WO2006057325A1 - ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 - Google Patents
ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 Download PDFInfo
- Publication number
- WO2006057325A1 WO2006057325A1 PCT/JP2005/021647 JP2005021647W WO2006057325A1 WO 2006057325 A1 WO2006057325 A1 WO 2006057325A1 JP 2005021647 W JP2005021647 W JP 2005021647W WO 2006057325 A1 WO2006057325 A1 WO 2006057325A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituent
- light
- light emitting
- layer
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- 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
- 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
- C07D209/56—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
- 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
-
- 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
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- 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
- C07C2603/22—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
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Definitions
- the present invention relates to an asymmetric pyrene compound that can be used for both a light emitting transistor element and an organic electoluminescence element, and a light emitting transistor element and an organic electoluminescence element using the same.
- Organic electoluminescence devices (hereinafter abbreviated as “organic EL devices”), which are typical examples of organic semiconductor devices, emit light due to recombination of electrons and holes in a layer made of an organic phosphor. It is a light emitting element using Specifically, an organic EL device comprising a light emitting layer made of the organic compound, an electron injection electrode for injecting electrons into the light emitting layer, and a hole injection electrode for injecting holes into the light emitting layer is disclosed in Patent Document 1. And Patent Document 2 and the like.
- organic phosphors used in the light-emitting layer include berinone derivatives, distritylbenzene derivatives, etc. (Patent Document 1), 1, 3, 6, 8-tetraisobutylene, etc. (Patent Document 2). can give.
- Patent Document 1 Japanese Patent Laid-Open No. 5-315078
- Patent Document 2 JP 2001-118682 A
- a light emitting transistor element is also known in addition to the organic EL element.
- an organic phosphor can be used for both an organic EL device and a light-emitting transistor device, it leads to the efficiency of manufacturing these devices.
- organic phosphors that can be used for both of these devices are known. Accordingly, an object of the present invention is to provide an organic phosphor that can be used for both a light-emitting transistor element and an organic EL element.
- the present invention solves the above problems by using an asymmetric pyrene compound having the following structural formula (1).
- R may have a heteroaryl group which may have a substituent, or may have a substituent.
- An aryl group an alkyl group having 1 to 20 carbon atoms in the main chain which may have a substituent, a cycloalkyl group which may have a substituent, an alkyl group which may have a substituent, a substituent
- An alkyl group which may have a group, a cyano group, a carboxylic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent,
- R may have a hydrogen atom, a heteroaryl group which may have a substituent, or a substituent.
- a good aryl group an alkyl group having 1 to 20 carbon atoms in the main chain which may have a substituent, a cycloalkyl group which may have a substituent, an alkyl group which may have a substituent, An optionally substituted alkyl group, a cyano group, an optionally substituted carboxylic group, an optionally substituted alkoxy group, an optionally substituted aryloxy group And a group selected from a silyl group that may have a substituent, an arylboryl group that may have a substituent, an ester group that may have a substituent, and a halogen atom, and R and Different.
- an asymmetric compound is used as the pyrene compound, an organic EL device is used. And it becomes possible to use as an organic fluorescent substance used for a light emitting transistor element. This is because an asymmetric pyrene compound has moderate crystallinity (non-crystallinity), so that it can have appropriate emission brightness as an organic EL device and appropriate carrier mobility as a light-emitting transistor. It is thought that it became.
- FIG. 1 (a) Chemical formula showing an example of an asymmetric pyrene compound
- FIG. 5 is a cross-sectional view showing an example of a light-emitting transistor element according to the present invention.
- FIG. 6 is a plan view showing a configuration of a source electrode and a drain electrode
- FIG. 7 (a) (b) (c) Schematic diagram showing the light emission mechanism of the light-emitting transistor element.
- FIG. 8 is an electric circuit diagram showing an example of a display device using the light emitting transistor element according to the present invention.
- FIG. 9 is a cross-sectional view showing an example of an organic EL element that is useful in the present invention.
- FIG. 10 is an electrical circuit diagram showing an example of a display device using the organic EL element according to the present invention.
- LSI, LS2, LSI ', LS2' scan line LD1, LD2, LD1 ', LD2' data lines
- This invention is an invention that works on asymmetric pyrene compounds.
- This asymmetric pyrene compound can be used for a light-emitting transistor device or an organic electoluminescence device (organic EL device).
- the asymmetric pyrene compound includes a compound represented by the following chemical formula (1).
- R may have a heteroaryl group which may have a substituent, or may have a substituent.
- An aryl group an alkyl group having 1 to 20 carbon atoms in the main chain which may have a substituent, a cycloalkyl group which may have a substituent, an alkyl group which may have a substituent, a substituent
- An alkyl group which may have a group, a cyano group, a carboxylic group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent,
- R may have a hydrogen atom or a substituent !, a heteroaryl group or a substituent.
- a good aryl group an alkyl group having 1 to 20 carbon atoms in the main chain which may have a substituent, a cycloalkyl group which may have a substituent, an alkyl group which may have a substituent, An optionally substituted alkyl group, a cyano group, an optionally substituted carboxylic group, an optionally substituted alkoxy group, an optionally substituted aryloxy group And a group selected from a silyl group that may have a substituent, an arylboryl group that may have a substituent, an ester group that may have a substituent, and a halogen atom, and R and Different.
- R it may have a predetermined substituent and may be a heteroaryl group (multiple Ring aromatics), alkylphenyl groups substituted with certain alkyl groups, phenyl groups substituted with halogen atoms, naphthyl groups (preferably 2-naphthyl groups), anthryl groups (preferably 2- Anthryl group), a phenanthryl group, an aryl group (including polycyclic aromatics) which may have a predetermined substituent, and a substituent having 1 to 20 carbon atoms in the main chain.
- a heteroaryl group multiple Ring aromatics
- alkylphenyl groups substituted with certain alkyl groups preferably 2-naphthyl groups
- anthryl groups preferably 2- Anthryl group
- a phenanthryl group preferably 2- Anthryl group
- an aryl group including polycyclic aromatics
- the above-mentioned predetermined substituent may be included.
- the substituent used in the heteroaryl group includes a benzofuryl group, a pyrrolyl group, a benzoxazolyl group, a pyrajur group, a chael group, and an alkyl substitution. Examples thereof include a chael group, a bichel group, a ferrule group, a benzochel group, a pyridyl group, a bibilidyl group, a ferruleidyl group, a quinolyl group, and a benzothiazolyl group.
- Examples of the alkyl group used in the alkylfuran group substituted with the predetermined alkyl group include a phenyl group, a methyl group, and an ethyl group.
- Specific examples of the alkylphenol group substituted with this alkyl group include tolyl group, 3-alkylphenol group, 4-alkylphenol group, 3-trifluoromethylphenol group, 4-trifluoroalkyl group. Examples thereof include a methyl phenol group and a 3,5-bis (trifluoromethyl) phenol group.
- halogen atom used in the phenol group substituted with the halogen atom examples include a fluorine atom, a bromine atom, and a chlorine atom, and a fluorine atom is preferable.
- phenyl group substituted with this halogen atom examples include 3-fluorophenol group, 4-fluorophenol group, 3,4-difluorophenyl group, 3,5-difluorophenyl- Group, 3,4,5-trifluorophenol group and the like.
