CN115304586A - Compound and application thereof in organic photoelectric device - Google Patents

Compound and application thereof in organic photoelectric device Download PDF

Info

Publication number
CN115304586A
CN115304586A CN202211070563.9A CN202211070563A CN115304586A CN 115304586 A CN115304586 A CN 115304586A CN 202211070563 A CN202211070563 A CN 202211070563A CN 115304586 A CN115304586 A CN 115304586A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
organic
group
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN202211070563.9A
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 CN202211070563.9A priority Critical patent/CN115304586A/en
Publication of CN115304586A publication Critical patent/CN115304586A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
    • 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
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D405/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • 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
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms 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
    • C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a compound and application thereof in an organic photoelectric device, wherein the chemical structure of the compound is shown as formula (I), X in group A 1 ‑X 3 Independently selected from O, S, -NR 16 -or-CR 17 R 18 -, where at most two are-CR 17 R 18 -, at most one is O; z 1 ‑Z 9 Independently selected from O, S and-CR 19 R 20 -or-NR 21 -, and at least one in the same molecule is-CR 19 R 20 -; b is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, R 1 ‑R 8 At least one selected from the group represented by the formula (II). The compound of the invention introduces a ring-merging group, adjusts the energy levels of HOMO and LUMO, reduces the sublimation temperature, is applied to organic photoelectric devices as an electron transport material, and greatly improves the luminous efficiency and prolongs the service life of the devices.

