CN117164574A - Nitrogen-containing condensed aromatic ring compound and organic electroluminescent device thereof - Google Patents

Nitrogen-containing condensed aromatic ring compound and organic electroluminescent device thereof Download PDF

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CN117164574A
CN117164574A CN202311118235.6A CN202311118235A CN117164574A CN 117164574 A CN117164574 A CN 117164574A CN 202311118235 A CN202311118235 A CN 202311118235A CN 117164574 A CN117164574 A CN 117164574A
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unsubstituted
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alicyclic
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郭建华
苗玉鹤
刘喜庆
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention provides a compound containing nitrogen condensed aromatic rings and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. In order to solve the problems in the prior art of the existing organic electroluminescent materials and devices, the invention provides a compound containing nitrogen condensed aromatic rings, which is used as a main material of an electron transport layer, a hole blocking layer and a luminescent layer to be applied to the organic electroluminescent devices, and can effectively improve the luminous efficiency, the driving voltage and the service life of the devices. The novel nitrogen-containing condensed aromatic ring organic compound has higher triplet state energy level, proper HOMO/LUMO energy level, higher electron affinity and electron mobility, is favorable for electron transmission, and enables hole and electron transmission to reach balance; in addition, the compound has higher decomposition temperature, higher glass transition temperature and better film forming property, can effectively ensure the stability and high efficiency of the device, and can obviously improve the luminous efficiency when being used as a main material of a luminous layer in an organic electroluminescent device.

Description

Nitrogen-containing condensed aromatic ring compound and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a compound containing nitrogen condensed aromatic rings and an organic electroluminescent device thereof.
Background
In recent years, organic electroluminescent devices (OLEDs, organic Light Emitting Diode) display and illumination are a new technology, and are used for the display and illumination of the technology because of the advantages of wide color gamut, simple structure, soft light color, fast response time, wide viewing angle, low driving voltage, thin panel and the like. At present, the display technology direction is mainly applied to directions of mobile phones, television display screens, illuminating lamps and the like at present, and the market share of the display technology direction is gradually expanded.
As organic electroluminescence research is more and more mature, the structure of the device is more and more complex, but most of the organic electroluminescent devices are multilayer sandwich type double-carrier (hole and electron) direct current injection devices. The cathode and anode are respectively composed of a cathode, an anode and an organic functional layer between the cathode and the anode, wherein the organic functional layer generally comprises the following components: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Electrons and holes are respectively injected into a cathode and an anode under the action of an externally applied electric field, the electrons and the holes are respectively injected into a HOMO energy level of an electron transport layer and a LUMO energy level of a hole transport layer, the electrons at the HOMO energy level and the holes at the LUMO energy level continuously migrate to a light emitting layer due to the existence of extremely poor energy, so that a 'hole-electron' pair is formed, the 'hole-electron' pair is an exciton formed by recombination, the exciton with higher energy freely migrates in the light emitting layer and is accompanied by free transition, the energy of generated photons is determined according to the size of the exciton, and the color of generated light is generated.
OLEDs, one of the most promising photovoltaic technologies in the 21 st century, have been developed in both display and lighting areas. However, there are many problems in light emitting performance and manufacturing technology thereof, and further investigation is required. The light-emitting material is an indispensable factor for determining the light-emitting efficiency of OLEDs, wherein the light-emitting material can be divided into a host material and a dopant material according to its function, and it is important to obtain an effective host material in order to obtain higher electroluminescent efficiency. Therefore, the triplet energy level of a host material having excellent properties should be higher than that of a guest material, and at the same time, the transport of electrons and holes in the host material should be balanced effectively, but it is far from easy to balance the above factors in one molecule. Therefore, it is urgent to develop a light-emitting host material with excellent performance, and to effectively improve the light-emitting efficiency, driving voltage and service life of OLEDs.
The organic electron transport material refers to an organic semiconductor material which can control electron orientation and order migration under the action of an electric field so as to realize electron transport, but has the advantages of higher difficulty in preparation and characterization, lower mobility and poor stability, and seriously influences the development of organic photoelectric materials and devices. Therefore, it is important to develop an electron transport material with higher mobility, proper triplet energy level and better thermal and chemical stability.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a compound containing a nitrogen-containing condensed aromatic ring and an organic electroluminescent device thereof, which can effectively improve the luminous efficiency, the driving voltage and the service life of OLEDs.
Specifically, the invention provides a compound containing a nitrogen-containing condensed aromatic ring, which is represented by the following formula I:
the Ar is as follows 1 A group represented by formula II, wherein the ring A is selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C2-C60 heteroaryl group;
said X is selected from O, S, C (R) x ) 2 Or N (R) a )；
Each T is independently selected from CH or N; t fused to ring A is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is x Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
The R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkylAny one of substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C2-C60, fused ring groups of substituted or unsubstituted alicyclic ring of C3-C30 and aromatic ring of C6-C60, fused ring groups of substituted or unsubstituted alicyclic ring of C3-C30 and heteroaromatic ring of C2-C60, or a combination thereof;
said n 1 Selected from 0, 1 or 2; said n 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
the Z is 1 ～Z 6 Each independently selected from C (R) y ) Or N, Z 1 ～Z 6 At least one of which is selected from N, and Z 1 ～Z 6 Up to three of which are selected from N;
the R is y Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
the Ar is as follows 2 、Ar 3 At least one of the groups shown in 1-a or 1-b, and the rest is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C6-C60 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C2-C60 heteroaromatic rings;
said Y is independently selected from O, S, C (R c R d ) Or N (R) b )；
The R is c 、R d Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-ultrahigh Any one of aryl group of C30, substituted or unsubstituted heteroaryl group of C2 to C30, fused ring group of substituted or unsubstituted alicyclic ring of C3 to C30 and aromatic ring of C6 to C30, fused ring group of substituted or unsubstituted alicyclic ring of C3 to C30 and heteroaromatic ring of C2 to C30, or R c 、R d Are connected with each other to form a substituted or unsubstituted ring;
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7;
the L is 1 ～L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group of C6 to C60, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60, or a combination thereof.
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 the nitrogen-containing condensed aromatic ring compounds.
Advantageous effects
The nitrogen-containing condensed aromatic ring compound shown in the formula I has higher decomposition temperature, higher vitrification conversion temperature, good film forming property and higher triplet state energy level, can effectively ensure the stability and high efficiency of the device, effectively prevent the energy back transmission from the guest material to the host material, and can obviously improve the luminous efficiency and the service life of the device when being used as the host material of the luminous layer in the organic electroluminescent device; in addition, the compound has higher electrophilicity, proper HOMO and LUMO energy levels and better hole blocking capability, so as to ensure that the compound is matched with the work function of a cathode, reduce the energy barrier of the cathode and a luminescent layer, and effectively block holes in the luminescent layer from escaping to an electron transport layer, so that electrons and holes in the luminescent layer are efficiently compounded, and the luminous efficiency of the organic electroluminescent device is improved.
In conclusion, when the nitrogen-containing condensed aromatic ring compound provided by the invention is applied to an OLED device, the luminous efficiency and the service life of the device can be effectively improved, and the nitrogen-containing condensed aromatic ring compound is an OLED material with very excellent performance.
Detailed Description
In the following, a technical solution with embodiments of the present invention will be further clarified and fully elucidated, and it will be apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.
In the present description of the invention,meaning a moiety attached to another substituent. />May be attached at any optional position of the attached group/fragment.
In the present specification, when a bond at a substituent or a linking site penetrates two or more rings, it means that it may be linked to the two or more ringsIn particular, may be linked to any of the corresponding selectable positions of the loop. For example, the number of the cells to be processed,can indicate->Or->Can indicate->And so on.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring. For example, the number of the cells to be processed, Can indicate->Can indicate-> Can indicate-> And so on.
Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.
The alkyl group according to the present invention means a generic term for monovalent groups remaining after removal of one hydrogen atom in an alkane molecule, and may be a straight-chain alkyl group, a branched alkyl group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 15 carbon atoms, still more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms, including but not limited to methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc.; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably, but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc.
As used herein, "substituted or unsubstituted silyl" refers to-Si (R n ) 3 A group wherein each R n Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R n Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, particularly preferably 1 to 8 carbon atoms. The cycloalkyl radicals preferably have 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 3 to 10 carbon atoms, particularly preferably 3 to 7 carbon atoms. Preferably, each R n Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl Substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.
The cycloalkyl refers to the general term that monovalent groups are remained after one hydrogen atom is removed from a cyclic alkane molecule, and the cycloalkyl can be monocyclic cycloalkyl, polycyclic cycloalkyl or bridged cycloalkyl. Preferably from 3 to 20 carbon atoms, more preferably from 3 to 18 carbon atoms, even more preferably from 3 to 12 carbon atoms, particularly preferably from 3 to 6 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphene, fenchyl, isobornyl, and the like.
The aryl refers to the general term that monovalent groups are left after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic compound molecule, and the aryl can be monocyclic aryl, polycyclic aryl or condensed ring aryl. Preferably from 6 to 60 carbon atoms, more preferably from 6 to 30 carbon atoms, even more preferably from 6 to 18 carbon atoms, particularly preferably from 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetrabiphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, and the like, but are not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, and specific examples may include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirofluorenyl, spirobifluorenyl, and the like.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably having 2 to 30 carbon atoms, more preferably having 2 to 18 carbon atoms, and particularly preferably having 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused ring heteroaryl group may include, but are not limited to, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorene oxaanthracenyl, spirofluorene thianthrenyl, and the like.
