CN114181095B - Arylamine compound and organic electroluminescent element containing the same - Google Patents

Arylamine compound and organic electroluminescent element containing the same Download PDF

Info

Publication number
CN114181095B
CN114181095B CN202111581185.6A CN202111581185A CN114181095B CN 114181095 B CN114181095 B CN 114181095B CN 202111581185 A CN202111581185 A CN 202111581185A CN 114181095 B CN114181095 B CN 114181095B
Authority
CN
China
Prior art keywords
layer
organic electroluminescent
compound
substituted
unsubstituted
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.)
Active
Application number
CN202111581185.6A
Other languages
Chinese (zh)
Other versions
CN114181095A (en
Inventor
董焕章
朱波
徐先锋
王振宇
李利铮
李程辉
刘赛赛
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.)
Shanghai 800 Million Spacetime Advanced Material Co ltd
Original Assignee
Shanghai 800 Million Spacetime Advanced 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 Shanghai 800 Million Spacetime Advanced Material Co ltd filed Critical Shanghai 800 Million Spacetime Advanced Material Co ltd
Priority to CN202111581185.6A priority Critical patent/CN114181095B/en
Publication of CN114181095A publication Critical patent/CN114181095A/en
Application granted granted Critical
Publication of CN114181095B publication Critical patent/CN114181095B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/72—Heterocyclic compounds containing 1,3,5-triazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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
    • 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
    • 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
    • C09K2211/1018—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
    • C09K2211/1059—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

Landscapes

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

Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to an arylamine compound shown in a formula I and an organic electroluminescent element containing the arylamine compound. The compound shown in the formula I provided by the invention increases the rigidity and the conjugate strength of aryl amine molecules, improves the thermal stability of materials and the capability of carrier transportation, and can obviously reduce the driving voltage and improve the luminous efficiency and the service life when being applied to organic electroluminescent elements.

