CN108822083A - A kind of carbazole compound and its application - Google Patents

A kind of carbazole compound and its application Download PDF

Info

Publication number
CN108822083A
CN108822083A CN201810879592.7A CN201810879592A CN108822083A CN 108822083 A CN108822083 A CN 108822083A CN 201810879592 A CN201810879592 A CN 201810879592A CN 108822083 A CN108822083 A CN 108822083A
Authority
CN
China
Prior art keywords
group
atom
heteroaryl
aryl
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN201810879592.7A
Other languages
Chinese (zh)
Inventor
马腾达
黄达
荆铭
荆一铭
陈少海
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ACC Acoustic Technologies Shenzhen Co Ltd
Original Assignee
ACC Acoustic Technologies Shenzhen Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ACC Acoustic Technologies Shenzhen Co Ltd filed Critical ACC Acoustic Technologies Shenzhen Co Ltd
Priority to CN201810879592.7A priority Critical patent/CN108822083A/en
Publication of CN108822083A publication Critical patent/CN108822083A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)

Abstract

The invention belongs to field of organic electroluminescent materials, a kind of carbazole compound and its application are disclosed.Carbazole compound disclosed in this invention has structure shown in formula (I), is a kind of material of main part of carrier balance, using the compound of the present invention as the material of main part of OLED device, cut-in voltage is lower, and luminous efficiency is higher；Moreover, because in 2 introducing substituent groups of carbazole so that the structure of carbazole compound of the invention be it is asymmetric, be conducive to improve film forming, keep the stability of OLED device in long-term use.

