norbornyl group.
The cycloalkenyl group in the present invention means a hydrocarbon group formed by dropping one hydrogen atom from a cycloolefin molecule, and preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like, but are not limited thereto. The cycloalkyl group is preferably a cyclopentenyl group or a cyclohexenyl group.
The heterocycloalkyl group in the present invention is a group formed by removing one hydrogen atom from a heterocyclic molecule in which the ring-constituting atoms contain at least one heteroatom in addition to carbon atoms, the heteroatom including a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a selenium atom, a phosphorus atom, and the like, and preferably a nitrogen atom, an oxygen atom, a sulfur atom, and the like. Preferably 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. Preferably 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, ethylene sulfide, propylidene, tetrahydropyrrole, piperidyl, morpholinyl, thiomorpholinyl, piperazinyl, and the like, but are not limited thereto. The heterocyclic group is preferably a tetrahydropyrrolyl group, a piperidyl group, a morpholinyl group, a thiomorpholinyl group or a piperazinyl group.
The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and may be monocyclic aryl group, polycyclic aryl group, condensed ring aryl group or condensed group of aryl group and alicyclic ring, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl group, terphenyl group and the like, but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in a molecule and condensed by sharing two adjacent carbon atoms with each other, and examples thereof include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl and the like, but are not limited thereto. The above aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirobifluorenyl group, a spiro-cyclopentyl-fluorenyl group, a spiro-cyclohexyl-fluorenyl group, a spiro-adamantyl-fluorenyl group, a spiro-cyclopentenyl-fluorenyl group, or a spiro-cyclohexenyl-fluorenyl group.
The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atom, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group or a phenoxathiyl group.
The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of aryl groups provided above can be applied with respect to it, except that the arylene group is a divalent group.
The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, i.e., a divalent group. The description of heteroaryl provided above can be applied with respect to heteroarylene, except that heteroarylene is a divalent group.
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 position of substitution 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 "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 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C60 aryl group, substituted or unsubstituted C6 to C60 aryloxy group, substituted or unsubstituted C2 to C60 heteroaryl group, silyl group, preferably deuterium atom, halogen atom, cyano group, nitro group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C3 to C12 cycloalkenyl group, C3 to C12 heterocycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, silyl group, and when substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, methyl-substituted cyclopropane group, ethyl-substituted cyclopropane group, deuterated cyclopropane group, cyclobutane group, methyl-substituted cyclobutane group, ethyl-substituted cyclobutane group, deuterated cyclobutane group, cyclopentyl group, methyl-substituted cyclopentyl group, ethyl-substituted cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, methyl-substituted cyclohexyl group, ethyl-substituted cyclohexyl group, n-propyl-substituted cyclohexyl group, n-butyl-substituted cyclohexyl group, cyclohexane-substituted cyclohexyl group, deuterated cyclohexyl group, cycloheptyl group, cyclopentenyl group, methyl-substituted cyclopentenyl group ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthrenyl, deuterated phenanthrenyl, triphenylenyl, pyrenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, and in the case of substitution with a plurality of substituents, the plurality of substituents may be the same or different from each other.
In the present specification, when the position of a substituent or attachment site on an aromatic ring is not fixed, it means any of optional sites that can be attached to the aromatic ring. For example,
can indicate->
And so on.
In the present specification, when a bond at a substituent or attachment site is present throughout two or more rings, it is indicated that it may be attached to either of the two or two rings, in particular to either of the corresponding alternative sites of the rings. For example,
can signify->
Can indicate->
And so on.
The connection to form a ring structure (e.g., a saturated or unsaturated C3 to C10 carbocyclic ring, a substituted or unsubstituted saturated or unsaturated C3 to C6 carbocyclic ring) according to the present invention means that the respective groups are connected to each other by a chemical bond, and optionally form a double/triple bond, and may constitute an aromatic group, as exemplified below:
in the present invention, the ring to be connected may be an aromatic ring system, an aliphatic ring system, or a ring system formed by a fusion of the two, and the ring to be connected may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentobenzene, cyclohexene, cyclohexane, cyclohexan, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but not limited thereto.
The invention provides an arylamine compound, which has a structure shown in a formula (I):
wherein, ar is 1 Selected from the structures of formula (I-A):
in the formula (I-A), X is selected from oxygen atom or sulfur atom; a is selected from substituted or unsubstituted phenyl, substituted or unsubstitutedOne of a pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted triphenylene group of (b); said R 1 、R 2 Independently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
ar is 3 Selected from the structures represented by the formula (I-B):
in the formula (I-B), Y is selected from oxygen atom or sulfur atom; the B and the C are independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted anthryl, and the B and the C are not selected from substituted or unsubstituted phenyl at the same time;
ar is 2 One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a structure shown in a formula (I-A) and a structure shown in a formula (I-B);
said L 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;
the substituent in the above "substituted or unsubstituted" is selected from deuterium atoms; a fluorine atom; a cyano group; C1-C4 alkyl substituted or unsubstituted by at least one of deuterium atom and fluorine atom; C5-C10 cycloalkyl substituted or unsubstituted with one or more members selected from the group consisting of deuterium atoms, fluorine atoms, cyano groups, and C1-C4 alkyl groups; C6-C12 aryl substituted or unsubstituted by at least one of deuterium, fluorine, cyano, C1-C4 alkyl, and C5-C10 cycloalkyl; C2-C12 heteroaryl substituted or unsubstituted by at least one of deuterium, fluorine, cyano, C1-C4 alkyl, and C5-C10 cycloalkyl.
