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WO2002011209A2 - Procede de configuration de supports de changement de couleur pour dispositifs d'affichage a diode electroluminescente organique - Google Patents

Procede de configuration de supports de changement de couleur pour dispositifs d'affichage a diode electroluminescente organique Download PDF

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Publication number
WO2002011209A2
WO2002011209A2 PCT/US2001/024597 US0124597W WO0211209A2 WO 2002011209 A2 WO2002011209 A2 WO 2002011209A2 US 0124597 W US0124597 W US 0124597W WO 0211209 A2 WO0211209 A2 WO 0211209A2
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coumarin
layer
color changing
changing material
area
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PCT/US2001/024597
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WO2002011209A3 (fr
Inventor
Karl Pichler
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Emagin Corporation
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Priority to AU2001281103A priority Critical patent/AU2001281103A1/en
Publication of WO2002011209A2 publication Critical patent/WO2002011209A2/fr
Publication of WO2002011209A3 publication Critical patent/WO2002011209A3/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • Organic electroluminescent devices also known as organic light emitting diode (“OLED”) devices
  • OLED organic light emitting diode
  • One or more layers of semi-conducting organic material are sandwiched between two electrodes, an anode and a cathode.
  • An electric current is applied to the device, causing electrons to move into the organic material(s) from the cathode and positive charges, typically referred to as holes, to move into the organic material(s) from the anode.
  • the positive and negative charges recombine in the electroluminescent medium (i.e., the emitter layer) and produce photons.
  • the wavelength of the photons, and consequently the color of the emitted light depends on the electronic properties of the organic materials in which the photons are generated. The electronic properties of the organic materials are in turn dictated by their chemical structures.
  • the color of light emitted from an OLED device may be controlled by the selection of the organic materials in the emitter layer. Specifically, the precise color of emitted light can be controlled by the selection of host materials and dopants in the emitter layer. By changing the kinds of organic solids making up the emitter layer, many different colors of light may be generated, ranging from deep blue to red. In addition, color filters and color changing media may be used to alter the color of light emitted from the emitter layer of an OLED.
  • An OLED may be designed to be viewed either from the "top” (i.e., from the face distal to the substrate), which is referred to herein as “up-emitting,” or from the “bottom” (i.e., through the substrate), which is referred to herein as “down-emitting.” Whether an OLED is designed to emit light through the top or the bottom, the structure between the viewer and the light-emitting material should be sufficiently transparent to allow the emitted light to pass. In many applications, it is advantageous to employ an up-emitting OLED. This permits an OLED to be built on top of an opaque silicon driver chip, e.g., for active matrix addressing. OLED displays are typically composed of a two-dimensional matrix of pixels, each of which comprises an OLED.
  • Such displays generally include an addressing circuit for activating the matrix of pixels in either an active or a passive manner.
  • a typical passive matrix-addressed OLED display numerous OLEDs are formed on a single substrate and arranged in groups in a regular grid pattern. Several OLED groups forming a column of the grid may share a common cathode, or cathode line. Several OLED groups forming a row of the grid may share a common anode, or anode line. The individual OLEDs in a given group emit light when their cathode line and anode line are activated at the same time.
  • the row and column structure is build into the substrate using standard semi- conductor fabrication techniques. In this case, the substrate has an array of discrete electrodes, each one corresponding to a point in the matrix.
  • OLED displays are emerging as a viable design choice for use in small products, especially small portable electronic devices, such as head-mounted displays, pagers, cellular and portable telephones, two-way radios, data banks, etc.
  • OLED arrays are capable of generating sufficient light for use in displays under a variety of ambient light conditions (from little or no ambient light to bright ambient light).
  • OLEDs can be fabricated relatively cheaply and in a variety of sizes from very small (less than a tenth millimeter in diameter) suitable for microdisplay devices to relatively large (greater than an inch) so that OLED arrays can be fabricated in a variety of sizes.
  • OLEDs have the added advantages that their emissive operation provides a very wide viewing angle.
  • OLEDs have a low activation voltage (about 5 volts), a fast response when the emitter layer is thin, and high brightness in proportion to the injected electric current.
  • An OLED display may be monochromatic, that is, each pixel comprising the display emits light of the same color.
  • various pixels of an OLED display may emit different colors.
  • a full-color OLED display is formed from an array of pixels comprising a red, a green and a blue sub-pixel. The sub-pixels in any particular pixel can be activated in various combinations to generate an entire spectrum of colors.
  • a second approach for making full-color OLED displays employs OLEDs that emit white light combined with color filters that are precisely aligned over each OLED. Certain wavelengths of light are filtered out by the filters, with the result that the various color filters generate red, green and blue light for the sub-pixels.
  • the use of color filters can be inefficient, however, because the filters inevitably absorb some light.
  • a third approach for making full-color OLED displays is to use a monochromatic OLED array with color changing materials (instead of color filters) aligned on top of the pixels.
  • Color changing materials work by absorbing light of higher wavelength (e.g. , blue light) and then emitting light of lower wavelength by fluorescence or phosphorescence (photoluminescence) (e.g., red or green light).
  • fluorescence or phosphorescence photoluminescence
  • the use of color changing materials is known in the art (see e.g., C. Hosokawa et al. (1997) J. SID 5(4):331; U.S. Patent No. 5,126,214 assigned to Idemitsu Kosan Co., Ltd.; and U.S. Patent No. 5,294,870 assigned to Eastman Kodak Co.).
  • etching requires relatively thick color changing material layers, which results in a display having coarse resolution.
  • a photolithography process may not be compatible with the highly photoluminescent organic color changing materials or with photo-resist solution, developer, etch solution or plasma. Even if standard photolithography is possible, it requires a large number of steps and is thus quite costly. There is clearly a need for a method of patterning color changing material layers for high-resolution, full-color OLED display devices.