Description

Compound and application thereof in organic photoelectric device
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to a compound and application thereof in an organic photoelectric device.
Background
Organic Light Emission Diodes (OLED) devices are devices with sandwich-like structures, including positive and negative electrode films and Organic functional material layers sandwiched between the electrode films, and the technology has been widely applied to display panels of novel lighting fixtures, smart phones, tablet computers and other products, and will expand to the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the research and development of OLED technology, the preparation technology of luminescent materials, hole transport materials and electron transport materials used by devices is improved day by day. However, the electron mobility of the electron transport material is much lower than the hole mobility of the hole transport material, which may cause unbalanced injection and transport of carriers in the OLED device, and decrease the recombination probability of holes and electrons, thereby decreasing the light emitting efficiency of the device; on the other hand, the low electron mobility of the electron transport material can cause the working voltage of the device to be increased, thereby reducing the overall power efficiency of the device and causing energy loss.
Disclosure of Invention
The invention provides a compound for an organic photoelectric device, which has a chemical structure shown as a formula (I):
Figure BDA0003829965200000011
in the formula (I), A is selected from the following group structures:
Figure BDA0003829965200000012
X 1 -X 3 independently selected from O, S, -NR 16 -or-CR 17 R 18 -, where at most two are-CR 17 R 18 -, at most one is O;
Z 1 -Z 9 independently selected from O, S and-CR 19 R 20 -or-NR 21 -, and at least one in the same molecule is-CR 19 R 20 -；
* Is a linking site to B;
b is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
R 1 -R 8 and R 16 -R 21 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, and R 1 -R 8 At least one group structure selected from the group represented by formula (II):
Figure BDA0003829965200000021
e is an electron withdrawing group containing N or O;
L 1 and L 2 Selected from single bond, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
Compared with the prior art, the invention has the beneficial effects that: due to the introduction of the fused ring group, the HOMO and LUMO energy levels of the compound are adjusted, meanwhile, the accumulation of the compound molecules is looser, the sublimation temperature is reduced, the evaporation operation is facilitated, the quenching process among the molecules is reduced, and the service life of the device is prolonged. In addition, some electron-withdrawing groups containing N atoms or O atoms are introduced to reduce the LUMO energy level of molecules, so that the material is more suitable for electron transport materials. The compound is applied to organic photoelectric devices, enables the devices to have higher efficiency, has high stability of molecules, and can further improve the luminous efficiency and the service life of the devices.
Detailed Description
Embodiments of the specifically disclosed compounds and their use in organic opto-electronic devices are described in detail below. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments, and is not intended to limit the scope of the present invention; in the description and claims of the present application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and any methods, devices, and materials similar or equivalent to those in the examples of the present invention may be used in the practice of the present invention, in addition to the specific methods, devices, and materials used in the examples, in light of the knowledge of those skilled in the art to understand the prior art and to describe the present invention.
Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:
[ substituted or unsubstituted ] means substituted with one or more substituents selected from the group consisting of: deuterium, halogen, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino 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, arylphosphine group, and heteroaryl group, acenaphthylene group, 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., a biphenyl group may be an aryl group, or a substituent linking two phenyl groups.
[ alkyl ] may be a linear or branched alkyl group, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is 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, aralkylamino, alkylaryl, and alkylamino groups.
[ heteroalkyl ] may be a linear 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, and the like; alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isoproxy), 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-methylbenzyloxy, and the like; alkylthio includes, but is not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.
[ cycloalkyl ] may be a cyclic cycloalkyl group, 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, and the like.
[ 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 BDA0003829965200000031
[ aryl ] is not particularly limited, and 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, quaterphenyl, pentabiphenyl, and the like, polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, and the like, and the fluorenyl groups can be substituted, such as 9,9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. In addition, two of the substituents may be bonded to each other to form a spiro ring structure, for example, 9,9' -spirobifluorenyl group 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, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
