Color conversion composition, color conversion member, and light source unit, display and lighting device each including same

Abstract

A color conversion composition according to one aspect of the present invention contains at least one type of light-emitting material and a binder resin. The at least one type of light-emitting material includes a compound that has a structure represented by general formula (1). (The ring Za, the ring Zb, the ring Zc, the ring Zd, the ring Ze, the ring Zf, and the ring Zg each independently represent a substituted or unsubstituted aryl ring having 5 to 30 ring atoms or a substituted or unsubstituted heteroaryl ring having 5 to 30 ring atoms. Z1 to Z4 each independently represent a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa, C=O, S(=O), or S(=O)2. E represents a boron atom, a phosphorus atom, SiRa, or P=O. Each of the substituents Ra and RC is selected from a specific substituent group.)

Description

Color-converting composition, color-converting member, and light source unit, display, and lighting device including the same

[0001] The present invention relates to a color-converting composition, a color-converting member, and a light source unit, a display, and a lighting device each including the same.

[0002] There has been active research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, lighting devices, etc. Color conversion refers to converting light emitted from a light emitter into light with a longer wavelength, such as converting blue light into green or red light.

[0003] By forming this composition having color conversion function (hereinafter referred to as color conversion composition) into a sheet and combining it with, for example, a blue light source, it becomes possible to obtain the three primary colors of blue, green, and red from the blue light source, i.e., to obtain white light. A white light source combining such a blue light source with a sheet having color conversion function (hereinafter referred to as color conversion sheet) is used as a light source unit such as a backlight unit, and by combining this light source unit with a liquid crystal driving part and a color filter, it becomes possible to produce a full-color display. Furthermore, a white light source combining a blue light source with a color conversion sheet can also be used directly as a white light source (lighting device) such as LED lighting.

[0004] One of the challenges facing displays that utilize a color conversion method is improving color reproducibility. To improve color reproducibility, it is effective to narrow the half-width of the blue, green, and red emission spectra of the light source unit and increase the color purity of each of the blue, green, and red colors. To solve this problem, for example, color conversion materials containing organic fluorescent materials have been proposed (see, for example, Patent Documents 1 and 2).

[0005] JP 2010-61824 A JP 2014-136771 A

[0006] Conventionally, color-converting compositions with excellent color reproducibility have been obtained by the techniques described in Patent Documents 1 and 2. However, in order to realize displays with more vivid colors, higher color reproducibility than before is required, and there is a demand for wide color gamut standards such as the DCI-P3 standard to be satisfied. Furthermore, in recent years, with the trend toward higher definition such as 4K and 8K, high dynamic range (HDR), and high contrast achieved by local dimming, the brightness required for light source units of displays has increased. Therefore, higher color reproducibility and higher brightness are also being demanded for color-converting members such as color-converting sheets.

[0007] The problem to be solved by the present invention is to improve the color reproducibility of color conversion compositions and color conversion members used in light source units, displays, or lighting devices, and in particular to satisfy wide color gamut standards. Another object of the present invention is to provide color conversion compositions and color conversion members that can achieve both high color reproducibility and high brightness.

[0008] In order to solve the above-mentioned problems and achieve the object, the present invention has any one of the following configurations.

[0009] That is, the color-changing composition according to the present invention is a color-changing composition comprising [1] at least one kind of luminescent material and a binder resin, characterized in that the at least one kind of luminescent material comprises a compound having a structure represented by the following general formula (1):

[0010] (In general formula (1), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf, and ring Zg are each independently a substituted or unsubstituted aryl ring having 5 to 30 ring members, or a substituted or unsubstituted heteroaryl ring having 5 to 30 ring members. Z 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1 When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4When R is NRa, the substituent R may be bonded to the ring Zd or the ring Z to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O. The substituents R and R C are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C Each of may be further substituted with selected substituents, and those substituents may be further substituted with selected substituents.

[0011] The color-changing composition according to the present invention is characterized in that, in the invention described in [1] above, the structure represented by general formula (1) is a structure represented by the following general formula (2):

[0012] In the general formula (2), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf and ring Zg are benzene rings. 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1 When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4 When R is NRa, the substituent R may be bonded to the ring Zd or the ring Z to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O. C , R a1 ~Ra3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 Each of may be further substituted with selected substituents, and those substituents may be further substituted with selected substituents.

[0013] The color-converting composition according to the present invention is [3] the invention described in [1] or [2] above, characterized in that in general formula (1), at least one of ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf and ring Zg has one or more groups selected from 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, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carboxy group, an ester group, an acyl group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, an alkylamine and a cyclic amine.

[0014] Furthermore, the color-changing composition according to the present invention is characterized in that, in the invention described in any one of the above items [1] to [3], in the general formula (1), at least one of ring Za and ring Zd has an aryl group.

[0015] Furthermore, the color-changing composition according to the present invention is characterized in that, in the invention described in any one of the above items [1] to [4], in the general formula (1), at least one of ring Za and ring Zd has a phenyl group.

[0016] Furthermore, the color-changing composition according to the present invention is [6] the invention described in the above [1], wherein in the general formula (1), Z 1 ~Z 4 is an oxygen atom, a nitrogen atom, or NRa.

[0017] The color-changing composition according to the present invention is characterized in that, in the invention described in any one of the above items [1] to [5], E in the general formula (1) is a boron atom.

[0018] Furthermore, the color-changing composition according to the present invention, in the invention described in any one of [8] to [7] above, is characterized in that in the general formula (2), R a2 and R d2 is a phenyl group.

[0019] Furthermore, the color-converting composition according to the present invention is characterized in that, in the invention described in any one of the above items [1] to [8], the compound having a structure represented by the general formula (1) exhibits light emission with a peak wavelength observed in the region of 500 nm or more and less than 580 nm when excited by light.

[0020]

[10] A color-changing member according to the present invention is characterized by comprising the color-changing composition according to any one of [1] to [9] above, or a cured product thereof.

[0021]

[11] The color conversion member according to the present invention is characterized in that, in the invention described in

[10] above, it has an oxygen barrier layer.

[0022] The light source unit according to the present invention is characterized by comprising:

[12] a light source; and the color conversion member according to

[10] or

[11] above.

[0023] Furthermore, the light source unit according to the present invention is characterized in that, in the invention described in

[12] above, the light source is a light-emitting diode having a maximum light emission in the wavelength range of 430 nm or more and 500 nm or less.

[0024]

[14] A display according to the present invention is characterized by comprising the light source unit according to

[12] or

[13] above.

[0025]

[15] A lighting device according to the present invention is characterized by comprising the light source unit according to

[12] or

[13] above.

[0026] The color-converting composition of the present invention and the color-converting member using the same have both high color purity and high brightness, and therefore have the effect of making it possible to achieve both high color reproducibility and high brightness.

[0027] Fig. 1 is a schematic cross-sectional view showing a first example of a color conversion member according to an embodiment of the present invention. Fig. 2 is a schematic cross-sectional view showing a second example of a color conversion member according to an embodiment of the present invention. Fig. 3 is a schematic cross-sectional view showing a third example of a color conversion member according to an embodiment of the present invention. Fig. 4 is a schematic cross-sectional view showing a fourth example of a color conversion member according to an embodiment of the present invention. Fig. 5 is a schematic cross-sectional view showing a fifth example of a color conversion member according to an embodiment of the present invention. Fig. 6 is a schematic cross-sectional view showing a sixth example of a color conversion member according to an embodiment of the present invention.

[0028] Hereinafter, preferred embodiments of the color-converting composition, color-converting member, and light source unit, display, and lighting device containing the same according to the present invention will be specifically described, but the present invention is not limited to the following embodiments and can be modified in various ways depending on the purpose and application. Furthermore, matters cited as preferred examples in specific embodiments and implementations can also be applied to other embodiments and implementations.

[0029] <Color-Converting Composition> The color-converting composition according to an embodiment of the present invention (hereinafter sometimes abbreviated as the color-converting composition of the present invention) contains at least one luminescent material and a binder resin. The luminescent material and binder resin contained in the color-converting composition of the present invention will be explained below in order.

[0030] <Light-emitting material> The color-converting composition according to the embodiment of the present invention contains at least one light-emitting material. Here, the light-emitting material in the present invention refers to a material that, when irradiated with a certain light, emits light of a wavelength different from the light.

[0031] Examples of luminescent materials include inorganic fluorescent materials, fluorescent pigments, fluorescent dyes, and quantum dots. The color-converting composition of the present invention may contain two or more of these luminescent materials. In order to achieve highly efficient color conversion, the luminescent material is preferably a material that exhibits luminescent properties with a high quantum yield, and among these, quantum dots and organic luminescent materials are preferably used. Furthermore, from the viewpoints of uniform dispersion, reduced usage, and reduced environmental impact, it is more preferable to use an organic luminescent material as the luminescent material.