  • the present invention relates methods for fabricating color OLED display devices.
  • the present invention relates to methods for fabricating full-color OLED display devices, which are those devices having red, green and blue sub-pixels that can be activated in any combination to produce any color in the visible light spectrum.
  • the present invention relates to methods for patterning thin fluorescent color changing material ("CCM”) layers using photo-oxidation in the presence of oxygen and a photomask.
  • the oxygen is ambient oxygen.
  • the patterning occurs without the physical removal of color changing materials from the layers.
  • the present invention further provides a protective layer between subsequent color changing material layers in order to prevent the photo-oxidation patterning of underlying layers during patterning of the topmost layer. Photo-oxidation patterning leaves the fluorescence of the materials in the protected parts of the layer intact while making the photo-oxidized parts non-fluorescent or with very low fluorescence.
  • the present invention allows for the patterning of layers directly on OLEDs without destroying the underlying layers.
  • the resulting displays can have very high resolution, i.e., small pixel size.
  • the methods of the present invention are simple and economical. Furthermore, the methods can be used to fabricate color OLED display devices using a wide variety of standard materials and standard mask-aligners and photo-exposure equipment. In some embodiments, the methods of the present invention utilize a one- step exposure of the color changing material layers to ultraviolet light. hi a particularly preferred embodiment, the present invention can be used to fabricate high-resolution, full-color OLED display devices having pixels comprising red, green and blue sub-pixels. More preferably, the devices have very small pixel sizes and high quantum efficiency of photoluminescence (and therefore, high brightness) and may be down-emitting or up-emitting displays.
  • the methods of the present invention allow for patterning of color changing materials without removal of any of the material in the layers. As a result, very thin color changmg material layers can be used, which prevents loss of light and contrast. In addition, the methods of the present invention allow for the preservation of the flatness of the patterned layers so that high-resolution color OLED displays can be fabricated.
  • the present invention relates to a method for patterning a first layer comprising a first color changing material, the method comprising: (a) exposing at least one area of the first layer to light and oxygen and leaving at least one area unexposed; and (b) covering the at least one unexposed area with a protective layer, wherein the first color changing material in the at least one exposed area becomes substantially transparent to visible light and substantially non- photoluminescent after the exposing step.
  • the method further comprises the steps of: (c) forming a second layer comprising a second color changing material over the first layer; and (d) exposing at least one area of the second layer to light and oxygen and leaving at least one area unexposed, wherein the second color changing material in the at least one exposed area becomes substantially transparent to visible light and substantially non-photo luminescent after the exposing step, and wherein the two unexposed areas are not aligned.
  • the present invention relates to a method for patterning a layer comprising a color changing material, the method comprising: (a) aligning a photomask over the layer, the photomask comprising a first area that is transparent to light and a second area that absorbs light; (b) shining light through the photomask onto the layer in the presence of oxygen and leaving at least one area unexposed; and (c) covering the at least one unexposed area with a protective layer, wherein the area of the layer under the first area of the photomask is exposed to light and oxygen, wherein the area of the layer under the second area of the photomask is not exposed to light and oxygen, wherein the color changing material in the exposed area becomes substantially transparent to visible light and substantially non-photoluminescent after the exposing step, and wherein the color changing material in the unexposed area is substantially non-transparent to visible light and substantially photoluminescent after the exposing step.
  • the present invention relates to a method of fabricating an up-emitting full-color OLED display device comprising the steps of: (a) providing a monochromatic OLED display device having a plurality of bottom electrode elements and a surface through which light is emitted; (b)depositing a first layer comprising a first color changing material on at least a portion of the surface; (c) aligning at least one light absorbing area of a photomask above the first layer with a first electrode element of the monochromatic OLED display device; (d) exposing at least one unmasked area of the first layer to light shone through the photomask in the presence of oxygen to leave a first color changing region in a first patterned layer aligned with the first electrode element; (e) depositing a first protective layer over the first patterned layer; (f) depositing a second layer comprising a second color changing material on the first protective layer; (g) aligning at least one light absorbing area of a photomask above the second layer with
  • Figure 2 shows an up-emitting full color OLED display device.
  • Figure 3 shows a down-emitting full color OLED display device.
  • Figure 4 shows a first step in a method according to the present invention.
  • Figure 5 shows a second step in a method according to the present invention.
  • Figure 6 shows a third step in a method according to the present invention.
  • Figure 7 shows a fourth step in a method according to the present invention.
  • Figure 8 shows a fifth step in a method according to the present invention.
  • Figure 9 shows a full-color OLED display device made by a method according to the present invention.
  • Figure 10 shows another embodiment of a full-color OLED display device made by a method according to the present invention.
  • Figure 11 shows one configuration of an OLED display device comprising color changing material layers and made by a method according to the present invention.
  • Figure 12 shows another configuration of an OLED display device comprising color changing material layers and made by a method according to the present invention.
  • Figure 13 shows another configuration of an OLED display device comprising color changing material layers and made by a method according to the present invention.
  • Figure 14 shows yet another configuration of an OLED display device comprising color changing material layers and made by a method according to the present invention.
  • Figure 15 shows a first step in a method of the present invention.
  • Figure 16 shows a second step in a method of the present invention.
  • Figure 17 shows a third step in a method of the present invention.
  • Figure 18 shows a final step in a method of the present invention.
  • Bottom electrode means an electrode that is deposited directly onto the substrate.
  • Top electrode means an electrode that is deposited at the end of the OLED that is distal to the substrate.
  • Hole-injection layer is a layer into which holes are injected from an anode when a voltage is applied across an OLED.
  • Hole-transport layer is a layer having high hole mobility and high affinity for holes that is between the anode and the emitter layer. It will be evident to those of sldll in the art that the hole-injection layer and the hole- transport layer can be a single layer (“hole-injection/hole-transport layer”), or they can be distinct layers comprising different chemical compounds.
  • Electrode is a layer into which electrons are injected from a cathode when a voltage is applied across an OLED.
  • Electron-transport layer is a layer having high electron mobility and high affinity for electrons that is between the cathode and the emitter layer. It will be evident to those of skill in the art that the electron-injection layer and the electron-transport layer can be a single layer (“electron-injection/electron- transport layer”), or they can be distinct layers comprising different chemical compounds.
  • Down-emitting refers to an OLED in which light is transmitted through the transparent or semi-transparent bottom electrode, which is typically an anode.
  • Up-emitting refers to an OLED in which light is transmitted through the transparent or semi-transparent top electrode, which is typically a cathode.
  • High energy (i.e., blue) light in full-color OLED display devices may be produced by any source, but is preferably produced by an emissive monochromatic OLED display device, such as the one shown in Figure 1 and described below.
  • the monochromatic OLED display device may or may not be pixelated.
  • the OLED display is pixelated and is of high resolution, for example, with sub-pixel sizes less than about 50 ⁇ m, preferably less than about 25 ⁇ m, more preferably less than about 10 ⁇ m.
  • the device of Figure 1 comprises a substrate 101, which can be transparent or opaque (and which may further comprise driving electronics), a patterned bottom electrode 102, which is a cathode or an anode, a first charge transport layer 103, which is a hole-transport layer if the bottom electrode is an anode and which is an electron-transport layer if the bottom electrode is a cathode, an emitter layer 104, a second transport layer 105, which is a hole-transport layer if the bottom electrode is a cathode and which is an electron-transport layer if the bottom electrode is an anode, a top electrode 106, which is a cathode if the bottom electrode is an anode and which is an anode if the bottom electrode is a cathode, and which may be patterned (i.e., in passive matrix displays) and a protective layer 107.
  • a substrate 101 which can be transparent or opaque (and which may further comprise driving electronics)
  • a patterned bottom electrode 102 which is
  • Each element of the patterned bottom electrode 102 represents one pixel in the matrix.
  • holes are transported through the hole-transport layer 103 or 105 and electrons are transported through the electron- transport layer 105 or 103 and holes and electrons recombine in the light emitting layer 104 to produce light of the same wavelength 108, e.g., blue light, at each pixel.
  • Patterning means that the materials are formed into stripes, squares, rectangles, triangles, hexagons, circles, or any other shape known in the art.
  • each individual OLED is rectangular and the color changing materials are patterned in parallel stripes, or rectangular dots. The patterning of color changing materials provides for the formation of discrete red, green and blue sub-pixels, without having the colors mix together.
  • Electrodes can be patterned by any method known in the art, including, but not limited to lithographic, particularly photolithographic techniques, laser ablation, and masking during deposition.
  • a full-color OLED display device is shown in Figure 2, and comprises the elements of a monochromatic display device, including a substrate 101, which can be transparent or opaque (and which may further comprise driving electronics), a patterned bottom electrode 102, which is a cathode or an anode, a first charge transport layer 103, which is a hole-transport layer if the bottom electrode is an anode and which is an electron-transport layer if the bottom electrode is a cathode, an emitter layer 104, a second charge transport layer 105, which is a hole-transport layer if the bottom electrode is a cathode and which is an electron-transport layer if the bottom electrode is an anode, a top electrode 106, which is a cathode if the bottom electrode is an anode and which is an anode if the bottom electrode is a cathode, and a first protective layer 107 covering the cathode 106.
  • a substrate 101 which can be transparent or opaque (and which may further comprise driving
  • the full-color OLED display device further comprises a first color changing layer 209 comprising a first patterned color changing material 210, a second protective layer 207 covering the first color changing layer 209, a second color changing layer 211 comprising a second patterned color changing material 212 adjacent to the second protective layer 207, and an encapsulation layer 207 covering the second color changing layer 211.
  • the matrix of pixels 215, each comprising a red, a green and a blue sub-pixel, in a full-color OLED display device shown in Figure 2 may be formed as follows. Each element of the patterned electrode 102 represents one sub-pixel in the matrix.
  • a first patterned color changing material 210 is aligned with a first element of the patterned bottom electrode 102 so that the first patterned color changing material is directly above a specified element 102.
  • the second patterned color changing material 212 is aligned with a second element of the patterned bottom electrode 102 adj cent to the first element.
  • a third element of the patterned bottom electrode 102 adjacent to the second element is not aligned with a patterned color changing material.
  • the emitter layer 104 When a current is applied between the top electrode 106 and the patterned bottom electrode 102, holes are transported through the hole-transport layer 103 or 105 and electrons are transported through the electron-transport layer 105 or 103 and holes and electrons recombine in the emitter layer 104 to produce light of a particular wavelength 208, e.g., blue light, at each sub-pixel.
  • a particular wavelength 208 e.g., blue light
  • red sub-pixel when blue light is emitted from the emitter layer 104 at the second element of the patterned bottom electrode 102, it is absorbed by the second patterned color changing material 212 ("blue-to-red CCM") that is aligned with the second element.
  • the second patterned color changing material 212 then emits red light 214 by fluorescence or phosphorescence.
  • blue sub-pixel when blue light is emitted by the emitter layer 104 at the third element of the patterned bottom electrode 102, the blue light 208 is transmitted through the various layers 207, 209 and 211 substantially without being absorbed.
  • the patterning of the first and second color changing materials are repeated every fourth element, resulting in an array of pixels 215 each comprising a red, a green and a blue sub-pixel.
  • An embodiment of a down-emitting full-color OLED display device shown in Figure 3, comprises a first color changing layer 309 comprising a first patterned color changing material 310 deposited on a substrate 301, a first protective layer 307 covering the first color changing layer 309 formed on a transparent or semi- transparent substrate 301.
  • a second color changing layer 311 comprises a second patterned color changing material 312 adjacent to the first protective layer 307, a second protective layer 307 covering the second color changing layer 311, a patterned bottom electrode 302, which is a cathode or an anode, a first charge transport layer 303, which is a hole-transport layer if the bottom electrode is an anode and which is an electron-transport layer if the bottom electrode is a cathode, an emitter layer 304, a second charge transport layer 305, which is a hole-transport layer if the bottom electrode is a cathode and which is an electron-transport layer if the bottom electrode is an anode, a top electrode 306, which is a cathode if the bottom electrode is an anode and which is an anode if the bottom electrode is a cathode, and an encapsulation layer 307.
  • blue light 308 is emitted downward from the emitter layer 304 at the first element of the patterned bottom electrode 302, and is absorbed by the first patterned color changing material 310 ("blue-to-red CCM") that is aligned with the first element.
  • the first patterned color changing material 310 then emits red light 313 by fluorescence or phosphorescence.
  • blue light is emitted from the emitter layer 304 at the second element of the patterned bottom electrode 302, it is absorbed by the second patterned color changing material 312 (“blue-to-green CCM”) that is aligned with the second element.
  • the second patterned color changing material 312 then emits green light
  • OLEDs can be fabricated by any method known in the art.
  • the OLED layers may be formed by evaporation, spin casting, self-assembly or other appropriate film- forming techniques. Thicknesses of the layers typically range from a few monolayers to about 2,000 Angstroms.
  • OLEDs are formed by vapor deposition of each layer. In a preferred embodiment, OLEDs are formed by thermal vacuum vapor deposition.
  • an OLED may comprise a hole-injection layer adjacent to the anode and at least two hole-transport layers, a first hole-transport layer adjacent to the hole-injection layer and a second hole-transport layer adjacent to the first hole- transport layer.
  • the hole-injection layer and the at least two hole-transport layers may be deposited separately. Alternately, at least two of the layers may be inter-deposited.
  • An OLED may comprise an electron-injection layer and at least one electron- transport layer, or the OLED can further comprise an additional layer adjacent to the top electrode.
  • the layer comprises indium tin oxide.
  • Other OLED structures will be evident to those skilled in the art.
  • a substrate may be made from any material known in the art, including glass, silicon, plastic, quartz and sapphire. If the OLED display is formed on a silicon chip, the chip preferably includes drive electronics and one of the sub-pixel electrodes. The top electrode may be common to all sub-pixels.
  • An anode is typically about 800 A thick and can have one layer comprising a metal having a high work function, a metal oxide and mixtures thereof.
  • the anode comprises a material selected from the group consisting of a conducting or semiconducting metal oxide or mixed metal oxide such as indium zinc tin oxide, indium zinc oxide, ruthenium dioxide, molybdenum oxide, nickel oxide or indium tin oxide, a metal having a high work function, such as gold or platinum, and a mixture of a metal oxide and a metal having a high work function.
  • the anode further comprises a thin layer (approximately 5-15 A thick) of dielectric material between the anode and the first hole-injection/hole-transport layer.
  • the anode comprises a thin layer of an organic conducting material adjacent to the hole- injection/hole-transport layer.
  • organic conducting materials include, but are not limited to, polyaniline, PEDOT-PSS, and a conducting or semi-conducting organic salt thereof.
  • a semi-transparent cathode such as used in Figure 2 is typically between 70 and 150 A thick.
  • the cathode comprises a single layer of one or more metals, at least one of which has a low work function.
  • metals include, but are not limited to, lithium, aluminum, magnesium, calcium, samarium, cesium and mixtures thereof.
  • the low work function metal is mixed with a binder metal, such as silver or indium.
  • the cathode further comprises a layer of dielectric material adjacent to the electron-injection/electron- transport layer, the dielectric material including, but not limited to, lithium fluoride, cesium fluoride, lithium chloride and cesium chloride.
  • the dielectric material is lithium fluoride or cesium fluoride.
  • the cathode comprises either aluminum and lithium fluoride, a mixture of magnesium and silver, a mixture of lithium and aluminum, or calcium followed by aluminum.
  • the cathode comprises magnesium, silver and lithium fluoride.
  • the hole-injection/hole-transport layer is about 750 A thick. Hole-injection/hole-transport layers typically comprise at least one material with good hole mobility.
  • Such materials include, but are not limited to, copper phthalocyanine (CuPc), and aromatic amine compounds such as N,N'-bis(l- naphthyl)-N,N'-diphenyl- 1 , 1 '-biphenyl-4,4'-diamine (NPD), bis(N,N'- 1 -naphthyl- phenyl-ammo-biphenyl)-biphenyl amine (BPA-DNPB) and bis(carbazol-N-biphenyl)- biphenyl amine (BPA-BCA).
  • CuPc copper phthalocyanine
  • NPD N,N'-bis(l- naphthyl)-N,N'-diphenyl- 1 , 1 '-biphenyl-4,4'-diamine
  • BPA-DNPB bis(N,N'- 1 -naphthyl- phenyl-ammo-bipheny
  • An OLED may further comprise an emitter layer between the electron- injection/electron-transport layer and the hole-injection/hole-transport layer in which electrons from the electron-injection/electron-transport layer and holes from the hole- injecting/hole-transport layer recombine.
  • OLEDs emit visible light of different colors.
  • Emitter layers typically comprise at least one host compound, either alone or together with at least one dopant compound, which is a luminophor.
  • host compounds include, but are not limited to, 2,2',7,7'-naphthyl-9,9'-spirobifluorene (N-SBF), ALQ, IDE- 120 and IDE- 140 (Idemitsu Kosan Co., Ltd., Tokyo, Japan).
  • Examples of dopant compounds include, but are not limited to, Coumarin 6, Coumarin 485, Coumarin, 487, Coumarin 490, Coumarin 498, Coumarin 500, Coumarin 503, Coumarin 504, Coumarin 504T, Coumarin 510, Coumarin 515, Coumarin 519, Coumarin 521, Coumarin 521T, Coumarin 522B, Coumarin 523, Coumarin 525, Coumarin 535, Coumarin 540A, Coumarin 545, Coumarin 545T, quinacridone derivatives such as diethyl pentyl quinacridone and dimethyl quinacridone, distyrylamine derivatives, such as IDE- 102, IDE- 105 (Idemitsu Kosan Co., Ltd., Tokyo, Japan), rubrene, DCJTB, pyrromethane 546, and mixtures thereof.
  • the structure of DCJTB is shown below:
  • the emitter layer emits white or blue light and comprises DCJTB, IDE- 102 and IDE-120.
  • the emitter layer may be between 200-400 A thick.
  • the electron-injection/electron-transport layer is typically about 350 A thick and comprises a compound such as ALQ, or a suitable oxadiazole derivative.
  • the electron-injectioii/electron-transport layer is N-SBF, ALQ, or a mixture of N-SBF and ALQ.
  • a blue-emitting OLED for use in color OLED displays comprises an anode comprising indium tin oxide, a hole-injection layer adjacent to the anode comprising CuPc, a hole-transport layer adjacent to the hole-injection layer comprising NPD, an emitter layer adjacent to the hole-transport layer comprising DCJTB, IDE-102 and IDE-120, an electron-transport layer adjacent to the emitter layer comprising ALQ, and a cathode comprising lithium fluoride and aluminum.
  • a method for forming patterned color changing materials on or under an OLED display device will now be described. The first step in the process is shown in Figure 4.
  • a blue-to-green CCM layer 401 is deposited on the protective layer 107 of an up-emitting monochromatic OLED display device, such as shown in Figure 1.
  • the layer 401 would be deposited on the substrate 307.
  • CCM layers can be deposited by any method known in the art, including spin-coating, meniscus-coating, spray-coating, dip-coating, blade-coating, from solution or suspension or by sublimation in a vacuum.
  • a photomask 501 is placed over the CCM layer 401 such that the light absorbing areas (i.e., areas that block light) 502 are aligned with every fourth electrode element 102 that will be green sub-pixels.
  • Light 503, preferably ultraviolet light, in an ambient atmosphere is shone through the photomask 501 to photo-oxidize the exposed areas of layer 401, causing them to become transparent.
  • the photomask 501 is transparent to the light 503 everywhere except in the light absorbing areas 502.
  • the blue-to-green CCM layer is photobleached in the areas 601 where the photomask is transparent to the light, while the areas masked by the light absorbing areas of the photomask comprise unbleached blue-to-green CCMs 602.
  • a protective layer 603 is then deposited on the patterned blue-to-green CCM 601, 602.
  • light having a wavelength of between about 250 nm and 420 nm, more preferably between about 300 nm and 400 nm and most preferably between about 330 nm and 380 nm is used for the photo-oxidation.
  • the source of the light can be a laser, a mercury lamp, a xenon lamp, or any other intense source of light and preferably of ultraviolet light.
  • a blue-to-red CCM layer 701 is deposited on the protective layer 603 that is deposited on the patterned blue-to-green CCM layer 601, 602.
  • Figure 8 shows the next step, where a photomask 801 is placed over the blue-to- red CCM layer 701 such that the light absorbing areas 802 are shifted over one electrode element and are aligned with every fourth electrode element 102 that will be red sub-pixels.
  • Light preferably ultraviolet light, in an ambient atmosphere 803 is shone through the photomask 801.
  • the photomask 801 is transparent to the light 803 everywhere except in the light absorbing areas 802.
  • the results of photo-oxidation of the blue-to-red CCM layer 701 is shown in Figure 9.
  • the blue-to-red CCM layer is photobleached in the areas 901 where the photomask is transparent to the light, while the areas masked by the light absorbing areas of the photomask comprise unbleached blue-to-red CCMs 902.
  • the blue-to-green CCMs 602 will not be photo-oxidized during this process because the protective layer 603, which absorbs the light used in the photo-oxidation process and because substantially no oxygen will penetrate into the CCM layer 602 after encapsulation.
  • the CCM layers are encapsulated and protected from photo- oxidation after the deposition and patterning steps of all CCM layers are finished, e.g.
  • the monochromatic OLED display emits blue light 904, which is either transmitted through the protective layers 107, 603, 903 and the bleached CCM layers 601, 901 at a blue sub-pixel 905 or is absorbed by the patterned blue-to-green CCM 602 or by the patterned blue-to-red CCM 902, which in turn emit green or red light, respectively, to form a green sub-pixel 906 and a red sub-pixel 907, respectively.
  • a full-color OLED display device is formed.
  • Photobleached or “photo-oxidized,” as used herein, means that a material becomes substantially transparent to visible light and that its photoluminescence is substantially eradicated upon exposure to, e.g., ultraviolet light and oxygen.
  • the photobleached parts of the CCM layers have blue-shifted absorption and transmit more than 90% of the light emitted by the monochromatic OLED display, and have remaining absolute quantum efficiency of photoluminescence of less than about 5 % , preferably less than about 1 %.
  • photo-oxidized areas transmit substantially all of the light having a wavelength between about 440 nm and 520 nm, more preferably between about 420 nm and 650 nm, and most preferably between about 400 nm and 750 nm.
  • FIG. 10 An additional embodiment of a full-color OLED display device is shown in Figure 10.
  • a filter layer 1001 that comprises a blue optical filter 1002 over each blue sub-pixel 905 is deposited on the third protective layer 903.
  • the color filters can be patterned or unpatterned and purify the emission spectrum.
  • a blue optical filter is pictured in Figure 10, it will be understood by one of skill in the art that color filters may be used with emission from the other sub-pixels, as well.
  • the monochromatic OLED display device emits blue light (close to CIE (0.155; 0.07)) and there are two CCM layers, one emitting red light (close to CIE (0.625; 0.34)) and the other emitting green light (close to CIE (0.28; 0.595)) to form a proper red-green-blue (“RGB”) display.
  • RGB red-green-blue
  • the photo-oxidation may be done using a standard ultraviolet mask-aligner or exposure tool or similar devices capable of achieving the desired resolution.
  • Mask aligners can easily achieve the preferred 1 - 5 ⁇ m resolution.
  • the wavelength of radiation used to photo-oxidize, e.g., the green CCM layer, in the presence of oxygen should at least partly overlap with the absorption spectrum of the green CCM (or at least of one of the components thereof) and should be capable of photobleaching the CCM layer in the desired manner described in the invention.
  • the wavelength of light used in the methods of the present invention which is preferably deep blue or ultraviolet light (preferably having a wavelength of between about 330 nm and 380 nm), is preferably optimized to the absorption of the color changing materials, e.g., by using excitation color filters to "tune" the wavelength of light.
  • the wavelength of light used to photo-oxidize the CCMs is absorbed in the underlying substrate in order to avoid wave-guiding and scattering that may reduce resolution and accuracy of the patterning process described herein.
  • Exposure time is also preferably optimized in order to achieve good transparency of the photo-oxidized portions of the CCM to blue light emitted from the underlying monochromatic OLED display, as well as to achieve low photoluminescence in the exposed areas.
  • Standard mask aligners normally allow light of sufficient intensity to penetrate through to the CCM so that CCM patterning can be achieved in a few minutes.
  • the time for photo-oxidation is between about 1 min. and 10 min., more preferably between about 1 min. and 3 min.
  • the CCM layers may further comprise chemicals such that, when the CCM is exposed to light, the exposed area is properly photobleached in the absence of oxygen.
  • the patterning can be done, e.g., in a dry and oxygen-free glove box, which may be useful if the CCMs are deposited and patterned directly on top of the an OLED.
  • the CCM layers may be exposed in the absence of water or oxygen to high-intensity ultraviolet light, which requires the use of highly stable CCMs.
  • CCMs When CCMs are deposited on a substrate (as shown in Figure 3), they may be deposited and patterned on a variety of substrates, including, but not limited to, glass, plastic, quartz, and sapphire. CCMs may be deposited and patterned as described in the present invention on the OLED itself, such as when the OLED is first deposited on the substrate and the CCMs are deposited on top, as shown in Figure 2. CCMs may alternatively be deposited on the substrate and patterned, and then the OLED may deposited on the CCMs, as shown in Figure 3. Preferably, the CCM layers are deposited on top of the OLED. In one configuration, shown in Figure 11, in an up- emitting OLED display device, there is no protective layer between the top electrode and the first CCM layer.
  • the blue OLED stack 1102 is deposited on the substrate 1101; one or more patterned CCM layers and protective layers 1103 are deposited directly onto the OLED stack 1102.
  • An encapsulation layer 1104 is deposited on the one or more CCM layers and protective layers 1103.
  • the one or more CCM layers and protective layers 1202 are deposited directly onto a transparent substrate 1201; the OLED stack 1203 is then deposited onto the one or more CCM layers and protective layers 1202 and an encapsulation layer 1204 is deposited on the OLED stack.
  • the one or more CCM layers and protective layers 1302 are deposited on a first encapsulation layer 1301.
  • a transparent substrate 1303 is then deposited on the one or more CCM layers and protective layers 1302.
  • An OLED stack 1304 is deposited on the transparent substrate 1303, and a second encapsulation layer 1305 is deposited on the OLED stack 1304.
  • one or more CCM and protective layers 1402 may be deposited and patterned as described in the invention on a separate transparent substrate 1401 (e.g., a glass slide also used to encapsulate the OLED display) which is subsequently aligned on and then laminated or bonded or glued 1403 to an OLED stack 1404 that is deposited on a substrate 1405.
  • a separate transparent substrate 1401 e.g., a glass slide also used to encapsulate the OLED display
  • Such a configuration may also serve to encapsulate the OLED display.
  • all CCM layers may be deposited on one and the same substrate (on top of each other with alternating protective layers), or on different substrates, in which case protective layers may not be needed.
  • the protective layer preferably comprises inert materials that are transparent and have low or no luminescence.
  • the protective layer is preferably not patterned. Without being bound by any theory, the protective layer absorbs the radiation used in the patterning method and/or prevents ambient oxygen from penetrating to the lower layers in order to prevent the already-patterned underlying layers from being re-exposed.
  • Suitable materials for the protective layer are preferably able to absorb light used in the methods of the present invention (usually ultraviolet light), are able to block oxygen penetration into the other layers, are transparent to visible light (usually red, green and blue), are non-fluorescent and are easily deposited onto the CCM layers without harming them.
  • light used in the methods of the present invention usually ultraviolet light
  • are able to block oxygen penetration into the other layers are transparent to visible light (usually red, green and blue), are non-fluorescent and are easily deposited onto the CCM layers without harming them.
  • such materials are deposited onto the CCM layers by heat or e-beam evaporation or are sputtered (reactive DC or RF).
  • Suitable protective layer materials are known in the art and include, but are not limited to, metal oxides such as SiO 2 , SIN, MgO, and ITO, organic polymers, conjugated polymers, additives such as benzophenones, heat and/or ultraviolet curing epoxy compounds, spin-on-glass materials, siloxanes and combinations thereof. If the protective layer material is fluorescent, it may be quenched by, e.g., photo-oxidation if photoluminescent quenchers such as metals, ions, dopants or other impurities are added to the material.
  • a protective layer may also be used on a substrate if, for example, the optimum wavelength of light for patterning is in a range where the substrate does not absorb.
  • glass strongly absorbs light of wavelength below 330 nm. Therefore, if a glass substrate is used with a wavelength of light for patterning the CCM layers (particularly when the first CCM layer is on the substrate) that is above 330 nm, then the light may penetrate the substrate and be waveguided and/or scattered. This in turn could result in a partial or even complete photo-oxidation of those parts of the CCM film that not to be photo-oxidized. In this case it may be preferable to cover the substrate with a protective layer in order to avoid waveguiding and/or scattering effects. Alternatively, special glass or other substrate materials may be used that strongly absorb the wavelength of light used for patterning. Examples of such materials include colored glass, such as Schott glass filters.
  • Color changing materials may comprise any material known in the art.
  • CCM layers may comprise compounds including, but not limited to, pure sublimed luminophors (such as those used in the emitter layers of OLEDs), sublimed host molecules (luminophors) that are doped (co-evaporated) with other materials in order to improve quantum efficiency of photoluminescence, purely organic or organo- metallic materials, or unconjugated, conjugated or partially conjugated polymers or co-polymers.
  • the host can be chosen to optimize its absorption of the wavelength of light emitted by the monochromatic OLED display (usually blue light), and the dopant can be chosen to emit the desired wavelength of light (usually red or green light).
  • Examples of dopant compounds include, but are not limited to, Coumarin 6, Coumarin 485, Coumarin, 487, Coumarin 490, Coumarin 498, Coumarin 500, Coumarin 503, Coumarin 504, Coumarin 504T, Coumarin 510, Coumarin 515, Coumarin 519, Coumarin 521, Coumarin 52 IT, Coumarin 522B, Coumarin 523, Coumarin 525, Coumarin 535, Coumarin 540A, Coumarin 545, Coumarin 545T, quinacridone derivatives such as diethyl pentyl quinacridone and dimethyl quinacridone, distyrylamine derivatives, such as IDE- 102, IDE-105 (Idemitsu Kosan Co., Ltd., Tokyo, Japan), rabrene, DCJTB, pyrromethane 546, and mixtures thereof.
  • dopant compounds include, but are not limited to, Coumarin 6, Coumarin 485, Coumarin, 487, Coumarin 490, Coumarin 498, Coumarin 500, Coumarin 503, Coumarin 50
  • Color changing materials can also comprise pure polymers or polymer blends, fluorescent polymers or luminophors doped into conjugated or partly conjugated fluorescent or nonfluorescent polymers.
  • a wide range of polymers and copolymers are available as CCMs because different side groups can be attached to a particular backbone.
  • co-polymers can be used. Examples of useful polymers in CCMs are known in the art and include, but are not limited to, PPV polymers, thiophene-based polymers, inert polymers with attached luminophor side groups, fluorene-based polymers, phenylene-based polymers, furylene-based polymers, oligomers, oligomers with spiro centers, and combinations and co-polymers thereof.
  • CCMs are doped materials, polymer blends and copolymers.
  • CCM materials for use in the methods of the present invention are preferably rendered non-luminescent (or have very low luminescence) and are substantially transparent to visible light when photo-oxidized.
  • CCM materials for use in the methods of the present invention can be patterned without removing any material from the CCM layer. If guest/host CCM films are used then at least one but preferably both of the two (or more) components are rendered inactive, i.e., they do not absorb visible light and do not emit light by photoluminescence.
  • CCMs that emit red or green light preferably have an absolute quantum efficiency of photoluminescence that is greater than about 50% , preferably greater than about 70%, and more preferably greater than about 80%.
  • Such efficiencies are preferably achieved by multi-component color changing materials, wherein the major component (comprising about 90-98% of the material) absorbs blue light efficiently, the minor component (dopant) has high quantum efficiency of photoluminescence in the desired wavelength range, and there is efficient energy transfer from the major component to the dopant.
  • a blue-to-green CCM may be Coumarin 540-doped ALQ and a blue-to-red CCM may be DCJT-doped ALQ.
  • a blue-to red CCM is a PPV copolymer with cyano- groups attached to the vinyl groups of the polymer backbone or a poly-alkyl-thiophene polymer
  • a blue-to-green CCM is a polyfluorene-based copolymer, a PPV polymer with discontinuous conjugation (i.e., with electrically and optically inert spacer groups) or a PPV polymer with solubilising side groups, such as a di-alkyl PPV.
  • Particularly preferred blue-to-red CCM materials include, but are not limited to:
  • a particularly preferred blue-to-green CCM has the formula:
  • CCM layers are preferably less than about 3 ⁇ m thick, more preferably less than about 2 ⁇ m thick, and most preferably less than about 1 ⁇ m thick. As the thickness of the CCM layers increases, the layers may waveguide or scatter the light they emit, which in turn may lead to loss of brightness and contrast in the displays. Color changing materials preferably have optical densities for the excitation and patterning light sources of greater than about 1, more preferably between about 2 - 4 (i.e., transmission of about 0.01% to about l%)and most preferably between about 2- 3. If the optical density of the CCMs are further increased in order to absorb more light from the monochromatic OLED display, some of the green or red photoluminescence from the materials may be re-absorbed in the CCM layers, thus reducing the brightness of the display.
  • EXAMPLE 1 OPTIMIZATION OF CCM PATTERNING BY PHOTO-
  • a glass substrate 1501 is carefully cleaned and a thin film of a standard green emitter, ALQ and a dye, such as Coumarin 540 1502 is evaporated thereon.
  • the substrate must be very clean and free of water.
  • the initial thickness of the evaporated layer 1502 is about 200 nm.
  • the absorption spectrum of the film 1502 deposited in step 1 is measured and compared with the emission spectrum of a blue-emitting OLED. For example, a good CCM candidate absorbs about 95 % of the blue light from the underlying OLED. If this is not the case, then the thickness of the film 1502 may be increased until about 95% of the blue light is absorbed. Alternatively, the host material in the green film can be changed to one that absorbs the light more efficiently. The sufficiency of absorption of the blue emission can be checked by placing the green film over a blue-emitting device and measuring how much of the blue light is transmitted (with reference to the amount of light emitted by the blue- emitting OLED without the film on top).
  • the green film 1602 on the substrate 1601 is exposed to ultraviolet light 1603 through a suitable photomask 1604 (pattern size of 1 mm or less) in the presence of ambient oxygen.
  • the photo mask 1604 comprises areas 1605 that are transparent to ultraviolet light and other areas 1606 that block ultraviolet light.
  • the optimal intensity of light and time (dose) for exposure is when the areas of film 1607 that are exposed to ultraviolet light and oxygen have no or very low fluorescence and when their absorption is blue-shifted such that they become highly (ideally fully) transparent to blue light emitted from the OLED which the film will cover.
  • the areas that are not exposed to ultraviolet light 1608 should remain highly fluorescent, just as in the original film.
  • the mask 1604 and substrate 1601 with the CCM film 1602 are preferably in close proximity to each other.
  • the wavelengths of ultraviolet light from the exposure tool used to photobleach the green film should only contain wavelengths that both overlap with the absorption spectrum of the film and are strongly absorbed into the substrate material.
  • it may be preferable to alter the ultraviolet excitation spectrum e.g., by using band pass filters.
  • FIG. 17 An alternative solution is shown in Figure 17, where a protective layer 1702 can be placed between the substrate 1701 and the green film 1703 in order to minimize scattering and waveguiding of the ultraviolet light by the substrate.
  • a protective layer 1702 can be placed between the substrate 1701 and the green film 1703 in order to minimize scattering and waveguiding of the ultraviolet light by the substrate.
  • the quality and performance of such patterned CCM films can easily be checked in a standard fluorescence microscope.
  • the photo-patterned film 1802 is encapsulated by evaporating a film of a transparent dielectric, including but not limited to SiO 2 , perylene and Al O 3 1803 onto the film.
  • the encapsulation layer may also be deposited by sputtering or other methods. Alternatively, spin-on glass materials may be used for encapsulation.
  • Encapsulated films may be placed over a blue or ultraviolet light source in order to monitor the stability of the photoluminescence (intensity and spectrum) of the patterned film over time. If no protective layer is deposited on the film, then it will be prone to degradation from the environment (water, light, oxygen).
  • the same process can be repeated for patterning a red film comprising a red dye doped into ALQ.
  • the protective layer is essential to prevent ultraviolet absorption by the green film during patterning of the red film, as well as oxygen penetration to lower layers. If the green film and the red film are to be used on the same monochromatic OLED display, then the photomask pattern for the second CCM layer must be laterally shifted from the photomask pattern used to pattern the first
  • the CCM layers are patterned directly on the OLED rather than on separate substrates, which allows for easier alignment of the patterns over the underlying OLED's electrode elements.

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Abstract

La présente invention concerne des procédés de configuration de couches organiques à diode électroluminescente organique (OLED) par photo-oxydation. La présente invention concerne en particulier des procédés de configuration de couches de matériaux de changement de couleur en utilisant la lumière et l'oxygène ambiant, avec un photomasque, afin de soumettre les zones non masquées des couches à un photoblanchiement. Les matériaux de changement de couleur peuvent être configurés sans être éliminés physiquement de la couche. Ce procédé permet d'obtenir des zones photoblanchies de couches de matériaux de changement de couleur n'absorbant ou n'émettant pas de lumière et qui sont sensiblement transparentes à la lumière visible. Les procédés de l'invention sont utilisés en particulier dans la fabrication de dispositifs d'affichage OLED de haute résolution tout en couleur comprenant des couches de matériaux de changement de couleur fluorescentes configurées permettant d'obtenir des sous-pixels rouges et verts à partir d'un dispositif d'affichage OLED monochrome émetteur de bleu.
PCT/US2001/024597 2000-08-01 2001-08-01 Procede de configuration de supports de changement de couleur pour dispositifs d'affichage a diode electroluminescente organique WO2002011209A2 (fr)

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WO2005116521A1 (fr) * 2004-05-28 2005-12-08 Tir Systems Ltd. Appareil pour ameliorer la luminance et procede correspondant
DE102004042356A1 (de) * 2004-09-01 2006-03-02 Siemens Ag Anzeigeeinheit und Verfahren zur Herstellung einer Anzeigeeinheit
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DE102007053069A1 (de) * 2007-09-27 2009-04-02 Osram Opto Semiconductors Gmbh Lichtemittierendes Bauelement mit Wellenlängenkonverter und Herstellungsverfahren
US7649001B2 (en) 2002-08-12 2010-01-19 Takeda Pharmaceutical Company Limited Fused benzene derivative and use
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WO2013133139A1 (fr) * 2012-03-07 2013-09-12 シャープ株式会社 Substrat de conversion de longueur d'onde et dispositif d'affichage l'utilisant, appareil électronique, et méthode de fabrication d'un substrat de conversion de longueur d'onde
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US7649001B2 (en) 2002-08-12 2010-01-19 Takeda Pharmaceutical Company Limited Fused benzene derivative and use
DE10312679A1 (de) * 2003-03-21 2004-10-07 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verfahren zum Ändern einer Umwandlungseigenschaft einer Spektrumsumwandlungsschicht für ein lichtemittierendes Bauelement und lichtemittierendes Bauelement
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WO2004084315A1 (fr) * 2003-03-21 2004-09-30 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procede pour modifier une propriete de conversion d'une couche de conversion de spectre pour un composant electroluminescent
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US7812359B2 (en) 2005-06-21 2010-10-12 Au Optronics Corp. Organic electroluminescent device
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GB2432249A (en) * 2005-11-15 2007-05-16 Fuji Electric Holdings Co Colour filter with colour conversion function
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