GB2357889A - Fluorescent colour conversion film - Google Patents
Fluorescent colour conversion film Download PDFInfo
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- GB2357889A GB2357889A GB0026062A GB0026062A GB2357889A GB 2357889 A GB2357889 A GB 2357889A GB 0026062 A GB0026062 A GB 0026062A GB 0026062 A GB0026062 A GB 0026062A GB 2357889 A GB2357889 A GB 2357889A
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- Prior art keywords
- color conversion
- fluorescent
- fluorescent color
- filter
- light
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G02B1/105—
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- 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]
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
A fluorescent colour conversion filter has a transparent substrate (1) supporting a colour filter layer formed of red, green and blue filter layer regions (2, 3 and 4). On top of the red filter layer region, there is provided a fluorescent colour conversion film (5) comprising at least one organic fluorescent coloring material which absorbs light obtained from a luminescent body in the near ultraviolet to the visible range and emits a visible light of a different wavelength; at least one molecular weight adjusting agent; and at least one matrix resin which supports said organic fluorescent colouring material and said molecular weight adjusting agent. The molecular weight adjusting agent contains at least one compound represented by the following general formula (I):- <EMI ID=2.1 HE=23 WI=35 LX=704 LY=1842 TI=CF> <BR> <PC>wherein each of A and B is independently selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted heterocyclic group and anunsubstituted heterocyclic group. The filter also includes a protective layer (6) and an insulated inorganic oxide film (7). In an organic luminescent element including such filter, an organic luminescent body is provided over the film (7).
Description
2357889 FLUORESCENT COLOR CONVERSION FILM, AND FILTER AND LUMINESCENT
ELEMENT EQUIPPED WITH SAME The present invention relates to a fluorescent color conversion film for taking light, which is emitted from a luminescent body in the near ultraviolet range to visible range, and converting it to visible light of a different wavelength. The present invention also relates to a fluorescent color conversion filter using this fluorescent color conversion film, and to an organic luminescent element equipped with this fluorescent color conversion filter. This fluorescent color conversion film, or fluorescent color conversion filter using this color conversion film, is well suited for use in personal and industrial display devices, such as luminescent type multi-color or full color displays, display panels, backlights, and the like.
With the increased demand for flat panel display instead of the traditional cathode ray tube, there has been much effort towards the development and application of various display elements. Electroluminescence elements (henceforth referred to as luminescent elements) are a result of this demand. They have been gathering interest particularly because it is a total body self-luminescent element having a high resolution and high visibility that other displays do not have.
As a method for multi-color or full colorization of a flat panel display, the following several methods are known. The first method is a method of separately arranging luminescent bodies of the three primary colors of red (R), green (G), blue (B) (henceforth may be referred to as RGB) in a matrix and illuminating each of these (described in Japanese Laid-Open Patent Number 57-157487, Japanese Laid-Open Patent Number 58-147989, Japanese Laid-Open Number 3-214593, and the like).
1 When colorizing using organic luminescent elements, the three types of luminesc(nt materials for RGB must be placed in a highly detailed matrix. This is technically difficult and cannot be manufactured inexpensively. Furthermore, because the three types of luminescent materials have differing lifespans, over time, discrepancies ill the colors can arise.
The second method is a method wherein the three primary colors are transmitted using color filters on a backlight that emits white light (Japanese Laid Open Paten Number 1-315988, Japanese Laid Open Patent Number 2-273496, Japanese Laid Open Patent Number 3-194895, and the like). However, a long-life luminescent material and an organic luminescent element with a high luminance white light ar' needed in order to obtain a RGB with a high luminance, and these have not yet been achieved.
The third method is a method wherein the luminescence from a luminescent body is absorbed by fluorescent bodies which have a separated arrangement in a plane, an 1 from each of the fluorescent bodies, fluorescent light of multiple colors is emitted (described in Japanese Laid Open Patent Number 3-152897, and the like). This method has been applied to cathode ray tubes (CRT) and plasma displays and the like. However, because the fluorescent body used as the organic luminescent element is a fluorescent coloning material used in lasers and the like, there can be decomposition or loss of activity during the process of heat or light irradiation during manufacturing. There is reduction in the color conversion capability.
As a fourth method relating to the above described first to third methods, in recent years, there has been disclosed a color conversion method, wherein fluorescent 2 material, which can emit fluorescent light in the visible range by absorbing light in the emitted range of an organic luminescent element, is used as a filter (Japanese Laid Open Patent Number 3-152897, Japanese Laid Open Patent Number 5-258860, and the like). In this method, because the emitted color of the organic luminescent element is not limited to white light, an organic luminescent element with a higher luminance can be used as the light source. For example, a color conversion method using an organic luminescent element with a blue luminescence (described in Japanese Laid Open Patent Number 3-152987, Japanese Laid-Open Patent Number 8-286033, Japanese Laid-Open Patent Number 9-208944) can have a wavelength conversion from blue light to green light or red light.
With highly detailed patteming of the fluorescent color conversion film containing fluorescent coloring material constructed according to the color conversion method as described above, a full color luminescent display can be constructed even when a weak energy ray, such as near infrared to visible light, of a luminescent body is used. With regard to methods for patterning of the fluorescent color conversion filter, there are (1) as with inorganic fluorescent bodies, methods, wherein: after dispersing fluorescent coloring material in a liquid resist (photoreactive polymer) and creating a film with this by spin coat method or the like, patterning is conducted by a photolithography method (Japanese Laid Open Patent Number 5-198921, Japanese Laid-Open Patent Number 5-258860, and the like), and (2) a method, wherein: fluorescent coloring material or fluorescent pigment is dispersed in a basic binder, and this is etched with an acidic aqueous solution (described in Japanese Laid Open Patent Number 9-208944).