The arylene group according to the present invention is a generic term for divalent radicals remaining after removal of two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 60 carbon atoms, more preferably having 6 to 30 carbon atoms, even more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; specific examples may include, but are not limited to, naphthylene, anthrylene, phenanthrylene, pyreylene, triphenylene, fluoranthenylene, and the like.
By heteroarylene is meant that at least one carbon atom in the arylene group is replaced with a heteroatom, which includes but is not limited to oxygen, sulfur, nitrogen, or phosphorus atoms, leaving the generic term for divalent radicals. Preferably from 2 to 60 carbon atoms, more preferably from 2 to 30 carbon atoms, even more preferably from 2 to 18 carbon atoms, particularly preferably from 2 to 12 carbon atoms. The attachment site of the heteroarylene group may be on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. Specific examples of the monocyclic and condensed ring heteroarylene groups may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, a carbazolylene group, a benzofuranylene group, a benzothienyl group, a benzocarbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzocarbazolylene group, and the like; specific examples of the polycyclic heteroarylene group may include bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but are not limited thereto.
The fused ring group of the alicyclic ring and the aromatic ring refers to the general term that after the alicyclic ring and the aromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 6 to 60 carbon atoms, more preferably having 6 to 30 carbon atoms, still more preferably having 6 to 18 carbon atoms, and particularly preferably having 6 to 12 carbon atoms, and the fused ring group of the alicyclic and aromatic rings may include, but is not limited to, benzocyclopropane group, benzocyclobutane group, benzocyclobutene group, indanyl group, indenyl group, tetrahydronaphthyl group, dihydronaphthyl group, benzocycloheptane group, benzocycloheptenyl group, and the like.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the sum of monovalent groups obtained by removing one hydrogen atom after the alicyclic ring and the heteroaromatic ring are fused together. Preferably from 5 to 30 carbon atoms, more preferably from 5 to 18 carbon atoms, particularly preferably from 5 to 12 carbon atoms. The fused cyclic group of the alicyclic and heteroaromatic ring may include, but is not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidbenzocycloheptyl, dibenzofuran-cyclopropyl, dibenzofuran-cyclobutyl, dibenzofuran-cyclopentyl, dibenzofuran-cyclohexyl, dibenzofuran-cycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-cyclobutyl, dibenzothiophene-cyclopentyl, dibenzothiophene-cyclohexyl, dibenzothiophene-cycloheptyl, carbazole-cyclopropyl, carbazole-cyclobutyl, carbazole-cyclopentyl, carbazole-cyclohexyl, carbazole-cycloheptyl, and the like.
The term "fused ring-sub-group" as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring to an aromatic ring and then removing two hydrogen atoms. Preferably having 6 to 30 carbon atoms, more preferably having 6 to 25 carbon atoms, still more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 12 carbon atoms, and the fused-back ring group of the alicyclic ring and the aromatic ring may include, but is not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.
The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic term of bivalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing two hydrogen atoms. Preferably having 3 to 30 carbon atoms, more preferably having 3 to 20 carbon atoms, still more preferably having 3 to 18 carbon atoms, particularly preferably having 3 to 12 carbon atoms, and the fused-back ring group of the alicyclic ring and the heteroaromatic ring may include a pyrido-cyclopropyl group, a pyrido-cyclobutyl group, a pyrido-cyclopentyl group, a pyrido-cyclohexyl group, a pyrido-benzoheptyl group, a pyrimido-cyclopropyl group, a pyrimido-cyclobutyl group, a pyrimido-cyclopentyl group, a pyrimido-cyclohexyl group, a pyrimido-benzocycloheptyl group, a dibenzofuran-cyclopropyl group, a dibenzofuran-cyclobutyl group, a dibenzofuran-cyclopentyl group, a dibenzofuran-cyclohexyl group, a dibenzofuran-cycloheptyl group, a dibenzothiophene-cyclopropyl group, a dibenzothiophene-cyclopentyl group, a dibenzothiophene-cyclohexyl group, a dibenzothiophene-cycloheptyl group, a carbazole-cyclopropyl group, a carbazole-benzocarbazole-cyclobutyl group, a carbazole-cyclopentyl group, a carbazolo-cyclohexyl group, a carbazolo-cycloheptyl group, and the like, but is not limited thereto.
The term "substituted … …" as used herein, such as "substituted alkyl group, substituted cycloalkyl group, substituted aryl group, substituted heteroaryl group, substituted alicyclic ring and condensed ring group of aromatic ring, substituted arylene group, substituted heteroarylene group, alicyclic ring and condensed ring group of aromatic ring" means independently mono-or poly-substituted with: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and the like, but are not limited thereto, or two adjacent substituents may be linked to form a ring. Preferably mono-or polysubstituted by: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, perylenyl, pyrenyl, benzyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, phenothiazinyl, phenoxazinyl, indolyl, and the like, but are not limited thereto.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be a three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, condensed ring or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole or the like, but is not limited thereto.
The invention provides a compound containing a nitrogen-containing condensed aromatic ring, which has a structure shown in a formula I:
the Ar is as follows 1 A group represented by formula II, wherein the ring A is selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C2-C60 heteroaryl group;
said X is selected from O, S, C (R) x ) 2 Or N (R) a )；
Each T is independently selected from CH or N; t fused to ring A is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is x Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstitutedAny one of an alkyl group of C1 to C30, a cycloalkyl group of substituted or unsubstituted C3 to C30, an aryl group of substituted or unsubstituted C6 to C30, a heteroaryl group of substituted or unsubstituted C2 to C30, a fused ring group of an alicyclic ring of substituted or unsubstituted C3 to C30 and an aromatic ring of C6 to C30, and a fused ring group of an alicyclic ring of substituted or unsubstituted C3 to C30 and a heteroaromatic ring of C2 to C30;
the R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said n 1 Selected from 0, 1 or 2; said n 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
the Z is 1 ～Z 6 Each independently selected from C (R) y ) Or N, Z 1 ～Z 6 At least one of which is selected from N, and Z 1 ～Z 6 Up to three of which are selected from N;
the R is y Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ringAny one of a group, a substituted or unsubstituted C3-C30 alicyclic ring and a condensed cyclic group of a C2-C30 heteroaromatic ring;
the Ar is as follows 2 、Ar 3 At least one of the groups shown in 1-a or 1-b, and the rest is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C6-C60 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C2-C60 heteroaromatic rings;
said Y is independently selected from O, S, C (R c R d ) Or N (R) b )；
The R is c 、R d Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R c 、R d Are connected with each other to form a substituted or unsubstituted ring;
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is 3 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstitutedAny one or a combination of aryl of C6-C60, heteroaryl of substituted or unsubstituted C2-C60, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and aromatic ring of C6-C60, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and heteroaromatic ring of C2-C60, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7;
the L is 1 ～L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group of C6 to C60, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60, or a combination thereof.
Preferably, the compound containing a nitrogen-containing condensed aromatic ring is selected from at least one of the formulas I-1 to I-13:
still more preferably, the nitrogen-containing condensed aromatic ring-containing compound is selected from at least one of the formulas II-1 to II-14:
preferably, the Ar 1 Or a group represented by formula II is selected from any one of the following groups:
said X is selected from O, S, C (R) x ) 2 Or N (R) a )；
The T is selected from CH or N;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is x Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
the R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring Any one or a combination of a condensed ring group of a group, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring;
said n 1 Selected from 0, 1 or 2; said n 4 Selected from 0, 1, 2, 3, 4, 5 or 6; said n 5 Selected from 0, 1, 2, 3 or 4; said n 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
Still preferably, the Ar 1 Or a group represented by formula II is selected from any one of the following groups:
/>
the R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said n 1 Selected from 0, 1 or 2; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said n 4 Selected from 0, 1, 2, 3, 4, 5 or6, preparing a base material; said n 5 Selected from 0, 1, 2, 3 or 4; said n 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n 7 Selected from 0, 1, 2 or 3; said n 9 Selected from 0, 1, 2, 3, 4 or 5; said n 10 Selected from 0 or 1.
Further preferably, the Ar 1 Or a group represented by formula II is selected from any one of the following groups:
/>
the R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said n 1 Selected from 0, 1 or 2; said n 5 Selected from 0, 1, 2, 3 or 4; said n 7 Selected from 0, 1, 2 or 3; said n 10 Selected from 0 or 1.
Preferably, said R 1 Independently selected from hydrogen, deuterium, and cyanoA group, a nitro group, a halogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-tert-butylsilyl group, a dimethylethylsilyl group, a triphenylsilyl group, a cyclopropanyl group, a cyclobutyl group, a cyclopentylalkyl group, a cyclohexenyl group, an adamantyl group, a norbornyl group, a phenyl group, a biphenyl group, a terphenyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a benzocyclopentenyl group, a benzocyclohexenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a o-royl group, a 9, 9-dimethylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-tert-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphthyl, deutero-anthryl, deutero-phenanthryl, deutero-triphenylenyl, deutero-pyridyl, deutero-pyrimidinyl, deutero-quinolinyl, deutero-isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl Methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphtyl-substituted phenyl, triphenylsulfanyl-substituted phenyl, phenylquinoline, benzoquinoline, or substituted phenyl, benzoquinoline, or substituted phenyl.
