Compound

Abstract

To provide a material for wavelength conversion based on a dipyrromethene boron complex compound having excellent solubility in a medium and exhibiting a sufficiently large molar absorption coefficient, a wavelength conversion member, a light emitting device, and a compound.SOLUTION: The invention provides: a material for wavelength conversion containing a compound represented by the general formula (1) in the figure; a wavelength conversion member based on the material for wavelength conversion; a light emitting device; and a compound. In the formula (1), R1 to R7 each represent a hydrogen atom or a substituent, and R8 and R9 each represent a specific substituent, provided that at least one of R1 to R9 has a partial structure represented by the formula (A) in the figure. In the formula (A), R11 to R16 each represent a hydrogen atom or an alkyl group, and the symbol * represents a bonding site.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound suitable for use in a wavelength conversion material, a wavelength conversion member, and a light emitting device.

Background Art

[0002] Light emitting diodes (LEDs) that emit white light are widely used in display devices such as various displays. In recent years, there has been an increasing interest in energy conservation issues, and white LEDs are also rapidly spreading as lighting devices such as fluorescent lamps. A white LED is usually composed of a combination of an LED and a phosphor. This phosphor generally has a function or property (hereinafter referred to as wavelength conversion characteristics) of absorbing light of a specific wavelength (incident light) emitted from an LED and emitting light of a specific wavelength different from this light (emitted light), and is formed from a wavelength conversion material containing a fluorescent compound having such characteristics and, if necessary, a resin or the like. Among fluorescent compounds, organic fluorescent compounds generally have better wavelength conversion efficiency than inorganic fluorescent compounds. As a wavelength conversion material using such an organic fluorescent compound, a material containing a dipyrromethene boron complex compound in which a dipyrromethene compound is coordinated to a boron atom at two positions and a resin has been proposed. For example, Patent Document 1 describes a color conversion composition (wavelength conversion material) containing a compound in which an electron-withdrawing group is introduced as a dipyrromethene boron complex compound represented by a specific general formula (1), or a compound in which R in the general formula (1) 7 is an aryl group or a heteroaryl group, and a binder resin.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] Although not described as a wavelength conversion material, Patent Document 2 describes a coloring composition containing a dipyrromethene-based complex compound represented by a specific general formula (I) and an infrared absorbing compound having an absorption maximum at a wavelength of 700 nm or more, and a color filter formed using this composition.

[0005] In recent years, there has been a demand to further improve the wavelength conversion characteristics by improving the wavelength conversion efficiency or increasing the luminance of the wavelength conversion material. Dipyrromethene boron complex compounds used in wavelength conversion materials are required to have sufficient solubility in a medium (for example, a solvent, a resin, or a monomer) from the viewpoint of developing a higher luminance wavelength conversion material. By using a dipyrromethene boron complex compound having high solubility, when producing a wavelength conversion material, performance degradation due to aggregation or production suitability degradation due to precipitation is less likely to occur. That is, the dipyrromethene boron complex compound can be present in a high concentration and uniformly in the resulting wavelength conversion material. As a result, it becomes possible to obtain a high luminance wavelength conversion material. Furthermore, when the solubility is low, it is necessary to change the dissolution conditions such as atomization by heating or ultrasonic treatment, or to remove insoluble components by treatment such as filter filtration, which may cause a decrease in the productivity of the wavelength conversion material. Also, increasing the luminous efficiency (wavelength conversion efficiency), which can be represented by the product of the molar extinction coefficient and the quantum yield, is an important factor in increasing the luminance of the wavelength conversion material. However, as a result of investigations by the present inventors, it has been found that the dipyrromethene boron complex compound used in the wavelength conversion material described in Patent Document 1 has insufficient solubility and is not considered to have a large molar extinction coefficient, and there is room for improvement.

[0006] The present invention aims to provide a wavelength conversion material using a dipyrromethene boron complex compound that is excellent in solubility in a medium (hereinafter, also simply referred to as "solubility") and exhibits a sufficiently large molar extinction coefficient. Further, the present invention aims to provide a dipyrromethene boron complex compound that is excellent in solubility and exhibits a sufficiently large molar extinction coefficient. Furthermore, the present invention aims to provide a wavelength conversion member and a light-emitting device using the above wavelength conversion material.

Means for Solving the Problems

[0007] The present inventor has found that a dipyrromethene boron complex compound having a specific structure in which a specific substituent having both hydrophobicity and bulkiness is introduced onto the dipyrromethene skeleton is excellent in solubility and has an increased molar extinction coefficient. The present invention has been completed based on these findings through further studies.

