TWI461509B - 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 - Google Patents

新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 Download PDF

Info

Publication number
TWI461509B
TWI461509B TW099120052A TW99120052A TWI461509B TW I461509 B TWI461509 B TW I461509B TW 099120052 A TW099120052 A TW 099120052A TW 99120052 A TW99120052 A TW 99120052A TW I461509 B TWI461509 B TW I461509B
Authority
TW
Taiwan
Prior art keywords
substituted
unsubstituted
group
aryl
alkyl
Prior art date
Application number
TW099120052A
Other languages
English (en)
Other versions
TW201114880A (en
Inventor
Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
Original Assignee
Dow Advanced Display Material Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Advanced Display Material Ltd filed Critical Dow Advanced Display Material Ltd
Publication of TW201114880A publication Critical patent/TW201114880A/zh
Application granted granted Critical
Publication of TWI461509B publication Critical patent/TWI461509B/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • 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
    • C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D241/46—Phenazines
    • 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
    • C07D251/16—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 only one ring carbon atom
    • C07D251/20—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 only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such 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
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/20—Acenaphthenes; Hydrogenated acenaphthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/90—Ring systems containing bridged rings containing more than four rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Description

新穎有機電場發光化合物及使用該化合物之有機電場發光裝置
本發明係關於一種新穎有機電場發光化合物及包含該化合物之有機電場發光裝置。根據本發明之有機電場發光化合物係如化學式(1)所示：
在眾多顯示裝置之中，電場發光裝置(electroluminescent,EL)作為自體發光裝置的優點在於它們提供了寬廣的視角、優越的對比與高回應速率。1987年時，Eastman Kodak首先開發出一種有機EL裝置，其係使用低分子量芳香族二胺與鋁錯化物作為形成電場發光層之物質[App1 .Phys .Lett . 51,913,1987]。
在有機EL裝置中，當施加電荷至有機層(形成於電子注入電極(陰極)與電洞注入電極(陽極)之間)時，電子與電洞會配成對，並在電子-電洞對消耗後發射出光。有機EL裝置的優點在於：其可形成於撓性透明基材上(例如塑膠)；相較於電漿顯示器面板或無機EL顯示器，其用相對低的電壓(10或更低)即可操作；消耗較低的功率；以及提供優質的顏色。此外，因能呈現綠、藍及紅色，有機EL裝置受矚目成為下一代、全色彩顯示裝置。
