CN113651826A - Nitrogen-containing compound, and electronic element and electronic device using same - Google Patents

Nitrogen-containing compound, and electronic element and electronic device using same Download PDF

Info

Publication number
CN113651826A
CN113651826A CN202011460044.4A CN202011460044A CN113651826A CN 113651826 A CN113651826 A CN 113651826A CN 202011460044 A CN202011460044 A CN 202011460044A CN 113651826 A CN113651826 A CN 113651826A
Authority
CN
China
Prior art keywords
carbon atoms
group
substituted
unsubstituted
nitrogen
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.)
Granted
Application number
CN202011460044.4A
Other languages
Chinese (zh)
Other versions
CN113651826B (en
Inventor
马天天
杨敏
南朋
郑奕奕
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.)
Shaanxi Lighte Optoelectronics Material Co Ltd
Original Assignee
Shaanxi Lighte Optoelectronics Material 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 Shaanxi Lighte Optoelectronics Material Co Ltd filed Critical Shaanxi Lighte Optoelectronics Material Co Ltd
Priority to CN202011460044.4A priority Critical patent/CN113651826B/en
Priority to PCT/CN2021/130172 priority patent/WO2022121618A1/en
Publication of CN113651826A publication Critical patent/CN113651826A/en
Application granted granted Critical
Publication of CN113651826B publication Critical patent/CN113651826B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • 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
    • C09K2211/1011—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
    • C09K2211/1018—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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • 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
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

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

Abstract

The present application relates to a nitrogen-containing compound having a structure represented by the following formula I, and an electronic element and an electronic device using the same. The nitrogen-containing compound can remarkably reduce the driving voltage of a device and improve the device performanceService life; in addition, the compounds of the present application can also improve the efficiency of the device.
Figure DDA0002831183170000011