Preferably, said substituent in "substituted or unsubstituted" is selected from deuterium atoms; a fluorine atom; a cyano group; a methyl group; a trifluoromethyl group; a deuterated methyl group; an ethyl group; a deuterated ethyl group; n-propyl; isopropyl group; deuterated isopropyl; n-butyl; sec-butyl; an isobutyl group; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group which is substituted or unsubstituted by more than one of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; a cyclohexyl group which is substituted or unsubstituted with one or more groups selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, and a deuterated tert-butyl group; norbornyl which is unsubstituted or substituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; phenyl unsubstituted or substituted by one or more members selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; naphthyl substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group; furyl substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group; thienyl substituted or unsubstituted by more than one of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; a benzofuranyl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, and a deuterated tert-butyl group; benzothienyl substituted or unsubstituted by more than one of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; dibenzofuranyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group; dibenzothienyl substituted or unsubstituted by at least one of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; a pyridyl group which is unsubstituted or substituted with one or more members selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; a pyrimidinyl group which is unsubstituted or substituted with one or more members selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, and a deuterated tert-butyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; pyrazinyl which is substituted or unsubstituted with one or more members selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group; a pyridazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, and a deuterated tert-butyl group; a quinolyl group which is unsubstituted or substituted by at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group; a quinoxalinyl group substituted or unsubstituted with one or more members of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group and a deuterated tert-butyl group; one of quinazoline groups which are substituted or unsubstituted by more than one of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group, wherein the substituent group is one or more, and when the substituent group is a plurality, the plurality of substituent groups are the same or different.
Preferably, the formula (I-A) is selected from one of the following structures:
wherein, X is selected from oxygen atom or sulfur atom;
each occurrence of said a is selected, identically or differently, from 0,1, 2 or 3; each occurrence of said b is, identically or differently, selected from 0,1 or 2; each occurrence of said c is, identically or differently, selected from 0 or 1; each occurrence of d is, identically or differently, selected from 0,1, 2,3 or 4;
r is as described 1 、R 2 Independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl substituted or unsubstituted cyclohexane group, substituted or unsubstituted adamantyl group,One of substituted or unsubstituted norbornanyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
said R 3 Each occurrence, the same or different, is one selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
Preferably, R is 1 、R 2 Independently selected from hydrogen atoms; a deuterium atom; a fluorine atom; a cyano group; a methyl group substituted or unsubstituted with one or more members of the group consisting of deuterium atoms and fluorine atoms; isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; substituted or unsubstituted by more than one member of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl groupNorbornyl of (a); phenyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group and phenanthryl group; naphthyl substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a phenanthryl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a triphenylene group; deuterated triphenylene; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; a terphenyl group substituted or unsubstituted with one or more members of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; deuteriumA substituted pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; triazinyl substituted or unsubstituted with one or more of phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; a phenylcarbazolyl group; one of deuterated phenylcarbazolyl.
Preferably, R is 3 Each occurrence, identically or differently, is selected from hydrogen atoms; a deuterium atom; a fluorine atom; a cyano group; a methyl group substituted or unsubstituted with one or more members of the group consisting of deuterium atoms and fluorine atoms; isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; norbornyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl group; phenyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group and phenanthryl group; naphthyl substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; by deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, naphthyl groupOne or more substituted or unsubstituted phenanthryl groups; a triphenylene group; deuterated triphenylene; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; a terphenyl group substituted or unsubstituted with one or more members of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; dibenzothienyl; deuterated dibenzothienyl; a phenylcarbazolyl group; one of deuterated phenylcarbazolyl.
Preferably, the formula (I-A) is selected from one of the following structures:
preferably, the formula (I-B) is selected from one of the following structures:
wherein Y is selected from an oxygen atom or a sulfur atom;
a is as described 11 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; b is 11 Each occurrence, identically or differently, is selected from 0,1 or 2; c is as described 11 Each occurrence, identically or differently, is selected from 0,1, 2 or 3;
said R 11 Each occurrence, the same or different, is selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, a deuterated biphenyl group;
said R 12 At each occurrence, the same or different is one selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group.
Preferably, the formula (I-B) is selected from one of the following structures:
preferably, ar is 2 One selected from the group consisting of the structure represented by the following formula (I-A), the structure represented by the formula (I-B):
wherein, the a 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4 or 5; b is 21 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; c is as described 21 Each occurrence, identically or differently, is selected from 0,1, 2 or 3; d is 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5 or 6; the above-mentioned is/are as follows e.g. of the type 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7 or 8; f is 21 Each occurrence, identically or differently, is selected from 0,1 or 2; g is 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7,8, 9 or 10; h is as described 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13, or 14; i.e. i 21 Each occurrence, identically or differently, is selected from 0 or 1;
said R 21 Each occurrence, identically or differently, is selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro groupOne of a dibenzoenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group;
r is as described 22 One selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
Preferably, R is 21 Each occurrence, identically or differently, is selected from hydrogen atoms; a deuterium atom; a fluorine atom; a cyano group; a methyl group substituted or unsubstituted with one or more members of the group consisting of deuterium atoms and fluorine atoms; isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; norbornyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl group; phenyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group and phenanthryl group; naphthyl substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; by deuterium atoms, fluorine atoms, cyanogenOne or more substituted or unsubstituted biphenyl groups selected from the group consisting of a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group and a norbornyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a phenanthryl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a triphenylene group; deuterated triphenylene; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted by one or more members of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; a quinolyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; one of phenylcarbazolyl.
Preferably, R is 22 Each occurrence, identically or differently, is selected from the group consisting of,One or more substituted or unsubstituted phenyl groups selected from the group consisting of deuterated naphthyl, anthryl and phenanthryl; naphthyl substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a phenanthryl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a triphenylene group; deuterated triphenylene; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; triazinyl substituted or unsubstituted with one or more of phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; deuteriumA substituted dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; one of phenylcarbazolyl.
Preferably, ar is 2 One selected from the group consisting of the structure represented by the following formula (I-A), the structure represented by the formula (I-B):
preferably, said L 1 、L 2 Independently selected from a single bond or one of the structures shown below:
wherein, a is 41 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; b is 41 0,1, 2 or 3, the same or different, at each occurrence; c is as described 41 Each occurrence, identically or differently, is selected from 0,1 or 2; d is 41 Each occurrence, identically or differently, is selected from 0 or 1; said e 41 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5 or 6; f is 41 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7 or 8;
said R 41 Each occurrence is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a deuterated adamantyl group, a norbornyl group, a deuterated norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group.
Preferably, said L 1 、L 2 Independently selected from single bonds or the following structuresIn the structure one of them is:
most preferably, the arylamine compound is selected from one of the following compounds:
the arylamine compounds shown in the formula (I) are only partially specified in the structural form, but the invention is not limited to the specified chemical structures, and all the arylamine compounds based on the formula (I) have the substituent defined in the invention.
The arylamine compound shown in the formula (I) can be prepared by one of the following synthetic routes:
the first synthetic route is as follows:
the second synthetic route is as follows:
the third synthetic route is as follows:
wherein, X is 1 、X 2 Independently selected from a chlorine atom, a bromine atom or an iodine atom;
said L 1 ～L 3 、Ar 1 ～Ar 3 Are all as described herein.
In each synthetic route, the arylamine compound (Y1) and the halides (Y2) and (Y3) are subjected to Buchwald-Hartwig coupling reaction to obtain the target compound (I). The reaction sequence of the arylamine compound (Y1) with the halides (Y2) and (Y3) is not limited, and the arylamine compound (Y1) may be reacted with (Y2) first and then with (Y3), may be reacted with (Y3) first and then with (Y2), and may be reacted with (Y2) and (Y3) simultaneously.
The above reaction routes are each a reaction type commonly used in organic synthesis, and the reaction conditions (for example, selection of the kind of reaction solvent, catalyst, ligand, base, etc., the amount to be used, and the order and method of addition) are not particularly limited. The preparation method has the advantages of easily available raw materials, simple preparation process and excellent yield. The compound shown in formula (I) provided by the present invention can also be synthesized by using conventional reaction types in other organic synthesis, and the above is only an example of the synthetic route without particular limitation.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a hole transmission area, a light-emitting layer, an electron transmission area and a covering layer of the cathode, wherein the hole transmission area, the light-emitting layer and the electron transmission area are arranged between the anode and the cathode, the covering layer is arranged on the side, away from the anode, of the cathode, and the organic layer contains more than one of the arylamine compounds.
Preferably, the organic layer comprises a covering layer on the side of the cathode away from the anode, and the covering layer contains more than one of the arylamine compounds.
Preferably, the organic layer includes a hole transport region between the anode and the cathode, a light emitting layer, an electron transport region, and a cover layer on a side of the cathode away from the anode, and the cover layer contains one or more of the arylamine compounds of the present invention.
The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emission auxiliary layer.
Preferably, the hole transport region includes at least two layers of a hole injection layer, a hole transport layer and a light emission auxiliary layer; further preferably, the hole transport region includes a hole injection layer and a hole transport layer.
Preferably, the hole transport region includes a hole injection layer, a hole transport layer and a light emission auxiliary layer.
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, for example, 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' -tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), compounds HT-1 to HT-19, and compounds p-1 to p-3 can be used, but not limited thereto.
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. Triarylamine compounds may be used, as well as other hole mobilities at 10 -6 cm 2 Examples of the substance having a structure of/Vs or more include, but are not limited to, N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4' -tris (N, N-diphenylamino) triphenylamine (TDATA), and the compounds HT-1 to HT-19 described above.
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. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, and other compounds having suitable HOMO and T1 energy levels may be used, and examples thereof include TPD, NPB, 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, compounds HT-1 to HT-19 as shown above, but not limited thereto.
The light-emitting layer of the present invention includes a guest material and a host material, and a dual host material formed of two host materials may be used. As the guest material, a fluorescent compound such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative or the like can be used, and examples thereof include 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro-1, 7-tetramethyl-1H, 5H,11H- [ 1H 1]Benzopyran [6,7,8-ij]Quinolizin-11-one (C545T), 4' -bis (9-ethyl-3-carbazolevinyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), etc., and phosphorescent light-emitting materials such as iridium complexes, osmium complexes, platinum complexes, etc., may also be used, and examples thereof include bis (4, 6-difluorophenylpyrazole)pyridine-N, C2-pyridinecarboxylic iridium (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, a benzoxazole derivative, a benzothiazole derivative or a benzimidazole derivative, an aromatic amine compound such as a fused aromatic compound such as a carbazole derivative or an anthracene derivative, a triarylamine derivative or a fused polycyclic aromatic amine derivative, and examples thereof include Alq 3 BAlq, TPBI, TPD, 4 '-bis (9-Carbazole) Biphenyl (CBP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), but are not limited thereto.
The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.
Preferably, the electron transport region comprises at least two layers of an electron injection layer, an electron transport layer and a hole blocking layer; further preferably, the electron transport region includes an electron injection layer and an electron transport layer.
Preferably, the electron transport region includes 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, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, etc., but are not limited thereto.
The electron transport layer of the invention can be a single materialThe layer structure may be a single layer structure or a multilayer structure composed of different substances, and aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, and the like having high electron transport properties can be used, and examples thereof include 8-hydroxyquinoline aluminum (Alq) 3 ) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq 2 ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BALq), 2- (4-biphenyl) -5-Phenyloxadiazole (PBD), 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 that the T1 energy level is higher than that of the light-emitting layer, so that the energy loss of the light-emitting layer can be blocked. 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 -6 cm 2 and/Vs or above, the electron transmission is facilitated. One or more of the following may be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymer compounds, and the like. Examples include, but are not limited to, 1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), BALq and the like.
The anode of the present invention may be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or an alloy thereof, or may have a transparent or semi-transparent layer structure having a high work function, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), aluminum Zinc Oxide (AZO), indium Gallium Oxide (IGO), indium oxide (In) 2 O 3 ) Or tin oxide (SnO) 2 ) The layer structure formed depends on the type of device to be prepared, such as bottom emitting device (anode side emitting) and transparent deviceOr a semi-transparent anode, if the desired device to be made is a top-emitting device (cathode side emitting), a reflective anode is desired.