- the substituent used in the aryl group having the above-mentioned predetermined substituent may be a biphenyl group, a terphenyl group, a fuertephenol group, a pyridinophenol group, or the like. Can be given.
- linear or branched alkyl group which may have a substituent having 1 to 20 carbon atoms in the main chain include a methyl group, an ethyl group, an n-propyl group, 2 -Propyl group, n-butyl group, isobutyl group, tert-butyl group, hexyl group, octyl group, dodecyl group, octadecyl group and the like.
- the substituent used in the alkenyl group may have the above-mentioned predetermined substituent.
- the substituent used in the alkyl group may have the above-mentioned predetermined substituent.
- An ether group a phenyl-substituted ether group, a trimethylsilyl-substituted ether group, a propargyl group, and the like.
- the substituent used for the alkoxy group may have the above-mentioned predetermined substituent.
- Examples of the substituent used in the aryloxy group having the above-mentioned predetermined substituent include a phenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and the like.
- halogen atom used in the above-described group having a halogen atom examples include a fluorine atom, a bromine atom, a chlorine atom, and the like. Among these, a group in which only these halogen atoms can be used, among which a fluorine atom is preferable.
- R a phenyl group, a naphthyl group, which may have a substituent
- a benzofuryl group, a phenylpyridyl group, a chael group, a benzocher group, a pyridyl group, a methyl group, a vinyl group and a ethynyl group are preferred.
- R include a hydrogen atom and those exemplified as R.
- R and R are different groups.
- R a hydrogen atom, which may have a substituent, a phenyl group, a naphthyl
- a group selected from a group, a benzofuryl group, a phenylpyridyl group, a chael group, a benzocher group, a pyridyl group, a methyl group, a vinyl group and an ethynyl group is preferred.
- a hydrogen atom a methyl group, a hexyl group, a fullyl group, a biphenyl group, a pyridyl group, a bibilidyl group, a naphthyl group, a biphenyl group, a phenylpyridyl group, an octyl group, a dodecyl group
- a group selected from an octadecyl group, a phenyl-substituted butyl group, or a phenyl-substituted ether group is particularly preferred.
- the molecular weight of the asymmetric pyrene compound of the present invention is preferably 500 or more, more preferably 800 or more, and preferably 5000 or less, more preferably 3000 or less.
- R is a hydrogen atom
- R is a benzothiophene ring (benzocenyl group)
- R is other than a hydrogen atom
- R is a pyridine ring (pyridyl group)
- R is a pyridine ring (pyridyl group)
- R is a biphenyl group and R is an octyl group.
- R is a biphenyl group and R force ⁇ decyl group
- R is a naphthyl group, R force ⁇ decyl group
- R is a phenyl group and R is a phenyl-substituted bur group.
- 1 2 is a pyrene compound in which a pyridine ring (pyridyl group) ((4-11) in Fig. 2 (b)), R is biphenyl
- R is a biphenyl group and R is a pyridine ring (pyridyl group).
- R is pyridine ring (pyridyl group), R is phenyl
- R is a biphenyl group
- R is bibilidyl
- Lysyl group and pyrene compounds ((4-18) in FIG. 2 (c)).
- a part of R may have a substituent.
- R is the same as in the above formula (1).
- Y represents a divalent linking group. .
- Y specifically, a divalent group of the groups exemplified as R above may be used.
- a group that cannot be a divalent group such as a hydrogen atom or a halogen atom is excluded.
- a group selected from an aromatic heterocycle, an aromatic hydrocarbon ring, an alkane, an alkene, and an alkyne is preferably selected.
- This divalent group may have a substituent.
- the aromatic heterocycle and the aromatic hydrocarbon ring mean a ring containing a polycyclic aromatic.
- ⁇ examples include divalent groups derived from a benzene ring (including a phenylene group, a biphenylene group, a terferene group, etc.), a divalent group derived from a naphthalene ring, an anthracene.
- these rings may be a group in which two or more are linked (for example, biphenylene group and the like).
- Examples of such asymmetric pyrene compounds represented by the formula (2) include R as a phenyl group
- Y is a divalent pyrazine ring (Fig. 3 (a) (5-2))
- R is phenyl
- Pyrene compounds (Fig. 3 (a) (5-4)
- Y is a divalent phenol group substituted with two dodecyl ether groups
- R is a tolyl group
- Y is a divalent acetylene group
- a pyrene-based compound ((5-7) in Fig. 3 (b)), an R-catalyst group, where Y is a divalent bifuryl group
- a pyrene compound ((5-8) in Fig. 3 (b)), R is a pyridine ring (pyridyl group), and Y is two
- a pyrene compound ((5-9) in Fig. 3 (c)) which is a valent substituted biphenyl group, and R is a phenyl group
- Y is a divalent biphenyl group (Fig. 3 (c) (5-10)), R is phenyl
- FIGs. 4 (a) and 4 (b) 6-1) to (6-11).
- the above asymmetric pyrene compound can be produced by the method of the following reaction formula ⁇ 1>.
- X represents a halogen atom from which chlorine atom, bromine atom and iodine nuclear atom are also selected.
- the asymmetric pyrene compound is used as a constituent component of a light emitting layer of a light emitting transistor element, a light emitting layer of an organic EL element, a hole transport layer, an electron transport layer, or the like. More specifically, the asymmetric pyrene-based compound is used as a main component of the light emitting layer of the light emitting transistor element and the light emitting layer of the organic EL element, and is also used for the hole transport layer and the electron transport layer of the organic EL element. Used as main constituent or dopant material.
- the light emitting layer refers to a layer that emits light by recombination of holes and electrons. The hole transport layer and the electron transport layer will be described later.
- the main constituent component refers to a component that can mainly exert effects such as light emission luminance, light emission efficiency, carrier mobility, and specific light color.
- the dopant material is a kind of sub-component added to the main component, and refers to a compound added to improve the performance of the main component.
- the asymmetric pyrene compound is used as a main constituent. In this case, in order to further improve the above-described effects, subcomponents such as other organic phosphors and dopant materials may be used in combination as necessary.
- organic phosphors include, but are not limited to, for example, condensed ring derivatives such as anthracene, phenanthrene, pyrene, perylene, and taricene, and quinolinol such as tris (8-quinolinolato) aluminum.
- condensed ring derivatives such as anthracene, phenanthrene, pyrene, perylene, and taricene
- quinolinol such as tris (8-quinolinolato) aluminum.
- Derivative metal complexes benzoxazole derivatives, stilbene derivatives, benzthiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentagen derivatives, oxadiazole derivatives, bisstyrylanthracene derivatives, distyrylbenzene derivatives, etc.
- Bisstyryl derivatives metal complexes combining quinolinol derivatives with different ligands, oxadiazole derivative metal complexes, benzazole derivative metal complexes, coumarin derivatives, pyroguchi pyridine derivatives, perinone derivatives, Zia Zoro pyridine derivatives, and the like.
- examples of other organic phosphors of the polymer type include polyphenylene biylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives.
- the dopant material is not particularly limited.
- phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene, and other condensed ring derivatives benzoxazole derivatives, benz Thiazole derivatives, benzimidazole derivatives, benztriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazol derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopenta Bisstyryl derivatives such as diene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives, diazaindene derivatives, furan derivatives, Derivatives such as vinyl derivatives
- Dibenzofuran derivatives 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzthiazolylcoumarin derivatives, 3-bases N-imidazolyl coumarin derivatives, coumarin derivatives such as 3-benzoxazolyl coumarin derivatives, Lan derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, atalidine derivatives, bis (styryl) benzene Derivatives, oxazine derivatives, phenylene oxide derivatives, quinatalidone derivatives, quinazoline derivatives, pyroguchi pyridine derivatives
- an element having a basic structure of a field effect transistor (FET) as shown in FIG. 5 can be cited.
- the light-emitting transistor element 10 is capable of transporting holes and electrons as carriers, and emits light by recombination of holes and electrons.
- the light-emitting layer 1 includes the above pyrene-based compound as a main constituent, Opposite to the hole injection electrode for injecting holes into the light emitting layer 1, so-called source electrode 2, the electron injection electrode for injecting electrons into the light emitting layer, so-called drain electrode 3, and the source electrode 2 and drain electrode 3.
- a gate electrode 4 force composed of an N + silicon substrate that controls the distribution of carriers in the light emitting layer 1 is also configured.
- the gate electrode 4 may be composed of a conductive layer made of an impurity diffusion layer formed in the surface layer portion of the silicon substrate.
- an insulating film 5 made of silicon oxide and the like is provided on the gate electrode 4, and the source electrode 2 and the drain electrode 3 are spaced apart from each other. Provided.
- the light emitting layer 1 is provided so as to cover the source electrode 2 and the drain electrode 3 and to enter between the two electrodes.
- the carrier mobility or the light emission efficiency preferably satisfies a predetermined range.
- the pyrene compounds having the respective characteristics described above it is possible to enhance the respective functions by adding sub-components such as the dopant.
- the smaller the difference between the HOMO energy level and the LUMO energy level the easier the electrons move, and the light emission and semiconductivity (that is, the conductivity of electrons or holes in one direction).
- Is likely to occur which is preferable. Specifically, 5 eV or less is preferred and 3 eV or less is more preferred. 2.7 eV or less is more preferred. Since this difference is preferably as small as possible, the lower limit of this difference is OeV.
- the upper limit of the carrier mobility is not particularly limited, and it is sufficient if it is about lcm 2 ZV ′ s.
- PL luminous efficiency the ratio of light generated by inserting photons and electrons
- EL quantum efficiency the ratio of emitted light energy to injected optical energy.
- the ratio of the number of emitted photons to the number of injected electrons is the EL emission efficiency (or EL quantum efficiency).
- the injected and excited electrons emit light by recombining with holes. This recombination does not necessarily occur with a probability of 100%. For this reason, when comparing the organic compounds constituting the light emitting layer 1, by comparing the EL luminous efficiency, the ratio of the amount of emitted light energy to the injected light energy, and the recombination of electrons and holes. The synergistic effect of the percentage of binding can be compared. By comparing the PL luminous efficiency, the ratio of the amount of emitted light energy to the injected light energy can be compared. Therefore, by comparing both the PL luminous efficiency and the EL luminous efficiency, It is also possible to compare the rate of recombination of slag and holes.
- the PL luminous efficiency is preferably 20% or more, more preferably 30% or more, as the degree of light emission is large.
- the upper limit of PL luminous efficiency is 100%.
- the EL luminous efficiency as the degree of luminescence is greater preferred instrument 1 X 10- 3% or more is rather good, 5 X 10- 3% or more. Note that the upper limit of EL luminous efficiency is 100%.
- the wavelength of emitted light can be mentioned. This wavelength is within the range of visible light, but has a different wavelength depending on the type of organic phosphor used, particularly the above-mentioned pyrene compound. And organic fireflies with different wavelengths Various colors can be developed by combining light bodies. For this reason, the wavelength of emitted light exhibits its characteristics.
- the light emitting transistor element 10 Since the light emitting transistor element 10 is characterized by light emission, it should have a certain level of light emission brightness.
- This light emission luminance is the amount of light emission corresponding to the brightness of an object that humans feel when looking at the object.
- This emission brightness is preferably as high as possible in the measurement method using a photo counter.
- L X 10 4 CPS (count per sec) or higher is preferred 1 X 10 5 CPS or higher is preferred 1 X 10 6 CPS or higher is more preferred preferable.
- the light-emitting layer 1 is formed by vapor-depositing the constituent organic phosphor or the like (co-evaporation when there are a plurality of types).
- the thickness of the light emitting layer may be at least about 70 nm.
- the source electrode 2 and the drain electrode 3 are electrodes for injecting holes and electrons into the light emitting layer 1, and are formed of gold (Au), magnesium gold alloy (MgAu), or the like.
- the two are formed so as to face each other with a minute gap of 0.4 to 50 m or the like. Specifically, for example, as shown in FIG.
- the source electrode 2 and the drain electrode 3 are formed so as to have comb-shaped portions 2a and 3a each composed of a plurality of comb teeth, and the source electrode 2
- the comb-teeth forming the comb-shaped portion 2a and the comb-teeth forming the comb-tooth-shaped portion 3a of the drain electrode 3 are alternately arranged at predetermined intervals, thereby functioning as the light-emitting transistor element 10. It can be demonstrated more efficiently.
- the interval between the source electrode 2 and the drain electrode 3, that is, the interval between the comb-shaped portion 2a and the comb-shaped portion 3a is preferably 50 / zm or less, more preferably less than or less. . If it exceeds 50 m, sufficient semiconductor properties cannot be exhibited.
- the light-emitting transistor element 10 applies a voltage to the source electrode 2 and the drain electrode 3 to move both holes and electrons therein, and recombines both in the light-emitting layer 1. As a result, light emission can be generated. At this time, the amount of holes and electrons moving between the two electrodes through the light emitting layer 1 depends on the voltage applied to the gate electrode 4. Therefore, it is possible to control the conduction state between the source electrode 2 and the drain electrode 3 by controlling the voltage applied to the gate electrode 4 and its change. Since the light emitting transistor element 10 performs P-type driving, a negative voltage is applied to the drain electrode 3 with respect to the source electrode 2, and a negative voltage is applied to the gate electrode 4 with respect to the source electrode 2. It is done.
- the gate electrode 4 by applying a negative voltage to the gate electrode 4 with respect to the source electrode 2, holes in the light emitting layer 1 are attracted to the gate electrode 4 side, and near the surface of the insulating film 5.
- the hole density is high.
- the voltage between the source electrode 2 and the drain electrode 3 is appropriately set, holes are injected from the source electrode 2 to the light-emitting layer 1 and the electrons from the drain electrode 3 to the light-emitting layer 1 depending on the control voltage applied to the gate electrode 4. Will be injected. That is, the source electrode 2 functions as a hole injection electrode, and the drain electrode 3 functions as an electron injection electrode. As a result, recombination of holes and electrons occurs in the light emitting layer 1, and light emission associated therewith occurs. This light emission state can be turned on and off or the light emission intensity can be changed by changing the control voltage applied to the gate electrode 4.