[0032] Examples of suitable organic light-emitting materials include compounds having a fused aryl ring, such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, and indene, and derivatives thereof. Examples of suitable organic light-emitting materials include compounds having a heteroaryl ring, such as furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine, and derivatives thereof, and borane derivatives.

[0033] Other suitable organic light-emitting materials include stilbene derivatives such as 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)ethenyl)biphenyl, and 4,4'-bis(N-(stilben-4-yl)-N-phenylamino)stilbene; aromatic acetylene derivatives; tetraphenylbutadiene derivatives; aldazine derivatives; pyrromethene derivatives; and diketopyrrolo[3,4-c]pyrrole derivatives. Other suitable organic light-emitting materials include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; azole derivatives and metal complexes thereof such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole; cyanine compounds such as indocyanine green; and xanthene and thioxanthene compounds such as fluorescein, eosin, and rhodamine.

[0034] Suitable organic light-emitting materials include polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives and their metal complexes, porphyrin derivatives and their metal complexes, oxazine compounds such as Nile Red and Nile Blue, helicene compounds, and aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine. Suitable organic light-emitting materials also include organometallic complex compounds of iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), europium (Eu), and rhenium (Re). However, the organic light-emitting material of the present invention is not limited to the above.

[0035] The organic light-emitting material may be a fluorescent material or a phosphorescent material, but a fluorescent material is preferred to achieve high color purity. As mentioned above, in order to improve color reproducibility, it is preferable that the half-width of the emission spectrum of each of the blue, green, and red colors is small. Therefore, the half-width of the emission spectrum at the emission peak wavelength of at least one light-emitting material contained in the color-converting composition of the present invention is preferably 60 nm or less, more preferably 50 nm or less.

[0036] The at least one luminescent material contained in the color-converting composition of the present invention includes a compound having a structure represented by the following general formula (1): In other words, the color-converting composition of the present invention contains at least this compound as an organic luminescent material suitable for improving color reproducibility, etc.

[0037]

[0038] In general formula (1), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf, and ring Zg are each independently a substituted or unsubstituted aryl ring having 5 to 30 ring members, or a substituted or unsubstituted heteroaryl ring having 5 to 30 ring members. 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4 When R is NRa, the substituent R may be bonded to the ring Zd or the ring Ze to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O.

[0039] In addition, in the general formula (1), the substituents Ra and R C are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C may be further substituted with a substituent selected from among these. The substituent substituting the substituent Ra may be further substituted with a substituent selected from among these.

[0040] In all of the above groups, hydrogen may be deuterium. This also applies to the compounds or partial structures thereof described below. In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms refers to an aryl group having 6 to 40 carbon atoms, including the number of carbon atoms contained in the substituents substituted on the aryl group. The same applies to other substituents that specify the number of carbon atoms.

[0041] The term "unsubstituted" in the context of "substituted or unsubstituted" means that a hydrogen atom or a deuterium atom has been substituted. The same applies to the term "substituted or unsubstituted" in the compounds or partial structures thereof described below.

[0042] In addition, in all of the above groups, examples of the substituent when substituted include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an imino group, an amino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, or a phosphine oxide group. In addition, these substituents may be further substituted with the above-mentioned substituents.

[0043] The alkyl group refers to 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 may or may not have a substituent. When the alkyl group is substituted, the additional substituent is not particularly limited, and examples thereof include an alkyl group, a halogen atom, an aryl group, and a heteroaryl group, and this point is also applicable to the following description. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably in the range of 1 to 20, more preferably 1 to 8, from the viewpoints of availability and cost.

[0044] The cycloalkyl group refers to a saturated alicyclic hydrocarbon group, such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, or the like, which may or may not have a substituent. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0045] The heterocyclic group refers to an aliphatic ring having atoms other than carbon atoms in the ring, such as a pyran ring, a piperidine ring, or a cyclic amide, which may or may not have a substituent. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 to 20.

[0046] The 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. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0047] The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may or may not have a substituent. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 to 20.

[0048] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, which may or may not have a substituent. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 to 20.

[0049] The alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond, such as a methoxy group, an ethoxy group, or a propoxy group, and this aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.

[0050] An alkylthio group is an alkoxy group in which the oxygen atom of the ether bond is replaced with a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.

[0051] The aryl ether group refers to a functional group in 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. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 to 40.

[0052] An aryl thioether group is an aryl ether group in which the oxygen atom of the ether bond is substituted with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 to 40.

[0053] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a benzophenanthryl group, a benzanthracenyl group, a chrysenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a benzofluoranthenyl group, a dibenzoanthracenyl group, a perylenyl group, or a helicenyl group. Among these, 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, or a triphenylenyl group is preferred. The aryl group may or may not have a substituent. The number of carbon atoms in the aryl group is not particularly limited, but is preferably in the range of 6 to 40, more preferably 6 to 30.

[0054] 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, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, even more preferably a phenyl group, a biphenyl group, or a terphenyl group, and particularly preferably a phenyl group.

[0055] When each of the substituents is further substituted with an aryl group, 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, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and particularly preferably a phenyl group.

[0056] Examples of heteroaryl groups include pyridyl, furanyl, thienyl, quinolinyl, isoquinolinyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and benzocarbazolyl. It refers to a cyclic aromatic group having one or more atoms other than carbon in the ring, such as a benzoyl group, a carbolinyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a dihydroindenocarbazolyl group, a benzoquinolinyl group, an acridinyl group, a dibenzoacridinyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group. However, a naphthyridinyl group refers to a 1,5-naphthyridinyl group, a 1,6-naphthyridinyl group, a 1,7-naphthyridinyl group, a 1,8-naphthyridinyl group, a 2,6-naphthyridinyl group, or a 2,7-naphthyridinyl group. The heteroaryl group may or may not have a substituent. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 or more and 40 or less, and more preferably 2 or more and 30 or less.

[0057] As the heteroaryl group, a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group is preferred, and a pyridyl group, a furanyl group, a thienyl group, or a quinolinyl group is more preferred, and a pyridyl group is particularly preferred.

[0058] When each substituent is further substituted with a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furanyl group, a thienyl group, a quinolinyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a phenanthrolinyl group, more preferably a pyridyl group, a furanyl group, a thienyl group, or a quinolinyl group, and particularly preferably a pyridyl group.

[0059] The term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine. The carbonyl group, carboxy group, oxycarbonyl group, ester group, carbamoyl group, amide group, and imino group may or may not have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.

[0060] The sulfonyl group, sulfonate group, and sulfonamide group are each represented by —S(═O)R 10 , -S(=O)2OR 10 , -S(=O)NR 10 R 11 These R 10 and R 11 are each selected from the same group as the hydrogen atom or the substituents when substituted as described above.

[0061] The amino group is a substituted or unsubstituted amino group. In the case of substitution, examples of the substituent include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. As the aryl group and the heteroaryl group, a phenyl group, a naphthyl group, a pyridyl group, and a quinolinyl group are preferred. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably 6 to 40, and particularly preferably 6 to 30.

[0062] The silyl group refers to, for example, alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, propyldimethylsilyl group, and vinyldimethylsilyl group, and arylsilyl groups such as phenyldimethylsilyl group, tert-butyldiphenylsilyl group, triphenylsilyl group, and trinaphthylsilyl group. The substituent on silicon may be further substituted. The number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.

[0063] The siloxanyl group refers to a silicon compound group via an ether bond, such as a trimethylsiloxanyl group. The substituent on the silicon may be further substituted. The boryl group refers to a substituted or unsubstituted boryl group. In the case of substitution, examples of the substituent 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. Among these, an aryl group and an aryl ether group are preferred.

[0064] The phosphine oxide group is —P(═O)R 10 R 11 The R of the phosphine oxide group is a group represented by the formula: 10 and R 11 are each selected from the same group as the hydrogen atom or the substituents when substituted as described above.

[0065] In addition, in the compound having the structure represented by general formula (1), any two adjacent substituents may be bonded to each other to form a conjugated or non-conjugated fused ring or aliphatic ring. The constituent elements of such a fused ring or aliphatic ring may include, in addition to carbon, an element selected from nitrogen, oxygen, sulfur, phosphorus, and silicon. Furthermore, the fused ring or aliphatic ring may be further fused with another ring.

[0066] The compound having the structure represented by general formula (1) exhibits a high fluorescence quantum yield and has a narrow half-width of the emission spectrum at the peak emission wavelength, and therefore can achieve both efficient color conversion and high color purity.

[0067] Furthermore, by introducing appropriate substituents into appropriate positions of the compound having the structure represented by general formula (1), various characteristics and physical properties such as luminous efficiency, color purity, thermal stability, light stability, and dispersibility can be adjusted.