3 However, with the method of patterning by the photolithography method of the above (1), the organic fluorescent coloring material could decompose or become quenched in the photolithography process due to attack by radicals generated fror 1 light polymerization agents and/or heat hardening agents (polymerization initiators) in the resist, or from attack by growth radicals from reactive multifunctional monomers and oligorners. As a result, there is a problem of a reduced luminescenre efficiency.
Furthermore, with the method of etching by an acidic aqueous solution of the abo ve (2), patterning is conducted after coating the resist on top of a fluorescent color conversion film, which comprises a basic binder. As a result, there are many step in the manufacturing process. Furthermore, there are problems such as pattern thinning due to side etching, and the like.
An object of the present invention is to provide a fluorescent color conversion 111m, a fluorescent color conversion filter having this fluorescent color conversion film, and an organic luminescent element equipped with this fluorescent color conversion filter, in which the fluorescent color conversion filter is manufactured using a photolithography process and in which the decomposition and quenching of the fluorescent coloring material resulting ftom attacks from radicals generated from polymerization initiators and/or growth radicals of reactive multifunctional i monomers are suppressed.
According to a first aspect of the present invention, there is provided a fluorescencolor conversion film comprising at least one organic fluorescent coloring materh 1 which is capable of absorbing light obtained from a luminescent body in the near 4 ultraviolet range to visible range and emitting a different visible light; at least one molecular weight adjusting agent; and at least one matrix resin which supports the organic fluorescent coloring material and the molecular weight adjusting agent; wherein the molecular weight adjusting agent contains at least one compound represented by the following general formula (I).
CH2 11 (1) U'-- B wherein each of A and B is independently selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted heterocyclic group and an unsubstituted heterocyclic group.
The content of the above molecular weight adjusting agent in the above fluorescent color conversion film is preferably in the range of 0.01 to 5 weight %, based on the weight of the above fluorescent color conversion film.
According to a second aspect of the present invention, there is provided a fluorescent color conversion filter comprising a fluorescent color conversion film according to said first aspect of the present invention, and a substrate which supports said fluorescent color conversion film.
According to a third aspect of the present invention, there is provided an organic luminescent element having a fluorescent color conversion filter according to said second aspect of the present invention, and an organic luminescent body which is adapted to emit light that enters this fluorescent color conversion filter. The present invention will now be described in further detail in the following embodiments.
1. Fluorescent color conversion film The fluorescent color conversion film of the present invention contains an organic. fluorescent coloring material which absorbs light, which is emitted from a luminescent body in the near ultraviolet to visible range, and converts it to visible light of a different wavelength; a molecular weight adjusting agent; a matrix resin which supports this organic fluorescent coloring material and the molecular weig it adjusting agent. Each of the construction elements of the fluorescent color conversion film is described in more detail below.
1) Organic fluorescent coloring material The organic fluorescent coloring material contained in the fluorescent color conversion film according to the present invention is one which absorbs light emitted from a luminescent body in the near ultraviolet to visible range, particularly in the range of blue to blue-green light, and emits a visible light of a differing wavelength. In general, it is easy to obtain an organic luminescent element that emits light in the blue to blue-green range. However, if this is converted to light in the red range by simply passing the light through a red filter, because the light emitted by this element has only a small amount of light of wavelengths in the red range, the light output is very dark. Therefore, it is preferable to use at least one type of organic fluorescent coloring material which emits fluorescent in at least he red range and combine with at least one type of organic fluorescent coloring malerial 6 which emits light in the green range. In other words, for the light in the red range, the light from this element is converted to light in the red range by the fluorescent coloring material, and this results in an output of adequate intensity.
On the other hand, for light in the green range, as with the light in the red range, the light from this element can be converted to green light by a different organic fluorescent coloring material, or else, if there is a sufficient amount of light in the green range emitted by this element, then the light from this element can be simply passed through a green filter. With regard to light in the blue region, it is possible to output blue light by simply passing the light from the organic luminescent element through a blue filter.
Examples of fluorescent coloring material that absorb light emitted from a luminescent body in the blue to blue-green range and emit fluorescence in the red range include: rhodamine coloring materials, such as rhodamine B, rhodamine 6G, rhodamine 3B, rhodamine 10 1, rhodamine 110, sulforhodamine, basic violet 11, basic red 2, and the like; cyanine coloring materials; pyridine coloring materials, such as 1 -ethyl-2-[4-(pdimethylaminophenyl)- 1,3 -butadienyl)-pyridium-perchlorate (pyridine 1), and the like; or oxazine coloring materials, and the like. Furthermore, various dyes (direct dyes. acid dyes, base dyes, disperse dyes, and the like) can be used if they are fluorescent.