[ heteroaryl ] comprises one or more of N, O, P, S, si and Se as a heteroatom. <xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , [ -9,9' - ], , , , , , , . </xnotran>
The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.
The above description of heteroaryl groups can be used for heteroarylenes, except that the heteroarylene group is divalent.
The invention provides a compound, which has a chemical structure shown as a formula (I):
Figure BDA0003829965200000041
in the formula (I), A is selected from the following group structures:
Figure BDA0003829965200000042
X 1 -X 3 independently selected from O, S, -NR 16 -or-CR 17 R 18 -, where at most two are-CR 17 R 18 -, at most one is O;
Z 1 -Z 9 independently selected from O, S and-CR 19 R 20 -or-NR 21 -, and at least one in the same molecule is-CR 19 R 20 -；
* Is a linking site with B;
b is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
R 1 -R 8 and R 16 -R 21 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, and R 1 -R 8 At least one group structure selected from the group represented by formula (II):
Figure BDA0003829965200000051
e is an electron withdrawing group containing N or O;
L 1 and L 2 Selected from single bonds, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
Specifically, the chemical structure represented by formula (i) may be unsubstituted or substituted with one or more substituents selected from, for example, 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, arylheteroarylamino group, arylphosphine group, and heteroaryl group.
The compound is a multi-parallel-ring structure, has good thermal stability, has suitable HOMO, LUMO energy levels and Eg, has higher triplet state energy level and carrier mobility, can be matched with adjacent energy levels, has higher thermal stability and film forming stability, is a novel OLED material, and can effectively improve the efficiency and prolong the service life of devices when being applied to OLED devices.
In some embodiments, in formula (ii), E is selected from the following substituents:
Figure BDA0003829965200000052
Figure BDA0003829965200000061
wherein R is 11 -R 15 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, and n is selected from 1, 2,3, or 4.
In some embodiments, the compound of formula (i) is selected from one or more of the following chemical structures:
Figure BDA0003829965200000062
Figure BDA0003829965200000071
Figure BDA0003829965200000081
in one aspect, the present invention provides an organic layer comprising the aforementioned compound of the present invention.
In one aspect the present invention provides the use of a compound according to the invention as hereinbefore described and/or an organic layer as hereinbefore described in an organic opto-electronic 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, and is of a bottom or top light-emitting device structure, wherein the organic layers can be of a single-layer structure or a multi-layer series structure laminated with two or more organic layers, and the organic layers comprise 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, and can be prepared by using common methods and materials for preparing organic photoelectric devices, and the compound provided by the invention is used as the organic layer of the organic photoelectric device.
In the organic photoelectric device provided by the invention, the first electrode is used as an anode layer, and the anode material can be a material with a large work function, so that holes can be smoothly injected into the organic layer; for example, a metal oxide, a combination of a metal and an oxide, a conductive polymer, or the like may be used, and the metal oxide may be, for example, 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 is used as a cathode layer, the cathode material can be a material with a small work function, for example, so that electrons can be smoothly injected into the organic layer, the cathode material can be metal or a material with a multilayer structure, for example, the metal can be magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, lead or an alloy thereof, and the cathode material is preferably magnesium and silver.
In the organic opto-electronic device provided by the present invention, the material of the hole injection layer is preferably a material having a Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer as the material that advantageously receives holes from the anode at low voltage.
In the organic photoelectric device provided by the present invention, the material of the hole transport layer is a material having high mobility to holes, and is suitable for receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and includes, but is not limited to, organic materials of arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
In the organic photoelectric device provided by the invention, the material of the electron transport layer is a material with high mobility to electrons, and is suitable for being used as a material for favorably receiving electrons from a cathode and transporting the electrons to a light-emitting layer, and the compound shown as the formula (I) can be applied to the electron transport layer of the device.
