WO2004013080A1 - Spirobifluorene derivatives, their preparation and uses thereof - Google Patents
Spirobifluorene derivatives, their preparation and uses thereof Download PDFInfo
- Publication number
- WO2004013080A1 WO2004013080A1 PCT/EP2003/008465 EP0308465W WO2004013080A1 WO 2004013080 A1 WO2004013080 A1 WO 2004013080A1 EP 0308465 W EP0308465 W EP 0308465W WO 2004013080 A1 WO2004013080 A1 WO 2004013080A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- derivatives
- spirobifluorene
- radical anions
- spirobifluorene derivatives
- sbf
- Prior art date
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- 0 **C(c1ccc2-c3ccc(*)cc3C3(c(cc(*)cc4)c4-c4ccc(*)cc34)c2c1)=O Chemical compound **C(c1ccc2-c3ccc(*)cc3C3(c(cc(*)cc4)c4-c4ccc(*)cc34)c2c1)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- 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
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
-
- 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
- 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
-
- 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
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- A can be selected in the group of the following derivatives: phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-thienyl, 2-furyl, 2-pyrrolyl, 3-thienyl, 3-furyl, 3-pyrrolyl, 9-anthryl, biphenylenyl, perylenyl, fullerenyl, and corresponding derivatives, said derivatives being preferably substituted by at least one R group and/or an R' group, wherein R and R' have the meaning above indicated.
- the following compounds are particularly preferred: - the compounds of formula (III):
- the radical anions of the compounds (VII), (Villa, Vlllb), (IX) and (Xa, Xb) are particularly preferred.
- the electrochemical method for obtaining the radical anions in general is described in (5). This method is performed using an electrochemical cell comprising two compartments: one anodic and one cathodic; the cathodic compartment contains a working electrode and a calomel reference electrode.
- An aprotic solvent is made anhydrous by means of usual procedures (5); a supporting electrolyte is added to it, also made anhydrous, in order to obtain a concentration between 1 M and 0.01 M, preferably 0.2 M and 0.05 M, particularly preferably approximately 0.1 M.
- a general preparation is given in the following in the experimental part.
- the reaction mixture is allowed reaching room temperature (RT) then heated, refluxing for 1 hour.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/523,101 US7557249B2 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and uses thereof |
AU2003260342A AU2003260342A1 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and uses thereof |
EP03766376A EP1534661B1 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and uses thereof |
JP2004525396A JP4572113B2 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and use |
DE60336907T DE60336907D1 (en) | 2002-08-01 | 2003-07-31 | SPIROBIFLUORENE DERIVATIVES, THEIR PREPARATION AND THEIR USE |
US12/497,195 US8188462B2 (en) | 2002-08-01 | 2009-07-02 | Spirobifluorene derivatives, their preparation and uses thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITRM2002A000411 | 2002-08-01 | ||
IT000411A ITRM20020411A1 (en) | 2002-08-01 | 2002-08-01 | SPIROBIFLUORENE DERIVATIVES, THEIR PREPARATION AND USE. |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/523,101 Substitution US7557249B2 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and uses thereof |
US12/497,195 Continuation US8188462B2 (en) | 2002-08-01 | 2009-07-02 | Spirobifluorene derivatives, their preparation and uses thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004013080A1 true WO2004013080A1 (en) | 2004-02-12 |
Family
ID=11456438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/008465 WO2004013080A1 (en) | 2002-08-01 | 2003-07-31 | Spirobifluorene derivatives, their preparation and uses thereof |
Country Status (9)
Country | Link |
---|---|
US (2) | US7557249B2 (en) |
EP (1) | EP1534661B1 (en) |
JP (1) | JP4572113B2 (en) |
KR (1) | KR100969179B1 (en) |
CN (1) | CN100338022C (en) |
AU (1) | AU2003260342A1 (en) |
DE (1) | DE60336907D1 (en) |
IT (1) | ITRM20020411A1 (en) |
WO (1) | WO2004013080A1 (en) |
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JP2006339577A (en) * | 2005-06-06 | 2006-12-14 | Konica Minolta Holdings Inc | Organic semiconductor thin film and organic thin film transistor |
US7345301B2 (en) | 2003-04-15 | 2008-03-18 | Merck Patent Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
US7651791B2 (en) * | 2005-12-15 | 2010-01-26 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and electroluminescence device employing the same |
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US7557249B2 (en) | 2009-07-07 |
KR20060093800A (en) | 2006-08-25 |
AU2003260342A1 (en) | 2004-02-23 |
US8188462B2 (en) | 2012-05-29 |
EP1534661A1 (en) | 2005-06-01 |
ITRM20020411A0 (en) | 2002-08-01 |
US20060006365A1 (en) | 2006-01-12 |
DE60336907D1 (en) | 2011-06-09 |
EP1534661B1 (en) | 2011-04-27 |
JP4572113B2 (en) | 2010-10-27 |
KR100969179B1 (en) | 2010-07-08 |
ITRM20020411A1 (en) | 2004-02-02 |
JP2005538999A (en) | 2005-12-22 |
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US20090302274A1 (en) | 2009-12-10 |
CN1678561A (en) | 2005-10-05 |
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