Furthermore, examples of organic fluorescent coloring materials that absorb light emitted from the luminescent body in the blue to blue green range of light and that emit fluorescence in the green range include: cournarin coloring materials, such as 3(2'-benzothiazolyl)-7diethylaminocoumarin (cournarin 6), 3-(2'-benzoimidazolyl)- 7 7-N,N-diethylaminocoumarin (coumarin 7), 3-(2'-N-methylbenzoimidazolyl)7N,N-diethylaminocouniarin (coumarin 3 0), 2,3,5,6- 1 H,4H-tetrahydro8trifluoromethyl quinolizine (9,9a, I-gli) coumarin (coumarin 153), and the like, or basic yellow 51 which is a coumarin coloring material dye, and in addition naphthalimide coloring materials such as solvent yellow 11, solvent yellow 116, ' nd the like. Furthermore, various dyes (direct dyes, acid dyes, base dyes, disperse dys, and the like) can be used if they are fluorescent.
Furthermore, the organic fluorescent coloring materials of the present invention c an be made into organic fluorescent pigments by mixing in advance with ester polymethacrylate, polyvinyl chloride, vinyl chloridevinyl acetate copolymer resi alkyd resin, aromatic sulfonamide resin, urea resin, melamine resin, benzoguanarnine resin, and resin mixtures of these. Furthermore, these organic fluorescent coloring materials and organic fluorescent pigments (in this specification, these two are both collectively referred to as organic fluorescent coloring material) can be used singly, or two or more types can be combined and used in order to adjust the hue of the fluorescence.
Based on the weight of the conversion film, the organic fluorescent coloring mat -.rial content in the fluorescent color conversion film is 0. 0 1 -5 weight % and preferabl y 0. 1-2 weight %. If the organic fluorescent coloring material content is less than 0.0 1 weight %, then an adequate wavelength conversion cannot be conducted. If the content of this organic fluorescent coloring material exceeds 5 weight %, there is reduced color conversion efficiency due to the effect of concentration quenching and the like.
8 2) Matrix resin For the matrix resin used in the fluorescent color conversion film of the present invention, a light hardening or a light and heat hardening resin is light and/or heat treated; radical seeds or ion seeds are generated; and the resin is polymerized or cross-linked and made insoluble and infusible. Furthermore, in order to conduct patterning of the fluorescent color conversion film, the light hardening or heat and light hardening resin, prior to hardening, is preferably soluble in an organic solvent or alkaline solution. Stated more concretely, the light hardening or heat and light hardening resin preferably used in the present invention is (1) a resin in which a composition film, comprising an acrylic multifunctional monomer and oligomer containing a plurality of acroyl groups or methacroyl groups and a light or heat polymerization initiator, is light or heat treated, and light radicals or heat radicals are generated, and the resin is polymerized; (2) a composition, comprising ester polyvinyl cinnamate and a sensitizer, is dimerized by light or heat treatment and cross-linked; (3) a composition film, comprising a chain or a cyclic olefin and bisazide, is light or heat treated to generate nitrene and is cross-linked to an olefin; (4) a composition film, comprising a monomer containing an epoxy group and a photo acid generating agent, is light or heat treated to generate acid (cation) and is polymerized. In particular, the light hardening or heat and light hardening resin of (1) can be patterned with high detail and is also preferable for reliability in terms of solvent resistance, heat resistance, and the like.
(3) Molecular weight adjusting agent As noted above, the molecular weight adjusting agent used in the fluorescent color conversion film of the present invention contains at least one compound represented by the following general formula (1) CH2 wherein each of A and B is independently selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted heterocyclic group and an unsubstituted heterocyclic group.
In Japanese Laid Open Patent Number 8-3208, with regard to the technology relating to radical polymerization, it is disclosed that, for example, 1 diphenyl ethylene can be used as a molecular weight adjusting agent for the reaction of radical polymerization and the like. Furthermore, in Japanese Laid Open Patent Number 4980188, it is disclosed that such compounds can delay the polymerization reactior of the radical polymer, and at the same time, it can restrict the molecular weight distribution.
Similarly, because the compound represented by the above general formula (1) used in the fluorescent color conversion film of the present invention does not selfpolymerize, when radicals generated from the organic fluorescent coloring materIal and the compound represented by the above general formula (1) react, it is thougla that the radical polymerization can be stopped. In other words, in the reaction Of. -.he radical polymerization and the like, it can be used as a molecular weight adjusting agent. Furthermore, this molecular weight adjusting agent can delay polymerization reaction of the radical polymers. At the same time, it has the action of restricting the molecular weight distribution. Therefore, by having a compound represented by the above general formula (I) as a molecular weight adjusting agent in the fluorescent color conversion film, growth radicals at the high molecular weight end, which are generated by chain reactions of the radicals generated by light polymerization initiators and reactive multifunctional monomers, are stopped. The radical density in the system can be controlled, and excessive attack by radicals can be buffered. The decomposition and quenching of the organic fluorescent coloring material can be controlled.
Examples of unsubstituted aromatic groups include aromatic groups not having substitution groups, such as a phenyl group, a naphthyl group, and the like.
Furthermore, substituted aromatic groups include the above unsubstituted aromatic groups with at least one substitution group of halogen atom, alkyl group, alkoxyl group, hydroxyl group, amino group, and the like, for example. In general, substitution groups called aryl and arylene groups are suitable.
Furthermore, unsubstituted heterocyclic groups are those that contain at least one hetero atom of thienyl, furyl, pyrrole, pyridyl, indole, and the like.
Furthermore, substituted heterocyclic groups are those that have at least one substitution group of a halogen atom, alkyl group, alkoxyl group, hydroxyl group, amino group, and the like in the above unsubstituted aromatic group.
Based on the weight of the fluorescent color conversion film, the molecular weight adjusting agent used in the present invention preferably has a content in the range of 0.0 1-5 weight %, and more preferably 0. 1 1 weight % in the fluorescent color conversion film. If the molecular weight adjusting agent content in the fluorescent color conversion film is less than 0.01 weight %, an adequate control of the molecular weight may not be possible. Furthermore, if the molecular weight adjusting agent content exceeds 5 %, there may be low polymerization, and a cok conversion film with an adequate strength may not be obtained.
Examples of the molecular weight adjusting agent which are suitable for use in th fluorescent color conversion film of the present invention are represented by the formulae (P 1) to (P 12), but they are not limited to these.
H2C=C CH3 H2C=C (P2) CH3 C2H5 (P3) H2C=C CL C2H5 12 H2C=C 0 OCH3 (P4) CLOCH3 H2C=C 0 0C2H5 (P5) CL C2H5 H2C=C 0 OH (P6) 11:)1,0H H2C=C J(: cl q-7) CLCI H2C=C c (P8) CLCH3 13 H2C=C H2C=C S H2C=C C H (P12) H2C=C H N CH3 14 2. Fluorescent color conversion filter The fluorescent color conversion filter of the present invention is equipped with at least the above fluorescent color conversion film and a substrate. By using the fluorescent color conversion film with the above construction in the fluorescent color conversion filter, the decomposition and quenching of the fluorescent coloring material in the photolithography process can be suppressed, and it becomes possible to improve the decline in the color conversion process. In addition, the fluorescent color conversion filter of the present invention can also have color filters, as needed. By having a color filter layer on the fluorescent color conversion filter, the hue of the output light can be adjusted.
In the accompanying drawings, Figs. 1 and 2 are schematic cross-sectional views of, respectively, an embodiment of a fluorescent color conversion filter and an embodiment of an organic luminescent element, according to the present invention.
Referring to Figure 1, there is shown a schematic cross-sectional illustrating a portion corresponding to a single picture element of a fluorescent color conversion filter having a plurality of picture elements for use as a multi-color or full-color display. Such a filter is constructed from a transparent substrate 1; a color filter layer (defined by a red filter layer region 2, a green filter layer region 3, and a blue filter layer region 4) provided on top of transparent substrate I; a fluorescent color conversion film 5 provided on top of one of the filter layer regions of this color filter layer (in Figure 1, it is provided on top of the red filter layer region 2). If necessary, a protective layer 6 can be provided on top of the fluorescent color conversion film 5, and an insulated inorganic oxide film 7 can be provided on top of the protective layer 6. A specified pattern is formed on this laminate.
The fluorescent color conversion film 5 is constructed from at least one organic fluorescent coloring material which emits fluorescence in the red region; a matrix resin which is made by hardening a light hardenable or heat and light hardenable resin; a molecular weight adjusting agent containing at least one compound represented by above general formula (I). The red filter layer region 2 allows the red light converted by fluorescent color conversion film 5 to pass and removes the other colors.
The green filter layer region 3 and the blue filter layer region 4 each has its own specific pattern. From the light radiating from an organic luminescent body (not shown in Fig. 1), each of these color filter layer regions only transmits green light or blue light and outputs light of its respective color. 1 The fluorescent color conversion filter with the construction of Figure 1 outputs light in the green range by using only green filter layer 3. However, if needed, a fluorescent color conversion film for green color may be provided on top of greer filter layer region 3.
A suitable substrate for the present invention is preferably transparent with respect to light in the visible range. It preferably also has dimensional stability. Suitable materials for the substrate include glass, quartz, sapphire, and macromolecules of polyimides and the like. However, the substrate is not limited to these materials.
The fluorescent color conversion film of the present invention can be formed by coating on a suitable substrate by using known methods of spin coating, casting, 16 immersion coating, and the like. The coating may be conducted using a solution or dispersion solution containing the organic fluorescent coloring material, a component which will form the matrix resin, and a molecular weight adjusting agent represented by the above general formula (1). Although it also depends on the organic fluorescent coloring material content, the thickness of the fluorescent color conversion film is preferably 0. 1-5 0 micrometers, and more preferably LO-1 0 micrometers. The patterning of the fluorescent color conversion film can be conducted using a photolithography method.
A color filter layer can be used in the fluorescent color conversion filter of the present invention in order to adjust the hue of the output light of the organic luminescent element of the present invention. In order to adjust the hue of the light which has had a wavelength conversion by the fluorescent color conversion film, the color filter is placed between the substrate and the fluorescent color conversion film. Alternatively, by placing the color filter layer in an area on top of the substrate without a fluorescent color conversion film, the hue of the light emitted from the organic luminescent body can be adjusted. The color filter can be manufactured using standard and commercial materials.
As described above, the fluorescent color conversion filter of the present invention can be further equipped as needed with protective layer 6 and insulated oxide film 7.
Protective layer 6, which is provided as needed, is preferably formed so as to cover the fluorescent color conversion film 5. Taking into consideration the later steps, with protective layer 6, the surface opposite the side where protective layer 6 contacts fluorescent color conversion film 5 is preferably approximately a flat plane.
17 Protective layer 6 may be formed by using standard resins and standard coating methods. Protective layer 6 is preferably transparent in the visible range. i Insulated inorganic oxide film 7, which is provided as needed, is preferably provided on top of protective layer 6, which has an approximate flat plane surface. Insulated inorganic oxide film 7 can be formed by standard methods of vacuum deposition, sputtering, CVD, and the like. Furthermore, insulated inorganic oxide film 7 is preferably also transparent with respect to a light source in the visible range. An Si02 film and the like is preferred.
Another embodiment of the fluorescent color conversion filter of the present invention may be equipped with at least the following: a fluorescent color conversion filter; a transparent substrate; a color filter layer provided on top of this transparent substrate as needed; and a fluorescent color conversion film uniformly covering the entire surface of the substrate. This can be used as a backlight.
A further embodiment of the fluorescent color conversion filter of the present invention may be equipped with at least the following: a transparent substrate, and a fluorescent color conversion film only in specified regions on top of this transparInt substrate. This can be used as a display device.
3. Organic luminescent element Referring to Figure 2, there is shown a portion corresponding to a single picture element of an organic luminescent element which is used for multicolor or full co or displays and which has a plurality of picture elements. The organic luminescent element of Fig. 2 is equipped with a fluorescent color conversion filter 8 which is of 18 the type described above in relation to Fig. 1, and with an organic luminescent body 9. With this construction, light from the near ultraviolet to visible range, and preferably in the blue to blue-green range, is emitted from organic luminescent body 9. This light enters the fluorescent color conversion filter 8, and a visible light of a different wavelength is outputted from fluorescent color conversion filter 8.
Fluorescent color conversion filter 8 is constructed using the above described fluorescent color conversion film 5. In other words, by containing a compound represented by the above general formula (1), the decomposition and quenching of the fluorescent coloring material in the photolithography process can be suppressed. As a result, fluorescent color conversion film 5 can be highly detailed, and the color conversion efficiency can be improved. Thus, by combining this fluorescent color conversion filter 8 and organic luminescent body 9, an organic luminescent element that is highly detailed and has high color conversion efficiency can be easily obtained. Furthermore, when trying to achieve an organic luminescent element which emits light of the same luminance, by using a fluorescent filter with a high color conversion efficiency, the luminance of the organic luminescent body can be reduced, and therefore, the driving voltage can be reduced.
Organic fluorescent body 9 has a construction in which an organic luminescent element layer is supported between a pair of electrodes, and, if needed, a hole injection layer and electron injection layer are interposed. Stated more concretely, ones with the following layer constructions are used. (1) anode/organic luminescent layer/cathode (2) anodelhole injection layer/organic luminescent layer/cathode (3) anode/organic luminescent layerlelectron injection layer/cathode 19 (4) anode/hole injection layer/organic luminescent layer/electron injectionlayer/cathode (5) anode/hole injection layer/hole transport layer/organic luminescent layerleleciron injection layer/cathode With the above layer constructions, at least one of either the anode or the cathode is preferably transparent with respect to the wavelengh range of the light emitted fr c)m the organic luminescent body. The light is emitted through the electrode that is transparent, and the light enters the insulated fluorescent color conversion film. In this technology, it is known that it is easy to have a transparent anode, and in the present invention, the anode is preferably transparent.
For the materials for each of the above layers, known materials are used. For example, as the organic luminescent layer, in order to obtain blue to blue green luminescence, fluorescent whitening agents, such as benzothiazoles, benzimidazc les, benzoxazoles, and the like, and metal chelated oxonium compounds, styryl benzene compounds, aromatic dimethylidyne compounds, and the like are preferably used.
Referring back to Figure 2, the organic luminescent body 9 will be described in further detail. The organic luminescent body 9 is provided on top of the above described fluorescent color conversion filter 8, and comprises the following: an anode 10, which is of a transparent electrode material such as ITO and the like, a] id which is pattern formed on top of the insulated inorganic oxide film 7 which is the uppermost layer of the fluorescent color conversion filter; a hole injection layer 11 which is provided on top of anode 10; a hole transport layer 12 which is provided on top of hole injection layer 11; an organic luminescent layer 13 which is provided on top of hole transport layer 12; an electron injection layer 14 which is formed on top of organic luminescent layer 13; and a cathode 15 of a metal electrode material or the like provided on top of electron injection layer 14.
The patterns for the anode 10 and the cathode 15 are both parallel stripes, and the anode 10 and cathode 15 can be formed so that they intersect each other. In this situation, the organic luminescent element of the present invention can effect matrix driving. In other words, when voltage is applied to a specific stripe of anode 10 and a specific stripe of cathode 15, the part of organic luminescent layer 13 where these stripes intersect lights up. Therefore, by applying voltage to the selected stripes of the anode 10 and cathode 15, only the portions where the specified fluorescent color conversion film and/or filter is positioned lights up.
By having the emitted light pass through the fluorescent color conversion film and/or filter positioned in this portion, light of each of the colors is outputted through the transparent substrate 1. In other words, when a red luminescence part 16 (in other words, the portion corresponding to fluorescent color conversion film 5) lights up, this light is converted to red light by fluorescent color conversion film 5, and by further passing through red filter layer 2 and transparent substrate 1, a red light is emitted.
Furthermore, when a green luminescence part 17 (in other words, the portion corresponding to green filter layer region3) lights up, this light passes through green filter layer 3 to become only green-colored light. Part 18 corresponds to a blue luminescence part. The anode 10 can be a uniform planar electrode without any stripe patterns, and the cathode 15 can be patterned corresponding to each picture 21 element. In this situation, a switching element is provided corresponding to each picture element, and it becomes possible to effect a so-called active matrix driving.
Alternatively, the anode and cathode can be formed entirely uniformly, and the organic luminescent element of the present invention can be used as a backlight.