Description

Arylamine compound and organic electroluminescent element containing the same
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to preparation of an aryl amine compound and application of the aryl amine compound in an organic electroluminescent element.
Background
In general, an organic light emitting phenomenon refers to a phenomenon that emits light when electric energy is applied to an organic substance. That is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, the organic electroluminescent display technology has tended to mature, and some products have entered the market, but in the industrialization time, many problems still need to be solved. In particular, various organic materials for manufacturing devices, which have carrier injection and transport properties, material electroluminescence properties, service life, color purity, matching between various materials and between various electrodes, and the like, have not been solved. Especially, the light emitting element has not reached practical requirements in light emitting efficiency and service life, which greatly limits the development of OLED technology. While the metal complex phosphorescent material using triplet light emission has high light emission efficiency, green and red light materials thereof have reached the use requirements, the metal complex phosphorescent material requires a phosphorescent material or a hole material having a high triplet energy level to match with, and thus, development of a phosphorescent material or a hole material having a high triplet energy level is an urgent need for the current development of OLEDs.
Under current technological development, improvements are still needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent elements and in terms of thermal stability during sublimation.
In order to overcome the above-described problems of the conventional techniques and to further improve the characteristics of the organic electroluminescent device, development of a more stable and effective substance that can be used as a phosphorescent material or a hole material in the organic electroluminescent device is continuously demanded.
Disclosure of Invention
The object of the present invention is to provide an arylamine compound.
It is another object of the present invention to provide an organic electroluminescent material comprising the above arylamine compound.
It is still another object of the present invention to provide an organic electroluminescent element, and use of the above arylamine compound for preparing an organic electroluminescent element.
In order to achieve the above purpose, the invention adopts the following technical scheme:
an arylamine compound has a structural formula shown in a formula I:
wherein:
l is selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene of (2), or substituted or unsubstituted C 2 -C 60 Is a heteroarylene group;
R 1 ～R 11 each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylvinyl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group in which two or more adjacent substituents may optionally be joined or fused to form another one or more substituted or unsubstituted rings, inThe resulting ring may or may not contain one or more heteroatoms N, P, B, O or S; preferably, R 1 ～R 11 Is hydrogen;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
n is selected from integers from 0 to 5, preferably n is selected from integers from 0 to 2.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
Preferably, said L is selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene of (2), or substituted or unsubstituted C 2 -C 60 Is a heteroarylene group.
Preferably, said R 1 ～R 11 Hydrogen or deuterium.
Preferably, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group.
Preferably, n is selected from 0, 1 or 2.
Preferably, in the above arylamine compound, the C 2 -C 60 The heteroaryl group is selected from the group consisting of the groups shown in the following II-1 to II-17:
wherein,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, and hydrazineA group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Naphthene radical, C 3 -C 60 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 represent O, S, CR 'R "or NAr';
r ', R' are each independently selected from hydrogen, deuterium, C 1 ～C 60 Alkyl, C of (2) 1 ～C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl, R' and R "may optionally be joined or fused to form another one or more substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 60 Alkyl, C of (2) 1 ～C 60 Heteroalkyl of (C) 3 ～C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl or naphthyl;
represents the bond between the substituent and the main structure.
Preferably, in the above compound, L is selected from a single bond or a group consisting of groups represented by the following III-1 to III-15:
wherein,
Z 11 and Z 12 Each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Naphthene radical, C 3 -C 60 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 One or more of the heterocyclic aryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 2 represent O, S, CR 'R "or NAr';
r ', R' are each independently selected from hydrogen, deuterium, C 1 ～C 60 Alkyl, C of (2) 1 ～C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl, R' and R "may optionally be joined or fused to form another one or more substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 60 Alkyl, C of (2) 1 ～C 60 Heteroalkyl of (C) 3 ～C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl or naphthyl;
represents the bond between the substituent and the main structure.
C according to the invention 6 -C 60 Aryl refers in particular to groups derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzine, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isopolyindene, spiropolyindene, spiroisopolyindene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ]]Quinoline, benzo [6,7]Quinoline, benzo [7,8]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoImidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazabenzophenanthrene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4, 5-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorored, naphthyridine, azacarbazole, benzocarboline, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 5-tetrazine, 1,2, 5-tetrazine, purine, pteridine, indolizine, quinazoline and benzothiadiazole, or a combination of groups derived from these.
In the present specification, the term "substituted or unsubstituted" means that the compound is selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, and C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkyl, C 3 -C 60 Cycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Aryl sulfide group and C 2 -C 60 More than 1 substituent in the heterocyclic aryl group is substituted or unsubstituted, or a substituent which is formed by connecting more than 2 substituents in the above exemplified substituents is substituted or unsubstituted.
Preferably, the compound is a group consisting of CJHM383 to CJHM 548:
wherein-T 3 -O-, S-, or one of the following structures:
* -and- (x) represents a bond.
The invention also provides a material, wherein the material comprises the compound organic electroluminescent material, and preferably the material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a luminescent layer material, an electron transport layer material, an electron injection layer material, a CPL material or an electron blocking layer material. Materials comprising the compounds of the present invention have the ability to transport carriers or the ability to extract light.
The present invention also provides an organic electroluminescent element comprising a first electrode, a second electrode, a CPL layer, and one or more organic layers interposed between the first electrode and the second electrode; the material of at least one of the organic layer or the CPL comprises the compound described above.
The organic electroluminescent element comprises a cathode, an anode, CPL and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent element described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-transport layer and in the light-emitting layer and in the CPL, all materials can be used in the manner customary in accordance with the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Also preferred are organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula I. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of preparations of the compounds of the invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or mixtures of these solvents.
Preferably, in the above organic electroluminescent element, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, a CPL layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
The invention also provides application of the compound in preparing an organic electroluminescent element.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The beneficial effects obtained by the invention are as follows:
the aromatic amine compound shown in the formula I provided by the invention increases the rigidity of triarylamine, has high triplet energy level, improves the thermal stability of the material and the capability of transporting carriers, and can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life when being applied to an organic electroluminescent element.
Drawings
FIG. 1 is a schematic diagram of a CPL-containing layer of an organic electroluminescent device of the present invention;
FIG. 2 is a schematic view of an organic electroluminescent element of the present invention without a hole blocking layer;
FIG. 3 is a schematic representation of the molecular structure of CJHM 384;
FIG. 4 is a schematic diagram of the molecular structure of B-1;
FIG. 5 is a schematic diagram of the molecular structure of B-2;
FIG. 6 is a schematic diagram of the molecular structure of B-3;
FIG. 7 is a schematic diagram of the molecular structure of B-4.
Reference numerals
In fig. 1, 100 denotes an organic electroluminescent element, 101 denotes a substrate, 102 denotes an anode layer, 103 denotes a hole injection layer, 104 denotes a hole transport layer, 105 denotes an electron blocking layer, 106 denotes a light emitting layer, 107 denotes a hole blocking layer, 108 denotes an electron transport layer, 109 denotes an electron injection layer, 110 denotes a cathode layer, and 111 denotes a CPL layer.
In fig. 2, 200 is an organic electroluminescent element, 101 is a substrate, 102 is an anode layer, 103 is a hole injection layer, 104 is a hole transport layer, 105 is an electron blocking layer, 106 is a light emitting layer, 107 is an electron transport layer, 108 is an electron injection layer, 109 is a cathode layer, and 110 is a CPL layer.
Detailed Description
The present invention is described in further detail below with reference to specific examples, but is not intended to limit the scope of the present invention.
In the description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower", etc. are based on the orientation or positional relationship shown in the drawings, are merely for convenience of description and to simplify the description, and are not indicative or implying that the apparatus or elements in question must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the present invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the examples below, unless otherwise specified, are all commercially available, and the percentages, such as the percentages without otherwise specified, are all mass percentages.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT 1931-C test was used.
Examples
The synthetic route for the compounds of formula I is as follows:
wherein X represents I, br, cl or OTf; the other symbols used are as defined above.
Example 1
The preparation method of the compound C-1 comprises the following steps:
the first step: preparation of intermediate Int-1
25.0mmol of 1, 8-dibromonaphthalene, 27.5mmol of 2-aldehyde phenylboronic acid pinacol ester, 75.0mmol of anhydrous sodium carbonate are dissolved in a mixture comprising 100mL of toluene, 50mL of ethanol and 50mL of water, and 2.5mmol of tetrabutylammonium bromide and 0.25mmol of Pd (PPh 3 ) 4 The catalyst is heated, refluxed and stirred for reaction for 12 hours, 100mL of water is added, an organic phase is collected, the water phase is extracted by ethyl acetate, the organic phase is dried and filtered, the filtrate is concentrated to dryness under reduced pressure, and then the yellow solid Int-1 is obtained after separation and purification by a silica gel column, and the yield is 86%.
And a second step of: preparation of intermediate Int-2
Under the protection of nitrogen, 30.0mmol of methoxymethyl triphenylphosphine chloride is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃, 36.0mmol of potassium tert-butoxide is added in portions, stirring reaction is carried out for 1 hour, 20.0mmol of Int-1 solution dissolved in 30mL of THF is added dropwise, stirring reaction is carried out for 1 hour, heating is carried out to reflux stirring reaction for 2 hours, cooling to room temperature, 100mL of saturated saline solution is added, extraction is carried out by ethyl acetate, an organic phase is dried, filtered, concentrated to dryness under reduced pressure, and separation and purification are carried out by a silica gel column to obtain white solid Int-2, yield: 82%.
And a third step of: preparation of Compound C-1
50.0mmol of intermediate Int-2, 10.0mmol of methanesulfonic acid and 120mL of dichloromethane are mixed under the protection of nitrogen, stirred at room temperature for reaction for 2 hours, heated to reflux, stirred for reaction for 1 hour, cooled to room temperature, washed with 1M aqueous sodium hydroxide solution, dried, concentrated under reduced pressure to dryness, and separated and purified by a silica gel column to obtain the compound C-1 with the yield of 93 percent. GC-MS, m/z:306.0, 307.0, 308.0[ M ] + ]。
Example 2
Preparation of compound CJHM 384:
40.0mmol of C-1 was dissolved in 80mL of toluene and 48.0mmol of di ([ 1,1' -biphenyl) was added under nitrogen protection]-4-yl) amine, 60.0mmol sodium tert-butoxide, 0.2mmol Pd 2 (dba) 3 The catalyst and 0.4mmol of XanPhos are heated to 100 ℃, stirred and reacted for 12 hours, cooled to room temperature, 20mL of water is added, stirred and reacted for 1 hour, the organic phase is extracted with dichloromethane, collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain yellow solid CJHM384, HPLC:99.92%, yield: 85%, MS (MALDI-TOF): m/z=548.2388 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.85～8.83(1H,d)；8.15～8.13(2H,d)；7.97～7.82(4H,m)；7.62～7.58(4H,m)；7.51～7.35(9H,m)；7.25～7.21(4H,m)；7.18～7.11(5H,m)。
Referring to the above synthetic method, the following compounds were prepared:
example 3
A process for the preparation of compound CJHM536 comprising the steps of:
the first step: preparation of Compound Int-4
20.0mmol of C-1 are dissolved in 50mL of DMF and under the protection of nitrogen, 24.0mmol of bisboronic acid pinacol ester, 30.0mmol of anhydrous potassium acetate and 0.1mmol of PdCl are added 2 (dppf) catalyst, 2.0mmol of cuprous iodide, heating to 100 ℃, stirring and reacting for 12 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, drying, separating and purifying with a silica gel column to obtain yellow solid Int-4, wherein the yield is 87%.
And a second step of: preparation of Compound CJHM536
12.0mmol of Int-4 was dissolved in 40mL of toluene and under nitrogen protection 10.0mmol of SM1, 36.0mmol of anhydrous sodium carbonate, 0.1mmol of Pd (PPh) 3 ) 4 The catalyst is added with 20mL of ethanol and 20mL of water, the temperature is raised to reflux and the mixture is stirred for reaction for 10 hours, the mixture is cooled to room temperature, 50mL of water is added for dilution, the mixture is extracted with ethyl acetate, an organic phase is collected, dried, filtered, and the filtrate is concentrated to dryness under reduced pressure, and is separated and purified by a silica gel column to obtain yellow solid CJHM536, the yield is 88%, and after vacuum sublimation, HPLC:99.96%, MS (MALDI-TOF): m/z=625.2406 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.98～8.96(1H,d)；8.87～8.85(1H,d)；8.59～7.52(4H,m)；8.44～8.42(1H,d)；8.30～8.28(1H,d)；8.21～8.06(5H,m)；7.93～7.82(4H,m)；7.58～7.48(2H,m)；7.46～7.35(9H,m)。
Referring to the above synthetic method, the following compounds were prepared:
example 4
An organic electroluminescent device 200, as shown in fig. 2, having a structure including a substrate 101, an anode layer 102 provided on the substrate 101, a hole injection layer 103 provided on the anode layer 102, a hole transport layer 104 provided on the hole injection layer 103, an electron blocking layer 105 provided on the hole transport layer 104, a light emitting layer 106 provided on the electron blocking layer 105, an electron transport layer 107 provided on the light emitting layer 106, an electron injection layer 108 provided on the electron transport layer 107, a cathode layer 109 provided on the electron injection layer 108, and a CPL layer 110 provided on the cathode layer, is prepared by the steps of:
the compound prepared in the embodiment is subjected to vacuum sublimation purification to prepare a material with HPLC content more than or equal to 99.95 percent, which is used for preparing an organic electroluminescent element,
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, depositing metallic aluminum as an anode layer on the ITO film, the thickness of the deposited film beingVapor deposition compound 2-TNATA as hole injection layer, vapor deposition film thickness of +.>
3) The compound shown in the formula I is continuously evaporated on the hole injection layer to form a hole transport layer, and the thickness of the evaporated film is
4) Continuing to vapor deposit the compound shown in the formula I as an electron blocking layer on the hole injection layer, wherein the vapor deposition film thickness is as follows
5) Continuously evaporating mCBP as a main material and GD976 (UDC) as a doping material on the electron blocking layer, wherein the mass ratio of mCBP to GD976 is 95:5, and the film thickness of the evaporation film is equal to that of the organic light-emitting layer
6) Continuously evaporating a layer of LiQ and ET186 serving as electron transport layers on the organic light-emitting layer, wherein the mass ratio of the LiQ to the ET186 is 50:50, and the evaporating film thickness is
7) Continuously evaporating a LiF layer on the electron transport layer to form an electron injection layer with an evaporating film thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer, wherein the mass ratio of magnesium to silver is 1:2, and the film thickness of the evaporated film is
9) Evaporating an NPB CPL layer as element on the transparent cathode layer to obtain an evaporation film with a thickness ofThe OLED element provided by the invention is obtained.
Example 5
An organic electroluminescent device 100 has a structure as shown in fig. 1, and includes a substrate 101, an anode layer 102 provided on the substrate 101, a hole injection layer 103 provided on the anode layer 102, a hole transport layer 104 provided on the hole injection layer 103, an electron blocking layer 105 provided on the hole transport layer 104, a light emitting layer 106 provided on the electron blocking layer 105, a hole blocking layer 107 provided on the light emitting layer 106, an electron transport layer 108 provided on the hole blocking layer 107, an electron injection layer 109 provided on the electron transport layer 108, a cathode layer 110 provided on the electron injection layer 109, and a CPL layer 111 provided on the cathode layer 110.
Comparative example 1
By following the same procedure as in example 4, the compound of formula I in steps 3) and 4) was replaced with B-1 to give comparative element 1;
comparative example 2
By following the same procedure as in example 4, the compound of formula I in steps 3) and 4) was replaced with B-2 to give comparative element 2;
comparative example 3
By following the same procedure as in example 4, the compound of formula I in steps 3) and 4) was replaced with B-3 to give comparative element 3;
the results of the performance measurements of the resulting devices are shown in Table 1, wherein the driving voltage, luminance efficiency, color coordinates (1931 CIE) and full width at half maximum (FWHM) are at a current density of 10mA/cm for the devices 2 Under the conditions, the LT95% lifetime of the element was found to be 2000cd/m at the initial luminance 2 Is measured under the condition of (2).
TABLE 1 results of component Performance test
As can be seen from Table 1, the light-emitting element prepared from the organic material of the present invention as a hole transport material and an electron blocking material has significantly reduced driving voltage compared with B-1, B-2, and B-3 under the same current density, significantly improved luminance efficiency, and at 2000cd/m 2 The LT95% lifetime under the initial brightness condition of (a) has obvious advantages, probably because the molecules of B-1, B-2, B-3 and B-4 are closer to a plane configuration, a disordered film layer is formed during vacuum high-temperature coating, the compound shown in the formula I is distorted to form a three-dimensional structure with irregular rigidity, a regular laminated film layer is easy to form, and therefore, the compound is more beneficial to the transmission of carriers, the compound takes CJHM384 as an example through software Gaussian16 calculation (B3 LYP/6-31 (d)), the dihedral angle after the mother nucleus is distorted is 29.66 degrees, the dihedral angle of the mother nucleus of B-1 is 8.94 degrees, the dihedral angle of the mother nucleus of B-2 is 8.01 degrees, the dihedral angle of the mother nucleus of B-3 is 8.28 degrees, the dihedral angle of the mother nucleus of B-4 is 8.60 degrees, and the optimized structure is shown in fig. 3-7.
Comparative example 4
Following the same procedure as in example 4, the compound of formula I in step 3) was replaced with CJHM402 (T 3 :CMe 2 ) Replacing the compound of formula I in step 4) with CJHM402 (T) 3 :CMe 2 ) Replacing NPB in the step 9) with B-4 to obtain a comparison element 4;
comparative example 5
Following the same procedure as in example 4, the compound of formula I in step 3) was replaced with CJHM402 (T 3 :CMe 2 ) Replacing the compound of formula I in step 4) with CJHM402 (T) 3 :CMe 2 ) Obtaining a contrast element 5;
example 6
Following the same procedure as in example 4, the compound of formula I in step 3) was replaced with CJHM402 (T 3 :CMe 2 ) Replacing the compound of formula I in step 4) with CJHM402 (T) 3 :CMe 2 ) And 9) replacing NPB in the step 9) with the compound shown in the formula I, so as to obtain the OLED element provided by the invention.
The results of the performance measurements of the resulting devices are shown in Table 2, wherein the luminance efficiency, color coordinates (1931 CIE) and full width at half maximum (FWHM) are at a current density of 10mA/cm for the devices 2 Under the conditions, the LT95% lifetime of the element was found to be 2000cd/m at the initial luminance 2 Is measured under the condition of (2).
TABLE 2 results of component Performance test
In the above tables 1 and 2, Q-0 to Q-3, W-0 to W-3, G-0 to G-4, K-0 to K-4 represent the following groups:
as can be seen from the above, the luminance efficiency of the element prepared from the compound of the present invention as CPL material is significantly higher than that of NPB and B-4 under the same current density condition, and is 2000cd/m 2 The LT95% lifetime of the element at the initial brightness condition is multiplied compared to a device using NPB and B-4.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (6)

1. An arylamine compound characterized by a structural formula selected from the group consisting of CJHM383 to CJHM 548:
wherein-T 3 -O-, S-, or one of the following structures:
* -and- (x) represents a bond.
2. An organic electroluminescent material, characterized in that a raw material of the organic electroluminescent material comprises the compound according to claim 1.
3. An organic electroluminescent element comprising a first electrode, a second electrode, a CPL layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layer or the CPL comprises the compound of claim 1.
4. The organic electroluminescent element according to claim 3, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a CPL layer, or an electron blocking layer.
5. Use of a compound according to claim 1 in an organic electroluminescent element, characterized in that the compound is used for a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a CPL layer or an electron blocking layer of the organic electroluminescent element.
6. A consumer product comprising an organic electroluminescent element, the organic electroluminescent element comprising: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a compound comprising a compound of formula 1.
CN202111581185.6A 2021-12-22 2021-12-22 Arylamine compound and organic electroluminescent element containing the same Active CN114181095B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111581185.6A CN114181095B (en) 2021-12-22 2021-12-22 Arylamine compound and organic electroluminescent element containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111581185.6A CN114181095B (en) 2021-12-22 2021-12-22 Arylamine compound and organic electroluminescent element containing the same

Publications (2)

Publication Number Publication Date
CN114181095A CN114181095A (en) 2022-03-15
CN114181095B true CN114181095B (en) 2024-01-12

Family

ID=80544745

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111581185.6A Active CN114181095B (en) 2021-12-22 2021-12-22 Arylamine compound and organic electroluminescent element containing the same

Country Status (1)

Country Link
CN (1) CN114181095B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114605314B (en) * 2022-03-30 2024-04-02 上海八亿时空先进材料有限公司 Indene derivative and application thereof
CN114621133B (en) * 2022-04-02 2024-04-02 上海八亿时空先进材料有限公司 Organic compound, organic electroluminescent material and light-emitting element
CN117700399A (en) * 2022-09-07 2024-03-15 陕西莱特光电材料股份有限公司 Triazine-containing compound, organic electroluminescent device, and electronic device

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012512243A (en) * 2008-12-18 2012-05-31 東友ファインケム株式会社 Arylamine derivative for organic electroluminescent device having asymmetric structure, method for producing the same, organic thin film material for organic electroluminescent device including the same, and organic electroluminescent device using the same
CN109970575A (en) * 2019-04-22 2019-07-05 吉林奥来德光电材料股份有限公司 Organic electroluminescent compounds and its preparation method and application
CN113429348A (en) * 2021-08-27 2021-09-24 北京八亿时空液晶科技股份有限公司 Anthracene imidazole derivative, organic electroluminescent material and consumer product

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012512243A (en) * 2008-12-18 2012-05-31 東友ファインケム株式会社 Arylamine derivative for organic electroluminescent device having asymmetric structure, method for producing the same, organic thin film material for organic electroluminescent device including the same, and organic electroluminescent device using the same
CN109970575A (en) * 2019-04-22 2019-07-05 吉林奥来德光电材料股份有限公司 Organic electroluminescent compounds and its preparation method and application
CN113429348A (en) * 2021-08-27 2021-09-24 北京八亿时空液晶科技股份有限公司 Anthracene imidazole derivative, organic electroluminescent material and consumer product

Also Published As

Publication number Publication date
CN114181095A (en) 2022-03-15

Similar Documents

Publication Publication Date Title
CN114181095B (en) Arylamine compound and organic electroluminescent element containing the same
CN115109039B (en) Carbazole derivative and application thereof in OLED
CN115073461B (en) Carbazole derivative and application thereof in organic light-emitting element
CN113429395A (en) Imidazole derivative, organic electroluminescent material, light-emitting element, and consumer product
CN115093414B (en) Carbazole derivative and organic light-emitting element comprising same
CN113912471B (en) Anthracene derivative, organic electroluminescent material, light-emitting device and consumer product
CN115304497B (en) Fluorene derivative containing homotriptycene and application thereof
CN114890996B (en) Heterocyclic compound and organic light-emitting element comprising same
CN115124433B (en) Spirobifluorene derivative and application thereof
CN114539075B (en) Fluorene derivative and application thereof
CN114957226B (en) Phenanthridine derivative and application thereof
CN114907394A (en) Silafluorene derivative and organic electroluminescent element containing same
CN114957094A (en) Polysubstituted carbazole derivative and application thereof
CN115322177A (en) Fluorene derivative and application thereof
CN114890959A (en) Fluoranthene derivative and application thereof
CN115028630B (en) Azaadamantane compound and organic electroluminescent element
CN114605411B (en) Acridine derivative and application thereof
CN114605314B (en) Indene derivative and application thereof
WO2023082808A1 (en) Tetraaza-fluoranthene compound and application thereof
CN115073306A (en) Acenaphthene derivative and organic electroluminescent element containing same
CN113429348B (en) Anthracene imidazole derivative, organic electroluminescent material and consumer product
CN116354833A (en) High triptycene derivative and application thereof
CN114907179A (en) Anthracene derivative, and organic electroluminescent material, light-emitting device and consumer product using the same
CN114456167A (en) Azafluoranthene derivative and application thereof
CN114437095A (en) Heterocyclic compound, organic electroluminescent material and 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