Description

Carbazole compound and application thereof
Technical Field
The invention belongs to the field of organic electroluminescent materials, and particularly relates to a carbazole compound and application thereof.
Background
In the technical field of organic electroluminescent devices, high-efficiency and long-life luminescence can be realized in different modes, and for a luminescent layer of an emission spectrum, one mode is to improve the efficiency and the service life by adopting a host-guest doping mode.
In order to achieve high efficiency of light emission, avoid energy from a guest material to a host material from being transferred back, and confine triplet excitons in a light emitting layer, a triplet energy level of the host material should be greater than a triplet energy level of a dopant material. When the triplet energy level of the host material is less than the triplet energy of the dopant material, a phenomenon of reverse transition from the dopant material to the host material energy level will occur, resulting in a decrease in light emission efficiency. Therefore, for the light emitting material layer, a host material having high thermal stability and higher triplet energy than a dopant material is required.
In the prior art, most of the host materials are hole transport type host materials or electron transport type host materials. Such a unipolar host material tends to form an unfavorably narrow recombination region due to imbalance in carrier transport properties. In general, when a hole transport type host material is used, a charge recombination region is generated at an interface between a light emitting layer and an electron transport layer, and when an electron transport type host material is used, a charge recombination region is generated at an interface between a light emitting layer and a hole transport layer. However, the weak carrier mobility and the unbalanced charge in the emission layer are disadvantageous to the light emission efficiency of the organic light emitting device. Meanwhile, the narrow charge recombination region of the organic electrophosphorescent device accelerates the triplet-triplet annihilation process, thereby reducing the luminous efficiency, especially under the current density condition. To avoid this effect, the strategies generally adopted are: (1) using two light emitting layers, one of which uses a hole transport type host material and the other of which uses an electron transport type host material; (2) hole-transporting and electron-transporting host materials are mixed in a single light-emitting layer. However, both strategies complicate the fabrication of the device and the mixed host materials can lead to phase separation problems.
In recent years, host materials with balanced hole and electron carrier capabilities attract people's attention in the field of organic electrophosphorescent devices, and the materials not only improve the performance of the devices, but also simplify the structure of the devices, so that the host materials have great demand.
Disclosure of Invention
The invention aims to provide a carbazole compound and application thereof, wherein the carbazole compound is a host material which contains pyridine and carbazole groups and has balanced current carriers.
The purpose of the invention is realized by the following technical scheme:
embodiments of the present invention provide a carbazole compound having a structure represented by formula (I):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino.
In the structure of the compound provided by the embodiment of the present invention, the carbazole structure also includes an N-heterocyclic carbazole structure, and the N-heterocyclic carbazole structure is also referred to as a carboline structure.
Alternatively, R1And R2Are different substituents.
Alternatively, the carbazole compound provided by the embodiment of the present invention has a structure represented by formula (I-2):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino.
Alternatively, R1、R2Each independently having a structure represented by formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently representN atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr,
and Rm, Rn, Ro, Rp, Rq, Rr each independently represent C1-C24 alkyl, C6-C72 aryl, or C3-C72 heteroaryl.
Optionally, in the structure shown in formula (II) or (III), Ar is connected1And Ar2Is one or two, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
Alternatively, R1、R2Each independently having a structure selected from one of:
wherein,
R1-R16each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine groupC6-C18 aryloxy or C3-C18 heteroaryloxy;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
Further alternatively, R1、R2Each independently has a structure of one of:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridyl or naphthyl.