Below, the fluorescent color conversion film of the present invention, the fluorescent color conversion filter using this fluorescent color conversion film, and an organic luminescent element equipped with this fluorescent color conversion filter will be described in further detailed Examples. I4owever, the present invention is not lirruted to these. Various modifications are possible without departing ftorn the scope of the invention.
Example 1 The fluorescent color conversion filter shown in Figure 1 and the organic luminescent element shown in Figure 2 were manufactured as follows. Manufacture of fluorescent color conversion filter (Manufacture of the color filter layer) First, a color filter layer used in the fluorescent color conversion filter was manufactured as follows.
As the transparent substrate 1, a Coming glass (143xl 12xl lmm) was used. Afte coating a color filter red "Color mosaic CR-70OF' (product name, Fuji Hunt Electronics Technology.) on top of transparent substrate 1 by a spin coating, patteming was conducted by photolithography. Red filter layer region 2, having a 22 stripe pattern of film thickness 1 micrometer, width 0. 104 mm, spacing 0. 226 min, was obtained.
Similarly, after coating color filter green "Color mosaic CG-700 1 " (product name, Fuj i Hunt Electronics Technology) and color filter blue "Color mosaic CB-700 1 " (product name, Fuji Hunt Electronics Technology) on top of the above transparent substrate 1 by spin coating, patterning was conducted by photolithography. Green filter layer region 3 and blue filter layer region 4, each having a stripe pattern of film thickness 1 micrometer, width 0. 104 mm, spacing 0.226 mm, were obtained.
(Fluorescent color conversion filter) As the fluorescent coloring materials, cournarin 6 (0.6 weight parts), rhodamine 6G (0. 3 weight parts), and basic violet 11 (0.3 weight parts) were added to 120 weight parts of propylene glycol monoethyl acetate (PGMEA) solvent. In addition, as the molecular weight adjusting agent, 0. 3 weight parts of a compound represented by the general formula (P 1) was added and dissolved. The resulting solution was added and dissolved in 100 weight parts of a transparent light polymerizing resin M59PA/PY' (product name, Shinnittetsu Kasei Kogyo Corp. Ltd.), and a coating solution was obtained. This coating solution was coated on top of the above color filter layer by the spin coat method, and by drying in a 90 degrees C oven, a fluorescent color conversion film 5 was obtained. Furthermore, a polyvinyl alcohol was coated by spin coat on top of the laminate obtained in the previous step. This was dried, and an oxygen blocking film was formed.
Next, fluorescent color conversion film 5, which is on top of the red color filter layer region, was exposed to a light exposure device, which has a high pressure mercury 23 lamp as its light source, through a mask which achieves a stripe pattern of width 0. 104 min, spacing 0.226 min. By further developing with an alkaline solution, th stripe pattern was formed. During the developing, the oxygen blocking film was removed by rinsing with water. Next, this was heated in an 160 degrees C oven, and a fluorescent color conversion filter, in which a red filter layer region 2 of film thickness 1 micrometer and a fluorescent color conversion film 5 of film thickn4 6 micrometers were laminated on top of transparent substrate 1, was obtained.
On the top of the fluorescent color conversion filter, a UV hardening resin (ep04 modified acrylate) as protective layer 6 was coated by spin coating. This was irradiated by a high pressure mercury lamp, and protective layer 6 of film thickness 3 micrometers was formed. At this time, there was no deformation in the pattern f' the fluorescent color conversion filter, and protective layer 6 was flat. Fuilhermte, r a high temperature test was conducted at 100 degrees C, but no deformation in tl e fluorescent color conversion filter and protective layer 6 was seen. On the entire surface of protective layer 6, 30Onm Of Si02 film was deposited by the sputter method, and an insulated inorganic oxide film 7 was formed over. A fluorescen color conversion filter 8, having protective layer 6 and insulated inorganic oxide film 7, was obtained.
Manufacture of organic luminescent element On top of the fluorescent color conversion 8 shown in Figure 1 which was obtai ed by the previous steps, an organic luminescent element shown in Figure 2, whic has an organic luminescent body 9 having a six-layer construction of a sequential laminate of anode 10, hole injection layer 11, hole transport layer 12, organic 24 luminescent layer 13, electron injection layer 14, cathode 15, was manufactured as follows.
First, a transparent electrode (ITO) was formed as a film by sputter method over the entire surface of the upper surface of insulated inorganic oxide film 7, which is the topmost layer of fluorescent color conversion filter 8. After coating a resist agent "OFR.P-800" (product name, manufactured by Tokyo Oka) on top of the resulting ITO film, patterning was conducted by the photolithography method. An anode 8, which has a striped, pattern of width 0.094mm, spacing 0.016 mm, film thickness 1 0Onni positioned at the luminescent parts for each of the colors (red luminescent part 16, green luminescent part 17, blue luminescent part 18), was obtained.
Next, transparent substrate 1 on which the above anode was formed was installed inside a resistance heating vapor deposition device. Hole injection layer 11, hole transport layer 12, organic luminescent layer 13, and electron injection layer 14 were sequentially formed continuously under vacuum conditions. During film formation, the pressure inside the vacuum chamber was reduced to I x l 04Pa.