在有機EL裝置中，決定其效能(包括發光效率與操作壽命)的最重要因素為電場發光材料。電場發光材料的一些要件包括於固態之高電場發光量子產率(quantum yield)、高電子及電洞遷移率、真空沉積期間的高分解抗性、形成均勻薄膜的能力以及穩定性。
一般而言，有機EL裝置通常具有陽極/電洞注入層(HIL)/電洞傳輸層(HTL)/發光材料層(EML)/電子傳輸層(ETL)/電子注入層(EIL)/陰極之組構。有機電場發光裝置發射藍、綠或紅光者，其可依據如何形成發光材料層而製造。
在功能性方面，電場發光材料可切分為主體材料與摻雜劑材料。一般而言，已知電場發光層藉由摻雜摻雜劑於主體中而製造者能提供優越的EL特性。近來，開發具高效率與長操作壽命之有機EL正成為迫在眉急的要務。尤其是，考慮到中至大尺寸(OLED)面板需要之EL效能程度，開發明顯優於現存電場發光材料之材料有迫切的需求。
就藍光電場發光材料而言，許多材料已接著Idemitsu Kosan的DPVBi之後商品化了。除了Idemitsu Kosan的藍光材料系統以外，Kodak的二萘基蒽(dinaphthylanthracene)及四(第三丁基)苝(tetra(t-butyl)perylene)已為眾知，但仍需要進一步的研究與開發。迄今為止，已知Idemitsu Kosan的二苯乙烯化合物具有最佳的發光效率。其呈現6流明/瓦(lm/w)的功率以及30,000小時或更長的操作壽命。然而，其天空藍(sky-blue)顏色並不適合於全彩色顯示器。一般而言，如果電場發光波長稍往較長波長偏移，藍光電場發光在發光效率方面就變得有利。但是，如此並不適用於高品質顯示器，因為無法達到純藍的顏色。因此，改善色純度(color purity)、效率以及熱穩定性的研究及開發有著高度的需求。
為了提供具高效率與長壽命的主體材料，已有各種具不同骨幹結構的EL化合物被揭露，包括二螺-茀-蒽(dispiro-fluorene-anthracene)(TBSA)、三-螺茀(ter-spirofluorene)(TSF)、雙聯伸三苯(bitriphenylene)(BTP)等。然而，它們都無法在色純度或發光效率方面提供令人滿意的結果。
TBSA係由Gyeongsang University及Samsung SDI[Kwon,S. K. et al.,Advanced Materials,2001,13,1690；日本專利早期公開案JP 2002121547]所發表者，其於7.7伏特(V)下表現出3燭光/安培(cd/A)之發光效率，以及相對較好的色坐標(color corrdinate)(0.15,0.11)，但是其為單層之材料，且不適合商業用途。
TSF係由國立臺灣大學(Wu,C. C. et al.,Advanced Materials,2004,16,61；美國專利公開案US 2005040392)所發表者，其表現出相對較好的外部量子效率(5.3%)，但對實際應用仍不足。此外，BTP係由國立臺灣清華大學(Cheng,C. -H. et al.,Advanced Materials,2002,14,1409；美國專利公開案第US 2004076852號)所發表者，其表現出2.76 cd/A的發光效率以及相對較好的色坐標(0.16,0.14)，但對實際應用仍然不足。如上所述，現存的單層材料未使用主體-摻雜劑薄膜層，就色純度及效率來說，被認為難以達到商業化。再者，它們缺乏關於操作壽命方面的可靠數據。
根據Mitsui Chemical之專利(美國專利公開案第7,166,240號)，下列所示之化合物具有390至430奈米(nm)之吸收光譜，並表現出4.6 cd/A的發光效率。然而，因具有上述吸收波長，藍綠色(bluish green color)之發光為可預期的。實際上，該專利所陳述的是藍綠色。因所揭露的是對稱結構，所以不可能獲得純藍色。此等材料無法發射純藍顏色，並不適用於全彩色顯示器。
關於綠色螢光材料，參(8-羥基喹啉)鋁(III)(Alq)用來當主體，而將香豆素衍生物(coumarin derivative)(C545T)、喹吖酮衍生物(quinacridone derivative)、DPT等用來當摻雜劑，摻雜濃度為百分之幾至幾十。雖然現存電場發光材料表現出可商業化之初始發光效率，此效率卻隨時間快速衰減。因為壽命問題，它們難以應用於高效能、大尺寸面板。
因此，有必要開發能提供OLED裝置滿意的操作壽命、較佳穩定性以及優質的效能之主體材料。
 技術難題
因此，本發明之一目的在於提供有一種機電場發光化合物，其具有優於現存材料之發光效率及裝置操作壽命，且具備帶有適當的色坐標之較佳骨幹及以解決先前問題。本發明之另一目的在於提供一種有機電場發光裝置，其使用該有機電場發光化合物作為有機電場發光材料。
 技術方案
在一通常態樣中，本發明提供化學式(1)所示之有機電場發光化合物，以及含此化合物之有機電場發光裝置。因具有較佳的發光效率及優良的壽命特性，本發明之有機電場發光化合物可用於製造具有極優操作壽命之OLED裝置。