[0008] That is, the problems of the present invention have been solved by the following means. 〔1〕 A wavelength conversion material containing a compound represented by the following general formula (1).

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0009] In the present invention, "wavelength conversion" means converting (incident) light of a specific wavelength into (emitted) light of a wavelength different from that specific wavelength (usually a longer wavelength than the specific wavelength), and is also referred to as "color conversion".

Advantages of the Invention

[0010] The wavelength conversion material, wavelength conversion member, and light-emitting device of the present invention are made of a dipyrromethene boron complex compound that has excellent solubility and exhibits a sufficiently large molar extinction coefficient, and have excellent luminous efficiency. Further, the dipyrromethene boron complex compound of the present invention has excellent solubility and exhibits a sufficiently large molar extinction coefficient.

Embodiments for Carrying Out the Invention

[0011] In the present invention, when there are a plurality of substituents or linking groups, etc. (hereinafter referred to as substituents, etc.) represented by specific symbols or formulas, or when a plurality of substituents, etc. are defined simultaneously, unless otherwise specified, each of the substituents, etc. may be the same as or different from each other. This also applies to the definition of the number of substituents, etc. Further, when a plurality of substituents, etc. are close to each other (particularly when adjacent), unless otherwise specified, they may be linked to each other to form a ring. Further, unless otherwise specified, a ring, for example, an alicyclic ring, an aromatic ring, or a heterocyclic ring, may be further condensed to form a condensed ring. In the present invention, unless otherwise specified, for a double bond, when both E-type and Z-type exist in the molecule, either one or a mixture thereof may be used. In the present invention, unless otherwise specified, each component that can constitute the wavelength conversion material (compounds represented by general formula (1), resins, and other components other than these) may be contained singly or in two or more kinds in the wavelength conversion material. This also applies to the components that can constitute the wavelength conversion member. In the present invention, when calculating the content of each component in the wavelength conversion material, the solid content means components other than the solvent.

[0012] In the present invention, the term "compound" (including complexes) is used to mean not only the compound itself, but also its salts and ions. Further, it includes those in which a part of the structure is changed as long as the effects of the present invention are not impaired. Furthermore, for compounds in which substitution or non-substitution is not specified, it means that they may have any substituent as long as the effects of the present invention are not impaired. This also applies to substituents and linking groups. In the present invention, when defining the number of carbon atoms of a certain group, unless otherwise specified in the present invention or this specification, the number of carbon atoms means the total number of carbon atoms of the entire group. That is, when this group is in a form having further substituents, it means the total number of carbon atoms including such substituents.

[0013] In the present invention, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. In the present invention, the composition includes, in addition to a mixture with a constant component concentration (where each component is uniformly dispersed), a mixture in which the component concentration varies within a range that does not impair the intended wavelength conversion function.

[0014] [Material for wavelength conversion] The material for wavelength conversion of the present invention contains a compound (dipyrromethene boron complex compound) represented by the following general formula (1). The compound represented by this general formula (1) is a fluorescent compound, and due to the wavelength conversion characteristics exhibited by the compound represented by this general formula (1), the material for wavelength conversion of the present invention converts the wavelength of incident light into light with a longer wavelength. This is the same in the wavelength conversion unit using the material for wavelength conversion of the present invention, which will be described later. The wavelength conversion unit of the present invention converts the wavelength of incident light into light with a longer wavelength due to the wavelength conversion characteristics exhibited by the compound represented by formula (1). The wavelength conversion material of the present invention generally does not contain a compound (for example, an infrared absorbing compound) that absorbs the emission (fluorescence) of a compound represented by the general formula (1). The form of the wavelength conversion material of the present invention may be any of a solution form, a dispersion form, a semi-solid (such as a slurry) form, and a solid form. The wavelength conversion material of the present invention preferably has a form in which all components are uniformly mixed, that is, a composition form. Components other than the compound represented by the general formula (1) contained in the wavelength conversion material of the present invention include resins, raw material monomers, solvents, and other additives described later. Details of each form are as described in the preparation method of the wavelength conversion material of the present invention described later. The wavelength conversion material of the present invention can be stably stored by controlling storage conditions such as light shielding and low temperature as necessary.

[0015] <Compound represented by the general formula (1)> The wavelength conversion material of the present invention contains a compound represented by the following general formula (1).