- a plurality of the light-emitting transistor elements 10 are two-dimensionally arranged on the substrate 20, whereby the display device 21 can be configured.
- An electric circuit diagram of the display device 21 is shown in FIG. That is, the display device 21 arranges the light emitting transistor elements 10 as described above in the pixels Pl1, P12,..., P21, P22,.
- the two-dimensional display is made possible by selectively causing the light-emitting transistor element 10 of each pixel to emit light and controlling the light emission intensity (luminance) of the light-emitting transistor element 10 of each pixel.
- the substrate 20 may be, for example, a silicon substrate in which the gate electrode 4 is integrated. That is, the gate electrode 4 may be formed of a conductive layer such as an impurity diffusion layer patterned on the surface of the silicon substrate. Also, use a glass substrate as the substrate 20.
- a selection transistor Ts for selecting each pixel and a data holding capacitor C are connected in parallel to the gate electrode 4 (G).
- the gates of the selection transistors Ts of the pixels Pl1, P12,..., P21, P22,... Aligned in the row direction are connected to a common scanning line LSI, LS2,. . Also, select the pixel in the ⁇ U direction [this pixel U Pl Pl, P21, ⁇ ; P12, P22, ⁇ ⁇ transistor Ts [where the light emitting transistor element 10 is on the opposite side] Are connected to common data lines LD1, LD2,... For each column.
- the pixels Pl1, P12, ...; P21, P22, ... in each row are cyclically selected sequentially from the scanning line driving circuit 61 controlled by the controller 63.
- a scanning drive signal for performing batch selection of a plurality of pixels in a row is given.
- the scanning line driving circuit 22 sets each row as a sequentially selected row, and conducts the selection transistors Ts of a plurality of pixels in the selected row at once, thereby collectively selecting the selection transistors Ts of a plurality of pixels in the non-selected row.
- a scanning drive signal for blocking can be generated.
- signals from the data line driving circuit 23 are inputted to the data lines LD1, LD2,.
- a control signal corresponding to the image data is input from the controller 24 to the data line driving circuit 23.
- the data line drive circuit 23 outputs a light emission control signal corresponding to the light emission gradation of each pixel in the selected row at the timing when a plurality of pixels in each row are selected at once by the scanning line drive circuit 21. Supply in parallel to....
- the light emission control signal is given to the gate electrode 4 (G) via the selection transistor Ts, so that the light emitting transistor element 10 of the pixel emits light.
- Light is emitted (or turned off) at a gradation corresponding to the control signal. Since the light emission control signal is held in the capacitor C, the potential of the gate electrode G is held even after the selected row by the scanning line driving circuit 61 is moved to another row, and the light emission state of the light emitting transistor element 10 is changed. Retained. In this way, two-dimensional display becomes possible.
- the organic EL device is capable of transporting holes and electrons, and emits light by recombination of holes and electrons.
- the light-emitting layer mainly contains the above pyrene-based compound, and holes are formed in the light-emitting layer.
- This organic EL element 30 is a laminate in which a hole injection electrode layer 32, a hole transport layer 33, a light emitting layer 34, an electron transport layer 35, and an electron injection electrode layer 36 are sequentially stacked on a substrate 31. A voltage is applied between the hole injection electrode layer 32 and the electron injection electrode layer 36 by a DC power source 37.
- the substrate 31 supports the organic EL element 30.
- the substrate 31 is made of a transparent material such as a glass substrate when light generated in the light emitting layer 34 is allowed to pass outside.
- the hole injection electrode layer 32 is a layer that receives application of a positive voltage from the DC power source 37.
- the material is not particularly limited as long as it has conductivity, but when the light generated in the light emitting layer 34 is emitted to the outside through the substrate 31, the hole injection electrode layer 32 also needs to have transparency.
- a hole injection electrode layer indium tin oxide (ITO) or the like can be used.
- the electron injection electrode layer 36 is a layer that receives a negative voltage applied from a DC power source 37.
- the material is not particularly limited as long as it has conductivity, and for example, aluminum or the like is used.
- a transparent material such as ITO as the electron injection electrode layer 36.
- the hole transport layer 33 is a layer for sending holes generated in the hole injection electrode layer 32 to the light emitting layer 34, and the electron transport layer 35 is generated in the electron injection electrode layer 36. This is a layer for sending electrons to the light emitting layer 34.
- the hole injecting electrode layer 32 and the electron injecting electrode layer 36 may be directly laminated with the light emitting layer 34. However, due to the problem of bonding properties between them, the hole injecting electrode layer 32 Alternatively, the electron-injecting electrode layer 36 and the light-emitting layer 34 are provided with a layer having good bonding properties and good hole or electron mobility as the hole-transporting layer 33 or the electron-transporting layer 35. is there . Therefore, depending on the combination of the hole injection electrode layer 32 or the electron injection electrode layer 36, the light emitting layer 34, and the material, the hole transport layer 33 and the electron transport layer 35 may not be provided.
- the material constituting the hole transport layer 33 includes N, N, diphenyl N, N, bis (3 methylphenol) 1, 1, biphenol 4, 4, 4, diamin (TPD).
- the material constituting the electron transport layer 35 is 3- (4-biphenyl) -4-phenol 2-ru 5- (4 t-butylphenol) -1, 2, 4-triazole (TAZ), etc. Can be raised
- the light emitting layer 34 is the same layer as the light emitting layer 10 of the light emitting transistor element, and is a layer using the pyrene-based compound as a main constituent, and the sub constituents are used together as necessary. .
- the hole transport layer 33 and the electron transport layer 35 have good electron mobility, and good bonding property between the hole injection electrode 32 and the electron injection electrode 36 and the light emitting layer 34.
- a hole injection layer is provided between the hole injection electrode layer 32 and the hole transport layer 33, or the electron injection electrode layer 36 and An electron injection layer may be provided between the electron transport layer 35 and the electron transport layer 35.
- the above-described pyrene-based compound may be used as the main constituent of the organic phosphor constituting the light-emitting layer 34, or the main constituent It is preferable to use Alq3 (tris (8-hydroxyquinolate)) or the like and use the above pyrene compound as a dopant.
- the light emitting layer 34 preferably has a predetermined range of differences between the HOMO energy level and the LUMO energy level, light emission luminance, PL light emission efficiency, and external light emission efficiency.
- the pyrene compounds having the above characteristics are used, it is possible to enhance the functions of each by adding sub-components such as the dopant. It becomes.
- the difference between the HOMO energy level and the LUMO energy level is the same as that of the light-emitting transistor element.
- the light emission luminance is a light emission amount corresponding to the brightness of an object that humans feel when looking at the object, and it is preferably as large as possible.
- This luminance can be measured using a Si photodiode.
- the emission luminance (c dZm 2 ) generated by the applied current (or voltage) is different.
- LOmAZcm 2 current voltage 6. OV
- LOOmAZcm 2 current voltage 8. OV
- LOOOcdZm 2 or more preferably tool 2000 cd / m 2 or more is more preferable.
- the PL luminous efficiency is as described above, and the external luminous efficiency is the luminous efficiency observed outside. This external luminous efficiency is usually said to be 5% as the upper limit for the fluorescent dyes used.