其中，R1 至R18 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、與一個或多個經取代或未經取代之(C3-C30)環烷基稠合之經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR21 R22 、BR23 R24 、PR25 R26 、P(=O)R27 R28 [其中，R21 至R28 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、Ra Rb Rc Si-[其中，Ra 、Rb 、Rc 獨立地表示經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基]、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、Rd Y-[其中，Y表示S或O，且Rd 表示經取代或未經取代之(C1-C30)烷基或經取代或未經取代之(C6-C30)芳基]、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、Re C(=O)-[其中，Re 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、Rf C(=O)O-[其中，Rf 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、羧基、硝基、或羥基，或者，它們可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環；A、B以及W獨立地表示-(CR51 R52 )m -、-(R51 )C=C(R52 )-、-N(R53 )-、-S-、-O-、-Si(R54 )(R55 )-、-P(R56 )-、-P(=O)(R57 )-、-C(=O)-或-B(R58 )-，其中，R51 至R58 及R61 至R63 與R1 至R18 相同；該雜環烷基及雜芳基可含一個或多個選自B、N、O、S、P(=O)、Si及P之雜原子；以及m表示1或2之整數。
在本發明中，“烷基”、“烷氧基”及其他含“烷基”部份(moiety)之取代基包括直鏈與分支鏈種類兩者，而且“環烷基”包括單環烴以及多環烴(例如經取代或未經取代之金剛烷基或經取代或未經取代之(C7-C30)雙環烷基)。在本發明中，“芳基”表示經由除去一個氫原子而自芳香族烴衍生的有機基，而且可包括含有4至7元，較佳為5或6元單環或稠合環，包括數個藉由單鍵鍵聯之芳基。芳基的具體實例包括苯基、萘基、聯苯基、蒽基、茚基、茀基、菲基、聯伸三苯基(triphenylenyl)、芘基、苝基(perylenyl)、蒯基(chrysenyl)、稠四苯基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等，但不限於此。該萘基包含1-萘基及2-萘基，該蒽基包含1-蒽基、2-蒽基及9-蒽基，且該茀基包含1-茀基、2-茀基、3-茀基、4-茀基及9-茀基。
在本發明中，術語“雜芳基”表示含有1至4個選自B、N、O、S、P(=O)、Si及P之雜原子作為芳香族環狀骨幹原子，及碳原子作為其他剩餘的芳香族環狀骨幹原子之芳基。其可為5或6元單環雜芳基或由與苯環縮合而成的多環雜芳基，而且可為部分飽合。再者，此雜芳基包括多於一個藉由單鍵鍵結的雜芳基。雜芳基可包含二價芳基，其中，環中的雜原子可經氧化或四級化(quaternize)而形成，例如，N-氧化物或四級鹽。雜芳基的具體實例包括單環雜芳基，例如，呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基、唑基、二唑基、三基、四基、***基、四唑基、呋吖基、吡啶基、吡基、嘧啶基、嗒基等；以及多環之雜芳基，例如，苯并呋喃基、苯并噻吩基、異苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異唑基、苯并唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、噌啉基(cinnolinyl)、喹唑啉基(quinazolinyl)、喹啉基、咔唑基、啡啶基、苯并二苊基(benzodioxolyl)等、其N-氧化物(例如，吡啶基N-氧化物，喹啉基N-氧化物)、其四級鹽類等，但不限於此。
在本發明中，“(C1-C30)烷基”包括(C1-C20)烷基或(C1-C10)烷基，且“(C6-C30)芳基”包括(C6-C20)芳基或(C6-C12)芳基。“(C3-C30)雜芳基”包括(C3-C20)雜芳基或(C3-C12)雜芳基，以及“(C3-C30)環烷基”包括(C3-C20)環烷基或(C3-C7)環烷基。“(C2-C30)烯基或炔基”包括(C2-C20)烯基或炔基，或(C2-C10)烯基或炔基。
而且，在本發明中，術語“經取代或未經取代”或“具有或不具有取代基”表示取代基可經一個或多個選自下列所組成群組之取代基取代：氫、氘、鹵素、具有或不具鹵素取代基之(C1-C30)烷基、(C6-C30)芳基、具有或不具(C6-C30)芳基取代基之(C3-C30)雜芳基、5至7元雜環烷基、與一個或多個芳環稠合之5至7元雜環烷基、(C3-C30)環烷基、與一個或多個芳環稠合之(C3-C30)環烷基、三(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR31 R32 、BR33 R34 、PR35 R36 、P(=O)R37 R38 [其中，R31 至R38 獨立地表示(C1-C30)烷基、(C6-C30)芳基或(C3-C30)雜芳基]、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、(C1-C30)烷氧基、(C1-C30)烷基硫基、(C6-C30)芳氧基、(C6-C30)芳硫基、(C1-C30)烷氧基羰基、(C1-C30)烷基羰基、(C6-C30)芳基羰基、(C6-C30)芳氧基羰基、(C1-C30)烷氧基羰氧基、(C1-C30)烷基羰氧基、(C6-C30)芳基羰氧基、(C6-C30)芳氧基羰氧基、羧基、硝基以及羥基；或者，可鍵聯至相鄰取代基以形成環。