Preferably, said R 2 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, tri-cyclopropenylPhenylene, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, benzofuranyl deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylenyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted biphenyl, ethyl substituted naphthyl, isopropyl substituted phenyl, isopropyl substituted biphenyl, isopropyl substituted naphthyl, t-butyl substituted adamantyl, t-butyl substituted phenyl, t-butyl substituted biphenyl, t-butyl substituted naphthyl, t-butyl substituted phenanthryl, t-butyl substituted 9, 9-dimethylfluorenyl, t-butyl substituted 9, 9-diphenylfluorenyl, t-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, triphenylsilyl substituted phenyl, trimethylsilyl substituted naphthyl, adamantyl substituted phenyl Any one of adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroiisopropyl-substituted phenyl, deuteroiisopropyl-substituted biphenyl, deuteroit-butyl-substituted phenyl, deuteroit-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, the Ar 2 、Ar 3 Is selected from one of the following groups represented by formulae 1-a, 1-b:
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the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is c 、R d Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic, and C6-C30 aromatic ringA condensed cyclic group, any one of a substituted or unsubstituted C3-C30 alicyclic ring and a condensed cyclic group of a C2-C30 heteroaromatic ring, or R c 、R d Are connected with each other to form a substituted or unsubstituted ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said n 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said n 4 Selected from 0, 1, 2, 3, 4, 5 or 6; said n 5 Selected from 0, 1, 2, 3 or 4; said n 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n 7 Selected from 0, 1, 2 or 3; said n 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 9 Selected from 0, 1, 2, 3, 4 or 5; said n 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
Preferably, said R b Selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentanyl, cyclohexenyl, cycloheptanyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylyl, pyridyl, pyrimidinyl, pyridazinyl,Pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthryl, deuterated phenanthrenyl, thiazolyl, and deuterated isofluorenyl deuterated triphenylene, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornane Any one of phenyl substituted with a group, biphenyl substituted with norbornyl, phenyl substituted with deuterated methyl, biphenyl substituted with deuterated methyl, phenyl substituted with deuterated isopropyl, biphenyl substituted with deuterated isopropyl, phenyl substituted with deuterated tert-butyl, biphenyl substituted with deuterated tert-butyl, phenyl substituted with naphthyl, phenyl substituted with phenanthryl, phenyl substituted with triphenylene, phenyl substituted with benzofuran, phenyl substituted with benzothiophene, phenyl substituted with pyridine, phenyl substituted with pyrimidine, phenyl substituted with quinoline, phenyl substituted with isoquinoline, phenyl substituted with quinazoline, phenyl substituted with quinoxaline, phenyl substituted with benzoxazole, phenyl substituted with benzothiazole, phenyl substituted with benzimidazole.
Preferably, R is c 、R d Each independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, benzocyclobutenyl pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthrolinyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated isopropyl Adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylyl, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzene Any one of the phenyl groups substituted with the imidazole.
Preferably, said R 3 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzocyclobutenyl, benzopyrazinyl, and combinations thereof naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthryl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-extraction Substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilane-substituted phenyl, triethylsilane-substituted phenyl, triphenylsilane-substituted phenyl, trimethylsilane-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, tert-substituted phenyl, deuterated phenyl-substituted benzoquinoline, tert-butyl-substituted phenyl, benzoquinoline, phenylquinoline, or substituted benzoquinoline, or substituted phenyl, or substituted benzoquinoline.
Preferably, the Ar 2 、Ar 3 And when not of the formulae 1-a and 1-b, one or a combination of the following groups are selected:
wherein each r is independently selected from CH or N;
the M is 1 ～M 4 Each independently selected from O, S, C (R) j R k )、N(R z )、Si(R m ) 2 Any one of them;
the R is j 、R k Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R j 、R k Form a substituted or unsubstituted ring;
the R is z Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is m Any one selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
the R is h Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is 4 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30, a substituted or unsubstituted cycloalkyl of C3-C30, a substituted or unsubstituted aryl of C6-C60, a substituted or unsubstituted heteroaryl of C2-C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and an aromatic ring of C6-C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and a heteroaromatic ring of C2-C60, or a combination thereof, or two adjacent R' s 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is 5 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
said n 1 Selected from 0, 1 or 2; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said n 5 Selected from 0, 1, 2, 3 or 4; said n 7 Selected from 0, 1, 2 or 3; said n 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 9 Selected from 0, 1, 2, 3, 4 or 5.
Still preferably, the Ar 2 、Ar 3 And when not of the formulae 1-a and 1-b, one or a combination of the following groups are selected:
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the R is f 、R g Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted Or any one of an unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring;
the R is h Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring;
the R is i Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is 4 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is 5 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substitutedOr any one or combination of unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C6-C60 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C2-C60 heteroaromatic rings, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
The k is 1 Selected from 0, 1, 2, 3, 4 or 5; the k is 2 Selected from 0, 1, 2, 3 or 4; the k is 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the k is 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the k is 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k is 6 Selected from 0, 1 or 2; the k is 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the k is 8 Selected from 0, 1, 2 or 3; the k is 9 Selected from 0, 1, 2, 3, 4, 5 or 6; the k is 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Preferably, said R 4 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutanyl, and mixtures thereof benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl Thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deuteroisopropyl, deutero-n-butyl, deuteroisobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroisopropyl-substituted phenyl, deuteroisopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylyl-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl Phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, said R 5 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzocyclobutenyl, benzopyrazinyl, and combinations thereof naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthryl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoro Methyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, triphenylsilyl substituted phenyl, trimethylsilyl substituted naphthyl, adamantyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated isopropyl substituted phenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, triphenylsubstituted phenyl, benzofuran substituted phenyl, benzothiophene substituted phenyl, pyridine substituted phenyl, pyrimidine substituted phenyl, quinoline substituted phenyl, isoquinoline substituted phenyl, any one of quinazoline substituted phenyl, quinoxaline substituted phenyl, benzoxazole substituted phenyl, benzothiazole substituted phenyl, benzimidazole substituted phenyl.
Preferably, the L 1 ～L 3 Each independently selected from a single bond or one or a combination of the groups shown below:
wherein each p is independently selected from CH or N;
the M is 5 ～M 7 Each independently selected from O, S, C (R) p R q )、N(R r ) Any one of them;
the R is p 、R q Each independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring with a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring with a C2-C30 heteroaromatic ring, or R p 、R q Form a substituted or unsubstituted ring;
the R is r Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
The R is n Each independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is 6 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstitutedAny one or a combination of a condensed ring group of an alicyclic ring of C3-C30 and an aromatic ring of C6-C60, a condensed ring group of a substituted or unsubstituted alicyclic ring of C3-C30 and a heteroaromatic ring of C2-C60;
said b 0 Selected from 0, 1 or 2; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
Still preferably, the L 1 ～L 3 Each independently selected from a single bond or one or a combination of the groups shown below:
the R is s Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is t Any one of a cycloalkyl group of a substituted or unsubstituted C3 to C30, an aryl group of a substituted or unsubstituted C6 to C60, a heteroaryl group of a substituted or unsubstituted C2 to C60, a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and an aromatic ring of a C6 to C60, and a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and a heteroaromatic ring of a C2 to C60;
the R is v Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted Any one of a condensed ring group of a substituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a condensed ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is 7 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the c 0 Selected from 0, 1 or 2; c 1 Selected from 0, 1, 2, 3 or 4; the c 2 Selected from 0, 1, 2, 3, 4, 5 or 6; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c 5 Selected from 0, 1, 2 or 3; the c 6 Selected from 0 or 1; the c 7 Selected from 0, 1, 2, 3, 4 or 5; the c 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
Preferably, said R 7 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthrenyl, 9-dimethylfluorenyl, 9-diphenyl Fluorenyl, 9' -spirobifluorenyl, benzo9, 9' -dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphtalenyl, deuterated anthryl, deuterated phenanthrenyl, deuterated triphenylenyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated pyrinyl deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteromethyl-substituted isopropyl Any one of substituted phenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, triphenylene substituted phenyl, benzofuran substituted phenyl, benzothiophene substituted phenyl, pyridine substituted phenyl, pyrimidine substituted phenyl, quinoline substituted phenyl, isoquinoline substituted phenyl, quinazoline substituted phenyl, quinoxaline substituted phenyl, benzoxazole substituted phenyl, benzothiazole substituted phenyl, benzimidazole substituted phenyl.
Most preferably, the nitrogen-containing condensed aromatic ring-containing compound is selected from at least one of the structures shown below:
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the specific structural forms of the nitrogen-containing condensed aromatic ring compound represented by the formula I according to the present invention are listed above, but the present invention is not limited to the listed chemical structures, and substituents are included as defined above, even when the structure represented by the formula I is based.
The invention also provides an organic electroluminescent device which comprises at least one of the nitrogen-containing condensed aromatic ring compounds.
Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer comprises at least one of the nitrogen-containing condensed aromatic ring compounds.
Still preferably, the organic electroluminescent device according to the present invention may include one or more organic layers, the organic layers may include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, a hole blocking layer, an electron blocking layer, a capping layer, and the like, and specifically, the organic layers between the anode and the cathode may include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, a hole blocking layer, an electron blocking layer, and the like, and the organic layers outside one or more of the anode and the cathode may include a capping layer, and the like. The organic layer may be formed of a single-layer structure or a multilayer structure in which the above organic layers are stacked; meanwhile, each organic layer may further include one or more layers, for example, the hole transport layer includes a first hole transport layer and a second hole transport layer. However, the structure of the organic electroluminescent device is not limited thereto, and may include fewer or more organic layers.
