CN116063187A - Compound and application thereof in organic photoelectric device - Google Patents

Compound and application thereof in organic photoelectric device Download PDF

Info

Publication number
CN116063187A
CN116063187A CN202211333272.4A CN202211333272A CN116063187A CN 116063187 A CN116063187 A CN 116063187A CN 202211333272 A CN202211333272 A CN 202211333272A CN 116063187 A CN116063187 A CN 116063187A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
organic
compound
independently selected
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.)
Pending
Application number
CN202211333272.4A
Other languages
Chinese (zh)
Inventor
王鹏
王湘成
何睦
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 Yaoyi Electronic Technology Co ltd
Original Assignee
Shanghai Yaoyi Electronic Technology 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 Yaoyi Electronic Technology Co ltd filed Critical Shanghai Yaoyi Electronic Technology Co ltd
Priority to CN202211333272.4A priority Critical patent/CN116063187A/en
Publication of CN116063187A publication Critical patent/CN116063187A/en
Pending legal-status Critical Current

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
    • C07C211/54—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 two or three six-membered aromatic rings
    • 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
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • 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
    • C07C211/60—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 containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • 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
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • 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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • 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
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—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
    • C09K2211/1088—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)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention discloses a compound and application thereof in an organic photoelectric device, the compound has a structure shown as a formula (1), L 1 ‑L 3 Independently selected from a single bond, a substituted or unsubstituted C6-C30 aryl or C5-C30 heteroaryl group; a is that 1 ‑A 3 Independently selected from a single bond, a substituted or unsubstituted chain alkylene or branched chain alkylene, cycloalkylene or heterocycloalkylene, alkylimine, alkylene ether, alkylene sulfide, arylene, heteroarylene, arylimine, arylene ether, arylene sulfide, heteroarylimine, heteroarylene ether, heteroarylene sulfide; ar (Ar) 1 ‑Ar 3 Independently selected from a substituted or unsubstituted C6-C30 aryl or C5-C30 heteroaryl group, and at least one selected from the group represented by formula (2). The compound provided by the invention can be used as a hole transport material of an OLED device, so that the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Description