- the degree of light emission is large, and in PL light emission efficiency, 80% or more is preferable and 85% or more is more preferable.
- the upper limit of PL luminous efficiency is 100%. Further, in the external luminous efficiency, 1% or more is preferable 1.4% or more is preferable, and 2% or more is more preferable.
- the upper limit of EL luminous efficiency is said to be 5%.
- the organic EL element 30 is characterized by the wavelength of emitted light.
- This wavelength is within the range of visible light, but has a wavelength that varies depending on the type of organic phosphor used, particularly the pyrene compound. Various colors can be developed by combining organic phosphors having different wavelengths. For this reason, the wavelength of the emitted light exhibits its characteristics.
- the organic EL element 30 can be formed by forming a hole injection electrode layer 32 on a substrate 31 and sequentially vacuum-depositing each layer thereon.
- the film thickness of the light emitting layer 34 of the organic EL element 30 to be obtained should be about 10 to: LOOnm, and the film thickness of the hole transport layer 33 and the electron transport layer 35 may be about 10 to 50 nm.
- the hole injection electrode layer 32 and the electron injection electrode layer 36 may have a film thickness of about 5 to 30 nm.
- the operation of the organic EL element 30 is as follows. First, a voltage is applied between the hole injection electrode layer 32 and the electron injection electrode layer 36 by a DC power source 37.
- Holes generated in the hole injection electrode layer 32 are sent to the light emitting layer 34 through the hole transport layer 33.
- the electrons generated in the electron injection electrode layer 36 are sent to the light emitting layer 34 through the electron transport layer 35. Then, in the light emitting layer 34, holes and electrons are recombined to emit light.
- a plurality of the organic EL elements 30 are two-dimensionally arranged on the substrate 40, whereby a display device can be configured.
- a display device 41 an example of an electric circuit diagram of a passive display device 41 is shown in FIG.
- the scanning lines (LSI ', LS2, ...) and the data lines (LD1', LD2, ...) are arranged on the substrate 40 in a grid pattern, and at each intersection, An organic EL element 30 is arranged.
- the organic EL element (1, 1) in the first row and the first column has one end connected to the first row scanning line and the other end arranged in the first column data line.
- the organic EL element (j, i) in the j-th row and the i-th column has one end connected to the j-th scanning line and the other end arranged in the example data line.
- the organic EL element (j, i) emits light when current flows when the data line i is set to the noise level and the scanning line j is set to the low level.
- the light emission gradation can be controlled by adjusting the period during which this current flows.
- the scanning line driving circuit 42 selects a scanning line corresponding to a row to be emitted, sets it to a low level (eg, OV), and sets a scanning line corresponding to a row that does not emit light to a high level.
- the data line driving circuit 43 supplies a data signal pulse-modulated in accordance with the light emission gradation to the data line as high level data for a predetermined period. As a result, the selected organic EL element can emit light and an image can be displayed.
- the selected EL elements emit light in order by switching the scanning lines to be selected in order, so that the images can be changed in order.
- reaction solution was concentrated with an evaporator, and the residue was separated by adding Kuroguchi form and pure water, and the aqueous layer was extracted with Kuroguchi form.
- the organic layer was dried over anhydrous magnesium sulfate and concentrated. Hexane was added to the collection residue, and the precipitate was collected by suction filtration to obtain 5.9 g of dodecylbilene at a yield of 64%.
- 1-dodecyl-3,6,8-tribromopyrene 3. Og, 2-naphthyl boric acid (manufactured by Aldrich: reagent) in a 500 ml four-necked flask equipped with a reflux condenser, three-way cock, and thermometer 4 4g, Sodium carbonate (Kanto Chemical Co., Ltd .: Reagent) 5.3g, Toluene (Pure Chemical Co., Ltd .: Reagent) 1 20ml, Ethanol (Pure Chemical Co., Ltd .: Reagent) 60ml, Pure water 30ml was added.
- the organic layer was separated and the aqueous layer was extracted twice with 50 ml of CHC13.
- the recovered organic layer was washed with 200 ml of pure water, dehydrated and filtered with anhydrous magnesium sulfate, and then concentrated with an evaporator.
- the obtained solid was subjected to column chromatography (Si02, CHC13) to remove highly polar components, and then the distillate was concentrated and the resulting solid was purified by GPC to obtain 2. lg of a yellow solid.
- the organic layer was separated and the aqueous layer was extracted with 1350 ml of CHC.
- the collected organic layer was washed with 100 ml of pure water, dehydrated and filtered with anhydrous magnesium sulfate, and then concentrated with an evaporator. Hexane was added to the resulting residue and refluxed, and Pd and other inorganic salts remaining were removed by hot filtration.
- the precipitated solid was collected by suction filtration, and this solid was recrystallized again with hexane.
- the collected solid was desalted by column chromatography (Si02, CHC13-acetone) and purified by GPC to obtain 1. lg of yellow solid. It was identified as 1-dodecyl-1,3,6,8-tri (3-pyridyl) pyrene from FAB mass spectrometry (M + l: 602) and NMR.
- the obtained solid was recrystallized from toluene and further purified by GPC to obtain a yellow solid lg.
- a four-necked flask was equipped with a dropping funnel, a reflux condenser, a three-way cock, and a thermometer to perform nitrogen substitution.
- Pyrene manufactured by Aldrich: reagent
- 20.0 g and 200 mL of DMF were added, nitrogen substitution was performed again, and heating was performed at an internal temperature of 70 ° C to dissolve pyrene.
- NBS manufactured by Tokyo Chemical Industry Co., Ltd .: Reagent
- 108.9 g was dissolved in 400 mL of DMF, and this was dropped over 20 minutes from the dropping funnel.
- the obtained crude product was recrystallized from o-dichloromouth benzene having a volume 15 times the amount of the sample, and grayish white acicular crystals were recovered. According to LC analysis power, the purity of the recovered material was 91%. (Dibromopyrene and tetrabromopyrene were confirmed as other components.)
- a 200 ml three-necked flask was equipped with a reflux condenser, a nitrogen line-connected three-way cock, a dropping funnel, and a thermometer, and the inside of the reactor was replaced with nitrogen.
- 6.2 g of 1, 3, 6-trifluoroethylene and 80 ml of DM F (manufactured by Junsei Chemical Co., Ltd .: Reagent) were added and stirred at an internal temperature of 90 ° C.
- a solution prepared by dissolving 6 g of NBS in 20 ml of DMF was dropped from the dropping funnel over 5 minutes, and the mixture was stirred at 90 ° C. for 1 hour.
- Tetrakistriphenylphosphine palladium (0) 0.7 g was prepared and heated and stirred at 80 ° C. for 12 hours in an oil bath.
- the formed precipitate was collected by suction filtration, and the solid was washed with MeOH.
- the recovered solid was dissolved in toluene at a heating reflux temperature and subjected to hot filtration to remove inorganic salts.
- the filtrate was concentrated and washed with MeOH to obtain the desired product (yield: 2.0 g, yield: 90%).
- Carrier mobility, EL luminous efficiency, and PL luminous efficiency were measured and calculated as follows.