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 covering layer of the present invention may be a single-layer structure made of a single substance, or a single-layer structure or a multi-layer structure made of different substances. The coating material may be an organic or inorganic material having an appropriate refractive index, and examples thereof include metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, and aromatic amine compounds, and include LiF, csF, and MgF 2 、CaF 2 、CsCl、CuI、V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、ZnS、Alq 3 The compound CP-1, the compound CP-2, the compound CP-3, the compound CP-4 and the arylamine compound are not limited.
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 200nm. 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 fields of illumination, display and the like, and can be specifically listed as a display screen of a smart phone, a display screen of a tablet personal computer, a display screen of intelligent wearable equipment, a large-size display such as a television, VR (virtual reality), 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;
for the elemental analysis, a Vario EL cube type organic element analyzer from Elementar, germany was used, and the sample mass was 5 to 10mg.
Synthesis example 1: synthesis of intermediate AA/BB
Aa-32 (24.58g, 90.00mmol), bb-32 (12.25g, 90.00mmol), pd (PPh) were added to the reaction flask under argon shield 3 ) 4 (1.27g, 1.10 mmol), potassium carbonate (16.59g, 120.00mmol) and 600mL of a toluene/ethanol/water (2. After the reaction is finished, cooling to room temperature, adding methylbenzene to separate each phase, washing the methylbenzene phase with distilled water for three times, drying with anhydrous magnesium sulfate, carrying out rotary evaporation and concentration on the solvent, cooling and crystallizing, carrying out suction filtration, and recrystallizing the obtained solid with toluene to obtain an intermediate AA-32 (21.06 g, yield 82%); purity by HPLC ≧ 99.77%. Mass spectrum m/z:285.1169 (theoretical value: 285.1154).
According to the above synthesis method, other intermediates AA/BB required by the present invention are synthesized, and related raw materials are shown in Table 101:
table 101:
synthesis example 2: synthesis of Compound 17
Synthesis of intermediate CC-17:
adding AA-17 (14.60g, 60.00mmol), AA-473 (16.39g, 60.00mmol) and Pd (OAc) into a reaction bottle under the protection of argon 2 (0.16g，0.70mmol)、P(t-Bu) 3 (0.14g, 0.70mmol), sodium t-butoxide (9.61g, 100.00mmol) and 300ml of toluene were stirred, and the mixture was heated under reflux for 5 hours. After the reaction, the reaction mixture was cooled to room temperature, distilled water was added, dichloromethane was used for extraction, the mixture was allowed to stand for liquid separation, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, filtered, and finally recrystallized from toluene/methanol (10). Mass spectrum m/z:435.1636 (theoretical value: 435.1623).
Synthesis of compound 17:
under the protection of argon, CC-17 (13.07g, 30.00mmol), DD-17 (8.91g, 30.00mmol) and Pd are added into a reaction bottle 2 (dba) 3 (0.37g, 0.40mmol), BINAP (0.50g, 0.80mmol), sodium tert-butoxide (4.81g, 50mmol) and 150ml of toluene were stirred and the above system was heated under reflux for 7 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane, allowed to stand for liquid separation, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, filtered with suction, and finally recrystallized from toluene/methanol (10) to obtain compound 17 (14.47g, 74%) with an HPLC purity ≧ 99.97%. Mass spectrum m/z:651.2212 (theoretical value: 651.2198). Theoretical element content (%) C 48 H 29 NO 2 : c,88.46; h,4.49; and N,2.15. The measured element content (%) C,88.50; h,4.52; and N,2.10.
Synthetic example 3: synthesis of Compound 31
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-31, BB-31 and DD-31 to give compound 31 (15.38 g) having a solid purity of 99.95% or higher by HPLC. Mass spectrum m/z:711.3128 (theoretical value: 711.3137). Theoretical element content (%) C 52 H 41 NO 2 : c,87.73; h,5.81; and N,1.97. Measured elemental content (%): c,87.69; h,5.78; and N,2.01.
Synthetic example 4: synthesis of Compound 32
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar amounts of AA-32 and BB-32 to give compound 32 (15.33 g) having a solid purity of 99.95% or higher by HPLC. Mass spectrum m/z:709.2970 (theoretical value: 709.2981). Theoretical element content (%) C 52 H 39 NO 2 : c,87.98; h,5.54; n,1.97. Measured elemental content (%): c,88.03; h,5.53; and N,1.95.
Synthesis example 5: synthesis of Compound 70
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar amounts of AA-70 and BB-70 to give compound 70 (13.26 g), which was purified by HPLC to give a solid having a purity of 99.99% or more. Mass spectrum m/z:581.2309 (theoretical value: 581.2293). Theoretical element content (%) C 42 H 23 D 4 NO 2 : c,86.72; h,5.37; and N,2.41. Measured elemental content (％)：C,86.69；H,5.41；N,2.38。
Synthetic example 6: synthesis of Compound 85
The same procedures were carried out except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-85, BB-85 and DD-85 to give compound 85 (17.01 g), which had a solid purity of 99.91% or higher as determined by HPLC. Mass spectrum m/z:833.2741 (theoretical value: 833.2752). Theoretical element content (%) C 61 H 39 NOS: c,87.85; h,4.71; n,1.68. Measured elemental content (%): c,87.87; h,4.66; n,1.73.
Synthetic example 7: synthesis of Compound 105
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar AA-105 and BB-105 to give compound 105 (15.76 g) having a solid purity of 99.94% or higher by HPLC. Mass spectrum m/z:739.2528 (theoretical value: 739.2511). Theoretical element content (%) C 55 H 33 NO 2 : c,89.29; h,4.50; n,1.89. Measured elemental content (%): c,89.32; h,4.47; n,1.94.
Synthesis example 8: synthesis of Compound 113
Compound 113 (13.90 g) was obtained by replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-113, BB-113 and DD-113 in the same manner as in the previous step, and the purity of solid was 99.98% or more by HPLC. Mass spectrum m/z:617.1826 (theoretical value: 617.1813). Theoretical element content (%) C 44 H 27 NOS: c,85.55; h,4.41; and N,2.27. Measured elemental content (%): c,85.51; h,4.39; n,2.31.