[0068] Furthermore, in a compound having a structure represented by general formula (1), the emission spectrum becomes sharp due to the multiple resonance effect. Therefore, when at least one of the light-emitting materials contained in the color-converting composition of the present invention is a compound having a structure represented by general formula (1), light emission with high color purity can be obtained. In other words, a compound having a structure represented by general formula (1) is advantageous for improving the color gamut of a display, and is therefore preferable as the light-emitting material.

[0069] Furthermore, in a compound having a structure represented by general formula (1), rings Za, Zb, Zc, Zd, Ze, Zf, and Zg are present around E in general formula (1), where the LUMO (Lowest Unoccupied Molecular Orbital) orbital is mainly localized, and therefore the LUMO orbital can be delocalized from E (for example, a boron atom) to each ring. By delocalizing the LUMO orbital, the multiple resonance effect works efficiently, thereby obtaining light emission with higher color purity.

[0070] In one embodiment, the compound having the structure represented by general formula (1) is preferably a light-emitting material that emits delayed fluorescence. Light-emitting materials that emit delayed fluorescence are discussed on pages 87-103 of "State-of-the-Art Organic EL" (edited by Adachi Chinaya and Fujimoto Hiroshi, published by CMC Publishing). This document explains that by bringing the energy levels of the singlet and triplet excited states of the light-emitting material closer together, reverse energy transfer from the triplet excited state, which normally has a low transition probability, to the singlet excited state occurs with high efficiency, resulting in the development of thermally activated delayed fluorescence (TADF). Furthermore, Figure 5 in this document explains the mechanism behind delayed fluorescence generation. Delayed fluorescence emission can be confirmed by transient photoluminescence (PL) measurements.

[0071] In this specification, a light-emitting material that emits fluorescence by transitioning from a triplet excited state to a singlet excited state with high efficiency, including a light-emitting material that exhibits thermally activated delayed fluorescence, is referred to as a "light-emitting material that emits delayed fluorescence." In addition, hereinafter, the "light-emitting material that emits delayed fluorescence" may be abbreviated as a "delayed fluorescent material."

[0072] Typically, fluorescent light is emitted from a singlet excited state generated after photoexcitation of a light-emitting material, and a light-emitting material in a triplet excited state generated by intersystem crossing is thermally deactivated in a room temperature environment. Therefore, fluorescent light is not emitted from the light-emitting material in the triplet excited state. On the other hand, as described above, a light-emitting material that emits delayed fluorescence quickly converts a triplet excited state into a singlet excited state even if the triplet excited state is generated, and then emits fluorescent light. Therefore, the triplet excited state, which cannot contribute to light emission in ordinary fluorescent light-emitting materials, can also contribute to fluorescent light emission. Therefore, highly efficient light emission can be obtained.

[0073] In general formula (1), examples of the substituted or unsubstituted 5-30-membered aryl rings in ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf, and ring Zg include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, a phenanthrene ring, a chrysene ring, an anthracene ring, a pyrene ring, a triphenylene ring, a fluorenine ring, a benzofluorene ring, a dibenzofluorene ring, a benzophenanthrene ring, a benzanthracene ring, a fluoranthene ring, a benzofluoranthene ring, a dibenzanthracene ring, and a perylene ring. Among these, a benzene ring is preferred from the viewpoint of ensuring solubility. Furthermore, examples of the 5-30-membered heteroaryl ring include aromatic heteroaryl ring structures such as a pyridine ring, a quinoline ring, and a phenanthroline ring. Among these, a pyridine ring is preferred from the viewpoints of ease of raw material availability and difficulty of synthesis.

[0074] Furthermore, since the rigidity of the molecular skeleton of a compound having a structure represented by general formula (1) is increased and emission of high color purity can be exhibited, it is preferable that in general formula (1), at least one of rings Za, Zb, Zc, Zd, Ze, Zf, and Zg has one or more groups selected from 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, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carboxy group, an ester group, an acyl group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, an alkylamine, and a cyclic amine. Among these, an aryl group is preferable because it can increase the rigidity of the molecular skeleton and suppress a decrease in fluorescence quantum yield due to molecular motion. Furthermore, an aryl group is preferable because it extends the conjugation and increases the emission wavelength, thereby achieving an appropriate emission wavelength.

[0075] Examples of the aryl group include a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, and a phenanthrenyl group. Among these, a phenyl group is more preferred. Furthermore, a phenyl group substituted with an alkyl group is particularly preferred. This is because the substitution with an alkyl group, which is a sterically hindering group, reduces the overlapping of molecules, thereby suppressing a decrease in brightness and increasing dispersibility in the binder resin.

[0076] In addition, in the general formula (1), Z 1 ~Z 4 is preferably an oxygen atom, a nitrogen atom, or NRa. This is because, in a compound having a structure represented by general formula (1), an oxygen atom or a nitrogen atom having a strong electron donating property and an E having an electron accepting property are arranged in close positions in the molecule, thereby obtaining high-purity light emission due to the multiple resonance effect. In particular, since the multiple resonance effect is stronger, Z 1 ~Z 4 is more preferably a nitrogen atom or NRa.

[0077] In addition, in the general formula (1), E is preferably a boron atom, because in the compound having the structure represented by the general formula (1), the electron-donating Z 1 ~Z 4 This is because the electron-accepting boron atom and the electron-accepting boron atom are closely positioned within the molecule, resulting in high-purity emission due to the multiple resonance effect.

[0078] Furthermore, in the general formula (1), Z 1 ~Z 4 is preferably an oxygen atom, a nitrogen atom, or NRa, and E is preferably a boron atom. This is because, in a compound having a structure represented by general formula (1), an oxygen atom or a nitrogen atom having a strong electron donor property and a boron atom having a strong electron acceptor property are arranged in close positions within the molecule, thereby obtaining high-purity emission due to the multiple resonance effect. In particular, since the multiple resonance effect is stronger, Z 1 ~Z 4 More preferably, is a nitrogen atom or NRa, and E is a boron atom.

[0079] In one aspect of the embodiment of the present invention, the structure represented by general formula (1) is a structure represented by the following general formula (2): In other words, the color-converting composition of the present invention may contain a compound having a structure represented by general formula (2) as the organic light-emitting material, which is a compound having a structure represented by general formula (1).

[0080]

[0081] In general formula (2), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf and ring Zg are benzene rings. 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1 When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4When R is NRa, the substituent R may be bonded to the ring Zd or the ring Ze to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O.

[0082] In addition, in the general formula (2), the substituents Ra and R C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 Each of these may be further substituted with a substituent selected from the above. C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~Re4 , R f1 ~R f4 and R g1 ~R g4 The substituents substituting each of the above may be further substituted with a substituent selected from among these.

[0083] The rigidity of the molecular skeleton of the compound having the structure represented by general formula (2) is increased, and a decrease in the fluorescence quantum yield due to molecular motion can be suppressed. a2 and R d2 It is more preferable that R has an aryl group. a2 and R d2 It is preferable that the aryl group is a phenyl group.

[0084] Examples of compounds having a structure represented by the above-mentioned general formula (1) or compounds having a structure represented by the general formula (2) are shown below, but these compounds are not limited to the following compounds.

[0085]

[0086] In addition to the compounds having the chemical structures exemplified above, examples of compounds having a structure represented by general formula (1) or a structure represented by general formula (2) include compounds in which some hydrogen atoms in the structure are substituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted phenyl group. Among these compounds, some hydrogen atoms in the structure may be substituted with a tert-butyl group, a diphenylamino group substituted with an alkyl group, a carbazolyl group substituted with an alkyl group, or a phenyl group substituted with an alkyl group.

[0087] The color-converting composition of the present invention preferably contains the following luminescent material (a). The luminescent material (a) is a luminescent material that, when excited with light having a wavelength in the range of 400 nm to 500 nm, emits light whose peak wavelength is observed in the range of 500 nm to less than 580 nm. Hereinafter, the light whose peak wavelength is observed in the range of 500 nm to less than 580 nm will be referred to as "green light emission" as necessary. When the color-converting composition of the present invention contains the luminescent material (a), green light emission with high color purity is obtained. In other words, it is preferable that the color-converting composition of the present invention contains the luminescent material (a), because this improves color reproducibility in the green region when the color-converting composition is used in a display or lighting device.

