WO2021093377A1 - 含光取出层材料的有机电致发光器件 - Google Patents

含光取出层材料的有机电致发光器件 Download PDF

Info

Publication number
WO2021093377A1
WO2021093377A1 PCT/CN2020/105574 CN2020105574W WO2021093377A1 WO 2021093377 A1 WO2021093377 A1 WO 2021093377A1 CN 2020105574 W CN2020105574 W CN 2020105574W WO 2021093377 A1 WO2021093377 A1 WO 2021093377A1
Authority
WO
WIPO (PCT)
Prior art keywords
atoms
groups
ring
group
substituted
Prior art date
Application number
PCT/CN2020/105574
Other languages
English (en)
French (fr)
Inventor
李涛
龙芷君
杨曦
宋晶尧
Original Assignee
广州华睿光电材料有限公司
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 广州华睿光电材料有限公司 filed Critical 广州华睿光电材料有限公司
Publication of WO2021093377A1 publication Critical patent/WO2021093377A1/zh

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/875—Arrangements for extracting light from the devices
    • H10K59/879—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than 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
    • C07C211/54—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
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/08—Aza-anthracenes
    • 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
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • 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
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • 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
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • 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
    • 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
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 hetero ring
    • 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
    • C07D251/22—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 two ring carbon atoms
    • 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
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D269/00—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00
    • C07D269/02—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00 having the hetero atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D417/14—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 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass

Definitions

  • This application relates to the field of organic electroluminescence technology, and in particular to an organic electroluminescence device containing a light extraction layer material.
  • the application further relates to an organic compound and its application in organic electroluminescence devices.
  • Organic electroluminescence display equipment is a type of self-luminous display device, which generates excitons through the transfer and recombination of carriers between various functional layers, and emits light by relying on organic compounds or metal complexes with high quantum efficiency. It has the characteristics of self-luminescence, high brightness, high efficiency, high contrast, and high responsiveness.
  • OLED generally adopts a top-emission structure that emits light from the upper part.
  • a light-emitting device when the light emitted in the light-emitting layer is incident on other functional layers, if it is incident at a certain angle or more, the light-emitting layer and other functional layers Total reflection occurs between the layers. Therefore, only part of the emitted light can be used.
  • a main purpose of this application is to provide an organic electroluminescent device containing a light extraction layer to improve the light extraction efficiency of the device.
  • This application further provides a new organic compound and its application in organic electroluminescent devices.
  • organic compounds with higher refractive index in electroluminescent devices need to meet the following types of conditions: high extinction coefficient in the ultraviolet band ( ⁇ 400nm) to avoid adverse effects of harmful light on the device materials; in the visible light range (>430nm), the extinction coefficient is close to 0, which has a higher effect on visible light. Transmittance reduces the impact on the light output efficiency of the device; it has a higher refractive index in the visible light range and has a small difference, which has the characteristics of improving light output and optimizing the device structure; it has a higher glass transition temperature and improves the thermal stability of the compound.
  • An organic electroluminescence device comprising two electrodes, one or more organic functional layers arranged between the two electrodes, and a light extraction layer arranged on the surface of one electrode and away from the organic functional layer.
  • the light extraction layer material contains a compound represented by the general formula (1):
  • L 1 , L 2 and L 3 are each independently selected from single bonds, substituted or unsubstituted aromatic groups or heteroaromatic groups with 5 to 30 ring atoms, or substituted or unsubstituted non-substituted or unsubstituted ring atoms with 3 to 30 Aromatic ring system;
  • Ar 1 is selected from electron withdrawing groups
  • Ar 2 is selected from substituted or unsubstituted fused ring aromatic groups or fused ring heteroaromatic groups with 10-30 ring atoms;
  • V is independently selected from CR 1 or N;
  • R 1 is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms Chain thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, and having 3 to 20 C atoms Branched or cyclic thioalkoxy groups, silyl groups, ketone groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxy groups having 7 to 20 C atoms Carbonyl, cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, cross Linked groups, substituted or unsubstitute
  • This application further relates to an organic compound selected from the structure shown in general formula (4):
  • L 1 and L 3 are each independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group with 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system with 3 to 30 ring atoms ;
  • L 2 is selected from a single bond or any one of the following groups:
  • Each occurrence of W and W 1 is independently selected from CR 9 or N;
  • R 9 , R 10 and R 11 is independently selected from: hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, having 1 to A straight-chain thioalkoxy group with 20 C atoms, a branched or cyclic alkyl group with 3 to 20 C atoms, a branched or cyclic alkoxy group with 3 to 20 C atoms, with 3 Branched or cyclic thioalkoxy groups having to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, having 7 to 20 C atoms C-atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, crosslinkable groups,
  • This application relates to a composition
  • a composition comprising at least one organic compound as described above and at least one organic solvent.
  • the present application relates to a light extraction layer material, which contains the above-mentioned organic compound.
  • the light extraction layer material according to the present application has a higher glass transition temperature, a higher thermal stability of the compound, a high extinction coefficient in the ultraviolet band, a small extinction coefficient in the visible light range, and a higher refractive index.
  • a higher glass transition temperature a higher thermal stability of the compound
  • a high extinction coefficient in the ultraviolet band a small extinction coefficient in the visible light range
  • a higher refractive index When used in an organic electroluminescent device, it can avoid harmful light's adverse effects on the internal materials of the device and improve the efficiency of visible light extraction.
  • FIG. 1 is a schematic diagram of an embodiment of a device.
  • Figure 1 is a structural diagram of a light-emitting device according to an embodiment of the present application.
  • 1 is a substrate
  • 2 is an anode
  • 3a is a hole injection layer (HIL)
  • 3b is a hole transport layer (HTL)
  • 3c is a light emitting layer.
  • 3d is the electron transport layer (ETL)
  • EIL electron injection layer
  • 4 is the cathode
  • 5 is the light extraction layer.
  • Figure 2 is an ultraviolet-visible absorption spectrum of compound C2 in dichloromethane
  • Figure 3 is a mass spectrum of compound C2.
  • the present application provides an organic electroluminescence device containing a triarylamine compound of triphenylene as a material of the light extraction layer.
  • This application also relates to an organic compound containing triphenylene.
  • substitution means that the hydrogen atom in the substituted group is replaced by the substituent.
  • substituted or unsubstituted means that the defined group may be substituted or unsubstituted.
  • a group is substituted, as defined, should be understood to be optionally substituted by a group accepted in the art, including but not limited to: C 1 - 30 alkyl group, a cycloalkyl group having 3 to 20 ring atoms, comprising Heterocyclic groups with 3-20 ring atoms, aryl groups with 5-20 ring atoms, heteroaryl groups with 5-20 ring atoms, silyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, amino groups Formyl, haloformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro or halogen, and
  • the above-mentioned groups can also be further substituted with substituents
  • the number of ring atoms means the number of structural compounds (for example, monocyclic compounds, condensed ring compounds, cross-linked compounds, carbocyclic compounds, heterocyclic compounds) obtained by synthesizing a cyclic atom bond to form the ring itself The number of atoms among atoms.
  • the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms.
  • the number of ring atoms of the benzene ring is 6
  • the number of ring atoms of the naphthalene ring is 10
  • the number of ring atoms of the thienyl group is 5.
  • adjacent groups means that these groups are bonded to the same carbon atom or bonded to adjacent carbon atoms. These definitions apply correspondingly to "adjacent substituents”.
  • the aromatic group refers to a hydrocarbon group containing at least one aromatic ring.
  • a heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. Further, the heteroatom is selected from Si, N, P, O, S, and/or Ge, and further, is selected from Si, N, P, O, and/or S.
  • a fused-ring aromatic group means that the ring of an aromatic group can have two or more rings, in which two carbon atoms are shared by two adjacent rings, that is, a fused ring.
  • the fused heterocyclic aromatic group refers to a fused ring aromatic hydrocarbon group containing at least one heteroatom.
  • aromatic groups or heteroaromatic groups include not only aromatic ring systems but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are for the purpose of this application , Is also considered to be an aromatic group or a heterocyclic aromatic group.
  • fused-ring aromatic or fused heterocyclic aromatic ring systems not only include systems of aromatic groups or heteroaromatic groups, but also multiple aromatic groups or heterocyclic aromatic groups can be shortened
  • Non-aromatic units are discontinuous ( ⁇ 10% of non-H atoms, and further less than 5% of non-H atoms, such as C, N or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc., are also considered to be fused-ring aromatic ring systems for the purpose of this application.
  • the fused ring aromatic group is selected from: naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, naphthacene, pyrene, benzopyrene, acenaphthene , Fluorene, and its derivatives; fused ring heteroaromatic groups are selected from benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, Furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, naphthalene, quinoxaline, phenanthridine, primidine, quinazoline, quinoline Oxazolinone, and its derivatives.
  • the "light extraction layer” is a layer located on the surface of the electrode of the organic electroluminescence device and away from the organic functional layer.
  • An organic electroluminescence device comprising two electrodes, one or more organic functional layers arranged between the two electrodes, and a light extraction layer arranged on the surface of one electrode and away from the organic functional layer.
  • the light extraction layer material contains a compound represented by the general formula (1):
  • L 1 , L 2 and L 3 are each independently selected from single bonds, substituted or unsubstituted aromatic groups or heteroaromatic groups with 5 to 30 ring atoms, or substituted or unsubstituted non-substituted or unsubstituted ring atoms with 3 to 30 Aromatic ring system;
  • Ar 1 is selected from electron withdrawing groups
  • Ar 2 is selected from substituted or unsubstituted fused ring aromatic groups with 10-30 ring atoms or fused ring heteroaromatic groups; the molar refractive index of the fused ring is relatively high, which is effective Increase the refractive index of molecules;
  • Each occurrence of V is independently selected from CR 1 or N; optionally, each occurrence of V is independently selected from CR 1 ;
  • R 1 is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms Chain thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, and having 3 to 20 C atoms Branched or cyclic thioalkoxy groups, silyl groups, ketone groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxy groups having 7 to 20 C atoms Carbonyl, cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, cross Linked groups, substituted or unsubstitute
  • Ar 2 is selected from substituted or unsubstituted fused ring aromatic groups or fused ring heteroaromatic groups with 14-30 ring atoms; in one embodiment, Ar 2 is selected from substituted or unsubstituted A fused-ring aromatic group with 14-30 ring atoms;
  • Ar 2 is selected from any group (A-1)-(A-5):
  • Each occurrence of X is independently selected from CR 2 or N; when X and L 2 are connected, X is selected from C; alternatively, each occurrence of X is selected from CR 2 ;
  • R 2 is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms Chain thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, and having 3 to 20 C atoms Branched or cyclic thioalkoxy groups, silyl groups, ketone groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxy groups having 7 to 20 C atoms Carbonyl, cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, cross Linked groups, substituted or unsubstitute
  • Ar 2 is selected from (A-1), (A-2) or (A-4); further, Ar 2 is selected from (A-1).
  • Ar 2 is selected from any of the following groups, wherein the H atom on the ring may be further substituted:
  • Ar 2 is selected from
  • Ar 2 is selected from Furthermore, Ar 2 is selected from Furthermore, Ar 2 is selected from
  • the general formula (1) is selected from any structure of general formulas (2-1)-(2-4):
  • V in the general formulas (2-1)-(2-4) are all selected from CR 1 ; further, R 1 is selected from H; in one embodiment, the general formulas (2-1)-( In 2-4), X is all selected from CR 2 ; further, R 2 is selected from H; in one embodiment, V in general formulas (2-1)-(2-4) are all selected from CR 1 , and X are all selected Since CR 2 .
  • the general formulas (2-1)-(2-4) are selected from the following general formulas:
  • Ar 1 is selected from electron withdrawing groups; the reason is that it can increase the electronic push and pull of the entire molecule, regulate the energy level and dipole moment of the molecule, and increase the ultraviolet absorption of the molecule below 400 nm and the refractive index of the molecule.
  • Ar 1 is selected from any of the following groups:
  • Each occurrence of X 1 is independently selected from CR 3 or N, and at least one X 1 is selected from N; in one embodiment, at least two X 1 are selected from N;
  • R 3 , R 4 and R 5 is independently selected from: hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, having 1 to A straight-chain thioalkoxy group with 20 C atoms, a branched or cyclic alkyl group with 3 to 20 C atoms, a branched or cyclic alkoxy group with 3 to 20 C atoms, with 3 Branched or cyclic thioalkoxy groups having to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, having 7 to 20 C atoms C-atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, crosslinkable groups,
  • Ar 1 is selected from Furthermore, Ar 1 is selected from Furthermore, Ar 1 is selected from
  • Ar 1 is selected from any of the following groups, and the dashed line indicates the connection site:
  • Ar 1 is selected from any of the following groups:
  • the H atom on the ring can be further substituted.
  • Ar 1 is selected from any one of the following groups, the H atom on the ring may be further substituted, and the dotted line indicates the connection site:
  • the general formula (1) is selected from the general formula (3-1) or (3-2):
  • V in general formula (3-1) or (3-2) is selected from CR 1 ; further, R 1 is selected from H; in one embodiment, general formula (3-1) or ( In 3-2), X is all selected from CR 2 ; further, R 2 is selected from H; in one embodiment, V in general formula (3-1) or (3-2) is all selected from CR 1 , and X is all selected Since CR 2 .
  • the general formula (3-1) or (3-2) is selected from the following general formulas:
  • the H atom on the ring can be further substituted.
  • the general formula (3-1) is selected from the following general formulas:
  • V, X, X 1 , R 3 , R 4 , L 1 , L 2 , L 3 are as defined above.
  • L 1 , L 2 and L 3 are each independently selected from a single bond or any one of the following groups:
  • Each occurrence of X 2 is independently selected from CR 6 or N;
  • R 6 , R 7 and R 8 is independently selected from: hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, having 1 to A straight-chain thioalkoxy group with 20 C atoms, a branched or cyclic alkyl group with 3 to 20 C atoms, a branched or cyclic alkoxy group with 3 to 20 C atoms, with 3 Branched or cyclic thioalkoxy groups having to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, having 7 to 20 C atoms C-atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, crosslinkable groups,
  • L 1, L 2 and L 3 is selected from at least one of a single bond; In one embodiment, L 1, L 2 and L 3 is selected from at least two single bonds; In one embodiment, , L 1 , L 2 and L 3 are all selected from single bonds.
  • At least one of L 1 , L 2 and L 3 is selected from In an embodiment, at least two of L 1 , L 2 and L 3 In one embodiment, L 1 , L 2 and L 3 are all selected from
  • At least one of L 1 , L 2 and L 3 is selected from In an embodiment, at least two of L 1 , L 2 and L 3 are selected from In one embodiment, L 1 , L 2 and L 3 are all selected from
  • L 1 , L 2 and L 3 are all selected from single bonds or In an embodiment , at least one of L 1 , L 2 and L 3 is selected from a single bond and at least one is selected from In an embodiment, one of L 1 , L 2 and L 3 is selected from a single bond, and two are selected from In one embodiment, two of L 1 , L 2 and L 3 are selected from single bonds, and one is selected from
  • X 2 referred to above is selected from CR 6 ; further, R 6 is selected from H.
  • L 1 , L 2 and L 3 are each independently selected from any one of the following groups:
  • the H atom on the ring can be further substituted.
  • L 1 , L 2 and L 3 are each independently selected from a single bond or any one of the following groups, and the dashed line indicates the connection site:
  • the H atom on the ring can be further substituted.
  • the light extraction layer material is selected from the following structures but not limited to:
  • the light extraction layer material needs a higher glass transition temperature to improve the thermal stability of the light extraction layer material.
  • the glass transition temperature Tg ⁇ 100°C, in an alternative embodiment, Tg ⁇ 120°C, in a more alternative embodiment, Tg ⁇ 140°C, in an alternative embodiment, Tg ⁇ 140°C, In a more optional embodiment, Tg is greater than or equal to 160°C, and in a most optional embodiment, Tg is greater than or equal to 180°C.
  • the refractive index of the light extraction layer material at a wavelength of 630 nm is greater than 1.7; optionally, greater than 1.78; more optionally, greater than 1.83.
  • the singlet energy (S1) of the light extraction layer material is greater than or equal to 2.7 eV; alternatively, greater than or equal to 2.8 eV; more optionally , Greater than or equal to 2.85eV.
  • the singlet energy (S1) of the light extraction layer material is less than or equal to 3.1 eV; alternatively, less than or equal to 3.0 eV;
  • the light extraction layer material needs a small extinction coefficient, and the extinction coefficient at a wavelength of 430 nm is less than 0.1; optionally, less than 0.003; more optionally, less than 0.001. It has a high transmittance to visible light, which reduces the impact on the light output efficiency of the device.
  • the light extraction layer has a larger extinction coefficient in a wavelength range of ⁇ 400nm; preferably, the extinction coefficient at a wavelength of 350nm is ⁇ 0.3 ; Preferably ⁇ 0.5, more preferably ⁇ 0.7, most preferably ⁇ 1.0.
  • the organic electroluminescent device includes one or more organic functional layers, and the organic functional layers are selected from the group consisting of electron injection layers, electron transport layers, and hole blocking layers.
  • the organic functional layers are selected from the group consisting of electron injection layers, electron transport layers, and hole blocking layers.
  • the organic electroluminescent device wherein the organic functional layer is selected from the group consisting of a hole transport layer, a light emitting layer, and an electron transport layer.
  • the organic electroluminescent device wherein the organic functional layer is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer .
  • the organic electroluminescent device wherein the light-emitting material in the light-emitting layer is selected from a singlet light-emitting body, a triplet light-emitting body or a TADF material.
  • the singlet emitter, triplet emitter and TADF material will be described in more detail below (but not limited to this).
  • Singlet emitters often have longer conjugated ⁇ -electron systems. So far, there have been many examples, such as styrylamine and its derivatives disclosed in JP2913116B and WO2001021729A1, indenofluorene and its derivatives disclosed in WO2008/006449 and WO2007/140847, and disclosed in US7233019 and KR2006-0006760 The triarylamine derivative of pyrene.