Synthetic example 9: synthesis of Compound 159
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar amounts of AA-159 and BB-159 to give 159 (14.26 g) having a solid purity of 99.98% or higher by HPLC. Mass spectrum m/z:633.2450 (theoretical value: 633.2465). Theoretical element content (%) C 45 H 23 D 5 N 2 O 2 :85.28; h,5.25; n,4.42. Measured elemental content (%): 85.31 parts of; h,5.23; and N,4.45.
Synthesis example 10: synthesis of Compound 213
Compound 213 (13.92 g) was obtained by replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-213, BB-213 and DD-213 in the same manner as in the previous step, and the purity of solid was 99.97% or higher by HPLC. Mass spectrum m/z:618.2158 (theoretical value: 618.2150). Theoretical element content (%) C 42 H 18 D 9 NS 2 : c,81.51; h,5.86; and N,2.26. Measured elemental content (%): c,81.49; h,5.89; and N,2.28.
Synthetic example 11: synthesis of Compound 221
The same procedures as those used in Synthesis example 2 were repeated except for replacing AA-17, AA-473 and DD-17 with equimolar amounts of AA-221, AA-282 and DD-221 to give compound 221 (13.71 g), which was purified to 99.97% by HPLC. Mass spectrum m/z:617.1803 (theoretical value: 617.1813). Theoretical element content (%) C 44 H 27 NOS: c,85.55; h,4.41; and N,2.27. Measured elemental content (%): c,85.60; h,4.38; and N,2.29.
Synthetic example 12: synthesis of Compound 225
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-225, BB-225 and DD-225 to obtain compound 225 (15.33 g), which was purified by HPLC to give a solid having a purity of 99.95% or higher. Mass spectrum m/z:709.2451 (theoretical value: 709.2439). Theoretical element content (%) C 51 H 35 NOS: c,86.29; h,4.97; and N,1.97. Measured elemental content (%): c,86.33; h,5.01; n,1.92.
Synthetic example 13: synthesis of Compound 230
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-70, BB-230 and DD-230 to give compound 230 (13.51 g), which was purified by HPLC to give a solid having a purity of 99.99% or higher. Mass spectrum m/z:592.1623 (theoretical value: 592.1609). Theoretical element content (%) C 41 H 24 N 2 And OS: c,83.08; h,4.08; n,4.73. Measured elemental content (%): c,83.12; h,4.06; and N,4.75.
Synthesis example 14: synthesis of Compound 244
The same procedures were carried out except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-244, BB-244 and DD-244 to give 244 (15.68 g) having a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:735.2063 (theoretical value: 735.2054). Theoretical element content (%) C 52 H 33 NS 2 : c,84.86; h,4.52; and N,1.90. Measured elemental content (%): c,84.85; h,4.57; n,1.88.
Synthetic example 15: synthesis of Compound 264
Compound 264 (14.29 g) was obtained by replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-264, BB-264 and DD-264 in the same manner as in the previous step, and the purity of solid was 99.97% or higher by HPLC. Mass spectrum m/z:643.1982 (theoretical value:
643.1970). Theoretical element content (%) C 46 H 29 NOS: c,85.82; h,4.54; and N,2.18. Measured elemental content (%): c,85.79; h,4.55; and N,2.22.
Synthetic example 16: synthesis of Compound 281
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar AA-264 and BB-281 to give 281 (16.76 g) having a solid purity of 99.92% or higher by HPLC. Mass spectrum m/z:833.2734 (theoretical value: 833.2752). Theoretical element content (%) C 61 H 39 NOS: c,87.85; h,4.71; n,1.68. Measured elemental content (%): c,87.91; h,4.69; n,1.69.
Synthetic example 17: synthesis of Compound 282
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-225, BB-282 and DD-113 to give 282 (15.76 g) as a compound, which was purified by HPLC to a solid content of 99.94% or more. Mass spectrum m/z:739.2024 (theoretical value: 739.2004). Theoretical element content (%) C 51 H 33 NOS 2 : c,82.78; h,4.50; n,1.89. Measured elemental content (%): c,82.81; h,4.47; n,1.93.
Synthetic example 18: synthesis of Compound 302
The same procedures were carried out except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-302, BB-302 and DD-113 to give compound 302 (16.28 g), which was purified by HPLC to give a solid having a purity of 99.93% or higher. Mass spectrum m/z:774.2177 (theoretical value: 774.2163). Theoretical element content (%) C 54 H 34 N 2 S 2 : c,83.69; h,4.42; and N,3.61. Measured elemental content (%): c,83.73; h,4.39; and N,3.64.
Synthetic example 19: synthesis of Compound 317
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-317, BB-317 and DD-317 to give compound 317 (15.83 g) having a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:753.1973 (theoretical value: 753.1960). Theoretical element content (%) C 52 H 32 FNS 2 : c,82.84; h,4.28; n,1.86. Measured elemental content (%): c,82.82; h,4.31; n,1.88.
Synthesis example 20: synthesis of Compound 325
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-264, BB-335 and DD-325 to give compound 325 (14.99 g), which was purified by HPLC to give a solid having a purity of 99.95% or higher. Mass spectrum m/z:693.2141 (theoretical value: 693.2126). Theoretical element content (%) C 50 H 31 NOS: c,86.55; h,4.50; n is added to the reaction solution to form a reaction solution, 2.02. Measured elemental content (%): c,86.59; h,4.47; and N,1.99.
Synthetic example 21: synthesis of Compound 346
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar amounts of AA-346 and BB-346 to give 346 (13.49 g), which was purified by HPLC to give 99.98% or more. Mass spectrum m/z:591.1846 (theoretical value: 591.1834). Theoretical element content (%) C 42 H 25 NO 3 : c,85.26; h,4.26; n,2.37. Measured elemental content (%): c,85.29; h,4.25; and N,2.39.
