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WO2016098570A1 - Élément électroluminescent organique, composition de résine durcissable, procédé de formation d'unité de conversion de longueur d'onde, et dispositif électroluminescent organique - Google Patents

Élément électroluminescent organique, composition de résine durcissable, procédé de formation d'unité de conversion de longueur d'onde, et dispositif électroluminescent organique Download PDF

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Publication number
WO2016098570A1
WO2016098570A1 PCT/JP2015/083636 JP2015083636W WO2016098570A1 WO 2016098570 A1 WO2016098570 A1 WO 2016098570A1 JP 2015083636 W JP2015083636 W JP 2015083636W WO 2016098570 A1 WO2016098570 A1 WO 2016098570A1
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Prior art keywords
organic
wavelength conversion
group
resin composition
curable resin
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English (en)
Japanese (ja)
Inventor
英行 神井
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JSR Corp
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JSR Corp
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Priority to JP2016564767A priority patent/JPWO2016098570A1/ja
Publication of WO2016098570A1 publication Critical patent/WO2016098570A1/fr
Anticipated expiration legal-status Critical
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass

Definitions

  • the present invention relates to an organic EL element, a curable resin composition, a method for forming a wavelength conversion unit, and an organic EL device.
  • the extremely small particles (dots) that can confine electrons three-dimensionally are called quantum dots and have attracted attention in recent years.
  • the size of one quantum dot is several nanometers (nm) to several tens of nanometers (nm) in diameter.
  • a wavelength conversion (color conversion) part including quantum dots as a wavelength conversion material When a wavelength conversion (color conversion) part including quantum dots as a wavelength conversion material is applied to, for example, an organic EL element, it is required to realize excellent luminance characteristics. Therefore, for example, it is desired to increase the content of quantum dots in the wavelength conversion section formed in a layered or film shape.
  • a wavelength conversion unit including quantum dots there is a problem that patterning properties are deteriorated.
  • a display device when a display device is configured using an organic EL element, it is required to form a wavelength conversion unit having a size corresponding to a display pixel size or pattern the wavelength conversion unit in a stripe shape having a desired size.
  • an object of the present invention is to provide an organic EL element that has a wavelength conversion unit including quantum dots, suppresses a decrease in patterning property, and easily increases luminance.
  • Another object of the present invention is to provide a curable resin composition that includes a quantum dot and provides a wavelength conversion part of an organic EL device by forming a cured film that exhibits excellent fluorescence characteristics and patterning properties. is there.
  • Still another object of the present invention is to provide a method for forming a wavelength conversion part that forms a wavelength conversion part having excellent fluorescence characteristics at a desired location of an organic EL element.
  • Still another object of the present invention is to provide an organic EL device that can easily display an image with high luminance and excellent image quality.
  • a first aspect of the present invention is an organic EL element having a light emitting part and a wavelength converting part
  • the wavelength converter is [A] a polymer having (a1) a structural unit containing an acidic group and (a2) a structural unit containing an organic group having 4 to 20 carbon atoms other than (a1) in the same or different polymer molecules
  • [B] The present invention relates to an organic EL device characterized by being formed using a curable resin composition containing quantum dots.
  • the [B] quantum dot is at least selected from the group consisting of a group 2 element, a group 11 element, a group 12 element, a group 13 element, a group 14 element, a group 15 element and a group 16 element. It is preferably made of a compound containing two kinds of elements.
  • the [B] quantum dot is made of a compound containing In as a constituent component.
  • the [B] quantum dot comprises an InP / ZnS compound, a CuInS 2 / ZnS compound, an AgInS 2 compound, a (ZnS / AgInS 2 ) solid solution / ZnS compound, a Zn-doped AgInS 2 compound, and an Si compound. It is preferably at least one selected from the group consisting of:
  • the second aspect of the present invention is: [A] a polymer having (a1) a structural unit containing an acidic group and (a2) a structural unit containing an organic group having 4 to 20 carbon atoms in the same or different polymer molecules, and [B] a quantum dot A curable resin composition containing,
  • the present invention relates to a curable resin composition that is used for forming the wavelength conversion part of the organic EL device according to the first aspect of the present invention.
  • the [B] quantum dot is at least selected from the group consisting of a group 2 element, a group 11 element, a group 12 element, a group 13 element, a group 14 element, a group 15 element and a group 16 element. It is preferably made of a compound containing two kinds of elements.
  • the [B] quantum dot is made of a compound containing In as a constituent component.
  • the [B] quantum dot comprises an InP / ZnS compound, a CuInS 2 / ZnS compound, an AgInS 2 compound, a (ZnS / AgInS 2 ) solid solution / ZnS compound, a Zn-doped AgInS 2 compound, and an Si compound. It is preferably at least one selected from the group consisting of:
  • a third aspect of the present invention is a method of forming a wavelength conversion unit that forms the wavelength conversion unit of an organic EL element having a light source unit that emits light containing at least blue light and a wavelength conversion unit, (1) The process of forming the coating film of the curable resin composition of the 2nd aspect of this invention on a base material, (2) A step of irradiating at least a part of the coating film formed in step (1), (3) The step of developing the coating film irradiated with radiation in the step (2), and (4) The step of exposing the coating film developed in the step (3). Regarding the method.
  • the fourth aspect of the present invention relates to an organic EL device comprising the organic EL element of the first aspect of the present invention and used for image display.
  • an organic EL element that has a wavelength conversion unit including quantum dots and suppresses a decrease in patterning property and easily increases luminance.
  • a curable resin composition that provides a wavelength conversion part of an organic EL element by forming a cured film that includes quantum dots and exhibits excellent fluorescence characteristics and patterning properties. Is done.
  • a method for forming a wavelength conversion unit that forms a wavelength conversion unit with excellent fluorescence characteristics at a desired location of an organic EL element.
  • an organic EL device that can easily display an image with high luminance and excellent image quality.
  • FIG. 1 is a cross-sectional view schematically showing an organic EL element according to a first embodiment of the present invention. It is sectional drawing which shows schematically the organic EL element of 2nd Embodiment of this invention. It is sectional drawing of the base material explaining an example of the coating-film formation process in the formation method of the wavelength conversion part of 4th Embodiment of this invention. It is sectional drawing which illustrates typically an example of the radiation irradiation process in the formation method of the wavelength conversion part of 4th Embodiment of this invention. It is sectional drawing of the board
  • FIG. 1 is a cross-sectional view schematically showing an organic EL element according to the first embodiment of the present invention.
  • An organic EL element 100 shown in FIG. 1 includes a circuit substrate 10 that is a substrate on which a pixel circuit is formed, a second planarization film 20 formed on the circuit substrate 10, and a plurality of rows on the second planarization film 20.
  • An organic EL element array 30 composed of a plurality of organic EL portions 31 arranged over a plurality of rows, a passivation layer 40 formed on the organic EL element array 30, and a wavelength conversion member 50 arranged on the passivation layer 40.
  • An active matrix image display device is a circuit substrate 10 that is a substrate on which a pixel circuit is formed, a second planarization film 20 formed on the circuit substrate 10, and a plurality of rows on the second planarization film 20.
  • An organic EL element array 30 composed of a plurality of organic EL portions 31 arranged over a plurality of rows, a passivation layer 40 formed on the organic EL element array 30, and a wavelength conversion member 50 arranged on the passivation layer 40.
  • the organic EL element array 30 is a light emitting unit in the organic EL element 100 according to the first embodiment of the present invention, and constitutes a light source unit that emits light including at least blue light.
  • the wavelength conversion member 50 is a light emitting part and is disposed opposite to the organic EL part 31 of the organic EL element array 30 serving as a light source, and converts the wavelength of light from the organic EL part 31.
  • a conversion part it has red wavelength conversion layer 53R, green wavelength conversion layer 53G, and blue wavelength conversion layer 53B.
  • Each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B of the wavelength conversion member 50 is configured to contain quantum dots.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B of the wavelength conversion member 50 each contain a quantum dot, and each serves as a wavelength conversion unit.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B are disposed to face the organic EL unit 31, and convert light from the organic EL unit 31 into red light, green light, or blue light. be able to. Therefore, the organic EL element 100 can form a color image and perform color display by controlling the amount of red light, green light, and blue light emitted from the wavelength conversion member 50.
  • the circuit board 10 has a plurality of pixel circuits formed on a substrate 11 made of glass or resin through a buffer layer 12 made of, for example, spin-on-glass (SOG).
  • each pixel circuit one switching circuit is formed for each of the plurality of organic EL units 31 constituting the organic EL element array 30, and these switching circuits are arranged in a plurality of rows and a plurality of columns in plan view. They are arranged in a matrix.
  • Each switching circuit includes one thin film transistor for selection (hereinafter, the thin film transistor is abbreviated as “TFT”), one driving TFT, and a pair of capacitor (holding capacitor) electrodes.
  • TFT thin film transistor for selection
  • FIG. 1 a total of four selection TFTs 15 and one capacitor electrode 16 in each of the four pairs of capacitor electrodes appear, and the other capacitor electrode in each of the driving TFTs and the total of four pairs of capacitor electrodes appears. Absent.
  • each selection TFT 15 The source 13 s and the drain 13 d in each selection TFT 15 are formed in the silicon layer 13 formed on the buffer layer 12, and the gate 14 in these selection TFT 15 is a gate insulating film (not shown) on the silicon layer 13. ).
  • the source 13s of each selection TFT 15 constituting one row is connected to the data line 19 by a contact plug 17a, and the drain 13d of each of these selection TFTs 15 is connected to the data line 19 by a contact plug 17b. At the same time, it is connected to the gate of the corresponding driving TFT and one capacitor electrode 16 of the corresponding pair of capacitor electrodes.
  • the gates 14 of these selection TFTs 15 are connected to one selection line (none is shown) by contact plugs.
  • each driving TFT constituting one column is connected to one power supply line, and the drain of each of these driving TFTs is connected to the pixel electrode 31a of the corresponding organic EL section 31 and a corresponding pair.
  • the capacitor electrode is connected to the other capacitor electrode.
  • Each selection TFT 15 and each driving TFT are covered with, for example, a first planarization film 18 formed of an inorganic material.
  • the data line 19 is formed on the first planarization film 18.
  • the selection line and the power supply line are formed on the buffer layer 12 and covered with the first planarization film 18.
  • the second planarization film 20 is formed of an inorganic material or an organic material and covers the data line 19.
  • the organic EL element array 30 has a plurality of organic EL portions 31 arranged in a plurality of rows and columns, and a lattice shape so as to surround each organic EL portion 31 when the organic EL element array 30 is viewed in plan view. And a partition wall portion 32 formed on the surface.
  • Each organic EL unit 31 includes a pixel electrode 31a disposed on the second planarization film 20, an organic light emitting layer 31b stacked on the pixel electrode 31a, an upper surface of each organic light emitting layer 31b, and an upper portion of the partition wall 32. And a region on the organic light emitting layer 31b in one common electrode 31c covering the same.
  • These organic EL portions 31 are top emission type light emitting elements that emit white light from the common electrode 31c side.
  • the individual organic light emitting layers 31b are, for example, a red organic light emitting layer that emits red light, a green organic light emitting layer that emits green light, and a blue organic light emitting layer that emits blue light in any order and adjacent in the vertical direction. It can be formed by sequentially laminating on the pixel electrode 31a with the charge generation layer interposed between the organic light emitting layers. Alternatively, the yellow organic light emitting layer that emits yellow light and the blue organic light emitting layer are arranged in any order, and the charge generation layer is interposed between the yellow organic light emitting layer and the blue organic light emitting layer, and sequentially on the pixel electrode 31a. It can be formed by stacking. The organic light emitting layer 31b can emit white light by combining the light from each color organic light emitting layer by the above stacking.
  • the partition wall 32 of the organic EL element array 30 is cured by, for example, patterning the resin layer after forming the resin layer, or applying the resin material to a predetermined shape by an ink jet method or a printing method. Can be formed.
  • the passivation layer 40 is formed of, for example, a transparent organic material and covers the common electrode 31c.
  • the wavelength conversion member 50 includes a substrate 51 formed using a transparent inorganic material or a transparent organic material, and a red color filter 52R, a green color filter 52G, and a blue color filter 52B regularly arranged on the substrate 51.
  • the red color filter 52R, the green color filter 52G, and the blue color filter 52B constitute a color filter in the organic EL element 100. That is, the color filter included in the organic EL element 100 includes the red color filter 52R, the green color filter 52G, and the blue color filter 52B.
  • the substrate 51 is made of, for example, glass, quartz, or transparent resin (for example, transparent polyimide, polyethylene naphthalate, polyethylene terephthalate, polyester film, cyclic olefin resin film, etc.).
  • Each of the red color filter 52R, the green color filter 52G, and the blue color filter 52B is formed of a resin material colored in red, green, or blue according to a known method. For example, a stripe pattern, a mosaic pattern, It is arranged under a desired pattern such as a Bayer pattern.
  • the wavelength conversion member 50 includes a red wavelength conversion layer 53R formed on the red color filter 52R when viewed from the substrate 51, a green wavelength conversion layer 53G formed on the green color filter 52G, and a blue color filter 52B. And a blue wavelength conversion layer 53B formed on the substrate.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B are cured films formed by using the curable resin composition of the third embodiment of the present invention described later, each containing quantum dots. Configured.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B each include, for example, light in a predetermined wavelength range such as blue light contained in white light from the organic EL unit 31 in red.
  • the wavelength conversion unit converts light, green light, or blue light.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B may be collectively referred to as wavelength conversion layers 53R, 53G, and 53B.
  • the red wavelength conversion layer 53R emits red fluorescence when irradiated with excitation light, specifically, excitation light from the organic EL unit 31. That is, the red wavelength conversion layer 53R converts light from the organic EL unit 31 into red light.
  • the green wavelength conversion layer 53G emits green fluorescence when irradiated with excitation light. That is, the green wavelength conversion layer 53G converts light from the organic EL unit 31 into green light.
  • the blue wavelength conversion layer 53B emits blue fluorescence when irradiated with excitation light. That is, the blue wavelength conversion layer 53B converts light from the organic EL unit 31 into blue light.
  • the thicknesses of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B of the wavelength conversion member 50 are each preferably about 100 nm to 100 ⁇ m, and more preferably 1 ⁇ m to 100 ⁇ m. If the thickness is less than 100 nm, the excitation light cannot be sufficiently absorbed, and the light conversion efficiency is lowered, so that there is a problem that the luminance of the display element cannot be sufficiently secured. Furthermore, in order to increase the absorption of excitation light and sufficiently secure the luminance of the display element, the thickness is preferably 1 ⁇ m or more.
  • Each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B has substantially the same size as one organic EL unit 31 or one organic EL unit 31 in plan view.
  • One wavelength conversion layer 53R, 53G, 53B is located above one organic EL unit 31.
  • the organic EL unit 31 and each of the wavelength conversion layers 53R, 53G, and 53B having the same size are disposed to face each other, and convert light from the organic EL unit 31 into red light, green light, or blue light. .
  • the organic EL unit 31 corresponding to each of the wavelength conversion layers 53R, 53G, and 53B is viewed in plan from the wavelength conversion layer 53R, 53G, and 53B side, the organic EL unit 31 includes the corresponding wavelength conversion layer 53R. , 53G, 53B does not substantially protrude outward.
  • the wavelength conversion layers 53R, 53G, and 53B corresponding to the color filters 52R, 52G, and 52B are viewed in plan from the color filter side, the wavelength conversion layers 53R, 53G, and 53B correspond to the color filters. It does not substantially protrude outward from 52R, 52G, and 52B.
  • the color filter is provided on the anti-organic EL element side of the wavelength conversion layers 53R, 53G, and 53B disposed to face the organic EL unit 31. That is, the color filter is provided above the wavelength conversion unit, and is disposed on the side opposite to the side on which the light source unit including the organic EL unit 31 is disposed with the wavelength conversion unit interposed therebetween.
  • the wavelength conversion member 50 has a black matrix 54 formed on the substrate 51 by an inorganic material or an organic material having a light shielding property.
  • the black matrix 54 surrounds the color filters 52R, 52G, and 52B and also surrounds the wavelength conversion layers 53R, 53G, and 53B in plan view.
  • the black matrix 54 can be formed by patterning according to a known method using a known light-shielding material. Note that the black matrix 54 is not an essential component in the wavelength conversion member 50, and the wavelength conversion member 50 may be configured without the black matrix 54.
  • the wavelength conversion member 50 is bonded onto the passivation layer 40 after the wavelength conversion member 50 is formed alone, for example.
  • the color conversion layers 53R, 53G, and 53B, the color filters 52R, 52G, and 52B, and the black matrix 54 are sequentially formed on the passivation layer 40, and then the color filters 52R, 52G, and 52B, and the black matrix 54, respectively. It can be formed by bonding the substrate 51 on the upper surface of the substrate.
  • the white light from the organic EL element array 30 is used as excitation light, and the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B of the wavelength conversion member 50 respectively Excitation light can be converted into red light, green light, and blue light. Further, the organic EL element 100 converts the red light, the green light, and the blue light emitted from each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B of the wavelength conversion member 50 into each color. High color purity can be achieved by transmitting the filters 52R, 52G, and 52B.
  • the organic EL element 100 Furthermore, in the organic EL element 100, light from the organic EL unit 31 of the organic EL element array 30 passes through the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, or the blue wavelength conversion layer 53B, and is not wavelength-converted. When emitted, each of the color filters 52R, 52G, and 52B of the wavelength conversion member 50 is used so that the wavelength characteristics of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue wavelength conversion layer 53B are assisted. Adjustments can be made. And in the organic EL element 100, it can reduce that the light of an undesired color is radiate
  • each of the wavelength conversion layers 53R, 53G, and 53B containing quantum dots is formed by the curable resin composition of the third embodiment of the present invention described later. Yes. For this reason, each of the wavelength conversion layers 53R, 53G, and 53B exhibits excellent fluorescence characteristics, specifically, wavelength conversion efficiency due to the inclusion of quantum dots. Further, since it is difficult for a residue to occur when each of the wavelength conversion layers 53R, 53G, and 53B is formed, color mixing between pixels due to the occurrence of the residue of the wavelength conversion layers 53R, 53G, and 53B in an undesired portion is also unlikely to occur. . As a result of these, the organic EL element 100 can be used for the configuration of an organic EL device that can easily increase the luminance, and can display an image with high luminance and high image quality.
  • FIG. 2 is a cross-sectional view schematically showing an organic EL element according to the second embodiment of the present invention.
  • the organic EL element 200 of the second embodiment shown in FIG. 2 uses blue light as excitation light, and the wavelength conversion member 150 includes a red wavelength conversion layer 53R, a green wavelength conversion layer 53G, and a blue diffusion layer 151, except that It has the same structure as the organic EL element 100 of one embodiment. Therefore, in the organic EL element 200 of the second embodiment shown in FIG. 2, the same reference numerals are given to the same constituent elements as those of the organic EL element 100 of FIG.
  • An organic EL element 200 shown in FIG. 2 includes a circuit substrate 10 on which a pixel circuit is formed, a second planarization film 20 formed on the circuit substrate 10, and a plurality of rows and columns on the second planarization film 20.
  • An organic EL element array 130 composed of a plurality of organic EL portions 131 arranged over the organic EL element 131, a passivation layer 40 formed on the organic EL element array 130, and a wavelength conversion member 150 disposed on the passivation layer 40. This is an active matrix drive type image display element.
  • the organic EL part 131 of the organic EL element array 130 can emit blue light as will be described later. That is, the organic EL element array 130 is a light emitting unit in the organic EL element 200 of the second embodiment of the present invention, and constitutes a light source unit that emits blue light.
  • the wavelength conversion member 150 is a light emitting part and is disposed opposite to the organic EL part 131 of the organic EL element array 130 serving as a light source, and converts the wavelength of light from the organic EL part 131.
  • the wavelength conversion member 150 has red wavelength conversion layer 53R and green wavelength conversion layer 53G.
  • the wavelength conversion member 150 includes a blue diffusion layer 151 as a light diffusion layer that is disposed opposite to the organic EL unit 131 and diffuses and emits light from the organic EL unit 131.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G of the wavelength conversion member 150 are each configured to contain quantum dots. That is, in the organic EL element 200, the red wavelength conversion layer 53R and the green wavelength conversion layer 53G of the wavelength conversion member 150 each contain a quantum dot, and each serves as a wavelength conversion unit.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G are disposed to face the organic EL unit 131, and can convert blue light from the organic EL unit 131 into red light or green light.
  • the blue diffusion layer 151 of the wavelength conversion member 150 can diffuse and emit the blue light from the organic EL unit 131 with the same wavelength (color) characteristics without converting the wavelength. Therefore, the organic EL element 200 can form a color image and perform color display by controlling the amount of red light, green light, and blue light emitted from the wavelength conversion member 150.
  • the circuit board 10 has a plurality of pixel circuits formed on a substrate 11 made of glass or resin through a buffer layer 12 made of, for example, spin-on-glass (SOG).
  • each pixel circuit one switching circuit is formed for each of the plurality of organic EL units 131 constituting the organic EL element array 130, and these switching circuits are arranged in a plurality of rows and a plurality of columns in plan view. They are arranged in a matrix.
  • Each switching circuit includes one thin film transistor for selection (hereinafter, the thin film transistor is abbreviated as “TFT”), one driving TFT, and a pair of capacitor (holding capacitor) electrodes.
  • TFT thin film transistor for selection
  • FIG. 2 a total of four selection TFTs 15 and one capacitor electrode 16 in each of the four pairs of capacitor electrodes appear, and the other capacitor electrode in each of the driving TFTs and the total of four pairs of capacitor electrodes appears. Absent.
  • each selection TFT 15 The source 13 s and the drain 13 d in each selection TFT 15 are formed in the silicon layer 13 formed on the buffer layer 12, and the gate 14 in these selection TFT 15 is a gate insulating film (not shown) on the silicon layer 13. ).
  • the source 13s of each selection TFT 15 constituting one row is connected to the data line 19 by a contact plug 17a, and the drain 13d of each of these selection TFTs 15 is connected to the data line 19 by a contact plug 17b. At the same time, it is connected to the gate of the corresponding driving TFT and one capacitor electrode 16 of the corresponding pair of capacitor electrodes.
  • the gates 14 of these selection TFTs 15 are connected to one selection line (none is shown) by contact plugs.
  • each driving TFT constituting one column is connected to one power supply line, and the drain of each of these driving TFTs is connected to the pixel electrode 31a of the corresponding organic EL unit 131 and the corresponding pair of pixels.
  • the capacitor electrode is connected to the other capacitor electrode.
  • Each selection TFT 15 and each driving TFT are covered with, for example, a first planarization film 18 formed of an inorganic material.
  • the data line 19 is formed on the first planarization film 18.
  • the selection line and the power supply line are formed on the buffer layer 12 and covered with the first planarization film 18.
  • the second planarization film 20 is formed of an inorganic material or an organic material and covers the data line 19.
  • the organic EL element array 130 includes a plurality of organic EL units 131 arranged in a plurality of rows and columns, and a lattice shape so as to surround each organic EL unit 131 when the organic EL element array 130 is viewed in plan view. And a partition wall portion 32 formed on the surface.
  • Each organic EL portion 131 includes a pixel electrode 31a disposed on the second planarizing film 20, an organic light emitting layer 131b stacked on the pixel electrode 31a, an upper surface of each organic light emitting layer 131b, and an upper portion of the partition wall portion 32. And a region on the organic light emitting layer 131b in one common electrode 31c covering the same.
  • These organic EL portions 131 are top emission type light emitting elements that emit white light from the common electrode 31c side.
  • Each organic light emitting layer 131b can be formed by laminating a blue organic light emitting layer emitting blue light on the pixel electrode 31a.
  • the partition wall 32 can be formed, for example, by patterning the resin layer after forming the resin layer, or by curing the resin material after applying the resin material to a predetermined shape by an ink jet method or a printing method.
  • the passivation layer 40 is formed of, for example, a transparent organic material and covers the common electrode 31c.
  • the wavelength conversion member 150 includes a substrate 51 formed using a transparent inorganic material or a transparent organic material, and a red color filter 52R, a green color filter 52G, and a blue color filter 52B regularly arranged on the substrate 51.
  • the red color filter 52R, the green color filter 52G, and the blue color filter 52B constitute a color filter in the organic EL element 200. That is, the color filter of the organic EL element 200 includes a red color filter 52R, a green color filter 52G, and a blue color filter 52B.
  • the substrate 51 is made of glass, quartz, or transparent resin (for example, transparent polyimide, polyethylene naphthalate, polyethylene terephthalate, polyester film, cyclic olefin resin film, etc.).
  • Each of the red color filter 52R, the green color filter 52G, and the blue color filter 52B is formed of a resin material colored in red, green, or blue according to a known method. For example, a stripe pattern, a mosaic pattern, It is arranged under a desired pattern such as a Bayer pattern.
  • the wavelength conversion member 150 includes a red wavelength conversion layer 53R formed on the red color filter 52R when viewed from the substrate 51, a green wavelength conversion layer 53G formed on the green color filter 52G, and a blue color filter 52B. And a blue diffusion layer 151 formed on the substrate.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G of the wavelength conversion member 150 are cured films formed using the curable resin composition of the third embodiment to be described later, and are each configured to contain quantum dots.
  • the blue diffusion layer 151 can be formed, for example, by dispersing light scattering particles in a resin serving as a base material.
  • the red wavelength conversion layer 53R of the wavelength conversion member 150 When the red wavelength conversion layer 53R of the wavelength conversion member 150 is irradiated with excitation light, specifically, excitation light (blue light) from the organic EL unit 131, the wavelength is converted to red fluorescence.
  • the green wavelength conversion layer 53G When the green wavelength conversion layer 53G is irradiated with excitation light (blue light), the green wavelength conversion layer 53G converts the wavelength and emits green fluorescence.
  • the blue diffusion layer 151 can diffuse and emit the blue light when receiving the blue light from the organic EL unit 131.
  • each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151 of the wavelength conversion member 150 is preferably about 100 nm to 100 ⁇ m, and more preferably 1 ⁇ m to 100 ⁇ m.
  • the thickness of the red wavelength conversion layer 53R and the green wavelength conversion layer 53G is less than 100 nm, the excitation light cannot be sufficiently absorbed, and the light conversion efficiency is lowered, so that the luminance of the display element cannot be sufficiently secured. Problems arise.
  • the blue diffusion layer 151 preferably has a thickness in the above range so that the blue light from the organic EL element 131 can be efficiently diffused and emitted.
  • Each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151 is substantially the same size as one organic EL unit 131 in plan view, or from one organic EL unit 131. Also, one wavelength conversion layer 53R, 53G or blue diffusion layer 151 is located above one organic EL unit 131. That is, the organic EL unit 131 and the wavelength conversion layers 53R and 53G having the same size as each other are arranged to face each other and convert the wavelength of blue light from the organic EL unit 131.
  • the organic EL unit 131 and the blue diffusion layer 151 having the same size are disposed so as to diffuse the blue light from the organic EL unit 131.
  • the blue diffusion layer 151 is preferably configured by dispersing transparent particles serving as light scattering particles in a resin component.
  • the resin used for the blue diffusion layer 151 a conventionally known resin can be used, and is not particularly limited, but a resin having light transmittance is preferable. And in the curable resin composition of 3rd Embodiment mentioned later, it replaces with a quantum dot and it is preferable to add and disperse
  • the transparent particles contained in the blue diffusion layer 151 are not particularly limited as long as they can scatter and transmit light from the organic EL part 131.
  • the average particle diameter is 25 ⁇ m, and the standard deviation of the particle size distribution is 1 ⁇ m.
  • Polystyrene particles or the like can be used.
  • the content of the transparent particles in the blue diffusion layer 151 can be appropriately changed and is not particularly limited.
  • the organic EL unit 131 corresponds to the corresponding red color.
  • the wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151 do not substantially protrude outward.
  • the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151 corresponding to each of the color filters 52R, 52G, and 52B are viewed in plan from the color filter side, the red wavelength conversion layer 53R, The green wavelength conversion layer 53G and the blue diffusion layer 151 do not substantially protrude outward from the color filters 52R, 52G, and 52B.
  • the color filter is provided on the anti-organic EL element side of each of the wavelength conversion layers 53 ⁇ / b> R and 53 ⁇ / b> G and the blue diffusion layer 151 disposed to face the organic EL unit 131. That is, the color filter is provided above the wavelength conversion unit, and is disposed on the side opposite to the side on which the light source unit including the organic EL unit 131 is disposed with the wavelength conversion unit interposed therebetween.
  • the wavelength conversion member 150 has a black matrix 54 formed on the substrate 51 with a light-shielding inorganic material or organic material.
  • the black matrix 54 surrounds the color filters 52R, 52G, and 52B in plan view, and also surrounds the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151.
  • the black matrix 54 can be formed by patterning according to a known method using a known light-shielding material. Note that the black matrix 54 is not an essential component in the wavelength conversion member 150, and the wavelength conversion member 150 may be configured without the black matrix 54.
  • the wavelength conversion member 150 is bonded onto the passivation layer 40 after the wavelength conversion member 150 is formed alone.
  • the color filters 52R, 52G, and 52B and the black matrix 54 are sequentially formed on the passivation layer 40, the color filters 52R and 52G are formed.
  • 52B and the black matrix 54 can be formed by bonding the substrate 51 on the upper surface.
  • the blue light from the organic EL element array 130 is used as excitation light, and the excitation light is converted into red light and green light by the red wavelength conversion layer 53R and the green wavelength conversion layer 53G of the wavelength conversion member 150, respectively. Can be converted to light. Then, the blue light from the organic EL element array 130 can be diffused and emitted by the blue diffusion layer 151.
  • the organic EL element 200 converts the red light, the green light, and the blue light emitted from each of the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue diffusion layer 151 of the wavelength conversion member 150 into each color filter. High color purity can be achieved by transmitting 52R, 52G, and 52B.
  • the organic EL element 200 when the blue light from the organic EL part 131 of the organic EL element array 130 passes through the red wavelength conversion layer 53R or the green wavelength conversion layer 53G and is emitted without wavelength conversion,
  • the color filters 52R and 52G of the wavelength conversion member 150 the wavelength characteristics can be adjusted to assist the red wavelength conversion layer 53R or the green wavelength conversion layer 53G. Then, it is possible to reduce the blue light from the organic EL element array 130 that is transmitted without being wavelength-converted by the red wavelength conversion layer 53R or the green wavelength conversion layer 53G and emitted outside the element.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G are formed of the curable resin composition of the third embodiment of the present invention described later. For this reason, the red wavelength conversion layer 53R and the green wavelength conversion layer 53G exhibit excellent fluorescence characteristics, specifically wavelength conversion efficiency. Further, since it is difficult for a residue to occur when the red wavelength conversion layer 53R and the green wavelength conversion layer 53G are formed, color mixing between pixels due to the occurrence of the residues of the wavelength conversion layers 53R and 53G at an undesired portion is also difficult to occur. . As a result of these, the organic EL element 200 can be used for the configuration of an organic EL device that can easily increase the luminance and display an image with high luminance and high image quality.
  • Embodiment 3 FIG. ⁇ Curable resin composition>
  • the curable resin composition of the third embodiment of the present invention includes [A] the same or different polymer molecules, (a1) a structural unit containing an acidic group and (a2) an organic group having 4 to 20 carbon atoms.
  • a polymer having a structural unit hereinafter also referred to as [A] polymer or simply [A] component
  • [B] quantum dots hereinafter also simply referred to as [B] component
  • It is a curable resin composition.
  • the structural unit (a2) containing the organic group having 4 to 20 carbon atoms of the [A] polymer described above is an organic group having 4 to 20 carbon atoms other than the structural unit containing (a1) an acidic group.
  • the constituent unit is preferably included.
  • the curable resin composition of the third embodiment of the present invention contains a [A] polymer and is a resin composition suitable for simple formation of a film or layer by coating or the like.
  • the curable resin composition of 3rd Embodiment of this invention contains the quantum dot of a [B] component with [A] component, [B] increasing the content of a quantum dot [B]. A good dispersion state of the quantum dots can be realized.
  • quantum dots when quantum dots are used together with a resin component, a solvent, or the like to form a composition, they tend to aggregate in the composition, and it is difficult to realize a good dispersion state. In a quantum dot, aggregation will impair its fluorescent properties. Therefore, a composition containing quantum dots usually cannot contain a large amount of quantum dots.
  • the [A] component that is a resin component is selected so as to realize a good dispersion state while containing a large amount of [B] quantum dots. Contained.
  • the curable resin composition of the third embodiment of the present invention can form a resin composition in which a good dispersion state of [B] quantum dots is realized while containing a large amount of [B] quantum dots. it can.
  • the curable resin composition of 3rd Embodiment of this invention forms a layer and a film
  • the curable resin composition of the third embodiment of the present invention can have radiation sensitivity. Therefore, the curable resin composition according to the third embodiment of the present invention preferably contains a [C] polymerizable initiator (hereinafter also simply referred to as “C” component), and [D] polymerization. It is preferable to contain a polymerizable unsaturated compound (hereinafter also simply referred to as [D] component). And the curable resin composition of 3rd Embodiment of this invention can be patterned using the photolithographic method etc. based on the radiation sensitivity.
  • C polymerizable initiator
  • [D] component polymerizable unsaturated compound
  • radiation irradiated upon exposure includes visible light, ultraviolet rays, far ultraviolet rays, X-rays, charged particle beams, and the like.
  • a so-called resist composition is applied to the surface of a substrate to be processed or processed to form a resist film, and a predetermined resist pattern is exposed by irradiation with light or an electron beam.
  • the curable resin composition according to the third embodiment of the present invention can be patterned when necessary to form a cured film patterned into a desired shape. Therefore, the curable resin composition of the third embodiment of the present invention includes a red wavelength conversion layer, a green wavelength, which is a wavelength conversion portion of the wavelength conversion member of the organic EL element of the first embodiment and the second embodiment of the present invention. A conversion layer and a blue wavelength conversion layer can be formed. Each wavelength conversion layer which the wavelength conversion member of the organic EL element of 1st Embodiment of this invention and 2nd Embodiment has is comprised by including [B] quantum dot in resin.
  • the curable resin composition of the third embodiment of the present invention contains [A] component and [B] quantum dots.
  • the curable resin composition of Embodiment 3 of this invention can form the resin composition in which the favorable dispersion state of [B] quantum dots was implement
  • the curable resin composition according to the third embodiment of the present invention uses [B] quantum dots and has an excellent fluorescence emission (wavelength conversion) function (hereinafter referred to as a “wavelength conversion” function).
  • the wavelength conversion portion can be formed by forming a wavelength conversion layer having simply fluorescence or fluorescence characteristics.
  • the curable resin composition of the third embodiment of the present invention can have radiation sensitivity. Therefore, as described above, the curable resin composition of the third embodiment of the present invention preferably further includes [C] a polymerizable initiator, and further includes [D] a polymerizable unsaturated compound. It is preferable to contain.
  • the curable resin composition of 3rd Embodiment of this invention contains an [E] stabilizer (henceforth only [E] component) with [A] component, [B] quantum dot, etc. And a cured film having stable fluorescence characteristics can be formed, and each wavelength conversion layer can be formed.
  • curable resin composition of 3rd Embodiment of this invention can contain the other arbitrary component mentioned later, unless the effect of this invention is impaired.
  • the curable resin composition of 3rd Embodiment of this invention contains a [A] polymer.
  • the polymer has (a1) a structural unit containing an acidic group (hereinafter also simply referred to as the structural unit (a1)) and (a2) 4 carbon atoms in the same or different polymer molecules.
  • To 20 hereinafter also simply referred to as a structural unit (a2)
  • a structural unit (a2) may have other structural units as necessary.
  • the structural unit (a2) of the polymer [A] is preferably a structural unit containing an organic group having 4 to 20 carbon atoms other than the structural unit (a1).
  • the mode of the [A] polymer is not particularly limited, (I) When both the structural unit (a1) and the structural unit (a2) are contained in the same polymer molecule, and [A] one polymer molecule is present in the polymer; (Ii) having a structural unit (a1) in one polymer molecule, and having both the structural unit (a2) in a different polymer molecule, and [A] two kinds of structural units in the polymer When polymer molecules are present; (Iii) having both the structural unit (a1) and the structural unit (a2) in one polymer molecule, and having the structural unit (a1) in a polymer molecule different from the structural unit (a1).
  • polymer molecule has the structural unit (a2), and [A] three polymer molecules exist in the polymer; (Iv) In addition to the polymer molecules specified in (i) to (iii), there may be mentioned a case where [A] the polymer further contains one or more polymer molecules.
  • Examples of the acidic group contained in the structural unit (a1) include a carboxyl group, a phenolic hydroxyl group, and a sulfo group, and a carboxyl group is preferable.
  • Examples of the organic group contained in the structural unit (a1) include an aliphatic hydrocarbon group having 4 to 20 carbon atoms, an alicyclic hydrocarbon group having 4 to 20 carbon atoms, an aromatic hydrocarbon group having 20 or less carbon atoms, And one or more hydrogen atoms of these aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups are a hydroxyl group, a carboxyl group, a halogen, a nitrile group, an alkoxyl group having 1 to 12 carbon atoms, a mercapto group, And groups substituted with a sulfo group.
  • Examples of the aliphatic hydrocarbon group include straight chain such as n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n-dodecyl group, n-tetradecyl group and n-octadecyl group. And branched alkyl groups such as an alkyl group, i-butyl group, t-butyl group, neopentyl group, 2-hexyl group and 3-hexyl group.
  • examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl, a cyclooctyl, a bornyl group, a norbornyl group, an adamantyl group, and the like.
  • examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
  • an aliphatic hydrocarbon group having 4 to 20 carbon atoms and one or more hydrogen atoms of the aliphatic hydrocarbon group may be a hydroxyl group, a carboxyl group, a halogen, or a nitrile.
  • the polymer can be produced by radical copolymerization of a monomer that provides the structural unit (a1), a monomer that provides the structural unit (a2), and a monomer that provides the other structural unit.
  • a monomer that provides the structural unit (a1) a monomer that provides the structural unit (a2)
  • a monomer that provides the other structural unit a monomer that provides the other structural unit.
  • the [A] polymer containing both the structural unit (a1) and the structural unit (a2) in the same polymer molecule at least the monomer that gives the structural unit (a1) and the structural unit (a2) What is necessary is just to copolymerize using the mixture containing the monomer to give.
  • the [A] polymer having the structural unit (a1) in one polymer molecule and the structural unit (a2) in a different polymer molecule is produced, at least the structural unit (a1) is included.
  • a polymer solution having a structural unit (a1) is obtained by radical polymerization of a polymerizable solution containing a monomer to be given, and a polymerizable solution containing at least a monomer giving a structural unit (a2) is separately radically polymerized.
  • the polymer molecule having the structural unit (a2) is obtained, and finally both are mixed to form the [A] polymer.
  • the content of the structural unit (a1) in the polymer is such that when the structural unit (a1) and the structural unit (a2) are included in one polymer molecule, [A] all the structural units included in the polymer
  • the monomer charge ratio is preferably 5% by mass to 70% by mass, more preferably 10% by mass to 60% by mass, and particularly preferably 20% by mass to 50% by mass.
  • the structural unit in the one polymer molecule having the structural unit (a1) is preferably 40% by mass to 99% by mass and more preferably 50% by mass to 98% by mass or less as a monomer charge ratio with respect to all the structural units contained in the polymer molecule.
  • the content of the structural unit (a2) in the [A] polymer is such that when the structural unit (a1) and the structural unit (a2) are contained in one polymer molecule, 10 mass% or more and 60 mass% or less are preferable by monomer preparation ratio with respect to a structural unit, 15 mass% or more and 55 mass% or less are more preferable, and 20 mass% or more and 50 mass% or less are especially preferable.
  • the structural unit in the one polymer molecule having the structural unit (a2) is preferably 10% by mass or more and 80% by mass or less, more preferably 20% by mass or more and 70% by mass or less, based on the monomer charge ratio with respect to all the structural units contained in the polymer molecule. More preferably, 25 mass% or more and 60 mass% or less are especially preferable.
  • the polymer described above is contained in the curable resin composition of the third embodiment of the present invention and dissolved or dispersed.
  • the curable resin composition of 3rd Embodiment of this invention contains the quantum dot of the [B] component mentioned later with a [A] component, and increases [B] quantum dot while increasing the content of a [B] quantum dot. A good dispersion state can be realized.
  • membrane containing a [B] quantum dot can be formed using simple formation methods, such as application
  • the polymer is desirably contained in an amount of 5% by mass or more, more preferably 10% by mass or more, based on the total mass of the curable resin composition. [A] When the polymer is less than 5% by mass in the total mass of the curable resin composition, it is impossible to sufficiently secure the thickness of the coating film obtained from the curable resin composition.
  • Quantum dots which are essential components of the curable resin composition of the third embodiment of the present invention, are preferably semiconductor quantum dots configured using a semiconductor material.
  • the [B] quantum dot is preferably a quantum dot made of a safe material that does not contain Cd and Pb as constituents, and is composed of, for example, In (indium) or Si (silicon). .
  • quantum dots are at least two or more selected from the group of elements represented by Group 2 elements, Group 11 elements, Group 12 elements, Group 13 elements, Group 14 elements, Group 15 elements and Group 16 elements.
  • a quantum dot made of a compound containing an element is preferable.
  • elements such as Pb and Cd which are of great concern for human safety, are excluded, and Be (beryllium), Mg (magnesium), Ca (calcium), Sr (strontium), Ba (Barium), Cu (copper), Ag (silver), gold (Au), zinc (Zn), B (boron), Al (aluminum), Ga (gallium), In (indium), Tl (thallium), C (Carbon), Si (silicon), Ge (germanium), Sn (tin), N (nitrogen), P (phosphorus), As (arsenic), Sb (antimony), Bi (bismuth), O (oxygen), S A quantum dot made of a compound containing at least two elements selected from the group consisting of (sulfur), Se (selenium), Te (tellurium) and Po (polonium) is preferable.
  • the [B] quantum dot is preferably composed of a compound (a) having a fluorescence maximum in a wavelength region of 500 nm to 600 nm and / or a compound (b) having a fluorescence maximum in a wavelength region of 600 nm to 700 nm.
  • the quantum dot is composed of the compound (a) and / or the compound (b) having such fluorescence emission characteristics, so that the quantum dot is fluorescent in the wavelength region of 500 nm to 600 nm and / or in the wavelength region of 600 nm to 700 nm. Can have a maximum.
  • the curable resin composition according to the third embodiment of the present invention containing [B] quantum dots can form each wavelength conversion layer in a CCM organic EL element that emits visible light. .
  • the above-described first embodiment and second embodiment of the present invention are included by including [B] quantum dots having desired fluorescence emission characteristics.
  • Curing resin composition for forming red wavelength conversion layer 53R which is a wavelength conversion part of wavelength conversion members 50 and 150 of organic EL elements 100 and 200 of embodiment, and hardening for forming green wavelength conversion layer 53G It can be used as a curable resin composition or a curable resin composition for forming the blue wavelength conversion layer 53B.
  • the [B] quantum dot contained in the curable resin composition of the third embodiment of the present invention is a quantum dot made of a compound containing In as a constituent component.
  • [B] quantum dots may include Si or Si compounds.
  • Si is particularly preferable among Si or Si compounds.
  • the curable resin composition of the third embodiment of the present invention can form a cured film having safer and more excellent fluorescence characteristics. Furthermore, each wavelength conversion which is a wavelength conversion part of the wavelength conversion members 50 and 150 of the organic EL elements 100 and 200 of the first embodiment and the second embodiment of the present invention, which is safe and has superior fluorescence characteristics. Layers 53R, 53G, and 53B can be formed.
  • Quantum dots contained in the curable resin composition of the third embodiment of the present invention are selected from a homogeneous structure type composed of one compound and a core-shell structure type composed of two or more compounds. It is preferable that the quantum dots have at least one structure type.
  • the core-shell structure type [B] quantum dots are formed by forming a core structure with one kind of compound and covering the periphery of the core structure with another compound. For example, by covering the core semiconductor with a semiconductor having a larger energy band gap, excitons (electron-hole pairs) generated by photoexcitation are confined in the core. As a result, the probability of non-radiative transition on the surface of the quantum dots is reduced, and the quantum yield of light emission and the stability of the fluorescence characteristics of [B] quantum dots are improved.
  • Quantum dots contained in the curable resin composition of the third embodiment of the present invention are InP / ZnS, CuInS 2 / ZnS, which are core-shell structured quantum dots, in consideration of the component configuration and structure, and It is preferably at least one selected from the group consisting of (ZnS / AgInS 2 ) solid solution / ZnS, and AgInS 2 which is a homogeneous structure type quantum dot and Zn-doped AgInS 2 .
  • [B] quantum dots contained in the curable resin composition of the third embodiment of the present invention are InP / ZnS compound, CuInS 2 / ZnS compound, AgInS 2 compound, (ZnS / AgInS 2 ) solid solution / It is preferably at least one selected from the group consisting of ZnS compounds, Zn-doped AgInS 2 compounds and Si compounds.
  • the curable resin composition according to the third embodiment of the present invention containing the [B] quantum dots exemplified above can form a cured film that is safe and has excellent fluorescence characteristics.
  • each wavelength conversion layer which is a wavelength conversion part of the wavelength conversion member of the organic EL element of 1st Embodiment and 2nd Embodiment of this invention provided with the outstanding fluorescence characteristic can be formed.
  • the [B] quantum dots contained in the curable resin composition of the third embodiment of the present invention preferably have an average particle size of 0.5 nm to 20 nm, and preferably 1.0 nm to 10 nm. More preferred.
  • the average particle size is less than 0.5 nm, it is difficult to prepare [B] quantum dots, and even if it can be prepared, the fluorescence characteristics of [B] quantum dots may become unstable.
  • the average particle diameter of the quantum dots exceeds 20 nm, the quantum confinement effect due to the size of the quantum dots may not be obtained, and the desired fluorescence characteristics cannot be obtained, which is not desirable.
  • the shape of the quantum dots is not particularly limited, and may be, for example, a spherical shape, a rod shape, a disk shape, or other shapes.
  • Information such as the particle size, shape, and dispersion state of the quantum dots can be obtained by a transmission electron microscope (TEM).
  • a known method of thermally decomposing an organometallic compound in a coordinating organic solvent may be used. it can.
  • core-shell type quantum dots form a homogeneous core structure by reaction, then add a precursor to form a shell on the core surface in the reaction system, and stop the reaction after shell formation. It can be obtained by separating from a solvent.
  • a commercially available product can also be used.
  • the content of [B] quantum dots in the curable resin composition of the third embodiment of the present invention is preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the above-mentioned [A] component. More preferably, it is 0.2 to 50 parts by mass.
  • [B] By setting the content of quantum dots in the above range, a cured film having excellent fluorescence characteristics is formed, and as a result, each wavelength that is a wavelength conversion part of a wavelength conversion member having excellent fluorescence characteristics A conversion layer can be formed.
  • the content of the quantum dots is less than 0.1 parts by mass with respect to 100 parts by mass of the [A] component, the desired fluorescent properties cannot be obtained in the cured film to be formed.
  • the wavelength conversion layer of the wavelength conversion member having the characteristics cannot be formed.
  • the stability of the cured film formed will be impaired and in the organic EL element, each stable wavelength conversion layer cannot be formed.
  • the curable resin composition of the third embodiment of the present invention can further contain a [C] polymerization initiator.
  • the [C] polymerization initiator of this embodiment is preferably one that generates an active species that can initiate polymerization of a compound having a polymerizable group in response to radiation. Therefore, the [C] polymerization initiator of this embodiment is preferably a radiation-sensitive polymerization initiator, that is, a radiation-sensitive polymerization initiator.
  • the curable resin composition of 3rd Embodiment of this invention can improve radiation sensitivity and can improve patternability by containing a [C] polymerization initiator. And the curable resin composition of 3rd Embodiment of this invention can form the cured film patterned using well-known patterning methods, such as the photolithographic method, The wavelength conversion member of an organic EL element It is possible to easily form each wavelength conversion layer that is the wavelength conversion part.
  • [C] The polymerization initiator is used together with the [D] polymerizable unsaturated compound described later, and is preferably contained in the curable resin composition of the third embodiment of the present invention. Thereby, the curable resin composition of the third embodiment of the present invention can further improve the cross-linking reactivity, the strength of each wavelength conversion layer of the wavelength conversion member formed from this curable resin composition, and Adhesion with the substrate can be further enhanced.
  • examples of the [C] polymerization initiator include oxime ester compounds, acetophenone compounds, biimidazole compounds, and the like. In addition, you may use [C] polymerization initiator individually or in combination of 2 or more types.
  • oxime ester compound examples include ethanone-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), 1,2-octane.
  • acetophenone compound examples include ⁇ -aminoketone compounds.
  • Examples of the ⁇ -aminoketone compound include 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one and the like.
  • the acetophenone compound is preferably an ⁇ -aminoketone compound, such as 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, 2- Methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one is more preferred.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2 ′ -Biimidazole and the like.
  • a commercially available product may be used as the polymerization initiator.
  • 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (Irgacure (registered trademark) 907)
  • 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) -butan-1-one (Irgacure 379)
  • 1,2-octanedione-1- [4- ( Phenylthio) -2- (O-benzoyloxime)] (Irgacure (registered trademark) OXE01)
  • ethanone-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime) (Irgacure (registered trademark) OXE02) (manufactured by BASF Japan Ltd.).
  • the [C] polymerization initiator is preferably a polymerization initiator having no nitrogen atom in the molecule.
  • the curable resin composition of the third embodiment of the present invention can easily form a wavelength conversion layer of an organic EL device having better fluorescence characteristics. Can be formed.
  • Such a polymerization initiator having no nitrogen atom in the molecule include, for example, 2,2-dimethoxy-1,2-diphenylethane-1-one (Irgacure (registered trademark) 651), 1- Hydroxycyclohexyl phenyl ketone (Irgacure® 184), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Irgacure® 1173), 1- [4- (2-hydroxyethoxy) -Phenyl] -2-hydroxy-2-methyl-1-propan-1-one (Irgacure® 2959), 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) ) -Benzyl] phenyl ⁇ -2-methyl-propan-1-one (Irgacure® 127), phenylglyoxyl Acid methyl ester (Darocur® MBF), 2,4,6-trimethylbenzoyl-diphenyl-phosphine
  • the content of the polymerization initiator is preferably 0.1 part by mass to 40 parts by mass, and more preferably 0.5 part by mass to 20 parts by mass with respect to 100 parts by mass of the component [A].
  • the curable resin composition of the third embodiment of the present invention exhibits good patternability even in the case of a low exposure amount, and has a sufficient surface.
  • a cured film having hardness and adhesion can be formed to provide a wavelength conversion layer of the organic EL element.
  • the curable resin composition of the third embodiment of the present invention may further contain a [D] polymerizable unsaturated compound.
  • the [D] polymerizable unsaturated compound contained in the curable resin composition of the third embodiment of the present invention is a compound having a polymerizable unsaturated structure. Crosslinking reactivity can be improved because the curable resin composition of 3rd Embodiment of this invention contains a [D] polymerizable unsaturated compound.
  • each wavelength conversion layer which is a wavelength conversion part of the wavelength conversion member of the organic EL element of 1st Embodiment and 2nd Embodiment of this invention formed from this curable resin composition, intensity
  • the [D] polymerizable unsaturated compound is preferably used together with the above-described [C] polymerization initiator and contained in the curable resin composition of the third embodiment of the present invention.
  • Such a [D] polymerizable unsaturated compound is a monofunctional, bifunctional, or trifunctional (meth) acrylic acid ester from the viewpoint of good polymerizability and improved strength of the resulting cured film. Is preferred.
  • Examples of the monofunctional (meth) acrylic acid ester include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, diethylene glycol monoethyl ether acrylate, diethylene glycol monoethyl ether methacrylate, (2-acryloyloxyethyl) (2-hydroxy Propyl) phthalate, (2-methacryloyloxyethyl) (2-hydroxypropyl) phthalate, and ⁇ -carboxypolycaprolactone monoacrylate.
  • bifunctional (meth) acrylic acid ester examples include ethylene glycol diacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, tetraethylene glycol diacrylate, and tetraethylene glycol.
  • Examples include dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol diacrylate, and 1,9-nonanediol dimethacrylate.
  • Examples of commercially available products include Aronix (registered trademark) M-210, M-240, M-6200 (manufactured by Toagosei Co., Ltd.); KAYARAD (registered trademark) HDDA, HX-220, R-604. (Nippon Kayaku Co., Ltd.); Biscoat 260, 312, and 335HP (Osaka Organic Chemical Co., Ltd.); Light acrylate (registered trademark) 1,9-NDA (Kyoeisha Chemical Co., Ltd.) and the like.
  • tri- or more functional (meth) acrylic acid ester examples include trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, and ditrimethylolpropane.
  • tri (2-acryloyloxyethyl) phosphate tri (2-methacryloyloxyethyl) phosphate
  • succinic acid-modified pentaerythritol triacrylate succinic acid-modified dipentaerythritol pentaacrylate
  • Examples of commercially available products include Aronix (registered trademark) M-309, M-400, M-405, M-450, M-7100, M-8030, M-8060, and TO-1450. (Above, manufactured by Toagosei Co., Ltd.); KAYARAD (registered trademark) TMPTA, DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-60, DPCA-120, DPEA-12 (above, Nippon Kayaku Co., Ltd.) ); Biscoat (registered trademark) 295, 300, 360, GPT, 3PA, 400 (above, manufactured by Osaka Organic Chemical Industry Co., Ltd.); As a commercial product containing a polyfunctional urethane acrylate compound, New Frontier (Registered Trademark) R-1150 (Daiichi Kogyo Seiyaku Co., Ltd.), KAYARAD (Registered Trademark) DPHA-40H (Nippon Kayaku Co., Ltd.),
  • the polymerizable unsaturated compound described above may be used alone or in combination of two or more.
  • the proportion of the [D] polymerizable unsaturated compound used in the curable resin composition of the third embodiment of the present invention is preferably 30 parts by mass to 250 parts by mass with respect to 100 parts by mass of the component [A]. More preferred is 200 to 200 parts by weight.
  • the curable resin composition of the third embodiment of the present invention can further contain an [E] stabilizer.
  • the curable resin composition of the third embodiment of the present invention is obtained by using an [E] stabilizer in addition to the essential components such as the [A] component and the [B] component.
  • the light conversion efficiency can be improved.
  • a stabilizer [E] preferable as a component of the curable resin composition of the third embodiment of the present invention includes a phosphite antioxidant.
  • the phosphite antioxidant comprises a compound having a phosphite structure.
  • examples of the [E] stabilizer include a phosphine compound, a phenol compound, a compound having a hindered phenol structure, a compound having a hindered amine structure, and a compound having a thioether structure.
  • phosphite antioxidants include tris (2,4-di-tert-butylphenyl) phosphite and bis [2,4-bis (1,1-dimethylethyl) -6-methylphenyl] ethyl ester.
  • Phosphorous acid bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,4-dicumylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl) -4-methylphenyl) pentaerythritol-di-phosphite, trisnonylphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite, and the like.
  • ADK STAB registered trademark
  • PEP-36 Examples of commercially available products include ADK STAB (registered trademark) PEP-36, PEP-4C, PEP-8, PEP-8F, PEP-8W, PEP-11C, PEP-24G, and HP-10.
  • ADK STAB registered trademark
  • P Examples of commercially available products include ADK STAB (registered trademark) PEP-36, PEP-4C, PEP-8, PEP-8F, PEP-8W, PEP-11C, PEP-24G, and HP-10.
  • 2112, 260 ADK STAB (registered trademark) P, ADK STAB (registered trademark) QL, 522A, 329K, 1178, 1500
  • ADK STAB (registered trademark) C, 135A, 3010 Examples of commercially available products include ADK STAB (registered trademark) ) TPP (above, manufactured by Adeka), Irgafos (registered trademark) 38, Irgafos (registered
  • Examples of the phosphine compound include triphenylphosphine, cyclohexyldiphenylphosphine, ethyldiphenylphosphine, tri (o-tolyl) phosphine, tri (m-tolyl) phosphine, tri (p-tolyl) phosphine, and tris (2,5-dimethyl). Phenyl) phosphine, tris (3,5-dimethylphenyl) phosphine, and the like. Examples of commercially available products include TPP, DPCP, TOTP, TMTP, TPTP (all of which are manufactured by Hokuko Chemical Co., Ltd.). Of these, aromatic phosphite antioxidants or phosphine compounds represented by the following formula are particularly preferred.
  • R A represents a single bond or an oxygen atom.
  • R B represents an alkyl group having 1 to 12 carbon atoms, a cyclopentyl group, a cyclohexyl group, a phenyl group, a tolyl group, a xylyl group, or a naphthyl group.
  • R C represents a hydrocarbon group having 1 to 30 carbon atoms. n represents an integer of 1 to 3, and m represents an integer of 0 to 5.
  • R B in the above formula methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-methylpropyl group, 1-methylpropyl group, t-butyl group, pentyl group, isopentyl group Group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, cyclopentyl group, cyclohexyl group, phenyl group, tolyl group, xylyl group, naphthyl group and the like.
  • R C in the above formula methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, 2-methylpropyl group, 1-methylpropyl group, t-butyl group, pentyl group, isopentyl group Group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, Eicosyl group, heicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl
  • Examples of the above-mentioned phenol compound include 4-methoxyphenol, 4-ethoxyphenol, and the like.
  • Examples of the compound having a hindered phenol structure described above include 2,6-di-tert-butyl-4-cresol, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl).
  • Examples of commercially available compounds having the above hindered phenol structure include ADK STAB (registered trademark) AO-20, AO-30, AO-40, AO-50, AO-60, and AO-70. , AO-80, AO-330 (manufactured by Adeka), sumilizer (registered trademark) GM, GS, MDP-S, BBM-S, WX-R, GA-80 (and above) Manufactured by Sumitomo Chemical Co., Ltd.), IRGANOX (registered trademark) 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 245, 259, 3114, 565, IRGAMOD (Registered trademark) 295 (above, manufactured by BASF Japan), Yoshinox (registered trademark) BHT, BB, 2246G, 425, 250, 930, the SS, the TT, the 917, the 314 (or, API Corporation Co., Ltd.
  • Examples of commercially available compounds having a hindered amine structure include ADK STAB (registered trademark) LA-52, LA57, LA-62, LA-67, LA-63P, LA-68LD, LA-77, LA-82, LA-87 (manufactured by Adeka), sumilizer (registered trademark) 9A (manufactured by Sumitomo Chemical), CHIMASSORB (registered trademark) 119FL, 2020FDL, 944FDL, TINUVIN (registered trademark) 622LD 144, 765, and 770DF (manufactured by BASF Japan Ltd.).
  • Adekastab registered trademark
  • AO-412S manufactured by Adeka
  • sumilizer registered trademark
  • TPL-R manufactured by Adeka
  • TPM manufactured by TPM
  • TPS TP-D
  • MB above, manufactured by Sumitomo Chemical Co., Ltd.
  • IRGANOX registered trademark
  • PS800FD PS802FD
  • DLTP DLTP
  • DSTP DSTP
  • DMTP DMTP
  • DTTP aboveve, manufactured by API Corporation
  • [E] stabilizers may be used alone or in admixture of two or more.
  • the content of [E] stabilizer in the curable resin composition of the third embodiment of the present invention is preferably 0.1 to 10 parts by mass, more preferably 100 parts by mass of [A] component. Is 0.2 to 5 parts by mass.
  • the organic EL device of the first embodiment and the second embodiment of the present invention obtained from the curable resin composition of the third embodiment of the present invention is used. In each wavelength conversion layer that is a wavelength conversion unit, the light conversion efficiency can be further improved.
  • the curable resin composition of the third embodiment of the present invention contains the [A] component and [B] quantum dots as essential components, and contains other optional components as long as the effects of the present invention are not impaired. be able to.
  • other optional components include a solvent, a curing accelerator, and a thermal acid generator.
  • the curing accelerator is a compound that functions to accelerate the curing of the film formed by the curable resin composition of the present embodiment.
  • the thermal acid generator is a compound capable of releasing an acidic active substance that acts as a catalyst when the resin is cured by applying heat.
  • the curable resin composition of the third embodiment of the present invention is a range that does not impair the effects of the present invention, such as a surfactant, a storage stabilizer, an adhesion aid, and a heat resistance improver.
  • a surfactant such as sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium sulfate, sodium
  • the curable resin composition of the third embodiment of the present invention is prepared by uniformly mixing the [A] polymer and [B] quantum dots.
  • the optional [C] component, [D] component, and [E] component are included, the [C] component and [D] as necessary together with the [A] component and [B] component It is prepared by mixing the components and [E] component uniformly.
  • an organic solvent can be used to prepare a curable resin composition in a dispersion state.
  • the organic solvent for example, by adjusting the viscosity of the curable resin composition of the third embodiment of the present invention, it is possible to improve applicability to a substrate, etc., and improve operability and moldability. For example.
  • organic solvent examples include those that dissolve or disperse other components and that do not react with other components.
  • organic solvents include alcohols, ethers, diethylene glycol alkyl ethers, ethylene glycol alkyl ether acetates, propylene glycol monoalkyl ethers, propylene glycol monoalkyl ether acetates, propylene glycol monoalkyl ether propio.
  • examples include nates, hydrocarbons, ketones, and esters.
  • Examples of alcohols include benzyl alcohol and diacetone alcohol;
  • Examples of ethers include tetrahydrofuran, dialkyl ethers such as diisopropyl ether, di n-butyl ether, di n-pentyl ether, diisopentyl ether, and di n-hexyl ether;
  • Examples of diethylene glycol alkyl ethers include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol ethyl methyl ether;
  • Examples of ethylene glycol alkyl ether acetates include methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol monobutyl ether acetate, and ethylene glycol monoethyl ether acetate;
  • Examples of propylene glycol monoalkyl ethers include propylene
  • a hydrocarbon solvent is preferred from the viewpoint of the dispersibility of the quantum dots.
  • the hydrocarbon include an aromatic hydrocarbon solvent and an aliphatic hydrocarbon solvent.
  • the aromatic hydrocarbon solvent include toluene, ethylbenzene, amylbenzene, isopropylbenzene, xylene, cyclohexylbenzene, naphthalene, dimethylnaphthalene, cymene, tetralin, biphenyl, mesitylene and the like.
  • Aliphatic hydrocarbon solvents include hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, methylcyclohexane, ethylcyclohexane, p-menthane, pinane, decalin, isooctane, isododecane, cyclohexene, cyclopentane, dipentene, Isopar E, Isopar G, Isopar H, Isopar L, Isopar M (manufactured by Kokura Kosan), turpentine oil, decahydronaphthalene, limonene, ⁇ -pinene, ⁇ -pinene, benzine, Kyowasol C-800, shell sol , Isosol, ligroin (manufactured by Gordo Kogyo Co., Ltd.), and the like.
  • ethers such as dialkyl ethers, diethylene glycol alkyl ethers, ethylene glycol from the viewpoint of excellent solubility, non-reactivity with each component, and ease of film formation.
  • Alkyl ether acetates, propylene glycol monoalkyl ethers, propylene glycol monoalkyl ether acetates, ketones and esters are preferred, especially diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl Ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol mono Tyl ether acetate, cyclohexanone, propyl acetate, i-propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate
  • High-boiling solvents such as nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, ⁇ -butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, carbitol acetate can be used in combination.
  • the content of the organic solvent in the curable resin composition of the third embodiment of the present invention can be appropriately determined in consideration of viscosity and the like. That is, the solid content concentration of the curable resin composition of the present embodiment (components other than the solvent component in the curable resin composition solution) can be arbitrarily set according to the purpose of use, desired film thickness, and the like. However, it is preferably 5% by mass to 50% by mass, more preferably 10% by mass to 40% by mass, and still more preferably 15% by mass to 35% by mass.
  • each wavelength conversion layer which is a wavelength conversion part of the organic EL element of a form.
  • Embodiment 4 FIG. ⁇ Method for forming wavelength conversion section>
  • the wavelength conversion unit obtained by the wavelength conversion unit forming method of the fourth embodiment of the present invention includes, for example, the organic EL element 100 of the first embodiment of the present invention shown in FIGS. 1 and 2 and the second of the present invention. It is a wavelength conversion part of the wavelength conversion members 50 and 150 of the organic EL element 200 of the embodiment, and specifically, the wavelength conversion layers 53R, 53G, and 53B.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G included in the wavelength conversion member 150 of the organic EL element 200 according to the second embodiment of the present invention shown in FIG. Can be formed.
  • the curable resin composition of the third embodiment of the present invention described above is applied onto a base material, patterned as necessary, and then exposed. Curing is performed to form a patterned cured film. And the obtained cured film can be made into the wavelength conversion part which the wavelength conversion member of the organic EL element of 1st Embodiment of this invention and 2nd Embodiment has, More specifically, each wavelength conversion layer It can be.
  • the substrate as shown in FIGS. 1 and 2, a substrate having red color filters 52R, green color filters 52G, and blue color filters 52B regularly arranged on the substrate 51 is used. be able to.
  • the following steps (1) to (step) are performed so that the wavelength converter having a desired shape and arrangement is formed on the base material. It is preferable to include (4) in the following order.
  • the coating film formation process which forms the coating film of the curable resin composition of 3rd Embodiment of this invention on a base material.
  • a radiation irradiation step of irradiating at least part of the coating film formed in step (1) with radiation.
  • FIGS. 3 to 6 are diagrams for explaining an example of the method of forming the wavelength conversion unit according to the fourth embodiment of the present invention.
  • FIG. 3 is a cross-sectional view of a base material for explaining an example of a coating film forming step in the method for forming a wavelength conversion portion according to the fourth embodiment of the present invention.
  • FIG. 4 is a cross-sectional view schematically illustrating an example of a radiation irradiation step in the method for forming a wavelength conversion unit according to the fourth embodiment of the present invention.
  • FIG. 5 is a cross-sectional view of a substrate for explaining an example of a developing process in the method for forming a wavelength conversion portion according to the fourth embodiment of the present invention.
  • FIG. 6 is a cross-sectional view of a cured film and a substrate for explaining an example of a curing process in the method for forming a wavelength conversion portion of the fourth embodiment of the present invention.
  • the base material 2 in FIGS. 3 to 6 has the red color filter 52R, the green color filter 52G, and the blue color filter 52B regularly arranged on the substrate 51 as described above. 3 to 6, the red color filter 52R, the green color filter 52G, and the blue color filter 52B are not shown and are shown as the base material 2 for convenience.
  • step (1) coating film forming step
  • step (4) curing step
  • Step (1) In the coating film forming step, which is the step (1) of the method for forming the wavelength conversion portion of the fourth embodiment of the present invention, as illustrated in FIG. 3, the curable resin composition of the third embodiment of the present invention A coating film 1 is formed on the substrate 2.
  • the curable resin composition described above contains selected and selected quantum dots that convert excitation light into red light. Yes.
  • the curable resin composition described above contains selected and contained quantum dots that convert excitation light into green light, thereby forming the blue wavelength conversion layer 53B. In this case, a quantum dot that converts excitation light into blue light is selected and contained in the curable resin composition described above.
  • the red wavelength conversion layer, the green wavelength conversion layer, and the blue wavelength conversion layer of the wavelength conversion member of the organic EL element are to be formed, different emission characteristics are obtained.
  • three types of curable resin compositions of the third embodiment are prepared.
  • the method for forming the wavelength conversion section of the fourth embodiment of the present invention including the above-described steps (1) to (4) is repeated, so that the red wavelength conversion layer and the green wavelength conversion layer are formed on one substrate.
  • the blue wavelength conversion layer can be formed sequentially.
  • each wavelength conversion layer can be formed on one base material, a wavelength conversion part can be comprised, and the wavelength conversion member of an organic EL element can be obtained.
  • the base material 2 on which the coating film 1 is formed regularly arranges the red color filter 52R, the green color filter 52G, and the blue color filter 52B on the substrate 51 of FIG. Have.
  • the substrate 51 glass, quartz, silicon, or resin (for example, polyimide, polyethylene naphthalate, polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, polyester, cyclic olefin ring-opening polymer and hydrogen thereof)
  • a substrate made of an additive or the like can be used.
  • these substrates may be subjected to pretreatment such as chemical treatment with a silane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition or the like, if desired.
  • the base material 2 after applying the curable resin composition of 3rd Embodiment of this invention to one surface, it prebakes and components, such as the organic solvent contained in the curable resin composition, evaporate. Then, the coating film 1 is formed.
  • Examples of the coating method of the curable resin composition of the third embodiment of the present invention in this step include a spray method, a roll coating method, and a spin coating method (sometimes referred to as a spin coating method or a spinner method).
  • An appropriate method such as a slit coating method (slit die coating method), a bar coating method, or an ink jet coating method can be employed.
  • the spin coating method or the slit coating method is preferable because a film having a uniform thickness can be formed.
  • the pre-baking conditions described above vary depending on the type of each component constituting the curable resin composition, the blending ratio, etc., but it is preferably performed at a temperature of 70 ° C. to 120 ° C., and the time is heated by a hot plate, oven, or the like. Although it varies depending on the apparatus, it is about 1 to 15 minutes.
  • Step (2) Next, in the radiation irradiation step, which is the step (2) of the method for forming the wavelength conversion part of the fourth embodiment of the present invention, as illustrated in FIG. 4, the step was formed on the substrate 2 in the step (1).
  • Radiation 4 is applied to at least a part of the coating film 1.
  • the photomask 3 having a pattern corresponding to formation of a desired shape.
  • a part of the irradiated radiation 4 passes through the photomask, and a part of the radiation 4 a is irradiated onto the coating film 1.
  • Examples of the radiation 4 used for irradiation include visible light, ultraviolet light, and far ultraviolet light. Of these, radiation having a wavelength in the range of 200 nm to 550 nm is preferable, and radiation including ultraviolet light of 365 nm is more preferable.
  • the dose of radiation 4 (exposure amount), the intensity at the wavelength 365nm radiation 4 as a value measured by a luminometer (OAI model 356, Optical Associates Ltd. Inc.), be 10J / m 2 ⁇ 10000J / m 2 can be preferably 100J / m 2 ⁇ 5000J / m 2, 200J / m 2 ⁇ 3000J / m 2 is more preferable.
  • Step (3) Next, in the development step, which is the step (3) of the method for forming a wavelength conversion portion according to the fourth embodiment of the present invention, as illustrated in FIG. Then, unnecessary portions are removed, and the coating film 1a patterned into a predetermined shape is obtained.
  • Examples of the developer used for development include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and ammonia, and tetramethylammonium hydroxide and tetraethylammonium hydroxide.
  • An aqueous solution of an alkaline compound such as a quaternary ammonium salt, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5-diazabicyclo- [4.3.0] -5-nonene Can be used.
  • An appropriate amount of a water-soluble organic solvent such as methanol or ethanol can be added to the aqueous solution of the alkaline compound described above.
  • the surfactant can be used alone or in combination with the addition of the above-mentioned water-soluble organic solvent.
  • the developing method may be any of a liquid piling method, a dipping method, a shower method, a spray method, and the like.
  • the developing time can be 5 seconds to 300 seconds at room temperature, preferably 10 seconds to 180 seconds at room temperature. is there. Following the development treatment, for example, washing with running water is performed for 30 seconds to 90 seconds, and then air-dried with compressed air or compressed nitrogen to obtain the coating film 1a patterned into a predetermined shape.
  • Step (4) Next, in the curing step, which is the step (4) of the method for forming the wavelength conversion portion of the fourth embodiment of the present invention, the patterned coating film 1a illustrated in FIG. 5 is exposed by exposure using an exposure apparatus. Curing (also called post exposure). Thereby, the cured film 5 formed on the base material 2 is obtained as illustrated in FIG. The cured film 5 is patterned by the above process so as to have a desired shape.
  • the cured film 5 is formed using the curable resin composition of the third embodiment of the present invention described above. Irradiate part of the film. Specifically, the coating film formed in step (1) and patterned in step (2) and step (3) is irradiated with predetermined radiation. Examples of the radiation used at this time include ultraviolet rays, far ultraviolet rays, X-rays, and charged particle beams.
  • Examples of the ultraviolet rays include g-line (wavelength 436 nm), i-line (wavelength 365 nm), and the like.
  • Examples of the far ultraviolet light include KrF excimer laser light.
  • Examples of X-rays include synchrotron radiation.
  • Examples of the charged particle beam include an electron beam.
  • ultraviolet rays are preferably used, and among these ultraviolet rays, radiation containing at least one of g-line, h-line and i-line is more preferable.
  • the exposure dose of radiation is preferably 0.1 J / m 2 to 30000 J / m 2 .
  • the cured film formed by the above steps (1) to (4) includes [B] quantum dots in the resin component, and has a fluorescence emission (wavelength conversion) function based on [B] quantum dots. . Therefore, the formed cured film includes the red wavelength conversion layer 53R, the green wavelength conversion layer 53G, and the blue color that the wavelength conversion member 50 of the organic EL element 100 according to the first embodiment of the present invention illustrated in FIGS. 1 and 2 has.
  • the red wavelength conversion layer 53R and the green wavelength conversion layer 53G included in the wavelength conversion layer 53B and the wavelength conversion member 150 of the organic EL element 200 of the second embodiment can be configured.
  • the wavelength included in the wavelength conversion members 50 and 150 of the organic EL elements 100 and 200 of the first embodiment and the second embodiment of the present invention is different from the excitation light.
  • the wavelength conversion layers 53R, 53G, and 53B can be formed as a wavelength conversion unit that emits the fluorescence.
  • the cured film formed by the steps (1) to (4) has a total light transmittance (thickness of 0.1 mm) in the resin constituting the cured film so that the light use efficiency can be increased.
  • JIS K7105 is preferably 75% to 95%, more preferably 78% to 95%, still more preferably 80% to 95%. If the total light transmittance is in such a range, the obtained cured film can form the wavelength conversion layers 53R, 53G, and 53B with excellent light utilization efficiency, and can constitute a wavelength conversion unit.
  • Synthesis example 1 [Synthesis of Polymer (A-1)] A flask equipped with a condenser and a stirrer was charged with 150 parts by mass of propylene glycol monomethyl ether acetate and purged with nitrogen. Heating to 80 ° C., at the same temperature, 50 parts by mass of propylene glycol monomethyl ether acetate, 30 parts by mass of 2-methacryloyloxyethyl succinic acid, 10 parts by mass of benzyl methacrylate, 60 parts by mass of 2-ethylhexyl methacrylate and 2,2 ′ A mixed solution of 6 parts by mass of azobis (2,4-dimethylvaleronitrile) was added dropwise over 2 hours, and polymerization was carried out for 1 hour while maintaining this temperature.
  • azobis 2,4-dimethylvaleronitrile
  • the temperature of the reaction solution was raised to 90 ° C., and further polymerized for 1 hour to obtain a polymer (A-1).
  • Quantum dot A InP / ZnS core-shell quantum dot
  • quantum dot A InP / ZnS core-shell type quantum dot used in the following examples can be synthesized by a generally known method.
  • quantum dots A InP / ZnS core-shell quantum dots can be synthesized by referring to the method described in the technical document “Journal of American Chemical Society. 2007, 129, 15432-15433”.
  • Example 1 [Preparation of Curable Resin Composition ( ⁇ -I)] After adding 40 parts by mass of methylcyclohexane to 90 parts by mass of the polymer (A-1) solution, 10 parts by mass of quantum dots A are mixed to prepare a uniform solution, and 1,2-octanedione-1 -[4- (Phenylthio) -2- (O-benzoyloxime)] (Irgacure (registered trademark) OXE01 manufactured by BASF Japan Ltd.) 10 parts by mass and 70 parts by mass of 1,9-nonanediol diacrylate were mixed and cured. A resin composition ( ⁇ -I) was prepared.
  • Example 2 [Formation of cured film using curable resin composition ( ⁇ -I)]
  • the curable resin composition ( ⁇ -I) prepared in Example 1 was applied onto an alkali-free glass substrate with a spinner and then pre-baked on an 80 ° C. hot plate for 2 minutes to form a coating film.
  • the edge part of the patterned cured film was observed with an optical microscope, and it was judged that the patterning property was good when there was no development residue and the linear part of the pattern was linearly formed. As a result, the patternability of the cured film formed by patterning using the curable resin composition ( ⁇ -I) was good.
  • Example 3 Evaluation of fluorescence characteristics
  • the cured film obtained by the formation method of Example 2 was further examined for fluorescence quantum yield at 25 ° C. using an absolute PL quantum yield measuring apparatus (C11347-01, Hamamatsu Photonics).
  • the fluorescence quantum yield was 38%, and the fluorescence characteristics were judged to be good. Therefore, the cured film by the forming method of Example 2 contains quantum dots.
  • the cured film by the formation method of Example 2 is applied to an organic EL element, and a red wavelength conversion layer can be formed as a wavelength conversion part of the wavelength conversion member, thereby increasing the brightness of the organic EL element. Can be realized.
  • the cured film formed using the curable resin composition of the present invention has excellent fluorescence characteristics and is easy to pattern. Therefore, it can utilize also in the field

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Abstract

L'invention concerne : un élément électroluminescent organique qui a une unité de conversion de longueur d'onde contenant des points quantiques et ne montre pas de diminution des propriétés de formation de motifs de l'unité de conversion de longueur d'onde, tout en étant facilement amélioré en termes de luminance ; une composition de résine durcissable ; un procédé de formation d'une unité de conversion de longueur d'onde ; et un dispositif électroluminescent organique. Un élément électroluminescent organique (100) comprend : une unité électroluminescente organique (31) qui émet une lumière contenant de la lumière bleue ; des couches de conversion de longueur d'onde (53R, 53G, 53B) qui convertissent la longueur d'onde de la lumière provenant de l'unité électroluminescente organique (31) ; et des filtres colorés (52R, 52G, 52B). Les couches de conversion de longueur d'onde (53R, 53G, 53B) sont formées à l'aide d'une composition de résine durcissable qui contient [A] un polymère qui contient (a1) une unité constitutive contenant un groupe acide et (a2) une unité constitutive contenant un groupe organique ayant de 4 à 20 atomes de carbone dans une seule et même molécule de polymère ou dans différentes molécules de polymère, et [B] des points quantiques. Un dispositif électroluminescent organique qui effectue un affichage d'image est obtenu à l'aide de cet élément électroluminescent organique (100).
PCT/JP2015/083636 2014-12-15 2015-11-30 Élément électroluminescent organique, composition de résine durcissable, procédé de formation d'unité de conversion de longueur d'onde, et dispositif électroluminescent organique Ceased WO2016098570A1 (fr)

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