R1 至R18 、R21 至R28 、R51 至R58 及R61 至R63 獨立地選自氫、氘、鹵素，烷基(例如甲基、乙基、丙基、丁基、戊基、己基、乙基己基、庚基、辛基等)、芳基(例如苯基、萘基、茀基、聯苯基、菲基、聯三苯基(terphenyl)、芘基、苝基、螺雙茀基(spirobifluorenyl)、丙二烯合茀基、蒯基、聯伸三苯基等)、與一個或多個環烷基稠合之芳基(例如1,2-二氫苊基(1,2-dihydroacenaphthyl)等)、雜芳基(例如二苯并噻吩基(dibenzothiophenyl)、二苯并呋喃基(dibenzofuranyl)、咔唑基(carbazolyl)、吡啶、呋喃、噻吩基(thienyl)、喹啉基(quinolyl)、三基(triazinyl)、嘧啶基(pyrimidinyl)、嗒基(pyridazinyl)、喹啉基(quinoxalinyl)、啡啉基(phenanthrolinyl)等)、與一個或多個芳環稠合之雜環烷基(例如N-苯并吡咯啶基(benzopyrrolidino)、N-苯并哌啶基(benzopiperidino)、N-二苯并嗎啉基(dibenzomorpholino)、N-二苯并氮呯基(dibenzoazepino)等)、經芳基(例如苯基、萘基、茀基、聯苯基、菲基、聯三苯基(terphenyl)、芘基、苝基、螺雙茀基、丙二烯合茀基、蒯基、聯伸三苯基等)取代之胺基、經雜芳基(例如二苯并噻吩基、二苯并呋喃基、咔唑基、吡啶、呋喃、噻吩基、喹啉基、三基、嘧啶基、嗒基、喹啉基、啡啉基等)取代之胺基、芳氧基(例如聯苯基氧基(biphenyloxy)等)、芳硫基(聯苯基硫基(biphenylthio)等)、芳烷基(例如聯苯甲基、三苯基甲基等)、以及，但不限於此。它們可進一步如化學式1所定義般經取代。
根據本發明之有機電場發光化合物可以下列化合物例示之，但不限於此：
根據本發明之有機電場發光化合物可由流程圖1製備，但不限於此。
其中R1 至R18 、A及B與化學式1中的定義相同。
在另一通常態樣中，本發明提供一種有機電場發光裝置，包括：第一電極；第二電極；以及一層或多層有機層，係設於第一電極以及第二電極之間，其中，有機層包括一個或多個化學式(1)所示之有機電場發光化合物。此有機電場發光化合物係用來作為電場發光層中的主體材料。
有機層可包括電場發光層，該場發光層除了包含一個或多個化學式(1)所示的有機電場發光化合物以外，還包含一個或多個摻雜劑。本發明之有機電場發光裝置中使用的摻雜劑並無特別限制。
較佳者，本發明之有機電場發光裝置中使用的摻雜劑可選自化學式(2)至(4)表示之化合物：
其中，Ar11 及Ar12 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基、經取代或未經取代之(C6-C30)芳基胺基、(C1-C30)烷基胺基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基，或與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基，或者，Ar11 及Ar12 藉由具有或不具稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯以形成脂環、或單環或多環之芳環；於c為1時，Ar13 表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基或選自下列結構之取代基：
於c為2時，Ar13 表示經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C4-C30)伸雜芳基或選自下列結構之取代基：
Ar14 及Ar15 獨立地表示經取代或未經取代之(C6-C30)伸芳基或經取代或未經取代之(C4-C30)伸雜芳基；R201 至R203 獨立地表示氫、氘、經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基；d表示從1至4之整數；e表示0或1之整數；以及
其中，R211 至R214 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR301 R302 、BR303 R304 、PR305 R306 、P(=O)R307 R308 [其中，R301 至R308 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C1-C30)烷基硫基、經取代或未經取代之(C6-C30)芳氧基、經取代或未經取代之(C6-C30)芳硫基、經取代或未經取代之(C1-C30)烷氧基羰基、經取代或未經取代之(C1-C30)烷基羰基、經取代或未經取代之(C6-C30)芳基羰基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C6-C30)芳氧基羰基、經取代或未經取代之(C1-C30)烷氧基羰氧基、經取代或未經取代之(C1-C30)烷基羰氧基、經取代或未經取代之(C6-C30)芳基羰氧基、經取代或未經取代之(C6-C30)芳氧基羰氧基、羧基、硝基或羥基，或者，它們各自可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環。