Synthetic example 22: synthesis of Compound 350
The same procedures were carried out except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-350, BB-350 and DD-350 to give compound 350 (14.69 g), which had a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:670.2233 (theoretical value: 670.2225). Theoretical element content (%) C 47 H 26 D 2 N 2 O 3 : c,84.16; h,4.51; and N,4.18. Measured elemental content (%): c,84.13; h,4.47; n,4.22.
Synthetic example 23: synthesis of Compound 351
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-351, BB-351 and DD-351 to give Compound 351 (13.26 g), which had a solid purity of 99.97% or higher by HPLC. Mass spectrum m/z:581.1466 (theoretical value: 581.1449). Theoretical element content (%) C 40 H 23 NO 2 S: c,82.59; h,3.99; and N,2.41. Measured elemental content (%): c,82.64; h,4.01N,2.37.
Synthetic example 24: synthesis of Compound 366
The same procedures were repeated except for replacing AA-17 and DD-17 in Synthesis example 2 with equimolar amounts of AA-366 and DD-366 to give 366 (15.91 g), which had a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:746.2883 (theoretical value: 746.2871). Theoretical element content (%) C 54 H 30 D 4 N 2 O 2 : c,86.84; h,5.13; and N,3.75. Measured elemental content (%): c,86.81; h,5.15; n,3.78.
Synthetic example 25: synthesis of Compound 377
Adding AA-346 (4.00g, 30.00mmol), BB-377 (18.79g, 60.00mmol) and Pd into a reaction bottle under the protection of argon 2 (dba) 3 (0.64g, 0.70mmol), BINAP (0.87g, 1.40mmol), sodium tert-butoxide (9.61g, 100mmol) and 300ml of toluene were stirred and the above system was heated under reflux for 7 hours. After the reaction, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane, allowed to stand for liquid separation, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, filtered, and finally recrystallized from toluene/methanol (10. Mass spectrum m/z:597.1239 (theoretical value: 597.1221). Theoretical element content (%) C 40 H 23 NOS 2 : c,80.37; h,3.88; and N,2.34. The actual element content (%) C,80.40; h,3.92; and N,2.29.
Synthetic example 26: synthesis of Compound 378
The AA-17, AA-473 and DD-17 in the synthesis example 2 were replaced by equimolar AA-378,BB-378 and DD-264 were carried out in the same manner, so as to obtain compound 378 (16.46 g) having a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:783.2218 (theoretical value: 783.2232). Theoretical element content (%) C 56 H 33 NO 2 S: c,85.80; h,4.24; n,1.79. Measured elemental content (%): c,85.77; h,4.25; n,1.83.
Synthetic example 27: synthesis of Compound 389
The AA-17, AA-473 and DD-17 in the synthesis example 2 are replaced by equimolar AA-389, BB-389 and DD-389, the other steps are the same, and the compound 389 (15.13 g) is obtained, and the purity of the solid is not less than 99.96% through HPLC (high performance liquid chromatography). Mass spectrum m/z:690.2367 (theoretical value: 690.2358). Theoretical element content (%) C 48 H 22 D 7 NO 2 S: c,83.45; h,5.25; and N,2.03. Measured elemental content (%): c,83.41; h,5.27; and N,2.01.
Synthetic example 28: synthesis of Compound 413
The same procedures were repeated except for replacing AA-17 and AA-473 in Synthesis example 2 with equimolar AA-413 and BB-413 to give 413 (14.04 g) of a compound having a solid purity of 99.97% or higher by HPLC. Mass spectrum m/z:623.1391 (theoretical value: 623.1378). Theoretical element content (%) C 42 H 25 NOS 2 : c,80.87; h,4.04; and N,2.25. Measured elemental content (%): c,80.91; h,4.06; and N,2.22.
Synthetic example 29: synthesis of Compound 427
The AA-17, AA-473 and DD-17 in synthetic example 2 were replaced with equimolar AA-31, BB-244 and DD-225 was obtained in the same manner as in the other steps to obtain compound 427 (13.58 g), which was not less than 99.98% in solid purity by HPLC. Mass spectrum m/z:595.1728 (theoretical value: 595.1718). Theoretical element content (%) C 40 H 25 N 3 And (3) OS: c,80.65; h,4.23; and N,7.05. Measured elemental content (%): c,80.67; h,4.26; and N,7.04.
Synthetic example 30: synthesis of Compound 430
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-346, BB-430 and DD-325 to give compound 430 (13.49 g), which was purified by HPLC to give a solid having a purity of 99.99% or more. Mass spectrum m/z:591.1849 (theoretical value: 591.1834). Theoretical element content (%) C 42 H 25 NO 3 : c,85.26; h,4.26; n,2.37. Measured elemental content (%): c,85.27; h,4.23; and N,2.41.
Synthetic example 31: synthesis of Compound 471
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-471, BB-471 and DD-366 to give compound 471 (14.28 g), which had a solid purity of 99.97% or higher as determined by HPLC. Mass spectrum m/z:634.1703 (theoretical value: 634.1715). Theoretical element content (%) C 43 H 26 N 2 O 2 S: c,81.37; h,4.13; n,4.41. Measured elemental content (%): c,81.39; h,4.16; n,4.39.
Synthetic example 32: synthesis of Compound 473
Substitution of AA-346 and BB-377 in Synthesis example 25 with equimolar AA-473 and BB-473The same procedure was repeated to give compound 473 (16.17 g) having a purity of 99.96% or more on HPLC. Mass spectrum m/z:769.2634 (theoretical value: 769.2617). Theoretical element content (%) C 56 H 35 NO 3 : c,87.36; h,4.58; n,1.82. Measured elemental content (%): c,87.40; h,4.61; n,1.78.