Alternatively, an embodiment of the present invention provides a carbazole compound having a structure selected from one of the following:
embodiments of the present invention also provide use of the carbazole compound described above in an organic electroluminescent device.
Compared with the prior art, the substituted carbazole compound provided by the embodiment of the invention obtains a host material containing pyridine and carbazole groups and having carrier balance by introducing a substituent at the 2-position of carbazole. The compound provided by the embodiment of the invention is used as a main material of an OLED device, and has lower starting voltage and higher luminous efficiency. In addition, the carbazole compound provided by the embodiment of the invention has an asymmetric structure, so that the carbazole compound is beneficial to improving the film forming property and further beneficial to maintaining the stability of the OLED device in long-term use.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention will be described in detail with reference to the following examples. However, it will be appreciated by those of ordinary skill in the art that numerous technical details are set forth in order to provide a better understanding of the present invention in its various embodiments. However, the technical solutions claimed in the claims of the present invention can be implemented without these technical details and with various changes and modifications based on the following embodiments.
Compound (I)
In some embodiments of the present invention, a carbazole compound is provided having a structure represented by formula (I):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino.
In the structure of the compound provided by the embodiment of the present invention, the carbazole structure also includes an N-heterocyclic carbazole structure, and the N-heterocyclic carbazole structure is also referred to as a carboline structure.
In some embodiments of the invention, R1And R2Are different substituents.
In some embodiments of the present invention, carbazole compounds are provided having the structure shown in formula (I-2):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino. .
In some embodiments of the invention, R1、R2Each independently having a structure represented by formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently represents an N atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr,
and Rm, Rn, Ro, Rp, Rq, Rr each independently represent C1-C24 alkyl, C6-C72 aryl, or C3-C72 heteroaryl.
In some embodiments of the invention, Ar is attached to the structure of formula (II) or (III)1And Ar2Is one or two, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
In some embodiments of the invention, R1、R2Each independently having a structure selected from one of:
wherein,
R1-R16each independently represents hydrogenAn atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group.
Further alternatively, R1、R2Each independently has a structure of one of:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridylOr naphthyl.
In some embodiments of the present invention, carbazole compounds are provided having a structure selected from one of the following:
general synthetic route:
specific embodiments of the present invention also provide a preparation method of the carbazole compound described above, which is synthesized by the following general synthetic methods (Syn-1), (Syn-2), and (Syn-3):
wherein S is1、S2、S3、S4、S5、S6Each independently represents a reactive leaving group, which is various, by way of example and without limitation, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a boric acid group, a borate group; the other groups are as defined for the general formula (I) herein. The above-mentioned reactive leaving group leaving during the reactionWhen it is used, it may be charged, for example, fluorine atom is left as a negative ion.
The specific reaction conditions are not limited, such as temperature, solvent type and amount, catalyst type and amount, cocatalyst type and amount, alkali type and amount, water amount, and reaction substrate feeding ratio and sequence, and those skilled in the art can easily and reasonably generalize from the examples of the present invention, and the general basis for selection can refer to relevant documents, patents and books of organic synthesis reactions. The coupling reaction is involved, and the related information of Suzuki reaction and Ullmann reaction can be preferentially referred; reactions involving alkylation may be preferentially referred to in connection with parkinsonian alkylation.
Synthesis example:
the following provides methods for preparing the compounds disclosed in the present invention. The present disclosure is not intended to be limited to any one of the methods recited herein. One skilled in the art can readily modify the methods described or utilize different methods to prepare one or more of the disclosed compounds. The following aspects are merely exemplary and are not intended to limit the scope of the present disclosure. The temperature, catalyst, concentration, reactant composition, and other process conditions may be varied, and appropriate reactants and conditions for the desired complex may be readily selected by one skilled in the art to which the present disclosure pertains.
Abbreviations in the examples of the present invention mean: PE: petroleum ether; DCM: dichloromethane; EA: ethyl acetate; CDCl3, deuterated chloroform; MeTHF: and (3) methyl tetrahydrofuran. The various starting materials for the reactions in the examples of the present invention are commercially available or synthesized by known methods reported in the literature.
EXAMPLE 1 Synthesis of 2- (dibenzofuran-2-yl) -6- [ (dibenzofuran-2-yl) -carbazol-9-yl ] pyridine (H1)
Adding 320mg of 2- (2-bromocarbazole-9-yl) -6-bromopyridine, 340mg of 2-dibenzofuranboronic acid, 80mg of palladium tetratriphenylphosphine, 420mg of potassium phosphate, 20ml of toluene, 2ml of purified water into a reaction bottle, replacing the system with nitrogen for 3 times, heating the system to 120 ℃, carrying out heat preservation reaction for 24 hours, cooling to room temperature, carrying out suction filtration on the system, concentrating the filtrate, carrying out column chromatography, and eluting DCM: PE ═ 1: 20, the eluate was concentrated to give 450mg of a white solid with a yield of 85%.
1H NMR(400MHz,Solvent：DMSO-d6)δppm 7.28-7.43(m,8H)7.43-7.52(m,3H)7.57-7.62(m,1H)7.65-7.72(m,1H)7.79-7.92(m,4H)7.93-8.02(m,3H)8.04-8.08(m,2H)8.12-8.18(m,1H)8.47-8.53(m,1H)。
Example 2: synthesis of 2- (carbazol-9-yl) -6- [2- (carbazol-9-yl-) -carbazol-9-yl ] pyridine (H2)
Adding 261mg of 2- (2-bromocarbazole-9-yl) -6-bromopyridine, 220mg of carbazole, 15mg of cuprous iodide, 18mg of Trans-cyclohexanediamine, 400mg of potassium phosphate and 20ml of toluene into a reaction bottle, replacing the system with nitrogen for 3 times, heating the system to 120 ℃, performing heat preservation reaction for 48 hours, cooling to room temperature, performing suction filtration on the system, concentrating the filtrate, performing column chromatography, and eluting DCM: PE ═ 1: 5, the eluate was concentrated to give 236mg of a white solid in 63% yield.
1H NMR(400MHz,Solvent：DMSO-d6)δppm 7.10-7.18(m,1H)7.24-7.40(m,9H)7.42-7.52(m,4H)7.55-7.59(m,1H)7.81-7.90(m,3H)7.91-7.97(m,2H)8.06-8.18(m,5H)8.20-8.23(m,1H)。
Example 3: synthesis of 2- (1-N-carbolin-9-yl) -6- [2- (1-N-carbolin-9-yl-) -carbazol-9-yl ] pyridine (H3)
Adding 281mg of 2- (2-bromocarbazole-9-yl) -6-bromopyridine, 240mg of 1-carboline, 17mg of cuprous iodide, 20mg of Trans-cyclohexanediamine, 420mg of potassium phosphate and 20ml of toluene into a reaction bottle, replacing the system with nitrogen for 3 times, heating the system to 120 ℃, carrying out heat preservation reaction for 24 hours, cooling to room temperature, carrying out suction filtration on the system, concentrating the filtrate, carrying out column chromatography, and eluting with EA: PE ═ 1: 5, the eluate was concentrated to give 246mg of a white solid in a yield of 61%.
1H NMR(400MHz,Solvent：DMSO)δppm 7.17-7.25(m,2H)7.27-7.37(m,3H)7.41-7.58(m,5H)7.64(d,J＝7.98Hz,1H)7.72-7.79(m,1H)7.88-7.97(m,2H)8.01-8.07(m,1H)8.09-8.24(m,4H)8.28-8.39(m,3H)8.43-8.52(m,2H)。
Example 4: synthesis of 2- (3, 6-di-tert-butylcarbazol-9-yl) -6- [2- (3, 6-di-tert-butyl-carbazol-9-yl-) -carbazol-9-yl ] pyridine (H4)
Adding 402mg of 2- (2-bromocarbazole-9-yl) -6-bromopyridine, 600mg of tert-butylcarbazole, 20mg of cuprous iodide, 24mg of Trans-cyclohexanediamine, 500mg of potassium phosphate and 20ml of toluene into a reaction bottle, replacing the system with nitrogen for 3 times, heating the system to 120 ℃, carrying out heat preservation reaction for 48 hours, cooling to room temperature, carrying out suction filtration on the system, concentrating the filtrate, carrying out column chromatography, and eluting DCM: PE ═ 1: 5, the eluate was concentrated to give 576mg of a white solid in 72% yield.
1H NMR(400MHz,Solvent：DMSO-d6)δppm 1.24-1.48(s,36H)7.18-7.28(m,3H)7.30-7.36(m,3H)7.38-7.45(m,3H)7.47-7.53(m,1H)7.54-7.61(m,3H)7.81-7.88(m,1H)7.90-7.97(m,2H)8.05(s,2H)8.10-8.14(m,2H)8.15-8.17(m,1H)8.18-8.23(m,1H)。
EXAMPLE 5 Synthesis of 2- (1-N-carbolin-9-yl) -6- [2- (dibenzofuran-2-yl) -carbazol-9-yl ] pyridine (H5)
Adding 325mg of 2- (1-N-carboline-9-yl) -6-bromopyridine into a reaction bottle, sequentially adding 400mg of 2- (dibenzofuran-2-yl) -carbazole, 20mg of cuprous iodide, 24mg of Trans-cyclohexanediamine, 300mg of anhydrous potassium phosphate, 50ml of toluene and 3 times of nitrogen replacement system, heating the system to 130 ℃, preserving heat for 24 hours, cooling to room temperature, adding 20ml of purified water, separating liquid, drying an organic phase, concentrating, and performing column chromatography to obtain a white solid, wherein 400mg of the white solid is obtained. Mass spectrum molecular ion peaks: 576.