Chemical formula

[0016] In the formula, R 1 ~R 7 represents a hydrogen atom or a substituent. R 8 and R 9 represent an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxy group, a sulfanyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a cyano group, or a halogen atom. However, at least one of R 1 ~R 9 has a partial structure represented by the following formula (A).

[0017] (i) R 1 ~R 7 R 1 ~R 7 each independently represents a hydrogen atom or a substituent. R 1 ~R 7Examples of the substituent that can be adopted include the substituents in the substituent group T described later.

[0018] R 1 and R 7 Among these, an alkyl group, an aryl group, an amino group, or an acylamino group is preferably mentioned. Examples of the substituent that the above alkyl group, aryl group, amino group, and acylamino group may have include the substituents in the substituent group T described later, and for example, a sulfonylamino group is mentioned. Among these, R 1 and R 7 are more preferably an amino group, and even more preferably -NH2.

[0019] R 2 and R 6 Among these, an alkoxycarbonyl group or a cyano group is preferably mentioned. Examples of the above alkoxycarbonyl group preferably include a partial structure represented by the following formula (A). Among these, R 2 and R 6 more preferably have a partial structure based on the partial structure represented by the following formula (A).

[0020] R 3 and R 5 Among these, an alkyl group or an aryl group is preferably mentioned.

[0021] R 4 Among these, a hydrogen atom, an alkyl group, an aryl group, or a cyano group is preferably mentioned. Examples of the substituent that the above alkyl group and aryl group may have include the substituents in the substituent group T described later, and for example, a halogen atom (preferably a fluorine atom), a halogenated alkyl group, an alkyl group, an alkoxy group, an alkylaryl group, and an aryl group are mentioned. Among these, R 4 is more preferably a hydrogen atom or an alkyl group.

[0022] (ii) R 8 and R 9 R 8 and R 9 R and R each represent an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxy group, a sulfanyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a cyano group or a halogen atom (preferably a fluorine atom), and an alkyl group, an alkenyl group, an alkoxy group, an aryl group, a cyano group or a halogen atom is preferred. Yes. R 8 or R 9 Examples of the alkyl group, cycloalkyl group, aliphatic heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, sulfanyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, aryl group, heteroaryl group, cyano group or halogen atom that R or R can take include the alkyl group, cycloalkyl group, aliphatic heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, sulfanyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, aryl group, heteroaryl group, cyano group or halogen atom in the substituent group T described later. Examples of the substituent that the above alkyl group, cycloalkyl group, aliphatic heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, aryl group and heteroaryl group may have include the substituents in the substituent group T described later, for example, a halogen atom (preferably a fluorine atom) and an aryl group. R 8 and R 9 It is preferable that at least one of R and R is a halogenated alkyl group, a halogenated alkyloxy group or a cyano group, more preferably a halogenated alkyl group or a cyano group, and even more preferably a halogenated alkyl group.

[0023] (iii) A partial structure represented by formula (A) R 1 ~R 9 At least one of the above has a partial structure represented by the following formula (A). [ka]

[0024] In the formula, R 11 ~R 16 indicates a hydrogen atom or an alkyl group, and * indicates a bonding site. R 11 ~R 16 Examples of the alkyl group that can be taken as the substituent include the alkyl groups in the substituent group T described below. R 11 ~R 16 The combination of R 11 , R 13 and R 15 is a hydrogen atom, and R 12 , R 14 and R 16 is preferably a hydrogen atom or an alkyl group, and R 11 , R 12 , R 14 ~R 16 is a hydrogen atom, and R 13 is more preferably a hydrogen atom or an alkyl group, and R 11 , R 12 , R 14 ~R 16 is a hydrogen atom, and R 13 More preferably, is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0025] R 1 ~R 9 As an embodiment in which at least one of the above has a partial structure represented by formula (A), R 1 ~R 9 is itself a group represented by the above formula (A) (i.e., * in formula (A) is R 1 ~R 9 (the bond of R) and 1 ~R 9The substituent that can be adopted may further have a partial structure represented by the above formula (A) as a substituent (that is, * in the formula (A) is R 1 ~R 9 and may be in the form of a bond that is substituted by a substituent that can be adopted, and R 1 ~R 9 itself is preferably in the form of a group represented by the above formula (A). R 1 ~R 9 In the form where the substituent that can be adopted further has a partial structure represented by the above formula (A) as a substituent, for example, a form where an alkyl group, an aryl group, an alkoxy group or a heteroaryl group further has a partial structure represented by the above formula (A) as a substituent is preferably exemplified.