The materials and the film thicknesses for each of the layers is as follows. Referring to Table 1, the structural formulae for the materials used in each of the layers is shown. For hole injection layer 11, 10Omn of copper phthalocyanine (CuPc) was laminated. For hole transport layer 12, 20nni of 4,4-bis [N-(1-naphthyl)-Nphenylaminol biphenyl (alpha-NPD) was laminated. For organic luminescent layer 13, 30mn of 4,4'-bis(2,2'diphenylvinyl) biphenyl (DPVBi) was laminated. For electron injection layer 14, 20nm of alumi chelate (Alq) was laminated.
[00811 [Table 11
Layer construction Material name Structural formula N N N Hole injection layer Copper -Cu- N N phthalocyanine /0 N 4,4'-bis Hole transport [N-(l-naphthyl)- N N layer N-phenylaminol biphenyl 4,4'-bis(2,2 Organic diphenylvinyl) luminescent layer biphenyl tris(8-hydroxy N Electron injection quinoline) 5N layer aluminum complex 26 After laminating each layer as described above, substrate 1 was removed from the vacuum chamber. A mask, which results in striped pattern, perpendicular to the lines of anode (ITO) 10 and with a width 0.30 min, spacing 0.03mm, was attached. After again installing inside a resistance heating vapor deposition device, a cathode 15 of a Mg/Ag (10: 1 weight ratio) layer of thickness 20Onni was formed.
The organic luminescent element, obtained by the above process, was sealed inside a glove box under a dry nitrogen atmosphere using scaling glass (not shown) and UV hardening adhesive.
Example 2 A fluorescent color conversion filter was manufactured as described in Example 1, except that, instead of the molecular weight adjusting agent of Example 1, 0.3 weight parts of a compound represented by chemical formula (P3) was used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Example 3 A fluorescent color conversion filter was manufactured as described in Example 1, except that, instead of the molecular weight adjusting agent of Example 1, 0.3 weight parts of a compound represented by chemical formula (P6) was used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
27 Example 4 A fluorescent color conversion filter was manufactured as described in Example 1, except that, instead of the molecular weight adjusting agent of Example 1, 0.5 weight parts of a compound represented by chemical formula (P7) was used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Example 5 A fluorescent color conversion filter was manufactured as described in Example i, except that, instead of the molecular weight adjusting agent of Example 1, 0.3 weight parts of a compound represented by chemical formula (P 10) was used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Example 6 A fluorescent color conversion filter was manufactured as described in Example 1, except that, instead of the molecular weight adjusting agent of Example 1, 0.3 weight parts of a compound represented by chemical formula (P 11) was used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Example 7 A fluorescent color conversion filter was manufactured as described in Example 1, except that, instead of the molecular weight adjusting agent of Example 1, 0.3 weight parts of a compound represented by chemical formula (P12) was used. 1 28 addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Comparative Example 1 A fluorescent color conversion filter, which does not contain the molecular weight adjusting agent, was manufactured as described in Example, except that the molecular weight adjusting agent of Example 1 was not used. In addition, an organic luminescent element equipped with this fluorescent color conversion filter was manufactured.
Evaluation of organic luminescent element) The organic luminescent elements obtained in Examples 1 to 7, and Comparative Example 1 were evaluated as follows. The evaluation results are shown in Table 2.
CIE color coordinates For the CIE color coordinates, the color is represented by three values of Y, x, y using a chromaticity diagram. Y represents reflectance (corresponds to brightness), x and y are coordinates (chromaticity) of the color. They were measured using MCPD1000 (manufactured by Otsuka Denshi).
Relative conversion efficiency For the relative conversion efficiency, the organic luminescent element with the fluorescent color conversion filter of Example 1 was lit, and the voltage at which the luminance became 50 cd/M2 was made the standard voltage. The luminance obtained by applying the standard voltage to each of the organic luminescent 29 elements was measured. The relative conversion efficiency was compared, with Example 1 having a luminance of 1.
Table 2
CIE Color coordinates Relative color conversiot X y efficiency Example 1 0.64 0.34 1 Example 2 0.64 0.34 1.01 Example 3 0.65 0.33 0.98 Example 4 0.64 0.33 1.05 Example 5 0.65 0.34 0.92 Example 6 0.65 0.34 0.95 Example 7 0.64 0.33 0.97 Comparative Example 1 0.61 0.36 0.64 The organic luminescent elements obtained in Example s 1 to 7 (the fluorescent color conversion film used in the fluorescent color conversion filter contain molecular weight adjusting agents) resulted in red luminescence with a high colcr purity and a high relative conversion efficiency. In contrast, with the organic luminescent element obtained in Comparative Example 1 (no molecular weight adjusting agent), it is clear that the red purity is reduced and the relative conversion efficiency is reduced.
As described above, according to the present invention, light from the near ultraviolet range to the visible range emitted from a luminescent body is absorbed and efficiently converted into a different visible light (for example, red light and the like). In addition, a fluorescent color conversion filter in which high detail patterning is possible can be obtained easily and inexpensively. Furthermore, because the organic luminescent element equipped with this fluorescent color conversion filter has excellent light emitting efficiency, it can be suitably used for personal and industrial display devices, such as luminescent multicolor or full color displays, display panels, backlights, and the like. In addition, using this fluorescent color conversion filter, the manufacture of full color organic luminescent element display which can be driven by low voltage can be realized.
31
Claims (6)
1. A fluorescent color conversion film, comprising at least one organic fluorescent coloring material which is capable of absorbing light obtained from a luminescent body in the near ultraviolet to the visible range and of emitting visible light of a different wavelength; at least one molecular weight adjusting agent; and at least one matrix resin which supports said organic fluorescent coloring material and said molecular weight adjusting agent, wherein said molecular weight adjusting agent contains at least one compound represented by the following general formua CH2 B A---- C wherein each of A and B is independently selected from a substituted aromatic group, an unsubstituted aromatic group, a substituted heterocyclic group and an unsubstituted heterocyclic group.