compound performance detection
Dissolving the compound in MeTHF, measuring photoluminescence spectrum at normal temperature to obtain a first singlet state energy level S1 energy level, and measuring photoluminescence spectrum at low temperature 77K to obtain a first triplet state energy level T1 energy level. The compound was heated at a rate of 10K/min under nitrogen to obtain a glass transition temperature Tg. The results of the optical and thermodynamic data obtained by the above method are shown in table 1 below:
optical and thermodynamic data for the compounds of Table 1
Name of Compound S1(eV) T1(eV) Tg(℃)
H1 3.54 2.80 139
H2 3.65 3.03 163
H3 3.57 2.84 173
H4 3.56 2.95 176
As can be seen from the data in table 1, the compound prepared by the embodiment of the present invention has a high T1 level, and can be used as a host material of a blue light material, particularly a deep blue light material; in addition, the glass transition temperature is higher and exceeds 130 ℃, which is beneficial to improving the tolerance of the heat of the focusing ears in long-term work.
Organic light emitting diode device
Embodiments of the present invention also provide an organic light emitting diode device comprising the carbazole compound in the above examples.
In some embodiments provided herein, the pyridine carbazole compounds of the present invention are hole transport materials, host materials, or guest materials in organic light emitting diode devices. Preferably used as the host material.
Preparation of organic light-emitting diode device
The device is manufactured by adopting an industry conventional preparation method, and the following modes can be selected: firstly, a proper anode is selected for introducing holes, other materials can be evaporated on the surface of the anode to change the work function of the anode, then an organic layer is evaporated, and then a cathode is continuously evaporated to play a role in introducing electrons.
The organic layer may be one layer or a plurality of layers. Further, the organic layer includes a hole transport layer, a light emitting layer and an electron transport layer. The hole transport layer may further have a hole injection function, an electron blocking function, or an exciton blocking function, the electron transport layer may further have an electron injection function, a hole blocking function, or an exciton blocking function, and the light emitting layer may be a doped structure. When the light-emitting layer has a doped structure, a high weight percentage is referred to as a host material, and a low weight percentage is referred to as a guest material. The host material may be only one or a plurality of. When the doped structure is adopted, the doping proportion of the guest material is 0.1-49.9%, preferably 0.5-20%.
By way of example and not limitation, the material of the present invention used as the host material can be prepared as follows:
placing the cleaned ITO glass substrate in a vacuum chamber, and vacuumizing to 10 DEG-5Pa, evaporating a layer of 10nm 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), continuously evaporating a layer of 20nm 4, 4' -tris (1-naphthylphenylamino) triphenylamine (1-TNATA), and continuously evaporating a layer of 10nm 9,9- (1, 3-phenyl) dicarbazole (mCP); continuously carrying out co-evaporation on a layer of 30nm iridium bis (2, 4-difluorophenylpyridine) -tetrakis (1-pyrazolyl) borate (FIr6) and a light-emitting layer of the compound, wherein the doping concentration is 8 wt%; continuously evaporating a 50nm TmPyPB layer as an electron transport layer; and continuously evaporating a layer of lithium fluoride with the thickness of 1nm, and continuously evaporating a layer of aluminum electrode with the thickness of 100 nm.
To further illustrate the superior properties of the materials of the present invention, the same device fabrication method was used, replacing only the compound of the present invention with compound (C1).
The turn-on voltage (Von) and efficiency decay of the device to 95% lifetime was measured and the data is shown in table 2 below:
TABLE 2 Start-Up Voltage and Life data
Von LT
H1 3.4 59
H2 3.5 73
H3 3.7 68
H4 3.4 65
C1 4.9 35
It can be seen that the turn-on voltage of the device using the compound provided by the invention as the light-emitting layer is obviously reduced, and the service life is obviously prolonged.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the invention, and that various changes in form and details may be made therein without departing from the spirit and scope of the invention in practice.