Further preferably, the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and at least one of the electron transport layer or the hole blocking layer comprises at least one of the nitrogen-containing condensed aromatic ring-containing compounds according to the present invention.
More preferably, the organic layer is located between the anode and the cathode, the organic layer comprising an electron transport layer comprising at least one of the nitrogen-containing condensed aromatic ring-containing compounds of the present invention.
More preferably, the organic layer is located between the anode and the cathode, the organic layer comprising a hole blocking layer comprising at least one of the nitrogen-containing condensed aromatic ring-containing compounds of the present invention.
Most preferably, the organic layer is located between the anode and the cathode, the organic layer comprising a light-emitting layer comprising at least one of the nitrogen-containing condensed aromatic ring-containing compounds of the present invention.
As the anode of the present invention, a material having a high work function is preferable. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2 ) Zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single layerThe structure or a multilayer structure including two or more layers, for example, the anode may have a single layer structure of Al or a three-layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
As the hole injection layer of the present invention, a material having a good hole accepting ability is preferable. Specific examples include metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrenes, quinacridones, perylenes, etc., and examples include 4,4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazabenzophenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyandimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), etc., but are not limited thereto. It may be a single structure composed of a single substance, or may be a single-layer or multi-layer structure formed of different substances.
As the hole transport layer of the present invention, a material having high hole mobility is preferable. Specific examples thereof include materials such as diphenylamines, fluorenes, carbazoles, biphenyldiamines, etc., and examples thereof include N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4'4 "-tris (N, N-diphenylamino) triphenylamine (TDATA), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4',4" -tris (carbazol-9-yl) triphenylamine (TCTA), etc., but are not limited thereto.
As the light-emitting layer material of the present invention, in addition to the nitrogen-containing condensed aromatic ring compound of the present invention, a red, green or blue light-emitting material may be used, and generally comprises a guest (doped) material and a host material, wherein the guest material may be a simple fluorescent material or phosphorescent material, or may be a combination of fluorescent and phosphorescent materials. Examples of the host material of the light-emitting layer include, but are not limited to, distyrylaryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, and the like, 9' -diphenyl-9H, 9' H-3,3' -bicarbazole, 9- (5- (3- (9H-carbazol-9-yl) phenyl) pyridin-3-yl) -9H-carbazole (CPPyC), 5, 7-diphenyl-5, 7-indolino [2,3-b ] carbazole, 4' -bis (carbazol-9-yl) -2,2' -dimethylbiphenyl (CDBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), and 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene (TBADN), while the host material is required to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material.
The guest material may be selected from any one or more of the following structures: examples of the metal complex (for example, iridium complex, platinum complex, osmium complex, rhodium complex, etc.), anthracene derivative, pyrene derivative, perylene derivative, etc. include bis (2- (naphthalen-2-yl) pyridine) (acetylacetonate) iridium (Ir (npy) 2 acac), iridium acetylacetonato bis (2-phenylpyridine) (Ir (ppy) 2 (acac)), tris [2- (3-methyl-2-pyridinyl) phenyl ]]Iridium (Ir (3 mppy) 3 ) Bis (2-benzo [ H)]quinoline-C2, N') (acetylacetonato) iridium (Ir (bzq) 2 (acac)), bis (1-phenyl-isoquinoline) (acetylacetonate) iridium (Ir (piq) 2 (acac)), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) 4,4' -bis (9-ethyl-3-carbazolyl vinyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl ]]Biphenyl (DPAVBi), etc., but is not limited thereto.
As the electron transport layer material of the present invention, in addition to the nitrogen-containing condensed aromatic ring-containing compound of the present invention, a material having high electron mobility is preferable, and may be selected from any one or more of the following structures: the metal chelate compound, the oxaoxazole derivative, the thiazole derivative, the diazole derivative, the azabenzene derivative, the diazene derivative, the silicon-containing heterocyclic compound, the boron-containing heterocyclic compound, the cyano compound, the quinoline derivative, the phenanthroline derivative, the benzimidazole derivative, and the like are not limited thereto, and may be a single structure composed of a single substance, a single layer structure or a multilayer structure composed of different substances.
As the hole blocking layer material of the present invention, in addition to the nitrogen-containing condensed aromatic ring-containing compound of the present invention, a material capable of effectively blocking holes is preferable, and may be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, and the like, but are not limited thereto.
As the electron injection layer material of the present invention, a material having a low work function is preferable, and may be selected from any one or several of the following structures: a metal, an alkali metal, an alkaline earth metal, an alkali metal halide, an alkaline earth metal halide, an alkali metal oxide, an alkaline earth metal oxide, an alkali metal salt, an alkaline earth metal salt, a metal complex, or other substances having high electron injection properties. Examples can be cited as Li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, and the like, but is not limited thereto.
As the cathode of the present invention, a material having a low work function is preferable, and the cathode may be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.
As the coating material of the present invention, a material having an optical coupling effect is preferable. Specific examples may include: examples of the metal halide, metal oxide, metal nitride, aromatic amine derivative, carbazole derivative, oxazole derivative and the like include LiF, csF, mgF 2 、CaF 2 、CsCl、CuI、V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、Alq 3 But is not limited thereto.
The organic layers, the cathode, the anode and the cover layer can be prepared by any one method of vacuum evaporation, ink-jet printing, sputtering, plasma, spin coating, dipping and screen printing, and the thickness of each layer is not particularly limited, so that good device performance can be obtained. Each of the organic layers described above is preferably prepared using a method of vacuum evaporation, inkjet printing, or spin coating, but is not limited thereto.
The organic electroluminescent device provided by the invention can be applied to the fields of illumination, display and the like, and can be specifically exemplified as the fields of illumination light sources, smart phone display screens, tablet personal computer display screens, tablet television display screens, VR, smart watches, wearable devices and vehicle-mounted systems.
Preparation and characterization of the Compounds
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;
the following is one preparation method of the compound represented by the formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compounds of formula I may be prepared by the reaction schemes shown below, using conventional methods well known to those skilled in the art. The main reaction type involved in the invention is Suzuki coupling reaction and Miyaura boric acid esterification reaction.
Synthetic route
Preparation of the compound of formula I:
the X is a ～X c Each is independently selected from any one of I, br and Cl; the Z is 1 ～Z 6 、Ar 1 ～Ar 3 、L 1 ～L 3 The definition of (2) is the same as the definition described above.
Synthesis example 1: preparation of intermediate A-4
A-4 (53.26 g,195.00 mmol), b-4 (36.88 g,200.00 mmol), sodium carbonate (31.80 g,300.00 mmol), 780mL toluene/ethanol/water (volume ratio 2:1:1) mixed solvent are added into a reaction bottle, after air is replaced by nitrogen for three times, tetrakis (triphenylphosphine) palladium (2.31 g,2.00 mmol) is added into the reaction bottle, stirring reaction is carried out for 5.5 hours under the protection of nitrogen, after the reaction is finished, the reaction mixture is cooled to room temperature, suction filtered, washed by distilled water, and then the obtained solid is recrystallized by toluene to obtain an intermediate c-4 (53.86 g, yield 83%); the purity of the solid detected by HPLC is more than or equal to 99.69 percent.
To the reaction flask were added c-4 (49.92 g,150.00 mmol), (methoxymethyl) triphenylphosphine chloride (77.13 g,225.00 mmol) and 750mL tetrahydrofuran, the mixture was stirred, then cooled to below 0℃potassium tert-butoxide (1M in THF, 375 mL) was slowly added dropwise to the mixture, after the dropwise addition was completed, the temperature of the mixture was slowly raised, and the mixture was stirred at room temperature for 6.5 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, and carrying out suction filtration, and recrystallizing the obtained solid with toluene/methanol (volume ratio of 8:1) to obtain an intermediate d-4 (43.30 g, yield 80%); the purity of the solid detected by HPLC is more than or equal to 99.76 percent.
D-4 (37.89 g,105.00 mmol), 175mL of Eton's reagent (methanesulfonic acid solution of phosphorus pentoxide with a composition of 7.7 wt%) and 275mL of chlorobenzene were added to the reaction flask, the mixture was cooled to room temperature after the reaction was completed, distilled water was then added to the mixture, extracted with methylene chloride, the organic phase was dried over anhydrous magnesium sulfate, filtered, the solvent was concentrated by distillation under reduced pressure, cooled and crystallized, suction filtration was performed, and then recrystallization was performed with toluene to obtain intermediate e-4 (27.96 g, yield 81%); the purity of the solid detected by HPLC is more than or equal to 99.83 percent.
E-4 (24.66 g,75.00 mmol) was added to the flask,Dipinacol diboronate (20.32 g,80.00 mmol), potassium acetate (14.72 g,150.00 mmol) and DMF (400 mL) were added to the reaction flask, after three times the air was replaced with nitrogen, pd (dppf) Cl was added to the reaction flask 2 (0.59 g,0.80 mmol), heating and stirring for reaction for 8 hours, cooling to room temperature after the reaction is finished, adding distilled water into the mixture, extracting the mixture with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, concentrating the solvent by reduced pressure distillation, cooling and crystallizing the mixture, filtering the mixture by suction, and recrystallizing the mixture with toluene to obtain an intermediate A-4 (27.11 g, yield 86%); HPLC purity is more than or equal to 99.88%. Mass spectrum m/z:420.1885 (theory: 420.1897).