- drain voltage (V) and drain current of organic semiconductor are expressed by the following formula (1).
- V Gate threshold voltage [V] (This is because the drain voltage (V) in the saturation region is constant.
- Plot drain current LZ square (V 1/2 ) against gate voltage (V) Indicates the point that intersects the axis. )
- the gate voltage was operated from OV to 100V in -20V steps up to 100V, in steps of -20V, and the luminescence emitted from the device was measured with a photon counter (made by Newport: 4155C Semiconductor Parameter Analyzer) and obtained there.
- a photon counter made by Newport: 4155C Semiconductor Parameter Analyzer
- the photon number [C PS] was converted into the luminous flux [lw] using the following formula (3)
- the EL luminous efficiency 7? Ext was calculated using the following formula (4).
- N Number of photons observed by photon counter (PC) [CPS]
- the luminous efficiency of PL is that the material obtained in the present invention is applied on a quartz substrate in a nitrogen atmosphere. After forming a single-layer film by vapor deposition at 70 nm, an integrating sphere (IS—060, Labsphere Co.) is used to irradiate a He—Cd laser (IK5651R—G, Kimmon electric Co.) with a wavelength of 325 nm as excitation light. The emission was calculated by measuring the multi-channel photodiode (PMA-11, Hamamatsu photonics Co.) from the sample.
- the organic EL device shown in FIG. 9 was manufactured under the following conditions.
- Electron injection electrode 36 ... Ag (10nm)
- Example 1 The measurement was conducted in the same manner as in Example 1 except that tetraphenylene (manufactured by Aldrich: reagent, abbreviated as “TPPy”) was used as the pyrene compound.
- TPPy tetraphenylene
- Table 1 PL luminous efficiency and external luminous efficiency indicate luminous efficiency as the luminous layer 34 (content of asymmetric pyrene compound: 6% by weight).
- the light-emitting transistor device shown in FIGS. 5 and 6 was manufactured under the following conditions.
- Source electrode 2 and drain electrode 3 Each electrode having a comb-shaped portion (Au, thickness 40 nm) having a comb-tooth force of 20 is formed, and each comb-teeth is formed as shown in FIG. It was arranged on the insulating film 5 so that the shape portions were alternately arranged. At this time, a layer (lnm) having a chrome force was provided between the insulating film 5 and both electrodes. At this time, the width of the channel portion (between each comb-shaped portion) was 25 ⁇ m and the length was 4 mm.
- Luminescent layer 1 ⁇ Luminescent layer 1 ⁇ The pyrene compounds (Fig. 2 (a) (4-5) and (4 7)) obtained by the above-mentioned production method are each independently used as an insulating film, a source electrode 2 and The light emitting layer 1 was formed by vapor deposition so as to cover the periphery of the drain electrode 3.
- EL luminous efficiency ⁇ 7.4 ⁇ 1 ( ⁇ 3 9.0 ⁇ 1 ( ⁇ 2 Luminance brightness (CPS) ⁇ 3.5X10 5 1.2X10 6 Carrier mobility (cmVV-s) ⁇ 4.9X10— 5 5.5X10— 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05809745A EP1818322A4 (en) | 2004-11-25 | 2005-11-25 | PYRENE COMPOUND, AND LIGHT EMITTING DEVICE DEVICE AND LIGHT EMITTING DEVICE USING THE SAME |
US11/791,613 US20080012475A1 (en) | 2004-11-25 | 2005-11-25 | Pyrene Based Compound, And Light Emitting Transistor Element And Electroluminescence Element Using The Same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004340944 | 2004-11-25 | ||
JP2004-340944 | 2004-11-25 | ||
JP2005-282590 | 2005-09-28 | ||
JP2005282590A JP2006176494A (ja) | 2004-11-25 | 2005-09-28 | ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006057325A1 true WO2006057325A1 (ja) | 2006-06-01 |
Family
ID=36498059
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2005/021647 WO2006057325A1 (ja) | 2004-11-25 | 2005-11-25 | ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20080012475A1 (ja) |
EP (1) | EP1818322A4 (ja) |
JP (1) | JP2006176494A (ja) |
KR (1) | KR20070093401A (ja) |
TW (1) | TW200631925A (ja) |
WO (1) | WO2006057325A1 (ja) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008150365A (ja) * | 2006-11-20 | 2008-07-03 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2009013066A (ja) * | 2007-06-29 | 2009-01-22 | Tdk Corp | ペリレン誘導体及びその前駆物質の製造方法 |
EP1808912A3 (en) * | 2006-01-16 | 2010-08-11 | LG Display Co., Ltd. | Electron transport compound and organic light emitting device comprising the same |
US7781076B2 (en) | 2007-06-26 | 2010-08-24 | Eastman Kodak Company | Heteropyrene-based semiconductor materials for electronic devices and methods of making the same |
CN101003508B (zh) * | 2006-01-16 | 2010-11-24 | 乐金显示有限公司 | 电子传输化合物和包含该化合物的有机发光器件 |
WO2011030493A1 (en) * | 2009-09-14 | 2011-03-17 | Canon Kabushiki Kaisha | Novel pyrene compound and organic electroluminescent device including the same |
WO2011077691A1 (ja) | 2009-12-21 | 2011-06-30 | 出光興産株式会社 | ピレン誘導体を用いた有機エレクトロルミネッセンス素子 |
US8729530B2 (en) * | 2006-06-15 | 2014-05-20 | Toray Industries, Inc. | Material for light-emitting device and light-emitting device |
WO2015068987A1 (ko) * | 2013-11-08 | 2015-05-14 | (주)씨에스엘쏠라 | 신규한 유기화합물, 이를 포함하는 유기전계발광소자 및 전자 기기 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4355796B2 (ja) * | 2003-08-29 | 2009-11-04 | 国立大学法人京都大学 | 有機半導体装置およびその製造方法 |