Compound and application thereof in organic photoelectric device
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to a compound and application thereof in an organic photoelectric device.
Background
An organic electroluminescent (OLED) device is a device having a sandwich-like structure, including positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. At present, the technology is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with rapid development and high technical requirements.
Common functionalized organic materials used in OLED devices include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light emitting host materials, light emitting guests (dyes), and the like. Based on this, the field of OLED materials has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device. The development of the existing OLED photoelectric functional material is far behind the performance requirement of panel manufacturing enterprises on the OLED material so far, so that the development of the organic functional material with better performance is particularly urgent to meet the current industrial development requirement.
At present, the hole transport material mainly adopts an aromatic amine compound with good hole transport property, and N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) is widely applied to organic electroluminescent devices with various colors due to moderate highest occupied orbit energy level and good hole mobility. However, the glass transition temperature of the molecules is low (98 ℃), and the devices are easy to change phase under the action of accumulated joule heat when the devices are operated for a long time, so that the service lives of the devices are greatly influenced. Therefore, it is necessary to design a hole transport material having both higher mobility and glass transition temperature.
Disclosure of Invention
Based on the method, the alkyl derivative is introduced into the triarylamine system to obtain a series of compounds with excellent performance, wherein the introduction of the benzo alkane derivative is beneficial to improving the stability of a molecular fragment, and meanwhile, the molecular weight is increased, so that the glass transition temperature of the molecule is improved. In addition, in order to obtain a compound with a high triplet energy level, a chain or cyclic alkane compound is directly introduced into a molecular system, so that conjugation between molecules can be broken, and a conjugation range is reduced, thereby obtaining a product with a high triplet energy level. Meanwhile, compared with aryl, the alkyl has stronger electron supply capability, can improve the electron supply characteristic of molecules, enhances the electron transmission capability, and has stronger rigidity of the benzocycloalkyl compound, so that the molecules are more stable. The compound can be used as a hole transport material of an OLED device to provide stronger efficiency and service life for the organic electroluminescent device.
To achieve the above object, the present invention provides a compound having a chemical structure represented by formula (1):
Figure BDA0003914410890000021
/>
in the formula (1), L 1 -L 3 Identical or different, each independently selected from a single bond, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C5-C30 heteroaryl;
A 1 -A 3 are identical or different and are each independently selected from single bonds, substituted or unsubstituted C2-C24 chain alkylene groups, substituted or unsubstituted C2-C24 branched chain alkylene groups, and takenSubstituted or unsubstituted C3-C18 cycloalkylene, substituted or unsubstituted C3-C18 heterocycloalkylene, substituted or unsubstituted C2-C24 alkylimine, substituted or unsubstituted C2-C24 alkylidene ether, substituted or unsubstituted C2-C30 alkylidene sulfide, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C6-C30 arylimine, substituted or unsubstituted C6-C30 arylene ether, substituted or unsubstituted C2-C24 arylene sulfide, substituted or unsubstituted C5-C30 heteroarylimine, substituted or unsubstituted C5-C30 heteroarylene ether, substituted or unsubstituted C2-C24 heteroarylene sulfide, and A 1 -A 3 At least one alkylene group selected from C2-C24, substituted or unsubstituted C3-C18 cycloalkylene;
Ar 1 -Ar 3 identical or different, each independently selected from the group consisting of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, and Ar 1 -Ar 3 At least one selected from at least one of the groups represented by the following formula (2):
Figure BDA0003914410890000022
in the formula (2), Z 1 -Z 9 Each independently selected from C (R) 1 R 2 )、N(R 3 ) O or S;
ar is selected from a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C5-C60 heteroaryl;
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
In another aspect, the present invention provides an organic layer comprising the aforementioned compounds of the present invention.
In another aspect, the present invention provides the use of the aforementioned compounds of the invention or of the aforementioned organic layers in organic optoelectronic devices.
In another aspect, the present invention further provides an organic optoelectronic device, which includes a first electrode, a second electrode, and an organic layer as described above, where the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, or an electron transport layer.
In another aspect, the invention also provides a display or lighting device comprising an organic optoelectronic device as described above.
Compared with the prior art, the invention has the beneficial effects that: the compound provided by the invention has the advantages that on one hand, the structure is more stable by introducing the benzo alkyl, on the other hand, the conjugation of the compound is reduced by introducing the chain or cyclic alkyl, the triplet state energy level of the compound is improved by combining, and the alkyl has better electron transmission capability relative to the aryl, so that the whole compound has good hole transmission performance and thermal stability. The compound is applied to an organic photoelectric device, so that the device has higher hole mobility, and electrons and excitons can be effectively blocked from entering a hole transmission layer, thereby improving the efficiency of the device, and meanwhile, molecules have high stability to further improve the luminous efficiency and the service life of the device.
Detailed Description
The present invention provides a compound having a chemical structure represented by formula (1):
Figure BDA0003914410890000031
in the formula (1), L 1 -L 3 Identical or different, each independently selected from a single bond, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C5-C30 heteroaryl;
A 1 -A 3 identical or different, each independently selected from a single bond, a substituted or unsubstituted C2-C24 chain alkylene, a substituted or unsubstituted C2-C24 branched chain alkylene, a substituted or unsubstituted C3-C18 cycloalkylene, a substituted or unsubstituted C3-C18 heterocycloalkylene, a substituted or unsubstituted C2-C24 alkylimine, a substituted or unsubstituted C2-C24 alkylene ether, a,Substituted or unsubstituted C2-C30 alkylene sulfide, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C6-C30 arylimine, substituted or unsubstituted C6-C30 arylene ether, substituted or unsubstituted C2-C24 arylene sulfide, substituted or unsubstituted C5-C30 heteroarylimine, substituted or unsubstituted C5-C30 heteroarylene ether, substituted or unsubstituted C2-C24 heteroarylene sulfide, and A 1 -A 3 At least one alkylene group selected from C2-C24, substituted or unsubstituted C3-C18 cycloalkylene;
Ar 1 -Ar 3 identical or different, each independently selected from the group consisting of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, and Ar 1 -Ar 3 At least one selected from at least one of the groups represented by the following formula (2):
Figure BDA0003914410890000041
in the formula (2), Z 1 -Z 9 Each independently selected from C (R) 1 R 2 )、N(R 3 ) O or S;
ar is selected from a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C5-C60 heteroaryl;
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
Examples of the substituents in the present invention are described below, but the substituents are not limited thereto:
by [ substituted or unsubstituted ] is meant a substitution with one or more substituents selected from the group consisting of: deuterium, halogen, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, and heteroaryl, acenaphthylene, or unsubstituted; or substituted with a substituent linking two or more of the substituents exemplified above, or unsubstituted; for example, "a substituent linking two or more substituents" may include a biphenyl group, i.e., the biphenyl group may be an aryl group, or a substituent linking two phenyl groups.
The "alkyl group" may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl.
The above description of alkyl groups also applies to alkyl groups in aralkyl groups, aralkylamine groups, alkylaryl groups, and alkylamino groups.
The "heteroalkyl" group may be a straight-chain or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl includes, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, alkoxy including, but not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzoxy; alkylthio includes, but is not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, t-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio.
The [ cycloalkyl ] group may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl.
[ heterocycloalkyl ] may be a cycloalkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heterocycloalkyl includes, but is not limited to
Figure BDA0003914410890000051
Etc.
The "aryl" is not particularly limited, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. Fluorenyl groups can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. In addition, two of the substituents may combine with each other to form a spiro structure, for example, 9' -spirobifluorenyl, and the like.
The above description of aryl groups applies to arylene groups, except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphinyl, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino and arylheteroarylamino groups.
[ heteroaryl ] contains one or more of N, O, P, S, si and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazolazolyl, benzimidazolophenidinyl, spiro [ fluorene-9, 9' -xanthene ], benzobinaphthyl, dinaphthyl, naphthyfuranyl, dinaphthylthiophenyl, naphthybenzothiophenyl, triphenylphosphine oxide, triphenylborane.
The above description of heteroaryl groups applies to heteroaryl groups in heteroaryl amine groups and arylheteroaryl amine groups.
The above description of heteroaryl groups applies to heteroarylene groups, except that the heteroarylene group is divalent.
In particular, the aforementioned compounds of the present invention may be unsubstituted or substituted with one or more substituents selected from the group consisting of. Examples of the amine group include deuterium, halogen, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylheteroaryl amino group, arylphosphine group, and heteroaryl group.
In some embodiments, A in formula (1) 1 -A 3 At least one selected from at least one of the groups represented by the following formula (3): :
Figure BDA0003914410890000061
in the formula (3), X 1 -X m Are identical or different and are each independently selected from C (R 16 R 17 )、N(R 18 ) O or S, m is more than or equal to 4 and is an integer;
y is selected from C (R) 19 R 20 )、N(R 21 ) O or S;
R 4 -R 21 the same or different, each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or bonded to an adjacent atom to form a ring;
n is greater than or equal to 1 and is an integer, and is the linking site of the atom.
In formula (1), the aforementioned alkyl group may have 1 to 10, 1 to 20 or 20 to 30 carbon atoms; the aforementioned cycloalkyl groups may have a carbon number of 3 to 10, 3 to 20 or 3 to 30; the number of carbon atoms of the aforementioned heteroalkyl group may be 3 to 10, 1 to 20 or 20 to 30; the number of carbon atoms of the aforementioned heterocycloalkyl group may be 3 to 10, 3 to 20 or 20 to 30; the number of carbon atoms of the aforementioned aryl group may be 6 to 10, 6 to 20 or 20 to 30; the number of carbon atoms of the aforementioned heteroaryl groups may be 6 to 10, 6 to 20 or 20 to 30.
In some embodiments, L in formula (1) 1 -L 3 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and,
Figure BDA0003914410890000071
In some embodiments, the compound of formula (1) is selected from the following chemical structures:
Figure BDA0003914410890000072
/>
Figure BDA0003914410890000081
/>
Figure BDA0003914410890000091
/>
Figure BDA0003914410890000101
in another aspect, the present invention provides an organic layer comprising the compounds of the foregoing invention.
In a further aspect the present invention provides the use of a compound as described above and/or an organic layer as described above in an organic optoelectronic device.
The organic photoelectric device provided by the invention comprises a first electrode, a second electrode and one or more organic layers arranged between the first electrode and the second electrode, wherein the organic layers can be of a single-layer structure or a multi-layer serial structure laminated with two or more organic layers, and the organic layers such as at least one layer of a hole injection layer, a hole transmission layer, a light emitting layer, an electron injection layer or an electron transmission layer can be prepared by using common methods and materials for preparing the organic photoelectric device.
In the organic photoelectric device provided by the present invention, the first electrode serves as an anode layer, and the anode material may be, for example, a material having a large work function, so that holes are smoothly injected into an organic layer, such as a metal, a metal oxide, a combination of a metal and an oxide, a conductive polymer, or the like, a metal oxide, such as Indium Tin Oxide (ITO), zinc oxide, indium Zinc Oxide (IZO), or the like.
In the organic photoelectric device provided by the invention, the second electrode serves as a cathode layer, the cathode material may be, for example, a material having a small work function so that electrons are smoothly injected into the organic layer, the cathode material may be, for example, a metal such as magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead or an alloy thereof, or a multilayered structure material, and the cathode material is preferably magnesium and silver.
In the organic photoelectric device provided by the invention, a material of the hole injection layer, preferably a material having a Highest Occupied Molecular Orbital (HOMO) between a work function of the anode material and a HOMO of the surrounding organic layer, is used as a material that advantageously receives holes from the anode at a low voltage.
In the organic photoelectric device provided by the invention, the material of the hole transport layer is a material having high mobility to holes and is suitable as a material for receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. The material of the hole transport layer includes, but is not limited to, an organic material of arylamine, a conductive polymer, a block copolymer having both conjugated and non-conjugated portions, and the like.
In the organic photoelectric device provided by the invention, the compound provided by the invention can be applied to a light-emitting layer of the device.
In the organic photoelectric device provided by the present invention, the material of the electron transport layer is a material having high mobility for electrons, and is suitable as a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer.
In the organic photoelectric device provided by the invention, the material of the cover layer generally has a high refractive index, so that the light efficiency of the organic light-emitting device can be improved, and the improvement of external light-emitting efficiency is particularly facilitated.
Among the organic photoelectric devices provided by the present invention, the organic photoelectric devices are organic photovoltaic devices, organic light emitting devices, organic solar cells, electronic papers, organic photoreceptors, organic thin film transistors, and the like.
In another aspect, the invention provides a display or lighting device comprising an organic optoelectronic device according to the invention.
The synthesis of the compound represented by the above formula (1) can be carried out by a known method, for example, by cross-coupling reaction using a transition metal such as nickel, palladium or the likeShould be. Other synthetic methods are C-C, C-N coupling reactions using transition metals such as magnesium or zinc. The reaction is preferably Suzuki, buchwald reaction, which is limited to the characteristics of mild reaction conditions and excellent selectivity of various functional groups. The compounds of the present invention are illustrated by the following examples, but are not limited to the compounds and synthetic methods illustrated by these examples. The initial raw materials, the solvent, some common OLED intermediates and other products are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from sigma-Aldrich, 1 h NMR data were determined using a JEOL (400 MHz) nuclear magnetic resonance apparatus and HPLC data were determined using an Shimadzu LC-20AD high performance liquid chromatography apparatus.
The materials used in the examples are:
Figure BDA0003914410890000111
example 1
Synthesis of Compound 1
Figure BDA0003914410890000121
1) Synthesis of intermediate 1-1
To the reaction vessel were added 26.1 g (100 mmol) of Compound 1-A, 16.9 g (100 mmol) of Compound 1-B, 23.4 g (240 mmol) of sodium t-butoxide, 575 mg (1 mmol) of bis-dibenzylideneacetone palladium, 348 mg (1.2 mmol) of tri-t-butylphosphine tetrafluoroborate and 1000mL of xylene (xylene) under argon atmosphere, and the mixture was heated and stirred at 140℃for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtered, the filter cake was washed with a large amount of water, dried in vacuo, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane) to give 24.4 g of compound 1-1, 99.6% pure by HPLC, yield 70%. LC MS: M/Z349.18 (M+); 1H NMR (400 MHz, DMSO-d 6) delta 2.59-2.70 (m, 2H), 2.77 (m, 2H), 7.02 (s, 1H), 7.05-7.15 (m, 4H), 7.22 (m, 3H), 7.22-7.33 (m, 2H), 7.34-7.43 (m, 1H), 7.43-7.54 (m, 4H), 7.57-7.65 (m, 2H), 7.69-7.77 (m, 2H).