[0088] The color-converting composition of the present invention preferably contains the above-mentioned luminescent material (a) and the following luminescent material (b). As described above, the luminescent material (a) is a luminescent material that emits light with a peak wavelength of 500 nm or more and less than 580 nm when excited with excitation light having a wavelength of 400 nm or more and 500 nm or less. The luminescent material (b) is a luminescent material that emits light with a peak wavelength observed in the range of 580 nm or more and 750 nm or less when excited with at least one of excitation light having a wavelength of 400 nm or more and 500 nm or less and the emission from the luminescent material (a). Hereinafter, the emission observed in the peak wavelength range of 580 nm or more and 750 nm or less will be referred to as "red emission" as necessary. When the color-converting composition of the present invention contains the luminescent material (a) and the luminescent material (b), red emission with high color purity can be obtained. That is, it is preferable that the color-converting composition of the present invention contains the luminescent material (a) and the luminescent material (b) because this improves color reproducibility in the red range when the color-converting composition is used in a display or lighting device.

[0089] Because a portion of excitation light in the wavelength range of 400 nm to 500 nm is partially transmitted through the color conversion composition of the present invention or a color conversion member (a member containing the color conversion composition or a cured product thereof), when a blue LED with a sharp emission peak is used, a sharply shaped emission spectrum is exhibited in each of the blue, green, and red colors, and white light with excellent color purity can be obtained. As a result, particularly in displays, a wider color gamut with more vivid colors can be efficiently produced. Furthermore, in lighting applications, the emission characteristics, particularly in the green and red regions, are improved compared to white LEDs that combine a blue LED and a yellow phosphor, which are currently mainstream, and therefore a desirable white light source with improved color rendering properties can be obtained.

[0090] Examples of the luminescent material (a) include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; cyanine derivatives such as indocyanine green; fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, and carboxyfluorescein diacetate; phthalocyanine derivatives such as phthalocyanine green; perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate; pyrromethene derivatives, stilbene derivatives, oxazine derivatives, naphthalimide derivatives, pyrazine derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, imidazopyridine derivatives, azole derivatives; compounds having fused aryl rings such as anthracene and their derivatives; aromatic amine derivatives; and organometallic complex compounds. Furthermore, compounds having a structure represented by the above-described general formula (1) also exhibit luminescence with high color purity and are therefore suitable as luminescent materials contained in the color-converting composition of the present invention. The color-converting composition of the present invention may contain two or more of these as at least one luminescent material.

[0091] Examples of the luminescent material (b) include cyanine derivatives such as 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostillyl)-4H-pyran, rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulforhodamine 101, pyridine derivatives such as 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)-pyridinium-perchlorate, perylene derivatives such as N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-bisdicarboimide, porphyrin derivatives, pyrromethene derivatives, oxazine derivatives, pyrazine derivatives, compounds having a condensed aryl ring such as naphthacene and dibenzodiindenoperylene, and derivatives thereof, and organometallic complex compounds. Furthermore, compounds having a structure represented by the above-mentioned general formula (1) also exhibit luminescence with high color purity, and are therefore suitable as the luminescent material contained in the color-converting composition of the present invention. The color-converting composition of the present invention may contain two or more of these as the at least one luminescent material.

[0092] In one embodiment of the color-converting composition of the present invention, the compound having a structure represented by general formula (1) is a light-emitting material, such as the above-mentioned light-emitting material (a), that emits light with an emission peak observed in the region of 500 nm or more and less than 580 nm when excited with light. In this case, green light emission with high color purity is obtained, and color reproducibility in the green region is improved. For this reason, it is preferable that the compound having a structure represented by general formula (1) is a light-emitting material that emits green light (e.g., light-emitting material (a)).

[0093] In another embodiment of the color-converting composition of the present invention, the compound having a structure represented by general formula (1) is a light-emitting material (e.g., light-emitting material (b)) that emits light with a peak wavelength observed in the region of 580 nm or more and less than 750 nm, as described above. In this case, red light emission with high color purity is obtained, and color reproducibility in the red region is improved. For this reason, it is preferable that the compound having a structure represented by general formula (1) is a light-emitting material that emits red light.

[0094] As described above, in order to improve color reproducibility, it is preferable that the half width of the emission spectrum of each of blue, green, and red is small, and in particular, it is effective to improve color reproducibility that the half width of the emission spectrum of green light and red light is small. For example, the half width of the emission spectrum of the above-mentioned luminescent material (a) is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 35 nm or less, and particularly preferably 30 nm or less. The half width of the emission spectrum of the above-mentioned luminescent material (b) is preferably 60 nm or less, more preferably 50 nm or less, even more preferably 45 nm or less, and particularly preferably 40 nm or less.

[0095] The content of the luminescent material in the color-converting composition of the present invention can be selected depending on the molar absorption coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the thickness and transmittance of the color-converting member (color-converting sheet, etc.) to be produced. Here, the content of the luminescent material refers to the total content when the color-converting composition of the present invention contains two or more luminescent materials. The content of the luminescent material is 1.0 × 10 relative to 100 parts by weight of the binder resin contained in the color-converting composition of the present invention. -2 It is preferably from 1 part by weight to 5 parts by weight.

[0096] Furthermore, when the color-changing composition of the present invention contains both a light-emitting material (a) that emits green light and a light-emitting material (b) that emits red light, part of the green light is converted into red light, so the content w of the light-emitting material (a) can be adjusted to 1 / 200 of the red light. a and the content w of the luminescent material (b). b That is, w a ≧w b In addition, the content ratio w of these light-emitting materials (a) and (b) is preferably a :w b is preferably 200:1 to 3:1. a and content w b is the weight percent relative to the weight of the binder resin contained in the color converting composition of the present invention.

[0097] The color-converting composition of the present invention may contain other compounds as needed in addition to the compounds exemplified above as luminescent materials. For example, the color-converting composition of the present invention may contain an assist dopant to improve the efficiency of energy transfer from excitation light to the luminescent material. Furthermore, when it is desired to add luminescent color, the color-converting composition of the present invention may further contain the above-mentioned organic luminescent material or a known luminescent material such as an inorganic phosphor, a fluorescent pigment, a fluorescent dye, or a quantum dot.

[0098] Examples of organic light-emitting materials other than the compounds exemplified above (compounds having a structure represented by general formula (1)) are shown below. However, the organic light-emitting materials are not particularly limited to these.

[0099]

[0100] <Binder Resin> The color-changing composition of the present invention contains a binder resin in addition to at least one luminescent material described above. Materials with excellent moldability, transparency, heat resistance, and the like are preferably used as the binder resin. Examples of binder resins include known materials such as photocurable resist materials having reactive vinyl groups, such as acrylic acid-based, methacrylic acid-based, polyvinyl cinnamate-based, and cyclic rubber-based materials, epoxy resins, silicone resins (including organopolysiloxane cured products (crosslinked products) such as silicone rubber and silicone gel), urea resins, fluororesins, polycarbonate resins, acrylic resins, urethane resins, melamine resins, polyvinyl resins, polyamide resins, phenolic resins, polyvinyl alcohol resins, cellulose resins, aliphatic ester resins, aromatic ester resins, aliphatic polyolefin resins, and aromatic polyolefin resins. Furthermore, mixtures or copolymers of these resins may be used as the binder resin. By appropriately designing these resins, binder resins useful for the color-changing composition of the present invention and color-changing materials using the color-changing composition can be obtained.

[0101] Among these resins, from the viewpoints of transparency and dispersibility of the light-emitting material, any of acrylic resins, copolymer resins containing an acrylic acid ester or methacrylic acid ester moiety, polyester resins, cycloolefin resins, epoxy resins, and silicone resins is preferable. Also, from the viewpoint of heat resistance, hydrogenated styrene-based resins, resins having a fluorene skeleton, and copolymer resins containing these resins can be suitably used.

[0102] Examples of binder resins include thermosetting resins, photocurable resins, and thermoplastic resins. Thermoplastic resins have few reactive functional groups and contain few reactive impurities such as polymerization initiators and crosslinking agents, and therefore are less likely to inhibit the luminescence of the luminescent material, making them suitable for use as binder resins. From the viewpoint of heat resistance, thermosetting resins and photocurable resins are suitable for use as binder resins.

[0103] When the binder resin is a thermoplastic resin, the glass transition temperature (Tg) of the binder resin is not particularly limited, but is preferably 30°C or higher and 180°C or lower. When the Tg of the binder resin is 30°C or higher, molecular motion of the binder resin due to heat from incident light from a light source or heat from operating the device is suppressed, thereby suppressing changes in the dispersion state of the luminescent material in the binder resin, thereby preventing deterioration in the luminescent efficiency and durability of the color-converting composition. Furthermore, when the Tg of the binder resin is 180°C or lower, the flexibility of the binder resin can be ensured when molded into a sheet or the like. The Tg of the binder resin is more preferably 50°C or higher and 170°C or lower, even more preferably 70°C or higher and 160°C or lower, and particularly preferably 90°C or higher and 150°C or lower. The glass transition temperature of the thermoplastic resin can be measured using a commercially available measuring device (for example, a differential scanning calorimeter manufactured by Seiko Instruments Inc. (trade name: DSC6220, temperature rise rate: 0.5° C. / min)).