Synthetic example 33: synthesis of Compound 497
The compound 497 (16.51 g) was obtained by replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar AA-85, BB-497 and DD-225, and the purity of solid was ≧ 99.95% by HPLC. Mass spectrum m/z:785.2375 (theoretical value: 785.2389). Theoretical element content (%) C 56 H 35 NO 2 S: c,85.58; h,4.49; n,1.78. Measured elemental content (%): c,85.61; h,4.51N,1.76.
Synthesis example 34: synthesis of Compound 500
The same procedures were repeated except for replacing AA-17, AA-473 and DD-17 in Synthesis example 2 with equimolar amounts of AA-500, BB-264 and DD-500 to give compound 500 (14.43 g), which was purified by HPLC to give a solid having a purity of 99.96% or higher. Mass spectrum m/z:658.2110 (theoretical value: 658.2099). Theoretical element content (%) C 44 H 18 D 9 NOS 2 : c,80.21; h,5.50; and N,2.13. Measured elemental content (%): c,80.19; h,5.47; and N,2.14.
Synthetic example 35: synthesis of Compound 501
The AA-346 and BB-377 in Synthesis example 25 were replaced by equimolar AA-31 and BB-501, and the other steps were the sameCompound 501 (14.51 g) was obtained, and the purity of the solid by HPLC ≧ 99.97%. Mass spectrum m/z:653.1331 (theoretical value: 653.1344). Theoretical element content (%) C 40 H 23 N 5 OS 2 : c,73.49; h,3.55; n,10.71. Measured elemental content (%): c,73.55; h,3.53; n,10.69.
Synthetic example 36: synthesis of Compound 545
The same procedures as those used in synthesis example 2 were repeated except for replacing AA-17, AA-473 and DD-17 with equimolar AA-471, BB-545 and DD-366 to give compound 545 (14.08 g) having a purity of 99.98% or more by HPLC. Mass spectrum m/z:617.1977 (theoretical value: 617.1991). Theoretical element content (%) C 44 H 27 NO 3 : c,85.56; h,4.41; and N,2.27. Measured elemental content (%): c,85.58; h,4.38; n,2.31.
The organic materials in the device preparation examples are purified by sublimation, and the purity is over 99.99 percent. ITO glass substrates and ITO/Ag/ITO glass substrates used in the device production examples were commercially available.
The following are other compounds used in the device preparation examples than the arylamine compound described in the present invention:
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 temperature 2 Luminous 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 table 1.
Comparative device preparation example 1: comparison device 1
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.
On the ITO/Ag/ITO glass substrate evaporating the following layers layer by layer: a. HT-3 and p-1 (the mass ratio is 100; b. HT-3 is used as a hole transport layer and has the thickness of 35nm; c. RH-1, RH-2 and Ir (dpm) (piq) 2 (mass ratio 64; d. TPBi is used as a hole blocking layer, and the thickness is 30nm; e. NBphen and Liq (mass ratio 7; f. LiF is used as an electron injection layer and has the thickness of 0.1nm; g. mg and Ag (mass ratio 1; h: CP-5 was used as a cap layer with a thickness of 100nm.
Comparative device preparation example 2: comparison device 2
Comparative device 2 was obtained by replacing CP-5 in the cap layer with CP-6, the remainder being the same as in comparative device preparation example 1.
Device preparation examples 1 to 35: light emitting devices 1 to 35
Light-emitting devices 1 to 35 were obtained by replacing CP-5 in the over-layer with the arylamine compound of the present invention in synthesis examples 2 to 36 and performing the same other steps as in comparative device preparation example 1.
TABLE 1
The device data in table 1 show that the arylamine compounds of the present invention, when applied as a capping layer material in an OLED device, have improved luminous efficiency and service life. In conclusion, the arylamine compound provided by the invention is an OLED material with excellent performance 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. An arylamine compound, characterized in that the arylamine compound has a structure represented by formula (I):
wherein, ar is 1 Selected from the structures of formula (I-A):
in the formula (I-A), X is selected from oxygen atom or sulfur atom; a is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted anthryl, substituted or unsubstituted acridinyl and substituted or unsubstituted triphenylene; said R 1 、R 2 Independently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
ar is 3 Selected from the structures of formula (I-B):
in the formula (I-B), Y is selected from oxygen atom or sulfur atom; the B and the C are independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted anthryl, and the B and the C are not selected from substituted or unsubstituted phenyl at the same time;
ar is 2 One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a structure shown in a formula (I-A) and a structure shown in a formula (I-B);
said L 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;
the substituent in the above "substituted or unsubstituted" is selected from deuterium atom; a fluorine atom; a cyano group; C1-C4 alkyl substituted or unsubstituted by at least one of deuterium atom and fluorine atom; C5-C10 cycloalkyl substituted or unsubstituted with one or more members selected from the group consisting of deuterium atom, fluorine atom, cyano group, and C1-C4 alkyl group; C6-C12 aryl substituted or unsubstituted by at least one of deuterium atom, fluorine atom, cyano, C1-C4 alkyl and C5-C10 cycloalkyl; C2-C12 heteroaryl which is substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, C1-C4 alkyl group and C5-C10 cycloalkyl group.