Description

Nitrogen-containing compound, and electronic element and electronic device using same
Technical Field
The present invention relates to the field of organic material technology, and in particular, to a nitrogen-containing compound, and an electronic element and an electronic device using the same.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
Taking an organic electroluminescent device as an example, the organic electroluminescent device generally comprises an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
At present, the problems of reduced luminous efficiency, shortened service life and the like exist in the using process of an organic electroluminescent device, so that the performance of the organic electroluminescent device is reduced.
Disclosure of Invention
In view of the above problems in the prior art, an object of the present invention is to provide a nitrogen-containing compound that can be used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an electronic component and an electronic apparatus using the same.
In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound, the organic compound having a structure represented by formula I below:
Figure BDA0002831183150000011
wherein, T1Selected from O or S;
L、L1the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L2selected from single bond, substituted or unsubstituted arylene with 6-20 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 2-30 carbon atoms;
Ar2selected from the structures shown in formula II or formula III;
wherein X, Y are independently selected from single bond, O, S, C (R)5R6) Or N (R)7) And X and Y are not single bonds at the same time;
R5、R6and R7The same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
z is selected from O, S, C (R)8R9) Or N (R)10)；
R8、R9And R10The same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
optionally, any R5And R6、R8And R9Form a saturated or unsaturated ring having 3 to 14 carbon atoms with the atoms to which they are commonly attached;
R1、R2、R3and R4The same or different, and each is independently selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 24 carbon atoms;
R1～R4with RiIs represented by n1～n4With niI is a variable, 1,2, 3 or 4, n1、n2、n3And n4Each represents R1、R2、R3And R4The number of (2);
wherein, when i is 1, n1Selected from 0, 1,2 or 3; when i is 2, 3 or 4, n1Selected from 0, 1,2, 3 or 4;
and when n isiWhen greater than 1, any two niThe same or different;
optionally, any two adjacent RiThe benzene ring connected with the compound forms a naphthalene ring or a phenanthrene ring;
L、L1、Ar1and R5～R10The substituents are the same or different and are each independently selected from deuterium, a halogen group, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, phosphinyloxy having 6 to 18 carbon atoms.
A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound according to the first aspect of the present application;
preferably, the functional layer includes an organic light emitting layer including the nitrogen-containing compound;
more preferably, the organic light-emitting layer includes a host material and a guest material, and the host material includes the nitrogen-containing compound.
A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.
The nitrogen-containing compound can remarkably reduce the driving voltage of a device and prolong the service life of the device; in addition, the compounds of the present application can also improve the efficiency of the device.
The application provides a structure of a nitrogen-containing compound, wherein azadibenzofuran/dibenzothiophene and triazine are used as core groups, and electron-rich fused heteroaryl is used as one of fixed substituent groups; the aza-dibenzofuran/dibenzothiophene has high electron mobility and rate, and can effectively improve the electron injection and transmission capability of the material by combining with an electron-deficient triazine group; on the basis, the electron-rich thick heteroaryl is used as a fixed substituent group, and the nitrogen-doped position is fixed at the ortho position of O or S, so that the molecular polarity can be effectively improved by the specific connection mode, and the electron transport capability of the material is further improved. Secondly, the compound has a high T1 value, and is particularly suitable for a host material of an organic electroluminescent device, especially a green host material. When the compound is used as a luminescent layer material of an organic electroluminescent device, the electron transport performance of the device is effectively improved, so that the balance degree of hole and electron injection is enhanced, the luminescent efficiency of the device is improved, and the service life of the device is prolonged.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. a first electronic device.
Detailed Description
The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula I below:
Figure BDA0002831183150000021
Figure BDA0002831183150000031
wherein, T1Selected from O or S;
L、L1the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L2selected from single bond, substituted or unsubstituted arylene with 6-20 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 2-30 carbon atoms;
Ar2selected from the structures shown in formula II or formula III;
wherein, X, Y are independently selected from O, S, C (R)5R6) Or N (R)7) And X and Y are not single bonds at the same time;