[0104] The binder resin is preferably a polymer or hydrogenation product of at least one monomer selected from the group consisting of acrylic acid esters, methacrylic acid esters, and styrene, and has a Tg of 100°C or higher. In this case, the Tg is more preferably 110°C or higher, and particularly preferably 120°C or higher. These resins can be obtained by known methods, such as copolymerizing the raw material monomers in the presence of a polymerization initiator, or by polymerizing and then converting the structure through a chemical reaction such as an addition reaction, a substitution reaction, or an oxidation-reduction reaction. Commercially available binder resins can also be used.

[0105] <Additives> The color-converting composition of the present invention may contain, as necessary, other components (e.g., additives) in addition to the at least one light-emitting material and binder resin described above. Examples of additives include fillers, light stabilizers, antioxidants, processing and heat stabilizers, light resistance stabilizers such as UV absorbers, dispersants and leveling agents for stabilizing the coating film, scattering agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, pigments, and adhesion aids such as silane coupling agents as film surface modifiers.

[0106] Examples of fillers include fine particles of fumed silica, glass powder, quartz powder, titanium oxide, zirconia oxide, barium titanate, zinc oxide, and silicone fine particles. The color-changing composition of the present invention may contain two or more of these fillers.

[0107] Examples of light stabilizers include, but are not limited to, tertiary amines, catechol derivatives, complexes containing at least one transition metal selected from the group consisting of nickel (Ni), scandium (Sc), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co), copper (Cu), yttrium (Y), zirconium (Zr), molybdenum (Mo), silver (Ag) and lanthanoids, and salts with organic acids. These light stabilizers may be used alone or in combination.

[0108] Examples of the antioxidant include, but are not limited to, phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol. These antioxidants may be used alone or in combination.

[0109] Examples of processing and heat stabilizers include, but are not limited to, phosphorus-based stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethyl phosphine, and diphenylbutyl phosphine. These stabilizers may be used alone or in combination.

[0110] Examples of the light resistance stabilizer include, but are not limited to, benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole. These light resistance stabilizers may be used alone or in combination.

[0111] The scattering particles are preferably inorganic particles having a refractive index of 1.7 to 2.8, such as titania, zirconia, alumina, ceria, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfide, and titanium or zirconium hydroxide.

[0112] In the color-changing composition of the present invention, the content of these additives can be set depending on the molar absorption coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the size, thickness, and transmittance of the color-changing member to be produced. The content (lower limit) of these additives is 1.0 × 10 relative to 100 parts by weight of the binder resin. -3 It is preferable that the amount is 1.0×10 parts by weight or more. -2 It is more preferable that the amount is 1.0×10 parts by weight or more. -1The content (upper limit) of these additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, and particularly preferably 10 parts by weight or less, relative to 100 parts by weight of the binder resin.

[0113] <Solvent> The color-changing composition of the present invention may further contain a solvent in addition to the at least one luminescent material and binder resin described above. A solvent that can adjust the viscosity of the resin in a fluid state and that does not excessively affect the luminescence and durability of the luminescent material is preferred. Examples of such solvents include water, 2-propanol, ethanol, toluene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, cyclohexane, tetrahydrofuran, acetone, terpineol, Texanol, 1,2-dimethoxyethane, methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, and propylene glycol monomethyl ether acetate. The color-changing composition of the present invention may use one of these solvents, or two or more of these solvents in combination. Among these solvents, toluene, methyl ethyl ketone, methyl acetate, ethyl acetate, and tetrahydrofuran are preferred because they leave little residual solvent after drying.

[0114] In the color conversion member described below according to an embodiment of the present invention, the amount of residual solvent in the color conversion layer of the color conversion member (the amount of solvent remaining in the color conversion layer after drying) is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and particularly preferably 0.5% by mass or less, from the viewpoint of further improving the durability of the color conversion member. The amount of residual solvent in the color conversion layer can be measured by gas chromatography.

[0115] <Method for Producing Color-Converting Composition> An example of a method for producing a color-converting composition according to an embodiment of the present invention is described below. In this method, the luminescent material, binder resin, and, if necessary, other additives and solvents are mixed to a predetermined composition, and then the mixture is homogeneously mixed or kneaded using a stirrer / kneader to obtain a color-converting composition. Examples of stirrers / kneaders include homogenizers, planetary stirrers, three-roller stirrers, ball mills, planetary ball mills, and bead mills. After mixing or dispersing, or during the mixing or dispersing process, degassing is preferably performed under vacuum or reduced pressure conditions. It is also possible to premix certain components or to perform treatments such as aging. It is also possible to remove the solvent using an evaporator to achieve a desired solids concentration.

[0116] <Color conversion member> A color conversion member according to an embodiment of the present invention (hereinafter sometimes abbreviated as the color conversion member of the present invention) contains the above-mentioned color conversion composition or a cured product thereof. The shape of the color conversion member is not particularly limited. For example, the shape of the color conversion member may be layered, particulate, fibrous, or the like. One embodiment of the color conversion member of the present invention is a color conversion sheet. The color conversion sheet has a color conversion layer containing the color conversion composition of the present invention, or a color conversion layer formed by curing the color conversion composition.

[0117] The color conversion member of the present invention may have a single color conversion layer or may have multiple color conversion layers. When the color conversion member has multiple color conversion layers, the color conversion layers may be laminated directly or via an intermediate layer such as an adhesive layer. Furthermore, the color conversion member of the present invention may have a substrate layer or a barrier layer as necessary, or may have two or more of these layers.

[0118] The substrate layer of the color conversion member of the present invention is not particularly limited, and layers made of known substrates such as metals, films, glass, ceramics, and paper can be used. Among these, glass and resin films are preferably used. As the resin film, films made of resins such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyphenylene sulfide, polycarbonate, polypropylene, polyimide, aramid, and silicone are preferred. To facilitate peeling of the sheet, the surface of the substrate layer may be previously subjected to a release treatment. Similarly, to improve adhesion between layers, the surface of the substrate layer may be previously subjected to an easy-adhesion treatment.

[0119] When the substrate layer is a film-like layer, the thickness of the substrate layer is not particularly limited, but the lower limit is preferably 12 μm or more, more preferably 38 μm or more, and the upper limit is preferably 5000 μm or less, more preferably 3000 μm or less.

[0120] Furthermore, as the substrate constituting the substrate layer, for example, members such as a barrier film, a light guide plate, a diffusion plate, a diffusion film, a prism sheet, a reflective polarizing film, a wavelength-selective reflection film, a wavelength-selective transmission film, and a wavelength-selective absorption film can be used.

[0121] The barrier layer of the color conversion member of the present invention is preferably one that suppresses the penetration of oxygen, moisture, heat, etc. into the color conversion layer. The color conversion member of the present invention may have two or more such barrier layers. For example, the color conversion member of the present invention may have a barrier layer on both sides of the color conversion layer, or may have a barrier layer on one side of the color conversion layer.

[0122] The color conversion member of the present invention preferably has an oxygen barrier layer as one embodiment of the barrier layer. Having an oxygen barrier layer in the color conversion member of the present invention is preferable because it can suppress oxidative degradation of the light-emitting material in the color conversion layer due to singlet oxygen generated by a dye-sensitization mechanism or the like. Furthermore, when the color conversion member of the present invention has a compound having a structure represented by the above-mentioned general formula (1) in the color conversion layer and the compound is a delayed fluorescent material, the delayed fluorescent material in the color conversion layer exhibits significantly better durability than conventional organic light-emitting materials in the absence of oxygen. Therefore, it is more preferable that the color conversion member of the present invention has an oxygen barrier layer. This is because delayed fluorescent materials have a long lifetime and can quickly convert a triplet excited state, which is prone to react with surrounding molecules, into a singlet excited state, thereby making it less likely that the delayed fluorescent material will deteriorate due to reactions between the triplet excited state and the surrounding molecules.

[0123] Examples of the oxygen barrier layer include layers formed of inorganic oxides such as silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, zinc oxide, tin oxide, indium oxide, yttrium oxide, and magnesium oxide, inorganic nitrides such as silicon nitride, aluminum nitride, titanium nitride, and silicon carbonitride, metal oxide thin films or metal nitride thin films obtained by adding other elements to these, or films containing various resins such as polyvinylidene chloride, acrylic resins, silicone resins, melamine resins, urethane resins, fluorine resins, and polyvinyl alcohol resins such as saponified vinyl acetate. The oxygen barrier layer may contain two or more of these.

[0124] Representative structural examples of the color conversion member of the present invention include the structures of the color conversion sheets of the first to sixth examples shown below. Note that the color conversion member of the present invention is not limited to the structural examples of the color conversion sheet shown below.