[0026] Among the above R 1 ~R 9 , at least one of R 2 and R 6 preferably has a partial structure represented by the above formula (A), and it is more preferable that both R 2 and R 6 have a partial structure represented by the above formula (A).

[0027] The compound represented by the above general formula (1) is preferably a compound represented by the following general formula (2) or (3), and more preferably a compound represented by the following general formula (3).

[0028]

Chemical formula

[0029] In the formula, R 1 , R 3 ~R 9 , R 12 , R 14 and R 16 are R 1 , R 3 ~R 9 , R 12 , R 14 and R 16 in the above general formula (1).is synonymous with.

[0030] <Compound represented by general formula (1A)> The compound of the present invention is a compound represented by the following general formula (1A).

[0031] [Chemical formula]

[0032] In the formula, R 1 ~R 7 represents a hydrogen atom or a substituent. R 8 and R 9 represent an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxy group, a sulfanyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a cyano group or a halogen atom. However, at least one of R 8 and R 9 is a halogenated alkyl group, a halogenated alkyloxy group or a cyano group, and at least one of R 1 ~R 9 has a partial structure represented by the following formula (A).

[0033] [Chemical formula]

[0034] In the formula, R 11 ~R 16 represents a hydrogen atom or an alkyl group, and * represents a bonding site.

[0035] The compound represented by general formula (1A) is the same as the compound represented by the above general formula (1) except that at least one of R 8 and R 9 is a halogenated alkyl group, a halogenated alkyloxy group or a cyano group. Therefore, R 1 ~R 9And as the partial structure represented by the formula (A), R 8 and R 9 except that at least one of them is a halogenated alkyl group, a halogenated alkyloxy group or a cyano group, R in the above general formula (1) 1 ~R 9 and the description of the partial structure represented by the formula (A) can be applied.

[0036] The compound represented by the above general formula (1A) is preferably a compound represented by the following general formula (2A) or (3A).

[0037]

Chemical formula

[0038] In the formula, R 1 , R 3 ~R 9 , R 12 , R 14 and R 16 are synonymous with R 1 , R 3 ~R 9 , R 12 , R 14 and R 16 in the above general formula (1A).

[0039] - Substituent group T - In the present invention, preferred substituents include substituents selected from the following substituent group T. Also, in this specification, when only described as a substituent, this refers to the substituent group T, and when only each group, for example, an alkyl group, is described, the corresponding group of this substituent group T is applied. Furthermore, in this specification, when an alkyl group is described separately from a cyclic (cyclo)alkyl group, the alkyl group is used in the sense that it includes linear alkyl groups and branched alkyl groups. On the other hand, when the alkyl group is not described separately from the cyclic alkyl group and there is no particular notice, the alkyl group is used in the sense that it includes linear alkyl groups, branched alkyl groups, and cycloalkyl groups. This also applies to groups containing a group capable of adopting a cyclic structure (such as an alkyl group, alkenyl group, alkynyl group, etc.) (such as an alkoxy group, alkylthio group, alkenyloxy group, etc.) and compounds containing a group capable of adopting a cyclic structure. When a group can form a cyclic skeleton, the lower limit of the number of atoms of the group forming the cyclic skeleton is 3 or more, preferably 5 or more, regardless of the lower limit of the number of atoms specifically described below for groups capable of adopting this structure. In the description of the following substituent group T, for example, in order to clarify a group having a linear or branched structure and a group having a cyclic structure such as an alkyl group and a cycloalkyl group, they may be described separately.

[0040] Examples of the groups included in the substituent group T include the following groups. An alkyl group (preferably having 1 to 20 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, pentyl, heptyl, 1-ethylpentyl, benzyl, 2-ethoxyethyl, 1-carboxymethyl, trifluoromethyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, such as vinyl, allyl, oleyl, etc.), an alkynyl group (preferably having 2 to 20 carbon atoms, such as ethynyl, butadiynyl, phenylethynyl, etc.), a cycloalkyl group (preferably having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, etc.), a cycloalkenyl group (preferably having 5 to 20 carbon atoms, such as cyclopentenyl, cyclohexenyl, etc.), an aryl group (preferably having 6 to 26 carbon atoms, such as phenyl, 1-naphthyl, 4-methoxyphenyl, 2-chlorophenyl, 3-methylphenyl, etc.), a heterocyclic group (preferably having 2 to 20 carbon atoms, more preferably a 5-membered or 6-membered heterocyclic group having at least one oxygen atom, sulfur atom, or nitrogen atom, such as 2-pyridyl, 4-pyridyl, 2-imidazolyl, 2-benzimidazolyl, 2-thiazolyl, 2-oxazolyl, etc.), an alkoxy group (preferably having 1 to 20 carbon atoms, such as methoxy, ethoxy, isopropyloxy, benzyloxy, etc.), an alkenyloxy group (preferably having 2 to 20 carbon atoms, such as vinyloxy, allyloxy, etc.), an alkynyloxy group (preferably having 2 to 20 carbon atoms, such as 2-propynyloxy, 4-butynyloxy, etc.), a cycloalkyloxy group (preferably having 3 to 20 carbon atoms, such as cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, etc.), an aryloxy group (preferably having 6 to 26 carbon atoms, such as phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, etc.), a heterocyclic oxy group (such as imidazolyl oxy, benzimidazolyl oxy, thiazolyl oxy, benzothiazolyl oxy, triazinyl oxy, purinyl oxy),