2. The arylamine compound according to claim 1, wherein the formula (I-a) is one selected from the following structures:
wherein, X is selected from oxygen atom or sulfur atom;
each occurrence of said a is selected, identically or differently, from 0,1, 2 or 3; each occurrence of said b is, identically or differently, selected from 0,1 or 2; each occurrence of said c is, identically or differently, selected from 0 or 1; each occurrence of said d is selected, identically or differently, from 0,1, 2,3 or 4;
said R 1 、R 2 One independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group;
r is as described 3 Each occurrence, identically or differently, is selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinoline groupOne of a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
3. The arylamine compound according to claim 2, wherein R is represented by 1 、R 2 Independently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a methyl group substituted or unsubstituted with one or more members of the group consisting of deuterium atoms and fluorine atoms; an isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl alkyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; norbornyl which is substituted or unsubstituted with one or more groups selected from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl group; phenyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group and phenanthryl group; naphthyl substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a phenanthryl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a triphenylene group; deuterated triphenylene; a bi-group substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group and norbornyl groupA phenyl group; a terphenyl group substituted or unsubstituted with one or more members of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; a phenyl carbazolyl group; one of deuterated phenylcarbazolyl;
r is as described 3 Each occurrence, identically or differently, is selected from hydrogen atoms; a deuterium atom; a fluorine atom; a cyano group; methyl substituted or unsubstituted by one or more of deuterium atom and fluorine atom; isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl alkyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; norbornyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl group; by deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl groupDeuterated tert-butyl, adamantyl, norbornyl, naphthyl, deuterated naphthyl, anthryl and phenanthryl; naphthyl substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; an anthracenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; phenanthryl substituted or unsubstituted with one or more members of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, and naphthyl group; a triphenylene group; deuterated triphenylene; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; a terphenyl group substituted or unsubstituted with one or more members of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; substituted phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenylOne or more substituted or unsubstituted triazinyl groups selected from the group consisting of phenyl and naphthyl; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; a phenyl carbazolyl group; one of deuterated phenylcarbazolyl.
4. The arylamine compound according to claim 1, wherein the formula (I-B) is one selected from the following structures:
wherein Y is selected from an oxygen atom or a sulfur atom;
a is described 11 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; b is 11 Each occurrence, identically or differently, is selected from 0,1 or 2; c is mentioned 11 Each occurrence, identically or differently, is selected from 0,1, 2 or 3;
said R 11 Each occurrence, identically or differently, is selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group;
said R 12 At each occurrence, the same or different is one selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group.
5. The arylamine compound according to claim 1, wherein Ar is 2 Selected from the structures shown as the following, formula (I-A)One of the structure shown and the structure shown in the formula (I-B):
wherein, the a 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4 or 5; b is 21 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; c is as described 21 Each occurrence, identically or differently, is selected from 0,1, 2 or 3; d is mentioned 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5 or 6; said e 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7 or 8; f is 21 Each occurrence, identically or differently, is selected from 0,1 or 2; g is described 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7,8, 9 or 10; h is as described 21 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7,8, 9,10, 11, 12, 13, or 14; i.e. i 21 Each occurrence, identically or differently, is selected from 0 or 1;
r is as described 21 Each occurrence, the same or different, is one selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group;
said R 22 One selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
6. The arylamine compound according to claim 5, wherein R is 21 Each occurrence, identically or differently, is selected from hydrogen atoms; a deuterium atom; a fluorine atom; a cyano group; methyl substituted or unsubstituted by one or more of deuterium atom and fluorine atom; isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentyl group; deuterated cyclopentyl; a cyclohexane group; a deuterated cyclohexyl group; an adamantyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; norbornyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group and tert-butyl group; phenyl which is substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group and phenanthryl group; naphthyl substituted or unsubstituted by at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, and deuterated naphthyl group; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; by deuterium atoms, fluorine atomsOne or more substituted or unsubstituted anthracenyl groups selected from the group consisting of cyano, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl and naphthyl; a phenanthryl group which is unsubstituted or substituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; a triphenylene group; deuterated triphenylene; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; a quinolyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl substituted or unsubstituted with one or more of deuterium atom, phenyl group, naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; dibenzothienyl; deuterated dibenzothienyl; one of phenyl carbazolyl groups;
said R 22 Phenyl groups, which are, identically or differently, substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a naphthyl group, a deuterated naphthyl group, an anthryl group, and a phenanthryl group, at each occurrence; by deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl groupOne or more substituted or unsubstituted naphthyl groups selected from the group consisting of norbornanyl, phenyl, deuterated phenyl, naphthyl, and deuterated naphthyl; biphenyl substituted or unsubstituted with at least one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group; an anthracene group substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group and a naphthyl group; phenanthryl substituted or unsubstituted with one or more members of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, and naphthyl group; a triphenylene group; deuterated tri a phenyl group; a fluorenyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; spirobifluorenyl substituted or unsubstituted with at least one member selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group and a deuterated biphenyl group; a quinolyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group; isoquinolinyl which is substituted or unsubstituted with one or more members selected from the group consisting of deuterium atom, phenyl group, and naphthyl group; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothienyl group; deuterated dibenzothienyl; one of phenylcarbazolyl.
7. The aryl of claim 1An amine compound characterized in that said L 1 、L 2 Independently selected from a single bond or one of the structures shown below:
wherein, a is 41 Each occurrence, identically or differently, is selected from 0,1, 2,3 or 4; b is 41 0,1, 2 or 3, the same or different, at each occurrence; c is as described 41 Each occurrence, identically or differently, is selected from 0,1 or 2; d is 41 On each occurrence, identically or differently selected from 0 or 1; said e 41 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5 or 6; f is 41 Each occurrence, identically or differently, is selected from 0,1, 2,3, 4,5, 6,7 or 8;
said R 41 Each occurrence, the same or different, is one selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a deuterated adamantyl group, a norbornyl group, a deuterated norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group.
8. The arylamine compound according to claim 1, wherein the arylamine compound is one compound selected from the group consisting of:
9. an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a hole transport region, a light emitting layer, an electron transport region between the anode and the cathode and a cover layer on the side of the cathode facing away from the anode, and wherein the organic layer contains one or more arylamine compounds according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises a capping layer on a side of the cathode facing away from the anode, wherein the capping layer comprises one or more arylamine compounds according to any one of claims 1 to 8.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332962A (en) * | 2023-03-28 | 2023-06-27 | 京东方科技集团股份有限公司 | Arylamine compound and display substrate |
| CN117024387A (en) * | 2023-10-09 | 2023-11-10 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332962A (en) * | 2023-03-28 | 2023-06-27 | 京东方科技集团股份有限公司 | Arylamine compound and display substrate |
| CN117024387A (en) * | 2023-10-09 | 2023-11-10 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
| CN117024387B (en) * | 2023-10-09 | 2024-02-02 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
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