[0125] Fig. 1 is a schematic cross-sectional view showing a first example of a color conversion member according to an embodiment of the present invention. As shown in Fig. 1, the first example color conversion member 1A is a color conversion sheet having a laminated structure of a substrate layer 10 and a color conversion layer 11. This color conversion layer 11 is a layer containing the color conversion composition of the present invention and is obtained, for example, by curing the color conversion composition of the present invention. In this structural example of color conversion member 1A, the color conversion layer 11 is laminated on the substrate layer 10.

[0126] 2 is a schematic cross-sectional view showing a second example of a color conversion member according to an embodiment of the present invention. As shown in Fig. 2, the second example color conversion member 1B is a color conversion sheet having a laminated structure of multiple base layers 10A, 10B and a color conversion layer 11. In this structural example of color conversion member 1B, color conversion layer 11 is sandwiched between multiple base layers 10A, 10B.

[0127] FIG. 3 is a schematic cross-sectional view showing a third example of a color conversion member according to an embodiment of the present invention. As shown in FIG. 3 , the third example color conversion member 1C is a color conversion sheet having a laminated structure of multiple base layers 10A and 10B, a color conversion layer 11, and multiple barrier layers 12A and 12B. In this structural example of color conversion member 1C, color conversion layer 11 is sandwiched between multiple barrier layers 12A and 12B, and the laminate of color conversion layer 11 and multiple barrier layers 12A and 12B is further sandwiched between multiple base layers 10A and 10B. Each of these multiple barrier layers 12A and 12B is an oxygen barrier layer that prevents deterioration of color conversion layer 11 due to oxygen in color conversion member 1C. Note that each of these multiple barrier layers 12A and 12B is not limited to being an oxygen barrier layer and may be a layer for preventing deterioration of color conversion layer 11 due to moisture or heat.

[0128] Fig. 4 is a schematic cross-sectional view showing a fourth example of a color conversion member according to an embodiment of the present invention. As shown in Fig. 4, the fourth example color conversion member 1D is a color conversion sheet having a laminated structure in which multiple color conversion layers 11A, 11B are sandwiched between multiple base layers 10A, 10B. In this structural example of color conversion member 1D, a laminate of multiple color conversion layers 11A, 11B is formed by stacking the color conversion layer 11A and the color conversion layer 11B in this order on the base layer 10A, and then stacking another base layer 10B on top of this color conversion layer 11B. In other words, color conversion member 1D includes multiple base layers 10A, 10B and multiple color conversion layers 11A, 11B, and the multiple color conversion layers 11A, 11B are sandwiched between the multiple base layers 10A, 10B.

[0129] 5 is a schematic cross-sectional view showing a fifth example of a color conversion member according to an embodiment of the present invention. As shown in FIG. 5, the fifth example of a color conversion member 1E is a color conversion sheet having a laminated structure in which an intermediate layer 13 is sandwiched between multiple color conversion layers 11A, 11B, and the laminate of these multiple color conversion layers 11A, 11B and the intermediate layer 13 is sandwiched between multiple base layers 10A, 10B. In this structural example of color conversion member 1E, the laminate of multiple color conversion layers 11A, 11B and the intermediate layer 13 is laminated on base layer 10A in the order of color conversion layer 11A, intermediate layer 13, and color conversion layer 11B. Furthermore, another base layer 10B is laminated on top of color conversion layer 11B. That is, the color conversion member 1E comprises a plurality of base layers 10A, 10B, a plurality of color conversion layers 11A, 11B, and an intermediate layer 13, and contains a laminated structure of color conversion layer 11B / intermediate layer 13 / color conversion layer 11A sandwiched between these plurality of base layers 10A, 10B.

[0130] Fig. 6 is a schematic cross-sectional view showing a sixth example of a color conversion member according to an embodiment of the present invention. As shown in Fig. 6, the sixth example of a color conversion member 1F is a color conversion sheet having a laminated structure in which an intermediate layer 13 is sandwiched between multiple color conversion layers 11A, 11B, a laminate of these multiple color conversion layers 11A, 11B and the intermediate layer 13 is sandwiched between multiple barrier layers 12A, 12B, and a laminate of these multiple color conversion layers 11A, 11B, the intermediate layer 13, and the multiple barrier layers 12A, 12B is sandwiched between multiple base layers 10A, 10B. These multiple barrier layers 12A, 12B are formed so as to sandwich the laminate of the multiple color conversion layers 11A, 11B with the intermediate layer 13 interposed between them on both sides in the stacking direction. In this structural example of the color conversion member 1F, the barrier layer 12A, the color conversion layer 11A, the intermediate layer 13, the color conversion layer 11B, and the barrier layer 12B are laminated in this order on the base layer 10A. As a result, a laminate having a layered structure of barrier layer 12B / color conversion layer 11B / intermediate layer 13 / color conversion layer 11A / barrier layer 12A is formed on this base material layer 10A. Furthermore, as shown in Figure 6, base material layer 10B is laminated on top of barrier layer 12B, which is at the top end in the stacking direction of this laminate.

[0131] In each of the color conversion members 1A, 1B, 1C, 1D, 1E, and 1F shown in Figures 1 to 6, the layers of the laminated structure may be in direct contact with each other or may be laminated via an adhesive layer (not shown).

[0132] Another embodiment of the color conversion member of the present invention (different from the color conversion sheet described above) is a color conversion substrate. The color conversion substrate, for example, comprises a plurality of color conversion layers on a substrate. Although not shown, the color conversion substrate may have partition walls formed thereon, and the color conversion layers may be disposed between the partition walls (in recesses) in the color conversion substrate.

[0133] The color conversion member of the present invention may further have an auxiliary layer having a light diffusion layer, an adhesive layer, an anti-reflection function, an anti-glare function, an anti-reflection and anti-glare function, a hard coat function (abrasion resistance function), an anti-static function, an anti-fouling function, an electromagnetic wave shielding function, an infrared ray blocking function, an ultraviolet ray blocking function, a polarizing function, a color-tuning function, or the like, depending on the required functions.

[0134] <Method for Manufacturing Color Conversion Member> The method for manufacturing a color conversion member according to an embodiment of the present invention is not particularly limited as long as it can mold the color conversion composition of the present invention into a desired shape. For example, a method can be used in which the color conversion composition of the present invention is applied to a substrate and dried to form a color conversion layer in the color conversion member of the present invention. When the binder resin contained in the color conversion composition of the present invention is a thermosetting resin, the color conversion composition can be applied to a base such as a substrate and then heat-cured to form a color conversion layer. When the binder resin contained in the color conversion composition of the present invention is a photocurable resin, the color conversion composition can be applied to a base such as a substrate and then photocured to form a color conversion layer. Other examples include a method in which the color conversion composition of the present invention is kneaded while heating and then molded using an extruder, and a method in which the color conversion composition of the present invention is placed in a mold and molded by heating, cooling, drying, etc.

[0135] In the above-described method for producing a color conversion member, the color conversion composition can be applied using a reverse roll coater, blade coater, comma coater, slit die coater, direct gravure coater, offset gravure coater, kiss coater, natural roll coater, air knife coater, roll blade coater, two-stream coater, rod coater, wire bar coater, applicator, dip coater, curtain coater, spin coater, knife coater, etc. However, the application of the color conversion composition is not limited to these.

[0136] In the above-described method for producing a color-changing member, the color-changing composition after application can be dried using a common heating device such as a hot air dryer or an infrared dryer. In this case, the heating temperature is preferably 60°C to 200°C, and the heating time is preferably 2 minutes to 4 hours. It is also possible to heat and cure the composition in stages using a method such as step curing.

[0137] When the color-changing layer is formed by heat-curing the color-changing composition, a hot air oven or the like can be used as the heating device. In this case, the heating conditions can be selected depending on the binder resin in the color-changing composition. For example, the heating temperature is preferably 100°C to 300°C, and the heating time is preferably 1 minute to 2 hours.

[0138] When forming a color conversion layer by photocuring the color conversion composition, it is preferable to irradiate the color conversion composition with high-energy light such as ultraviolet light. In this case, the light irradiation conditions can be selected depending on the binder resin in the color conversion composition. For example, the wavelength of the irradiated light is preferably 200 nm to 500 nm, and the irradiation dose is preferably 10 mJ / cm. 2 ~10 J / cm 2 is preferred.

[0139] In the above-described manufacturing method of the color conversion member, it is also possible to change the base material layer as needed after the color conversion layer is produced. In this case, simple methods include, for example, a method of replacing the base material layer using a hot plate, or a method using a vacuum laminator or a dry film laminator.

[0140] <Light Source Unit> A light source unit according to an embodiment of the present invention (hereinafter sometimes abbreviated as the light source unit of the present invention) is configured to include at least a light source and the above-described color conversion composition or color conversion member. When the light source unit of the present invention includes a color conversion composition, the arrangement of the light source and the color conversion composition is not particularly limited. The color conversion composition may be applied directly to the light source, or the color conversion composition may be applied to a substrate such as a film or glass that is separated from the light source. When the light source unit of the present invention includes a color conversion member, the arrangement of the light source and the color conversion member is not particularly limited. The light source and the color conversion member may be closely attached to each other, or a remote phosphor type in which the light source and the color conversion member are separated from each other may be used. The light source unit of the present invention may further include a color filter to enhance color purity, or an optical member such as a prism sheet, a reflective polarizing film, or a diffusion film to improve brightness and uniformity of emitted light.

[0141] One embodiment of the light source unit of the present invention includes a color conversion member (color conversion sheet) having the configuration exemplified in Fig. 5 described above, with the light source located below the plane of Fig. 5 (below base layer 10A), and a prism sheet and a reflective polarizing film laminated above the plane of Fig. 5 (above base layer 10B). A diffuser plate may be provided between the light source and the color conversion member shown in Fig. 5, and a reflector plate may be provided below the light source.

[0142] Another embodiment of the light source unit of the present invention is a configuration including a light source and a light guide plate, and a color conversion layer formed by directly applying the color conversion composition of the present invention to the light output side of the light guide plate. In a light source unit having this configuration, a light diffusion layer and a wavelength selective transmission layer may be further formed on the color conversion layer.

[0143] The light source unit of the present invention is useful for various light sources such as spatial illumination, backlighting, etc. Specifically, the light source unit of the present invention can be used for applications such as displays, lighting devices, interiors, signs, and billboards, and is particularly suitable for use in displays and lighting devices.

[0144] <Light Source> The light source provided in the light source unit of the present invention can be any light source that emits light in a wavelength region that can be absorbed by the light-emitting material used in the color-converting composition of the present invention. In principle, any excitation light source can be used, such as a hot cathode tube, a cold cathode tube, a fluorescent light source such as inorganic electroluminescence (EL), an organic EL element light source, a light-emitting diode (LED) light source, an incandescent light source, or sunlight. Among these, from the viewpoint of color purity, an LED or an organic EL element is preferred as the light source, and an LED is more preferred.

[0145] For example, in display and lighting applications, from the viewpoint of enhancing the color purity of blue light, an LED or organic EL element having a maximum emission wavelength in the range of 400 nm to 500 nm is a preferred light source. Furthermore, as the light source, a blue LED having a maximum emission wavelength in the range of 430 nm to 480 nm is more preferred, and a blue LED having a maximum emission wavelength in the range of 445 nm to 470 nm is particularly preferred.

[0146] The light source may have one emission peak or two or more emission peaks, but in order to improve color purity, it is preferable that the light source has one emission peak. It is also possible to use a combination of multiple light sources with different emission peaks.

[0147] <Display, lighting device> A display according to an embodiment of the present invention includes at least a light source unit having a light source and a color-converting composition or a color-converting member as described above. For example, in a display such as a liquid crystal display, the light source unit described above is used as a backlight unit.

[0148] Furthermore, an illumination device according to an embodiment of the present invention includes at least a light source unit having a light source and a color conversion composition or a color conversion member as described above. For example, this illumination device is configured to emit white light by combining a blue LED light source as the light source unit with a color conversion composition or a color conversion member that converts blue light from the blue LED light source into light with a longer wavelength.

[0149] The present invention will be described below with reference to examples, but the present invention is not limited to the following examples. First, the evaluation methods and materials such as light-emitting materials in the examples and comparative examples will be described.

[0150] <Measurement of Emission Spectrum> In measuring the emission spectrum, a fluorescence spectrophotometer (Fluoromax 4, manufactured by Horiba, Ltd.) was used to measure the fluorescence spectrum when the prepared color conversion member in each example and comparative example was excited with excitation light having a wavelength of 460 nm.

[0151] <Brightness Evaluation> In the brightness evaluation, in each example and comparative example, a current was passed through a light emitting device equipped with the prepared color conversion member and a blue LED element (manufactured by USHIO EPITEX Corporation; model number SMBB450H-1100, emission peak wavelength: 450 nm), and a brightness of 8000 cd / m 2The blue LED element was turned on at a luminance of 10 ...

[0152] <Measurement of Color Conversion Characteristics> In measuring the color conversion characteristics, each color conversion sheet and prism sheet to be evaluated were placed on a surface light-emitting device equipped with a blue LED element with an emission peak wavelength of 450 nm. Current was passed through the surface light-emitting device in this state to light up the blue LED element, and the emission spectrum and chromaticity of the light color-converted from the blue light of the blue LED element by the color conversion sheet were measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta, Inc.).

[0153] <Calculation of Color Gamut> In calculating the color gamut, the color gamut in the (x, y) color space when the color purity is improved by the color filter was calculated from the emission spectrum obtained by measuring the color conversion characteristics and the spectral data of the transmittance of the color filter, and the coverage rate of the calculated color gamut with respect to the DCI-P3 standard was calculated. As an evaluation result of the color gamut in this (x, y) color space, "A" indicates that the coverage rate is 91% or more. "B" indicates that the coverage rate is 86% or more and 90% or less. "C" indicates that the coverage rate is 81% or more and 85% or less. "D" indicates that the coverage rate is 80% or less. In this evaluation result, the higher the coverage rate, the higher the degree of fulfillment of the DCI-P3 standard and the better the color reproducibility of the color conversion sheet.

[0154] <Light-emitting material> In the following examples and comparative examples, compounds G-1 to G-4 and compound R-1 were used as the light-emitting material contained in a color conversion member such as a color conversion sheet. Compounds G-1 to G-4 and compound R-1 are the compounds shown below.

[0155]

[0156] <Scattering Agent> In the following examples and comparative examples, titanium dioxide particles "JR-301" (manufactured by Teika Co., Ltd.) were used as the scattering agent.

[0157] Example 1 In Example 1, first, PMMA resin "BR-85" (manufactured by Mitsubishi Chemical Corporation) was used as the binder resin, and 0.3 parts by weight of compound G-1 as the luminescent material, 3 parts by weight of JR-301 as a scattering agent, and 300 parts by weight of ethyl acetate as a solvent were mixed with 100 parts by weight of this binder resin. Thereafter, this mixture was stirred and degassed for 20 minutes at 1000 rpm using a planetary stirring and degassing device "Mazerustar" (registered trademark) KK-400 (manufactured by Kurabo Industries, Ltd.). This gave a resin composition for producing a color conversion layer (the color conversion composition of Example 1).

[0158] Next, the resin composition for preparing the color conversion layer obtained above was applied onto "Cerapeel" BLK (manufactured by Toray Advanced Film Co., Ltd.) using a film applicator, and then heated and dried at 120°C for 20 minutes, thereby forming a color conversion layer with an average film thickness of 20 µm.

[0159] Next, a hydrochloric acid solution prepared by mixing 0.1N hydrochloric acid (4g) and water (5g) was slowly added dropwise to a mixed solution of tetraethyl orthosilicate (1.2g), 2-propanol (0.5g), and methanol (0.5g). Then, a polyvinyl alcohol resin (0.4g) with a saponification degree of 98 mol% or more was mixed into this mixed solution as a polyol-based resin, and the mixture was stirred. This produced a resin solution for producing an oxygen barrier layer.

[0160] This resin liquid for producing an oxygen barrier layer was applied by bar coating onto an alumina-deposited polyethylene terephthalate film "Barrierox" (registered trademark) 1011HG (manufactured by Toray Industries, Inc., thickness 12 μm), and then dried at 150°C for 1 minute. This formed a coating layer of the resin liquid. Furthermore, a coating layer with an average thickness of about 1 μm was formed on this coating layer, thereby producing an oxygen barrier laminate film, which is an example of a barrier layer. The oxygen permeability of this oxygen barrier laminate film was about 0.2 cc / m 2 In Example 1, two sheets of this oxygen barrier laminate film were prepared.

[0161] Next, a thermosetting adhesive layer was formed by coating on the polyvinyl alcohol resin layer of one of the oxygen barrier laminate films, and the color conversion layer was laminated on top of that. Then, the "Cerapeel" BLK was peeled off from the color conversion layer.

[0162] Finally, a thermosetting adhesive layer was formed by coating on the polyvinyl alcohol resin layer of another oxygen barrier laminate film, and the resulting thermosetting adhesive layer was laminated on the color conversion layer after peeling off the "Cerapeel" BLK. This produced a sheet-like color conversion member (e.g., the color conversion sheet illustrated in Figure 3). The average film thickness of all thermosetting adhesive layers included in this color conversion member was 0.50 μm.

[0163] When light from a blue LED element (blue light) was color-converted using the sheet-like color conversion member prepared as described above, high-color-purity green light was obtained, with a peak wavelength of 520 nm and a half-width of the emission spectrum at the peak wavelength of 21 nm, when only the green light emission region was extracted. Furthermore, the luminance measured for the color conversion member of Example 1 was 35,700 cd / m 2 Example 1 showed an improvement in luminance of about 3.3 times compared to Comparative Example 1 described later. The luminescent material of Example 1 and the evaluation results are as shown in Table 1 described later.

[0164] In Examples 2 and 3, sheet-like color conversion members were produced and evaluated in the same manner as in Example 1, except that the luminescent material was changed to one shown in Table 1 and the amount of the luminescent material mixed was adjusted to be the same as that of Compound G-1 in Example 1. The luminescent materials and evaluation results in each of Examples 2 and 3 are as shown in Table 1.

[0165] In Comparative Example 1, a sheet-like color conversion member was produced and evaluated in the same manner as in Example 1, except that the luminescent material was changed to one shown in Table 1 and the amount of the luminescent material mixed was adjusted to be the same as that of compound G-1 in Example 1. The luminescent material and evaluation results of Comparative Example 1 are shown in Table 1.

[0166]

[0167] Example 4 In Example 4, first, PMMA resin "BR-85" (manufactured by Mitsubishi Chemical Corporation) was used as the binder resin, and 0.12 parts by weight of compound G-1 as the luminescent material (a) and 300 parts by weight of ethyl acetate as the solvent were mixed with 100 parts by weight of this binder resin. The mixture was then stirred and degassed for 20 minutes at 1000 rpm using a planetary stirring and degassing device "Mazerustar" (registered trademark) KK-400 (manufactured by Kurabo Industries, Ltd.). This resulted in a resin composition for producing layer (A) (one of the color-changing compositions of Example 4) for producing layer (A), which is the first color-changing layer.

[0168] As described above, PMMA resin "BR-85" (manufactured by Mitsubishi Chemical Corporation) was used as the binder resin. 100 parts by weight of this binder resin were mixed with 0.02 parts by weight of compound R-1 as the luminescent material (b), 3 parts by weight of JR-301 as a scattering agent, and 300 parts by weight of ethyl acetate as a solvent. The mixture was then stirred and degassed for 20 minutes at 1000 rpm using a planetary stirring and degassing device "Mazerustar" (registered trademark) KK-400 (manufactured by Kurabo Industries, Ltd.). This yielded a resin composition for producing the second color conversion layer, layer (B) (one of the color conversion compositions of Example 4).

[0169] Next, the resin composition for preparing layer (A) obtained above was applied onto a first base layer, "Lumirror" (registered trademark) U48 (manufactured by Toray Industries, Inc., thickness 50 μm), using a film applicator, and then heated and dried for 20 minutes at 120° C. This formed a unit including layer (A) (first color conversion layer) with an average film thickness of 20 μm.

[0170] In the same manner as above, the resin composition for preparing the (B) layer was applied using a film applicator onto the second base layer, "Lumirror" (registered trademark) U48 (manufactured by Toray Industries, Inc., thickness 50 μm), and then heated and dried for 20 minutes at 120° C. This formed a unit including the (B) layer (second color conversion layer) with an average film thickness of 16 μm.

[0171] Next, the two units were heat-laminated so that the (A) layer and the (B) layer were directly laminated together, thereby producing a sheet-like color conversion member (e.g., the color conversion sheet shown in Fig. 4) having a laminated structure of "first base material layer / (A) layer / (B) layer / second base material layer."

[0172] When light from a blue LED element was color-converted using the sheet-like color conversion member prepared as described above, the emission spectrum showed sharp emission peaks in the red, green, and blue regions, and white light with an XY color coordinate of (X, Y) = (0.22, 0.23) was obtained. Extracting only the green light emission region, a high-color-purity green emission was obtained, with a peak wavelength of 524 nm and a half-width of the emission spectrum at the peak wavelength of 23 nm. Extracting only the red light emission region, a high-color-purity red emission was obtained, with a peak wavelength of 628 nm and a half-width of the emission spectrum at the peak wavelength of 49 nm. The color gamut area in the (x, y) color space was 94% of the color gamut area specified by the DCI standard. The luminescent material and evaluation results of Example 4 are shown in Table 2 below.

[0173] In Table 2, "Color coordinates (X, Y)" are the values ​​of the XY color coordinates. "Color gamut area" is the area of ​​the color gamut in the (x, y) color space. Also, "A" to "D" in the "Color gamut area" column indicate the evaluation results of the area of ​​this color gamut. This is the same for each table.

[0174] In each of Examples 5 and 6 and Comparative Example 2, the luminescent material (a) was changed to one shown in Table 2, and the amount of luminescent material (a) mixed was adjusted to be the same as that of compound G-1 in Example 4, and sheet-like color conversion members were produced and evaluated in the same manner as in Example 4. The luminescent materials and evaluation results in each of Examples 5 and 6 and Comparative Example 2 are as shown in Table 2.

[0175]

[0176] As described above, the color-converting composition, color-converting member, and light source unit, display, and lighting device each including the color-converting composition, color-converting member, according to the present invention are suitable for achieving both high color reproducibility and high brightness.

[0177] 1A, 1B, 1C, 1D, 1E, 1F Color conversion member 10, 10A, 10B Base layer 11, 11A, 11B Color conversion layer 12A, 12B Barrier layer 13 Intermediate layer

Claims

1. A color-changing composition comprising at least one luminescent material and a binder resin, wherein the at least one luminescent material comprises a compound having a structure represented by the following general formula (1): (In general formula (1), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf, and ring Zg are each independently a substituted or unsubstituted aryl ring having 5 to 30 ring members, or a substituted or unsubstituted heteroaryl ring having 5 to 30 ring members. Z 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1 When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4 When R is NRa, the substituent R may be bonded to the ring Zd or the ring Z to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O. The substituents R and R C are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C Each of may be further substituted with selected substituents, and those substituents may be further substituted with selected substituents.

2. The color-changing composition according to claim 1, wherein the structure represented by general formula (1) is a structure represented by the following general formula (2): In the general formula (2), ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf and ring Zg are benzene rings. 1 ~Z 4 each independently represents a direct bond, an oxygen atom, a sulfur atom, a nitrogen atom, NRa (a nitrogen atom having a substituent Ra), C=O (a carbonyl group), S(=O) or S(=O)2. Z 1 When R is NRa, the substituent R may be bonded to the ring Za or the ring Zb to form a ring. 4 When R is NRa, the substituent R may be bonded to the ring Zd or the ring Z to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent R), or P=O. C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 are each independently a substituent selected from a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, and a fused ring or an aliphatic ring formed between adjacent substituents. C , R a1 ~R a3 , R b1 ~R b4 , R d1 ~R d3 , R e1 ~R e4 , R f1 ~R f4 and R g1 ~R g4 Each of may be further substituted with selected substituents, and those substituents may be further substituted with selected substituents.

3. The color-changing composition according to claim 1, characterized in that in said general formula (1), at least one of ring Za, ring Zb, ring Zc, ring Zd, ring Ze, ring Zf and ring Zg has one or more groups selected from 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, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an aldehyde group, a carboxy group, an ester group, an acyl group, a sulfonyl group, a sulfonate ester group, a sulfonamide group, a nitro group, a silyl group, a siloxanyl group, a boryl group, a phosphine oxide group, an alkylamine and a cyclic amine.

4. The color-changing composition according to claim 1, wherein in said general formula (1), at least one of ring Za and ring Zd has an aryl group.

5. The color-changing composition according to claim 1, wherein in said general formula (1), at least one of ring Za and ring Zd has a phenyl group.

6. In the general formula (1), Z 1 ~Z 4 The color-changing composition according to claim 1 , wherein is an oxygen atom, a nitrogen atom, or NRa.

7. The color-changing composition according to claim 1, wherein in said general formula (1), E is a boron atom.

8. In the general formula (2), R a2 and R d2 The color-changing composition of claim 2 , wherein is a phenyl group.

9. The color-changing composition according to claim 1, characterized in that the compound having the structure represented by general formula (1) exhibits luminescence with a peak wavelength observed in the region of 500 nm or more and less than 580 nm when excited with excitation light.

10. A color-changing member comprising the color-changing composition according to any one of claims 1 to 9 or a cured product thereof.

11. The color conversion member according to claim 10, which has an oxygen barrier layer.

12. A light source unit comprising: a light source; and the color conversion member according to claim 10.

13. The light source unit according to claim 12, wherein the light source is a light emitting diode having a maximum light emission in the wavelength range of 430 nm to 500 nm.

14. A display comprising the light source unit according to claim 12.

15. A lighting device comprising the light source unit according to claim 12.

Images