R5、R6and R7The same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
z is selected from O, S, C (R)8R9) Or N (R)10)；R8、R9And R10Are the same or different and are each independently selected fromAn alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
optionally, any R5And R6、R8And R9Form a saturated or unsaturated ring having 3 to 14 carbon atoms with the atoms to which they are commonly attached;
R1、R2、R3and R4Same or different and each is independently selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an unsubstituted aryl group having 6 to 20 carbon atoms, an unsubstituted heteroaryl group having 3 to 24 carbon atoms;
R1～R4with RiIs represented by n1～n4With niI is a variable, 1,2, 3 or 4, n1、n2、n3And n4Each represents R1、R2、R3And R4The number of (2);
wherein, when i is 1, n1Selected from 0, 1,2 or 3;
when i is 2, 3 or 4, n1Selected from 0, 1,2, 3 or 4;
and when n isiWhen greater than 1, any two niThe same or different;
optionally, any two adjacent RiThe benzene ring connected with the compound forms a naphthalene ring or a phenanthrene ring;
L2the substituents in (1) are selected from deuterium, halogen groups, cyano, phenyl;
L、L1、Ar1and R5～R10Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, trialkylsilyl having 3 to 12 carbon atoms, triarylsilyl having 18 to 24 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkane having 1 to 10 carbon atomsA cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and a phosphinyloxy group having 6 to 18 carbon atoms.
In this application, when formula II is linked to formula I, it refers to the main portion of the group of formula II
Figure BDA0002831183150000032
Is linked to formula I by a single bond and not to R as a substituent3、R4、R5、R6And R7And (4) connecting. For example, when a linkage of formula I is attached to a linkage of formula II, and X is N, and Y is O, the group of formula II is
Figure BDA0002831183150000033
Similarly, when formula III is linked to formula I, it refers to the main moiety of the group of formula III
Figure BDA0002831183150000034
Is linked to formula I by a single bond and not to R as a substituent3、R4、R5、R6、R7、R8、R9And R10And (4) connecting. For example, when formula I is linked to formula III, X is N, Y is a single bond, and Z is O, the group of formula III is
Figure BDA0002831183150000041
In this application, the terms "optional" and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, two adjacent substituents form a ring; "means that these two substituents may but need not form a ring, including: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring.
In the present applicationOptionally, RiWherein two adjacent form an unsaturated aromatic ring "means that any two adjacent RiAn unsaturated aromatic ring may be formed, or a ring may not be formed. For example, when adjacent R5And R6Adjacent R8And R9Two adjacent R8And R9When the ring is formed, the carbon number of the ring is 3 to 14, and the ring may be saturated or unsaturated. For example: cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, phenanthrene ring, and the like, but are not limited thereto.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,
Figure BDA0002831183150000042
wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rx). For example, "substituted or unsubstituted aryl" means having a substituent RxOr an unsubstituted aryl group. Wherein the above-mentioned substituent is RxFor example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl,An aryl group with 6-20 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, an alkyl group with 1-10 carbon atoms, a halogenated alkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, an alkylthio group with 1-10 carbon atoms, an aryloxy group with 6-18 carbon atoms, an arylthio group with 6-18 carbon atoms and a phosphinyloxy group with 6-18 carbon atoms, wherein the aryl group is substituted by a substituent of the tert-butyl group; when two substituents R are attached to the same atomxWhen two substituents R are presentxMay be independently present or attached to each other to form a ring with said atom; when two adjacent substituents R are present on the functional groupxWhen adjacent substituents RxMay be present independently or may be fused to form a ring with the functional group to which it is attached.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. In this specification, biphenyl, terphenyl, 9-dimethylfluorenyl are all considered aryl groups in this application. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo [9,10 ]]PhenanthrylPyrenyl, benzofluoranthenyl, pyrenyl, anthryl, pyrenyl, anthryl, pyrenyl, anthenyl, pyrenyl, anthenyl, pyrenyl, anthenyl, pyrenyl,
Figure BDA0002831183150000043
And the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25 or 30, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
Specific examples of aryl groups as substituents in the present application include, but are not limited to: phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, dimethylfluorenyl, terphenyl, diphenylfluorenyl, spirobifluorenyl.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl groups (e.g., N-phenylcarbazolyl, N- (1-naphthyl) carbazolyl, N- (2-naphthyl) carbazolyl, 9- (4-phenylphenyl) carbazolyl group), N-heteroaryl carbazolyl group (e.g., N-pyridyl carbazolyl group), N-alkyl carbazolyl group (e.g., N-methyl carbazolyl group), etc., without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The term "heteroaryl" as used herein may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be 3 to 25, in other embodiments the number of carbon atoms in the aryl group may be 12 to 24, and in other embodiments the number of carbon atoms in the aryl group may be 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
Specific examples of heteroaryl groups as substituents in the present application include, but are not limited to: dibenzothienyl, dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, indocarbazolyl, N- (1-naphthyl) carbazolyl, N- (2-naphthyl) carbazolyl, 9- (4-phenyl) carbazolyl, 9-dimethyl-9H-9-silafluorene.
In the present application, "any two adjacent RjIn a ring, "optionally adjacent" may include two R's on the same atomjIt may also include two adjacent atoms each having an Rj(ii) a Wherein when there are two R on the same atomjWhen two R are presentjMay form a saturated or unsaturated ring with the atom to which it is commonly attached; when two adjacent atoms have one R on each atomjTwo of these RjMay be fused to form a ring. Similarly, any two adjacent substituents forming a ring have the same explanation, and are not described in detail in this application.
The non-positional connection key referred to in this application
Figure BDA0002831183150000051
Refers to a single bond extending from the ring system, which means that one end of the connecting bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) includes any possible connection mode shown in the formula (f-1) to the formula (f-10).
Figure BDA0002831183150000052
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
Figure BDA0002831183150000061
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
Figure BDA0002831183150000062
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 1 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, and 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
In the present application, specific examples of the cycloalkyl group having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In one embodiment of the present application, n is1，n2、n3、n4Each independently selected from 0.
In one embodiment of the present application, said L, L1Each independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;
optionally, said L, L1Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
Specifically, the L, L1Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In another embodiment of the present application, said L, L1Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group;
in one embodiment of the present application, said L, L1Each independently selected from the group consisting of a single bond or the following groups:
Figure BDA0002831183150000063
in one embodiment of the present application, the L2Selected from a single bond, phenylene, or biphenylene.
In one embodiment of the present application, the Ar1Selected from substituted or unsubstituted aryl with 6-20 carbon atoms, substituted or unsubstituted heteroaryl with 12-20 carbon atoms;
optionally, the Ar is1Wherein the substituent is selected from deuterium, halogen group, cyano, alkyl group having 1-5 carbon atoms, aryl group having 6-14 carbon atoms, and trialkylsilyl group having 3-6 carbon atoms.
Specifically, Ar is1Substituent (1)Specific examples include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dimethylfluorenyl, phenanthryl, terphenyl, trimethylsilyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.
In the present application, optionally, Ar is1Selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
Figure BDA0002831183150000071
the substituted V has one or more substituents, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, trimethylsilyl.
In one embodiment of the present application, the Ar1Selected from the group consisting of:
Figure BDA0002831183150000072
in one embodiment of the present application, the Ar2Selected from the group consisting of substituted or unsubstituted V1Unsubstituted V1Selected from the group consisting of:
Figure BDA0002831183150000081
substituted V1V having one or more substituents, substituted1Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl.
In one embodiment of the present application, the Ar2Selected from the group consisting of substituted and unsubstitutedV2Unsubstituted V2Selected from the group consisting of:
Figure BDA0002831183150000082
Figure BDA0002831183150000091
Figure BDA0002831183150000101
Figure BDA0002831183150000111
substituted V2V having one or more substituents, substituted2Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl.
Optionally, the Ar is2Selected from the group consisting of:
Figure BDA0002831183150000112
Figure BDA0002831183150000121
in the present application, optionally, the nitrogen-containing compound is selected from the compounds shown in claim 9.
The synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present application illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the present application.
A second aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound according to the first aspect of the present application.
The nitrogen-containing compound provided by the present application can be used to form at least one organic film layer in a functional layer to improve efficiency characteristics and lifetime characteristics of an organic electroluminescent device.
In a specific embodiment, the functional layer includes an organic light-emitting layer including the nitrogen-containing compound. Generally, the organic light emitting layer may include a host material and a guest material, wherein the host material includes the nitrogen-containing compound of the present application.
In one embodiment according to the present application, the organic electroluminescent device is a green device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably comprises Indium Tin Oxide (ITO) as the active ingredientA transparent electrode which is an anode.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. The host material of the organic light emitting layer 330 may contain the nitrogen-containing compound of the present application. Further alternatively, the organic light emitting layer 330 may be composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. According to a specific embodiment, the organic electroluminescent device is a green device, wherein the organic light-emitting layer 330 may be composed of the nitrogen-containing compound provided herein; alternatively, the organic light emitting layer 330 may be composed of the nitrogen-containing compound provided herein together with other materials.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In an exemplary embodiment of the present application, the electron transport layer 340 may be composed of ET-06 and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and leadOr an alloy thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material.
In a third aspect, the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
Analytical detection of intermediates and compounds in this application uses an ICP-7700 mass spectrometer.
The method for synthesizing the nitrogen-containing compound of the present application will be specifically described below with reference to the synthesis examples.
The compounds of the present application were synthesized using the following methods
Figure BDA0002831183150000131
A reaction flask was charged with Q-1(5.0g, 19.5mmol), Q-2(6.03g, 19.5mmol), tris (dibenzylideneacetone) dipalladium (0.18g, 0.19mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.16g, 0.39mmol), sodium tert-butoxide (5.62g, 58.5mmol) and toluene solvent (50mL), heated to 110 ℃ under nitrogen, heated under reflux and stirred for 8 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane (50mL) and water (50mL) 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, the filtrate was passed through a short silica gel column after filtration, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system (1:3) to give Q-3(6.9g, 73%).
Figure BDA0002831183150000141
Respectively adding raw material IM-1(6.65g, 29.4mmol), raw material IM-2(5.0g, 23.6mmol), tetrakistriphenylphosphine palladium (1.7g, 1.47mmol), potassium carbonate (8.14g, 58.9mmol) and tetrabutylammonium chloride (0.41g, 1.47mmol) into a three-neck flask, measuring tetrahydrofuran (200mL) and water (40mL), adding into a reactor, refluxing at 80 ℃ for 12h, extracting with dichloromethane and water when the reaction is finished, collecting organic phase anhydrous MgSO4Drying, suction filtration, concentration of the organic layer and purification of the crude product on silica gel column gave M-1(7.9g, 75% yield).
M-X in Table 1 was synthesized by referring to the method of M-1 except that raw material A was used in place of raw material IM-1 and raw material B was used in place of raw material IM-2, and M-X was obtained as shown in Table 1.
TABLE 1
Figure BDA0002831183150000142
Figure BDA0002831183150000151
Figure BDA0002831183150000161
Figure BDA0002831183150000171
Figure BDA0002831183150000181
Figure BDA0002831183150000191
Synthesis of intermediate N
Figure BDA0002831183150000192
Raw material IM-17(5.0g, 20.6mmol) and N, N-dimethylformamide (50mL) were added to a reaction flask, and after cooling to 0 ℃ under a nitrogen atmosphere, sodium hydrogen (0.54g, 22.6mmol) was added, and after 30min of heat preservation, raw material IM-1(6.9g, 30.9mmol) was added, and the temperature was raised to room temperature for reaction for 2 hours. When the reaction is finished, dichloromethane and water are used for extraction, and anhydrous MgSO is taken out of an organic phase4Drying, suction filtration, concentration of the organic layer and purification of the crude product on silica gel column gave N-1(4.4g, 60% yield).
N-X in Table 2 was synthesized by referring to the method of N-1 except that raw material A was used in place of raw material IM-1 and raw material C was used in place of raw material IM-17, and N-X was obtained as shown in Table 2.
TABLE 2
Figure BDA0002831183150000201
Figure BDA0002831183150000211
Figure BDA0002831183150000221
Synthesis of intermediate B
Figure BDA0002831183150000222
To a dried and nitrogen-substituted round-bottomed flask, SM-1(5.0g,18.92mmol) and tetrahydrofuran (400mL) were added, and after cooling to-78 ℃, n-butyllithium (1.5g,22.7mmol) was added dropwise, and after completion of the addition, trimethyl borate (5.9g,56.8mmol) was added dropwise after incubation at-78 ℃ for 30min, and after completion of the addition, incubation at-78 ℃ for 30 min. Heating to room temperature, stirring for 12h, and adding hydrochloric acid aqueous solution to adjust the pH to be neutral. The resulting reaction was filtered to give the crude product, which was recrystallized from n-heptane (600mL) to give B-1(2.6g, 60%).
B-X in Table 3 was synthesized by referring to the method of B-1 except that SM-X in Table 3 was used instead of SM-1, and B-X was prepared as shown in Table 3.
TABLE 3
Figure BDA0002831183150000231
Synthesis of intermediate C:
Figure BDA0002831183150000232
respectively adding raw material M-1(5.0g, 13.97mmol), raw material J-1(2.18g, 13.97mmol), tetrakistriphenylphosphine palladium (0.08g, 0.07mmol), potassium carbonate (3.86g, 27.95mmol) and tetrabutylammonium chloride (0.02g, 0.07mmol) into a three-neck flask, measuring toluene (40mL), ethanol (20mL) and water (10mL), adding into a reactor, refluxing at 80 deg.C for 12h, extracting with dichloromethane and water when the reaction is over, collecting organic phase anhydrous MgSO4Drying, suction filtration, concentration of the organic layer and purification of the crude product on silica gel column gave C-1(4.67g, 77% yield).
C-X in Table 4 was synthesized by referring to C-1 except that M-1 was replaced with M-X/N-X as the raw material and J-1 was replaced with J-X as the raw material in Table 4, and C-X was obtained as shown in Table 4.
TABLE 4
Figure BDA0002831183150000233
Figure BDA0002831183150000241
Synthesis of Compound 1024
Figure BDA0002831183150000251
M-1(5.0g, 13.9mmol), S-1(2.9g, 13.9mmol), tetrakistriphenylphosphine palladium (0.8g, 0.69mmol), potassium carbonate (3.8g, 0.69mmol) and tetrabutylammonium chloride (0.19g, 0.69mmol) were added to a three-neck flask, toluene (40mL), ethanol (20mL) and water (10mL) were measured and added to the reactor, and the mixture was refluxed at 78 ℃ for 12 hours, and when the reaction was completed, extraction was performed using dichloromethane and water, and the organic phase was taken out of anhydrous MgSO4Drying, suction filtration, concentration of the organic layer and purification of the crude product on silica gel column gave compound 1024(4.79g, 70% yield).
Compound X in Table 5 was synthesized by referring to the procedure for Compound 1024, except that M-X/N-X as the starting material was used in place of M-1 and S-X/B-X as the starting material was used in place of S-1, and Compound X was obtained as shown in Table 5.
TABLE 5
Figure BDA0002831183150000252
Figure BDA0002831183150000261
Figure BDA0002831183150000271
Figure BDA0002831183150000281
Figure BDA0002831183150000291
Figure BDA0002831183150000301
Figure BDA0002831183150000311
Figure BDA0002831183150000321
Figure BDA0002831183150000331
Figure BDA0002831183150000341
Figure BDA0002831183150000351
Figure BDA0002831183150000361
Figure BDA0002831183150000371
Figure BDA0002831183150000381
Mass spectrometry analysis was performed on the above compounds, and the data are shown in table 6 below.
TABLE 6
Figure BDA0002831183150000382
Figure BDA0002831183150000391
The nuclear magnetic analyses of the individual compounds above were performed and the data are shown in table 7 below.
TABLE 7
Figure BDA0002831183150000392
Preparation and evaluation of organic electroluminescent device
Example 1: green organic electroluminescent device
The anode was prepared by the following procedure: the thickness of ITO is set as
Figure BDA0002831183150000393
Was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002831183150000394
And NPB is deposited on the hole injection layer to form a thickness of
Figure BDA0002831183150000395
The first hole transport layer of (1).
Vacuum evaporating a compound HTL-1 on the first hole transport layer to a thickness of
Figure BDA0002831183150000396
The second hole transport layer of (1).
On the second hole transport layer, (GH-1: compound 1024) was mixed with 8% (in proportion to the total evaporation rate of the host material) of a guest material Ir (ppy) in a ratio of (1: 1) (evaporation rate)3To perform co-evaporation to a thickness of
Figure BDA0002831183150000397
Green organic light emitting layer (EML).
ET-06 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002831183150000398
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
Figure BDA0002831183150000399
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA00028311831500003910
The cathode of (1).
The thickness of the vapor deposition on the cathode is
Figure BDA00028311831500003911
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 73
An organic electroluminescent device was fabricated by the same method as example 1, except that, in forming the organic light emitting layer, the compound 1024 was replaced with a compound shown in table 9 below.
Comparative examples 1 to 5
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C, compound D, and compound E in table 9 below were used instead of compound 1024, respectively, in forming the organic light-emitting layer.
The material structures used in the above examples and comparative examples are shown in table 8 below.
TABLE 8
Figure BDA0002831183150000401
For the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions of (1), and the results are shown in table 9 below.
TABLE 9
Figure BDA0002831183150000411
Figure BDA0002831183150000421
From the results of table 9 above, it can be seen that in examples 1 to 73 using the nitrogen-containing compound of the present application as the organic light-emitting layer, the driving voltage of the organic electroluminescent device in the present application is reduced by at least 0.19V, the luminous efficiency (Cd/a) is improved by at least 11.74%, the power efficiency (lm/W) is improved by at least 18.68%, the external quantum efficiency is improved by at least 11.73%, the lifetime is improved by at least 6.74%, and the maximum is improved by 114h, as compared with comparative examples 1 to 5 using known compounds.
The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.