電場發光層為產生電場發光處，而且可由單層或雙層或更多層形成。當使用如本發明之主體-摻雜劑系統時，如本發明之電場發光主體對發光效率提供了顯著的提升。摻雜濃度可為0.5至10 wt%。與其他現存主體材料相比時，如本發明之電場發光主體提供了優異的電洞及電子傳導率，以及極優越的穩定性與顯著提升的發光效率和操作壽命。
化學式(3)或化學式(4)表示之摻雜劑化合物可由第10-2009-0023442號韓國專利申請案中揭露之化合物例示之。更佳者，其可選自下列結構，但不限於此：
除了化學式(1)所示之有機電場發光化合物之外，本發明之有機電場發光裝置可同時更進一步包括一種或多種選自芳基胺化合物以及苯乙烯基芳基胺(styrylarylamine)化合物組成之群組之化合物。芳基胺化合物或苯乙烯基芳基胺化合物可以第10-2008-0123276、10-2008-0107606或10-2008-0118428號韓國專利申請案中揭露者例示之，但不限於此。
再者，在本發明之有機電場發光裝置中，除了化學式(1)所示之有機電場發光化合物之外，有機層可更進一步包括一種或多種選自第1族之有機金屬、第2族、第4週期與第5週期之過渡金屬、鑭系金屬與d-過渡元素(d-transition elements)組成之群組之金屬。
再者，除了該有機電場發光化合物之外，該有機層可包括一層或多層有機電場發光層，該有機電場發光層同時發射藍、綠或紅光，以達成發白光之有機電場發光裝置。該發射藍、綠或紅光之化合物可以第10-2008-0123276、10-2008-0107606或10-2008-0118428號韓國專利申請案中所揭露者例示，但不限於此。
在本發明之有機電場發光裝置中，可將選自硫屬元素化合物層(chalcogenide layer)、金屬鹵化物層以及金屬氧化物層的層體(後文後稱為“表面層”)設置於電極對中的一個或二個電極之內表面。更明確地說，矽或鋁之硫屬元素化合物(包括氧化物)層可設置於電場發光介質層的陽極表面，且金屬鹵化物層或金屬氧化物層可設置於該電場發光介質層的陰極表面。可由此得到操作穩定性。
硫屬元素化合物可為，例如，SiOx (1x2)、AlOx (1x1.5)、SiON、SiAlON等。金屬鹵化物可為，例如，LiF、MgF2 、CaF2 、稀土金屬氟化物等。金屬氧化物可為例如，Cs2 O、Li2 O、MgO、SrO、BaO、CaO等。
在根據本發明之有機電場發光裝置中，較佳者亦可於電極對之至少一表面安置如是所製造之電子傳輸化合物與還原摻雜劑之混合區，或電洞傳輸化合物與氧化摻雜劑之混合區。在此種情形時，由於電子傳輸化合物還原成陰離子，加速電子從混合區注入與傳輸至電場發光介質。此外，由於電洞傳輸化合物氧化成陽離子，加速電洞從混合區注入與傳輸至電場發光介質。較佳的氧化摻雜劑包括各種路易士酸(Lewis acid)及接受體化合物(acceptor compound)。較佳的還原摻雜劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬，及其混合物。
再者，具有二層或更多層之電場發光層之發白光之有機電場發光裝置，可藉由使用還原摻雜層作電荷產生層而製造之。
有利效果
由於根據本發明之有機電場發光化合物具有良好的發光效率與優質的操作壽命，其可使用於製造具非常優異操作壽命之OLED裝置。
發明模式
本發明係藉由參照本發明之有機電場發光化合物、其製備方法，以及使用該化合物之裝置的電場發光特性進一步加以說明。然而，接下來的實施例係提供作為說明之目的，並無限制本發明範圍之意圖。
[製備例1]化合物1的製備
化合物1-1的製備
將2,7-二溴基萘(2,7-dibromonaphthalene)(20公克(g)，128.02毫莫耳(mmol))溶解於DMF(200毫升(mL))中。接著，在室溫下緩慢地加入NBS(50.1 g,281.65 mmol)。室溫下攪拌24小時後，在減壓下蒸餾此有機溶劑。加入蒸餾水後，用EA萃取獲得化合物1-1(36 g，114.64 mmol，89.56%)。
化合物1-2的製備
將化合物1-1(36 g，114.64 mmol)、苯基硼酸(phenylboronic acid)(41.9 g，343.92 mmol)、肆(三苯基膦)鈀(tetrakis(triphenylphosphine)palladium)(Pd(PPh3 )4 ，6.6 g，5.73 mmol)、3 M K2 CO3 (115 mL)、甲苯(500 mL)與乙醇(200 mL)混合，接著在回流下攪拌。經6小時反應接著冷卻至室溫後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-2(29 g，94.02 mmol，82.48%)。
化合物1-3的製備