2. A fluorescent color conversion film as claimed in Claim 1, wherein, based on the weight of said fluorescent color conversion film, the content of said at least one molecular weight adjusting agent in said fluorescent color conversion fi lm is in the range of 0.01 to 5 weight %. i
3. A fluorescent color conversion film as claimed Mi claim 1 or 2, wherein so id at least one molecular weight adjusting agent is selected from:- 32 c (m) H2C=C\,--,,- U_ a CH3 (P2) H2C=C \a CH3 0 C2H5 (P3) H2C=C CL C2H5 Cer OCH3 (P4) H2C= 1: 1 OCH3 33 0C2H5 (P5) H2C=C H2C=C OH(P6) cl (P7) H2C=C cl H2C=C CLCH3 (1-9) H2C=C 34 1. (I-10) /01oo H2C=C S H2C=C C2H5 (P12) H2C=C H N CH3
4. A fluorescent color conversion film as claimed in claim 1, substantially as hereinbefore described in any one of Examples 1 to 7.
5. A fluorescent color conversion filter, comprising a fluorescent color conversion film as claimed in any one of claims 1 to 4, and a substrate which supports said fluorescent color conversion film.
6. An organic luminescent element, comprising at least one fluorescent color conversion filter as claimed in claim 5, and at least one organic luminescent body which is capable of emitting light entering into said fluorescent color conversion filter.
36
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30315299A JP3456638B2 (en) | 1999-10-25 | 1999-10-25 | Fluorescent color conversion film, fluorescent color conversion film filter using the fluorescent color conversion film, and organic light emitting device including the fluorescent color conversion film filter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0026062D0 GB0026062D0 (en) | 2000-12-13 |
| GB2357889A true GB2357889A (en) | 2001-07-04 |
Family
ID=17917515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0026062A Withdrawn GB2357889A (en) | 1999-10-25 | 2000-10-25 | Fluorescent colour conversion film |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP3456638B2 (en) |
| GB (1) | GB2357889A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003020846A1 (en) * | 2001-08-30 | 2003-03-13 | Idemitsu Kosan Co., Ltd. | Color-changing material composition and color-changing membranes made by using the same |
| GB2412662A (en) * | 2004-04-01 | 2005-10-05 | Fuji Electric Holdings | Method of manufacturing color-converting filter |
| US7294439B2 (en) | 2003-04-01 | 2007-11-13 | Fuji Electric Holdings Co., Ltd. | Color-converting filter and manufacturing method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112006003096T5 (en) * | 2005-11-11 | 2008-10-23 | Fuji Electric Holdings Co., Ltd. | Organic EL light emission display |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004304A1 (en) * | 1986-12-05 | 1988-06-16 | Commonwealth Scientific And Industrial Research Or | Control of molecular weight and end group functionality of polymers |
| WO1991006535A1 (en) * | 1989-11-01 | 1991-05-16 | Commonwealth Scientific And Industrial Research Organisation | Control of molecular weight and end group functionality in polymers using unsaturated peroxy compounds as chain transfer agents |
| JPH083208A (en) * | 1994-06-20 | 1996-01-09 | Nippon Steel Chem Co Ltd | Molecular weight modifier |
| JPH09208944A (en) * | 1996-02-06 | 1997-08-12 | Idemitsu Kosan Co Ltd | Fluorescent transducing membrane |
-
1999
- 1999-10-25 JP JP30315299A patent/JP3456638B2/en not_active Expired - Lifetime
-
2000
- 2000-10-25 GB GB0026062A patent/GB2357889A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988004304A1 (en) * | 1986-12-05 | 1988-06-16 | Commonwealth Scientific And Industrial Research Or | Control of molecular weight and end group functionality of polymers |
| WO1991006535A1 (en) * | 1989-11-01 | 1991-05-16 | Commonwealth Scientific And Industrial Research Organisation | Control of molecular weight and end group functionality in polymers using unsaturated peroxy compounds as chain transfer agents |
| JPH083208A (en) * | 1994-06-20 | 1996-01-09 | Nippon Steel Chem Co Ltd | Molecular weight modifier |
| JPH09208944A (en) * | 1996-02-06 | 1997-08-12 | Idemitsu Kosan Co Ltd | Fluorescent transducing membrane |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003020846A1 (en) * | 2001-08-30 | 2003-03-13 | Idemitsu Kosan Co., Ltd. | Color-changing material composition and color-changing membranes made by using the same |
| US7294439B2 (en) | 2003-04-01 | 2007-11-13 | Fuji Electric Holdings Co., Ltd. | Color-converting filter and manufacturing method |
| GB2412662A (en) * | 2004-04-01 | 2005-10-05 | Fuji Electric Holdings | Method of manufacturing color-converting filter |
| GB2412662B (en) * | 2004-04-01 | 2009-07-22 | Fuji Electric Holdings Co | Method of manufacturing color-converting filter |
| GB2456685A (en) * | 2004-04-01 | 2009-07-29 | Fuji Electric Holdings Co | Colour-converting filter |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0026062D0 (en) | 2000-12-13 |
| JP3456638B2 (en) | 2003-10-14 |
| JP2001126870A (en) | 2001-05-11 |
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