JP2007015961A (ja) | 2005-07-06 | 2007-01-25 | Idemitsu Kosan Co Ltd | ピレン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子 |
JP5017884B2 (ja) * | 2006-02-24 | 2012-09-05 | 東レ株式会社 | 発光素子材料および発光素子 |
JP5093879B2 (ja) * | 2006-03-20 | 2012-12-12 | 国立大学法人京都大学 | ピレン系有機化合物、トランジスタ材料及び発光トランジスタ素子 |
CN101553940B (zh) * | 2006-11-14 | 2010-10-13 | 出光兴产株式会社 | 有机薄膜晶体管和有机薄膜发光晶体管 |
EP2083457A4 (en) * | 2006-11-14 | 2012-04-25 | Idemitsu Kosan Co | ORGANIC THIN FILM TRANSISTOR AND ORGANIC THIN FILM LIGHT TRANSISTOR |
JP5428147B2 (ja) * | 2006-12-07 | 2014-02-26 | 三菱化学株式会社 | 有機蛍光体材料 |
JP2008252063A (ja) * | 2007-03-07 | 2008-10-16 | Toray Ind Inc | 発光素子材料および発光素子 |
CN101627102B (zh) * | 2007-03-07 | 2013-08-28 | 东丽株式会社 | 发光元件材料和发光元件 |
JP5117763B2 (ja) * | 2007-05-21 | 2013-01-16 | 山本化成株式会社 | 有機トランジスタ |
JP5144155B2 (ja) * | 2007-07-24 | 2013-02-13 | 山本化成株式会社 | 有機トランジスタ |
JP5194623B2 (ja) * | 2007-08-03 | 2013-05-08 | 三菱化学株式会社 | テトラアリールピレン化合物、電荷輸送材料、有機電界発光素子用材料、有機電界発光素子用組成物および有機電界発光素子 |
KR101496846B1 (ko) | 2008-12-24 | 2015-03-02 | 삼성디스플레이 주식회사 | 유기 발광 트랜지스터를 포함하는 표시 장치 및 이의 제조 방법 |
KR101314383B1 (ko) | 2009-07-15 | 2013-10-04 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
JP5523016B2 (ja) * | 2009-08-20 | 2014-06-18 | キヤノン株式会社 | 複素環化合物及びこれを用いた有機発光素子 |
EP2483366A4 (en) * | 2009-09-29 | 2013-05-01 | Du Pont | DEUTERATED COMPOUNDS FOR LUMINESCENT APPLICATIONS |
KR101202347B1 (ko) | 2009-10-09 | 2012-11-16 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자 |
US20120168733A1 (en) * | 2009-12-21 | 2012-07-05 | Idemitsu Kosan Co., Ltd. | Pyrene derivative and organic electroluminescent element using the same |
DE102010006280A1 (de) * | 2010-01-30 | 2011-08-04 | Merck Patent GmbH, 64293 | Farbkonvertierung |
US8546793B2 (en) | 2010-10-26 | 2013-10-01 | Samsung Display Co., Ltd. | Organic light-emitting device |
KR101334204B1 (ko) * | 2010-10-27 | 2013-11-28 | (주)위델소재 | 신규한 파이렌 화합물과, 상기 파이렌 화합물의 제조방법 및 상기 파이렌 화합물을 이용한 유기발광소자 |
KR101511168B1 (ko) | 2011-06-16 | 2015-04-10 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
CN102363623A (zh) * | 2011-08-16 | 2012-02-29 | 杭州师范大学 | 一类基于四取代芘的发光材料及其制备方法与应用 |
CN103664748B (zh) * | 2012-09-03 | 2016-05-11 | 乐金显示有限公司 | 芘化合物以及包含该化合物的有机发光二极管设备 |
KR101661925B1 (ko) * | 2014-03-03 | 2016-10-05 | 한국교통대학교산학협력단 | 파이렌 유도체 및 이를 이용한 유기전계발광소자 |
JPWO2016133058A1 (ja) * | 2015-02-18 | 2017-11-30 | Tdk株式会社 | 電界発光素子 |
KR101661742B1 (ko) | 2015-03-30 | 2016-09-30 | 임광민 | 히드록시 화합물의 제조방법 |
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 |
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 |
CN110183419A (zh) * | 2019-05-18 | 2019-08-30 | 南京工业大学 | 1,3,6,8位四取代芘衍生物的合成及其在有机场效应晶体管中的应用 |
WO2021107030A1 (ja) * | 2019-11-26 | 2021-06-03 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子及び電子機器 |
JP2024004495A (ja) * | 2020-09-30 | 2024-01-17 | 出光興産株式会社 | 重水素化芳香族化合物の製造方法 |
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 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09241629A (ja) * | 1996-03-08 | 1997-09-16 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2001118682A (ja) * | 1999-10-21 | 2001-04-27 | Fujitsu Ltd | 有機エレクトロルミネッセンス素子 |
JP2001192651A (ja) * | 1999-10-26 | 2001-07-17 | Fuji Photo Film Co Ltd | 芳香族縮環化合物、発光素子材料およびそれを使用した発光素子 |
JP2002063988A (ja) * | 2000-08-22 | 2002-02-28 | Toray Ind Inc | 発光素子 |
JP2003300912A (ja) * | 2002-02-07 | 2003-10-21 | Fuji Photo Film Co Ltd | 芳香族縮環化合物の製造方法 |
WO2004096945A1 (ja) * | 2003-05-01 | 2004-11-11 | Fujitsu Limited | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
WO2004096743A1 (ja) * | 2003-04-28 | 2004-11-11 | Fujitsu Limited | 有機エレクトロルミネッセンス素子 |
JP2005126431A (ja) * | 2003-10-03 | 2005-05-19 | Semiconductor Energy Lab Co Ltd | ピレン誘導体、発光素子、および発光装置、並びに電気器具 |
WO2005108348A1 (ja) * | 2004-05-12 | 2005-11-17 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体、それを用いた有機エレクトロルミネッセンス素子及び芳香族アミン誘導体の製造方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002215065A (ja) * | 2000-11-02 | 2002-07-31 | Seiko Epson Corp | 有機エレクトロルミネッセンス装置及びその製造方法、並びに電子機器 |
JP3841695B2 (ja) * | 2002-02-06 | 2006-11-01 | 富士写真フイルム株式会社 | 有機el素子及び有機elディスプレイ |
JP4878429B2 (ja) * | 2002-07-22 | 2012-02-15 | 株式会社リコー | 能動素子及びそれを有するel表示素子 |
US7571894B2 (en) * | 2003-04-28 | 2009-08-11 | Fuji Photo Film Co., Ltd. | Organic electroluminescence element |
US7232619B2 (en) * | 2003-10-03 | 2007-06-19 | Semiconductor Energy Laboratory Co., Ltd. | Pyrene derivative, light emitting element, and light emitting device |
-
2005
- 2005-09-28 JP JP2005282590A patent/JP2006176494A/ja active Pending
- 2005-11-25 US US11/791,613 patent/US20080012475A1/en not_active Abandoned
- 2005-11-25 KR KR1020077014336A patent/KR20070093401A/ko not_active Application Discontinuation
- 2005-11-25 WO PCT/JP2005/021647 patent/WO2006057325A1/ja active Application Filing
- 2005-11-25 TW TW094141448A patent/TW200631925A/zh unknown
- 2005-11-25 EP EP05809745A patent/EP1818322A4/en not_active Withdrawn
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09241629A (ja) * | 1996-03-08 | 1997-09-16 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2001118682A (ja) * | 1999-10-21 | 2001-04-27 | Fujitsu Ltd | 有機エレクトロルミネッセンス素子 |
JP2001192651A (ja) * | 1999-10-26 | 2001-07-17 | Fuji Photo Film Co Ltd | 芳香族縮環化合物、発光素子材料およびそれを使用した発光素子 |
JP2002063988A (ja) * | 2000-08-22 | 2002-02-28 | Toray Ind Inc | 発光素子 |
JP2003300912A (ja) * | 2002-02-07 | 2003-10-21 | Fuji Photo Film Co Ltd | 芳香族縮環化合物の製造方法 |
WO2004096743A1 (ja) * | 2003-04-28 | 2004-11-11 | Fujitsu Limited | 有機エレクトロルミネッセンス素子 |
WO2004096945A1 (ja) * | 2003-05-01 | 2004-11-11 | Fujitsu Limited | 1,3,6,8−四置換ピレン化合物、有機el素子及び有機elディスプレイ |
JP2005126431A (ja) * | 2003-10-03 | 2005-05-19 | Semiconductor Energy Lab Co Ltd | ピレン誘導体、発光素子、および発光装置、並びに電気器具 |
WO2005108348A1 (ja) * | 2004-05-12 | 2005-11-17 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体、それを用いた有機エレクトロルミネッセンス素子及び芳香族アミン誘導体の製造方法 |
Non-Patent Citations (11)
Title |
---|
CHEMICAL ABSTRACTS, vol. 103, 1985, Columbus, Ohio, US; abstract no. 87615, XP008062509 * |
CHEMICAL ABSTRACTS, vol. 105, 1986, Columbus, Ohio, US; abstract no. 78625, XP008062508 * |
CHEMICAL ABSTRACTS, vol. 120, 1994, Columbus, Ohio, US; abstract no. 94411, XP008062507 * |
CHEMICAL ABSTRACTS, vol. 131, no. 15, 1999, Columbus, Ohio, US; abstract no. 199379, XP008062505 * |
CHEMICAL ABSTRACTS, vol. 136, no. 14, 2002, Columbus, Ohio, US; abstract no. 216806, XP008062504 * |
CHEMICAL ABSTRACTS, vol. 32, 1938, Columbus, Ohio, US; abstract no. 145I, XP008062515 * |
CHEMICAL ABSTRACTS, vol. 36, 1942, Columbus, Ohio, US; abstract no. 87F-I, 88A-I, XP008062514 * |
CHEMICAL ABSTRACTS, vol. 69, 1968, Columbus, Ohio, US; abstract no. 86693, XP008062512 * |
CHEMICAL ABSTRACTS, vol. 73, 1970, Columbus, Ohio, US; abstract no. 35116, XP008062511 * |
CHEMICAL ABSTRACTS, vol. 77, 1972, Columbus, Ohio, US; abstract no. 88143, XP008062510 * |
See also references of EP1818322A4 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101003508B (zh) * | 2006-01-16 | 2010-11-24 | 乐金显示有限公司 | 电子传输化合物和包含该化合物的有机发光器件 |
EP1808912A3 (en) * | 2006-01-16 | 2010-08-11 | LG Display Co., Ltd. | Electron transport compound and organic light emitting device comprising the same |
US7811681B2 (en) | 2006-01-16 | 2010-10-12 | Lg Display Co., Ltd. | Electron transport compound and organic light emitting device comprising the same |
US8729530B2 (en) * | 2006-06-15 | 2014-05-20 | Toray Industries, Inc. | Material for light-emitting device and light-emitting device |
JP2008150365A (ja) * | 2006-11-20 | 2008-07-03 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
US7781076B2 (en) | 2007-06-26 | 2010-08-24 | Eastman Kodak Company | Heteropyrene-based semiconductor materials for electronic devices and methods of making the same |
JP2009013066A (ja) * | 2007-06-29 | 2009-01-22 | Tdk Corp | ペリレン誘導体及びその前駆物質の製造方法 |
WO2011030493A1 (en) * | 2009-09-14 | 2011-03-17 | Canon Kabushiki Kaisha | Novel pyrene compound and organic electroluminescent device including the same |
JP2011057651A (ja) * | 2009-09-14 | 2011-03-24 | Canon Inc | 新規ピレン化合物およびそれを有する有機el素子 |
US9169176B2 (en) | 2009-09-14 | 2015-10-27 | Canon Kabushiki Kaisha | Pyrene compound and organic electroluminescent device including the same |
WO2011077691A1 (ja) | 2009-12-21 | 2011-06-30 | 出光興産株式会社 | ピレン誘導体を用いた有機エレクトロルミネッセンス素子 |
US9353027B2 (en) | 2009-12-21 | 2016-05-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element using pyrene derivative |
WO2015068987A1 (ko) * | 2013-11-08 | 2015-05-14 | (주)씨에스엘쏠라 | 신규한 유기화합물, 이를 포함하는 유기전계발광소자 및 전자 기기 |
Also Published As
Publication number | Publication date |
---|---|
KR20070093401A (ko) | 2007-09-18 |
EP1818322A1 (en) | 2007-08-15 |
EP1818322A4 (en) | 2009-11-04 |
US20080012475A1 (en) | 2008-01-17 |
TW200631925A (en) | 2006-09-16 |
JP2006176494A (ja) | 2006-07-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2006057325A1 (ja) | ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子 | |
JP5093879B2 (ja) | ピレン系有機化合物、トランジスタ材料及び発光トランジスタ素子 | |
TWI686397B (zh) | 多環芳香族化合物及發光層形成用組成物與其用途 | |
JP6066132B2 (ja) | ヘテロ環化合物およびこれを含む有機電子素子 | |
WO2006057326A1 (ja) | ピレン系化合物及びこれを用いた発光トランジスタ素子 | |
JP5709752B2 (ja) | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 | |
TW202041511A (zh) | 多環芳香族化合物、反應性化合物、高分子化合物、懸掛型高分子化合物、有機元件用材料、油墨組成物、有機電致發光元件、顯示裝置及照明裝置 | |
TW201945374A (zh) | 環烷基取代多環芳香族化合物、反應性化合物、高分子、懸掛型高分子、有機器件用材料、油墨組成物、有機電致發光元件、顯示裝置以及照明裝置 | |
TW202000675A (zh) | 三級烷基取代多環芳香族化合物、反應性化合物、高分子、懸掛型高分子、有機器件用材料、油墨組成物、有機電致發光元件、顯示裝置、照明裝置以及發光層形成用組成物 | |
TWI290582B (en) | Anthracene compound and organic electroluminescent device including the anthracene compound | |
JP2007084485A (ja) | ナフタレン誘導体及び有機半導体材料と、これを用いた発光トランジスタ素子及び有機エレクトロルミネッセンス素子 | |
TWI662013B (zh) | 化合物及其有機電子裝置 | |
JP6071390B2 (ja) | 新規有機化合物、それを有する有機発光素子及び表示装置 | |
CN111936504A (zh) | 环烷基取代多环芳香族化合物 | |
JP6221560B2 (ja) | 有機電界発光素子 | |
CN115867558A (zh) | 多环芳香族化合物 | |
JP2007258253A (ja) | トランジスタ材料及びこれを用いた発光トランジスタ素子 | |
KR20160142918A (ko) | 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자 | |
TW201806937A (zh) | 化合物及其有機電子裝置 | |
TW201412764A (zh) | 有機電場發光元件用材料及使用其的有機電場發光元件 | |
KR20160142915A (ko) | 유기 전계 발광 소자용 화합물, 이를 포함하는 유기 전계 발광 소자 | |
JP5807601B2 (ja) | アントラセン誘導体およびこれを用いた有機電界発光素子 | |
KR102012822B1 (ko) | 화합물 및 이를 이용한 유기 전자 소자 | |
JP2021080190A (ja) | 多環芳香族化合物 | |
CN109942548A (zh) | 经喹啉取代的二苯基嘧啶化合物及其有机电致发光元件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KM KN KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 200580040399.5 Country of ref document: CN Ref document number: 2005809745 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020077014336 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11791613 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2005809745 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 11791613 Country of ref document: US |