[0041] An alkoxycarbonyl group (preferably having 2 to 20 carbon atoms, such as ethoxycarbonyl, 2-ethylhexyloxycarbonyl, etc.), a cycloalkoxycarbonyl group (preferably having 4 to 20 carbon atoms, such as cyclopropyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, etc.), an aryloxycarbonyl group (preferably having 6 to 20 carbon atoms, such as phenyloxycarbonyl, naphthyloxycarbonyl, etc.), an amino group (preferably having 0 to 20 carbon atoms, including alkylamino group, alkenylamino group, alkynylamino group, cycloalkylamino group, cycloalkenylamino group, arylamino group, heterocyclic amino group, for example, unsubstituted amino (-NH2), N,N-dimethylamino, N,N-diethylamino, N-ethylamino, N-allylamino, N-(2-propynyl)amino, N-cyclohexylamino, N-cyclohexenylamino, anilino, pyridylamino, imidazolylamino, benzimidazolylamino, thiazolylamino, benzothiazolylamino, triazinylamino, etc.), a sulfamoyl group (preferably having 0 to 20 carbon atoms, preferably an alkyl, cycloalkyl or aryl sulfamoyl group, for example, N,N-dimethylsulfamoyl, N-cyclohexylsulfamoyl, N-phenylsulfamoyl, etc.), an acyl group (preferably having 1 to 20 carbon atoms, such as acetyl, cyclohexylcarbonyl, benzoyl, etc.), an acyloxy group (preferably having 1 to 20 carbon atoms, such as acetyloxy, cyclohexylcarbonyloxy, benzoyloxy, etc.), a carbamoyl group (preferably having 1 to 20 carbon atoms, preferably an alkyl, cycloalkyl or aryl carbamoyl group, for example, N,N-dimethylcarbamoyl, N-cyclohexylcarbamoyl, N-phenylcarbamoyl, etc.),

[0042] Acylamino group (preferably an acylamino group having 1 to 20 carbon atoms, such as acetylamino, cyclohexylcarbonylamino, benzoylamino, 2-pyrrolidinone-1-yl, etc.), sulfonamide group (preferably having 0 to 20 carbon atoms, and preferably an alkyl, cycloalkyl or aryl sulfonamide group, such as methanesulfonamide, benzenesulfonamide, N-methylmethanesulfonamide, N-cyclohexylsulfonamide, N-ethylbenzenesulfonamide, etc.), alkylthio group (preferably having 1 to 20 carbon atoms, such as methylthio, ethylthio, isopropylthio, benzylthio, etc.), cycloalkylthio group (preferably having 3 to 20 carbon atoms, such as cyclopropylthio, cyclopentylthio, cyclohexylthio, 4-methylcyclohexylthio, etc.), arylthio group (preferably having 6 to 26 carbon atoms, such as phenylthio, 1-naphthylthio, 3-methylphenylthio, 4-methoxyphenylthio, etc.), alkyl, cycloalkyl or arylsulfonyl group (preferably having 1 to 20 carbon atoms, such as methylsulfonyl, ethylsulfonyl, cyclohexylsulfonyl, benzenesulfonyl, etc.),

[0043] A silyl group (preferably having 1 to 20 carbon atoms, and preferably a silyl group substituted with alkyl, aryl, alkoxy and aryloxy, for example, triethylsilyl, triphenylsilyl, diethylbenzylsilyl, dimethylphenylsilyl, etc.), a silyloxy group (preferably having 1 to 20 carbon atoms, and preferably a silyloxy group substituted with alkyl, aryl, alkoxy and aryloxy, for example, triethylsilyloxy, triphenylsilyloxy, diethylbenzylsilyloxy, dimethylphenylsilyloxy, etc.), a hydroxyl group, a cyano group, a nitro group, a halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), a carboxyl group, a sulfo group, a phosphonyl group, a phosphoryl group, a boric acid group, more preferably an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkoxycarbonyl group, a cycloalkoxycarbonyl group, the above amino group, an acylamino group, a cyano group or a halogen atom, and particularly preferably an alkyl group, an alkenyl group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, an amino group, an acylamino group or a cyano group.

