[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

EP0848739A1 - Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents - Google Patents

Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents

Info

Publication number
EP0848739A1
EP0848739A1 EP96930152A EP96930152A EP0848739A1 EP 0848739 A1 EP0848739 A1 EP 0848739A1 EP 96930152 A EP96930152 A EP 96930152A EP 96930152 A EP96930152 A EP 96930152A EP 0848739 A1 EP0848739 A1 EP 0848739A1
Authority
EP
European Patent Office
Prior art keywords
formula
same
different
structural units
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96930152A
Other languages
German (de)
English (en)
Inventor
Willi Kreuder
Hans-Heinrich HÖRHOLD
Henning Rost
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Hoechst Research and Technology Deutschland GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE1995132574 external-priority patent/DE19532574A1/de
Priority claimed from DE1995135938 external-priority patent/DE19535938A1/de
Application filed by Hoechst Research and Technology Deutschland GmbH and Co KG filed Critical Hoechst Research and Technology Deutschland GmbH and Co KG
Publication of EP0848739A1 publication Critical patent/EP0848739A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

Definitions

  • Liquid crystal display elements have been around for some time
  • Electroluminescent device with a radiation source described consisting of a layer of an amorphous or predominantly amorphous polymer material with noticeable electric charge mobility and low ionization potential, a strong electron donor, a strong electron acceptor and
  • At least one luminescent additive there is preferably at least one luminescent additive, electrical connections being provided through which an electrical current can be passed therethrough through the thickness of the layer to excite radiation.
  • Conjugated polymers such as poly (p-phenylene vinylene) (see, for example, WO-A 90/13148) and non-conjugated polymers have been used as polymer materials (see, for example, I. Sokolik et al., J. Appl. Phys. 1 993, 74, 3584), wherein conjugated materials generally have the advantage of a higher Carrier mobility and thus better efficiencies and lower threshold voltages.
  • electroluminescent materials in particular based on polymers, can in no way be regarded as complete, the manufacturers of lighting and display devices are interested in a wide variety of electroluminescent materials for such devices.
  • Electroluminescent materials with the other components of the devices allow conclusions on the quality of the electroluminescent material.
  • the object of the present invention was therefore to create new ones
  • Lighting or display devices are suitable to improve the property profile of these devices.
  • Triarylamine units are particularly suitable as electroluminescent materials.
  • Such compounds are sometimes used as photosensitive components for Electrophotographic processes and known as sensitizers for electrically photosensitive dyes (US Pat. No. 4,323,203), a suitability as
  • electroluminescent material cannot be derived from this.
  • the invention therefore relates to an electroluminescent material comprising one or more polymers which contain structural units of the formula (I)
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 are the same or different and / or
  • polynuclear optionally linked via one or more, preferably a bridge, and / or condensed aryl and / or
  • Heteroaryl groups preferably with 4 to 400, particularly preferably 4 to 100, very particularly preferably 4 to 20 carbon atoms, which can optionally be substituted, two of Ar 1 , Ar 3 , Ar 5 and Ar 6 and of Ar 2 and Ar 4 each run out of a bond;
  • R 1 is H, a hydrocarbon radical with 1 to 22 carbon atoms which may be optionally substituted, preferably with F, and may also contain heteroatoms, preferably 0, or Ar 7 , where Ar 7 has the same meanings as Ar 1, independently of Ar 1 -6 -6 has;
  • n 0, 1 or 2, preferably 0 or 1, particularly preferably 0.
  • the electroluminescent material according to the invention is characterized, inter alia, by a low threshold voltage for electroluminescence and high efficiency, even though the polymers are not conjugated. It is also particularly one of the components of multi-layer structures Hole conductor layer suitable.
  • electroluminescent materials are materials which can be used as an active layer in an electroluminescent device.
  • Active layer means that the layer is capable of emitting light when an electric field is applied (light-emitting layer) and / or that it improves the injection and / or the transport of the positive and / or negative charges (charge injection or charge transport layer).
  • the invention therefore also relates to the use of a polymer containing structural units of the formula (I) as an electroluminescent material, in particular as a hole conductor layer.
  • the polymers according to the invention generally have 2 to 1000,
  • Ar 1 , Ar 3 , Ar 5 , Ar 6 are the same or different, preferably the same
  • n 1 to 20, preferably 1, 2 or 3, particularly preferably 1,
  • Ar 2 , Ar 4 identical or different from Ar 1 , Ar 3 , Ar 5 and Ar 6 , have the same meanings as Ar 1 , Ar 3 , Ar 5 and Ar 6 , only one of the two possible binding sites to the polymer is realized;
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 can be substituted identically or differently with one or more radicals R 2 -R 7 ;
  • R 1 is H, a hydrocarbon radical having 1 to 22 carbon atoms or Ar 7 , where Ar 7 can have the same meanings as Ar 1 to Ar 6 ;
  • R 2 -R 7 are identical or different H, an alkyl group with 1 to 22,
  • R 8 identical or different from R 1 , has the same meanings as R 1 ; n is 0, 1 or 2, preferably 0 or 1, particularly preferably 0.
  • Ar 1 , Ar 3 , Ar 5 , Ar 6 are the same or different
  • n 1 to 20, preferably 1, 2 or 3, particularly preferably 1,
  • Ar 2 , Ar 4 have the same or different meanings as Ar 1 , Ar 3 ,
  • Polymer is realized, or are
  • R 9 -R 1 5 are the same or different F, Cl, a straight-chain or
  • R 1 2-1 5 can also be H.
  • the invention therefore also relates to polymers containing
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 are the same or different and / or
  • polynuclear optionally linked via one or more, preferably a bridge, and / or condensed aryl and / or
  • Heteroaryl groups preferably with 4 to 400, particularly preferably 4 to 100, very particularly preferably 4 to 20 carbon atoms, which can optionally be substituted, two of Ar 1 , Ar 3 , Ar 5 and Ar 6 and of Ar 2 and Ar 4 each run out of a bond;
  • R 1 is a carbon hydrogen residue with 1 to 22 carbon atoms
  • Ar 7 may optionally be substituted, preferably with F, and may also contain heteroatoms, preferably O, or Ar 7 , where Ar 7 has the same meanings as Ar 1 -6 independently of Ar 1 -6 ;
  • n 0, 1 or 2, preferably 0 or 1, particularly preferably 0.
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and R 1 are those given in formula (I)
  • Ar 6 has the meanings given in the formula (I) and Z represents C 1 -C 22 alkoxy, preferably ethoxy, or aryl radicals, preferably phenyl.
  • Condensing agent preferably of potassium tert-butoxide or sodium hydride.
  • the polycondensation is advantageously carried out in such a way that the equimolar mixture of the starting components (II) and (III) in one
  • Solvent is introduced and, under an inert gas atmosphere and stirring, preferably at least molar amounts of condensing agent are introduced in solution or suspension.
  • the condensing agent can also be introduced alone or with the biscetone in a solvent and the
  • Bisphosphorus component are added. Benzene, toluene, xylene or dimethylformamide are preferably used as solvents Reaction temperature is preferably 60 to 1 20 ° C and the reaction time 0.1 to 20, preferably 0.1 to 5, particularly preferably 0.1 to 1 hour. The implementations are almost quantitative.
  • Working up can be carried out by adding water, if appropriate an acid, such as acetic acid, and removing the organic reaction phases.
  • the condensation products obtained can be extracted for purification, e.g. with alcohols or acetic acid, or from solution in a solvent using a non-solvent.
  • This manufacturing process is generally described, for example, in DD 84 272,
  • the radicals R 1 in the formula (I) may also have different meanings. Furthermore, by delayed addition of given at least one of the comonomers the possibility of producing block copolymers.
  • Such compounds are suitable, especially in a mixture with the
  • Polymers according to the invention also as electroluminescent materials.
  • Macrocyclic compounds can form in the polymerization of starting compounds with meta-substituted structural elements.
  • the polymers according to the invention or used according to the invention can therefore also be present in a mixture with these macrocyclic compounds, which does not interfere with their use as electroluminescent material.
  • the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. It can also by itself
  • the bis (diphenylphosphine oxides) or bis (phosphonic acid esters) required as condensation components are easily accessible, for example, using the MichaelisArbusov reaction from the corresponding bis (halogenomethyl) compounds with ethyl diphenylphosphinate (C 6 H 5 ) 2 POC 2 H 5 or with triethyl phosphite.
  • aldehydes can be derived from bis-carboxylic acid derivatives controlled reduction with reducing agents such as lithium tris-alkoxyalanates or H 2 / Pd ("Rosenmund reduction”) can be obtained:
  • Bisaldehydes can be obtained from bischloromethyl precursors, for example, by the sommelet reaction
  • R 1 in formula (I) is not hydrogen, bisketones are considered as Starting materials used.
  • Bisketones can also be produced by Friedel-Crafts acylation:
  • the starting compounds for bisaldehydes and bisketones are the tertiary, aromatic amines (IV) and (V). They can be classified according to the known
  • tertiary aromatic Amines for example, can also be prepared by the process given in Scheme 1.
  • N- (alkylaryl) diarylamines can be obtained, for example:
  • R alkyl, preferably C 1 -C 22 , particularly preferably t-butyl or neopentyl.
  • the starting material for compounds in which Ar 3 is a biphenyl group can, for example, be the commercially available (from HW Sands, Jupiter, Fl., USA) N, N'-diphenyl-N, N'-di-m-tolylbenzidine.
  • the invention therefore also relates to a process for producing an electroluminescent material, characterized in that a) an organophosphorus compound of the formula (III)
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 are the same or different and / or
  • polynuclear optionally linked via one or more, preferably a bridge, and / or condensed aryl and / or
  • Heteroaryl groups preferably with 4 to 400, particularly preferably 4 up to 100, very particularly preferably 4 to 20 carbon atoms, which can optionally be substituted, where Ar 1 , Ar 3 , Ar 5 and Ar 6 each have two bonds and Ar 2 and Ar 4 each have a bond;
  • R 1 is a carbon hydrogen residue with 1 to 22 carbon atoms
  • Ar 7 may optionally be substituted, preferably with F, and may also contain heteroatoms, preferably 0 or Ar 7 , where Ar 7 has the same meanings as Ar 1 -6 independently of Ar 1 -6 ;
  • n 0, 1 or 2, preferably 0 or 1, particularly preferably 0. and b) the polymer thus obtained, containing structural units of the formula (I), is applied in the form of a film to a substrate which may also contain further layers.
  • the invention further relates to an electroluminescent device with one or more active layers, at least one of these active layers containing one or more polymers according to the invention.
  • the active layer can be, for example, a light-emitting layer and / or a
  • Transport layer and / or a charge injection layer Transport layer and / or a charge injection layer.
  • Electroluminescent devices containing polymers are described, for example, in
  • Electrodes usually contain an electroluminescent layer between a cathode and an anode, at least one of the electrodes being transparent.
  • electroluminescent layer between a cathode and an anode, at least one of the electrodes being transparent.
  • Electron transport layers can be introduced and / or between the electroluminescent layer and the anode one or more
  • Hole injection and / or hole transport layers can be introduced.
  • Metals or metallic alloys e.g. Ca, Mg, Al, In, Mg / Ag serve.
  • ITO indium oxide / tin oxide
  • Substrate e.g. made of glass or a transparent polymer.
  • the cathode is set to a negative potential with respect to the anode. Electrons are transferred from the cathode to the
  • Electron injection layer Electron transport layer or injected directly into the light emitting layer. At the same time, holes are drilled from the anode into the hole injection layer / hole transport layer or directly into the
  • the color of the emitted light can be varied by the materials used as the light-emitting layer.
  • Electroluminescent devices are used e.g. as self-illuminating display elements, such as indicator lights, alphanumeric displays,
  • Tg glass transition temperature
  • VPO Vapor Pressure Osmometry (see e.g. Cherdron, Kern, Braun, Internship in Macromolecular Chemistry)
  • UV / VIS UV / VIS spectroscopy
  • Phosphoryl chloride and DMF are mixed with the exclusion of moisture and ice cooling, and the triphenylamine is added in portions after 20 minutes.
  • the mixture is then stirred at 80 ° C. for eight hours, poured onto 300 g of crushed ice, allowed to come to room temperature and extracted with chloroform. After the solvent has been stripped off, the dark green oil is taken up in toluene and filtered through a glass filter frit charged with neutral aluminum oxide. The clear, yellow solution is evaporated to dryness and recrystallized from petroleum ether / toluene. Yellow crystals are obtained in 71% yield. Melting point 142 ° C.
  • Magnetic stirrer and distillation bridge heated to 130 ° C, with ethyl bromide being distilled off.
  • the mixture is heated to 1 90 ° C. within 1 hour and stirred at this temperature for a further 3 hours. Remaining for removal
  • Triethyl phosphite is applied at this temperature for a further 30 minutes. After cooling, the residue solidifies to a waxy mass, which is recrystallized from petroleum ether. You get fine white crystals,
  • a solution of the polymer from Example 4 in chlorobenzene (20 mg / ml) is applied under nitrogen by spin coating at 1000 rpm to a glass support (structured, structured, 2 mm wide) coated with ITO (indium tin oxide).
  • the glass support is placed over a lock while maintaining the
  • the diphenylaminobenzaldehyde and the bisphosphonate are placed under protective gas in 1,50 ml of toluene. While stirring, the potassium tert-butoxide is added in one portion at the boiling point, the mixture foaming strongly. The mixture is stirred for a further two hours at 80 ° C. and then hydrolyzed with 200 ml of a 10% acetic acid solution. The mixture is stirred vigorously and then transferred to a separatory funnel. The organic phase is shaken out several times with water and then dried over anhydrous sodium sulfate. It is strongly concentrated and the crude product is purified by column chromatography (neutral aluminum oxide, eluent toluene). After stripping off the solvent and drying, bright orange crystals are obtained in 82% yield.
  • column chromatography neutral aluminum oxide, eluent toluene
  • a solution of the polymer from Example 8 in chlorobenzene (20 mg / ml) is applied under nitrogen by spin coating at 1000 rpm to a glass support (structured, structured, strip 2 mm wide) coated with ITO (indium tin oxide).
  • the glass support is placed over a lock while maintaining the
  • Boiling heat then add another 200 ml of toluene and filter the hot solution from the slimy sediment. The filtrate is evaporated to dryness, in
  • Example 11 An electroluminescent device with the polymer from Example 11 was produced analogously to Example 5. Threshold voltage: 2.8 V; Max. Efficient: 0.20% at 5.2 V and 7 mA, a light intensity of 100 Cd / m 2 was found.
  • Phosphoryl chloride and DMF are mixed with the exclusion of moisture and ice cooling, and after 20 minutes the fluorotriphenylamine is added. The mixture is then stirred at 80 ° C. for eight hours, poured onto 300 g of crushed ice, allowed to come to room temperature and extracted with chloroform. After the solvent has been stripped off, the dirty brown solid is taken up in toluene and filtered through a glass filter frit charged with neutral aluminum oxide. The clear and yellow solution is evaporated to dryness and recrystallized from petroleum ether / toluene. Yellow crystals are obtained in 51% yield. Melting point: 204-205 ° C.
  • the diphosphonate and the dialdehyde are dissolved under protective gas in 30 ml of toluene at the boiling point and mixed with the potassium tert-butoxide in solid form.
  • the reaction mixture foams violently and suddenly becomes viscous.
  • toluene is carefully metered in so that the mixture remains stirrable.
  • the solvent is removed under reduced pressure, taken up in chloroform with heating and precipitated in isopropanol. After suction, the mixture is extracted with methanol for five hours. The polymer is obtained in yellow, stringy fibers in 78% yield.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Luminescent Compositions (AREA)

Abstract

L'invention concerne un matériau électroluminescent contenant au moins un polymère qui renferme des unités structurales de la formule (I) où les symboles et les indices ont la notation suivante: Ar?1, Ar2, Ar3, Ar4, Ar5, Ar6¿ sont identiques ou différents et représentent des groupes aryle et/ou hétéroaryle mononucléaires et/ou polynucléaires, éventuellement réticulés par au moins un pont, et/ou condensés. Ces groupes peuvent éventuellement être substitués, Ar?1, Ar3, Ar5 et Ar6¿ étant reliés à la chaîne par respectivement deux liaisons, et Ar?2 et Ar4¿ par respectivement une liaison. R1 représente H, un reste hydrocarbure contenant 1 à 22 atomes de carbone pouvant éventuellement être substitué, de préférence par F, et contenant également des hétéroatomes, de préférence O, ou bien A7, A7 ayant la même notation que Ar1-6 indépendamment de Ar1-6; n vaut 0, 1 ou 2. Le matériau électroluminescent de l'invention se distingue notamment par une faible tension initiale de l'électroluminescence et une efficacité élevée bien qu'il s'agisse de polymères non conjugués.
EP96930152A 1995-09-04 1996-09-03 Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents Withdrawn EP0848739A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE1995132574 DE19532574A1 (de) 1995-09-04 1995-09-04 Polymere mit Triarylamin-Einheiten als Elektrolumineszenzmaterialien
DE19532574 1995-09-04
DE1995135938 DE19535938A1 (de) 1995-09-27 1995-09-27 Polymere mit Triarylamin-Einheiten als Elektrolumineszenzmaterialien
DE19535938 1995-09-27
PCT/EP1996/003852 WO1997009394A1 (fr) 1995-09-04 1996-09-03 Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents

Publications (1)

Publication Number Publication Date
EP0848739A1 true EP0848739A1 (fr) 1998-06-24

Family

ID=26018274

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96930152A Withdrawn EP0848739A1 (fr) 1995-09-04 1996-09-03 Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents

Country Status (6)

Country Link
US (1) US5814244A (fr)
EP (1) EP0848739A1 (fr)
JP (1) JP2002515078A (fr)
KR (1) KR100421569B1 (fr)
CN (1) CN1125865C (fr)
WO (1) WO1997009394A1 (fr)

Families Citing this family (88)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0812820B1 (fr) * 1995-03-01 2001-01-17 Takasago International Corporation Derives de triphenylamine, et materiau conducteur de charge et photorecepteur electrophotographique prepares a partir desdits derives
WO1997005184A1 (fr) * 1995-07-28 1997-02-13 The Dow Chemical Company Fluorenes a substitution 2,7-aryle en position 9, oligomeres et polymeres de fluorenes substitues en position 9
US5929194A (en) * 1996-02-23 1999-07-27 The Dow Chemical Company Crosslinkable or chain extendable polyarylpolyamines and films thereof
AU2277697A (en) * 1996-02-23 1997-09-22 Dow Chemical Company, The Cross-linkable or chain extendable polyarylpolyamines and films thereof
US5728801A (en) * 1996-08-13 1998-03-17 The Dow Chemical Company Poly (arylamines) and films thereof
US5948552A (en) * 1996-08-27 1999-09-07 Hewlett-Packard Company Heat-resistant organic electroluminescent device
US6309763B1 (en) 1997-05-21 2001-10-30 The Dow Chemical Company Fluorene-containing polymers and electroluminescent devices therefrom
KR100697861B1 (ko) * 1998-03-13 2007-03-22 캠브리지 디스플레이 테크놀로지 리미티드 전장 발광 디바이스들
GB9805476D0 (en) * 1998-03-13 1998-05-13 Cambridge Display Tech Ltd Electroluminescent devices
EP2267815A1 (fr) * 1999-03-12 2010-12-29 Sumitomo Chemical Company, Limited Polymères, leur préparation et leurs utilisations
US6414104B1 (en) 1999-07-20 2002-07-02 Sri International Arylamine-substituted poly (arylene vinylenes) and associated methods of preparation and use
US6555959B1 (en) * 1999-09-30 2003-04-29 Fuji Photo Film Co., Ltd. Material for light emitting device, light emitting device using thereof, and amine compound
EP1195422B1 (fr) * 1999-12-20 2011-07-27 Panasonic Corporation Dispositif el a couche mince
US6512082B2 (en) 2000-01-05 2003-01-28 Cambridge Display Technology Ltd. Polymers, their preparation and uses
CN1205247C (zh) * 2000-01-05 2005-06-08 剑桥显示技术有限公司 聚合物,及其制备和应用
US6329086B1 (en) * 2000-06-13 2001-12-11 Eastman Kodak Company Electroluminescent devices having arylamine polymers
DE60138790D1 (de) * 2000-09-25 2009-07-09 Konica Corp Organisches Elektrolumineszenzelement und dafür verwendetes organisches Elektrolumineszenzmaterial
CN100390133C (zh) * 2000-10-05 2008-05-28 新日铁化学株式会社 有机场致发光元件
US7125930B2 (en) * 2001-04-27 2006-10-24 Sumitomo Chemical Company, Limited Block copolymer and polymeric luminescent element
TW541855B (en) * 2001-04-27 2003-07-11 Sumitomo Chemical Co Polymeric fluorescent substance and polymer light-emitting device using the same
US7074885B2 (en) 2001-05-03 2006-07-11 E.I. Du Pont De Nemours And Company Electroactive fluorene copolymers and devices made with such polymers
US7074886B2 (en) * 2001-05-07 2006-07-11 E. I. Du Pont De Memours And Company Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers
US6723828B2 (en) * 2001-05-23 2004-04-20 Sri International Conjugated electroluminescent polymers and associated methods of preparation and use
TW588105B (en) * 2001-07-19 2004-05-21 Sumitomo Chemical Co Polymeric fluorescent substance and polymer light-emitting device using the same
SG94878A1 (en) * 2001-07-30 2003-03-18 Sumitomo Chemical Co Polymeric fluorescent substance and polymer light-emitting device using the same
TWI249542B (en) * 2001-11-09 2006-02-21 Sumitomo Chemical Co Polymer compound and polymer light-emitting device using the same
AU2002367422A1 (en) * 2001-12-28 2003-07-24 Sumitomo Chemical Company, Limited Process for production of high-molecular compounds
GB0204989D0 (en) * 2002-03-04 2002-04-17 Opsys Ltd Phosphorescent compositions and organic light emitting devices containing them
SG128438A1 (en) 2002-03-15 2007-01-30 Sumitomo Chemical Co Polymer compound and polymer light emitting deviceusing the same
TWI280973B (en) 2002-08-28 2007-05-11 Sumitomo Chemical Co Polymer compound and polymer light-emitting device using the same
JP5299017B2 (ja) * 2002-10-24 2013-09-25 住友化学株式会社 高分子化合物およびそれを用いた高分子発光素子
DE10249723A1 (de) * 2002-10-25 2004-05-06 Covion Organic Semiconductors Gmbh Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung
EP2325224A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
US6916902B2 (en) * 2002-12-19 2005-07-12 Dow Global Technologies Inc. Tricyclic arylamine containing polymers and electronic devices therefrom
EP1443093A1 (fr) * 2003-01-29 2004-08-04 Samsung SDI Co., Ltd. Composés moléculaires chimiques capable d'émettre de la photoluminescence comprenant des structures électroniques déplaçables et leur utilisation dans des dispositifs d'affichage photoluminescents effaçables
US7402343B2 (en) * 2003-01-29 2008-07-22 Samsung Sdi Co., Ltd. Molecular chemical compounds with structures allowing electron displacement and capable of emitting photoluminescent radiation, and photoluminescence quenching device employing the same
US20040185302A1 (en) * 2003-02-12 2004-09-23 Uckert Frank P. Aromatic polymers with multiple side chains and methods for use thereof
US7049392B2 (en) * 2003-02-12 2006-05-23 E. I. Du Pont De Nemour And Company Electroluminescent copolymers with multi-functional monomers and methods for use thereof
US7138483B2 (en) * 2003-02-12 2006-11-21 E.I. Du Pont De Nemours And Company Monomers, conjugated polymers and electronic devices using such polymers
US7166689B2 (en) 2003-02-13 2007-01-23 Ricoh Company, Ltd. Aryl amine polymer, thin film transistor using the aryl amine polymer, and method of manufacturing the thin film transistor
WO2004106409A1 (fr) * 2003-05-30 2004-12-09 Covion Organic Semiconductors Gmbh Polymere
JP5062945B2 (ja) * 2003-06-27 2012-10-31 株式会社リコー 重合体
JP5230942B2 (ja) * 2003-12-13 2013-07-10 メルク パテント ゲーエムベーハー オリゴマーおよびポリマー
JP5092199B2 (ja) * 2004-02-02 2012-12-05 住友化学株式会社 有機エレクトロルミネッセンス素子
CN1320011C (zh) * 2004-09-09 2007-06-06 复旦大学 发光波段可调的三嵌段共聚聚合物电致发光材料
CN101061156A (zh) 2004-12-03 2007-10-24 住友化学株式会社 含三芳基胺的聚合物及电子器件
JP4546904B2 (ja) * 2005-02-25 2010-09-22 株式会社リコー 新規なアリールアミン重合体
JP2006243626A (ja) * 2005-03-07 2006-09-14 Ricoh Co Ltd 光波長変換素子
US7718760B2 (en) 2005-03-10 2010-05-18 Ricoh Company, Ltd. π-Conjugated polymer and manufacturing method thereof
JP2006253489A (ja) * 2005-03-11 2006-09-21 Ricoh Co Ltd 光起電力素子及びこれを用いた光センサー
JP4567495B2 (ja) * 2005-03-11 2010-10-20 株式会社リコー 光波長変換素子
JP2006253496A (ja) * 2005-03-11 2006-09-21 Ricoh Co Ltd 光起電力素子
JP5025914B2 (ja) * 2005-05-31 2012-09-12 株式会社リコー 色素増感太陽電池とその製造方法
DE112006002147T5 (de) 2005-08-12 2008-10-23 Sumitomo Chemical Co., Ltd. Polymerverbindung und polymere lichtemittierende Vorrichtung diese verwendend
JP2007077223A (ja) * 2005-09-13 2007-03-29 Ricoh Co Ltd ポリ（トリアリールアミン）
GB2445519B (en) 2005-10-07 2010-11-24 Sumitomo Chemical Co Copolymer and polymer light emitting device using the same
US20100157202A1 (en) 2005-11-11 2010-06-24 Sumitomo Chemical Company, Limited Conjugated polymer compound and polymer light emitting device using the same
CN101360773B (zh) 2005-11-18 2012-01-04 住友化学株式会社 高分子化合物及用其形成的高分子发光元件
DE102005060473A1 (de) * 2005-12-17 2007-06-28 Merck Patent Gmbh Konjugierte Polymere, deren Darstellung und Verwendung
GB2448098B (en) 2005-12-28 2011-07-06 Sumitomo Chemical Co Block copolymer
JP5387935B2 (ja) 2006-03-09 2014-01-15 株式会社リコー π共役ポリマー
TW200818981A (en) 2006-08-30 2008-04-16 Sumitomo Chemical Co Organic electroluminescence device
EP2063473A4 (fr) 2006-09-14 2010-11-10 Sumitomo Chemical Co Dispositif electroluminescent organique
JP5374908B2 (ja) * 2007-04-27 2013-12-25 住友化学株式会社 ピレン系高分子化合物及びそれを用いてなる発光素子
JP5248910B2 (ja) 2007-05-30 2013-07-31 住友化学株式会社 有機エレクトロルミネッセンス素子および該素子を用いた表示装置
JP2009021104A (ja) 2007-07-12 2009-01-29 Sumitomo Chemical Co Ltd 有機発光素子の製造方法
KR20100075830A (ko) 2007-07-31 2010-07-05 스미또모 가가꾸 가부시키가이샤 화합물 및 그의 제조 방법, 및 그것을 이용한 잉크 조성물, 박막, 유기 트랜지스터 및 유기 전계발광 소자
KR101226296B1 (ko) 2007-09-13 2013-01-24 가부시키가이샤 리코 신규한 아릴아민 중합체, 이의 제조 방법, 잉크 조성물, 막, 전자 소자, 유기 박막 트랜지스터 및 디스플레이 장치
JP5217931B2 (ja) 2007-11-29 2013-06-19 住友化学株式会社 有機エレクトロルミネッセンス素子及びその製造方法
EP2234459B1 (fr) 2007-12-28 2018-01-31 Sumitomo Chemical Company, Limited Dispositif électroluminescent à polymère, son procédé de fabrication et dispositif d'affichage électroluminescent à polymère
EP2249411A4 (fr) 2008-03-07 2014-03-26 Sumitomo Chemical Co Structure en couches
CN102046598B (zh) * 2008-03-31 2015-02-04 科学与工业研究委员会 给体-受体芴支架:其方法和用途
US9318706B2 (en) 2008-07-30 2016-04-19 Sumitomo Chemical Company, Limited Laminated structure, method for producing same, and electronic element comprising same
JP5515542B2 (ja) 2008-10-06 2014-06-11 住友化学株式会社 含窒素複素環構造を含む高分子化合物
JP5439823B2 (ja) * 2009-01-19 2014-03-12 日産化学工業株式会社 カーボンナノチューブ分散・可溶化剤
JP5691177B2 (ja) 2009-01-29 2015-04-01 住友化学株式会社 高分子化合物及びそれを用いる発光素子
KR20120052356A (ko) 2009-07-31 2012-05-23 스미또모 가가꾸 가부시키가이샤 고분자 발광 소자
KR101704090B1 (ko) 2009-09-30 2017-02-07 스미또모 가가꾸 가부시키가이샤 적층 구조체, 중합체, 전계 발광 소자 및 광전 변환 소자
KR20120086319A (ko) * 2009-10-19 2012-08-02 이 아이 듀폰 디 네모아 앤드 캄파니 전자적 응용을 위한 트라이아릴아민 화합물
KR101746247B1 (ko) 2009-10-22 2017-06-12 스미또모 가가꾸 가부시키가이샤 유기 전계 발광 소자
JP5716670B2 (ja) * 2009-11-25 2015-05-13 日産化学工業株式会社 カーボンナノチューブ分散剤
JP2011146307A (ja) 2010-01-15 2011-07-28 Sumitomo Chemical Co Ltd 高分子発光素子
TWI504668B (zh) 2010-01-28 2015-10-21 住友化學股份有限公司 高分子化合物及使用該高分子化合物而構成之發光元件
WO2011132698A1 (fr) 2010-04-20 2011-10-27 住友化学株式会社 Élément électroluminescent organique
JP5866157B2 (ja) 2010-07-29 2016-02-17 住友化学株式会社 積層構造体、それを用いた電子デバイス、芳香族化合物及び該化合物の製造方法
CN103429370B (zh) 2011-03-17 2016-08-24 住友化学株式会社 金属复合体组合物及其混合物
CN103554953B (zh) * 2013-11-06 2016-01-20 山东轻工职业学院 一种用作涤纶织物染料的化合物
EP4063427A4 (fr) * 2020-01-13 2023-01-11 LG Chem, Ltd. Polymère et diode électroluminescente organique l'utilisant

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3995299A (en) * 1974-10-15 1976-11-30 The Secretary Of State For Industry In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Radiation sources
US4423203A (en) * 1982-08-20 1983-12-27 Eastman Kodak Company Electrically photosensitive polymers containing vinylene-1,4-phenylene-imino-1,4-phenylene-vinylenearylene groups
GB8909011D0 (en) * 1989-04-20 1989-06-07 Friend Richard H Electroluminescent devices
WO1993006189A1 (fr) * 1991-09-18 1993-04-01 Idemitsu Kosan Co., Ltd. Element electroluminescent organique
EP1056140B1 (fr) * 1992-08-28 2005-07-06 Idemitsu Kosan Company Limited Matériau auxiliaire pour l'injection de charges
JP3278252B2 (ja) * 1993-08-12 2002-04-30 靖彦 城田 有機ｅｌ素子
US5503910A (en) * 1994-03-29 1996-04-02 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
JPH0854746A (ja) * 1994-08-10 1996-02-27 Mitsubishi Chem Corp 電子写真用感光体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9709394A1 *

Also Published As

Publication number Publication date
KR19990044367A (ko) 1999-06-25
CN1199414A (zh) 1998-11-18
JP2002515078A (ja) 2002-05-21
WO1997009394A1 (fr) 1997-03-13
KR100421569B1 (ko) 2004-07-05
CN1125865C (zh) 2003-10-29
US5814244A (en) 1998-09-29

Similar Documents

Publication Publication Date Title
WO1997009394A1 (fr) Polymeres contenant des unites triarylamine s'utilisant comme materiaux electroluminescents
EP0783541B1 (fr) Polymeres renfermant de l'azote utilises comme materiaux electroluminescents
EP0793698B1 (fr) Polymeres conjugues contenant des hetero-spiro-atomes et leur utilisation sous forme de materiaux electroluminescents
EP0894107B1 (fr) Composes a spiro-atomes et leur utilisation comme materiaux electroluminescents
EP0882082B1 (fr) Polymeres partiellement conjugues a spirocentres et leur utilisation comme materiaux electroluminescents
EP0707020B1 (fr) Polymères conjugués spiranniques et leur utilisation comme matériaux électroluminescents
EP0699699B1 (fr) Dérivés de poly(4,5,9,10-tetrahydropyrène-2,7diyl) et leur utilisation comme matériaux électroluminiscents
EP1161478B1 (fr) Polymeres et copolymeres de triptycene
DE19748814A1 (de) Substituierte Poly(arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektrolumineszenz
EP0938514B1 (fr) Terpolymeres de poly(arylenevinylene) ordonnes, leur procede de preparation et leur utilisation comme materiaux electroluminescents
EP1123337A1 (fr) Polymeres conjugues contenant des unites 2,7-fluorenyle a proprietes ameliorees
DE19615128A1 (de) Konjugierte Polymere mit Hetero-Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien
DE69427909T2 (de) Polymere für optische vorrichtungen
DE4422670A1 (de) Konjugierte Polymere mit Ansateilstrukturen und ihre Verwendung als Elektrolumineszenzmaterialien
DE19532574A1 (de) Polymere mit Triarylamin-Einheiten als Elektrolumineszenzmaterialien
DE19505416A1 (de) Poly(paraphenylenvinylen)-Derivate und ihre Verwendung als Elektrolumineszenzmaterialien
DE19535938A1 (de) Polymere mit Triarylamin-Einheiten als Elektrolumineszenzmaterialien
DE4435047A1 (de) Poly(paraphenylenvinylen)-Derivate und ihre Verwendung als Elektrolumineszenzmaterialien

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19980406

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB NL

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: AVENTIS RESEARCH & TECHNOLOGIES GMBH & CO. KG

17Q First examination report despatched

Effective date: 19991210

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: AXIVA GMBH

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: CELANESE VENTURES GMBH

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: COVION ORGANIC SEMICONDUCTORS GMBH

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: MERCK PATENT GMBH

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20080401