Claims (10)

1. A carbazole compound having a structure represented by formula (I):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkylC1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino.
2. The carbazole compound according to claim 1, wherein R is1And R2Are different substituents.
3. The carbazole compound according to claim 1, having a structure represented by formula (I-2):
wherein,
N1、N2、N3、N4、N5、N6、N7、N8each independently represents an N atom or CRx, and Rx represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamine;
x, Y each independently represents an N atom or CRy, wherein Ry represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino;
R1、R2each independently represents deuterium, fluorine, chlorine, bromine, iodine, C1-C24 alkyl, C1-C24 alkoxy, C1-C24 alkylthio, C2-C24 alkylamino, C6-C72 aryl, C6-C72 aryloxy, C6-C72 arylthio, C7-C72 arylamino, C3-C72 heteroaryl, C3-C72 heteroaryloxy, C3-C72 heteroarylthio or C4-C72 heteroarylamino.
4. The carbazole compound according to claim 1, wherein R is1、R2Each independently having a structure represented by formula (II) or (III):
wherein,
Ar1、Ar2each independently represents a C1-C24 alkyl group, a C6-C72 aryl group, a C3-C72 heteroaryl group; ar (Ar)1And Ar2Not connected or Ar1And Ar2Connected by single, double, carbon or hetero atoms;
M1、M2、M3、M4each independently represents an N atom or CRz, and Rz represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C24 alkyl group, a C1-C24 alkoxy group, a C1-C24 alkylthio group, a C2-C24 alkylamino group, a C6-C72 aryl group, a C6-C72 aryloxy group, a C6-C72 arylthio group, a C7-C72 arylamino group, a C3-C72 heteroaryl group, a C3-C72 heteroaryloxy group, a C3-C72 heteroarylthio group, or a C4-C72 heteroarylamino group;
z represents an oxygen atom, a sulfur atom, a sulfone group, a sulfoxide group, NRm, CRnRo, SiRpRq or BRr,
and Rm, Rn, Ro, Rp, Rq, Rr each independently represent C1-C24 alkyl, C6-C72 aryl, or C3-C72 heteroaryl.
5. The carbazole compound according to claim 4, wherein the linkage Ar is1And Ar2Is one or two, said carbon atoms being substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group; the heteroatom is an oxygen atom, a sulfur atom, a silicon atom, a nitrogen atom or a boron atom, the sulfur atom is unsubstituted or substituted by one or two oxygen atoms, and the silicon atom, the nitrogen atom or the boron atom is substituted by a hydrogen atom, a deuterium atom, a C1-C12 alkyl group, a C6-C36 aryl group or a C3-C36 heteroaryl group.
6. The carbazole compound according to claim 5, wherein R is1、R2Each independently having a structure selected from one of:
wherein,
R1-R16each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R21-R26each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R31-R34each independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C18 aryl group, a C3-C18 heteroaryl group, a C7-C18 arylamine group, a C4-C18 heteroarylamine group, a C6-C18 aryloxy group or a C3-C18 heteroaryloxy group;
R101-R106each independently represents a C1-C12 alkyl group, a C6-C18 aryl group, or a C3-C18 heteroaryl group;
R201-R205each independently represents a C1-C12 alkyl group, a C6-C18 aryl group or a C3-C18 heteroaryl group。
7. The carbazole compound according to claim 6, wherein R is1、R2Each independently has a structure of one of:
wherein,
R210、R220、R230、R240、R250、R260、R310、R320、R340each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a tolyl group, a dimethylphenyl group, a pyridyl group, a naphthyl group, a carbazolyl group or a carbolinyl group;
R2010represents methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, tolyl, dimethylphenyl, pyridyl or naphthyl.
8. The carbazole compound according to claim 1, having a structure selected from one of the following:
9. use of the carbazole compound as claimed in any one of claims 1 to 8 in an organic electroluminescent device.
10. The use according to claim 9, wherein the carbazole compound is a hole-transporting material, a host material or a guest material in the organic electroluminescent device.
CN201810879592.7A 2018-08-03 2018-08-03 A kind of carbazole compound and its application Withdrawn CN108822083A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810879592.7A CN108822083A (en) 2018-08-03 2018-08-03 A kind of carbazole compound and its application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810879592.7A CN108822083A (en) 2018-08-03 2018-08-03 A kind of carbazole compound and its application

Publications (1)

Publication Number Publication Date
CN108822083A true CN108822083A (en) 2018-11-16

Family

ID=64153576

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810879592.7A Withdrawn CN108822083A (en) 2018-08-03 2018-08-03 A kind of carbazole compound and its application

Country Status (1)

Country Link
CN (1) CN108822083A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109851609A (en) * 2018-12-27 2019-06-07 瑞声科技（南京）有限公司 A kind of carbazole pyridine compounds and its application

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102382105A (en) * 2011-09-21 2012-03-21 东莞彩显有机发光科技有限公司 Bipolar host material used for blue emitting phosphor
KR20140083254A (en) * 2012-12-26 2014-07-04 엘지디스플레이 주식회사 Blue phophorescene compounds and organic light emitting diode devices using the same
KR20150135599A (en) * 2014-05-22 2015-12-03 (주)아이티켐 Noble Organic Light-Emitting Compound and Organic Light-Emitting Device Using the Same
KR20160077735A (en) * 2014-12-24 2016-07-04 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
KR20170069119A (en) * 2015-12-10 2017-06-20 성균관대학교산학협력단 Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same
CN108117540A (en) * 2016-11-30 2018-06-05 乐金显示有限公司 Organic compound, Organic Light Emitting Diode and organic light-emitting display device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102382105A (en) * 2011-09-21 2012-03-21 东莞彩显有机发光科技有限公司 Bipolar host material used for blue emitting phosphor
KR20140083254A (en) * 2012-12-26 2014-07-04 엘지디스플레이 주식회사 Blue phophorescene compounds and organic light emitting diode devices using the same
KR20150135599A (en) * 2014-05-22 2015-12-03 (주)아이티켐 Noble Organic Light-Emitting Compound and Organic Light-Emitting Device Using the Same
KR20160077735A (en) * 2014-12-24 2016-07-04 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
KR20170069119A (en) * 2015-12-10 2017-06-20 성균관대학교산학협력단 Organic electroluminescent compound, producing method of the same and organic electroluminescent device including the same
CN108117540A (en) * 2016-11-30 2018-06-05 乐金显示有限公司 Organic compound, Organic Light Emitting Diode and organic light-emitting display device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109851609A (en) * 2018-12-27 2019-06-07 瑞声科技（南京）有限公司 A kind of carbazole pyridine compounds and its application

Similar Documents

Publication Publication Date Title
TWI567164B (en) Organic electroluminescent element materials and organic electroluminescent elements
US9269908B2 (en) Bipolar compound as a host material for organic light emitting diodes
KR101791022B1 (en) spiro compounds and organic light-emitting diode including the same
KR20120117675A (en) Pyrene derivative compounds and organic light-emitting diode including the same
KR20110123701A (en) Anthracene-based compound and organic electroluminescent devices comprising the same
CN111675701B (en) Triphenylamine structure-based organic electroluminescent compound and organic electroluminescent device
KR101897045B1 (en) Organic metal compounds and organic light emitting diodes comprising the same
KR20150113642A (en) Novel aromatic amine compounds for organic light-emitting diode and organic light-emitting diode including the same
CN116391008A (en) Carbazole-containing compound and organic electroluminescent device
CN113527268B (en) Compound containing biscarbazole and triazine structure and organic electroluminescent device
KR20130121597A (en) Using triphenylamine as hole transporting mateial and organic electroluminescent device using the same
KR20140138393A (en) Asymmetric ortho-Terphenyl Derivatives and Organic light emitting device Comprising the Same
CN113801109A (en) Compound containing biscarbazole structure and organic electroluminescent device
CN108912105A (en) A kind of double carbazole compounds symmetrically replaced and its application
Lin et al. New high-T g bipolar benzimidazole derivatives in improving the stability of high-efficiency OLEDs
CN108912097A (en) A kind of pyridine compounds and its application
CN110950846B (en) Benzimidazole bipyrimidine derivative and application thereof
CN110655486A (en) Compound with dibenzosuberene as core and application thereof
CN103183711B (en) A kind of two-triaryl amine replaces phosphine oxygen base Benzophenanthrene compound, intermediate and preparation method and application
CN108822083A (en) A kind of carbazole compound and its application
CN113292488B (en) Cyano-containing aza-benzene compound, application thereof and organic electroluminescent device containing compound
KR101779914B1 (en) Naphthalene derivatives and organic light-emitting diode including the same
CN111620887B (en) Compound taking fused quinazoline as receptor and application thereof
CN108707136A (en) A kind of pyridine triphenylene compound and its application
KR20150114658A (en) An organoelectro luminescent compounds and organoelectro luminescent device using the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20181116