[0044] Unless otherwise specified, the substituents selected from the substituent group T also include groups formed by combining a plurality of the above groups. For example, when a compound or a substituent contains an alkyl group, an alkenyl group, etc., these may or may not be substituted. Also, when an aryl group, a heterocyclic group, etc. are included, they may be monocyclic or condensed rings, and may or may not be substituted.

[0045] Specific examples of the compound represented by the general formula (1) are shown below, but the present invention is not limited to these compounds.

[0046]

Chemical formula

[0047]

Chemical formula

[0048]

Chem.

[0049] The content of the compound represented by the general formula (1) in the wavelength conversion material of the present invention, that is, the content of the compound represented by the general formula (1) per 1 g of the solid content in the wavelength conversion material of the present invention is not particularly limited and is appropriately determined according to the molar extinction coefficient of this compound and the required properties (for example, quantum yield, light resistance, heat and humidity resistance, etc.). For example, the above content is preferably 0.01 to 50 μmol / g or less, more preferably 0.05 to 10 μmol / g or less, still more preferably 0.1 to 1.0 μmol / g, and most preferably 0.1 to 0.5 μmol / g. In the wavelength conversion material of the present invention, the content of the compound represented by the general formula (1) is not particularly limited as long as it satisfies the content per 1 g of the solid content described above. However, with respect to 100 parts by mass of the resin described later, for example, 0.0005 to 5 parts by mass is preferable, 0.0025 to 1 part by mass or less is more preferable, and 0.005 to 0.1 part by mass is still more preferable. In addition, the compound represented by the general formula (1) contained in the wavelength conversion material of the present invention may be one kind or two or more kinds. When the wavelength conversion material of the present invention contains two or more kinds of the compounds represented by the general formula (1), the above content is the total content of two or more kinds of compounds.

[0050] The compound represented by the general formula (1) can be synthesized with reference to ordinary synthesis methods or known synthesis methods, for example, the synthesis methods described in Patent Document 1 or Patent Document 2. Further, it can be synthesized in accordance with the synthesis methods of Compounds (1-1), (1-2) and (2-1) described in the examples described later.

[0051] <Resin> The wavelength conversion material of the present invention may contain a resin. Particularly when forming a wavelength conversion member described later, it usually contains a resin as a binder (also referred to as a binder resin). Further, when forming the luminescent latex particles described later, resin particles can be contained. In the present invention, as the binder resin, a thermoplastic polymer compound, a thermosetting or photocurable polymer compound, or a mixture thereof can be used. In the present invention, the "polymer compound" means that when the polymer compound is a thermosetting or photocurable polymer compound, it also includes the compound (monomer) or polymerization precursor that forms the polymer compound. In addition, when the wavelength conversion material of the present invention takes a form other than particles (non-particle form), the binder resin is not used in the form of particles.

[0052] The binder resin used in the present invention is preferably transparent or translucent (the transmittance of visible light (wavelength 300 to 830 nm) is 50% or more). Examples of such binder resins include (meth)acrylic resins, polyvinyl cinnamate, polycarbonate, polyimide, polyamideimide, polyesterimide, polyetherimide, polyetherketone, polyetheretherketone, polyethersulfone, polysulfone, polyparylene, polyester, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, polyurethane, polyvinyl alcohol, cellulose acylate, fluorinated resin, silicone resin, epoxy silicone resin, phenol resin, alkyd resin, epoxy resin, maleic acid resin, melamine resin, urea resin, aromatic sulfonamide, benzoguanamine resin, silicone elastomer, aliphatic polyolefin (e.g., polyethylene, polypropylene), cyclic olefin copolymer, and the like. As the binder resin, polystyrene, (meth)acrylic resin, cellulose acylate or silicone resin, or a mixture of two or more thereof is preferred. The mass average molecular weight of the binder resin is not particularly limited, but for example, it is preferably 1,000 to 100,000. The binder resin contained in the wavelength conversion material of the present invention may be one kind or two or more kinds. The content of the binder resin in the solid content of the wavelength conversion material is not particularly limited, but can be, for example, 50% by mass or more, and preferably 90% by mass or more.