According to the preparation method, the invention also synthesizes the following intermediates:
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synthesis example 2: preparation of intermediate D-39
Synthesis of intermediate M-39:
a-39 (25.22 g,60.00 mmol), n-39 (11.49 g,60.00 mmol), sodium carbonate (11.45 g,108.00 mmol), and 240mL of toluene/ethanol/water (2:1:1) mixed solvent were added to the reaction flask, and after air was replaced with nitrogen three times, tetrakis (triphenylphosphine) palladium (0.69 g,0.60 mmol) was added to the reaction flask and reacted under reflux for 7 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 recrystallisation to give intermediate M-39 (20.16 g, 83% yield); HPLC purity is more than or equal to 99.78%. Mass spectrum m/z:404.0979 (theory: 404.0968).
Synthesis of intermediate D-39:
under the protection of nitrogen, M-39 (18.22 g,45.00 mmol), pinacol diboronate (12.70 g,50.00 mmol), potassium acetate (8.83 g,90.00 mmol) and DMF (240 mL) were added to the reaction flask, after three times of nitrogen substitution of air, pd (dppf) Cl was added to the reaction flask 2 (0.37 g,0.50 mmol), heating and stirring for 7.5 hours, cooling to room temperature after the reaction, adding distilled water, extracting with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, distilling and concentrating the solvent under reduced pressure, cooling and crystallizing, filtering, and recrystallizing with toluene to obtain an intermediate D-39 (17.87 g, yield 80%); HPLC purity is more than or equal to 99.85%. Mass spectrum m/z:496.2198 (theory: 496.2210).
According to the preparation method, the invention also synthesizes the following intermediates:
synthesis example 3: preparation of intermediate F-48
Synthesis of intermediate E-48:
to the reaction flask, h-39 (17.65 g,60.00 mmol), b' -48 (11.73 g,60.00 mmol), sodium carbonate (11.45 g,108.00 mmol) and 240mL of toluene/ethanol/water (2:1:1) mixed solvent were added, and after air was replaced with nitrogen three times, tetrakis (triphenylphosphine) palladium (0.69 g,0.60 mmol) was added to the reaction flask and reacted under reflux for 6.5 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 recrystallisation to give intermediate E-48 (13.74 g, 81% yield); HPLC purity is more than or equal to 99.78%. Mass spectrum m/z:282.0735 (theory: 282.0749).
Synthesis of intermediate F-48:
e-48 was added to the reaction flask under nitrogen protection(12.72 g,45.00 mmol), pinacol diboronate (12.70 g,50.00 mmol), potassium acetate (8.83 g,90.00 mmol) and DMF (240 mL) were added to the reaction flask, after three times the air was replaced with nitrogen, pd (dppf) Cl was added to the reaction flask 2 (0.37 g,0.50 mmol), heating and stirring for 7 hours, cooling to room temperature after the reaction, adding distilled water, extracting with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, distilling and concentrating the solvent under reduced pressure, cooling and crystallizing, filtering, and recrystallizing with toluene to obtain an intermediate F-48 (13.98 g, yield 83%); HPLC purity is more than or equal to 99.88%. Mass spectrum m/z:374.1979 (theory: 374.1991).
According to the preparation method, the invention also synthesizes the following intermediates:
synthesis example 4: preparation of Compound 4
Synthesis of intermediate B-4:
to the reaction flask was added f-4 (12.91 g,70.00 mmol), g-4 (15.31 g,75.00 mmol), potassium acetate (13.74 g,140.00 mmol), pd (dppf) Cl under nitrogen 2 (0.51 g,0.70 mmol) and 340ml THF, under reflux for 5 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=10: 1 to give intermediate B-4 (12.50 g, yield 79%); the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z:224.9873 (theory: 224.9861).
Synthesis of intermediate C-4:
b-4 (11.30 g,50.00 mmol), h-4 (13.24 g,45.00 mmol), potassium acetate (9.81 g,100.00 mmol), pd (dppf) Cl were added to the flask under nitrogen 2 (0.37 g,0.50 mmol) and 270ml THF, and reacted under reflux for 6 hours. After the reaction is finished, cooling to room temperature, suction filtering to obtain filter cake, using toluene/ethyl acetate to make the filter cakeAlcohol = 10:1 to give intermediate C-4 (14.31 g, yield 80%); HPLC purity is more than or equal to 99.86%. Mass spectrum m/z:357.0682 (theory: 357.0669).
Synthesis of Compound 4:
to the reaction flask was added C-4 (12.52 g,35.00 mmol), A-4 (14.71 g,35.00 mmol), sodium carbonate (7.42 g,70.00 mmol), palladium acetate (0.08 g,0.35 mmol), P (t-Bu) under nitrogen 3 (0.20 g,0.70 mmol) and 115ml THF, and reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, extraction was performed with ethyl acetate, and the organic layer was dried over anhydrous MgSO 4 Drying, removal of solvent under reduced pressure, and recrystallization from toluene gave compound 4 (16.81, yield 78%); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:615.1958 (theory: 615.1947). Theoretical element content (%) C 43 H 25 N 3 O 2 : c,83.88; h,4.09; n,6.83. Measured element content (%): c,83.92; h,4.14; n,6.79.
Synthesis example 5: preparation of Compound 25
Synthesis of intermediate B-25:
in a reaction flask under nitrogen atmosphere f-25 (22.35 g,70.00 mmol), g-4 (15.31 g,75.00 mmol), potassium acetate (13.74 g,140.00 mmol), pd (dppf) Cl 2 (0.51 g,0.70 mmol) and 340ml THF, under reflux for 5.5 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 to give intermediate B-25 (15.28 g, yield 81%); HPLC purity is more than or equal to 99.85%. Mass spectrum m/z:267.9416 (theory: 267.9403).
Synthesis of intermediate C-25:
b-25 (13.48 g,50.00 mmol), h-25 (15.50 g,45.00 mmol), potassium acetate (9.81 g,100.00 mmol), pd (dppf) Cl were added to the flask under nitrogen 2 (0.37 g,0.50 mmol) and 250ml THF were reacted under reflux for 7 hours. After the reaction is finished, cooling to room temperature, and suction filtering to obtainFilter cake, filter cake with toluene/ethanol=5: 1 to give intermediate C-25 (16.68 g, yield 82%); the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z:406.0860 (theory: 406.0873).
Synthesis of Compound 25:
to the reaction flask was added C-25 (14.24 g,35.00 mmol), A-25 (17.37 g,35.00 mmol), sodium carbonate (7.42 g,70.00 mmol), palladium acetate (0.08 g,0.35 mmol), P (t-Bu) under nitrogen 3 (0.20 g,0.70 mmol) and 100ml THF, and reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, the mixture was extracted with methylene chloride, and the organic layer was dried over anhydrous MgSO 4 Drying, removal of the solvent under reduced pressure, and recrystallization from toluene gave compound 25 (19.97 g, yield 77%); HPLC purity is more than or equal to 99.91%. Mass spectrum m/z:740.2475 (theory: 740.2464). Theoretical element content (%) C 54 H 32 N 2 O 2 : c,87.55; h,4.35; n,3.78. Measured element content (%): c,87.50; h,4.39; n,3.81.
Synthesis example 6: preparation of Compound 39
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-39 and A-4 was replaced with equimolar D-39, to obtain Compound 39 (18.89 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:691.2273 (theory: 691.2260). Theoretical element content (%) C 49 H 29 N 3 O 2 : c,85.07; h,4.23; n,6.07. Measured element content (%): c,85.11; h,4.18; n,6.10.
Synthesis example 7: preparation of Compound 48
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar F-48 and A-4 was replaced with equimolar A-39, to obtainTo compound 48 (18.51 g), the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:695.2524 (theory: 695.2511). Theoretical element content (%) C 49 H 25 D 4 N 3 O 2 : c,84.58; h,4.78; n,6.04. Measured element content (%): c,84.63; h,4.82; n,6.01.
Synthesis example 8: preparation of Compound 74
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-74 to obtain Compound 74 (19.52 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:763.2643 (theory: 763.2655). Theoretical element content (%) C 52 H 37 N 3 O 2 Si: c,81.75; h,4.88; n,5.50. Measured element content (%): c,81.80; h,4.92; n,5.48.
Synthesis example 9: preparation of Compound 84
According to the same manner as that of Compound 25 in Synthesis example 5, F-25 was replaced with equimolar F-84, g-4 was replaced with equimolar g-84, h-25 was replaced with equimolar F-84, and A-25 was replaced with equimolar A-84, to obtain Compound 84 (19.79 g), and the purity of the solid was not less than 99.97% as measured by HPLC. Mass spectrum m/z:715.2248 (theory: 715.2260). Theoretical element content (%) C 51 H 29 N 3 O 2 : c,85.58; h,4.08; n,5.87. Measured element content (%): c,85.62; h,4.13; n,5.90.
Synthesis example 10: preparation of Compound 102
Compound 4 is identical according to Synthesis example 4The preparation method of (1) replaces g-4 with equimolar g-102, h-4 with equimolar h-39 and A-4 with equimolar A-102 to obtain compound 102 (18.99 g), and the purity of the solid detected by HPLC is more than or equal to 99.93%. Mass spectrum m/z:704.2226 (theory: 704.2212). Theoretical element content (%) C 49 H 28 N 4 O 2 : c,83.51; h,4.00; n,7.95. Measured element content (%): c,83.46; h,3.97; n,7.99.