  • the singlet luminophore can be selected from monostyrylamine, distyrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether and aromatic amine.
  • a monostyrylamine refers to a compound that contains an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine.
  • a dibasic styrylamine refers to a compound that contains two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a ternary styrylamine refers to a compound that contains three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a quaternary styrylamine refers to a compound that contains four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • An optional styrene is stilbene, which may be further substituted.
  • the corresponding definitions of phosphines and ethers are similar to those of amines.
  • An arylamine or aromatic amine refers to a compound containing three unsubstituted or substituted aromatic rings or heterocyclic ring systems directly connected to the nitrogen. At least one of these aromatic or heterocyclic ring systems is preferred to the fused ring system, and preferably has at least 14 aromatic ring atoms.
  • aromatic anthracene amine refers to a compound in which a dibasic aryl amine group is directly linked to the anthracene, preferably at the 9 position.
  • aromatic anthracene diamine refers to a compound in which two divalent aryl amine groups are directly linked to the anthracene, preferably at the 9,10 position.
  • Aromatic pyrene amine, aromatic pyrene diamine, aromatic pyrene diamine and aromatic pyrene diamine have similar definitions, in which the divalent aryl amine group is preferably linked to the 1, or 1, 6 position of the pyrene.
  • Examples of singlet emitters based on vinylamine and aromatic amine are also optional examples, which can be found in the following patent documents: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/115610, US 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006/210830 A, EP 1957606 A1 and US 2008/0113101 A1
  • the entire contents of the patent documents listed above are hereby Incorporated into this article for reference
  • luminophores can be selected from indenofluorene-amine and indenofluorene-diamine, as disclosed in WO 2006/122630, benzindenofluorene-amine and benzindenofluorene-diamine Amines, as disclosed in WO 2008/006449, dibenzoindenofluorene-amine and dibenzoindenofluorene-diamine, as disclosed in WO2007/140847.
  • singlet light emitters can be selected from fluorene-based fused ring systems, such as those disclosed in US2015333277A1, US2016099411A1, and US2016204355A1.
  • More optional singlet luminophores can be selected from derivatives of pyrene, such as the structure disclosed in US2013175509A1; triarylamine derivatives of pyrene, such as triarylamine derivatives of pyrene containing dibenzofuran units disclosed in CN102232068B; Other triarylamine derivatives of pyrene with specific structures are disclosed in CN105085334A and CN105037173A.
  • polycyclic aromatic hydrocarbon compounds especially derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthanthracene), naphthalene, tetraphenyl, xanthene, phenanthrene , Pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, phenylene such as (4,4'-bis(9-ethyl-3-carbazole vinyl)-1 ,1'-biphenyl), diindenopyrene, decacycloene, hexabenzocene, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylene ethylene (such as US5121029, US5130603), cyclopentadiene Alkenes such as tetraphenylcyclopentadiene, rubrene,
  • anthracene such as 9,10-bis
  • Triplet emitters are also called phosphorescent emitters.
  • the triplet emitter is a metal complex with the general formula M(L)n, where M is a metal atom, and each occurrence of L can be the same or different. It is an organic ligand, It is bonded or coordinated to the metal atom M through one or more positions, and n is an integer between 1 and 6.
  • the triplet luminophore contains a chelating ligand, that is, a ligand, which is coordinated to the metal through at least two binding points. It is particularly preferred that the triplet luminophore contains two or three identical or different doublets. Tooth or multidentate ligands. Chelating ligands help to improve the stability of metal complexes.
  • the metal complexes that can be used as triplet emitters have the following forms:
  • the metal atom M is selected from transition metal elements or lanthanides or actinides, preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Re, Cu, Ag, Ni, Co, W or Eu, especially preferred Ir, Au, Pt, W or Os.
  • Ar 4 , Ar 5 can be the same or different each time, it is a cyclic group, where Ar 4 contains at least one donor atom, that is, an atom with a lone pair of electrons, such as nitrogen, through which the cyclic group and the metal Coordination connection; where Ar 5 contains at least one carbon atom, through which the cyclic group is connected to the metal; Ar 4 and Ar 5 are linked together by covalent bonds, each of which can carry one or more substituent groups, and they also It can be linked together by substituent groups; L'can be the same or different each time, it is a bidentate chelating auxiliary ligand, preferably a monoanionic bidentate chelating ligand; q1 can be 0,1 , 2 or 3, preferably 2 or 3; q2 can be 0, 1, 2 or 3, preferably 1 or 0.
  • organic ligands may be selected from phenylpyridine derivatives or 7,8-benzoquinoline derivatives. All these organic ligands may be substituted, for example by alkyl chains or fluorine or silicon.
  • the auxiliary ligand may preferably be selected from acetone acetate or picric acid.
  • triplet emitters Some examples of the materials and applications of triplet emitters can be found in the following patent documents and documents: WO200070655, WO200141512, WO200202714, WO200215645, WO2005033244, WO2005019373, US20050258742, US20070087219, US20070252517, US2008027220, WO2009146770, US20090061681, WO20090061681, WO20090061681, WO20090061681, WO20090151180 , WO2010054731, WO2011157339, WO2012007087, WO201200708, WO2013107487, WO2013094620, WO2013174471, WO 2014031977, WO 2014112450, WO2014007565, WO 2014024131, Baldo et al.
  • TDF Thermally activated delayed fluorescence luminescent material
  • Such materials generally have a small singlet-triplet energy level difference ( ⁇ Est), and the triplet excitons can be converted into singlet excitons to emit light through the inter-system crossing. This can make full use of the singlet and triplet excitons formed under electrical excitation.
  • the quantum efficiency in the device can reach 100%.
  • the material structure is controllable, the properties are stable, the price is cheap, no precious metals are needed, and the application prospects in the OLED field are broad.
  • the TADF material needs to have a small singlet-triplet energy level difference, preferably ⁇ Est ⁇ 0.3eV, next best ⁇ Est ⁇ 0.2eV, and most preferably ⁇ Est ⁇ 0.1eV.
  • the TADF material has a relatively small ⁇ Est, and in another preferred embodiment, TADF has a better fluorescence quantum efficiency.
  • TADF light-emitting materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et.al.Adv.Mater., 21, 2009, 4802, Adachi, et.al.Appl.Phys.Lett., 98, 2011,083302, Adachi, et.al.Appl.Phys.Lett., 101, 2012 ,093306,Adachi,et.al.Chem.Commun.,48,2012,11392,Adachi,et.al.Nature Photonics,6,2012,253,Adachi,et.al.Nature,492,2012,234,Adachi , Et.al.J.Am.Chem.Soc, 134, 2012, 14706, Adachi,
  • TADF luminescent materials Some examples of suitable TADF luminescent materials are listed below:
  • the cathode, anode and light extraction layer of the device structure of the organic light emitting diode are described below, but not limited thereto.
  • the anode may include a conductive metal or metal oxide, or a conductive polymer.
  • the anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light emitting layer.
  • the absolute value of the difference between the work function of the anode and the luminous body in the light-emitting layer or the HOMO energy level or the valence band energy level of the p-type semiconductor material as HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, most preferably less than 0.2 eV.
  • anode materials include but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum doped zinc oxide (AZO), and the like.
  • suitable anode materials are known, and those of ordinary skill in the art can easily select and use them.
  • the anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the anode is patterned and structured. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.
  • the cathode may include a conductive metal or metal oxide.
  • the cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer.
  • the work function of the cathode and the LUMO energy level or conductivity of the luminous body in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL)
  • the absolute value of the difference in band level is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV.
  • all materials that can be used as the cathode of an OLED can be used as the cathode material of the device of this application.
  • cathode materials include, but are not limited to: Al, Au, Ag, Ca , Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO and the like.
  • the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the light extraction layer material needs to have a suitable energy level structure, which has strong absorption in the region with a wavelength less than 400nm, and visible light with a wavelength greater than 400nm absorbs weakly or close to zero, so as to prevent the internal materials of the device from being damaged by high-energy light in the subsequent process.
  • the light extraction layer material has a relatively high refractive index, which can beneficially derive the emission of visible light and improve the luminous efficiency of the organic electronic light-emitting device.
  • the refractive index of the material constituting the light extraction layer can be selected to be greater than the refractive index of the adjacent electrode, and the refractive index is at 630 nm. More than 1.50 is sufficient, more optional is more than 1.70, especially optional is more than 1.80.
  • the thickness of the organic compound of the light extraction layer is generally 10nm to 200nm, preferably 20nm to 150nm, more preferably 30nm to 100nm, most preferably 40nm to 90nm.
  • the light extraction layer is disposed on the surface of the cathode and away from the organic functional layer. In other embodiments, the light extraction layer is disposed on the surface of the anode and away from the organic functional layer.
  • the present application also relates to the application of the electroluminescent device according to the present application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and so on.
  • This application further relates to an organic compound selected from the structure shown in general formula (4):
  • L 1 and L 3 are each independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group with 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system with 3 to 30 ring atoms ;
  • L 2 is selected from a single bond or the following groups:
  • Each occurrence of W and W 1 is independently selected from CR 9 or N;
  • R 9 , R 10 and R 11 is independently selected from: hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, having 1 to A straight-chain thioalkoxy group with 20 C atoms, a branched or cyclic alkyl group with 3 to 20 C atoms, a branched or cyclic alkoxy group with 3 to 20 C atoms, with 3 Branched or cyclic thioalkoxy groups having to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, having 7 to 20 C atoms C-atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, crosslinkable groups,
  • At least one of W is selected from N. further, Selected from Further, Selected from The dotted line indicates the connection site.
  • Each occurrence of W is independently selected from CR 9 .
  • connection site any one of the following groups is selected, the dotted line indicates the connection site:
  • the H atom on the ring may be further substituted, and the dotted line indicates the connection site:
  • the general formula (4) is selected from any one of the general formulas (5-1)-(5-6):
  • W in general formulas (5-1)-(5-6) are all selected from CR 9 ; more optionally, R 9 is selected from H.
  • L 2 is selected from a single bond or any one of the following groups:
  • L 2 is selected from a single bond or In one embodiment, L 2 is selected from a single bond or In one embodiment, L 2 is selected from a single bond or benzene; in one embodiment, L 2 is selected from a single bond.
  • L 1 and L 3 are each independently selected from a single bond or any one of the following groups:
  • Each occurrence of X 2 is independently selected from CR 6 or N;
  • R 6 , R 7 and R 8 is independently selected from: hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, having 1 to A straight-chain thioalkoxy group with 20 C atoms, a branched or cyclic alkyl group with 3 to 20 C atoms, a branched or cyclic alkoxy group with 3 to 20 C atoms, with 3 Branched or cyclic thioalkoxy groups having to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, having 7 to 20 C atoms C-atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF 3 , Cl, Br, F, crosslinkable groups,
  • L 1 and L 3 are each independently selected from any one of the following groups:
  • the H atom on the ring can be further substituted.
  • L 1 , L 2 and L 3 are each independently selected from a single bond or any one of the following groups, and the dashed line indicates the connection site:
  • the H atom on the ring can be further substituted.
  • L 1, L 2 and L 3 is selected from at least one of a single bond; In one embodiment, L 1, L 2 and L 3 is selected from at least two single bonds; In one embodiment, , L 1 , L 2 and L 3 are all selected from single bonds. In one embodiment, L 1 is a single bond; in one embodiment, L 3 is a single bond; in one embodiment, L 1 and L 3 are single bonds;
  • At least one of L 1 , L 2 and L 3 is selected from benzene or naphthalene; in one embodiment, at least two of L 1 , L 2 and L 3 are selected from benzene or naphthalene; in one embodiment , L 1 , L 2 and L 3 are all selected from benzene or naphthalene.
  • L 1 , L 2 and L 3 is selected from benzene; in one embodiment, L 1 , L 2 and L 3 are at least two benzenes; in one embodiment, L 1 , L 2 And L 3 are all selected from benzene. In one embodiment, L 3 is benzene; in one embodiment, L 2 is benzene; in one embodiment, L 1 and L 3 are benzene.
  • L 1 , L 2 and L 3 are all selected from single bonds or benzene; more alternatively, at least one is selected from single bonds and at least one is selected from benzene; more alternatively, one is selected from single bonds , Two are selected from benzene; more alternatively, two are selected from single bonds and one is selected from benzene. In one embodiment, L 1 and L 3 are single bonds, and L 2 is benzene.
  • the organic compound described in this application is selected from any one of the above-mentioned structural formulas (G-145)-(G-211), but is not limited thereto.
  • organic compounds described in this application can be used not only in the light extraction layer of organic electronic devices, but also in other organic functional layers, such as electron injection layer, electron transport layer, hole injection layer, hole transport layer and luminescence Floor.
  • a light extraction layer material contains the organic compound as described above.
  • One purpose of this application is to provide material solutions for vapor-deposited OLEDs.
  • the organic compound according to the present application has a molecular weight ⁇ 1200g/mol, optionally ⁇ 1100g/mol, very optionally ⁇ 1000 g/mol, more optionally ⁇ 950g/mol, most optionally ⁇ 900g /mol.
  • This application also relates to a composition
  • a composition comprising at least one organic compound represented by the above general formula (4) and at least one organic solvent; the at least one organic solvent is selected from aromatic hydrocarbons or heteroaromatics , Ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefin compound, or borate or phosphate compound, or a mixture of two or more solvents.
  • the application still further relates to an organic electronic device comprising at least one compound as described above.
  • the organic electronic device described in this application can be selected from, but not limited to, organic light-emitting diodes (OLED), organic photovoltaic cells, organic light-emitting batteries, organic field effect tubes, organic light-emitting field effect tubes, organic lasers, organic spintronics Devices, organic sensors and organic plasmon emitting diodes, etc., especially OLEDs.
  • Dissolve compound 1-3 (3.73g, 6mmol) in anhydrous toluene, add 1-4 (0.92g, 6mmol), sodium tert-butoxide (1.73g, 18mmol) and dipalladium tridibenzylideneacetone (0.16 g, 0.18mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (0.18mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source.
  • p-bromoaniline 10g, 58.5mmol
  • potassium carbonate 73g, 175mmol
  • tetrakis(triphenylphosphine) palladium 2g, 1.76mmol
  • Compound 6-3 (6g, 11.2mmol) and 2-2 (3.43g, 11.2mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (3.3g, 33.6mmol) and dipalladium tridibenzylidene acetone were added (0.31g, 0.34mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (0.34mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source.
  • Compound 13-2 (6.21g, 10mmol) was dissolved in anhydrous toluene, 7-1 (2.73g, 10mmol), sodium tert-butoxide (2.88g, 30mmol) and dipalladium tridibenzylidene acetone (0.28 g, 0.3 mmol), after replacing nitrogen for three times, add tri-tert-butyl phosphine (0.3 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source.
  • the compound was vapor-deposited on monocrystalline silicon to form a 50nm thin film by vacuum evaporation.
  • the monocrystalline silicon was placed on the ellipsometer (ES-01) sample stage with an incident angle of 70°.
  • the test was an atmospheric environment.
  • the extinction coefficient of the compound ( The test results of k) and refractive index (n) are fitted by ellipsometer.
  • the compound of the present application has weak absorption in the visible light waveband and high absorption in the ultraviolet waveband, and can resist the damage of external high-energy light to the inside of the device.
  • a higher refractive index can ensure a better light extraction effect.
  • the preparation steps are as follows:
  • the hole injection layer material HATCN is evaporated by vacuum evaporation method, the thickness is 5nm, and the evaporation rate is On the hole injection layer, the hole transport material SNFFB is vapor-deposited by a vacuum vapor deposition method to a thickness of 80 nm.
  • a light-emitting layer is vapor-deposited on the hole transport layer, m-CP is used as the host material, Ir(p-ppy) 3 is used as the doping material, and the mass ratio of Ir(p-ppy) 3 and m-CP is 1:9 , The thickness is 30nm.
  • the electron transport material NaTzF 2 was vapor-deposited by a vacuum vapor deposition method to a thickness of 30 nm.
  • the electron injection layer LiF is vacuum-evaporated to a thickness of 1 nm. This layer is the electron injection layer 7.
  • the cathode Mg:Ag layer is vacuum-evaporated, the Mg:Ag doping ratio is 9:1, and the thickness is 15nm.
  • the light extraction layer compound C-2 was vapor-deposited by a vacuum vapor deposition method to a thickness of 60 nm.
  • Example 12 The light extraction layer compound of the organic electroluminescence device was changed to C-5.
  • Example 14 The light extraction layer compound of the organic electroluminescence device was changed to C-14.
  • Example 15 The light extraction layer compound of the organic electroluminescence device was changed to C-15.
  • the structure of the compound involved in the device is as follows:
  • the luminous efficiency in Table 2 is the relative value obtained when the current density is 10 mA/cm 2. It can be seen from Table 2 that compared with the comparative example, the compound of the present application as a light extraction layer can effectively improve the luminous efficiency of the organic electroluminescent device. Furthermore, the organic electroluminescent device with C-2, C-7, C-12, and C-13 as the light extraction layer in the compound of the present application has better luminous efficiency.