2) Synthesis of Compound 1
To the reaction vessel, under argon atmosphere, was added compound 1-1.9 g (100 mmol), compound 1-C41.9 g (100 mmol), sodium t-butoxide 23.4 g (240 mmol), palladium dibenzylidene acetonide 575 mg (1 mmol%), tri-t-butylphosphine tetrafluoroborate 348 mg (1.2 mmol%) and 1000mL xylene (xylene) and stirred at 140℃for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtered, the filter cake was washed with a large amount of water, dried in vacuo, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane) to give 51.6 g of compound 1, 99.9% pure by hplc, and 75% yield. LC MS: M/Z687.39 (M+).
1 H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.48(s,4H),2.59–2.70(m,2H),2.72–2.83(m,2H),6.67(m,1H),7.07–7.18(m,4H),7.18–7.31(m,6H),7.31–7.58(m,12H),7.69–7.76(m,2H),7.76–7.83(m,2H),7.88(d,1H),7.96(d,1H).
Example 2
Synthesis of Compound 12
Figure BDA0003914410890000122
The procedure of example 1 was repeated except that the starting materials were changed to 12-A, 12-B and 21-C. LC MS: M/Z819.44 (M+). HPLC purity: 99.9%, total yield: 50%; 1 H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.72(d,12H),1.80(s,2H),6.91(m,1H),7.10–7.41(m,15H),7.36–7.51(m,5H),7.51–7.58(m,3H),7.68(m,1H),7.75–7.83(m,2H),7.88(d,1H),7.93–8.01(m,2H),8.01–8.06(m,1H).
example 3
Synthesis of Compound 17
Figure BDA0003914410890000131
The procedure of example 1 was repeated except that the starting materials were changed to 17-B and 17-C. LC MS: M/Z720.35 (M+). Total synthesis yield: 52%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.66–1.83(m,4H),2.58–2.71(m,3H),2.66–2.76(m,3H),2.71–2.84(m,2H),6.67(m,1H),7.06–7.43(m,18H),7.43–7.57(m,3H),7.58–7.68(m,3H),7.68–7.78(m,2H),7.78–7.88(m,2H),8.15–8.25(m,2H),8.66(d,1H).
Example 4
Synthesis of Compound 23
Figure BDA0003914410890000132
/>
The procedure of example 1 was repeated except that the starting materials were changed to 23-A, 12-B and 23-C. LC MS: M/Z763.38 (M+). Total synthesis yield: 53%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.69(s,12H),2.07(m,2H),2.77–2.99(m,4H),6.91(m,1H),7.06–7.51(m,21H),7.51–7.58(m,2H),7.68(m,1H),7.75–7.83(m,2H),7.88(d,1H),7.93–8.01(m,2H),8.01–8.06(m,1H).
Example 5
Synthesis of Compound 32
Figure BDA0003914410890000133
The procedure of example 1 was repeated except that the starting materials were changed to 32-A, 32-B and 32-C. LC MS: M/Z807.48 (M+). Total synthesis yield: 51%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.35(s,12H),1.48(s,4H),1.69(s,6H),6.67(m,1H),6.98(m,1H),7.03–7.14(m,4H),7.18–7.26(m,2H),7.30–7.50(m,12H),7.50–7.56(m,1H),7.82–7.91(m,2H),8.06–8.15(m,2H),8.15–8.24(m,2H).
Example 6
Synthesis of Compound 43
Figure BDA0003914410890000141
The procedure of example 1 was repeated except that the starting materials were changed to 43-A, 12-B and 43-C. LC MS: M/Z747.48 (M+). Total synthesis yield: 50%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ0.91(s,12H),1.05–1.36(m,16H),2.79(m,1H),3.41–3.55(m,2H),6.67(m,1H),7.00–7.08(m,2H),7.11–7.18(m,4H),7.18–7.27(m,6H),7.27–7.38(m,8H),7.34–7.43(m,1H),7.43–7.53(m,2H),7.50–7.58(m,4H),7.69–7.77(m,2H).
Example 7
Synthesis of Compound 50
Figure BDA0003914410890000142
The procedure of example 1 was repeated except that the starting materials were changed to 50-A, 12-B and 50-C. LC MS: M/Z643.29 (M+). Total synthesis yield: 58%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.05–1.23(m,4H),2.19–2.37(m,4H),3.23(m,2H),3.48(m,2H),4.57–4.65(m,2H),6.87–6.96(m,2H),7.00–7.08(m,2H),7.11–7.18(m,2H),7.18–7.26(m,3H),7.26–7.37(m,3H),7.34–7.44(m,1H),7.40–7.52(m,5H),7.49–7.58(m,2H),7.68(m,1H),7.75–7.83(m,2H),7.88(d,1H),7.93–8.01(m,2H),8.01–8.06(m,1H).
Example 8
Synthesis of Compound 60
Figure BDA0003914410890000143
The procedure of example 1 was repeated except that the starting materials were changed to 60-A, 12-B and 60-C. LC MS: M/Z793.36 (M+). Total synthesis yield: 52%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.72(s,12H),1.90–2.08(m,4H),2.15–2.27(m,1H),2.31(m,2H),2.79(m,2H),6.11(s,2H),6.91(m,1H),6.94(m,1H),7.10–7.26(m,12H),7.26–7.54(m,11H),7.79(m,2H),7.92–7.98(m,3H).
Example 9
Synthesis of Compound 77
Figure BDA0003914410890000151
The procedure of example 1 was repeated except that the starting materials were changed to 23-A, 12-B and 77-C. LC MS: M/Z803.41 (M+). Total synthesis yield: 53%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.69(s,18H),2.07(s,2H),2.77–2.90(m,4H),6.91(m,1H),7.05–7.58(m,23H),7.68(m,1H),7.74(d,1H),7.84–7.92(m,1H),7.94–8.01(m,1H),8.01–8.06(m,1H).
Example 10
Synthesis of Compound 90
Figure BDA0003914410890000152
The procedure of example 1 was repeated except that the starting materials were changed to 90-A, 12-B and 90-C. LC MS: M/Z871.37 (M+). Total synthesis yield: 53%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.72(s,6H),1.95–2.11(m,4H),5.15–5.23(m,2H),6.11(s,2H),6.91(m,1H),6.97–7.06(m,2H),7.10–7.20(m,4H),7.23(s,4H),7.26–7.43(m,5H),7.38–7.51(m,7H),7.51–7.60(m,3H),7.61–7.72(m,3H),7.75–7.83(m,2H),7.94–8.01(m,1H),8.01–8.09(m,3H).
Example 11
Synthesis of Compound 94
Figure BDA0003914410890000161
The procedure of example 1 was repeated except that the starting materials were changed to 94-A, 94-B and 94-C. LC MS: M/Z805.44 (M+). Total synthesis yield: 53%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.48(s,4H),2.10(s,3H),3.60(t,2H),3.70–3.74(m,2H),6.67(m,1H),7.14–7.43(m,16H),7.43–7.68(m,10H),7.69–7.77(m,2H),8.17–8.27(m,2H),8.66(d,1H).
Example 12
Synthesis of Compound 97
Figure BDA0003914410890000162
The procedure of example 1 was repeated except that the starting materials were changed to 97-A and 43-C. LC MS: M/Z683.41 (M+). Total synthesis yield: 52%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.22(s,12H),1.46–1.52(m,16H),6.67(m,1H),7.14–7.29(m,6H),7.29–7.39(m,7H),7.35–7.43(m,1H),7.43–7.58(m,8H),7.69–7.77(m,2H).
Example 13
Synthesis of Compound 104
Figure BDA0003914410890000163
1) Synthesis of intermediate 104-1