Synthesis example 11: preparation of Compound 106
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-106, h-4 was replaced with equimolar h-39, and A-4 was replaced with equimolar A-39, to give Compound 106 (18.80 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:725.3055 (theory: 725.3042). Theoretical element content (%) C 51 H 39 N 3 O 2 : c,84.39; h,5.42; n,5.79. Measured element content (%): c,84.44; h,5.38; n,5.82.
Synthesis example 12: preparation of Compound 112
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-112 and A-4 was replaced with equimolar A-39, to obtain Compound 112 (18.91 g), and the purity of the solid was not less than 99.97% as measured by HPLC. Mass spectrum m/z:692.2201 (theory: 692.2212). Theoretical element content (%) C 48 H 28 N 4 O 2 : c,83.22; h,4.07; n,8.09. Measured element content (%): c,83.17; h,4.11; n,8.12.
Synthesis example 13: preparation of Compound 125
According to the same manner as that of Compound 4 in Synthesis example 4, g-4 was replaced with equimolar h-39, h-4 was replaced with equimolar h-39, and A-4 was replaced with equimolar A-39, to obtain Compound 125 (18.77 g), which was found to have a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:705.2065 (theory: 705.2052). Theoretical element content (%) C 49 H 27 N 3 O 3 : c,83.39; h,3.86; n,5.95. Measured element content (%): c,83.44; h,3.90; n,5.92.
Synthesis example 14: preparation of Compound 133
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-133 and A-4 was replaced with equimolar A-133, to obtain Compound 133 (18.06 g), and the purity of the solid was not less than 99.98% as measured by HPLC. Mass spectrum m/z:687.2332 (theory: 687.2344). Theoretical element content (%) C 47 H 33 N 3 OS: c,82.07; h,4.84; n,6.11. Measured element content (%): c,82.11; h,4.79; n,6.08.
Synthesis example 15: preparation of Compound 142
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-142 and A-4 was replaced with equimolar A-142, to obtain Compound 142 (18.19 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:649.1637 (theory: 649.1624). Theoretical element content (%) C 43 H 24 FN 3 OS: c,79.49; h,3.72; n,6.47. Measured element content (%): c,79.54; h,3.68; n,6.50.
Synthesis example 16: preparation of Compound 150
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-150 and A-4 was replaced with equimolar A-150, to obtain Compound 150 (17.07 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:580.1371 (theory: 580.1358). Theoretical element content (%) C 38 H 20 N 4 OS: c,78.60; h,3.47; n,9.65. Measured element content (%): c,78.55; h,3.51; n,9.69.
Synthesis example 17: preparation of Compound 160
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar F-160 and A-4 was replaced with equimolar A-160, to obtain Compound 160 (18.58 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:707.2019 (theory: 707.2031). Theoretical element content (%) C 49 H 29 N 3 OS: c,83.14; h,4.13; n,5.94. Measured element content (%): c,83.09; h,4.07; n,5.98.
Synthesis example 18: preparation of Compound 260
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-260, h-4 was replaced with equimolar h-260, and A-4 was replaced with equimolar A-39, to give Compound 260 (18.96 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:712.2334 (theory: 712.2345). Theoretical element content (%) C 49 H 24 D 5 N 3 OS: c,82.56; h,4.81; n,5.89. Measured element content (%): c,82.61; h,4.77; n,5.92.
Synthesis example 19: preparation of Compound 295
According to the same manner as that of Compound 25 in Synthesis example 5, f-25 was replaced with equimolar f-295, g-4 was replaced with equimolar g-295, h-25 was replaced with equimolar h-295, and A-25 was replaced with equimolar A-295, to obtain Compound 295 (19.06 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:735.1127 (theory: 735.1114). Theoretical element content (%) C 45 H 22 F 5 NS 2 : c,73.46; h,3.01; n,1.90. Measured element content (%): c,73.51; h,2.97; n,1.86.
Synthesis example 20: preparation of Compound 321
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-39 and A-4 was replaced with equimolar A-321, to obtain Compound 321 (18.10 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:615.1958 (theory: 615.1947). Theoretical element content (%) C 43 H 25 N 3 O 2 : c,83.88; h,4.09; n,6.83. Measured element content (%): c,83.92; h,4.14; n,6.79.
Synthesis example 21: preparation of Compound 352
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-39 and A-4 was replaced with equimolar D-352, to obtain Compound 352 (19.13 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:691.2247 (theory: 691.2260). Theoretical element content (%) C 49 H 29 N 3 O 2 : c,85.07; h,4.23; n,6.07. Measured element content (%): c,85.11; h,4.08; n,6.10.
Synthesis example 22: preparation of Compound 361
According to the same manner as that for Compound 25 of Synthesis example 5, f-25 was replaced with equimolar f-361, h-25 was replaced with equimolar h-4, and A-25 was replaced with equimolar D-361, to obtain Compound 361 (18.54 g), which was found to have a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:687.2356 (theory: 687.2342). Theoretical element content (%) C 46 H 33 N 3 O 2 Si: c,80.32; h,4.84; n,6.11. Measured element content (%): c,80.28; h,4.79; n,6.08.
Synthesis example 23: preparation of Compound 371
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-371, h-4 was replaced with equimolar F-371, and A-4 was replaced with equimolar A-371, to give Compound 371 (18.34 g), which was found to have a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:717.2152 (theory: 717.2165). Theoretical element content (%) C 49 H 27 N 5 O 2 : c,81.99; h,3.79; n,9.76. Measured element content (%): c,82.04; h,3.83; n,9.80.
Synthesis example 24: preparation of Compound 372
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-372, h-4 was replaced with equimolar h-39, and A-4 was replaced with equimolar A-321, to obtain Compound 372 (18.40 g), and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z:691.2249 (theory: 691.2260). Theoretical element contentAmount (%) C 49 H 29 N 3 O 2 : c,85.07; h,4.23; n,6.07. Measured element content (%): c,85.12; h,4.09; n,6.11.
Synthesis example 25: preparation of Compound 385
According to the same manner as that of Compound 25 of Synthesis example 5, g-4 was replaced with equimolar g-385, h-25 was replaced with equimolar h-39, and A-25 was replaced with equimolar A-385, to give Compound 385 (19.70 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:792.2537 (theory: 792.2525). Theoretical element content (%) C 56 H 32 N 4 O 2 : c,84.83; h,4.07; n,7.07. Measured element content (%): c,84.78; h,4.11; n,7.10.
Synthesis example 26: preparation of Compound 405
According to the same manner as that of Compound 4 in Synthesis example 4, g-4 was replaced with equimolar h-260, h-4 was replaced with equimolar h-39, A-4 was replaced with equimolar A-405, to obtain Compound 405 (18.70 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:721.1811 (theory: 721.1824). Theoretical element content (%) C 49 H 27 N 3 O 2 S: c,81.53; h,3.77; n,5.82. Measured element content (%): c,81.49; h,3.82; n,5.79.
Synthesis example 27: preparation of Compound 421
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-421 and A-4 was replaced with equimolar D-421 to give a compoundObject 421 (18.61 g), the purity of the solid detected by HPLC is more than or equal to 99.98%. Mass spectrum m/z:681.1886 (theory: 681.1875). Theoretical element content (%) C 47 H 27 N 3 OS: c,82.80; h,3.99; n,6.16. Measured element content (%): c,82.75; h,4.02; n,6.20.
Synthesis example 28: preparation of Compound 432
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-432, h-4 was replaced with equimolar h-39, and A-4 was replaced with equimolar A-432, to obtain Compound 432 (19.30 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:765.2802 (theory: 765.2814). Theoretical element content (%) C 53 H 39 N 3 OS: c,83.11; h,5.13; n,5.49. Measured element content (%): c,83.08; h,5.09; n,5.52.
Synthesis example 29: preparation of Compound 502
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-260 and A-4 was replaced with equimolar A-502, to obtain Compound 502 (19.21 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:731.2043 (theory: 731.2031). Theoretical element content (%) C 51 H 29 N 3 OS: c,83.70; h,3.99; n,5.74. Measured element content (%): c,83.64; h,4.04; n,5.71.
Synthesis example 30: preparation of Compound 516
Following the same procedure as for the preparation of Compound 4, synthesis example 4, h-4 was replaced with equimolar h-516A-4 was replaced with equimolar D-516 to give compound 516 (18.23 g) with purity of the solid greater than or equal to 99.98% as measured by HPLC. Mass spectrum m/z:667.1519 (theory: 667.1530). Theoretical element content (%) C 43 H 23 F 2 N 3 OS: c,77.35; h,3.47; n,6.29. Measured element content (%): c,77.40; h,3.51; n,6.32.
Synthesis example 31: preparation of Compound 545
According to the same manner as that of Compound 4 in Synthesis example 4, g-4 was replaced with equimolar h-260, h-4 was replaced with equimolar h-545, and A-4 was replaced with equimolar A-321, to give Compound 545 (19.63 g), which was found to have a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:747.2359 (theory: 747.2344). Theoretical element content (%) C 52 H 33 N 3 OS: c,83.51; h,4.45; n,5.62. Measured element content (%): c,83.47; h,4.50; n,5.59.
Synthesis example 32: preparation of Compound 560
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-560, h-4 was replaced with equimolar h-560, and A-4 was replaced with equimolar A-560, to obtain Compound 560 (18.81 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:697.1660 (theory: 697.1646). Theoretical element content (%) C 47 H 27 N 3 S 2 : c,80.89; h,3.90; n,6.02. Measured element content (%): c,80.93; h,3.85; n,5.98.
