EP0907971A1 - Diodenadressiertes farbdisplay mit molekularem phosphor - Google Patents
Diodenadressiertes farbdisplay mit molekularem phosphorInfo
- Publication number
- EP0907971A1 EP0907971A1 EP98903244A EP98903244A EP0907971A1 EP 0907971 A1 EP0907971 A1 EP 0907971A1 EP 98903244 A EP98903244 A EP 98903244A EP 98903244 A EP98903244 A EP 98903244A EP 0907971 A1 EP0907971 A1 EP 0907971A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- diode
- diketonate
- phosphor
- addressed
- color
- 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- Withdrawn
Links
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003222 pyridines Chemical class 0.000 claims abstract description 7
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 239000006104 solid solution Substances 0.000 claims description 4
- 230000008033 biological extinction Effects 0.000 abstract description 3
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 13
- 239000003446 ligand Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052693 Europium Inorganic materials 0.000 description 4
- -1 Europium ion Chemical class 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- BVQAWSJMUYMNQN-UHFFFAOYSA-N dipyridophenazine Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 BVQAWSJMUYMNQN-UHFFFAOYSA-N 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- XDUUQOQFSWSZSM-UHFFFAOYSA-N 5-chloro-1,10-phenanthroline Chemical compound C1=CC=C2C(Cl)=CC3=CC=CN=C3C2=N1 XDUUQOQFSWSZSM-UHFFFAOYSA-N 0.000 description 1
- UJAQYOZROIFQHO-UHFFFAOYSA-N 5-methyl-1,10-phenanthroline Chemical compound C1=CC=C2C(C)=CC3=CC=CN=C3C2=N1 UJAQYOZROIFQHO-UHFFFAOYSA-N 0.000 description 1
- PDDBTWXLNJNICS-UHFFFAOYSA-N 5-nitro-1,10-phenanthroline Chemical compound C1=CC=C2C([N+](=O)[O-])=CC3=CC=CN=C3C2=N1 PDDBTWXLNJNICS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002178 europium compounds Chemical class 0.000 description 1
- LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J29/00—Details of cathode-ray tubes or of electron-beam tubes of the types covered by group H01J31/00
- H01J29/02—Electrodes; Screens; Mounting, supporting, spacing or insulating thereof
- H01J29/10—Screens on or from which an image or pattern is formed, picked up, converted or stored
- H01J29/18—Luminescent screens
- H01J29/20—Luminescent screens characterised by the luminescent material
-
- 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
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
- H01L33/502—Wavelength conversion materials
Definitions
- Diode-addressed color display with molecular phosphor Diode-addressed color display with molecular phosphor.
- the invention relates to a diode-addressed color display with a UV diode and a phosphor for illuminated displays, lights, solid-state image amplifiers, screens and monitors and others.
- Color displays for illuminated displays, luminaires, solid-state image intensifiers, screens and monitors are intended to reproduce color images true to color.
- the entire color information of a colored image is represented by information about the three primary colors red, green and blue.
- Additive color mixing can be used to produce any color or white from the three primary colors.
- This principle is used both by the conventional color television set with a tube from Braunschweig and by the various flat screen technologies such as plasma screens, electroluminescent screens and LCD displays.
- a color display is characterized by a high intrinsic emission quantum yield and a ligand-centered absorption in the range between 350 and 400 nm with a high extinction coefficient. According to photophysical considerations, these two phosphor properties are actually mutually exclusive. Surprisingly, however, it has been found that phosphors of the composition [Eu (diketonate) a X bl X ' b2 ] both
- the phosphors according to the invention are molecular compounds and therefore generally readily soluble in polar organic solvents. Their properties can therefore be easily examined in solution and the test results can be transferred to the solid state. The solubility in organic solvents also allows new design concepts for diode-addressed color displays.
- These europium complexes are charged and can be bound to a polymer support such as Nafion ® . As a result, these phosphors are particularly stable and the photophysical properties are further improved.
- the diode-addressed color display comprises a transparent polymeric coating which contains the phosphorus of the composition [Eu (diketonate) a X bl X ' b2 ] in solid solution.
- the coating is transparent because the light is not scattered on the dissolved phosphor particles.
- a color display consists of the UV diode and a transparent coating applied to it, which contains the phosphorus.
- the transparent coating can contain, for example, the phosphorus in a solid solution in a transparent matrix made of polyacrylate, epoxy resin or another polymer.
- LEDs are usually cast in epoxy housings, with the cast-on lens made of epoxy resin serving to improve the coupling out of the light from the diode.
- the phosphor can be used as
- the phosphorus is mixed with the epoxy resin and forms a solid solution with it.
- Large, two-dimensional displays can be easily manufactured by combining a diode array with the phosphor according to the invention.
- the diode array can be covered by a glass plate which is printed with fluorescent triplets, each with a red, green and blue glowing dot.
- the red glowing dot contains [Eu (diketonate) a X bl X ' b2 ] as phosphorus.
- the UV diode is in particular a UV diode made of InGaN or GaN and has its emission maximum between 370 and 410 nm with a half width FWHM ⁇ 50 nm.
- These complex coordination compounds of europium (III) contain Eu 3 + as the metal center, anions of a diketonate (diketonate) as charged ligands and pyridine or a pyridine derivative or 2,2'-bipyridine or a 2,2'-bipyridyl derivative as neutral ligands.
- the 2,2'-bipyridyl derivatives also include 1, 10-phenathroline and its derivatives. These coordination compounds have strong optical intraligand transitions and, in addition to absorbing the chelate ligands, are also effective as light antennas.
- the primary excitation by UV radiation leads to a ligand-centered excited state, the energy of which is transferred to the Europium ion in a subsequent step and leads to light emission there.
- the original ones remain in these connections
- Absorption properties of the ligands are largely preserved and the interligand change effects are weak.
- the coordinative saturation of the europium prevents the tendency towards polymerization of the compounds, which are therefore mononuclear.
- molecular phosphors are therefore composed of host lattices doped with activator ions.
- coordination compounds of europium with charged, anionic chelate ligands (diketonate) of the composition [Eu (diketonate) 3 ] are used, which as a rule are saturated by two or three further aquo ligands with the coordination number 8 or 9 are.
- Simple ligand substitution under mild conditions allows the introduction of a large number of uncharged organic ligands X, X 'to the product [Eu (diketonate) 3 X, X'].
- (Diketonate) can, for example, be an anion of the diketonates acac, thd, ttfa, fod, tfnb, dbm
- X can be, for example, pyridine or a pyridine derivative or bipyridine or a bipyridine derivative.
- Bipyridine derivatives are in particular also those compounds which are derived from 1,10-phenanthroline, such as, for example, dpphen, mphen, dmphen, tmphen, NOphen, Clphen, dppz (see formula scheme).
- the monodentate or bidentate ligands are chosen so that the europium ion is coordinated eight times.
- the reaction products are each obtained as a microcrystalline precipitate.
- the materials are recrystallized from ethanol for cleaning. 1st embodiment
- Neutral chelate ligands bpy 2,2'-bipyridine phen 1, 10-phenanthroline dpphen 4,7-diphenyl-l, 10-phenanthroline mphen 5-methyl-1, 10-phenanthroline dmphen 4, 7-dimethyl-1, 10 -phenantholin tmphen 3,4,7, 8-tetramethyl 1- 1, 10-phenanthroline NOphen 5-nitro-1, 10-phenanthroline Clphen 5-chloro-1, 10-phenanthroline dppz Dipyridinphenazin
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19708407 | 1997-03-03 | ||
DE19708407 | 1997-03-03 | ||
DE19802046A DE19802046A1 (de) | 1997-03-03 | 1998-01-21 | Diodenadressiertes Farbdisplay mit molekularem Phosphor |
DE19802046 | 1998-01-21 | ||
PCT/IB1998/000259 WO1998039806A1 (de) | 1997-03-03 | 1998-03-02 | Diodenadressiertes farbdisplay mit molekularem phosphor |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0907971A1 true EP0907971A1 (de) | 1999-04-14 |
Family
ID=26034430
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98903244A Withdrawn EP0907971A1 (de) | 1997-03-03 | 1998-03-02 | Diodenadressiertes farbdisplay mit molekularem phosphor |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0907971A1 (de) |
JP (1) | JP2000511586A (de) |
WO (1) | WO1998039806A1 (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6051925A (en) * | 1997-03-03 | 2000-04-18 | U.S. Philips Corporation | Diode-addressed color display with molecular phosphor |
JP2002530826A (ja) * | 1998-11-26 | 2002-09-17 | コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ | 放電灯 |
JP2002275182A (ja) * | 2001-03-22 | 2002-09-25 | Nippon Kayaku Co Ltd | 赤色蛍光材料およびそれを含有する組成物 |
JP5327635B2 (ja) * | 2009-11-20 | 2013-10-30 | 国立大学法人神戸大学 | 膜状蛍光発光体およびその製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0826264B2 (ja) * | 1987-07-21 | 1996-03-13 | 三井東圧化学株式会社 | 発光性化合物を含有するインク組成物 |
US5006503A (en) * | 1990-03-13 | 1991-04-09 | Eastman Kodak Company | Thermally-transferable fluorescent europium complexes |
JPH05152609A (ja) * | 1991-11-25 | 1993-06-18 | Nichia Chem Ind Ltd | 発光ダイオード |
-
1998
- 1998-03-02 WO PCT/IB1998/000259 patent/WO1998039806A1/de not_active Application Discontinuation
- 1998-03-02 JP JP10529287A patent/JP2000511586A/ja not_active Abandoned
- 1998-03-02 EP EP98903244A patent/EP0907971A1/de not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO9839806A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2000511586A (ja) | 2000-09-05 |
WO1998039806A1 (de) | 1998-09-11 |
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Legal Events
Date | Code | Title | Description |
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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 |
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AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR GB |
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17P | Request for examination filed |
Effective date: 19990311 |
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RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: PHILIPS CORPORATE INTELLECTUAL PROPERTY GMBH Owner name: KONINKLIJKE PHILIPS ELECTRONICS N.V. |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: PHILIPS CORPORATE INTELLECTUAL PROPERTY GMBH Owner name: KONINKLIJKE PHILIPS ELECTRONICS N.V. |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH Owner name: KONINKLIJKE PHILIPS ELECTRONICS N.V. |
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STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
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18W | Application withdrawn |
Effective date: 20061113 |