Claims (12)

1. A nitrogen-containing compound, wherein the nitrogen-containing compound has the structure shown in formula I below:
Figure FDA0002831183140000011
wherein, T1Selected from O or S;
L、L1the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L2selected from single bond, substituted or unsubstituted arylene with 6-20 carbon atoms;
Ar1selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 2-30 carbon atoms;
Ar2selected from the structures shown in formula II or formula III;
wherein X, Y are independently selected from single bond, O, S, C (R)5R6) Or N (R)7) And X, Y is not a single bond at the same time;
R5、R6and R7The same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
z is selected from O, S, C (R)8R9) OrN (R)10)；
R8、R9And R10The same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
optionally, any R5And R6、R8And R9Form a saturated or unsaturated ring having 3 to 14 carbon atoms with the atoms to which they are commonly attached;
R1、R2、R3and R4The same or different, and each is independently selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 24 carbon atoms;
R1～R4with RiIs represented by n1～n4With niI is a variable, 1,2, 3 or 4, n1、n2、n3And n4Each represents R1、R2、R3And R4The number of (2);
wherein, when i is 1, n1Selected from 0, 1,2 or 3;
when i is 2, 3 or 4, n1Selected from 0, 1,2, 3 or 4;
and when n isiWhen greater than 1, any two niThe same or different;
optionally, any two adjacent RiThe benzene ring connected with the compound forms a naphthalene ring or a phenanthrene ring;
L2the substituents in (1) are selected from deuterium, halogen groups, cyano, phenyl;
L、L1、Ar1and R5～R10Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, cyano, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, a trialkylsilyl group having 3 to 12 carbon atoms, a carbogen18-24 times of triaryl silicon base, 1-10 carbon atoms of alkyl, 1-10 carbon atoms of halogenated alkyl, 3-10 carbon atoms of cycloalkyl, 2-10 carbon atoms of heterocycloalkyl, 1-10 carbon atoms of alkoxy, 1-10 carbon atoms of alkylthio, 6-18 carbon atoms of aryloxy, 6-18 carbon atoms of arylthio, 6-18 carbon atoms of phosphino.
2. The nitrogen-containing compound of claim 1, wherein said L, L1Each independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;
preferably, said L, L1Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
3. The nitrogen-containing compound of claim 1, wherein said L, L1Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group;
preferably, said L, L1Wherein the substituents are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and biphenyl.
4. The nitrogen-containing compound according to claim 1, wherein L is2Selected from a single bond, phenylene, or biphenylene.
5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1Selected from substituted or unsubstituted aryl with 6-20 carbon atoms, substituted or unsubstituted heteroaryl with 12-20 carbon atoms;
preferably, Ar is1Wherein the substituent is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 14 carbon atoms, a substituted aryl group, a substituted heteroaryl group, wherein the substituted heteroaryl group has 1 to 5 carbon atoms,A trialkylsilyl group with 3-6 carbon atoms.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1Selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
Figure FDA0002831183140000021
the substituted V has one or more substituents, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, trimethylsilyl.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar2Selected from the group consisting of substituted or unsubstituted V1Radical, unsubstituted V1Selected from the group consisting of:
Figure FDA0002831183140000022
Figure FDA0002831183140000031
substituted V1V having one or more substituents, substituted1Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl.
8. The nitrogen-containing compound according to claim 1, wherein Ar is at least one member selected from the group consisting of2Selected from the group consisting of substituted or unsubstituted V2Radical, unsubstituted V2Is selected from the group consisting ofThe group consisting of:
Figure FDA0002831183140000032
Figure FDA0002831183140000041
Figure FDA0002831183140000051
substituted V2V having one or more substituents, substituted2Each substituent of (a) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl.
9. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0002831183140000052
Figure FDA0002831183140000061
Figure FDA0002831183140000071
Figure FDA0002831183140000081
Figure FDA0002831183140000091
Figure FDA0002831183140000101
Figure FDA0002831183140000111
Figure FDA0002831183140000121
Figure FDA0002831183140000131
Figure FDA0002831183140000141
Figure FDA0002831183140000151
Figure FDA0002831183140000161
Figure FDA0002831183140000171
Figure FDA0002831183140000181
Figure FDA0002831183140000191
Figure FDA0002831183140000201
Figure FDA0002831183140000211
Figure FDA0002831183140000221
Figure FDA0002831183140000231
Figure FDA0002831183140000241
Figure FDA0002831183140000251
Figure FDA0002831183140000261
Figure FDA0002831183140000271
Figure FDA0002831183140000281
Figure FDA0002831183140000291
Figure FDA0002831183140000301
Figure FDA0002831183140000311
Figure FDA0002831183140000321
Figure FDA0002831183140000331
Figure FDA0002831183140000341
Figure FDA0002831183140000351
Figure FDA0002831183140000361
Figure FDA0002831183140000371
Figure FDA0002831183140000381
Figure FDA0002831183140000391
Figure FDA0002831183140000401
Figure FDA0002831183140000411
Figure FDA0002831183140000421
Figure FDA0002831183140000431
Figure FDA0002831183140000441
Figure FDA0002831183140000451
Figure FDA0002831183140000461
Figure FDA0002831183140000471
Figure FDA0002831183140000481
Figure FDA0002831183140000491
Figure FDA0002831183140000501
10. an electronic component comprising an anode and a cathode which are disposed opposite to each other, and a functional layer interposed between the anode and the cathode, the functional layer containing the nitrogen-containing compound according to any one of claims 1 to 9;
preferably, the functional layer includes an organic light emitting layer including the nitrogen-containing compound;
more preferably, the organic light-emitting layer includes a host material and a guest material, and the host material includes the nitrogen-containing compound.
11. The electronic component according to claim 10, wherein the electronic component is an organic electroluminescent device;
preferably, the organic electroluminescent device is a green organic electroluminescent device.
12. An electronic device comprising the electronic component according to claim 10 or 11.
CN202011460044.4A 2020-12-11 2020-12-11 Nitrogen-containing compound, and electronic element and electronic device using same Active CN113651826B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202011460044.4A CN113651826B (en) 2020-12-11 2020-12-11 Nitrogen-containing compound, and electronic element and electronic device using same
PCT/CN2021/130172 WO2022121618A1 (en) 2020-12-11 2021-11-11 Nitrogen-containing compound, and electronic component and electronic apparatus using same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202011460044.4A CN113651826B (en) 2020-12-11 2020-12-11 Nitrogen-containing compound, and electronic element and electronic device using same

Publications (2)

Publication Number Publication Date
CN113651826A true CN113651826A (en) 2021-11-16
CN113651826B CN113651826B (en) 2023-07-25

Family

ID=78476833

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202011460044.4A Active CN113651826B (en) 2020-12-11 2020-12-11 Nitrogen-containing compound, and electronic element and electronic device using same

Country Status (2)

Country Link
CN (1) CN113651826B (en)
WO (1) WO2022121618A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022121618A1 (en) * 2020-12-11 2022-06-16 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic component and electronic apparatus using same
WO2023121062A1 (en) * 2021-12-22 2023-06-29 주식회사 엘지화학 Novel compound and organic light emitting device comprising same
WO2024060739A1 (en) * 2022-09-21 2024-03-28 陕西莱特光电材料股份有限公司 Organic compound, electronic element comprising same, and electronic device

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117683047A (en) * 2022-08-22 2024-03-12 陕西莱特光电材料股份有限公司 Organic compound, organic electroluminescent device and electronic apparatus
CN117412652A (en) * 2022-10-09 2024-01-16 陕西莱特光电材料股份有限公司 Organic electroluminescent device and electronic device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106977497A (en) * 2016-01-18 2017-07-25 Sfc有限责任公司 Organic luminescent compounds and the organic light emitting apparatus comprising it
CN110642835A (en) * 2018-06-26 2020-01-03 三星电子株式会社 Condensed ring compound and organic light emitting device including the same
CN113637006A (en) * 2020-05-11 2021-11-12 三星显示有限公司 Compound, light-emitting device including the same, and electronic device
CN114075176A (en) * 2020-11-10 2022-02-22 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN115244057A (en) * 2020-04-14 2022-10-25 株式会社Lg化学 Novel compound and organic light emitting device comprising the same

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20200001439A (en) * 2018-06-26 2020-01-06 삼성전자주식회사 Condensed cyclic compound and organic light emitting device comprising the same
CN109912610B (en) * 2019-04-04 2020-06-23 石家庄诚志永华显示材料有限公司 Organic compound and application thereof in preparation of organic electroluminescent element
CN111471452A (en) * 2019-11-01 2020-07-31 吉林奥来德光电材料股份有限公司 Organic light-emitting compound, preparation method thereof and organic electroluminescent device
KR102398015B1 (en) * 2020-04-14 2022-05-16 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
CN113651826B (en) * 2020-12-11 2023-07-25 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic element and electronic device using same
CN112679511B (en) * 2020-12-14 2022-04-22 阜阳欣奕华材料科技有限公司 Organic electroluminescent material and application thereof
CN113788847B (en) * 2021-08-24 2023-11-03 陕西莱特迈思光电材料有限公司 Organic compound, and electronic component and electronic device using same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106977497A (en) * 2016-01-18 2017-07-25 Sfc有限责任公司 Organic luminescent compounds and the organic light emitting apparatus comprising it
CN110642835A (en) * 2018-06-26 2020-01-03 三星电子株式会社 Condensed ring compound and organic light emitting device including the same
CN115244057A (en) * 2020-04-14 2022-10-25 株式会社Lg化学 Novel compound and organic light emitting device comprising the same
CN113637006A (en) * 2020-05-11 2021-11-12 三星显示有限公司 Compound, light-emitting device including the same, and electronic device
CN114075176A (en) * 2020-11-10 2022-02-22 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022121618A1 (en) * 2020-12-11 2022-06-16 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic component and electronic apparatus using same
WO2023121062A1 (en) * 2021-12-22 2023-06-29 주식회사 엘지화학 Novel compound and organic light emitting device comprising same
WO2024060739A1 (en) * 2022-09-21 2024-03-28 陕西莱特光电材料股份有限公司 Organic compound, electronic element comprising same, and electronic device

Also Published As

Publication number Publication date
WO2022121618A1 (en) 2022-06-16
CN113651826B (en) 2023-07-25

Similar Documents

Publication Publication Date Title
CN113861100B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN111777517B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN113501800B (en) Organic electroluminescent material, electronic element and electronic device
CN112300055B (en) Nitrogen-containing compound, electronic component, and electronic device
CN113651826B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN112079730B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN113683603B (en) Organic compound, electronic device comprising organic compound and electronic device comprising organic compound
CN112830889B (en) Nitrogen-containing compound, electronic component, and electronic device
CN112759582B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN113233987B (en) Nitrogen-containing compound, electronic element comprising same and electronic device
CN112142674B (en) Organic compound, and electronic element and electronic device using same
CN113121408B (en) Nitrogen-containing compound, electronic component, and electronic device
CN115784904B (en) Nitrogen-containing compound, electronic component and electronic device
CN113321589B (en) Nitrogen-containing compound, electronic component, and electronic device
CN114057705B (en) Nitrogen-containing compound, and electronic element and electronic device comprising same
CN113651703B (en) Organic compound, electronic component, and electronic device
CN114133351B (en) Nitrogen-containing compound, and electronic component and electronic device comprising same
CN114933571A (en) Organic compound, electronic element, and electronic device
CN114920750A (en) Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN115197125B (en) Organic compound, and electronic component and electronic device using same
CN115650899B (en) Nitrogen-containing compound, electronic component and electronic device
CN113666832B (en) Organic compound, and electronic element and electronic device using same
CN114736198B (en) Organic compound, and electronic element and electronic device using same
CN115521214B (en) Organic compound, and electronic component and electronic device including the same
CN117603220A (en) Organic compound, organic electroluminescent device and electronic device

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
GR01 Patent grant
GR01 Patent grant