Synthesis example 33: preparation of Compound 585
According to the same manner as that of Compound 25 of Synthesis example 5, f-25 was replaced with equimolar f-585, h-25 was replaced with equimolar h-260, and A-25 was replaced with equimolar D-585, to give Compound 585 (18.51 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:695.1753 (theory 695.1741). Theoretical element content (%) C 49 H 29 NS 2 : c,84.57; h,4.20; n,2.01. Measured element content (%): c,84.62; h,4.16; n,1.98.
Synthesis example 34: preparation of Compound 598
According to the same manner as that of Compound 4 in Synthesis example 4, g-4 was replaced with equimolar g-598, h-4 was replaced with equimolar h-39, A-4 was replaced with equimolar A-598, to give Compound 598 (18.33 g), and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z:707.2020 (theory: 707.2031). Theoretical element content (%) C 49 H 29 N 3 OS: c,83.14; h,4.13; n,5.94. Measured element content (%): c,83.09; h,4.08; n,5.97.
Synthesis example 35: preparation of Compound 609
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-609 and A-4 was replaced with equimolar A-609, to obtain Compound 609 (18.11 g), and the purity of the solid was found to be not less than 99.96% by HPLC. Mass spectrum m/z:638.2680 (theory: 638.2668). Theoretical element content (%) C 44 H 18 D 9 N 3 O 2 : c,82.73; h,5.68; n,6.58. Measured element content (%): c,82.69; h,5.73; n,6.61.
Synthesis example 36: preparation of Compound 618
According to the same manner as that of Compound 4 of Synthesis example 4, g-4 was replaced with equimolar g-618 and A-4 was replaced with equimolar A-618, to obtain Compound 618 (17.10 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:574.1864 (theory: 574.1876). Theoretical element content (%) C 38 H 18 D 5 N 3 OS: c,79.42; h,4.91; n,7.31. Measured element content (%): c,79.38; h,4.86; n,7.28.
Synthesis example 37: preparation of Compound 671
According to the same manner as that of Compound 4 of Synthesis example 4, H-4 was replaced with equimolar H-39 and A-4 was replaced with equimolar A-671, to obtain Compound 671 (17.61 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:613.2167 (theory: 613.2154). Theoretical element content (%) C 44 H 27 N 3 O: c,86.11; h,4.43; n,6.85. Measured element content (%): c,86.07; h,4.38; n,6.88.
Synthesis example 38: preparation of Compound 680
According to the same manner as that of Compound 4 of Synthesis example 4, A-4 was replaced with equimolar A-680 to obtain Compound 680 (18.86 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:690.2409 (theory: 690.2420). Theoretical element content (%) C 49 H 30 N 4 O: c,85.20; h,4.38; n,8.11. Measured element content (%): c,85.17; h,4.43; n,8.07.
Device example 1: preparation of red light organic electroluminescent device
Firstly, an ITO glass substrate is put into distilled water to be washed for 3 times, the distilled water is used for washing for 20 minutes by ultrasonic waves, the distilled water is used for washing for 2 times repeatedly, the ultrasonic waves are used for washing for 10 minutes, after the distilled water is washed, solvents such as isopropanol, acetone, methanol and the like are used for washing by ultrasonic waves in sequence, and the ITO glass substrate is dried at 120 ℃ and then sent into a vapor deposition machine.
Vapor plating a film HI-1 on the glass substrate as a hole injection layer, wherein the vapor plating thickness is 10nm; vacuum evaporating HT-1 on the hole injection layer as a hole transport layer, wherein the thickness is 120nm; vacuum evaporating EB-1 on the hole transport layer as an electron blocking layer, wherein the thickness is 50nm; vacuum evaporating the compound 4 serving as a first main body material, RH-2 serving as a second main body material and RD-1 serving as a doping material (the mass ratio is 49:49:2) on the electron blocking layer to form a light-emitting layer, wherein the thickness of the light-emitting layer is 35nm; then vacuum evaporating ET-1 and Liq on the luminescent layer as electron transport layers (mass ratio is 1:1), wherein the thickness is 30nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.0nm; vacuum evaporating Al on the electron injection layer to obtain cathode with thickness of 160nm, thereby preparing organic electroluminescent device.
Device examples 2 to 35:
an organic electroluminescent device was produced by the same production method as in device example 1, except that the light-emitting layer of the compound 4 in device example 1 was replaced with the compound 25, the compound 39, the compound 48, the compound 74, the compound 84, the compound 102, the compound 106, the compound 112, the compound 125, the compound 133, the compound 142, the compound 150, the compound 160, the compound 260, the compound 295, the compound 321, the compound 352, the compound 361, the compound 371, the compound 372, the compound 385, the compound 405, the compound 421, the compound 432, the compound 502, the compound 516, the compound 545, the compound 560, the compound 585, the compound 598, the compound 609, the compound 618, the compound 671 and the compound 680, respectively, according to the present invention.
Comparative device examples 1 to 4:
comparative examples 1 to 4: preparation of comparative organic electroluminescent devices 1 to 4
The compound 4 in the light-emitting layer of example 1 was changed to the comparative compounds 1 to 4, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 1 to 4.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 1 to 35 in the device examples according to the present invention and the organic electroluminescent devices obtained in the comparative examples 1 to 4 are shown in the following table 1.
Table 1:
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as shown by the results in Table 1, when the compound containing the nitrogen-containing condensed aromatic ring is used as a host material of a luminescent layer of an organic electroluminescent device, the compound has a higher triplet energy level, and can effectively prevent energy from returning from a guest material to the host material; the HOMO/LUMO energy level is matched with the corresponding energy levels of the adjacent hole transport layer and the electron transport layer, so that a smaller injection potential barrier can be obtained, the device driving voltage is obviously reduced, and the nitrogen-containing condensed aromatic ring compound disclosed by the invention is an OLEDs luminescent layer main body material with excellent performance.
Device example 36 preparation of Green organic electroluminescent device
After the ITO glass substrate is cleaned and dried, transferring the ITO glass substrate into a vapor deposition machine, and vapor deposition of a film HI-2 serving as a hole injection layer on the glass substrate is performed, wherein the vapor deposition thickness is 12nm; vacuum evaporating HT-2 on the hole injection layer as a hole transport layer, wherein the thickness is 130nm; vacuum evaporating EB-2 on the hole transport layer as an electron blocking layer, wherein the thickness is 40nm; vacuum evaporating GH-1 serving as a first main body material, GH-2 serving as a second main body material and GD-1 serving as a doping material (the mass ratio is 47:47:6) on the electron blocking layer to form a light emitting layer, wherein the thickness of the light emitting layer is 40nm; then vacuum evaporating the compound 4 and Liq of the invention on the light-emitting layer as an electron transport layer (mass ratio is 1:1), wherein the thickness is 32nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.1nm; al is evaporated on the electron injection layer in vacuum to be used as a cathode, and the thickness is 170nm, so that the organic electroluminescent device is prepared.
Device examples 37 to 70:
an organic electroluminescent device was produced by the same production method as in device example 36, except that the electron transport layer material of compound 4 in device example 36 was replaced with compound 25, compound 39, compound 48, compound 74, compound 84, compound 102, compound 106, compound 112, compound 125, compound 133, compound 142, compound 150, compound 160, compound 260, compound 295, compound 321, compound 352, compound 361, compound 371, compound 372, compound 385, compound 405, compound 421, compound 432, compound 502, compound 516, compound 545, compound 560, compound 585, compound 598, compound 609, compound 618, compound 671 and compound 680, respectively.
Comparative device examples 5 to 8:
comparative examples 5 to 8: preparation of comparative organic electroluminescent devices 5 to 8
The compounds in the electron transport layer of example 36 were changed to comparative compounds 5 to 8, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 5 to 8.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 36 to 70 in the device examples according to the present invention and the organic electroluminescent devices obtained in the comparative examples 5 to 8 are shown in table 2 below.
Table 2:
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as shown by the results in Table 2, when the compound containing nitrogen condensed aromatic rings is used as an electron transport layer material of an organic electroluminescent device, the compound has higher electron mobility and electrophilicity, stable electrochemistry and electric field stability, can effectively transport electrons to a light emitting layer, ensures the matching of work functions with a cathode and bears a high electric field, and shows that the compound containing nitrogen condensed aromatic rings is an OLEDs electron transport layer material with excellent performance.
Device example 71 preparation of green organic electroluminescent device
After the ITO glass substrate is cleaned and dried, transferring the ITO glass substrate into a vapor deposition machine, and vapor deposition of a film HI-2 serving as a hole injection layer on the glass substrate is performed, wherein the vapor deposition thickness is 12nm; vacuum evaporating HT-2 on the hole injection layer as a hole transport layer, wherein the thickness is 130nm; vacuum evaporating EB-2 on the hole transport layer as an electron blocking layer, wherein the thickness is 40nm; vacuum evaporating GH-1 serving as a first main body material, GH-2 serving as a second main body material and GD-1 serving as a doping material (the mass ratio is 47:47:6) on the electron blocking layer to form a light emitting layer, wherein the thickness of the light emitting layer is 40nm; vacuum evaporating the compound 4 as a hole blocking layer on the light-emitting layer, wherein the thickness is 20nm; then vacuum evaporating ET-2 and Liq on the hole blocking layer as electron transport layers (mass ratio is 1:1), wherein the thickness is 32nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the thickness is 1.1nm; al is evaporated on the electron injection layer in vacuum to be used as a cathode, and the thickness is 170nm, so that the organic electroluminescent device is prepared.