將KMnO4 (74.2 g，470.13 mmol)與蒸餾水(70 mL)混合，然後將吡啶(400 mL)與化合物1-2(29 g)加入其中。加熱至130 O C後，將KMnO4 (20 g)與蒸餾水(60 mL)間隔30分鐘加入4次。5小時之後，加入400 mL蒸餾水，並在回流下攪拌此混合物12小時。趁熱在減壓下過濾此反應混合物，接著用蒸餾水清洗之。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-3(16 g，43.43 mmol，46.20%)。
化合物1-4的製備
將化合物1-3(16 g，43.43 mmol)溶解於甲醇(300 mL)中，然後在室溫下緩慢地加入SOCl2 。在回流下攪拌12小時後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-4(9 g，22.70 mmol，52.79%)。
化合物1-5的製備
將化合物1-4(9 g，22.70 mmol)溶解於THF(400 mL)中，然後在室溫下緩慢地加入溴化甲鎂(53 mL，158.91 mmol，3.0 M於二***中)。在60 O C下攪拌12小時後，緩慢地加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-5(5.6 g，14.12 mmol，62.21%)。
化合物1-6的製備
將化合物1-5(5.6 g,14.12 mmol)、乙酸(100 mL)及H3 PO4 (200 mL)混合，然後在回流下攪拌。經過10小時，冷卻至室溫後，加入蒸餾水。用NaOH水溶液中和之後，用EA萃取並用MgSO4乾燥後，在減壓下蒸餾，接著以管柱層析法獲得化合物1-6(2.5 g，6.93 mmol，49.11%)。
化合物1-7的製備
將化合物1-6(2.5 g，6.93 mmol)溶解於THF(50 mL)中，然後加入NBS(1.35 g，7.62 mmol)。經過12小時攪拌後，令此有機溶劑在減壓下蒸餾。以管柱分離法獲得化合物1-7(2.7 g，6.14 mmol，88.67%)。
化合物1的製備
將化合物1-7(2.7 g，6.14 mmol)、9-苯基-10-蒽硼酸(2.19 g，7.37 mmol)、肆(三苯基膦)鈀(Pd(PPh3 )4 ，0.35 g，0.30 mmol)、3 M K2 CO3 水溶液(6 mL)、甲苯(40 mL)以及乙醇(15 mL)混合，然後在回流下攪拌。經過8小時反應及冷卻至室溫後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1(2.4 g，3.91 mmol，63.78%)。
化合物1至102係按照製備例1的步驟製備而成。藉此製成的有機電場發光化合物之1 H NMR及MS/FAB數據列示於表1之中。
[實施例1]　使用本發明之有機電場發光化合物之OLED裝置之製造
用根據本發明之有機電場發光化合物製造了OLED裝置。
首先，對獲得自OLED用玻璃(Samsung Corning製造)之透明電極ITO薄膜，依序用三氯乙烯、丙酮、乙醇及蒸餾水施以超音波清洗，並存放於異丙醇中備用。
接著，將ITO基材安置於真空氣相沉積設備的基材夾中，並將4,4’,4"-參(N,N-(2-萘基)-苯基胺基)三苯基胺(2-TNATA)置於真空氣相沉積設備之一小室(cell)中，接著換氣至腔室內真空至10-6 托(torr)。然後，施加電流至小室以蒸發2-TNATA，藉以在ITO基材上形成具有60 nm厚度之電洞注入層。
接著，在真空氣相沉積設備之另一個小室中放入N,N’-雙(α-萘基)-N,N’-二苯基-4,4’-二胺(NPB)，並且施加電流至小室以蒸發NPB，藉以在電洞注入層上形成具有20 nm厚度之電洞傳輸層。
在形成電洞注入層和電洞傳輸層之後，如下所述於其上形成電場發光層。將化合物83置入真空氣相沉積設備作為主體，並將化合物E置入另一個小室作為摻雜劑。將此兩種材料以不同速率蒸發，以使具有30nm厚度之電場發光層(以主體為基礎計摻雜2至5wt%)氣相沉積於電洞傳輸層上。
之後，氣相沉積具有20 nm厚度之參(8-羥基喹啉)鋁(III)(Alq)作為電子傳輸層。接下來，氣相沉積具有1至2 nm厚度之8-羥基喹啉鋰(lithium quinolate，Liq)作為電子注入層。使用另一個真空氣相沉積設備形成具有150 nm厚度之鋁(Al)陰極以製造OLED。
OLED中所使用的各化合物係在10-6 torr下藉由真空昇華純化者。
[實施例2]使用本發明之有機電場發光化合物之OLED裝置之製造
根據實施例1的步驟製造了OLED裝置，不同的是用化合物3及化合物A取代電場發光層中的化合物83及化合物E。
[比較例1]使用現存的電場發光材料之OLED裝置之製造
根據實施例1的步驟製造了OLED裝置，不同的是將二萘基蒽(DNA)放入真空氣相沉積設備中作為主體材料取代本發明之化合物。
[比較例2]使用現存的電場發光材料之OLED裝置之製造。
根據實施例2的步驟製造了OLED裝置，不同的是將DNA放入真空氣相沉積設備中作為主體材料取代本發明之化合物。
於1,000燭光/平方米(cd/m2 )測量實施例1與2以及比較例1與2中製造之OLED裝置的功率效率。其結果列於表2之中。
從表2可見，當使用於綠色或藍色發射電場發光裝置中時，相較於比較例1與2，本發明之有機電場發光化合物提供經改善功率效率，同時也維持了可相比擬或較佳的色純度。