Landscapes

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

Abstract

为了改善有机电致发光器件的器件性能，特别是光取出效率，本申请提供一种包含光取出层的有机电致发光器件，其中光取出层材料选自含有三亚苯及吸电子基团的三芳胺化合物。本申请提供的光取出材料在在紫外区域具有较高的消光系数，在可见光区域拥有较高的折射率，它能降低外部高能量光对有机电致发光显示设备内部材料的损害，并提升光取出率，提高器件的发光效率。

Description

含光取出层材料的有机电致发光器件
相关申请
本申请要求2019年11月12日申请的，申请号为201911098682.3，名称为“一种含光取出层材料的有机电致发光器件”的中国专利申请的优先权，在此将其全文引入作为参考。
技术领域
本申请涉及有机电致发光技术领域，尤其涉及一种含光取出层材料的有机电致发光器件。本申请进一步涉及一种有机化合物及其在有机电致发光器件中的应用。
背景技术
有机电致发光显示设备是一类自发光型的显示装置，通过载流子在各个功能层间的转移、复合产生激子，依靠高量子效率的有机化合物或金属配合物发光。其具有自发光、高亮度、高效率、高对比度、高响应性等特点。
近些年，有机电致发光二极管(OLED)的发光效率有了很大的提升，但是其内部量子效率已经接近理论极限。因此提高光取出效率成为进一步提高器件稳定性和电流效率的有效手段(如发射层金属配合物的堆积、各功能层间折射率的匹配等)。
OLED一般采用从上部进行发光的顶部发射结构，在这样的发光器件中，在发光层中所发出的光入射到其他功能层的情况下，如果以某角度以上入射，则在发光层与其他功能层之间发生全反射。因此，只能利用发出的光的一部分。近年来，为了提高光的取出效率，提出了在折射率底的半透明电极的外侧设置一层光取出层。如在2001年，Hung等人在金属阴极的表面覆盖了一层约50nm的有机化合物或无机化合物，通过控制厚度及折射率以提高器件的表现性能。在2003年，Riel等人已尝试将具有高折射率(n＝2.6)的无机化合物ZnSe蒸镀于阴极上，利用功能层之间折射率的差异提高光取出效率，但受限于无机材料蒸发温度高、蒸发速率慢等原因，这类化合物并未在有机电致发光器件中得到更多应用。
因此，新一类的提高有机电致发光器件光取出效率的材料需要被进一步开发。
发明内容
鉴于上述现有技术的不足，本申请的一个主要目的在于提供一种含有光取出层的有机电致发光器件，用以提高器件光取出效率。本申请进一步提供一种新的有机化合物及其在有机电致发光器件中的应用。
鉴于上述原因，可以尝试将有具有较高折射率有机化合物用于电致发光器件中以提高光取出效率。此类化合物需满足以下几类条件：在紫外波段(＜400nm)消光系数高，避免有害光对器件材料的不利影响；在可见光范围(>430nm)消光系数接近于0，对可见光有较高的透射率，降低对设备出光效率的影响；在可见光范围内具有较高折射率并且差异较小，具有提高出光和优化器件结构等特点；有较高的玻璃化温度，提升化合物的热稳定性。
本申请的技术方案如下：
一种有机电致发光器件，包含两个电极，设置在所述两个电极之间的一个或多个有机功能层和设置于一电极表面且远离有机功能层一侧的光取出层，所述光取出层材料包含如通式(1)所示的化合物：
Figure PCTCN2020105574-appb-000001
其中：
L 1、L 2和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取代或未取代的环原子数3至30的非芳香环系；
Ar 1选自吸电子基团；Ar 2选自取代或未取代的环原子数为10-30的稠环芳香基团或稠环杂芳香基团；
V每次出现分别独立选自CR 1或N；
R 1每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
本申请进一步涉及一种有机化合物，选自如通式(4)所示的结构：
Figure PCTCN2020105574-appb-000002
其中：
L 1和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取代或未取代的环原子数3至30的非芳香环系；
L 2选自单键或者以下基团中的任一种：
Figure PCTCN2020105574-appb-000003
W、W 1每次出现分别独立选自CR 9或N；
Y 2、Y 3每次出现分别独立选自NR 10、CR 10R 11、O、S、SiR 10R 11、S＝O、SO 2或PR 10；
R 9、R 10和R 11每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
本申请涉及一种组合物，包含有至少一种上所述的有机化合物，及至少一种有机溶剂。
本申请涉及一种光取出层材料，包含上述的有机化合物。
有益效果：
按照本申请所述的光取出层材料具有较高的玻璃化温度，化合物的热稳定性较高，在紫外波段消光系数高，在可见光范围消光系数较小，并具备较高的折射率。当用于有机电致发光器件中时，能避免有害光对器件内部材料的不利影响，并提高可见光出光效率。
附图说明
图1是一器件实施例的示意图。图1是按照本申请的一个实施例的发光器件结构图，图中1是基板，2是阳极，3a是空穴注入层(HIL)，3b是空穴传输层(HTL)，3c是发光层，3d是电子传输层(ETL)，3e是电子注入层(EIL)，4是阴极，5是光取出层。
图2是化合物C2在二氯甲烷中的紫外可见吸收光谱图；
图3是化合物C2的质谱图。
具体实施方式
本申请提供一种包含三亚苯的三芳胺化合物作为光取出层的材料的有机电致发光器件。本申请还涉及一种含三亚苯的有机化合物。为使本申请的目的、技术方案及效果更加清楚、明确，以下对本申请进一步详细说明。应当理解，此处所描述的具体实施例仅用以解释本申请，并不用于限定本申请。
在本申请中，“取代”表示被取代基中的氢原子被取代基所取代。
在本申请中，“取代或未取代”表示所定义的基团可以被取代，也可以不被取代。当所定义的基团被取代时，应理解为任选被本领域可接受的基团所取代，包括但不限于：C 1- 30烷基、含有3-20个环原子的环烷基、含有3-20个环原子的杂环基、含有5-20个环原子的芳基、含有5-20个环原子的杂芳基、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、-NRR′、氰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基、硝基或卤素，且上述基团也可以进一步被本领域可接受取代基取代；可理解的，-NRR′中的R和R′各自独立地为本领域可接受的基团所取代，包括但不限于H、C 1- 6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基；所述C 1- 6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基任选进一步被一个或多个以下基团取代：C 1- 6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、卤素、羟基、硝基或氨基。
在本申请中，“环原子数”表示原子键合成环状而得到的结构化合物(例如，单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时，取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”，在没有特别说明的条件下也是同样的。例如，苯环的环原子数为6，萘环的环原子数为10，噻吩基的环原子数为5。
在本申请中，“相邻基团”是指这些基团键合至同一碳原子或键合至相邻的碳原子上。这些定义相应的适用于“相邻取代基”。
芳香基团指至少包含一个芳环的烃基。杂芳香基团指包含至少一个杂原子的芳香烃基。进一步地，杂原子选自Si、N、P、O、S和/或Ge，更进一步地，选自Si、N、P、O和/或S。稠环芳香基团指芳香基团的环可以具有两个或多个环，其中两个碳原子被两个相邻的环共用，即稠环。稠杂环芳香基团指包含至少一个杂原子的稠环芳香烃基。对于本申请的目的，芳香基团或杂芳香基团不仅包括芳香环的体系，而且包含非芳香族的环系。因此，比如吡啶、噻吩、吡咯、吡唑、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、吡嗪、哒嗪、嘧啶、三嗪、卡宾等体系，出于本申请的目的，同样认为是芳香基团或杂环芳香基团。对于本申请的目的，稠环芳香族或稠杂环芳香族环系不仅包括芳香基团或杂芳香基团的体系，而且，其中多个芳香基团或杂环芳香基团也可以被短的非芳族单元间断(<10％的非H原子，进一步为小于5％的非H原子，比如C、N或O原子)。因此，比如9，9'-螺二芴，9，9-二芳基芴，三芳胺，二芳基醚等体系，出于本申请的目的，同样认为是稠环芳香族环系。
在某个可选地实施例中，所述的稠环芳香基团选自：萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯、并四苯、芘、苯并芘、苊、芴、及其衍生物；稠环杂芳香基团选自苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、及其衍生物。
在本申请中，“光取出层”位于有机电致发光器件的电极表面且远离有机功能层一侧的层。
一种有机电致发光器件，包含两个电极，设置在所述两个电极之间的一个或多个有机功能层和设置于一电极表面且远离有机功能层一侧的光取出层，所述光取出层材料包含如通式(1)所示的化合物：
Figure PCTCN2020105574-appb-000004
其中：
L 1、L 2和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取 代或未取代的环原子数3至30的非芳香环系；
Ar 1选自吸电子基团；Ar 2选自取代或未取代的环原子数为10-30的稠环芳香基团或稠环杂芳香基团；稠环的摩尔折射度较高，可有效提高分子的折射率；
V每次出现分别独立选自CR 1或N；可选地，V每次出现独立选自CR 1；
R 1每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
在一实施例中，Ar 2选自取代或未取代的环原子数为14-30的稠环芳香基团或稠环杂芳香基团；在一实施例中，Ar 2选自取代或未取代的环原子数为14-30的稠环芳香基团；
在一实施例中，Ar 2选自(A-1)-(A-5)的任一基团：
Figure PCTCN2020105574-appb-000005
其中：
X每次出现分别独立选自CR 2或N；当X与L 2连接时，X选自C；可选地，X每次出现选自CR 2；
R 2每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
进一步地，Ar 2选自(A-1)、(A-2)或(A-4)；更进一步地，Ar 2选自(A-1)。
在一实施例中，Ar 2选自如下基团中的任一种，其中环上的H原子可以进一步被取代：
Figure PCTCN2020105574-appb-000006
进一步，Ar 2选自
Figure PCTCN2020105574-appb-000007
进一步，Ar 2选自
Figure PCTCN2020105574-appb-000008
更进一步，Ar 2选自
Figure PCTCN2020105574-appb-000009
在一实施例中，通式(1)选自通式(2-1)-(2-4)任一结构：
Figure PCTCN2020105574-appb-000010
其中：X、V、L 1、L 2和L 3、Ar 1含义同上所述。
在一实施例中，通式(2-1)-(2-4)中V均选自CR 1；进一步，R 1选自H；在一实施例中，通式(2-1)-(2-4)中X均选自CR 2；进一步，R 2选自H；在一实施例中，通式(2-1)-(2-4)中V均选自CR 1，X均选自CR 2。
在一实施例中，通式(2-1)-(2-4)选自如下通式：
Figure PCTCN2020105574-appb-000011
在一实施例中，Ar 1选自吸电子基团；原因在于可以提高整个分子的电子推拉，调控分子的能级及偶极矩，提高分子在波长400nm以下的紫外吸收和分子的折射率。
进一步，Ar 1选自如下基团中的任一种：
Figure PCTCN2020105574-appb-000012
其中：
X 1每次出现分别独立选自CR 3或N，且至少一个X 1选自N；在一实施例中，至少2个X 1选自N；
Y每次出现分别独立选自NR 4、CR 4R 5、O、S、SiR 4R 5、S＝O、SO 2或PR 4；
R 3、R 4和R 5每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
进一步地，Ar 1选自
Figure PCTCN2020105574-appb-000013
更进一步地，Ar 1选自
Figure PCTCN2020105574-appb-000014
在一可选地实施例中，Ar 1选自以下基团中的任一种，虚线表示连接位点：
Figure PCTCN2020105574-appb-000015
在一可选地实施例中，Ar 1选自以下基团中的任一种：
Figure PCTCN2020105574-appb-000016
其中：环上的H原子可以进一步被取代。
更优地，Ar 1选自以下基团中的任一种，环上的H原子可以进一步被取代，虚线表示连接位点：
Figure PCTCN2020105574-appb-000017
在一实施例中，通式(1)选自通式(3-1)或(3-2)：
Figure PCTCN2020105574-appb-000018
在一实施例中，通式(3-1)或(3-2)中V均选自CR 1；进一步，R 1选自H；在一实施例中，通式(3-1)或(3-2)中X均选自CR 2；进一步，R 2选自H；在一实施例中，通式(3-1)或(3-2)中V均选自CR 1，X均选自CR 2。
在一实施例中，通式(3-1)或(3-2)选自如下通式：
Figure PCTCN2020105574-appb-000019
其中：环上的H原子可以进一步被取代。
在一实施例中，通式(3-1)选自如下通式：
Figure PCTCN2020105574-appb-000020
其中：V，X，X 1，R 3，R 4，L 1，L 2，L 3定义同上所述。
在一实施例中，L 1、L 2和L 3分别独立选自单键或以下基团中的任一种：
Figure PCTCN2020105574-appb-000021
其中：
X 2每次出现分别独立选自CR 6或N；
Y 1每次出现分别独立选自NR 7、CR 7R 8、O、S、SiR 7R 8、S＝O、SO 2或PR 7；
R 6、R 7和R 8每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
在一实施例中，L 1、L 2和L 3中至少一个选自单键；在一实施例中，L 1、L 2和L 3中至少两个选自单键；在一实施例中，L 1、L 2和L 3均选自单键。
在一实施例中，L 1、L 2和L 3中至少一个选自
Figure PCTCN2020105574-appb-000022
在一实施例中，L 1、L 2和L 3中至少两个
Figure PCTCN2020105574-appb-000023
在一实施例中，L 1、L 2和L 3均选自
Figure PCTCN2020105574-appb-000024
在一实施例中，L 1、L 2和L 3中至少一个选自
Figure PCTCN2020105574-appb-000025
在一实施例中，L 1、L 2和L 3中至少两个选自
Figure PCTCN2020105574-appb-000026
在一实施例中，L 1、L 2和L 3均选自
Figure PCTCN2020105574-appb-000027
在一实施例中，L 1、L 2和L 3均选自单键或
Figure PCTCN2020105574-appb-000028
在一实施例中，L 1、L 2和L 3中至少一个选自 单键且至少一个选自
Figure PCTCN2020105574-appb-000029
在一实施例中，L 1、L 2和L 3中一个选自单键，两个选自
Figure PCTCN2020105574-appb-000030
在一实施例中，L 1、L 2和L 3中两个选自单键，一个选自
Figure PCTCN2020105574-appb-000031
在一实施例中，上述涉及的X 2选自CR 6；进一步，R 6选自H。
在一实施例中，L 1、L 2和L 3分别独立选自以下基团中的任一种：
Figure PCTCN2020105574-appb-000032
其中：环上的H原子可以进一步被取代。
具体地，L 1、L 2和L 3分别独立选自单键或以下基团中的任一种，虚线表示连接位点：
Figure PCTCN2020105574-appb-000033
其中：环上的H原子可以进一步被取代。
具体地，按照本申请所述的有机电致发光器件，其中光取出层材料选自如下结构但不限于：
Figure PCTCN2020105574-appb-000034
Figure PCTCN2020105574-appb-000035
Figure PCTCN2020105574-appb-000036
Figure PCTCN2020105574-appb-000037
Figure PCTCN2020105574-appb-000038
Figure PCTCN2020105574-appb-000039
其中：以上结构中的H可以进一步被任意取代。
按照本申请所述的有机电致发光器件，光取出层材料需要较高的玻璃化温度，提升光取出层材料的热稳定性。在某些可选的实施例中，其玻璃化温度Tg≥100℃，在一个可选的实施例中，Tg≥120℃，在一个较为可选的实施例中，Tg≥140℃，在一个更为可选的实施例中，Tg≥160℃，在一个最为可选的实施例中，Tg≥180℃。
在某些实施例中，按照本申请所述的有机电致发光器件，光取出层材料在波长630nm处的折射率大于1.7；可选地，大于1.78；更可选地，大于1.83。
在另一些实施例中，按照本申请所述的有机电致发光器件，光取出层材料单线态能量(S1)要大于或等于2.7eV；可选地，大于或等于2.8eV；更可选地，大于或等于2.85eV。
在另一些实施例中，按照本申请所述的有机电致发光器件，光取出层材料单线态能量(S1)要小于或等于3.1eV；可选地，小于或等于3.0eV；
按照本申请所述的有机电致发光器件，光取出层材料需要较小的消光系数，在波长为430nm时的消光系数小于0.1；可选地，小于0.003；更可选地，小于0.001。对可见光有较高的透射率，降低对设备出光效率的影响。
在某些可选的实施方案中，按照本申请的有机电致发光器件，其光取出层在≤400nm的波长范围有较大的消光系数；优先的，在波长为350nm时的消光系数≥0.3；较好是≥0.5，更好是≥0.7，最好是≥1.0。
在可选的实施例中，按照本申请所述的有机电致发光器件，其中包括一个或者更多个有机功能层，所述的有机功能层选自电子注入层、电子传输层、空穴阻挡层、空穴注入层、空穴传输层、电子阻挡层和发光层的一个或多个层，其中至少包含一个发光层。
在某些较优先的实施例中，按照本申请所述的有机电致发光器件，其中所述有机功能层选自空穴传输层、发光层和电子传输层。
在某些更优先的实施例中，按照本申请所述的有机电致发光器件，其中所述有机功能层选自空穴注入层、空穴传输层、发光层、电子传输层和电子注入层。
在某些可选的实施例中，按照本申请所述的有机电致发光器件，其中所述发光层中的发光材料选自单重态发光体、三重态发光体或者TADF材料。
下面对单重态发光体、三重态发光体及TADF材料作一些较详细描述(但不限于此)。
1.单重态发光体
单重态发光体往往有较长的共轭π电子系统。迄今,已有许多例子，例如在JP2913116B和WO2001021729A1中公开的苯乙烯胺及其衍生物，在WO2008/006449和WO2007/140847中公开的茚并芴及其衍生物及在US7233019、KR2006-0006760中公开的芘的三芳胺衍生物。
在一个优先的实施方案中,单重态发光体可选自一元苯乙烯胺，二元苯乙烯胺，三元苯乙烯胺，四元苯乙烯胺，苯乙烯膦，苯乙烯醚和芳胺。
一个一元苯乙烯胺是指一化合物,它包含一个无取代或取代的苯乙烯基组和至少一个胺，最好是芳香胺。一个二元苯乙烯胺是指一化合物,它包含二个无取代或取代的苯乙烯基组和至少一个胺，最好是芳香胺。一个三元苯乙烯胺是指一化合物,它包含三个无取代或取代的苯乙烯基组和至少一个胺，最好是芳香胺。一个四元苯乙烯胺是指一化合物,它包含四个无取代或取代的苯乙烯基组和至少一个胺，最好是芳香胺。一个可选的苯乙烯是二苯乙烯,其可能会进一步被取代。相应的膦类和醚类的定义与胺类相似。芳基胺或芳香胺是指一种化合物，包含三个直接联接氮的无取代或取代的芳香环或杂环系统。这些芳香族或杂环的环系统中至少有一个优先选于稠环系统，并最好有至少14个芳香环原子。其中可选的例子有芳香蒽胺，芳香蒽二胺，芳香芘胺，芳香芘二胺，芳香屈胺和芳香屈二胺。一个芳香蒽胺是指一化合物，其中一个二元芳基胺基团直接联到蒽上,最好是在9的位置上。一个芳香蒽二胺是指一化合物，其中二个二元芳基胺基团直接联到蒽上,最好是在9,10的位置上。芳香芘胺，芳香芘二胺，芳香屈胺和芳香屈二胺的定义类似,其中二元芳基胺基团最好联到芘的1或1,6位置上.
基于乙烯胺及芳胺的单重态发光体的例子,也是可选的例子,可在下述专利文件中找到:WO 2006/000388,WO 2006/058737,WO 2006/000389,WO 2007/065549,WO 2007/115610,US 7250532 B2,DE 102005058557 A1,CN 1583691 A,JP 08053397 A,US 6251531 B1,US 2006/210830 A,EP 1957606 A1和US 2008/0113101 A1特此上述列出的专利文件中的全部内容并入本文作为参考。
基于均二苯乙烯极其衍生物的单重态发光体的例子有US 5121029。
进一步的可选的单重态发光体可选于茚并芴-胺和茚并芴-二胺，如WO 2006/122630所公开的，苯并茚并芴-胺和苯并茚并芴-二胺，如WO 2008/006449所公开的，二苯并茚并芴-胺和二苯并茚并芴-二胺，如WO2007/140847所公开的。
进一步可选的单重态发光体可选于基于芴的稠环体系，如US2015333277A1、US2016099411A1、US2016204355A1所公开的。
更加可选的单重态发光体可选于芘的衍生物，如US2013175509A1所公开的结构；芘的三芳胺衍生物，如CN102232068B所公开的含有二苯并呋喃单元的芘的三芳胺衍生物；其它具有特定结构的芘的三芳胺衍生物，如CN105085334A、CN105037173A所公开的。其他可用作单重态发光体的材料有多环芳烃化合物，特别是如下化合物的衍生物:蒽如9,10-二(2-萘并蒽)，萘,四苯，氧杂蒽，菲,芘(如2,5,8,11-四-t-丁基苝)，茚并芘，苯撑如(4,4’-双(9-乙基-3-咔唑乙烯基)-1,1’-联苯)，二茚并芘,十环烯,六苯并苯,芴，螺二芴,芳基芘(如US20060222886)，亚芳香基乙烯(如US5121029，US5130603),环戊二烯如四苯基环戊二烯,红荧烯，香豆素，若丹明，喹吖啶酮，吡喃如4(二氰基亚甲基)-6-(4-对二甲氨基苯乙烯基-2-甲基)-4H-吡喃(DCM),噻喃,双(吖嗪基)亚胺硼化合物(US 2007/0092753 A1),双(吖嗪基)亚甲基化合物,carbostyryl化合物,噁嗪酮,苯并恶唑,苯并噻唑,苯并咪唑及吡咯并吡咯二酮。一些 单重态发光体的材料可在下述专利文件中找到:US 20070252517 A1,US 4769292,US 6020078,US 2007/0252517 A1,US 2007/0252517 A1。特此将上述列出的专利文件中的全部内容并入本文作为参考。
下面的表中列出一些合适的单重态发光体的例子：
Figure PCTCN2020105574-appb-000040
2.三重态发光体
三重态发光体也称磷光发光体。在一个优先的实施方案中，三重态发光体是具有通式M(L)n的金属络合物，其中M是一金属原子，L每次出现可以是相同或不同，是一有机配体，它通过一个或多个位置键接或配位连接到金属原子M上，n是1至6之间的整数。优先地，三重态发光体包含有螯合配体，即配体，通过至少两个结合点与金属配位，特别优先考虑的是三重态发光体包含有两个或三个相同或不同的双齿或多齿配体。螯合配体有利于提高金属络合物的稳定性。在一个优先的实施方案中，可用作三重态发光体的金属络合物有如下形式：
Figure PCTCN2020105574-appb-000041
金属原子M选于过渡金属元素或镧系元素或锕系元素，优先选择Ir，Pt，Pd，Au，Rh，Ru，Os，Re，Cu，Ag，Ni，Co，W或Eu，特别优先选择Ir，Au，Pt，W或Os。
Ar 4，Ar 5每次出现可以是相同或不同，是一个环状基团，其中Ar 4至少包含有一个施主原子，即有一孤对电子的原子，如氮，通过它环状基团与金属配位连接；其中Ar 5至少包含有一个碳原子，通过它环状基团与金属连接；Ar 4和Ar 5由共价键联接在一起，可各自携带一个或多个取代基团，它们也可再通过取代基团联接在一起；L’每次出现可以是相同或不同，是一个双齿螯合的辅助配体，最好是单阴离子双齿螯合配体；q1可以是0，1，2或3，优先地是2或3；q2可以是0，1，2或3，优先地是1或0。有机配体的例子可选自苯基吡啶衍生物或7，8-苯并喹啉衍生物。所有这些有机配体都可能被取代，例如被烷基鏈或含氟或硅取代。辅助配体可优先选自乙酸丙酮或苦味酸。
一些三重态发光体的材料极其应用的例子可在下述专利文件和文献中找到:WO200070655，WO200141512，WO200202714，WO200215645，WO2005033244，WO2005019373，US20050258742，US20070087219，US20070252517，US2008027220，WO2009146770，US20090061681，US20090061681，WO2009118087，WO2010015307，WO2010054731，WO2011157339，WO2012007087，WO201200708，WO2013107487，WO2013094620，WO2013174471，WO 2014031977，WO 2014112450，WO2014007565，WO 2014024131，Baldo et al.Nature(2000)，750，Adachi et al.Appl.Phys.Lett.(2001)，1622，Kido et al.Appl.Phys.Lett.(1994)，2124，Wrighton et al.J.Am.Chem.Soc.(1974)，998，Ma et al.Synth.Metals(1998)，245。特此将上述列出的专利文件和文献中的全部内容并入本文作为参考。在下面的表中列出一些合适的三重态发光体的例子：
Figure PCTCN2020105574-appb-000042
3.热激活延迟荧光发光材料(TADF)
传统有机荧光材料只能利用电激发形成的25％单线态激子发光，器件的内量子效率较低(最高为25％)。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间穿越，可以有效利用电激发形成的单线态激子和三线态激子发光，使器件的内量子效率达到100％。但磷光材料昂贵，材料稳定性差，器件效率滚降严重等问题限制了其在OLED中的应用。热激活延迟荧光发光材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(ΔEst)，三线态激子可以通过反系间穿越转变成单线态激子发光。这可以充分利用电激发下形成的单线态激子和三线态激子。器件内量子效率可达到100％。同时材料结构可控，性质稳定，价格便宜无需要贵金属，在OLED领域的应用前景广阔。
TADF材料需要具有较小的单线态-三线态能级差，较好是ΔEst<0.3eV，次好是ΔEst<0.2eV，最好是ΔEst<0.1eV。在一个优先的实施方案中，TADF材料有比较小的ΔEst，在另一个优先的实施方案中，TADF有较好的荧光量子效率。一些TADF发光的材料可在下述专利文件中找到:CN103483332(A)，TW201309696(A)，TW201343874(A)，TW201350558(A)，US20120217869(A1)，WO2013133359(A1)，WO2013154064(A1)，Adachi，et.al.Adv.Mater.，21，2009，4802，Adachi，et.al.Appl.Phys.Lett.，98，2011，083302，Adachi，et.al.Appl.Phys.Lett.，101，2012，093306，Adachi，et.al.Chem.Commun.，48，2012，11392，Adachi，et.al.Nature Photonics，6，2012，253，Adachi，et.al.Nature，492，2012，234，Adachi，et.al.J.Am.Chem.Soc，134，2012，14706，Adachi，et.al.Angew.Chem.Int.Ed，51，2012，11311，Adachi，et.al.Chem.Commun.，48，2012，9580，Adachi，et.al.Chem.Commun.，48，2013，10385，Adachi，et.al.Adv.Mater.，25，2013，3319，Adachi，et.al.Chem.Mater.，25，2013，3038，Adachi，et.al.Chem.Mater.，25，2013，3766，Adachi，et.al.J.Mater.Chem.C.，1，2013，4599，Adachi，et.al.J.Phys.Chem.A.，117，2013， 5607，特此将上述列出的专利或文章文件中的全部内容并入本文作为参考。
在下面列出一些合适的TADF发光材料的例子：
Figure PCTCN2020105574-appb-000043
下面对有机发光二极管的器件结构阴极、阳极和光取出层做一描述，但不限于此。
阳极可包含一导电金属或金属氧化物，或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中，阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV，较好是小于0.3eV，最好是小于0.2eV。阳极材料的例子包含但不限于：Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的，本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积，如一合适的物理气相沉积法，包含射频磁控溅射，真空热蒸发，电子束(e-beam)等。在某些实施例中，阳极是图案结构化的。图案化的ITO导电基板可在市场上买到，并且可以用来制备根据本申请的器件。
阴极可包含一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个实施例中，阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV，较好是小于0.3eV，最好是小于0.2eV。原则上，所有可用作OLED的阴极的材料都可能作为本申请器件的阴极材料。阴极材料的例子包含但不限于：Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF 2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积，如一合适的物理气相沉积法，包含射频磁控溅射，真空热蒸发，电子束(e-beam)等。
光取出层材料需要有合适能级结构，在波长小于400nm的区域有较强的吸收，波长大于400nm的可见光则吸收弱或接近零，避免器件内部材料在后续过程中受到高能光线照射而造成损伤。同时，光取出层材料拥有较高的折射率，能够对可见光的发射进行有益导出，提高有机电子发光器件的发光效率。光取出层材料与相邻电极之间的界面的反射率大时，光干涉的影响大，因此构成光取出层材料的折射率可选大于相邻的电极的折射率，折射率在630nm处为1.50以上即可，更可选的是1.70以上，特别可选的是1.80以上。
在一些更为可选的实施例中，按照本申请的有机电致发光器件，一般光取出层有机化合物厚度为10nm至200nm，较好为20nm至150nm，更好为30nm至100nm，最好为40nm至90nm。
在一些实施例中，光取出层设置在阴极表面且远离有机功能层一侧。在另一些实施例中，光取出层设置在阳极表面且远离有机功能层一侧。
本申请还涉及按照本申请的电致发光器件在各种电子设备中的应用，包含，但不限于，显示设备， 照明设备，光源，传感器等等。
本申请进一步涉及一种有机化合物，选自如通式(4)所示的结构：
Figure PCTCN2020105574-appb-000044
其中：
L 1和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取代或未取代的环原子数3至30的非芳香环系；
L 2选自单键或者以下基团：
Figure PCTCN2020105574-appb-000045
W、W 1每次出现分别独立选自CR 9或N；
Y 2、Y 3每次出现分别独立选自NR 10、CR 10R 11、O、S、SiR 10R 11、S＝O、SO 2或PR 10；
R 9、R 10和R 11每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
在一实施例中，
Figure PCTCN2020105574-appb-000046
中至少一个W选自N。进一步地，
Figure PCTCN2020105574-appb-000047
选自
Figure PCTCN2020105574-appb-000048
更进一步，
Figure PCTCN2020105574-appb-000049
选自
Figure PCTCN2020105574-appb-000050
虚线表示连接位点。
在一实施例中，
Figure PCTCN2020105574-appb-000051
中W每次出现分别独立选自CR 9。
进一步，
Figure PCTCN2020105574-appb-000052
选自以下基团中的任一种，虚线表示连接位点：
Figure PCTCN2020105574-appb-000053
在一实施例中，
Figure PCTCN2020105574-appb-000054
选自以下基团中的任一种，环上的H原子可以进一步被取代，虚线表示连接位点：
Figure PCTCN2020105574-appb-000055
在一实施例中，通式(4)选自通式(5-1)-(5-6)任意一种：
Figure PCTCN2020105574-appb-000056
更可选地，通式(5-1)-(5-6)中W均选自CR 9；更更可选地，R 9选自H。
在一实施例中，L 2选自单键或者以下基团中的任一种：
Figure PCTCN2020105574-appb-000057
在一实施例中，L 2选自单键或者
Figure PCTCN2020105574-appb-000058
在一实施例中，L 2选自单键或者
Figure PCTCN2020105574-appb-000059
在一实施例中，L 2选自单键或苯；在一实施例中，L 2选自单键。
在一实施例中，L 1和L 3分别独立选自单键或以下基团中的任一种：
Figure PCTCN2020105574-appb-000060
其中：
X 2每次出现分别独立选自CR 6或N；
Y 1每次出现分别独立选自NR 7、CR 7R 8、O、S、SiR 7R 8、S＝O、SO 2或PR 7；
R 6、R 7和R 8每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
在一实施例中，L 1和L 3分别独立选自以下基团中的任一种：
Figure PCTCN2020105574-appb-000061
其中：环上的H原子可以进一步被取代。
具体地，L 1、L 2和L 3分别独立选自单键或以下基团中的任一种，虚线表示连接位点：
Figure PCTCN2020105574-appb-000062
其中：环上的H原子可以进一步被取代。
在一实施例中，L 1、L 2和L 3中至少一个选自单键；在一实施例中，L 1、L 2和L 3中至少两个选自单键；在一实施例中，L 1、L 2和L 3均选自单键。在一实施例中，L 1为单键；在一实施例中，L 3为单键；在一实施例中，L 1和L 3为单键；
在一实施例中，L 1、L 2和L 3至少一个选自苯或萘；在一实施例中，L 1、L 2和L 3至少两个选自苯或萘；在一实施例中，L 1、L 2和L 3均选自苯或萘。
在一实施例中，L 1、L 2和L 3至少一个选自苯；在一实施例中，L 1、L 2和L 3至少两个苯；在一实施例中，L 1、L 2和L 3均选自苯。在一实施例中，L 3为苯；在一实施例中，L 2为苯；在一实施例中，L 1和L 3为苯。
在一实施例中，L 1、L 2和L 3均选自单键或苯；更可选地，至少一个选自单键且至少一个选自苯；更可选地，一个选自单键，两个选自苯；更可选地，两个选自单键，一个选自苯。在一实施例中，L 1和L 3为单键，L 2为苯。
具体地，按照本申请所述的有机化合物，选自如上所述的结构式(G-145)-(G-211)任意一种，但不限于此。
按照本申请所述的有机化合物，不仅可以运用于有机电子器件光取出层，也可以用于其它有机功能层，例如：电子注入层、电子传输层、空穴注入层、空穴传输层和发光层。
一种光取出层材料，包含如上所述的有机化合物。
本申请的一个目的是为蒸镀型OLED提供材料解决方案。
在某些实施例中，按照本申请的有机化合物，其分子量≤1200g/mol，可选≤1100g/mol，很可选≤1000 g/mol，更可选≤950g/mol，最可选≤900g/mol。
本申请还涉及一种组合物，包含至少一种如上通式(4)所示的有机化合物，及至少一种有机溶剂；所述的至少一种的有机溶剂选自芳族烃或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物，或硼酸酯或磷酸酯类化合物，或两种及两种以上溶剂的混合物。
本申请还进一步涉及包含至少一种如上所述的化合物的有机电子器件。按照本申请所述的有机电子器件可选于，但不限于，有机发光二极管(OLED)，有机光伏电池，有机发光电池，有机场效应管，有机发光场效应管，有机激光器，有机自旋电子器件，有机传感器及有机等离激元发射二极管等，特别可选为OLED。
下面将结合可选实施例对本申请进行了说明，但本申请并不局限于下述实施例，应当理解，所附权利要求概括了本申请的范围在本申请构思的引导下本领域的技术人员应意识到，对本申请的各实施例所进行的一定的改变，都将被本申请的权利要求书的精神和范围所覆盖。
具体实施例
按照本申请的化合物的合成方法举例，但本申请并不局限于下述实施例。
化合物C-1的合成：
Figure PCTCN2020105574-appb-000063
将化合物1-1(4.86g，15mmol)、1-2(8.16g，30mmol)、碳酸钾(6.26g，45mmol)、四(三苯基膦)钯(0.52g，0.45mmol)置于有甲苯和甲醇(体积比3：1)的三颈烧瓶中，置换氮气三次，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到4.19g化合物I-3，产率45％。
将化合物1-3(3.73g，6mmol)溶解在无水甲苯中，加入1-4(0.92g，6mmol)，叔丁醇钠(1.73g，18mmol)及三二亚苄基丙酮二钯(0.16g，0.18mmol)，置换氮气三次后，加入三叔丁基膦(0.18mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到2.88g化合物C-1，产率65％。m/z＝738.6
化合物C-2的合成：
Figure PCTCN2020105574-appb-000064
将化合物2-1(2.6g，9.7mmol)、2-2(7.7g,25.2mmol)溶解在100mL无水甲苯中，加入叔丁醇钠(4.8g，50mmol)及三二亚苄基丙酮二钯(0.28g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到5.6g化合物C-2，产率72％。m/z＝678.5
化合物C-3的合成：
Figure PCTCN2020105574-appb-000065
将化合物3-1(3.1g，10.9mmol)、2-2(7.3g，24mmol)溶解在无水甲苯中，叔丁醇钠(4.8g，50mmol)及三二亚苄基丙酮二钯(0.28g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到4.2g化合物C-3，产率53％。m/z＝737.3
化合物C-4的合成：
Figure PCTCN2020105574-appb-000066
将4-1(10g，58mmol)与4-2(8.9g，58mmol)置于多聚磷酸中，升温至160℃，搅拌反应约12小时。待冷却至室温后，低温下加入氢氧化钠水溶液中和，减压抽滤得到中间体4-3共14.3g，产率85％。
将中间体4-3(14.3g，9.7mmol)溶解在四氢呋喃与甲醇的100mL混合溶液中，加入3倍量的二水合氯化亚硒(6.75g，30mmol)，升温至70℃。搅拌反应12小时，待体系冷却后加入碳酸氢钠水溶液，用乙酸乙酯萃取，合并有机相，无水硫酸钠干燥。减压下浓缩过硅胶柱得到中间体4-4共9.5g，产率74％。
将中间体4-4(5g，19.2mmol)、2-2(12.8g，42mmol)溶解在80mL无水甲苯中，叔丁醇钠(5.8g，60mmol)及三二亚苄基丙酮二钯(0.55g，0.6mmol)，置换氮气三次后，加入三叔丁基膦(0.6mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到6.2g化合物C-4，产率45％。m/z＝712.5
化合物C-5的合成：
Figure PCTCN2020105574-appb-000067
将9-菲硼酸(13g，58.5mmol)、对溴苯胺(10g，58.5mmol)、碳酸钾(73g，175mmol)、四(三苯基膦)钯(2g，1.76mmol)置于有甲苯和甲醇(体积比3：1)的三颈烧瓶中，置换氮气三次，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体5-1共13.5g，产率86％。
将化合物5-1(10g，37.1mmol)、2-2(11.35g，37.1mmol)溶解在无水甲苯中，加入叔丁醇钠(10.7g，111mmol)及三二亚苄基丙酮二钯(1g，1.11mmol)，置换氮气三次后，加入三叔丁基膦(1.11mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体5-2共10.3g，产率56％。
将化合物5-2(8g，16.2mmol)、5-3(3.8g，16.2mmol)溶解在无水甲苯中，加入叔丁醇钠(4.7g，48.6mmol)、及三二亚苄基丙酮二钯(0.41g，0.5mmol)，置换氮气三次后，加入三叔丁基膦(0.5mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到8.2g化合物C-5，产率共78％。m/z＝648.9
化合物C-6的合成：
Figure PCTCN2020105574-appb-000068
将化合物6-1(8g，36.4mmol)、6-2(14.3g，36.4mmol)溶解在无水甲苯中，加入叔丁醇钠(10.5g，109mmol)及三二亚苄基丙酮二钯(1g，1.1mmol)，置换氮气三次后，加入三叔丁基膦(1.1mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体6-3共9.2g，产率47％。
将化合物6-3(6g，11.2mmol)、2-2(3.43g，11.2mmol)溶解在无水甲苯中，加入叔丁醇钠(3.3g，33.6mmol)及三二亚苄基丙酮二钯(0.31g，0.34mmol)，置换氮气三次后，加入三叔丁基膦(0.34mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到得到6.6g化合物C-6，产率77％。m/z＝761.2
化合物C-7的合成：
Figure PCTCN2020105574-appb-000069
将化合物7-1(1.7g，6.1mmol)、5-2(3g，6.1mmol)溶解在无水甲苯中，加入叔丁醇钠(1.76g，18.3mmol)及三二亚苄基丙酮二钯(0.17g，0.18mmol)，置换氮气三次后，加入三叔丁基膦(0.18mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到3.6g化合物C-7，产率86％。m/z＝688.7
化合物C-8的合成：
Figure PCTCN2020105574-appb-000070
将化合物8-1(2.9g，20mmol)、2-2(6.12g，20mmol)溶解在无水甲苯中，加入叔丁醇钠(5.76g，60mmol)、及三二亚苄基丙酮二钯(0.55g，0.6mmol)，置换氮气三次后，加入三叔丁基膦(0.6mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体8-2共4.58g，产率62％。
将中间体8-3(3.79g，12mmol)、8-2(4.43g，12mmol)溶解在无水甲苯中，加入叔丁醇钠(3.46g，36mmol)及三二亚苄基丙酮二钯(0.33g，0.36mmol)，置换氮气三次后，加入三叔丁基膦(0.36mmol)， 逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到得到5.37g化合物C-8，产率69％。m/z＝649.9
化合物C-9的合成：
Figure PCTCN2020105574-appb-000071
将化合物9-1(2.89g，10mmol)、5-2(4.95g，10mmol)溶解在无水甲苯中，加入叔丁醇钠(2.88g，30mmol)及三二亚苄基丙酮二钯(0.28g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶得到5.98g化合物C-9，产率85％。m/z＝704.6
化合物C-10的合成：
Figure PCTCN2020105574-appb-000072
将化合物10-1(2.38g，8mmol)、2-2(5.51g，18mmol)溶解在无水甲苯中，加入叔丁醇钠(2.3g，24mmol)及三二亚苄基丙酮二钯(0.22g，0.24mmol)，置换氮气三次后，加入三叔丁基膦(0.24mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到3.30g化合物C-10，产率55％。m/z＝749.7
化合物C-11的合成：
Figure PCTCN2020105574-appb-000073
将化合物11-1(4.79g，15mmol)、2-2(4.59g，15mmol)溶解在无水甲苯中，加入叔丁醇钠(4.32g，45mmol)及三二亚苄基丙酮二钯(0.41g，0.45mmol)，置换氮气三次后，加入三叔丁基膦(0.45mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体11-2共4.74g，产率58％。
将中间体11-2(4.36g，8mmol)、11-3(1.82g，8mmol)溶解在无水甲苯中，加入叔丁醇钠(2.30g，24mmol)及三二亚苄基丙酮二钯(0.22g，0.24mmol)，置换氮气三次后，加入三叔丁基膦(0.24mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到2.65g化合物C-11，产率45％。m/z＝737.7
化合物C-12的合成：
Figure PCTCN2020105574-appb-000074
将中间体11-2(4.36g，8mmol)、12-1(2.32g，8mmol)溶解在无水甲苯中，加入叔丁醇钠(2.30g，24mmol)及三二亚苄基丙酮二钯(0.22g，0.24mmol)，置换氮气三次后，加入三叔丁基膦(0.24mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到4.58g化合物C-12，产率76％。m/z＝754.5
化合物C-13的合成：
Figure PCTCN2020105574-appb-000075
将化合物1-1(6.5g，20mmol)、13-1(10.88g，40mmol)、碳酸钾(8.34g，60mmol)、四(三苯基膦)钯(0.69g，0.6mmol)置于有甲苯和甲醇(体积比3：1)的三颈烧瓶中，置换氮气三次，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到中间体13-2共9.44g，产率76％。
将化合物13-2(6.21g，10mmol)溶解在无水甲苯中，加入7-1(2.73g，10mmol)，叔丁醇钠(2.88g，30mmol)及三二亚苄基丙酮二钯(0.28g，0.3mmol)，置换氮气三次后，加入三叔丁基膦(0.3mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得到5.54g化合物C-13，产率68％。m/z＝814.3
化合物C-14的合成：
Figure PCTCN2020105574-appb-000076
将化合物14-1(2.1g，10mmol)、2-溴三亚苯(3.06g，10mmol)，溶解在无水甲苯中，叔丁醇钠(2.88g，30mmol)及三二亚苄基丙酮二钯(92mg，0.1mmol)，置换氮气三次后，加入三叔丁基膦(0.1mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得2.7g化合物14-2，产率62％。
将化合物14-2(2.6g，6mmol)、3-溴-1,10-菲罗啉(1.55g，6mmol)，溶解在无水甲苯中，叔丁醇钠(1.73g，18mmol)及三二亚苄基丙酮二钯(55mg，0.06mmol)，置换氮气三次后，加入三叔丁基膦(0.06mmol)，逐渐升温至110℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱得1.7g化合物C-14，产率46％。m/z＝615.2
化合物C-15的合成：
Figure PCTCN2020105574-appb-000077
将化合物15-1(3.3g，15mmol)、2-溴三亚苯(4.6g，15mmol)，溶解在无水甲苯中，叔丁醇钠(4.32g，45mmol)及三二亚苄基丙酮二钯(0.14g，0.15mmol)，置换氮气三次后，加入三叔丁基膦(0.15mmol)，逐渐升温至80℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱4.74g化合物15-2，产率71％。
将化合物15-2(4.45g，10mmol)、15-3(2.75g，10mmol)，溶解在无水甲苯中，叔丁醇钠(2.88g，30mmol)及三二亚苄基丙酮二钯(92mg，0.1mmol)，置换氮气三次后，加入三叔丁基膦(0.01mmol)，逐渐升温至110℃，搅拌反应。待TLC点板反应物消失，移开热源。待体系冷却后，加入水，分离有机层，并用乙酸乙酯萃取三次，减压下浓缩，过硅胶柱2.43g化合物C-15，产率38％。m/z＝641.2
消光系统及折射率计算
通过真空蒸镀方式将化合物蒸镀于单晶硅上形成50nm的薄膜，单晶硅置于椭偏仪(ES-01)样品台，入射角70°，测试为大气环境，化合物的消光系数(k)与折射率(n)测试结果由椭偏仪拟合得出。
结果如表1所示：
表1
Figure PCTCN2020105574-appb-000078
本申请的化合物在可见光波段吸收弱，在紫外波段有较高的吸收，能够抵抗外部高能量光对器件内部的损害。较高的折射率能保证更好的光提取效果。
OLED器件的制备及表征
下面通过具体实施例来详细说明采用上述的OLED器件的制备过程，如图1所示，OLED器件的结构为：ITO/Ag/ITO(阳极)/HATCN/SFNFB/m-CP:Ir(p-ppy) 3/NaTzF 2/LiF/Mg:Ag/光取出层，制备步骤如下：
清洗ITO导电玻璃阳极层，后用去离子水、丙酮、异丙醇超声清洗15分钟，然后在等离子体清洗器中处理5分钟以提高电极功函。在ITO阳极层上，通过真空蒸镀方式蒸镀空穴注入层材料HATCN，厚度为5nm，蒸镀速率
Figure PCTCN2020105574-appb-000079
在空穴注入层上，通过真空蒸镀方式蒸镀空穴传输材料SFNFB，厚度为80nm。在空穴传输层之上蒸镀发光层，m-CP作为作为主体材料，Ir(p-ppy) 3作为掺杂材料，Ir(p-ppy) 3和m-CP的质量比为1:9，厚度为30nm。在发光层之上，通过真空蒸镀方式蒸镀电子传输材料NaTzF 2，厚度为30nm。在电子传输层之上，真空蒸镀电子注入层LiF，厚度为1nm，该层为电子注入层7。在电子注入层之上，真空蒸镀阴极Mg:Ag层，Mg:Ag掺杂比例为9:1，厚度15nm。在阴极层之上，通过真空蒸镀方式蒸镀光取出层化合物C-2，厚度为60nm。
器件实施例2：有机电致发光器件的光取出层化合物变为C-3。
器件实施例3：有机电致发光器件的光取出层化合物变为C-6。
器件实施例4：有机电致发光器件的光取出层化合物变为C-7。
器件实施例5：有机电致发光器件的光取出层化合物变为C-9。
器件实施例6：有机电致发光器件的光取出层化合物变为C-10。
器件实施例7：有机电致发光器件的光取出层化合物变为C-11。
器件实施例8：有机电致发光器件的光取出层化合物变为C-12。
器件实施例9：有机电致发光器件的光取出层化合物变为C-13。
器件实施例10：有机电致发光器件的光取出层化合物变为C-1。
器件实施例11：有机电致发光器件的光取出层化合物变为C-4。
器件实施例12：有机电致发光器件的光取出层化合物变为C-5。
器件实施例13：有机电致发光器件的光取出层化合物变为C-8。
器件实施例14：有机电致发光器件的光取出层化合物变为C-14。
器件实施例15：有机电致发光器件的光取出层化合物变为C-15。
器件比较例1：有机电致发光器件的光取出层化合物变为CBP。
器件中所涉及的化合物结构如下：
Figure PCTCN2020105574-appb-000080
表2
编号 光取出层化合物 发光效率(cd/A)
器件实施例1 C-2 1.24
器件实施例2 C-3 1.12
器件实施例3 C-6 1.09
器件实施例4 C-7 1.25
器件实施例5 C-9 1.15
器件实施例6 C-10 1.09
器件实施例7 C-11 1.05
器件实施例8 C-12 1.17
器件实施例9 C-13 1.21
器件实施例10 C-1 1.12
器件实施例11 C-4 1.13
器件实施例12 C-5 1.04
器件实施例13 C-8 1.06
器件实施例14 C-14 1.11
器件实施例15 C-15 1.12
比较例1 CBP 1
表2中发光效率是电流密度为10mA/cm 2时所得相对值。从表2可以看出相比对比例，本申请的化合物作为光取出层可以有效的提高有机电致发光器件的发光效率。进一步地，本申请的化合物中C-2、C-7、C-12、C-13作为光取出层的有机电致发光器件的发光效率更佳。
以上所述实施例仅表达了本申请的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对申请专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本申请构思的前提下，还可以做出若干变形和改进，这些都属于本申请的保护范围。因此，本申请专利的保护范围应以所附权利要求为准。

Claims (15)

  1. 一种有机电致发光器件，包含两个电极，设置在所述两个电极之间的一个或多个有机功能层和设置于一电极表面且远离有机功能层一侧的光取出层，其特征在于：所述光取出层材料包含如通式(1)所示的化合物：
    Figure PCTCN2020105574-appb-100001
    其中：
    L 1、L 2和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取代或未取代的环原子数3至30的非芳香环系；
    Ar 1选自吸电子基团；Ar 2选自取代或未取代的环原子数为10-30的稠环芳香基团或稠环杂芳香基团；
    V每次出现分别独立选自CR 1或N；
    R 1每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
  2. 根据权利要求1所述的有机电致发光器件，其特征在于：Ar 2选自(A-1)-(A-5)的任一基团：
    Figure PCTCN2020105574-appb-100002
    其中：
    X每次出现分别独立选自CR 2或N；
    R 2每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
  3. 根据权利要求2所述的有机电致发光器件，其特征在于：通式(1)选自通式(2-1)-(2-4)任一结构：
    Figure PCTCN2020105574-appb-100003
  4. 根据权利要求1所述的有机电致发光器件，其特征在于：Ar 1选自以下基团中的任一种：
    Figure PCTCN2020105574-appb-100004
    其中：
    X 1每次出现分别独立选自CR 3或N，且至少一个X 1选自N；
    Y每次出现分别独立选自NR 4、CR 4R 5、O、S、SiR 4R 5、S＝O、SO 2或PR 4；
    R 3、R 4和R 5每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
  5. 根据权利要求4所述的有机电致发光器件，其特征在于：Ar 1选自以下基团中的任一种：
    Figure PCTCN2020105574-appb-100005
  6. 根据权利要求4所述的有机电致发光器件，其特征在于：通式(1)选自通式(3-1)或(3-2)：
    Figure PCTCN2020105574-appb-100006
    其中：
    X每次出现分别独立选自CR 2或N；
    R 2每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原 子的杂芳氧基基团、或这些基团的组合。
  7. 根据权利要求1所述的有机电致发光器件，其中L 1、L 2和L 3分别独立选自单键或以下基团中的任一种：
    Figure PCTCN2020105574-appb-100007
    其中：
    X 2每次出现分别独立选自CR 6或N；
    Y 1每次出现分别独立选自NR 7、CR 7R 8、O、S、SiR 7R 8、S＝O、SO 2或PR 7；
    R 6、R 7和R 8每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
  8. 根据权利要求7所述的有机电致发光器件，其中L 1、L 2和L 3分别独立选自单键或苯。
  9. 根据权利要求1-8任一项所述的有机电致发光器件，其特征在于：所述光取出层的材料在波长630nm处折射率大于1.7。
  10. 根据权利要求1-8任一项所述的有机电致发光器件，其特征在于：所述光取出层的材料在波长为430nm时的消光系数小于0.1。
  11. 根据权利要求1-8任一项所述的有机电致发光器件，其特征在于：所述有机电致发光器件是有机发光二极管，其中，所述光取出层位于所述有机发光二极管的阴极表面上。
  12. 一种有机化合物，其特征在于：选自如通式(4)所示的结构：
    Figure PCTCN2020105574-appb-100008
    其中：
    L 1和L 3分别独立选自单键，取代或未取代的环原子数5至30的芳香基团或杂芳香基团，或取代或未取代的环原子数3至30的非芳香环系；
    L 2选自单键或者以下基团中的任一种：
    Figure PCTCN2020105574-appb-100009
    W、W 1每次出现分别独立选自CR 9或N；
    Y 2、Y 3每次出现分别独立选自NR 10、CR 10R 11、O、S、SiR 10R 11、S＝O、SO 2或PR 10；
    R 9、R 10和R 11每次出现分别独立选自：氢，D，具有1至20个C原子的直链烷基，具有1至20个C原子的直链烷氧基，具有1至20个C原子的直链硫代烷氧基，具有3至20个C原子的支链或环状的烷基，具有3至20个C原子的支链或环状的烷氧基，具有3至20个C原子的支链或环状的硫代烷氧基、甲硅烷基、具有1至20个C原子的酮基、具有2至20个C原子的烷氧基羰基、具有7至20个C原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯、硫氰酸酯、异硫氰酸酯、羟基、硝基、CF 3、Cl、Br、F、可交联的基团、具有5至60个环原子的取代或未取代的芳香基团、具有5至60个环原子的取代或未取代的杂芳香基团、具有5至60个环原子的芳氧基、具有5至60个环原子的杂芳氧基基团、或这些基团的组合。
  13. 根据权利要求12所述的有机化合物，其特征在于：通式(4)选自通式(5-1)-(5-6)任意一种：
    Figure PCTCN2020105574-appb-100010
  14. 一种组合物，其特征在于，包含有至少一种如权利要求11-13任一项所述的有机化合物，及至少一种有机溶剂。
  15. 一种光取出层材料，其特征在于，包含权利要求11-13中任一项所述的有机化合物。
PCT/CN2020/105574 2019-11-12 2020-07-29 含光取出层材料的有机电致发光器件 WO2021093377A1 (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201911098682.3 2019-11-12
CN201911098682 2019-11-12

Publications (1)

Publication Number Publication Date
WO2021093377A1 true WO2021093377A1 (zh) 2021-05-20

Family

ID=75911946

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2020/105574 WO2021093377A1 (zh) 2019-11-12 2020-07-29 含光取出层材料的有机电致发光器件

Country Status (2)

Country Link
CN (1) CN112864334B (zh)
WO (1) WO2021093377A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113277992A (zh) * 2021-05-25 2021-08-20 上海钥熠电子科技有限公司 链状化合物和包含其的有机电致发光显示器件
WO2022100634A1 (zh) * 2020-11-12 2022-05-19 烟台海森大数据有限公司 一种有机电致发光器件及包含该器件的显示装置

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022264974A1 (ja) * 2021-06-15 2022-12-22 保土谷化学工業株式会社 アザベンゾオキサゾール環構造を有するアミン化合物およびそれを用いた有機エレクトロルミネッセンス素子
CN115710265A (zh) * 2021-08-19 2023-02-24 江苏三月科技股份有限公司 一种芳胺类有机化合物及其应用
CN114105891B (zh) * 2021-12-02 2024-01-26 长春海谱润斯科技股份有限公司 一种芴衍生物及其有机电致发光器件

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101805266A (zh) * 2008-10-13 2010-08-18 葛来西雅帝史派有限公司 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件
WO2014104500A1 (ko) * 2012-12-31 2014-07-03 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
CN104662010A (zh) * 2012-08-30 2015-05-27 出光兴产株式会社 芳香族胺衍生物以及使用其的有机电致发光元件
KR20150059680A (ko) * 2013-11-22 2015-06-02 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20160142918A (ko) * 2015-06-03 2016-12-14 머티어리얼사이언스 주식회사 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자
KR20170093270A (ko) * 2016-02-03 2017-08-16 주식회사 동진쎄미켐 캡핑층을 구비하는 유기발광소자 및 이를 이용한 전자장치
CN107216329A (zh) * 2017-07-13 2017-09-29 长春海谱润斯科技有限公司 一种吡啶并吲哚衍生物及使用该化合物制备的有机电致发光器件
CN108341795A (zh) * 2018-02-09 2018-07-31 长春海谱润斯科技有限公司 一种三芳胺衍生物及其有机电致发光器件
CN108774175A (zh) * 2018-05-29 2018-11-09 长春海谱润斯科技有限公司 一种含芴化合物及其有机发光器件
CN109020903A (zh) * 2018-07-12 2018-12-18 长春海谱润斯科技有限公司 一种三芳胺衍生物及其有机电致发光器件
CN109400488A (zh) * 2018-11-29 2019-03-01 长春海谱润斯科技有限公司 一种芳胺类衍生物及其有机电致发光器件
TW201930551A (zh) * 2017-12-21 2019-08-01 日商保土谷化學工業股份有限公司 有機電致發光元件及其製造方法
CN110128330A (zh) * 2018-02-09 2019-08-16 北京鼎材科技有限公司 芳胺衍生物及其应用和有机电致发光器件
TW201936893A (zh) * 2018-01-10 2019-09-16 日商保土谷化學工業股份有限公司 有機el元件、具有苯并唑環結構之胺化合物、及將其用於有機el元件之覆蓋層之方法

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101805266A (zh) * 2008-10-13 2010-08-18 葛来西雅帝史派有限公司 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件
CN104662010A (zh) * 2012-08-30 2015-05-27 出光兴产株式会社 芳香族胺衍生物以及使用其的有机电致发光元件
WO2014104500A1 (ko) * 2012-12-31 2014-07-03 제일모직 주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150059680A (ko) * 2013-11-22 2015-06-02 (주)피엔에이치테크 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR20160142918A (ko) * 2015-06-03 2016-12-14 머티어리얼사이언스 주식회사 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자
KR20170093270A (ko) * 2016-02-03 2017-08-16 주식회사 동진쎄미켐 캡핑층을 구비하는 유기발광소자 및 이를 이용한 전자장치
CN107216329A (zh) * 2017-07-13 2017-09-29 长春海谱润斯科技有限公司 一种吡啶并吲哚衍生物及使用该化合物制备的有机电致发光器件
TW201930551A (zh) * 2017-12-21 2019-08-01 日商保土谷化學工業股份有限公司 有機電致發光元件及其製造方法
TW201936893A (zh) * 2018-01-10 2019-09-16 日商保土谷化學工業股份有限公司 有機el元件、具有苯并唑環結構之胺化合物、及將其用於有機el元件之覆蓋層之方法
CN108341795A (zh) * 2018-02-09 2018-07-31 长春海谱润斯科技有限公司 一种三芳胺衍生物及其有机电致发光器件
CN110128330A (zh) * 2018-02-09 2019-08-16 北京鼎材科技有限公司 芳胺衍生物及其应用和有机电致发光器件
CN108774175A (zh) * 2018-05-29 2018-11-09 长春海谱润斯科技有限公司 一种含芴化合物及其有机发光器件
CN109020903A (zh) * 2018-07-12 2018-12-18 长春海谱润斯科技有限公司 一种三芳胺衍生物及其有机电致发光器件
CN109400488A (zh) * 2018-11-29 2019-03-01 长春海谱润斯科技有限公司 一种芳胺类衍生物及其有机电致发光器件

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022100634A1 (zh) * 2020-11-12 2022-05-19 烟台海森大数据有限公司 一种有机电致发光器件及包含该器件的显示装置
CN113277992A (zh) * 2021-05-25 2021-08-20 上海钥熠电子科技有限公司 链状化合物和包含其的有机电致发光显示器件

Also Published As

Publication number Publication date
CN112864334A (zh) 2021-05-28
CN112864334B (zh) 2023-03-24

Similar Documents

Publication Publication Date Title
WO2021093377A1 (zh) 含光取出层材料的有机电致发光器件
CN111278838B (zh) 含硼杂环化合物、高聚物、混合物、组合物及其用途
CN109638171B (zh) 有机混合物、高聚物、组合物及其用途
CN110854293B (zh) 氮杂环化合物、组合物、高聚物及有机电致发光器件
TW201038576A (en) Materials for organic electroluminescent devices
US10510967B2 (en) Organic compound, and mixture, formulation and organic device comprising the same
WO2019114668A1 (zh) 一种过渡金属配合物材料及其在电子器件的应用
CN104892578B (zh) 芴螺三苯胺衍生物及其用途
CN111834537B (zh) 一种包含光取出层的有机电致发光器件
CN108349890B (zh) 用于制备有机电子器件的有机功能化合物及其应用
CN109705018B (zh) 有机化合物、有机混合物、组合物及有机电子器件
CN109790183A (zh) 金属有机配合物及其应用、混合物、有机电子器件
CN109790087B (zh) 氘代稠环化合物、高聚物、混合物、组合物以及有机电子器件
CN109659448B (zh) 有机混合物、组合物及有机电子器件
CN112534598B (zh) 包含光取出层的有机电致发光器件、杂原子多芳环化合物及组合物
WO2019120177A1 (zh) 用于制备有机电子器件的组合物、有机电子器件及应用
CN110964009B (zh) 一种含菲啰啉结构的化合物及其应用和一种有机电致发光器件
WO2021143246A1 (zh) 有机电致发光器件和含稠环的芳胺类化合物
CN112864342B (zh) 有机电致发光器件
WO2017118155A1 (zh) 一种有机光电材料及其用途
WO2018108108A1 (zh) 共轭聚合物及其在有机电子器件的应用
CN111725414B (zh) 一种包含光取出层的有机电致发光器件
WO2018108107A1 (zh) 共轭聚合物及其在有机电子器件的应用
WO2018099431A1 (zh) 芘类有机化合物及其制备方法和应用
WO2019114609A1 (zh) 一种金属有机配合物及其在有机电子器件中的应用

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20886911

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20886911

Country of ref document: EP

Kind code of ref document: A1

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 09/11/2022)

122 Ep: pct application non-entry in european phase

Ref document number: 20886911

Country of ref document: EP

Kind code of ref document: A1