Device examples 72 to 105:
an organic electroluminescent device was produced by the same production method as in device example 71, except that the compound 4 in device example 71 was replaced with the compound 25, the compound 39, the compound 48, the compound 74, the compound 84, the compound 102, the compound 106, the compound 112, the compound 125, the compound 133, the compound 142, the compound 150, the compound 160, the compound 260, the compound 295, the compound 321, the compound 352, the compound 361, the compound 371, the compound 372, the compound 385, the compound 405, the compound 421, the compound 432, the compound 502, the compound 516, the compound 545, the compound 560, the compound 585, the compound 598, the compound 609, the compound 618, the compound 671 and the compound 680, respectively, according to the invention.
Comparative device examples 9 to 12:
comparative examples 9 to 12: preparation of contrast organic electroluminescent devices 9 to 12
The compounds in the hole blocking layer of example 71 were changed to comparative compounds 9 to 12, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 9 to 12.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used.
The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 72 to 105 in the device examples according to the present invention and the organic electroluminescent devices obtained in comparative examples 9 to 12 are shown in table 3 below.
Table 3:
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as shown in the results of Table 3, when the compound containing the nitrogen-containing condensed aromatic ring is used as a hole blocking layer material of an organic electroluminescent device, the compound has higher triplet energy level and better hole blocking capability, and can effectively block holes in a luminescent layer from escaping to an electron transport layer, so that electrons and holes in the luminescent layer are efficiently compounded, the luminous efficiency of the organic electroluminescent device is improved, and the compound containing the nitrogen-containing condensed aromatic ring is an OLEDs hole blocking layer material with excellent performance.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (10)

1. A nitrogen-containing fused aromatic ring compound, characterized in that the nitrogen-containing fused aromatic ring compound has a structure represented by formula I:
The Ar is as follows 1 A group represented by formula II, wherein the ring A is selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C2-C60 heteroaryl group;
said X is selected from O, S, C (R) x ) 2 Or N (R) a )；
Each T is independently selected from CH or N; t fused to ring A is selected from C;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is x Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
The R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkylAny one of a group, a substituted or unsubstituted aryl group of C6 to C60, a substituted or unsubstituted heteroaryl group of C2 to C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60, or a combination thereof;
said n 1 Selected from 0, 1 or 2; said n 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
the Z is 1 ～Z 6 Each independently selected from C (R) y ) Or N, Z 1 ～Z 6 At least one of which is selected from N, and Z 1 ～Z 6 Up to three of which are selected from N;
the R is y Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
the Ar is as follows 2 、Ar 3 At least one of the groups shown in 1-a or 1-b, and the rest is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C6-C60 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C2-C60 heteroaromatic rings;
said Y is independently selected from O, S, C (R c R d ) Or N (R) b )；
The R is c 、R d Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted Any one of aryl group of C6-C30, heteroaryl group of substituted or unsubstituted C2-C30, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and aromatic ring of C6-C30, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and heteroaromatic ring of C2-C30, or R c 、R d Are connected with each other to form a substituted or unsubstituted ring;
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7;
the L is 1 ～L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group of C6 to C60, a substituted or unsubstituted heteroarylene group of C2 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and an aromatic ring of C6 to C60, a fused-back-up-ring group of a substituted or unsubstituted alicyclic ring of C3 to C30 and a heteroaromatic ring of C2 to C60, or a combination thereof.
2. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein Ar 1 Or a group of formula II is selected from the group shown belowAny one of (a) and (b) of (b):
said X is selected from O, S, C (R) x ) 2 Or N (R) a )；
The T is selected from CH or N;
the R is a Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is x Any one selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
the R is 1 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
the R is 2 Independently selectAny one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring;
Said n 1 Selected from 0, 1 or 2; said n 4 Selected from 0, 1, 2, 3, 4, 5 or 6; said n 5 Selected from 0, 1, 2, 3 or 4; said n 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
3. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein Ar 2 、Ar 3 Is selected from one of the following groups represented by formulae 1-a, 1-b:
the R is b Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is c 、R d Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl,Any one of a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring of C6-C30 and an aromatic ring of C6-C30, a substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring of C2-C30 and a heteroaromatic ring of C2-C30, or R c 、R d Are connected with each other to form a substituted or unsubstituted ring;
the R is 3 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 3 Are connected with each other to form a substituted or unsubstituted ring;
said n 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said n 4 Selected from 0, 1, 2, 3, 4, 5 or 6; said n 5 Selected from 0, 1, 2, 3 or 4; said n 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n 7 Selected from 0, 1, 2 or 3; said n 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 9 Selected from 0, 1, 2, 3, 4 or 5; said n 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
4. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein Ar 2 、Ar 3 And when not of the formulae 1-a and 1-b, one or a combination of the following groups are selected:
wherein each r is independently selected from CH or N;
the M is 1 ～M 4 Each independently selected from O, S, C (R) j R k )、N(R z )、Si(R m ) 2 Any one of them;
the R is j 、R k Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R j 、R k Form a substituted or unsubstituted ring;
the R is z Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is m Any one selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring;
The R is h Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is 4 Independently selected from hydrogen, deuterium,Tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of C1 to C30, substituted or unsubstituted cycloalkyl of C3 to C30, substituted or unsubstituted aryl of C6 to C60, substituted or unsubstituted heteroaryl of C2 to C60, fused ring group of substituted or unsubstituted alicyclic of C3 to C30 and aromatic ring of C6 to C60, fused ring group of substituted or unsubstituted alicyclic of C3 to C30 and heteroaromatic ring of C2 to C60, or a combination thereof, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is 5 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
said n 1 Selected from 0, 1 or 2; said n 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said n 5 Selected from 0, 1, 2, 3 or 4; said n 7 Selected from 0, 1, 2 or 3; said n 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said n 9 Selected from 0, 1, 2, 3, 4 or 5.
5. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein Ar 2 、Ar 3 And when not of the formulae 1-a and 1-b, one or a combination of the following groups are selected:
the R is f 、R g Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic rings;
the R is h Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring;
The R is i Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is 4 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 4 Are connected with each other to form a substituted or unsubstituted ring;
the R is 5 Independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring condensed ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring condensed ring group, or adjacent two R 5 Are connected with each other to form a substituted or unsubstituted ring;
the k is 1 Selected from 0, 1, 2, 3, 4 or 5; the k is 2 Selected from 0, 1, 2, 3 or 4; the k is 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the k is 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the k is 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k is 6 Selected from 0, 1 or 2; the k is 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the k is 8 Selected from 0, 1, 2 or 3; the k is 9 Selected from 0, 1, 2, 3, 4, 5 or 6; the k is 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
6. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein L 1 ～L 3 Each independently selected from a single bond or one or a combination of the groups shown below:
wherein each p is independently selected from CH or N;
the M is 5 ～M 7 Each independently selected from O, S, C (R) p R q )、N(R r ) Any one of them;
the R is p 、R q Each independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkylAny one of a cycloalkyl group of a substituted or unsubstituted C3 to C30, an aryl group of a substituted or unsubstituted C6 to C30, a heteroaryl group of a substituted or unsubstituted C2 to C30, a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and an aromatic ring of a C6 to C30, a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and a heteroaromatic ring of a C2 to C30, or R p 、R q Form a substituted or unsubstituted ring;
the R is r Any one selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;
the R is n Each independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is 6 Independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring, or a combination thereof;
Said b 0 Selected from 0, 1 or 2; said b 1 Selected from 0, 1, 2, 3 or 4; said b 2 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
7. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein L 1 ～L 3 Each independently selected from a single bond or one or a combination of the groups shown below:
the R is s Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is t Any one of a cycloalkyl group of a substituted or unsubstituted C3 to C30, an aryl group of a substituted or unsubstituted C6 to C60, a heteroaryl group of a substituted or unsubstituted C2 to C60, a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and an aromatic ring of a C6 to C60, and a fused ring group of an alicyclic ring of a substituted or unsubstituted C3 to C30 and a heteroaromatic ring of a C2 to C60;
The R is v Each independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;
the R is 7 Independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstitutedAny one or a combination of an unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring;
the c 0 Selected from 0, 1 or 2; c 1 Selected from 0, 1, 2, 3 or 4; the c 2 Selected from 0, 1, 2, 3, 4, 5 or 6; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c 5 Selected from 0, 1, 2 or 3; the c 6 Selected from 0 or 1; the c 7 Selected from 0, 1, 2, 3, 4 or 5; the c 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
8. The nitrogen-containing condensed aromatic ring compound according to claim 1, wherein the nitrogen-containing condensed aromatic ring is selected from at least one of the structures shown below:
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9. an organic electroluminescent device comprising an anode, a cathode, an organic layer between the anode and the cathode, wherein the organic layer comprises at least one of an electron transport layer or a hole blocking layer comprising at least one of the nitrogen-containing condensed aromatic ring-containing compounds according to any one of claims 1 to 8.
10. An organic electroluminescent device comprising an anode, a cathode, an organic layer between the anode and the cathode, characterized in that the organic layer comprises a light-emitting layer comprising at least one of the nitrogen-containing condensed aromatic ring-containing compounds according to any one of claims 1 to 8.
CN202311118235.6A 2023-08-31 2023-08-31 Nitrogen-containing condensed aromatic ring compound and organic electroluminescent device thereof Pending CN117164574A (en)

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