Claims (8)

  1. 一種有機電場發光化合物，係由化學式(1)所示： 其中，R1 至R18 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、與一個或多個經取代或未經取代之(C3-C30)環烷基稠合之經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR21 R22 、BR23 R24 、PR25 R26 、P(=O)R27 R28 [其中，R21 至R28 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、Ra Rb Rc Si-[其中，Ra 、Rb 、Rc 獨立地表示經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基]、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、Rd Y-[其中，Y表示S或O，且Rd 表示經取代或未經取代之(C1-C30)烷基或經取代或未經取代之(C6-C30)芳基]、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、Re C(=O)-[其中，Re 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、Rf C(=O)O-[其中，Rf 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、羧基、硝基、 或羥基，或者，它們可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環；A、B以及W獨立地表示-(CR51 R52 )m -、-(R51 )C=C(R52 )-、-N(R53 )-、-S-、-O-、-Si(R54 )(R55 )-、-P(R56 )-、-P(=O)(R57 )-、-C(=O)-或-B(R58 )-，其中，R51 至R58 及R61 至R63 相同於R1 至R18 ；該雜環烷基及雜芳基可含一個或多個選自B、N、O、S、P(=O)、Si及P之雜原子；以及m表示1或2之整數。
  2. 如申請專利範圍第1項所述之有機電場發光化合物，其中，R1 至R18 、R21 至R28 、R51 至R58 及R61 至R63 定義中的“經取代或未經取代”之取代基係獨立地更進一步經一個或多個選自氫、氘、鹵素、具有或不具鹵素取代基之(C1-C30)烷基、(C6-C30)芳基、具有或不具(C6-C30)芳基取代基之(C3-C30)雜芳基、5至7元雜環烷基、與一個或多個芳環稠合之5至7元雜環烷基、(C3-C30)環烷基、與一個或多個芳環稠合之(C3-C30)環烷基、三(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR31 R32 、BR33 R34 、PR35 R36 、P(=O)R37 R38 [其中，R31 至R38 獨立地表示(C1-C30)烷基、(C6-C30)芳基或(C3-C30)雜芳基]、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、(C1-C30)烷氧基、(C1-C30)烷基硫基、(C6-C30)芳氧基、(C6-C30)芳硫基、(C1-C30)烷氧基羰基、(C1-C30)烷基羰基、(C6-C30)芳基羰基、(C6-C30)芳氧基羰基、(C1-C30)烷氧基羰氧基、(C1-C30)烷基羰氧基、(C6-C30)芳基羰氧基、(C6-C30)芳氧基羰氧基、羧基、硝基以及羥基組成之群組之取代基取代；或者，其係鍵聯至相鄰取代基以形成環。
  3. 一種有機電場發光裝置，包含如申請專利範圍第1或2項所述之有機電場發光化合物。
  4. 如申請專利範圍第3項所述之有機電場發光裝置，其包含第一電極；第二電極；以及一層或多層有機層，該有機層係設於該第一電極以及該第二電極之間，其中，該有機層包含一個或多個如申請專利範圍第1或2項所述之有機電場發光化合物及一個或多個由化學式(2)至(4)所示之摻雜劑： 其中，Ar11 及Ar12 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基、經取代或未經取代之(C6-C30)芳基胺基、(C1-C30)烷基胺基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基，或與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基，或者，Ar11 及Ar12 藉由具有或不具稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯以形成脂環、或單環或多環之芳環；於c為1時，Ar13 表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基或選自下列結構之取代基： 於c為2時，Ar13 表示經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C4-C30)伸雜芳基或選自下列結構之取代基： Ar14 及Ar15 獨立地表示經取代或未經取代之(C6-C30)伸芳基或經取代或未經取代之(C4-C30)伸雜芳基；R201 至R203 獨立地表示氫、氘、經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基；d表示從1至4之整數；e表示0或1之整數；以及 其中，R211 至R214 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7-元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR301 R302 、BR303 R304 、PR305 R306 、P(=O)R307 R308 [其中，R301 至R308 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C1-C30)烷基硫基、經取代或未經取代之(C6-C30)芳氧基、經取代或未經取代之(C6-C30)芳硫基、經取代或未經取代之(C1-C30)烷氧基羰基、經取代或未經取代之(C1-C30)烷基羰基、經取代或未經取代之(C6-C30)芳基羰基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C6-C30)芳氧基羰基、經取代或未經取代之(C1-C30)烷氧基羰氧基、經取代或未經取代之(C1-C30)烷基羰氧基、經取代或未經取代之(C6-C30)芳基羰氧基、經取代或未經取代之(C6-C30)芳氧基羰氧基、羧基、硝基或羥基；或者，它們各自可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環。
  5. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層包含一種或多種選自芳基胺化合物以及苯乙烯基芳基胺化合物組成之群組之化合物。
  6. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層更進一步包括一種或多種選自第1族之有機金屬、第2族、第4週期與第5週期之過渡金屬、鑭系金屬與d-過渡元素組成之群組之金屬或錯化物。
  7. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層包含電場發光層以及電荷產生層。
  8. 如申請專利範圍第4項所述之有機電場發光裝置，其發白光有機電場發光裝置，其中，該有機層包含一層或多層同時發射紅、綠或藍光之有機電場發光層。
TW099120052A 2009-06-22 2010-06-21 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 TWI461509B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020090055500A KR20100137198A (ko) 2009-06-22 2009-06-22 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