In the organic photoelectric device provided by the invention, the material of the covering layer generally has high refractive index, which is beneficial to improving the light efficiency of the organic light-emitting device, especially the external light-emitting efficiency.
The organic photoelectric device provided by the invention is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.
In one aspect, the present invention provides a display or lighting device comprising the organic optoelectronic device of the present invention.
The technical solution of the present invention is further explained by specific examples below.
Synthesis examples:
the synthesis of the compound represented by the above formula (I) can be carried out by a known method. For example, a cross-coupling reaction using a transition metal such as nickel or palladium, and a C-C or C-N coupling reaction using a transition metal such as magnesium or zinc are other synthesis methods. The reaction is limited to mild reaction conditions, superior selectivity of various functional groups and the like, and Suzuki and Buchwald reactions are preferred. The compounds of the present invention are illustrated by, but not limited to, the following examples. The initial raw materials and solvents of the invention and some common products such as OLED intermediates are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from sigma-Aldrich. 1 H-NMR data were measured using a JEOL (400 MHz) nuclear magnetic resonance apparatus, and HPLC data were measured using a Shimadzu LC-20AD HPLC apparatus.
The materials used in the examples were:
Figure BDA0003829965200000101
example 1
Synthesis of Compound 1
Figure BDA0003829965200000102
1) Synthesis of intermediate 1-1
Compound 1-B (32.11g, 120mmol) was added to THF (3 OOml) under an argon atmosphereAfter the reaction flask is cooled to 80 ℃ below zero, 150mmol of n-butyllithium is added dropwise, after the dropwise addition, the reaction flask is kept warm for 1h, then a solution of the compound 1-A (13.4g, 100mmol) in THF (50 ml) is added dropwise, the reaction flask is kept warm for 1h, and then the reaction flask is warmed to room temperature and stirred overnight. Hydrochloric acid (2 mol/L) is added to adjust the pH to be neutral, and then white crude product is obtained by filtration, and the crude product is refined by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) to obtain 17.8g of compound 1-1, the yield is 55%, and the HPLC purity is 99.1%. LC MS M/Z322.08 (M +); 1 H NMR(400MHz,DMSO-d6)δ4.92(m,1H),5.02(m,1H),5.90(s,1H),7.07(m,1H),7.26–7.39(m,3H),7.43(m,1H),7.44–7.53(m,3H),7.54–7.61(m,2H),7.64(m,1H),7.81(m,1H).
2) Synthesis of intermediate 1-2
Under argon atmosphere, adding intermediate 1-1 (32.28g, 100mmol), trifluoroacetic acid (34.21g, 300mmol) and dichloromethane (300 mL) into a reaction flask, reacting for 2 hours under argon protection, adding sodium hydroxide aqueous solution until the reaction solution is neutral, separating, drying the organic phase with anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) to give 23.72g of intermediate 1-2, yield: 78%, HPLC purity 99.5%. LC MS M/Z304.07 (M +); 1 H NMR(400MHz,DMSO-d6)δ4.92(m,1H),5.02(m,1H),7.07(m,1H),7.22–7.42(m,5H),7.46(m,1H),7.50–7.59(m,2H),7.79–7.92(m,2H).
3) Synthesis of Compound 1
Under argon atmosphere, intermediate 1-2.48g (100 mmol), compound 1-C23.81 g (100 mmol), pd (PPh) 3 ) 2 Cl 2 1.4g (2 mmol), 200ml (300 mmol) of 1.5M aqueous sodium carbonate solution and 1000ml of ethylene glycol dimethyl ether (DME) were stirred overnight at 80 ℃. Cooling to room temperature, adding 800ml water to separate out a great amount of solid, filtering, washing the filter cake with water for 3 times, and vacuum drying. The crude product was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 37.93g of Compound 1, yield 82%, HPLC purity 99.9%. LC MS: M/Z462.17 (M +); 1 H NMR(400MHz,DMSO-d6)δ4.92(m,1H),5.02(m,1H),7.07(m,1H),7.22–7.40(m,7H),7.42–7.58(m,5H),7.54–7.66(m,2H),7.73–7.84(m,2H),7.84–7.92(m,1H),8.04–8.12(m,1H),8.56(m,1H).
example 2
Synthesis of Compound 4
Figure BDA0003829965200000111
1) Synthesis of intermediate 4-1
The procedure of example 1 was repeated, except that the starting material was changed to 4-A. LC MS M/Z334.11 (M +); 1 H NMR(400MHz,DMSO-d6)δ1.75–1.91(m,1H),1.86–1.95(m,1H),1.91–2.01(m,1H),2.09–2.23(m,1H),2.66–2.77(m,1H),2.72–2.83(m,1H),5.13(s,1H),6.90(m,1H),7.07–7.17(m,2H),7.21(m,1H),7.32(m,1H),7.43(m,1H),7.44–7.53(m,3H),7.54–7.62(m,2H),7.81(m,1H).
2) Synthesis of intermediate 4-2
The procedure was repeated in the same manner as in example 1 except that the starting material was changed to 4-1. LC MS M/Z282.14 (M +); 1 H NMR(400MHz,DMSO-d6)δ1.64–1.80(m,2H),2.18(m,2H),2.70(m,2H),6.94(m,1H),6.98–7.15(m,3H),7.35(m,2H),7.46(m,2H),7.53(m,2H),7.88(m,2H).
3) Synthesis of Compound 4
To a reaction vessel were added 4 to 2.68g (100 mmol) of the compound 4 to C22.13g (240 mmol), sodium t-butoxide 23.4g (240 mmol), palladium bis-dibenzylideneacetone 575 mg (1 mmol%), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl 953 mg (2 mmol%) and 1000mL of xylene (xylene) under an argon atmosphere, and the mixture was stirred under heating at 140 ℃ for 15 hours. The reaction mixture was cooled to room temperature, 1000ml of water was added, filtration was carried out, the filter cake was washed with a large amount of water, vacuum-dried, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to obtain 40.13g of Compound 4, purity by HPLC 99.9%, yield 80%. LC MS: M/Z501.22 (M +); 1 H NMR(400MHz,DMSO-d6)δ1.75–2.03(m,2H),2.06(m,1H),2.31(m,1H),2.66–2.83(m,2H),6.94(m,1H),6.99–7.14(m,3H),7.35(m,1H),7.40(m,1H),7.39–7.50(m,3H),7.46–7.57(m,6H),7.84–7.92(m,2H),8.03–8.11(m,2H),8.15–8.26(m,2H).
example 3
Synthesis of Compound 13
Figure BDA0003829965200000121
In the same manner as in example 1 except that the starting materials were changed to 13-A, 13-B and 13-C, LC MS: M/Z569.28 (M +), total yield of synthesis: 34 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.25(m,11H),1.94(d,1H),2.19(d,1H),7.00–7.12(m,4H),7.35(m,1H),7.42–7.57(m,9H),7.67(m,1H),7.72(m,1H),7.84–7.92(m,1H),8.15–8.21(m,1H),8.30–8.40(m,4H).
example 4
Synthesis of Compound 19
Figure BDA0003829965200000122
In the same manner as in example 1 except that the starting materials were changed to 19-A and 19-C, LC MS: M/Z629.28 (M +), total yield: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.15(m,2H),1.34–1.48(m,2H),1.48–1.70(m,4H),2.69–2.78(m,1H),2.84(m,1H),7.06(m,1H),7.09–7.21(m,2H),7.26(m,1H),7.35(m,1H),7.41–7.60(m,9H),7.63–7.81(m,3H),7.84–7.92(m,1H),8.08(m,1H),8.26–8.40(m,5H),8.70(t,,1H).
example 5
Synthesis of Compound 32
Figure BDA0003829965200000131
In the same manner as in example 1 except that the starting materials were changed to 32-A and 32-C, LC MS: M/Z835.21 (M +), total yield: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ3.42(m,1H),3.67(m,1H),6.88–7.02(m,2H),7.18(m,1H),7.27(m,1H),7.31–7.40(m,2H),7.40–7.50(m,2H),7.50–7.60(m,2H),7.63–7.81(m,3H),7.84–7.92(m,2H),8.04–8.14(m,3H),8.70(t,1H).
example 6
Synthesis of Compound 37
Figure BDA0003829965200000132
In the same manner as in example 1 except that the starting materials were changed to 37-A and 37-C, LC MS: M/Z654.30 (M +), total yield of synthesis: 33 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.22(d,5H),1.36(m,1H),1.55–1.90(m,3H),2.18(t,2H),7.04–7.17(m,3H),7.28–7.40(m,4H),7.46(m,1H),7.52(m,2H),7.54–7.60(m,1H),7.64–7.81(m,6H),7.84–7.92(m,1H),7.99(m,2H),8.04–8.13(m,5H),8.32–8.40(m,2H).
example 7
Synthesis of Compound 53
Figure BDA0003829965200000133
The procedure of example 1 was repeated, except that the starting materials were changed to 32-A, 13-B and 53-C. LC MS M/Z514.17 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ3.42(m,1H),3.67(m,1H),6.88–7.02(m,2H),7.13–7.31(m,3H),7.31–7.57(m,7H),7.61–7.71(m,2H),7.66–7.78(m,4H),7.84–7.92(m,1H),8.15–8.21(m,1H).
example 8
Synthesis of Compound 72
Figure BDA0003829965200000141
The procedure of example 1 was repeated, except that the starting materials were changed to 72-A and 72-C. LC MS M/Z501.22 (M +). The total synthesis yield is as follows: 30 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.75–2.03(m,2H),2.06(m,1H),2.31(m,1H),2.66–2.83(m,2H),6.94(m,1H),6.99–7.14(m,3H),7.35(m,1H),7.39–7.55(m,6H),7.55–7.64(m,3H),7.77(m,1H),7.84–7.92(m,1H),8.03–8.12(m,3H),8.24–8.32(m,2H).
example 9
Synthesis of Compound 75
Figure BDA0003829965200000142
The procedure of example 1 was repeated, except that the starting materials were changed to 75-A and 75-C. LC MS M/Z592.29 (M +). The total synthesis yield is as follows: 32 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ0.94(d,5H),1.17–1.28(m,7H),1.49(d,1H),6.91–7.00(m,2H),7.00–7.10(m,2H),7.31–7.62(m,10H),7.73–7.85(m,2H),7.85–7.92(m,1H),7.99–8.12(m,2H),8.64–8.70(m,2H),9.18–9.24(m,2H).
example 10
Synthesis of Compound 80
Figure BDA0003829965200000143
The procedure was as in example 1 except that the starting materials were changed to 80-A and 80-C. LC MS M/Z516.22 (M +). The total synthesis yield is as follows: 32 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.45(s,3H),1.51(s,3H),4.16(d,1H),4.41(d,1H),7.07(m,1H,),7.20–7.30(m,2H),7.31–7.40(m,4H),7.46(m,1H),7.52(m,2H),7.78(m,2H),7.82–7.91(m,3H),8.04–8.15(m,4H),8.33(m,1H).
example 11
Synthesis of Compound 95
Figure BDA0003829965200000151
The procedure of example 1 was repeated, except that the starting materials were changed to 95-A and 95-C. LC MS M/Z556.22 (M +). The total synthesis yield is as follows: 33%; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.32–1.51(m,4H),1.59–1.78(m,4H),2.80(m,2H,),6.98–7.09(m,2H),7.26–7.36(m,2H),7.38–7.63(m,6H),7.73(m,1H),7.79(m,1H),7.94–8.02(m,1H),9.29(d,1H).
example 12
Synthesis of Compound 101
Figure BDA0003829965200000152
The procedure of example 1 was repeated, except that the starting materials were changed to 101-A and 101-C. LC MS M/Z606.30 (M +). The total synthesis yield is as follows: 32 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.25(m,12H),7.00–7.12(m,4H),7.23–7.40(m,6H),7.42–7.66(m,9H),7.79(m,2H),7.84–7.96(m,3H),8.08(m,1H),8.52–8.60(m,1H).
example 13
Synthesis of Compound 106
Figure BDA0003829965200000153
The procedure of example 1 was repeated, except that the starting materials were changed to 106-A, 13-B and 106-C. LC MS M/Z498.21 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.25(s,12H),1.94(d,1H),2.19(d,1H),6.99–7.12(m,4H),7.30–7.57(m,6H),7.63–7.78(m,4H),7.84–7.92(m,1H),8.18(d,1H).
example 14
Synthesis of Compound 126
Figure BDA0003829965200000154
The procedure of example 1 was repeated, except that the starting materials were changed to 126-A and 126-C. LC MS M/Z644.28 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.27(s,12H),7.13(m,1H),7.16–7.25(m,2H),7.30–7.40(m,4H),7.42–7.58(m,5H),7.85–7.94(m,3H),8.01(m,2H),8.05–8.15(m,4H),8.33(m,1H),8.42–8.48(m,2H).
example 15
Synthesis of Compound 147
Figure BDA0003829965200000161
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 147-A and 147-C. LC MS M/Z468.22 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.22(d,6H),1.36(m,1H),1.55–1.90(m,3H),2.18(t,2H),7.04–7.17(m,3H),7.28–7.60(m,8H),7.70–7.81(m,3H),7.84–7.92(m,1H),8.04–8.12(m,1H).
example 16
Synthesis of Compound 172
Figure BDA0003829965200000162
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 172-A and 172-C. LC MS M/Z612.28 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.19(s,6H),1.25(s,6H),2.06(s,4H),6.45–6.55(m,2H),6.65(m,2H),7.02(m,2H),7.25(m,2H),7.30–7.60(m,7H),7.70–7.81(m,3H),7.84–7.92(m,1H),8.08(d,1H).
example 17
Synthesis of Compound 178
Figure BDA0003829965200000163
The procedure of example 1 was repeated, except that the starting materials were changed to 32-A and 178-C. LC MS M/Z649.22 (M +). The total synthesis yield is as follows: 33%; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ3.42(m,1H),3.67(m,1H),6.88–7.02(m,2H),7.18(m,1H),7.27(m,1H),7.31–7.62(m,16H),7.77(m,1H),7.88(m,3H),8.08(m,1H).
example 18
Synthesis of Compound 182
Figure BDA0003829965200000171
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to 182-A and 182-C. LC MS M/Z541.25 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ0.94(d,6H),1.17–1.28(m,7H),1.49(d,1H),6.91–7.10(m,4H),7.23–7.29(m,1H),7.35(m,1H),7.39–7.50(m,2H),7.50–7.57(m,1H),7.78–7.89(m,1H),7.84–7.92(m,1H),7.96(m,1H),8.04–8.20(m,3H),8.67(m,1H),8.75–8.83(m,1H).
example 19
Synthesis of Compound 187
Figure BDA0003829965200000172
The procedure of example 1 was repeated, except that the starting materials were changed to 182-A and 182-C. LC MS M/Z690.30 (M +). The total synthesis yield is as follows: 32 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.13–1.29(m,2H),1.24–1.38(m,2H),1.41–1.72(m,6H),7.06(m,1H),7.09–7.21(m,2H),7.26(m,1H),7.30–7.62(m,21H),7.77(m,1H),7.88(m,1H),8.08(d,1H).
example 20
Synthesis of Compound 189
Figure BDA0003829965200000173
The procedure of example 1 was repeated, except that 189-A and 189-C were used as starting materials. LC MS M/Z655.31 (M +). The total synthesis yield is as follows: 31 percent; HPLC purity: 99.9 percent; 1 H NMR(400MHz,DMSO-d6)δ1.04–1.23(m,6H),1.25–1.36(m,2H),1.60(m,4H),1.77(m,2H),7.06(m,1H),7.09–7.21(m,2H),7.22–7.30(m,2H),7.35(m,2H),7.46(m,1H),7.52(m,3H),7.54–7.60(m,1H),7.60–7.71(m,4H),7.68–7.81(m,2H),7.84–7.92(m,1H),8.08(m,1H),8.18–8.26(m,2H),8.43–8.51(m,2H),8.70(t,1H).
device example 1: preparation of organic electroluminescent device
Figure BDA0003829965200000181
The preparation method of the organic electroluminescent device comprises the following steps: a glass substrate coated with Indium Tin Oxide (ITO) having a thickness of 100nm as a thin film was put in distilled water in which a detergent was dissolved, and ultrasonic cleaning was performed. After washing the ITO for 20 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each. After washing with distilled water, the substrate was cleaned with isopropyl alcohol, acetone and methanol by ultrasonic waves, and then dried and transferred to a plasma cleaner. Further, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum depositor. On the transparent ITO electrode prepared as above, a hole injection layer was formed by thermally vacuum-depositing compound HI at a deposition rate of 0.04 to 0.09nm/s and a total film thickness of 60nm, and then successively subjected to the following steps:
1) A compound HAT is vacuum-deposited on the hole injection layer as a first hole transport layer at a deposition rate of 0.04 to 0.09nm/s and at a total film thickness of 5nm.
2) And evaporating HT on the first hole transport layer in vacuum to form a second hole transport layer, wherein the evaporation rate is 0.04-0.09 nm/s, and the total thickness of the evaporated film is 50nm.
3) A light-emitting layer is formed on the 2 nd hole transport layer by vacuum deposition of a compound BH and a compound BD at a weight ratio of 25.
4) On the light emitting layer, a light emitting layer is formed by mixing, in a weight ratio of 1:1 the compound 1 and the compound LiQ were vacuum-deposited to form an electron transporting layer and an injection layer at a deposition rate of 0.1nm/s and a total deposition thickness of 35nm.
5) Lithium fluoride (LiF) was deposited on the electron injecting and transporting layer at a deposition rate of 0.03nm/s to a thickness of 1nm in total thickness, and then aluminum was deposited at a deposition rate of 0.2nm/s to a thickness of 100nm in total thickness to form a cathode.
The vacuum degree is maintained at 1 × 10 during the process -7 To 5X 10 -5 And (7) supporting.
Device examples 2 to 10
An organic electroluminescent device was fabricated in the same manner as in device example 1, except that compound 4, 13, 19, 32, 37, 53, 72, 75, 80, 95, 101, 106, 126, 147, 172, 178, 182, 187, and 189 were used instead of compound 1, respectively, in forming the electron transport layer.
Comparative device example 1
Figure BDA0003829965200000191
An organic electroluminescent device was fabricated in the same manner as in device example 1, except that in the formation of the light-emitting layer, compounds ET1 and ET2 were used instead of compound 1.
TABLE 1
Figure BDA0003829965200000192
From the results of table 1, it is understood that when the compound of the present invention is used as an electron transport layer of a light emitting device, voltage reduction can be achieved and current efficiency can be improved, instead of the electron transport materials ET1 and ET2 already commercialized in comparative devices 1 and 2. The results show that the compound shown as the formula (I) is used as an electron transport material of an organic electroluminescent device, is an organic luminescent functional material with good performance, and is expected to be popularized and commercialized.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.

Claims (10)

1. A compound having the chemical structure of formula (I):
Figure FDA0003829965190000011
in formula (I), A is selected from the group consisting of the following group structures:
Figure FDA0003829965190000012
X 1 -X 3 independently selected from O, S, -NR 16 -or-CR 17 R 18 -, where at most two are-CR 17 R 18 -, at most one is O;
Z 1 -Z 9 independently selected from O, S and-CR 19 R 20 -or-NR 21 -, and at least one in the same molecule is-CR 19 R 20 -；
* Is a linking site to B;
b is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
R 1 -R 8 and R 16 -R 21 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, and R 1 -R 8 At least one group structure selected from the group represented by formula (II):
Figure FDA0003829965190000013
e is an electron withdrawing group containing N or O;
L 1 and L 2 Selected from single bond, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.
2. The compound of claim 1, wherein in formula (ii), E is selected from the group consisting of the following structures:
Figure FDA0003829965190000014
Figure FDA0003829965190000021
wherein R is 11 -R 15 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;
n is selected from 1, 2,3 or 4.
3. The compound of claim 1, wherein the compound is selected from one or more of the following chemical structures:
Figure FDA0003829965190000022
Figure FDA0003829965190000031
Figure FDA0003829965190000041
Figure FDA0003829965190000051
4. an organic layer comprising the compound of any one of claims 1 to 3.
5. Use of a compound according to any one of claims 1 to 3 and/or an organic layer according to claim 4 in an organic opto-electronic device.
6. An organic optoelectronic device comprising a first electrode, a second electrode, and the organic layer of claim 4, wherein 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.
7. The organic optoelectronic device according to claim 6, wherein the electron transport layer material of the organic layer comprises one or more compounds according to any one of claims 1 to 3.
8. The organic optoelectronic device according to claim 6, wherein the material of the light-emitting layer of the organic layer comprises one or more compounds according to any one of claims 1 to 3.
9. The organic optoelectronic device according to any one of claims 6 to 7, wherein the organic optoelectronic device is at least one selected from the group consisting of an organic photovoltaic device, an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, and an organic thin film transistor.
10. A display or lighting device comprising the organic optoelectronic device of any one of claims 6 to 9.
CN202211070563.9A 2022-09-02 2022-09-02 Compound and application thereof in organic photoelectric device Withdrawn CN115304586A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211070563.9A CN115304586A (en) 2022-09-02 2022-09-02 Compound and application thereof in organic photoelectric device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211070563.9A CN115304586A (en) 2022-09-02 2022-09-02 Compound and application thereof in organic photoelectric device

Publications (1)

Publication Number Publication Date
CN115304586A true CN115304586A (en) 2022-11-08

Family

ID=83866378

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211070563.9A Withdrawn CN115304586A (en) 2022-09-02 2022-09-02 Compound and application thereof in organic photoelectric device

Country Status (1)

Country Link
CN (1) CN115304586A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115304498A (en) * 2022-09-02 2022-11-08 上海钥熠电子科技有限公司 Compound and application thereof in organic photoelectric device

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114133333A (en) * 2021-08-06 2022-03-04 陕西莱特迈思光电材料有限公司 Nitrogen-containing compound, electronic component, and electronic device
CN115304498A (en) * 2022-09-02 2022-11-08 上海钥熠电子科技有限公司 Compound and application thereof in organic photoelectric device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114133333A (en) * 2021-08-06 2022-03-04 陕西莱特迈思光电材料有限公司 Nitrogen-containing compound, electronic component, and electronic device
CN115304498A (en) * 2022-09-02 2022-11-08 上海钥熠电子科技有限公司 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
CN115304498A (en) * 2022-09-02 2022-11-08 上海钥熠电子科技有限公司 Compound and application thereof in organic photoelectric device

Similar Documents

Publication Publication Date Title
KR101982715B1 (en) Novel compound and organic light emitting device comprising the same
CN114805386B (en) Organic compound, host material, and organic photoelectric device
KR101512544B1 (en) New compound and organic light emitting device using the same
CN110878091B (en) Organic compound based on triazine and anthrone structure and application thereof
KR20110006915A (en) New compounds and organic electronic device using the same
CN111662309B (en) Compound with multi-heterocyclic structure and application thereof
CN114835590A (en) Organic compound and application thereof in organic photoelectric device
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
CN115304586A (en) Compound and application thereof in organic photoelectric device
CN115380099A (en) Organic light emitting compound and organic light emitting device including the same
CN115304498A (en) Compound and application thereof in organic photoelectric device
CN115448932A (en) Compound, organic photoelectric device and display or lighting device
CN116063187A (en) Compound and application thereof in organic photoelectric device
KR20180075914A (en) Novel amine-based compound and organic light emitting device comprising the same
CN116063267A (en) Spiro compound and application thereof
CN115141106B (en) Compound, organic material and organic photoelectric device
CN115109065B (en) Organic compound, host material, and organic electroluminescent device
CN115304574B (en) Heterocyclic compound and application thereof in organic electroluminescent device
CN115433193A (en) Compound and application thereof in organic photoelectric device
CN116082167A (en) Organic compound and application thereof in organic photoelectric device
CN115073307B (en) Fluorene compound and application thereof in organic electroluminescent device
CN114805370B (en) Indolocarbazole-based compound and application thereof in organic electroluminescent device
CN115504858A (en) 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
WW01 Invention patent application withdrawn after publication

Application publication date: 20221108

WW01 Invention patent application withdrawn after publication