To the reaction vessel were charged 26.1 g (100 mmol) of compound 104-A, 33.8 g (200 mmol) of compound 1-B, 23.4 g (240 mmol) of sodium t-butoxide, 575 mg (1 mmol) of bis-dibenzylideneacetone palladium, 348 mg (1.2 mmol) of tri-t-butylphosphine tetrafluoroborate and 1000mL of xylene (xylene) under argon atmosphere, and the mixture was heated and stirred at 140℃for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtered, the filter cake was washed with a large amount of water, dried in vacuo, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane) to give 33.6 g of compound 104-1, 99.6% pure by HPLC, yield 65%. LC MS: M/Z516.26 (M+). 1 H NMR(400MHz,DMSO-d6)δ2.65(d,4H),7.02(s,2H),7.05–7.15(m,8H),7.34–7.43(m,2H),7.43–7.54(m,8H),7.57–7.65(m,4H),7.69–7.77(m,4H).
2) Synthesis of Compound 1
To the reaction vessel, 104-1.7 g (100 mmol) of compound, 104-C52.4 g (200 mmol), 23.4 g (240 mmol) of sodium t-butoxide, 575 mg (1 mmol) of bis-dibenzylideneacetone palladium, 348 mg (1.2 mmol) of tri-t-butylphosphine tetrafluoroborate and 1000mL of xylene (xylene) were charged under argon atmosphere, and heated and stirred at 140℃for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtered, and the cake was washed with a large amount of waterThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane) to give 62.2 g of compound 1, purity by HPLC of 99.9%, yield 70%. LC MS: M/Z888.54 (M+). 1 H NMR(400MHz,DMSO-d6)δ1.23(s,24H),1.48(s,8H),2.65(d,4H),6.45(m,2H),7.00(d,2H),7.05–7.19(m,10H),7.30–
7.38(m,4H),7.34–7.43(m,2H),7.43–7.53(m,4H),7.50–7.58(m,4H),7.69–7.77(m,4H).
Example 14
Synthesis of Compound 113
Figure BDA0003914410890000171
The procedure of example 13 was repeated except that the starting materials were changed to 113-A, 113-B and 113-C. LC MS: M/Z889.53 (M+). Total synthesis yield: 43%. HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ1.23(s,24H),1.80(s,3H),2.10(s,3H),3.60(t,4H),6.95–7.04(m,2H),7.04–7.12(m,4H),7.14–7.29(m,9H),7.30–7.44(m,10H),7.50–7.58(m,8H).
Example 15
Synthesis of Compound 121
Figure BDA0003914410890000172
The procedure of example 13 was repeated except that the starting material was changed to 121-A. LC MS: M/Z886.62 (M+). Total synthesis yield: 45%; HPLC purity: 99.9%. 1 H NMR(400MHz,DMSO-d6)δ0.91(s,24H),1.13(m,2H),1.48–1.73(m,24H),2.50–2.64(m,2H),6.45(m,2H),7.00(d,2H),7.08(d,2H),7.30–7.42(m,6H),7.37–7.43(m,1H),7.43–7.58(m,9H),7.69–7.77(m,4H).
Device example 1: preparation of organic electroluminescent device
Figure BDA0003914410890000181
The preparation process comprises the following steps: a transparent anode ITO film layer (thickness 150 nm) was formed on a glass substrate to obtain a first electrode as an anode. Then, a mixed material of the compound T-1 and the compound T-2 is evaporated on the surface of the anode by a vacuum evaporation method to serve as a hole injection layer, wherein the mixing ratio is 3:97 (mass ratio), and the thickness is 10nm. And evaporating a compound T-2 with the thickness of 100nm on the hole injection layer to obtain a first layer of hole transport layer. Then, the compound 1 of the present invention was evaporated on the first hole transport layer to a thickness of 10nm to obtain a second hole transport layer. On the second hole transport layer, the compound T-3 and the compound T-4 were co-evaporated at a mass ratio of 95:5 to form an organic light emitting layer having a thickness of 40 nm. Then, on the organic light-emitting layer, a hole blocking layer (thickness 10 nm) was formed by vapor deposition of the compound T-5 in this order, and an electron transport layer (thickness 30 nm) was formed by mixing the compound T-6 and LiQ in a ratio of 4:6 (mass ratio). Finally, magnesium (Mg) and silver (Ag) are mixed at an evaporation rate of 1:9, and vacuum evaporation is performed on the electron injection layer to form a second electrode 109, thereby completing the manufacture of the organic light-emitting device.
Device examples 2 to 15
An organic electroluminescent device was fabricated in the same manner as in device example 1, except that compound 12, 17, 23, 32, 43, 50, 60, 77, 90, 94, 97, 104, 113 and 121 were used instead of compound 1, respectively, in forming the second hole transport layer.
Device comparative examples 1 to 2
An organic electroluminescent device was fabricated in the same manner as in device example 1, except that compound HT-1 and compound HT-2 were used in place of compound 1, respectively, in forming the second hole transport layer.
The above-prepared organic electroluminescent devices were calculated to obtain an operating voltage and efficiency by a computer-controlled Keithley 2400 test system, device lifetimes under dark conditions were obtained using a polar onix (McScience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit, each set of devices example and device comparative example 1 were produced and tested in the same batch as the devices of device comparative example 2, the operating voltage, efficiency and lifetime of the devices of device comparative example 1 were each recorded as 1, and the ratios of the corresponding indexes of device examples 1 to 25 and device comparative example 1, respectively, were calculated as shown in table 1.
TABLE 1
Figure BDA0003914410890000182
Figure BDA0003914410890000191
As is clear from the results of table 1, the compounds used in device examples 1 to 15 all had lower voltages, improved luminous efficiency and significantly improved lifetime when used as the second hole transport layer of the light-emitting device, as compared with the devices formed from the compounds used in device comparative examples 1 to 2.
Therefore, the compound provided by the invention is applied to an organic photoelectric device, so that the device has higher hole mobility, electrons and excitons can be effectively blocked from entering a hole transport layer, the efficiency of the device is improved, meanwhile, molecules have high stability, the luminous efficiency and the service life of the device can be further improved, and the compound has higher application value.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.

Claims (10)

1. A compound having a chemical structure represented by formula (1):
Figure FDA0003914410880000011
in the formula (1), L 1 -L 3 Are identical or different and are each independently selected from single bond and fetchSubstituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
A 1 -A 3 identical or different, each independently selected from the group consisting of a single bond, a substituted or unsubstituted C2-C24 chain alkylene, a substituted or unsubstituted C2-C24 branched chain alkylene, a substituted or unsubstituted C3-C18 cycloalkylene, a substituted or unsubstituted C3-C18 heterocycloalkylene, a substituted or unsubstituted C2-C24 alkylimine, a substituted or unsubstituted C2-C24 alkylene ether, a substituted or unsubstituted C2-C30 alkylene thioether, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C6-C30 arylimine, a substituted or unsubstituted C6-C30 arylene ether, a substituted or unsubstituted C2-C24 arylene sulfide, a substituted or unsubstituted C5-C30 heteroarylimine, a substituted or unsubstituted C5-C30 heteroarylene ether, a substituted or unsubstituted C2-C24 heteroarylene sulfide, and A 1 -A 3 At least one alkylene group selected from C2-C24, substituted or unsubstituted C3-C18 cycloalkylene;
Ar 1 -Ar 3 identical or different, each independently selected from the group consisting of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, and Ar 1 -Ar 3 At least one selected from at least one of the groups represented by the following formula (2):
Figure FDA0003914410880000012
in the formula (2), Z 1 -Z 9 Each independently selected from C (R) 1 R 2 )、N(R 3 ) O or S;
ar is selected from a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C5-C60 heteroaryl;
R 1 -R 3 each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C18 cycloalkylUnsubstituted C2-C30 heteroaryl.
2. The compound according to claim 1, wherein in formula (1), A 1 -A 3 At least one selected from at least one of the groups represented by the following formula (3):
Figure FDA0003914410880000021
in the formula (3), X 1 -X m Are identical or different and are each independently selected from C (R 16 R 17 )、N(R 18 ) O or S, m is more than or equal to 4 and is an integer;
y is selected from C (R) 19 R 20 )、N(R 21 ) O or S;
R 4 -R 21 the same or different, each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or bonded to an adjacent atom to form a ring;
n is greater than or equal to 1 and is an integer, and is the linking site of the atom.
3. The compound according to claim 1, wherein in formula (1), L 1 -L 3 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and,
Figure FDA0003914410880000022
Figure FDA0003914410880000023
4. A compound according to claim 1, wherein the compound is selected from the following chemical structures:
Figure FDA0003914410880000024
/>
Figure FDA0003914410880000031
/>
Figure FDA0003914410880000041
/>
Figure FDA0003914410880000051
5. an organic layer comprising one or more of the compounds of any one of claims 1 to 4.
6. Use of a compound according to any one of claims 1 to 4 or an organic layer according to claim 5 in an organic optoelectronic device.
7. An organic optoelectronic device comprising one or more of the compounds of any one of claims 1 to 4 or the organic layer of claim 5.
8. The organic optoelectronic device according to claim 7, comprising a substrate, a first electrode, an organic layer and a second electrode, wherein the organic layer is at least one layer of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the material thereof comprises one or more of the compounds according to any one of claims 1 to 4.
9. The organic optoelectronic device according to claim 8, wherein the organic optoelectronic device is at least one of an organic photovoltaic device, an organic light emitting device, an organic solar cell, an electronic paper, an organic photoreceptor, and an organic thin film transistor.
10. A display or lighting device comprising the organic optoelectronic device of claims 7 to 9.
CN202211333272.4A 2022-10-28 2022-10-28 Compound and application thereof in organic photoelectric device Pending CN116063187A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211333272.4A CN116063187A (en) 2022-10-28 2022-10-28 Compound and application thereof in organic photoelectric device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211333272.4A CN116063187A (en) 2022-10-28 2022-10-28 Compound and application thereof in organic photoelectric device

Publications (1)

Publication Number Publication Date
CN116063187A true CN116063187A (en) 2023-05-05

Family

ID=86175853

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211333272.4A Pending CN116063187A (en) 2022-10-28 2022-10-28 Compound and application thereof in organic photoelectric device

Country Status (1)

Country Link
CN (1) CN116063187A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116462592A (en) * 2023-03-24 2023-07-21 山东钥熠材料科技有限公司 Compound and application thereof in organic photoelectric device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116462592A (en) * 2023-03-24 2023-07-21 山东钥熠材料科技有限公司 Compound and application thereof in organic photoelectric device

Similar Documents

Publication Publication Date Title
CN114805386B (en) Organic compound, host material, and organic photoelectric device
KR101412437B1 (en) New compounds and organic electronic device using the same
KR101314383B1 (en) New compounds and organic electronic device using the same
CN114835590A (en) Organic compound and application thereof in organic photoelectric device
KR102192691B1 (en) An electroluminescent compound and an electroluminescent device comprising the same
CN114890935A (en) Compound and application thereof in organic photoelectric device
CN114716329A (en) Organic compound and organic photoelectric device
WO2019013487A1 (en) Novel compound and organic light-emitting device using same
CN111303149B (en) Benzo five-membered fused heterocycle organic compound and application thereof
CN110776513B (en) Organic compound and application thereof
CN116063187A (en) Compound and application thereof in organic photoelectric device
CN115304498A (en) Compound and application thereof in organic photoelectric device
CN115448932A (en) Compound, organic photoelectric device and display or lighting device
CN115304586A (en) Compound and application thereof in organic photoelectric device
CN115141106B (en) Compound, organic material and organic photoelectric device
CN116063191A (en) Compound and application thereof in organic photoelectric device
CN116462592A (en) Compound and application thereof in organic photoelectric device
CN112940007A (en) Organic compound, and organic electroluminescent device and electronic device using same
CN115109065B (en) Organic compound, host material, and organic electroluminescent device
CN116332770A (en) Spiro compound and application thereof in organic photoelectric device
CN116332772A (en) Compound and application thereof
CN116102435A (en) Compound and application thereof in organic photoelectric device
CN116813583A (en) Compound and application thereof in organic photoelectric device
CN114805370B (en) Indolocarbazole-based compound and application thereof in organic electroluminescent device
CN116082167A (en) Organic compound and application thereof in organic photoelectric 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
CB03 Change of inventor or designer information

Inventor after: Wang Xiangcheng

Inventor after: He Mu

Inventor before: Wang Peng

Inventor before: Wang Xiangcheng

Inventor before: He Mu

CB03 Change of inventor or designer information