Publications (2)

Publication Number Publication Date
TW201114880A TW201114880A (en) 2011-05-01
TWI461509B true TWI461509B (zh) 2014-11-21

Family

ID=43386717

Family Applications (1)

Application Number Title Priority Date Filing Date
TW099120052A TWI461509B (zh) 2009-06-22 2010-06-21 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置

Country Status (3)

Country Link
KR (1) KR20100137198A (zh)
TW (1) TWI461509B (zh)
WO (1) WO2010151006A1 (zh)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9748492B2 (en) 2012-11-02 2017-08-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
KR102263057B1 (ko) 2014-05-07 2021-06-09 삼성전자주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
KR102508566B1 (ko) * 2014-07-10 2023-03-13 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
US10553800B2 (en) 2016-01-05 2020-02-04 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
CN110785867B (zh) 2017-04-26 2023-05-02 Oti照明公司 用于图案化表面上覆层的方法和包括图案化覆层的装置
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
CA3090816A1 (en) * 2018-03-05 2019-09-12 Board Of Regents Of The Nevada System Of Higher Education, On Behalf Of The University Of Nevada, Reno Polycyclic aromatic compounds and methods for making and using the same
KR102247292B1 (ko) * 2018-04-06 2021-04-30 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기발광소자
EP3873887A1 (en) * 2018-10-31 2021-09-08 Merck Patent GmbH Materials for organic electroluminescent devices
EP3880682B1 (de) * 2018-11-15 2023-06-14 Merck Patent GmbH Materialien für organische elektrolumineszenzvorrichtungen
JP7390739B2 (ja) 2019-03-07 2023-12-04 オーティーアイ ルミオニクス インコーポレーテッド 核生成抑制コーティングを形成するための材料およびそれを組み込んだデバイス
KR20210154262A (ko) * 2019-05-10 2021-12-20 듀폰 일렉트로닉스, 인크. 전기활성 화합물
EP4048675A1 (de) 2019-10-25 2022-08-31 Merck Patent GmbH In einer organischen elektronischen vorrichtung einsetzbare verbindungen
EP4110884A1 (de) 2020-02-25 2023-01-04 Merck Patent GmbH Verwendung von heterocyclischen verbindungen in einer organischen elektronischen vorrichtung
EP4115457A1 (de) 2020-03-02 2023-01-11 Merck Patent GmbH Verwendung von sulfonverbindungen in einer organischen elektronischen vorrichtung
CN111763223B (zh) * 2020-06-30 2023-04-28 武汉天马微电子有限公司 一种有机化合物、热活化延迟荧光材料及其应用
CN114478562A (zh) * 2020-10-23 2022-05-13 上海和辉光电股份有限公司 一种化合物及其应用
US11985841B2 (en) 2020-12-07 2024-05-14 Oti Lumionics Inc. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating
EP4320648A1 (en) 2021-04-09 2024-02-14 Merck Patent GmbH Materials for organic electroluminescent devices
TW202309243A (zh) 2021-04-09 2023-03-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
CN114085121A (zh) * 2021-10-29 2022-02-25 天津大学 一种含双芴的类螺烯化合物及其合成方法
WO2023110742A1 (de) 2021-12-13 2023-06-22 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
WO2023152063A1 (de) 2022-02-09 2023-08-17 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1756825A (zh) * 2002-12-31 2006-04-05 伊斯曼柯达公司 配位含芴化合物和电致发光装置
TWI290546B (en) * 2000-08-10 2007-12-01 Mitsui Chemicals Inc Hydrocarbon compounds for organic electroluminescent elements and organic electroluminescent elements
TW200808683A (en) * 2006-07-11 2008-02-16 Merck Patent Gmbh Novel materials for organic electroluminescent devices

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100377575B1 (ko) * 2000-10-17 2003-03-26 삼성에스디아이 주식회사 유기 전계 발광 소자용 청색 발광 화합물 및 이를 사용한유기 전계 발광 소자
TWI314947B (en) * 2002-04-24 2009-09-21 Eastman Kodak Compan Organic light emitting diode devices with improved operational stability

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI290546B (en) * 2000-08-10 2007-12-01 Mitsui Chemicals Inc Hydrocarbon compounds for organic electroluminescent elements and organic electroluminescent elements
CN1756825A (zh) * 2002-12-31 2006-04-05 伊斯曼柯达公司 配位含芴化合物和电致发光装置
TW200808683A (en) * 2006-07-11 2008-02-16 Merck Patent Gmbh Novel materials for organic electroluminescent devices

Also Published As

Publication number Publication date
KR20100137198A (ko) 2010-12-30
WO2010151006A1 (en) 2010-12-29
TW201114880A (en) 2011-05-01

Similar Documents

Publication Publication Date Title
TWI461509B (zh) 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置
KR101427605B1 (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자
TWI461507B (zh) 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置
TWI527875B (zh) 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置
JP5782503B2 (ja) 新規有機電界発光化合物およびこれを使用する有機電界発光素子
JP5781499B2 (ja) 新規有機電界発光化合物およびこれを使用する有機電界発光素子
KR20100109050A (ko) 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자
KR101423070B1 (ko) 유기 전계 발광 소자
TW201509872A (zh) 用於有機電子材料之新穎化合物及使用該化合物之有機電子裝置
JP2013526014A (ja) 新規有機電界発光化合物およびこれを使用する有機電界発光素子
TW201300499A (zh) 新穎有機電場發光化合物及包含該化合物之有機電場發光裝置
KR101645949B1 (ko) 유기발광화합물을 발광재료로서 채용하고 있는 유기 전계 발광 소자
TW201105773A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100118700A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20100106014A (ko) 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계발광 소자
JP2013546171A (ja) 有機電子材料のための新規化合物、およびこれを使用する有機電界発光素子
KR20110116635A (ko) 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20120020816A (ko) 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20100137188A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20120020901A (ko) 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20110008892A (ko) 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20120033017A (ko) 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20100108909A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자
JP2011093825A (ja) ２，２−ジフェニルアダマンチル構造を有する化合物および有機エレクトロルミネッセンス素子
KR20150141179A (ko) 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees