WO2017221777A1 - Corps émetteur de lumière, unité source de lumière dans lequel il est utilisé, afficheur et dispositif d'éclairage - Google Patents
Corps émetteur de lumière, unité source de lumière dans lequel il est utilisé, afficheur et dispositif d'éclairage Download PDFInfo
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- WO2017221777A1 WO2017221777A1 PCT/JP2017/021903 JP2017021903W WO2017221777A1 WO 2017221777 A1 WO2017221777 A1 WO 2017221777A1 JP 2017021903 W JP2017021903 W JP 2017021903W WO 2017221777 A1 WO2017221777 A1 WO 2017221777A1
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- light
- color conversion
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Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
- H01L33/502—Wavelength conversion materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/02—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor bodies
- H01L33/26—Materials of the light emitting region
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Definitions
- the present invention relates to a light emitter, a light source unit, a display, and a lighting device.
- a light-emitting element using a light-emitting diode (LED, Light Emitting Diode) as a light source and using a color conversion method is used as a light source unit such as a lighting device or a backlight unit, or a member of a display.
- Color conversion is conversion of light emitted from a light source into light having a longer wavelength. For example, blue light emission can be converted into green light emission or red light emission.
- phosphors suitable for each chip are installed on the LED chip, and the emission wavelength is converted.
- a method of installing a yellow phosphor on an LED chip that emits blue light hereinafter referred to as a blue LED chip as appropriate
- a method of installing a red phosphor and a green phosphor on a blue LED chip and ultraviolet light
- a method of installing a red phosphor, a green phosphor and a blue phosphor on the emitting LED chip has been proposed.
- Patent Document 1 A technique using a pyromethene compound is disclosed as a color conversion material that has excellent durability, high conversion efficiency, absorbs ultraviolet light to visible light, and emits red light with high luminance (for example, Patent Document 1). To 2).
- JP 2011-241160 A Japanese Patent Application Laid-Open No. 2014-136771
- Patent Documents 1 and 2 disclose that a composition containing a pyromethene compound is molded into a film and used as a color conversion filter.
- a light emitting body in which such a wavelength conversion filter is bonded directly on a blue LED chip has insufficient durability, and cannot be used as a backlight light source for illumination, LCD, and the like.
- an object of the present invention is to provide a light emitter that is excellent in durability and can be used for a backlight light source such as an illumination or LCD.
- the present inventor presumed that the above-mentioned problems of the prior art were due to deterioration of the pyromethene compound.
- the durability of the light emitter can be improved by studying the structure of the light emitter under the assumption that such deterioration may be due to the effect of heat generated by the long-time driving of the LED chip. I found.
- the present invention is a light emitter having an LED and a color conversion layer, wherein the color conversion layer includes an organic light emitting material, and a resin layer is provided between the LED and the color conversion layer. , A light emitter.
- a light emitter having excellent durability can be obtained.
- a light source unit, a display, and a lighting device having excellent durability can be obtained using such a light emitter.
- the light emitter according to the embodiment of the present invention includes an LED and a color conversion layer, the color conversion layer includes an organic light emitting material, and includes a resin layer between the blue LED and the color conversion layer.
- the resin layer between the LED and the color conversion layer By having the resin layer between the LED and the color conversion layer, the temperature increase of the color conversion layer can be suppressed even if the LED is driven for a long time. Thereby, since deterioration of an organic luminescent material can be suppressed, the light-emitting body excellent in durability can be obtained.
- FIG. 1 is a side view showing an example of a light emitter according to an embodiment of the present invention.
- an LED 2 that emits blue light is mounted on a substrate 1, the LED 2 and the substrate 1 are electrically connected by a wire 3, and a reflector 4 is formed around the LED 2.
- the color conversion layer 5 containing an organic light emitting material is disposed in a recess formed by the reflector 4, and has a resin layer 6 between the LED 2 and the color conversion layer 5.
- the concave portion formed by the reflector 4 is molded with the resin layer 6, and the color conversion layer 5 is provided thereon.
- the color conversion layer 5 has a laminated structure of the color conversion layer 5a and the color conversion layer 5b.
- the upper surface of the color conversion layer 5 is lower than the upper surface of the reflector 4 in the embodiment according to FIG.
- the heat dissipation layer 7 is included.
- the substrate is constituted by the heat dissipating substrate 8 in the embodiment according to FIG. 1 (a).
- a lens 9 is further formed on the reflector 4 and the color conversion layer 5 in the embodiment according to FIG. 1 (a).
- the reflector 4 is not provided in the embodiment according to FIG. 1 (a).
- 1 (a) to 1 (g) are examples of a light emitting body equipped with a wire bonding type LED, the use of a flip chip type LED does not impair the effect of the present invention.
- the color conversion layer in the present invention contains an organic light emitting material.
- the color conversion layer may contain a resin and other additives as necessary.
- the color conversion layer is a longer part of the light emitted from the LED, preferably the light whose peak wavelength is observed in the wavelength range of 400 nm or more and 500 nm or less (hereinafter referred to as “blue light emission” as appropriate). It has a function to convert light into wavelengths.
- the converted light is observed, for example, in light emission observed in a region having a peak wavelength of 500 nm or more and 580 nm or less (hereinafter referred to as “green light emission” as appropriate) or in a region having a peak wavelength of 580 nm or more and 750 nm or less.
- Light emission hereinafter referred to as “red light emission” as appropriate).
- part of the light emitted from the LED as described above passes through the color conversion layer. By adjusting the wavelength and intensity of these lights, light of a desired color such as white light can be obtained.
- the organic light emitting material in the present invention refers to a material that emits light having a wavelength different from that of light when irradiated with some light.
- the organic light emitting material is an organic light emitting material.
- organic light emitting material for example, Compounds having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene and derivatives thereof; Furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine
- a compound having a heteroaryl ring such as Borane derivatives; 1,4-distyrylbenzene, 4,4′-bis (2- (4-diphenylaminophenyl
- At least one organic luminescent material is included in the color changing layer, and two or more organic luminescent materials may be included.
- the organic light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, but a fluorescent light emitting material is preferable in order to achieve high color purity.
- a compound having a condensed aryl ring and a derivative thereof are preferable because of high thermal stability and light stability.
- the organic light emitting material is preferably a compound having a coordination bond from the viewpoint of solubility and diversity of molecular structure.
- a compound containing boron such as a boron fluoride complex is also preferable in that the half width is small and highly efficient light emission is possible.
- a pyromethene derivative is preferable in terms of giving a high emission quantum yield and good durability. More preferably, it is a compound represented by the general formula (1), that is, a pyromethene compound.
- R 1 to R 9 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, Aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl group , A phosphine oxide group, and a condensed ring and an aliphatic ring formed between adjacent substituents.
- hydrogen may be deuterium.
- a substituted or unsubstituted aryl group having 6 to 40 carbon atoms is 6 to 40 including the carbon number contained in the substituent substituted on the aryl group.
- the substituents in the case of substitution include alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups.
- Aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl Group and a phosphine oxide group are preferable, and specific substituents that are preferable in the description of each substituent are preferable. Moreover, these substituents may be further substituted with the above-mentioned substituents.
- substituted means that a hydrogen atom or a deuterium atom is substituted.
- substituted or unsubstituted means that a hydrogen atom or a deuterium atom is substituted.
- substituted or unsubstituted is the same as described above.
- the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group, which is a substituent. It may or may not have. There are no particular limitations on the additional substituent when it is substituted, and examples thereof include an alkyl group, a halogen, an aryl group, a heteroaryl group, and the like, and this point is common to the following description. Further, the number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
- the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, which may or may not have a substituent.
- the carbon number of the cycloalkyl group other than the substituent is not particularly limited, but is preferably in the range of 3 to 20.
- the heterocyclic group refers to an aliphatic ring having an atom other than carbon, such as a pyran ring, piperidine ring, or cyclic amide, in the ring, which may or may not have a substituent. Good. Although carbon number of a heterocyclic group is not specifically limited, Preferably it is the range of 2-20.
- alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have a substituent.
- carbon number of an alkenyl group is not specifically limited, Preferably it is the range of 2-20.
- the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, and the like, which may have a substituent. It may not have.
- the alkynyl group indicates, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
- carbon number of an alkynyl group is not specifically limited, Preferably it is the range of 2-20.
- An alkoxy group refers to a functional group to which an aliphatic hydrocarbon group is bonded via an ether bond, such as a methoxy group, an ethoxy group, or a propoxy group, and the aliphatic hydrocarbon group has a substituent. May not be included.
- carbon number of an alkoxy group is not specifically limited, Preferably it is the range of 1-20.
- the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
- the hydrocarbon group of the alkylthio group may or may not have a substituent. Although carbon number of an alkylthio group is not specifically limited, Preferably it is the range of 1-20.
- An aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. Good. Although carbon number of an aryl ether group is not specifically limited, Preferably, it is the range of 6-40.
- the aryl thioether group is a group in which an oxygen atom of an ether bond of an aryl ether group is substituted with a sulfur atom.
- the aromatic hydrocarbon group in the aryl ether group may or may not have a substituent. Although carbon number of an aryl ether group is not specifically limited, Preferably, it is the range of 6-40.
- the aryl group is, for example, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, benzophenanthryl group, benzoanthracene group.
- An aromatic hydrocarbon group such as a nyl group, a chrycenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzoanthracenyl group, a perylenyl group, or a helicenyl group is shown.
- a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are preferable.
- the aryl group may or may not have a substituent. Although carbon number of an aryl group is not specifically limited, Preferably it is 6-40, More preferably, it is the range of 6-30.
- the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group or an anthracenyl group, and a phenyl group or a biphenyl group
- a terphenyl group and a naphthyl group are more preferable, a phenyl group, a biphenyl group, and a terphenyl group are more preferable, and a phenyl group is particularly preferable.
- the aryl group of the substituent is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, A phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group are more preferable. Particularly preferred is a phenyl group.
- the heteroaryl group is, for example, pyridyl group, furanyl group, thiophenyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridazinyl group, triazinyl group, naphthyridinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, Benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indolocarbazolyl group, benzofurocarbazolyl group, benzothienocarba Zolyl group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl group, dibenzoacridin
- the naphthyridinyl group is any of 1,5-naphthyridinyl group, 1,6-naphthyridinyl group, 1,7-naphthyridinyl group, 1,8-naphthyridinyl group, 2,6-naphthyridinyl group, and 2,7-naphthyridinyl group.
- the heteroaryl group may or may not have a substituent. Although carbon number of a heteroaryl group is not specifically limited, Preferably it is 2-40, More preferably, it is the range of 2-30.
- the heteroaryl group includes a pyridyl group, furanyl group, thiophenyl group, quinolinyl group, pyrimidyl group, triazinyl group, benzofuranyl group, benzothiophenyl group, indolyl group , A dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, and a phenanthrolinyl group, preferably a pyridyl group, a furanyl group, a thiophenyl group, and a quinolinyl group. More preferred. Particularly preferred is a pyridyl group.
- the heteroaryl group includes a pyridyl group, furanyl group, thiophenyl group, quinolinyl group, pyrimidyl group, triazinyl group, benzofuranyl group, benzothiophenyl group, indolyl group, Dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, phenanthrolinyl group are preferable, pyridyl group, furanyl group, thiophenyl group, quinolinyl group are more A pyridyl group is particularly preferable.
- Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.
- the carbonyl group, carboxyl group, oxycarbonyl group and carbamoyl group may or may not have a substituent.
- substituents include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.
- An amino group is a substituted or unsubstituted amino group.
- substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group.
- aryl group and heteroaryl group a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group are preferable. These substituents may be further substituted.
- the number of carbon atoms of the substituent portion of the amino group is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.
- silyl groups include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, propyldimethylsilyl groups, vinyldimethylsilyl groups, and other alkylsilyl groups, phenyldimethylsilyl groups, tert-butyldiphenylsilyl groups, An arylsilyl group such as a phenylsilyl group or a trinaphthylsilyl group is shown. Substituents on the silicon atom may be further substituted. Although carbon number of a silyl group is not specifically limited, Preferably it is the range of 1-30.
- Siloxanyl group refers to a silicon compound group via an ether bond, such as trimethylsiloxanyl group. Substituents on the silicon atom may be further substituted.
- the boryl group is a substituted or unsubstituted boryl group.
- substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, an alkoxy group, and a hydroxyl group, and among them, an aryl group and an aryl ether group are preferable.
- the phosphine oxide group is a group represented by —P ( ⁇ O) R 10 R 11 .
- R 10 R 11 is selected from the same group as R 1 to R 9 .
- the condensed ring formed between adjacent substituents means that any adjacent two substituents (for example, R 1 and R 2 in the general formula (1)) are bonded to each other to form a conjugated or non-conjugated cyclic skeleton. It means forming.
- an element selected from nitrogen, oxygen, sulfur, phosphorus and silicon may be included. Further, the condensed ring may be further condensed with another ring.
- the compound represented by the general formula (1) exhibits a high emission quantum yield and has a small peak half-value width of the emission spectrum, so that efficient color conversion and high color purity can be achieved.
- the compound represented by the general formula (1) introduces an appropriate substituent at an appropriate position, so that various properties such as light emission efficiency, color purity, thermal stability, light stability and dispersibility can be obtained. And physical properties can be adjusted.
- R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted alkyl group, substituted or unsubstituted, compared to when R 1 , R 3 , R 4 and R 6 are all hydrogen.
- the aryl group is a substituted or unsubstituted heteroaryl group, higher thermal stability and light stability are exhibited.
- examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Preferred are alkyl groups having 1 to 6 carbon atoms such as sec-butyl group, tert-butyl group, pentyl group, hexyl group, and further excellent thermal stability. Therefore, methyl group, ethyl group, n-propyl group, isopropyl group are preferred. N-butyl group, sec-butyl group, and tert-butyl group are preferable. Further, from the viewpoint of preventing concentration quenching and improving the emission quantum yield, a sterically bulky tert-butyl group is more preferable. A methyl group is also preferably used from the viewpoint of ease of synthesis and availability of raw materials.
- the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group. A group is more preferable, and a phenyl group is particularly preferable.
- the heteroaryl group is preferably a pyridyl group, a quinolinyl group or a thiophenyl group, and a pyridyl group or a quinolinyl group is preferred. More preferred is a pyridyl group.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and are preferably substituted or unsubstituted alkyl groups.
- the compound represented by the general formula (1) has good solubility in a resin or a solvent.
- the alkyl group is preferably a methyl group from the viewpoint of ease of synthesis and availability of raw materials.
- R 1 , R 3 , R 4 and R 6 may all be the same or different and are preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. In these cases, the compound represented by the general formula (1) exhibits higher thermal stability and light stability.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and more preferably a substituted or unsubstituted aryl group.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and in the case of a substituted or unsubstituted aryl group, for example, R 1 ⁇ R 4 , R 3 ⁇ R 6 , R It is preferable to introduce a plurality of types of substituents such as 1 ⁇ R 3 or R 4 ⁇ R 6 .
- “ ⁇ ” indicates a group having a different structure.
- R 1 ⁇ R 4 indicates that R 1 and R 4 are groups having different structures.
- R 1 ⁇ R 3 or R 4 ⁇ R 6 is preferable in terms of improving the light emission efficiency and the color purity in a balanced manner.
- one or more aryl groups that affect the color purity are introduced into both pyrrole rings, and the aryl group that affects the efficiency at other positions. Therefore, both properties can be improved to the maximum.
- an aryl group substituted with an electron donating group is preferable.
- the electron donating group is an atomic group that donates electrons to a substituted atomic group by an induced effect or a resonance effect in organic electronic theory.
- Examples of the electron donating group include those having a negative value as the Hammett's rule substituent constant ( ⁇ p (para)).
- the Hammett's rule substituent constant ( ⁇ p (para)) can be cited from the Chemical Handbook, Basic Revision 5 (II-380).
- the electron donating group examples include an alkyl group ( ⁇ p of methyl group: ⁇ 0.17) and an alkoxy group ( ⁇ p of methoxy group: ⁇ 0.27).
- an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferable, and a methyl group, an ethyl group, a tert-butyl group, or a methoxy group is more preferable. From the viewpoint of dispersibility, a tert-butyl group and a methoxy group are particularly preferable.
- the substitution position of the substituent is not particularly limited, it is necessary to suppress the twisting of the bond in order to increase the light stability of the compound represented by the general formula (1). It is preferable to bond to the position or para position.
- an aryl group having a bulky substituent such as a tert-butyl group, an adamantyl group, or a methoxy group is preferable.
- R 1 , R 3 , R 4 and R 6 may be the same or different, and in the case of a substituted or unsubstituted aryl group, R 1 , R 3 , R 4 and R 6 are all the same or different. It may be a substituted or unsubstituted phenyl group. In this case, they are more preferably selected from the following Ar-1 to Ar-6, respectively. In this case, preferred combinations of R 1 , R 3 , R 4 and R 6 include those shown in Table 1-1 to Table 1-11, but are not limited thereto.
- R 2 and R 5 are preferably any one of hydrogen, an alkyl group, a carbonyl group, an oxycarbonyl group, and an aryl group.
- hydrogen or an alkyl group is preferable from the viewpoint of thermal stability, and hydrogen is more preferable from the viewpoint of easily obtaining a narrow half-value width in the emission spectrum.
- R 8 and R 9 are preferably an alkyl group, aryl group, heteroaryl group, fluorine, fluorine-containing alkyl group, fluorine-containing heteroaryl group or fluorine-containing aryl group.
- R 8 and R 9 are more preferably fluorine or a fluorine-containing aryl group because they are stable against excitation light and a higher fluorescence quantum yield is obtained.
- R 8 and R 9 are more preferably fluorine in view of ease of synthesis.
- the fluorine-containing aryl group is an aryl group containing fluorine, and examples thereof include a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group.
- the fluorine-containing heteroaryl group is a heteroaryl group containing fluorine, and examples thereof include a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group.
- the fluorine-containing alkyl group is an alkyl group containing fluorine, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.
- X is preferably C—R 7 from the viewpoint of light stability.
- the substituent R 7 greatly affects the durability of the compound represented by the general formula (1), that is, the decrease in the emission intensity of this compound over time.
- R 7 is hydrogen
- the reactivity of this hydrogen is high, so that this site easily reacts with moisture and oxygen in the air. This causes decomposition of the compound represented by the general formula (1).
- R 7 is a substituent having a large degree of freedom of movement of a molecular chain such as an alkyl group, for example, the reactivity is certainly lowered, but the compounds aggregate with time in the composition. In particular, the emission intensity is reduced due to concentration quenching.
- R 7 is preferably a group that is rigid and has a low degree of freedom of movement and does not easily cause aggregation. Specifically, R 7 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Either is preferable.
- X is C—R 7 and R 7 is a substituted or unsubstituted aryl group.
- aryl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, and an anthracenyl group are preferable from the viewpoint of not impairing the emission wavelength.
- R 7 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.
- a phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted terphenyl group are more preferable. Particularly preferred is a substituted or unsubstituted phenyl group.
- R 7 is preferably a moderately bulky substituent.
- R 7 has a certain amount of bulkiness, aggregation of molecules can be prevented. As a result, the luminous efficiency and durability of the compound represented by the general formula (1) are further improved.
- a more preferable example of such a bulky substituent includes a structure represented by the following general formula (2).
- r 1 is hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, hetero group It is selected from the group consisting of an aryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group.
- k is an integer of 1 to 3. When k is 2 or more, r 1 may be the same or different.
- r 1 is preferably a substituted or unsubstituted aryl group.
- aryl groups a phenyl group and a naphthyl group are particularly preferable examples.
- k in the general formula (2) is preferably 1 or 2, and k is more preferably 2 from the viewpoint of further preventing aggregation of molecules.
- k is 2 or more, it is preferable that at least one of r 1 is substituted with an alkyl group.
- the alkyl group in this case, a methyl group, an ethyl group, and a tert-butyl group are particularly preferable from the viewpoint of thermal stability.
- r 1 may be a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen.
- a methyl group, an ethyl group, a tert-butyl group, and a methoxy group are more preferable.
- a tert-butyl group and a methoxy group are particularly preferable.
- the fact that r 1 is a tert-butyl group or a methoxy group is more effective for preventing quenching due to aggregation between molecules.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and are groups represented by the following general formula (3). It is more preferable. Thereby, both luminous efficiency and color purity can be achieved.
- r 2 is selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxy group, and an alkylthio group.
- m is an integer of 1 to 3. When m is 2 or more, each r 2 may be the same or different. However, R 1 ⁇ R 3 or R 4 ⁇ R 6 . Here, ⁇ indicates a group having a different structure.
- R 7 is an aryl group or a heteroaryl group.
- R 1 to R 7 is an electron withdrawing group.
- R 1 to R 6 is an electron withdrawing group
- R 7 is an electron withdrawing group
- R 7 is preferably an electron withdrawing group.
- the electron-withdrawing group is also called an electron-accepting group, and is an atomic group that attracts electrons from a substituted atomic group by an induced effect or a resonance effect in organic electron theory.
- Examples of the electron withdrawing group include those having a positive value as the Hammett's rule substituent constant ( ⁇ p (para)).
- the Hammett's rule substituent constant ( ⁇ p (para)) can be cited from the Chemical Handbook, Basic Revision 5 (II-380).
- a phenyl group also has the example which takes the above positive values, in this invention, a phenyl group is not contained in an electron withdrawing group.
- electron withdrawing groups include, for example, -F ( ⁇ p: +0.06), -Cl ( ⁇ p: +0.23), -Br ( ⁇ p: +0.23), -I ( ⁇ p: +0.18), -CO 2 R 12 ( ⁇ p: when R 12 is an ethyl group +0.45), -CONH 2 ( ⁇ p: +0.38), -COR 12 ( ⁇ p: when R 12 is a methyl group +0.49),- Examples include CF 3 ( ⁇ p: +0.50), —SO 2 R 12 ( ⁇ p: +0.69 when R 12 is a methyl group), —NO 2 ( ⁇ p: +0.81), and the like.
- R 12 each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted
- a substituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms are represented. Specific examples of these groups include the same examples as described above.
- Preferred electron withdrawing groups include fluorine, fluorine-containing aryl groups, fluorine-containing heteroaryl groups, fluorine-containing alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups, substituted or unsubstituted amide groups, Examples thereof include a substituted or unsubstituted sulfonyl group or a cyano group. This is because they are difficult to chemically decompose.
- More preferred electron withdrawing groups include a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, or a cyano group. This is because these lead to effects of preventing concentration quenching and improving the emission quantum yield. Particularly preferred electron withdrawing groups are substituted or unsubstituted ester groups.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and each may be a substituted or unsubstituted alkyl group.
- X is C—R 7 and R 7 is a group represented by the general formula (2), particularly preferably, r is a group represented by the general formula (2), wherein r is a substituted or unsubstituted phenyl group. And the like.
- R 1 , R 3 , R 4 and R 6 may all be the same or different, and the above-mentioned Ar— 1 to Ar-6, X is C—R 7 , and R 7 is a group represented by the general formula (2).
- R 7 is more preferably a group represented by the general formula (2) in which r is a tert-butyl group or methoxy group, and represented by the general formula (2) in which r is a methoxy group. It is particularly preferred that
- the compound represented by the general formula (1) can be synthesized, for example, by the methods described in JP-T-8-509471 and JP-A-2000-208262. That is, the target pyromethene metal complex is obtained by reacting the pyromethene compound and the metal salt in the presence of a base.
- the compound represented by the general formula (1) can be synthesized.
- the following general formula (5) A method of reacting the represented compound in 1,2-dichloroethane in the presence of triethylamine to obtain the compound represented by the general formula (1) can be mentioned.
- R 1 to R 9 are the same as described above. J represents halogen.
- a method of generating a carbon-carbon bond by using a coupling reaction between a halogenated derivative and a boronic acid or a boronic acid esterified derivative can be mentioned.
- the present invention is not limited to this.
- introducing an amino group or a carbazolyl group for example, there is a method of generating a carbon-nitrogen bond by using a coupling reaction between a halogenated derivative and an amine or a carbazole derivative under a metal catalyst such as palladium.
- the present invention is not limited to this.
- the color conversion layer can contain other compounds as needed in addition to the compound represented by the general formula (1).
- an assist dopant such as rubrene may be contained in order to further increase the energy transfer efficiency from the excitation light to the compound represented by the general formula (1).
- a desired organic light emitting material for example, an organic light emitting material such as a coumarin dye or a rhodamine dye may be added. it can.
- known light-emitting materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots can be added in combination.
- organic light emitting materials other than the compound represented by the general formula (1) are shown below, but the present invention is not particularly limited to these.
- the color conversion layer preferably contains the following light emitting material (A) and light emitting material (B).
- the light-emitting material (A) is an organic light-emitting material that exhibits light emission (that is, green light emission) observed in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 400 nm or more and 500 nm or less. It is.
- the luminescent material (B) is observed in a region having a peak wavelength of 580 nm or more and 750 nm or less by being excited by at least one of excitation light having a wavelength of 400 nm or more and 500 nm or less and light emitted from the organic light emitting material (A). It is an organic light emitting material exhibiting emitted light (that is, red light emission).
- the light extracted from the light emitter is blue, green, A sharp emission spectrum is shown for each red color. Therefore, white light with good color purity can be obtained. As a result, especially in a display, the color gamut becomes larger and more vivid colors can be displayed.
- the overlap of emission spectra of blue, green and red colors is small.
- the lower limit value of the peak wavelength of the organic light emitting material (A) is more preferably 510 nm or more, further preferably 515 nm or more, and particularly preferably 520 nm or more.
- the upper limit value of the peak wavelength of the organic light emitting material (A) is more preferably 550 nm or less, further preferably 540 nm or less, and particularly preferably 530 nm or less.
- the lower limit of the peak wavelength of the organic light emitting material (B) is more preferably 620 nm or more, further preferably 630 nm or more, and particularly preferably 635 nm or more.
- the upper limit of the peak wavelength of red light may be 750 nm or less, which is near the upper limit of the visible range, but it is more preferably 700 nm or less from the viewpoint of increased visibility.
- the upper limit value of the peak wavelength of the organic light emitting material (B) is more preferably 680 nm or less, and particularly preferably 660 nm or less.
- the half-value widths of the emission spectra of blue, green and red are small.
- the half-value width of the emission spectrum of green light is preferably 50 nm or less, more preferably 40 nm or less, further preferably 35 nm or less, and particularly preferably 30 nm or less.
- the full width at half maximum of the emission spectrum of red light is preferably 80 nm or less, more preferably 70 nm or less, further preferably 60 nm or less, and particularly preferably 50 nm or less.
- the shape of the emission spectrum is not particularly limited, but is preferably a single peak. This is because the excitation energy can be used efficiently and the color purity becomes high.
- the single peak indicates a state where there is no peak having an intensity of 5% or more of the strongest peak in a certain wavelength region.
- the color conversion layer may be a single layer or a plurality of layers may be laminated. There is no particular limitation on the number of stacked layers in the case where a plurality of layers are stacked, but two layers are preferable. When a plurality of layers are stacked, at least two of them are preferably an a layer containing the organic light emitting material (A) and a b layer containing the organic light emitting material (B). When the organic light emitting materials (A) and (B) are contained in different layers, the interaction between the light emitting materials is suppressed. Therefore, it emits light with higher color purity than when they are dispersed in the same layer. Moreover, since the organic light emitting materials (A) and (B) emit light independently in each layer by suppressing the interaction between the light emitting materials, the green and red light emission peak wavelengths and light emission intensities can be adjusted. Easy.
- the stacking order of the a layer and the b layer There is no particular limitation on the stacking order of the a layer and the b layer.
- the a layer and the b layer may be in contact with each other or may be separated from each other.
- the organic light emitting material (B) is excited by light emission from the organic light emitting material (A) and emits light, it is preferable that the b layer is formed on the a layer.
- the content of the organic light-emitting material in the color conversion layer depends on the molar extinction coefficient of the compound, the fluorescence quantum yield and the absorption intensity at the excitation wavelength, and the thickness and transmittance of the sheet to be produced.
- the amount is preferably 1.0 ⁇ 10 ⁇ 4 parts by weight to 30 parts by weight per 100 parts by weight.
- the content of the organic light emitting material is more preferably 1.0 ⁇ 10 ⁇ 3 parts by weight to 10 parts by weight with respect to 100 parts by weight of the resin component, and 1.0 ⁇ 10 ⁇ 2 parts by weight to 5 parts by weight. Part by weight is particularly preferred.
- the color conversion layer contains both the organic light emitting material (A) that emits green light and the organic light emitting material (B) that emits red light
- the content w 2 of the organic light emitting material (B) is preferably a relationship of w 1 ⁇ w 2.
- w 1 and w 2 are weight percentages of the organic light emitting material relative to the weight of the resin component.
- the color conversion layer may contain a resin.
- This resin forms a continuous phase and may be any material that is excellent in molding processability, transparency, heat resistance, and the like.
- the resin include photo-curable resist materials having reactive vinyl groups such as acrylic, methacrylic, polyvinyl cinnamate, polyimide, and ring rubber, epoxy resins, silicone resins (silicone rubber, silicone gel, etc.
- Organopolysiloxane cured products (including crosslinked products), urea resins, fluororesins, polycarbonate resins, acrylic resins, methacrylic resins, polyimide resins, cyclic olefins, polyethylene terephthalate resins, polypropylene resins, polystyrene resins, urethane resins, melamines
- resins such as resins, polyvinyl resins, polyamide resins, phenol resins, polyvinyl alcohol resins, cellulose resins, aliphatic ester resins, aromatic ester resins, aliphatic polyolefin resins, aromatic polyolefin resins. Can. In addition, these resins can be used as the resin.
- epoxy resins silicone resins, acrylic resins, ester resins or mixtures thereof can be suitably used from the viewpoint of transparency, and silicone resins are preferably used from the viewpoint of heat resistance.
- the silicone resin may be either a thermosetting silicone resin or a thermoplastic silicone resin.
- the thermosetting silicone resin is cured at room temperature or 50 to 200 ° C. and is excellent in transparency, heat resistance and adhesiveness.
- thermosetting silicone resin is formed, for example, by a hydrosilylation reaction between a compound containing an alkenyl group bonded to a silicon atom and a compound having a hydrogen atom bonded to a silicon atom.
- alkenyl groups bonded to silicon atoms such as vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, propenyltrimethoxysilane, norbornenyltrimethoxysilane, and octenyltrimethoxysilane.
- thermosetting silicone resin other known ones as described in, for example, JP 2010-159411 A can be used.
- thermosetting silicone resin a commercially available one, for example, a general silicone sealing material for LED can be used. Specific examples thereof include OE-6630A / B and OE-6336A / B manufactured by Toray Dow Corning, and SCR-1012A / B and SCR-1016A / B manufactured by Shin-Etsu Chemical Co., Ltd.
- thermosetting silicone resin is preferably blended with a hydrosilylation reaction retarder such as acetylene alcohol in order to suppress curing at room temperature and lengthen the pot life.
- a hydrosilylation reaction retarder such as acetylene alcohol
- thermoplastic silicone resin is a resin that softens and exhibits fluidity when heated to a glass transition temperature or a melting point.
- the thermoplastic silicone resin does not undergo a chemical reaction such as a curing reaction even if heated and softened once, and thus becomes solid again when it returns to room temperature.
- thermoplastic silicone resin examples include commercially available RSN series such as RSN-0805 and RSN-0217 manufactured by Toray Dow Corning.
- the color conversion layer may contain an additive as long as the effects of the present invention are not impaired.
- additives include light stabilizers such as dispersion stabilizers, leveling agents, antioxidants, flame retardants, defoamers, plasticizers, crosslinking agents, curing agents, and UV absorbers.
- adhesion aids such as silane coupling agents.
- the color conversion layer may contain inorganic particles.
- the inorganic particles include fine particles composed of glass, titania, silica, alumina, silicone, zirconia, ceria, aluminum nitride, silicon carbide, silicon nitride, barium titanate, and the like. These may be used alone or in combination of two or more. From the viewpoint of easy availability, silica, alumina, titania and zirconia are preferred.
- the resin layer included between the LED and the color conversion layer is not particularly limited as long as it includes a resin and transmits light emitted from the LED.
- the resin layer is present, the color conversion layer and the LED are not in direct contact with each other, so that heat generated when the LED is driven is hardly transmitted to the color conversion layer, and the durability of the color conversion layer is improved.
- the color conversion layer and the resin layer may or may not be in direct contact, but from the viewpoint of making it difficult to transfer the heat generated by the LED to the color conversion layer, the color conversion layer and the resin layer are More preferably, it is not in direct contact, for example via an air layer.
- the same resin as that contained in the color conversion layer can be used.
- the resin include, for example, a photocurable resist material having a reactive vinyl group such as acrylic, methacrylic, polyvinyl cinnamate, polyimide, and ring rubber, epoxy resin, silicone resin (silicone rubber, Organopolysiloxane cured products (cross-linked products) such as silicone gel), urea resin, fluorine resin, polycarbonate resin, acrylic resin, methacrylic resin, polyimide resin, cyclic olefin, polyethylene terephthalate resin, polypropylene resin, polystyrene resin, urethane
- Known materials such as resin, melamine resin, polyvinyl resin, polyamide resin, phenol resin, polyvinyl alcohol resin, cellulose resin, aliphatic ester resin, aromatic ester resin, aliphatic polyolefin resin, aromatic polyolefin resin It is below.
- these resins can be used
- epoxy resins from the viewpoint of transparency, epoxy resins, silicone resins, acrylic resins, ester resins, or mixtures thereof can be suitably used.
- a silicone resin and an acrylic resin are preferable, and a silicone resin is more preferably used from the viewpoint of heat resistance.
- the silicone resin may be either a thermosetting silicone resin or a thermoplastic silicone resin.
- the thermosetting silicone resin is cured at room temperature or 50 to 200 ° C. and is excellent in transparency, heat resistance and adhesiveness.
- thermosetting silicone resin a commercially available one, for example, a general silicone sealing material for LED can be used. Specific examples thereof include OE-6630A / B and OE-6336A / B manufactured by Toray Dow Corning, and SCR-1012A / B and SCR-1016A / B manufactured by Shin-Etsu Chemical Co., Ltd.
- thermosetting silicone resin is preferably blended with a hydrosilylation reaction retarder such as acetylene alcohol in order to suppress curing at room temperature and lengthen the pot life.
- a hydrosilylation reaction retarder such as acetylene alcohol
- thermoplastic silicone resin is a resin that softens and exhibits fluidity when heated to a glass transition temperature or a melting point.
- the thermoplastic silicone resin does not undergo a chemical reaction such as a curing reaction even if heated and softened once, and thus becomes solid again when it returns to room temperature.
- thermoplastic silicone resin examples include commercially available products, for example, RSN series such as RSN-0805 and RSN-0217 manufactured by Toray Dow Corning.
- the thickness of the resin layer is preferably 50 ⁇ m or more, more preferably 100 ⁇ m or more, and even more preferably 150 ⁇ m or more from the viewpoint of enhancing the heat insulation.
- the upper limit of the thickness of the resin layer is not particularly limited, but is preferably 500 ⁇ m or less from the viewpoint of thinning.
- the resin layer preferably further includes a heat insulating material.
- the heat insulating material in the present invention is a material having lower thermal conductivity than the resin contained in the resin layer.
- the heat insulating material include foamed plastics such as urethane foam, phenol foam and polystyrene foam, porous particles and hollow particles. Since these materials have an air layer on the surface or inside of the particles, they are materials having low thermal conductivity and excellent heat insulation. When the resin layer contains these heat insulating materials, voids can be included in the resin layer, and the heat insulating properties of the resin layer can be improved. From the viewpoint of excellent light resistance, the heat insulating material is preferably hollow particles or porous particles.
- the porosity in the resin layer is preferably 30% or more, more preferably 40% or more, and further preferably 50% or more. Further, from the viewpoint of not reducing the transmittance of the resin layer, the porosity in the resin layer is preferably 90% or less.
- the porosity is a ratio of voids in the resin layer, and is a value measured by the following method. Polishing is performed so that the cross section of the color conversion layer is observed by any one of a mechanical polishing method, a microtome method, a CP (Cross-section Polisher) method, and a focused ion beam (FIB) processing method. The obtained cross section is observed with a scanning electron microscope (SEM, Scanning Electron Microscope), and the porosity is obtained from the obtained two-dimensional image.
- SEM scanning electron microscope
- the porosity is calculated according to the following procedure.
- an image obtained by SEM observation is read by image processing software such as ImageJ, and the image is converted to gray scale.
- the binarization process separates the voids into black and the portions other than the voids into white, and calculates the area of the black portion and the area of the white portion.
- the binarization process may be performed automatically or visually. By calculating (area of the black portion) / (area of the black portion + area of the white portion), the porosity can be obtained.
- ceramics such as glass, titania, silica, alumina, silicone, zirconia, ceria, aluminum nitride, silicon carbide, silicon nitride, barium titanate; acrylic, methacrylic, polycinnamic acid Photo-curable resist materials having reactive vinyl groups such as vinyl, polyimide, and ring rubber; epoxy resins, silicone resins (including cured organopolysiloxanes (crosslinked products) such as silicone rubber and silicone gel), urea Resin, fluorine resin, polycarbonate resin, acrylic resin, methacrylic resin, polyimide resin, cyclic olefin, polyethylene terephthalate resin, polypropylene resin, polystyrene resin, urethane resin, melamine resin, polyvinyl resin, polyamide resin, phenol resin, Polyvinyl alcohol resins, cellulose resins, aliphatic ester resins, aromatic ester resins, aliphatic polyole
- silica or resin is preferable as the matrix material, and acrylic resin is more preferable among the resins. From the viewpoint of heat resistance and light resistance, silica is more preferable as the base material.
- Silica as used herein refers to glass containing 50% by weight or more of silicon dioxide.
- the content of the heat insulating material in the resin layer is preferably 10% by volume or more, more preferably 30% by volume or more, and more preferably 50% by volume or more from the viewpoint of further improving heat insulating properties. Further preferred. In view of not reducing the light transmittance, the content of the heat insulating material is preferably 90% by volume or less.
- the light transmittance in the resin layer decreases, the luminance of the light emitter decreases. From the viewpoint of suppressing a decrease in luminance of the light emitter, the light transmittance in the resin layer is preferably 70% or more.
- the transmittance of the resin layer refers to the transmittance of the resin layer at a wavelength of 450 nm.
- the transmittance can be measured by the following procedure. First, a resin liquid containing a resin and a heat insulating material is prepared. It is coated on quartz glass with a slit die coater or the like, and then heated in an oven at 150 ° C. for 1 hour to produce a transmittance measurement sample.
- the transmittance at a wavelength of 450 nm can be obtained by measuring the transmittance of the transmittance measuring sample with a basic configuration using an integrating sphere attached to a spectrophotometer (U-4100 Spectrophotometer (manufactured by Hitachi, Ltd.)).
- the light emitted from the organic light emitting material included in the light emitter is refracted or reflected at the interface between the layers included in the light emitter.
- the light reflected within the light emitter repeats further reflection within the light emitter, and is finally extracted outside the light emitter.
- a part of the light is absorbed, resulting in light attenuation.
- the heat insulating particles can also serve as the light scattering particles. That is, light is scattered by the heat insulating particles contained in the resin layer, and the traveling direction of the light is changed, so that the light extraction efficiency to the outside of the light emitting body is improved. Thus, a decrease in luminance of the light emitter can be suppressed.
- the average particle size of the heat insulating material is preferably 0.01 ⁇ m or more, more preferably 0.1 ⁇ m or more. .
- the average particle diameter of the heat insulating material is preferably 50 ⁇ m or less, more preferably 10 ⁇ m or less, and more preferably 5 ⁇ m or less. More preferably.
- the average particle diameter of the heat insulating material is a median diameter represented by D50.
- D50 means the particle diameter measured by the following method. Polishing is performed so that the cross section of the resin layer is observed by any one of a mechanical polishing method, a microtome method, a CP (Cross-section Polisher) method, and a focused ion beam (FIB) processing method. The obtained cross section is observed with an SEM, and the “individual particle diameter of particles” defined below is measured from the obtained two-dimensional image. Among the arbitrary straight lines that intersect the outer edge of the particle at two points, the one that maximizes the distance between the two intersections is selected, and the distance is defined as “individual particle diameter of the particle”.
- the particle size distribution is determined from the individual particle diameters of all the observed particles. In this distribution, the particle diameter of 10% of the accumulated part from the small particle diameter side is D10, the particle diameter of 50% of the accumulated part is D50, and the passing part. The particle diameter with an integrated 90% is defined as D90.
- the hollow particles which are one of the preferred forms of the heat insulating material are not particularly limited, and examples thereof include hollow silica particles, hollow alumina particles, hollow zirconia particles, hollow carbon particles, and hollow acrylic particles. These can use what is marketed.
- hollow silica particles include XG series such as XG40 and XG100 manufactured by Grandex, Silax manufactured by Nittetsu Mining Co., Ltd., Glass Bubbles S60-HS, Glass Bubbles S22, Glass Bubbles manufactured by Nittetsu Mining Co., Ltd. S38, Glass Bubbles series such as Glass Bubbles K20, Fuji Balloon series such as HSC-110C manufactured by Potters Ballotini, Sphericel 60P18, Fuji Balloon H-40 manufactured by Fuji Silysia Chemical Ltd., Fuji Balloon H-35, etc. Is mentioned.
- Specific examples of the hollow alumina particles include BW manufactured by Showa Denko.
- hollow zirconia particles include HOLLOW ZIRCONIUM SPHEES made by ZIRCOA.
- hollow carbon particles include clecas spheres manufactured by Kureha Chemical Co., Ltd., and carbo spheres manufactured by GENERAL TECHNOLOGIES.
- hollow acrylic particles include ADVANCEL HB-2051 manufactured by Sekisui Chemical Co., Ltd. Among these, hollow silica particles and hollow acrylic particles are more preferable, and hollow silica particles are particularly preferable because the heat conductivity of the base material having a lower thermal conductivity is superior.
- porous particles which is one of the preferred forms of the heat insulating material, are not particularly limited, and examples thereof include porous silica particles and porous titania particles. These can use what is marketed.
- porous silica particles include Tosoh silica-based NIPGEL AY-603, NIPGEL BY-001, NIPGEL ER-100, NIPGEL AZ-260, NIPSIL SS50F, and other NIPGEL series and NIPSIL series, manufactured by Fuji Silysia Chemical Co., Ltd. , Silicia series such as Cylicia 436, Cylicia 446, Cylicia 476, Cylicia 430, and Cylicia 450, and Sunsphere series such as Sunsphere H31, Sunsphere H51, and Sunsphere H121 manufactured by AGC S-Tech.
- porous titania particles include TITAN MICRO BEAD AA-1515 manufactured by JGC Catalysts & Chemicals.
- porous silica particles are preferable because the thermal conductivity of the base material is smaller and the heat insulation is better.
- the resin layer may contain a foamable material.
- the expandable material include thermally expandable fine particles such as Sekisui Chemical Co., Ltd. Advancel EM series and Nippon Ferrite Co., Ltd. Expandel. These foamable materials may be used alone or in combination of two or more.
- LED Although there is no restriction
- the blue LED may have one type of emission peak or two or more types of emission peaks. From the viewpoint of improving the color reproduction range of the display and illumination, the blue LED preferably has one kind of emission peak.
- a plurality of LEDs having different emission peaks can be arbitrarily combined and used as an aggregate of light emitters.
- several LED may be mounted with respect to one light-emitting body.
- the lower limit of the emission peak wavelength is more preferably 430 nm or more, further preferably 440 nm or more, and particularly preferably 445 nm or more.
- the light emission observed in the region where the emission peak wavelength is 500 nm or less is 500 nm or less as the blue light emission.
- the upper limit value of the emission peak wavelength of the LED is more preferably 480 nm or less, further preferably 470 nm or less, and particularly preferably 465 nm or less.
- the half-value width of the emission peak wavelength of blue light is preferably 30 nm or less, and more preferably 25 nm or less.
- substrate there is no restriction
- substrate which consists of well-known materials, such as a glass epoxy resin, a metal material, and a ceramic material, can be used.
- the light emitting LED in the present invention is mounted on a heat dissipating substrate. Since the LED is mounted on the heat-radiating substrate, it is possible to efficiently dissipate the heat generated in the LED, and the temperature increase of the color conversion layer can be suppressed.
- the material of the heat dissipation substrate is not particularly limited as long as high heat dissipation is obtained.
- Specific examples of the heat dissipating substrate include aluminum, aluminum alloy, copper, copper alloy, and a ceramic substrate.
- the aluminum alloy include an Al—Zn—Mg—Cu-based duralumin alloy.
- aluminum alloys containing 1% or less of silicon, iron, copper, manganese, magnesium, chromium, zinc, titanium and the like.
- copper alloys include gilding metal, red brass, brass, phosphor bronze, munz metal, aluminum bronze, beryllium copper, foreign copper, white bronze, gunmetal and the like.
- the ceramic examples include alumina, zirconia, zinc oxide, barium titanate, hydroxyapatite, silicon carbide, silicon nitride, fluorite, lead zirconate titanate, and steatite.
- an aluminum substrate is preferable.
- each electrode of the LED is connected to the conductive region of the substrate without using a wire.
- a heat sink for the purpose of further improving heat dissipation.
- a heat sink that contacts the back surface of the substrate. Since a higher heat dissipation effect is obtained as the contact area between the substrate and the heat sink increases, it is preferable that substantially the entire back surface of the substrate is in contact with the heat sink.
- the heat sink is required to have a large heat capacity. Specific examples of the heat sink material include, for example, copper and aluminum.
- the light emitter according to the embodiment of the present invention preferably further has a light-transmitting heat dissipation layer above the color conversion layer.
- the light-transmitting heat dissipation layer is a layer mainly containing a resin and heat conductive particles, and has a property of transmitting 50% or more of light having a wavelength of 450 nm. Part of the blue light irradiated to the color conversion layer is absorbed by the organic light-emitting material and converted into light having a longer wavelength. At this time, part of the absorbed energy is converted into heat, so the color The temperature of the conversion layer rises.
- the transmittance of light having a wavelength of 450 nm is preferably 50% or more so as not to reduce the luminance of the light emitter.
- the same resin as that used for the color conversion layer can be used. Of these, silicone resins are preferred.
- the thermally conductive material a material having high thermal conductivity such as alumina, titania, zirconia, boron nitride, aluminum nitride, silicon carbide, or the like can be used. Of these, alumina, titania and aluminum nitride are preferable.
- the light emitter according to the embodiment of the present invention preferably has a reflector, and the LED and the color conversion layer are preferably arranged in a recess formed by the reflector.
- the reflector constituting the recess is preferably inclined so as to spread on the opening side (the side far from the LED mounting surface).
- the inclination angle in this case is not particularly limited, and may be about 90 to 45 ° with respect to the upper surface of the substrate on which the LED is mounted.
- resins such as thermosetting resins and thermoplastic resins.
- resins such as thermosetting resins and thermoplastic resins.
- epoxy resin silicone resin, polyimide resin, modified polyimide resin, polyphthalamide resin, polycarbonate resin, polyphenylene sulfide resin, liquid crystal polymer, ABS resin, phenol resin, acrylic resin, PBT resin, and the like can be given.
- thermosetting resin an epoxy resin, a modified epoxy resin, a silicone resin, a modified silicone resin and the like are preferable.
- the reflector may contain inorganic particles such as titanium dioxide.
- the reflectance of the reflector is preferably 80% or more, more preferably 90% or more, and further preferably 95% or more.
- the recess formed by the reflector means a region from the substrate surface on which the LED is mounted to the upper surface of the reflector, and a region other than the reflector.
- the shape of the recess formed by the reflector is not particularly limited, and may be any of a columnar shape, a cone shape, a truncated cone shape, a polygonal column shape, a polygonal pyramid shape, a polygonal frustum shape, or a shape similar to these.
- the side view type light emitting device preferably has a shape in which the concave portion extends in the longitudinal direction from the viewpoint of miniaturization, and in particular, the plan view is a quadrangle, a polygon that approximates a quadrangle, or an approximate shape. It is more preferable that the shape of the concave portion is a quadrangular pyramid shape spreading toward the upper part.
- FIGS. 2A and 2B are a cross-sectional view and a top view of an example of a light emitter in the present invention.
- the uppermost surface of the reflector is referred to as an opening 14 of the concave portion.
- the length in the longitudinal direction is referred to as the length 10 of the recess, and in the opening 14 of the recess, the length in the short direction is referred to as the width 11 of the recess.
- the length of the recess may be different along the short direction. In that case, it is preferable that the width becomes wider toward the center in the short direction, and the longest portion of the length in the short direction is referred to as the length of the recess.
- the width of the recess may be different along the longitudinal direction. In that case, it is preferable that the width becomes wider toward the center in the longitudinal direction, and the longest portion of the length in the short direction is referred to as the width of the recess.
- the bottom of the recess refers to the substrate surface portion of the recess.
- the longest portion of the length of the bottom of the recess in the longitudinal direction is referred to as a bottom length 12, and the longest portion of the length in the short direction of the bottom is referred to as a bottom width 13.
- the side-edge display LED need only be long enough to mount the LED on the substrate.
- the length of the recess is preferably 0.5 mm or more and 10 mm or less.
- the width of the recess is preferably 1 mm or less, more preferably 0.5 mm or less, and further preferably 0.3 mm or less from the viewpoint of thinning the display.
- the width of the recess is not particularly limited as long as it is a size that can accommodate the needle of the dispenser, and is preferably 0.05 mm or more from the viewpoint of productivity.
- the depth of the recess can be appropriately adjusted depending on the thickness of the LED to be mounted, the bonding method, and the like, and is preferably 0.1 mm or more and 3 mm or less.
- the length of the recess is preferably 0.5 mm or more and 10 mm or less as in the case of the side edge type display.
- the width of the recess does not need to be thin unlike the side edge type, but is preferably 10 mm or less from the viewpoint of light extraction efficiency.
- the width of the recess is not particularly limited as long as the dispenser needle can be accommodated, and is preferably 0.05 mm or more from the viewpoint of productivity.
- the light emitter according to the embodiment of the present invention may further include an auxiliary layer having a light diffusing function, a polarizing function, a toning function, a refractive index matching function, and the like according to a required function.
- LED2 is arrange
- FIG. 3A shows an example of wire bonding in which the electrode on the upper surface of the LED 2 and the wiring in the circuit included in the substrate 1 are connected by the wire 3.
- the electrode surface of the LED is opposed to the wiring of the circuit board and connected by batch bonding.
- FIG. 3B shows the resin composition injected into the recess formed by the reflector 4 to form the resin layer 6.
- FIG.3 (b) shows the case where a part of recessed part formed with the reflector 4 is filled with a resin composition, it is not restricted to this, You may fill all the recessed parts with a resin composition.
- the resin composition can be produced as follows. After a predetermined amount of resin, solvent, heat insulating material, additive and the like are mixed, they are uniformly mixed and dispersed by a stirrer / kneader such as a homogenizer, a self-revolving stirrer, a three-roller, a ball mill, a planetary ball mill, or a bead mill. After mixing / dispersing or in the process of mixing / dispersing, defoaming may be performed under vacuum or reduced pressure conditions. Further, a specific component may be mixed in advance, or the mixture may be subjected to a treatment such as aging. It is also possible to remove part or all of the solvent in the mixture by an evaporator to obtain a desired solid content concentration.
- a stirrer / kneader such as a homogenizer, a self-revolving stirrer, a three-roller, a ball mill, a planetary ball mill, or a bead
- the solvent is not particularly limited as long as the viscosity of the fluidized resin can be adjusted.
- toluene, methyl ethyl ketone, methyl isobutyl ketone, hexane, acetone, terpineol, texanol, methyl cellosolve, butyl carbitol, butyl carbitol acetate, propylene glycol monomethyl ether acetate and the like can be mentioned. It is also possible to use a mixture of two or more of these solvents.
- the resin layer 6 is formed by drying or thermosetting the resin composition injected into the recess. Drying and thermosetting can be performed using a general heating device such as a hot air dryer or an infrared dryer. In this case, the drying and thermosetting conditions are usually 40 to 200 ° C. for 1 minute to 3 hours, preferably 80 ° C. to 150 ° C. for 2 minutes to 1 hour. In order to remove moisture, oxygen and the like dissolved in the resin composition before the step of drying or thermosetting the resin composition, the resin composition may be left in a vacuum atmosphere.
- the color conversion layer 5 is formed on the resin layer 6.
- the color conversion layer 5 may be formed using a composition in a solution state (hereinafter, a composition for forming the color conversion layer is appropriately referred to as “color conversion composition”), or a color conversion composition in advance. You may form using the sheet-like material (henceforth a "color conversion sheet” suitably) of the color conversion composition which shape
- the color conversion composition can be prepared as follows. After mixing a predetermined amount of the compound represented by the general formula (1), resin, solvent, additive, etc., with a stirrer / kneader such as a homogenizer, a self-revolving stirrer, three rollers, a ball mill, a planetary ball mill, or a bead mill. Mix and disperse homogeneously. After mixing / dispersing or in the process of mixing / dispersing, defoaming may be performed under vacuum or reduced pressure conditions. Further, a specific component may be mixed in advance, or the mixture may be subjected to a treatment such as aging. It is also possible to remove part or all of the solvent in the mixture by an evaporator to obtain a desired solid content concentration.
- a stirrer / kneader such as a homogenizer, a self-revolving stirrer, three rollers, a ball mill, a planetary ball mill, or a bead mill.
- the solvent is not particularly limited as long as it can adjust the viscosity of the resin in a fluid state and does not affect the deterioration of the compound represented by the general formula (1).
- toluene methyl ethyl ketone, methyl isobutyl ketone, hexane, acetone, terpineol, texanol, methyl cellosolve, butyl carbitol, butyl carbitol acetate, propylene glycol monomethyl ether acetate and the like can be mentioned. It is also possible to use a mixture of two or more of these solvents. Among these solvents, particularly toluene is preferably used because it does not affect the deterioration of the compound represented by the general formula (1) and there is little residual solvent after drying.
- the color conversion layer 5 can be formed by drying or thermosetting it. Drying and thermosetting can be performed using a general heating device such as a hot air dryer or an infrared dryer. In this case, the drying and thermosetting conditions are usually 40 to 200 ° C. for 1 minute to 3 hours, preferably 80 ° C. to 150 ° C. for 2 minutes to 1 hour.
- the sheet method can also be used for forming the color conversion layer.
- the sheet method is a method of sticking a color conversion sheet on a resin layer.
- the color conversion sheet can be prepared by applying a color conversion composition on a substrate and drying it.
- Application is reverse roll coater, blade coater, lip die coater, slit die coater, direct gravure coater, offset gravure coater, kiss coater, screen printing, natural roll coater, air knife coater, roll blade coater, two stream coater, rod coater, It can be performed with a wire bar coater, applicator, dip coater, curtain coater, spin coater, knife coater, or the like.
- a slit die coater In order to make the film thickness of the color conversion sheet uniform, it is preferably applied by a slit die coater.
- the color conversion sheet can be dried using a general heating device such as a hot air dryer or an infrared dryer.
- the heat curing conditions are usually 40 to 200 ° C. for 1 minute to 3 hours, preferably 80 ° C. to 150 ° C. for 2 minutes to 1 hour. If the color conversion sheet contains the layer obtained by hardening
- the thickness of the color conversion sheet is preferably 500 ⁇ m or less, more preferably 300 ⁇ m or less, and even more preferably 200 ⁇ m or less from the viewpoint of improving heat resistance.
- the film thickness measurement method is the film thickness (average film thickness) measured based on the thickness measurement method A by mechanical scanning in JIS K7130 (1999) plastic-film and sheet-thickness measurement method. Say.
- the base material used for the color conversion sheet is not particularly limited, and a known metal, film, glass, ceramic, paper, or the like can be used.
- the substrate is a metal plate
- the surface may be subjected to a plating treatment such as chromium or nickel, or a ceramic treatment.
- glass and resin films are preferably used because of the ease of producing and forming the color conversion sheet. Moreover, a film with high strength is preferable so that there is no fear of breakage when handling a film-like substrate.
- Resin films are preferable in terms of their required characteristics and economy, and among these, in terms of economy and handling, they are made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyphenylene sulfide, polycarbonate, and polypropylene. A plastic film selected from the group is preferred.
- the color conversion sheet can be press-molded at a high temperature of 200 ° C. or higher by an extruder.
- the base material in this case is preferably a polyimide film in terms of heat resistance.
- the surface of the base material may be subjected to a mold release treatment in advance for ease of peeling.
- the base material has a transparency surface and the film which consists of PET, PEN, and a polycarbonate is preferable.
- the thickness of the substrate is not particularly limited, but the lower limit is preferably 25 ⁇ m or more, and more preferably 38 ⁇ m or more. Moreover, as an upper limit, 5000 micrometers or less are preferable and 3000 micrometers or less are more preferable.
- a barrier layer may be formed on the base film for the purpose of improving the gas barrier property with respect to the color conversion layer.
- the barrier layer include silicon oxide, aluminum oxide, tin oxide, indium oxide, yttrium oxide, magnesium oxide, or a mixture thereof, or a metal oxide thin film obtained by adding other elements to these, or polyvinylidene chloride, Examples include, but are not limited to, films made of various resins such as acrylic resins, silicone resins, melamine resins, urethane resins, and fluorine resins.
- the film having a barrier function against moisture examples include, for example, polyethylene, polypropylene, nylon, polyvinylidene chloride, vinylidene chloride and vinyl chloride, copolymers of vinylidene chloride and acrylonitrile, and various resins such as fluorine resins.
- membrane can be mentioned, it is not limited to these.
- antireflection function antiglare function
- antireflection antiglare function hard coat function (anti-friction function)
- antistatic function antifouling function
- electromagnetic wave shielding function infrared ray
- An auxiliary layer having a cut function, an ultraviolet ray cut function, a polarization function, and a toning function may be further provided.
- the color conversion sheet preferably has a storage elastic modulus at 25 ° C. of 0.1 MPa or more and 2 GPa or less. By being in the said range, cutting processes, such as individualization, can be easily performed with respect to a color conversion sheet.
- the storage elastic modulus at 25 ° C. is 0.1 MPa or more, it is possible to ensure the hardness for performing stable cutting.
- the storage elastic modulus at 25 ° C. is 2 GPa or less, so that it is possible to prevent the color conversion sheet from being cracked during the cutting process. The required storage modulus.
- Dynamic viscoelasticity means that when shear strain is applied to a material at a sinusoidal frequency, the shear stress that appears when a steady state is reached is divided into a component (elastic component) whose strain and phase match, and the strain and phase are
- a component elastic component
- the strain and phase are
- G ′ storage elastic modulus
- the sheet method for forming the color conversion layer When using the sheet method for forming the color conversion layer, divide the color conversion sheet into a size required for each light emitter, pick up the singulated color conversion sheet, and attach it to the resin layer 6 Thus, the color conversion layer 5 is formed.
- a known adhesive may be used, or the resin layer 6 itself may be provided with adhesiveness and used as an adhesive.
- the resin layer 6 is used as an adhesive, the resin layer 6 is not completely cured when the resin layer 6 is formed, but is semi-cured and the resin layer 6 is completely cured after the color conversion sheet is attached. Both can be bonded.
- the method for dividing the color conversion sheet into individual pieces is not particularly limited, and methods such as punching with a mold, processing with a laser, and cutting with a blade are used.
- Processing with a laser imparts high energy, so it is very difficult to avoid burning of the resin and deterioration of the phosphor, and cutting with a blade is desirable.
- the cutting method with a blade there are a method of pushing and cutting a simple blade, and a method of cutting with a rotary blade, both of which can be suitably used.
- the method of forming a light-transmitting heat-dissipating layer includes a method using a resin composition as a material for the light-transmitting heat-dissipating layer. After mixing a predetermined amount of resin, solvent, heat conductive material, etc., the mixture is uniformly mixed and dispersed with a stirrer / kneader such as a homogenizer, self-revolving stirrer, 3-roller, ball mill, planetary ball mill, or bead mill. A resin composition for producing a light-radiating layer is obtained.
- a resin composition as a material for the light-transmitting heat-dissipating layer.
- defoaming may be performed under vacuum or reduced pressure conditions. Further, a specific component may be mixed in advance, or the mixture may be subjected to a treatment such as aging. It is also possible to remove part or all of the solvent in the mixture by an evaporator to obtain a desired solid content concentration.
- the solvent is not particularly limited as long as the viscosity of the fluidized resin can be adjusted.
- examples thereof include toluene, methyl ethyl ketone, methyl isobutyl ketone, hexane, acetone, terpineol, texanol, methyl cellosolve, butyl carbitol, butyl carbitol acetate, and propylene glycol monomethyl ether acetate. It is also possible to use a mixture of two or more of these solvents.
- a translucent heat radiation layer can be formed by dispensing the obtained resin composition on the color conversion layer 5 and drying or thermosetting the resin composition.
- a laminated body of a color conversion sheet and a light transmissive heat radiation layer is prepared, and this is stuck on the resin layer 6.
- a laminate can be produced by applying a resin composition for producing a translucent heat radiation layer on a color conversion sheet and drying or curing the resin composition.
- the light source unit is configured to include at least the above-described light emitter.
- the light source unit include a backlight unit used for a display or the like.
- the light source unit may take a configuration including an optical film such as a prism sheet, a polarizing reflection film film, and a microlens film for the purpose of increasing luminance.
- the light source unit may further include a color filter for the purpose of increasing color purity.
- a display according to an embodiment of the present invention includes at least the above-described light emitter.
- the above-described light emitter is used as a backlight unit.
- the illuminating device which concerns on embodiment of this invention is provided with the above-mentioned light-emitting body at least.
- this lighting device is configured to emit white light by combining a blue LED light source as a light source and a color conversion layer that converts blue light from the blue LED light source into light having a longer wavelength. Is done.
- Acrylic resin Oricox KC-7000 (manufactured by Kyoeisha Chemical) Silicone resin: OE6630A / B (manufactured by Dow Corning Toray).
- Synthesis example 1 Method for Synthesizing Compound G-1 3,5-Dibromobenzaldehyde (3.0 g), 4-tert-butylphenylboronic acid (5.3 g), tetrakis (triphenylphosphine) palladium (0) (0.4 g), and Potassium carbonate (2.0 g) was placed in the flask and purged with nitrogen. Degassed toluene (30 mL) and degassed water (10 mL) were added thereto, and the mixture was refluxed for 4 hours. The reaction solution was cooled to room temperature, and the organic layer was separated and washed with saturated brine. The organic layer was dried over magnesium sulfate and filtered, and then the solvent was distilled off. The obtained reaction product was purified by silica gel chromatography to obtain 3,5-bis (4-tert-butylphenyl) benzaldehyde (3.5 g) as a white solid.
- this compound showed the light absorption characteristic to the blue excitation light source, and showed a sharp emission peak in the green region.
- Synthesis example 2 Synthesis method of compound R-1 4- (4-t-butylphenyl) -2- (4-methoxyphenyl) pyrrole (300 mg), 2-methoxybenzoyl chloride (201 mg), and toluene (10 ml) were mixed at 120 ° C. under a nitrogen stream. For 6 hours. After cooling to room temperature, the solvent was removed by evaporation. The residue was washed with 20 ml of ethanol and vacuum-dried to obtain 260 mg of 2- (2-methoxybenzoyl) -3- (4-t-butylphenyl) -5- (4-methoxyphenyl) pyrrole.
- This compound showed light absorption characteristics for blue and green excitation light sources and a sharp emission peak in the red region.
- Hollow silica particles 1 XG40 (manufactured by Grandex) Average particle size 0.4 ⁇ m
- Hollow silica particles 3 XG200 (manufactured by Grandex) Average particle size 1.0 ⁇ m.
- the hollow silica particles 4 were prepared by the following method. Average particle size 5.0 ⁇ m 800 g of water was put into a 2 L SUS304 jacketed reactor and adjusted to 10 ° C. This was designated as liquid A. In a 500 mL flask, 267 g of methanol (manufactured by Wako Pure Chemical Industries, Ltd.), 16 g of hexane (manufactured by Wako Pure Chemical Industries, Ltd.), 6 g of a 25% by weight aqueous solution of tetramethylammonium hydroxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and lauryl 18 g of a 30% by weight aqueous solution of trimethylammonium chloride (Daiichi Kogyo Seiyaku Co., Ltd.) was added, and the temperature was adjusted to 7 ° C. by attaching to ice water. This was designated as solution B.
- the liquid B was added at an addition rate of 10 g / second. After completion of the addition, the mixture was further stirred for 20 seconds, and 34 g of tetramethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) was further added, followed by stirring for 10 minutes.
- the white cloudy aqueous solution obtained was filtered using 5C filter paper (manufactured by Kiriyama Seisakusho) and dried at 100 ° C. with a dryer to obtain white powder of composite silica particles enclosing hexane inside the particles.
- the white powder of the obtained composite silica particles was heated to 1100 ° C. over 11 hours in a baking furnace (manufactured by Motoyama Co., Ltd., Super Barn), and then held at 1100 ° C. for 1 hour, Hexane was completely removed, and white powder of hollow silica particles 4 was obtained.
- the hollow silica particles 5 were prepared by the following method. Average particle size 10 ⁇ m It was hollow except that 200 g of water was added to the reaction tank during preparation of liquid A, and liquid A was added to liquid B, and after stirring for 20 seconds, 600 g of water was added and then tetramethoxysilane was added. A white powder of hollow silica particles 5 was obtained in the same manner as the method for preparing silica particles 4. The particle size distribution of the hollow silica particles 4 was measured in the same manner as the hollow silica particles 4.
- Porous silica particles 1 Sunsphere H31 (manufactured by AGC S-Tech) Average particle diameter: 3 ⁇ m
- Porous silica particles 2 Sunsphere H51 (manufactured by AGC S-Tech) Average particle size: 5 ⁇ m
- Porous silica particles 3 Sunsphere H121 (manufactured by AGC S-Tech) Average particle size: 12 ⁇ m
- Hollow acrylic particles: ADVANCEL HB-2051 manufactured by Sekisui Chemical Co., Ltd.
- Alumina particles: AKP3000 manufactured by Sumitomo Chemical
- Titania particles JR301 (manufactured by Teica)
- Aluminum nitride particles E grade (manufactured by Tokuyama).
- ⁇ Transmittance measurement> a part of the transmittance measurement sample was cut by a focused ion beam (FIB) processing method, and the cross section of the resin layer was observed by SEM. From the obtained SEM image, the thickness of the resin layer was randomly measured at five points, and the average value was defined as the thickness of the resin layer.
- FIB focused ion beam
- the transmittance at a wavelength of 450 nm was obtained by measuring the transmittance measurement sample created in each example with a basic configuration using an integrating sphere attached to a spectrophotometer (U-4100 Spectrophotometer (manufactured by Hitachi, Ltd.)).
- ⁇ Porosity measurement> The luminescent material produced in each example was cut by a focused ion beam (FIB) processing method, and the cross section of the resin layer was observed by SEM. Ten cross-sections were observed, and the obtained 10 two-dimensional images were read by SEM observation using image processing software ImageJ. Next, the image was converted to gray scale, and binarization processing was used to paint the voids in black and the portions other than the voids in white, and the black portion area and the white portion area were calculated. At this time, the binarization processing was performed by automatic processing. By calculating (area of the black part) / (area of the black part + area of the white part), the porosity was obtained.
- FIB focused ion beam
- ⁇ Measurement of content of heat insulating material> The luminescent material produced in each example and comparative example was cut by a focused ion beam (FIB) processing method, and the cross section of the resin layer was observed by SEM. Ten cross-sections were observed, and the total cross-sectional area corresponding to the heat insulating material of the 10 two-dimensional images obtained was calculated. The total cross-sectional area corresponding to the heat insulating material was divided by the total cross-sectional area of 10 two-dimensional images to obtain the content of the heat insulating material in the resin layer. At this time, the void portion included in the heat insulating material was also part of the heat insulating material.
- FIB focused ion beam
- ⁇ Measurement of film thickness of color conversion layer> The luminescent material produced in each example and comparative example was cut by a focused ion beam (FIB) processing method, and the cross section of the color conversion layer was observed by SEM. The length from the interface between the resin layer and the color conversion layer to the interface between the color conversion layer and the air layer or the heat dissipation layer was measured at 10 locations, and the average value of 10 points was taken as the film thickness of the color conversion layer.
- FIB focused ion beam
- ⁇ Measurement of heat dissipation layer thickness> The luminescent material produced in each example and comparative example was cut by a focused ion beam (FIB) processing method, and the cross section of the heat dissipation layer was observed by SEM. The length from the interface between the color conversion layer and the heat dissipation layer to the interface between the heat dissipation layer and the air layer was measured at 10 locations, and the average value of 10 points was taken as the film thickness of the heat dissipation layer.
- FIB focused ion beam
- Total luminous flux retention (%) (total luminous flux after 1000 hours / total luminous flux immediately after the start of the test) ⁇ 100) ⁇ Calculation of color reproduction range> Calculates the color gamut in the (u ′, v ′) color space when the color purity is improved by the color filter from the emission spectrum data obtained when measuring the chromaticity and the total luminous flux and the spectral data of the transmittance of the color filter. did. Also, the area of the color gamut in the calculated (u ′, v ′) color space is expressed as BT. Evaluation was based on the ratio (color reproduction range (%)) when the color gamut area of the 2020 standard was 100%. The higher this ratio, the better the color reproducibility.
- ⁇ Measurement of average particle size of heat insulating material> The phosphor obtained in each example was polished by a focused ion beam (FIB) processing method so that a cross section of the resin layer was observed. Observe the obtained cross-section with SEM, and from the obtained two-dimensional image, select an arbitrary straight line that intersects the outer edge of the particle at two points with the maximum distance between the two intersections. Was defined as “individual particle size of particles”. A particle size distribution was determined from the individual particle diameters of all the observed particles, and in the distribution, a particle diameter of 50% of the accumulated amount from the small particle diameter side was calculated to obtain an average particle diameter (D50).
- D50 average particle diameter
- Examples 1 to 6 A reflector was formed by sandwiching a glass epoxy substrate on which electrodes had been formed in advance with a mold for transfer molding, pouring thermosetting resin “TA112” (manufactured by Kuraray Co., Ltd.) into the mold and curing it. At this time, the mold was designed so that the shape of the concave portion of the reflector was a square frustum having a length and width of the concave portion of 3 mm, a length and width of the bottom portion of 2 mm, and a depth of 1 mm. Next, a flip chip type blue LED having a thickness of 300 ⁇ m was disposed in the recess formed by the reflector, and the LED electrode and the substrate were electrically connected.
- TA112 manufactured by Kuraray Co., Ltd.
- Silicone resin is put into a 300 ml polyethylene container, and the agitation and defoaming device “Mazerustar KK-400” (manufactured by Kurabo Industries) is used for stirring and defoaming at 1000 rpm for 20 minutes.
- a resin solution was prepared.
- the obtained resin liquid for forming a resin layer was poured into a recess formed by a reflector, and heated at 150 ° C. for 3 hours to form a resin layer. At this time, the thickness of the resin layer was changed by changing the injection amount of the resin liquid for forming the resin layer in each of Examples 1 to 6.
- the resin solution for forming the resin layer was applied onto quartz glass with a blade coater, and then heated in an oven at 150 ° C. for 3 hours to be the same as the film thickness of the resin layer in the light emitters of Examples 1 to 6.
- a resin layer having a film thickness was formed to prepare a transmittance measurement sample. The transmittance of this sample was measured by the method described above.
- Comparative Example 1 In Comparative Example 1, a light emitter was manufactured by performing the same operation as in Example 1 except that no resin layer was provided between the LED and the color conversion layer.
- Examples 7 to 12 were the same as Example 3 except that the silicone resin and the hollow silica particles 1 as the heat insulating material were mixed at the weight ratio shown in Table 3 when the resin liquid for forming the resin layer was prepared. Through this operation, a light emitter and a sample for measuring transmittance were prepared.
- Example 3 a transmittance measurement sample was prepared in the same manner as in Example 3 except that the resin layer forming resin solutions prepared in Examples 7 to 12 were used, and the transmittance was measured. The results are shown in Table 3. The results of Example 3 are shown again.
- Example 13 to 16 In Examples 13 to 16, the same operation as in Example 9 was performed except that the kind of the heat insulating material was changed as shown in Table 4, and a light emitter was produced.
- the thickness of the resin layer of the luminescent material produced in Examples 13 to 16 the content of the heat insulating material in the resin layer, the porosity of the resin layer, the D50 of the heat insulating material, the surface temperature of the color conversion layer, the total luminous flux, The luminous flux maintenance factor and the color reproduction range were measured by the methods described above. Note that the D50 of the heat insulating material in the resin layer was also measured for the luminescent material produced in Example 9.
- Example 9 a transmittance measurement sample was prepared in the same manner as in Example 9 except that the resin layer forming resin solutions prepared in Examples 13 to 16 were used, and the transmittance was measured. The results are shown in Table 4. The results of Example 9 are shown again.
- Example 17 to 22 In Examples 17 to 22, the same procedure as in Example 3 was conducted except that the silicone resin and the porous silica particles 1 as the heat insulating material were mixed at the weight ratio shown in Table 5 when the resin liquid for forming the resin layer was prepared. Through this operation, a light emitter and a sample for measuring transmittance were prepared. Film thickness of resin layer of phosphor produced in Examples 17 to 22, content of heat insulating material in resin layer, porosity of resin layer, surface temperature of color conversion layer, total luminous flux, luminous flux maintenance factor, and color reproduction The range was measured by the method described above.
- Example 3 a transmittance measuring sample was prepared in the same manner as in Example 3 except that the resin liquid for forming a resin layer prepared in Examples 17 to 22 was used, and the transmittance was measured. The results are shown in Table 5. The results of Example 3 are shown again.
- Example 23 and 24 In Examples 23 and 24, the same operation as in Example 19 was performed except that the type of the heat insulating material was changed as shown in Table 6, and a light emitter was produced.
- the film thickness of the resin layer of the phosphor produced in Examples 23 and 24, the content of the heat insulating material in the resin layer, the porosity of the D50 resin layer of the heat insulating material, the surface temperature of the color conversion layer, the total luminous flux, the light flux The maintenance rate and the color reproduction range were measured by the methods described above. Note that the D50 of the heat insulating material in the resin layer was also measured for the luminescent material produced in Example 19.
- Example 19 a transmittance measurement sample was prepared in the same manner as in Example 19 except that the resin liquid for forming a resin layer prepared in Examples 23 and 24 was used, and the transmittance was measured. The results are shown in Table 6. The results of Example 19 are shown again.
- Example 25 A light emitter was produced in the same manner as in Example 9 except that hollow acrylic particles were used as the heat insulating material.
- the thickness of the resin layer of the produced phosphor, the content of the heat insulating material in the resin layer, the porosity of the resin layer, the surface temperature of the color conversion layer, the total luminous flux, the luminous flux maintenance factor, and the color reproduction range are as described above. It was measured by.
- Example 9 a transmittance measurement sample was prepared in the same manner as in Example 9 except that the resin liquid for forming a resin layer prepared in Example 25 was used, and the transmittance was measured. The results are shown in Table 7. The results of Example 3 and Example 9 are shown again.
- Example 25 When hollow acrylic particles were used, the surface temperature of the color conversion layer was the same as when hollow silica particles 1 were used, but the result was that the luminous flux maintenance factor was low. This is probably because the hollow acrylic particles themselves were photodegraded. However, the restraint maintenance rate in Example 25 is improved as compared with Example 3 in which no heat insulating material is used.
- Example 26 A light emitter was fabricated in the same manner as in Example 9 except that the substrate was changed to an aluminum substrate.
- the thickness of the resin layer of the produced phosphor, the content of the heat insulating material in the resin layer, the porosity of the resin layer, the surface temperature of the color conversion layer, the total luminous flux, the luminous flux maintenance factor, and the color reproduction range are as described above. It was measured by. The results are shown in Table 8. The results of Example 9 are shown again.
- Example 27 In Example 27, first, a light emitter was fabricated by the same operation as in Example 9. Next, 100 parts by weight of silicone resin and 5 parts by weight of alumina particles were mixed in a polyethylene container having a volume of 300 ml. This mixture was stirred and degassed for 20 minutes at 1000 rpm using a planetary stirring and defoaming device “Mazerustar KK-400” (manufactured by Kurabo Industries) to prepare a resin solution for forming a heat radiation layer. Using the dispenser, the obtained heat-dissipating layer-forming resin liquid was poured onto the color conversion layer of the luminescent material and heated at 150 ° C. for 3 hours to form a heat-dissipating layer.
- Example 28 a light emitter was produced in the same manner as in Example 27 except that titania particles were used instead of alumina particles.
- Example 29 a light emitter was fabricated in the same manner as in Example 27 except that aluminum nitride particles were used instead of alumina particles.
- the thickness of the resin layer of the phosphor produced in Examples 27 to 29, the content of the heat insulating material in the resin layer, the porosity of the resin layer, the surface temperature of the color conversion layer, the total luminous flux, the luminous flux maintenance factor, and the color was measured by the method described above. The results are shown in Table 9. The results of Example 9 are shown again.
- Example 30 The shape of the recesses formed by the reflectors is 4 mm with a recess length of 1 mm, a recess width of 0.3 mm, a bottom length of 0.8 mm, a bottom width of 0.25 mm, and a depth of 0.5 mm.
- the same operation as in Example 9 was performed except that the mold was designed to be a truncated pyramid.
- the film thickness of the resin layer of the obtained phosphor, the content of the heat insulating material in the resin layer, the porosity of the resin layer, the surface temperature of the color conversion layer, the total luminous flux, the luminous flux maintenance factor, and the color reproduction range are as described above. Measured by the method. The results are shown in Table 10. The results of Example 9 are shown again.
- Example 31 In Example 31, first, 100 parts by weight of acrylic resin, 0.22 parts by weight of compound G-1 and 0.02 parts by weight of compound R-1 were mixed in a polyethylene container having a volume of 300 ml. To the mixture, toluene was added to 200 parts by weight with respect to 100 parts by weight of the acrylic resin, and the mixture was stirred for 60 minutes at 1000 rpm using a planetary stirring and defoaming device “Mazerustar KK-400” (manufactured by Kurabo Industries). Defoaming was performed to obtain a composition for color conversion production.
- the composition for preparing a color conversion layer was applied on a “Lumirror” U48 (manufactured by Toray Industries, Inc., thickness 50 ⁇ m), heated at 120 ° C. for 20 minutes, dried and colored. A conversion layer was formed to produce a color conversion sheet.
- a color conversion sheet as the color conversion layer and the shape of the recess formed by the reflector is a square pyramid having a recess length and width of 3 mm, a bottom length and width of 2 mm, and a depth of 0.4 mm.
- a light emitter was produced in the same manner as in Example 3 except that the mold was designed to be.
- Example 32 the phosphor was produced in the same manner as in Example 31 except that the hollow silica particles 1 were mixed at a ratio of 20 parts by weight with respect to 100 parts by weight of the silicone resin when the resin liquid for forming the resin layer was produced.
- the hollow silica particles 1 were mixed at a ratio of 20 parts by weight with respect to 100 parts by weight of the silicone resin when the resin liquid for forming the resin layer was produced.
- the thickness of the resin layer of the produced phosphor, the content of the heat insulating material in the resin layer, the porosity of the resin layer, the surface temperature of the color conversion layer, the total luminous flux, the luminous flux maintenance factor, and the color reproduction range are as described above. It was measured by. The results are shown in Table 11. The results of Example 3 are shown again.
- Comparative Examples 2 to 7 100 parts by weight of a silicone resin, 30 parts by weight of a green inorganic phosphor, and 20 parts by weight of a red inorganic phosphor were mixed in a polyethylene container having a volume of 300 ml. Next, using a planetary stirring and defoaming apparatus “Mazerustar KK-400” (manufactured by Kurabo Industries), stirring and defoaming were performed at 1000 rpm for 60 minutes to obtain a composition for preparing a color conversion layer.
- a planetary stirring and defoaming apparatus “Mazerustar KK-400” manufactured by Kurabo Industries
- a light emitter was prepared in the same manner as in Comparative Example 1 except that the obtained color conversion layer preparation composition was used for preparation of the color conversion layer.
- Comparative Example 3 a light-emitting body was produced by performing the same operation as in Example 3 except that a color conversion layer was produced using the composition for producing a color conversion layer produced in Comparative Example 2. Further, a transmittance measurement sample was prepared by the same operation as in Example 3, and the transmittance was measured.
- Comparative Example 4 the same operation as in Example 9 was performed except that the color conversion layer was prepared using the composition for preparing the color conversion layer prepared in Comparative Example 2, and a light emitter was prepared. Further, a transmittance measurement sample was prepared by the same operation as in Example 9, and the transmittance was measured.
- Comparative Example 5 the same operation as in Comparative Example 4 was performed, except that an aluminum substrate was used as the substrate, to produce a light emitter. Further, a transmittance measurement sample was prepared by the same operation as in Example 9, and the transmittance was measured.
- Comparative Example 6 the same operation as in Example 27 was performed except that the color conversion layer was prepared using the composition for preparing the color conversion layer prepared in Comparative Example 2, and a light emitter was prepared. Further, a transmittance measurement sample was prepared by the same operation as in Example 27, and the transmittance was measured.
- Comparative Example 7 the same operation as in Comparative Example 3 was performed except that the mold was designed so that the shape of the recess formed by the reflector was a rectangular parallelepiped having a bottom of 1 mm ⁇ 0.3 mm and a depth of 0.5 mm. An attempt was made to make a light emitter. However, the phosphor particles are aggregated, and the color conversion composition cannot be injected into the recess formed by the reflector.
- Table 12 shows the evaluation results of the phosphors produced in Comparative Examples 2 to 6. The results of Comparative Example 1 are shown again.
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Abstract
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US20210139721A1 (en) * | 2018-05-28 | 2021-05-13 | Dic Corporation | Method for producing pigment-kneaded product and aqueous pigment dispersion |
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- 2017-06-14 CN CN201780036980.2A patent/CN109314163A/zh not_active Withdrawn
- 2017-06-14 WO PCT/JP2017/021903 patent/WO2017221777A1/fr active Application Filing
- 2017-06-14 JP JP2017534844A patent/JPWO2017221777A1/ja active Pending
- 2017-06-14 KR KR1020187033210A patent/KR20190019918A/ko unknown
- 2017-06-16 TW TW106120072A patent/TW201809218A/zh unknown
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JP2007035951A (ja) * | 2005-07-27 | 2007-02-08 | Kyocera Corp | 発光装置 |
JP2007327320A (ja) * | 2006-05-09 | 2007-12-20 | Sekisui Chem Co Ltd | 難燃性採光断熱材 |
JP2010061824A (ja) * | 2008-09-01 | 2010-03-18 | Toray Ind Inc | 色変換組成物 |
JP2010135747A (ja) * | 2008-11-07 | 2010-06-17 | Toshiba Lighting & Technology Corp | 発光モジュールおよび照明装置 |
JP2011241160A (ja) * | 2010-05-17 | 2011-12-01 | Yamamoto Chem Inc | 色変換材料、該材料を含む組成物、該組成物を使用した色変換光学部品および該色変換光学部品を使用した発光素子 |
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JP2013014108A (ja) * | 2011-07-06 | 2013-01-24 | Shin-Etsu Chemical Co Ltd | 断熱積層体 |
JP2014136771A (ja) * | 2013-01-17 | 2014-07-28 | Yamamoto Chem Inc | 波長変換層、及びこれを用いた波長変換フィルタ |
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JP2022502832A (ja) * | 2018-09-27 | 2022-01-11 | ナージン テクノロジー コーポレーション リミテッドNajing Technology Corporation Limited | 発光素子の製造プロセス及び発光素子 |
JP7218950B2 (ja) | 2018-09-27 | 2023-02-07 | ナージン テクノロジー コーポレーション リミテッド | 発光素子の製造プロセス及び発光素子 |
Also Published As
Publication number | Publication date |
---|---|
CN109314163A (zh) | 2019-02-05 |
JPWO2017221777A1 (ja) | 2019-04-11 |
KR20190019918A (ko) | 2019-02-27 |
TW201809218A (zh) | 2018-03-16 |
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