[0053] <Solvent> The wavelength conversion material of the present invention can also be a liquid material containing a solvent. The solvent to be used is not particularly limited, and examples thereof include the solvents described in the method for preparing the wavelength conversion material described later. The content of the solvent in the wavelength conversion material is not particularly limited, but can be, for example, 50% by mass or more, and preferably 70% by mass or more.

[0054] <Additive> The wavelength conversion material of the present invention may contain various additives usually used in wavelength conversion materials. Examples of such additives include, for example, photoluminescence phosphors other than the compounds represented by the general formula (1) defined in the present invention, inorganic phosphors, dyes for color tone correction, processing, oxidation and heat stabilizers (antioxidants, phosphorus-based processing stabilizers, etc.), light resistance stabilizers (ultraviolet absorbers, etc.), silane coupling agents, and further, organic acids, matting agents, radical scavengers, deterioration inhibitors, fillers (for example, silica, glass fibers, glass beads), plasticizers, lubricants, flame retardants (for example, organic halogen compounds), flame retardant aids, antistatic agents, charge imparting agents, impact resistance improvers, discoloration inhibitors, mold release agents (for example, higher fatty acid esters of monohydric or polyhydric alcohols), fluidity improvers, reactive or non-reactive diluents, and the like. Note that the wavelength conversion material of the present invention preferably does not contain a fluorescence absorbing substance such as an infrared absorbing compound in order to effectively exhibit the wavelength conversion function.

[0055] The photoluminescence phosphor other than the compound represented by the general formula (1) defined in the present invention is not particularly limited, but known photoluminescence phosphors (dyes) can be mentioned. Specific examples of the above various additives include "other components" described in Patent Document 1, or those described in JP-A-2011-241160, and these descriptions are preferably incorporated herein. Further, the content of the additive is not particularly limited and is appropriately determined within a range that does not impair the object of the present invention.

[0056] The compound represented by the general formula (1) contained in the wavelength conversion material of the present invention and the compound represented by the general formula (1A) of the present invention (hereinafter, also referred to as "the compound of (1) or (1A) defined in the present invention") are both excellent in solubility in a solvent or a raw material monomer constituting a resin and have a large molar extinction coefficient. The reason for this is not clear, but it is considered as follows. That is, the specific partial structure represented by the formula (A) that the compound of (1) or (1A) defined in the present invention has at least one in the compound has high hydrophobicity and a bulky structure. Therefore, the affinity with the medium is enhanced by the specific partial structure represented by the formula (A), and the intermolecular interaction of the compound of (1) or (1A) defined in the present invention is suppressed by steric hindrance, so that it is considered that the solubility can be effectively increased. Further, the compound of (1) or (1A) defined in the present invention has a large spread between the HOMO (highest occupied molecular orbital) and the LUMO (lowest unoccupied molecular orbital), and a large overlap between the HOMO and the LUMO, and it is considered that the molar extinction coefficient can be made larger. Further, as shown in the examples described later, the compound of (1) or (1A) defined in the present invention can exhibit a quantum yield as excellent as that of the dipyrromethene boron complex compound used in conventional wavelength conversion materials, and can exhibit excellent luminous efficiency in combination with the improvement of the molar extinction coefficient. That is, the ratio of the light intensity of the emitted light to the light intensity of the incident light can be increased more. As described above, the compound of formula (1) or (1A) defined in the present invention, which has excellent solubility, is less likely to cause a decrease in performance due to aggregation or a decrease in production suitability due to precipitation when producing a wavelength conversion material, and can be uniformly present at a high concentration in the wavelength conversion material. In addition, it has a large molar extinction coefficient and excellent quantum yield. As a result, a desired high brightness can be achieved in the wavelength conversion material using this compound. The same applies to the wavelength conversion part and the light emitting device of the present invention.

[0057] In addition, with the spread of light emitting devices such as display devices and lighting devices, the fluorescent compounds and wavelength conversion materials containing these fluorescent compounds used in these devices are required to have not only the above excellent solubility and excellent luminous efficiency, but also high light resistance, and further high durability against moisture and heat (moisture and heat resistance). The compound of general formula (1) or (1A) defined in the present invention and the wavelength conversion material of the present invention can also exhibit excellent light resistance and moisture and heat resistance in addition to excellent solubility and excellent luminous efficiency. Although the details of the reason are not yet clear, it is considered as follows. The compound of general formula (1) or (1A) defined in the present invention can obtain the action of preventing the proximity of reactive substances due to steric hindrance, preventing the proximity of water (reactive substances) due to hydrophobization, and preventing hue change due to suppression of the association of the compound of general formula (1) or (1A) defined in the present invention by the partial structure represented by the above formula (A). It is considered that excellent light resistance and moisture and heat resistance can be exhibited by these actions.

[0058] <Method for preparing wavelength conversion material> The method for preparing the wavelength conversion material of the present invention is not particularly limited, and for example, the following methods A to C can be mentioned.

[0059] Method A: A method including a step of dissolving or suspending the compound represented by general formula (1) defined in the present invention, optionally a binder resin and additives, in a solvent if necessary. In this method A, the solution obtained by the above step can also be dried.

[0060] Method B: A method including a step of curing a mixture containing a compound represented by the general formula (1) defined in the present invention, and, if necessary, a monomer and / or a polymerization precursor for forming a binder resin, and further an additive For example, a method in which a compound represented by the general formula (1) defined in the present invention and, if necessary, an additive are mixed (dispersed) with a monomer or a polymerization precursor of a thermosetting or photocurable polymer, and then the monomer or the polymerization precursor is polymerized can be mentioned. Further, a method in which a compound represented by the general formula (1) defined in the present invention and, if necessary, an additive are mixed (dissolved or suspended) in a solution of a monomer or a polymerization precursor, and then the solvent is removed to polymerize the monomer or the polymerization precursor can be mentioned.

[0061] Method C: A method including a step of melting a mixture of a compound represented by the general formula (1) defined in the present invention and, if necessary, a binder resin and an additive For example, a method in which a compound represented by the general formula (1) defined in the present invention and, if necessary, an additive are dispersed in a binder resin and then melted can be mentioned.

[0062] In the above Methods A to C, when no solvent is used and when the solution is dried, the wavelength conversion material of the present invention can be prepared as a solid mixture. The method of mixing (dissolving, suspending or dispersing) the compound represented by the general formula (1) defined in the present invention with a solvent or a binder resin is not particularly limited, and methods such as stirring, melt blending, and mixing with a powder such as a binder resin can be used. The method of melt blending can be applied without particularly limiting known methods, and the melt blending conditions can also be set as appropriate. For example, as the apparatus and melt temperature conditions used for melt blending or dispersion, for example, the apparatuses and temperature conditions described in JP-A-2011-241160 can be applied, and these descriptions are preferably incorporated herein.

[0063] When using a solvent, examples of the solvent include hydrocarbons such as toluene, ketone compounds, halogenated hydrocarbons such as methylene chloride, ester compounds, alcohol compounds such as methanol, various solvents such as ether compounds, and furthermore, polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolidinone, dimethyl sulfoxide, and water. The solvent may be used alone or in combination of two or more. Specific examples of each of the above solvents include the organic solvents described in JP-A-2011-241160, and the descriptions thereof are preferably incorporated herein. The method for removing the solvent is not particularly limited, and usually includes a method of evaporating and removing by leaving at room temperature or blowing air, a method of evaporating and removing by heating, a method of evaporating and removing under reduced pressure (below atmospheric pressure), or a method of combining these.

[0064] The polymerization method of the monomer and / or the polymerization precursor in Method B is not particularly limited, and may be thermal polymerization or photopolymerization. Thermal polymerization can be carried out by a conventional method. Examples of the thermal polymerization method include a method in which a catalyst is added to a mixture of the above monomer and / or polymerization precursor and the compound represented by the general formula (1) defined in the present invention as necessary, and then heated. Examples of the thermal polymerization method and its conditions, and further the catalyst used and its amount used include the methods described in JP-A-2011-241160, and the descriptions of this publication are preferably incorporated herein. Photopolymerization can be carried out by a conventional method. Examples of the photopolymerization method include a method in which a photopolymerization initiator is added to a mixture of the above monomer and / or polymerization precursor and the compound represented by the general formula (1) defined in the present invention as necessary, and then irradiated with light. Examples of the photopolymerization method and its conditions, and further the polymerization initiator used and its amount used include the methods described in JP-A-2011-241160, and the descriptions of this publication are preferably incorporated herein.

[0065] When the binder resin is a silicone resin, a method of polymerizing by an addition curing reaction is preferred. The addition curing reaction of the silicone resin can also be carried out by a conventional method. For example, it is preferred to polymerize by a hydrosilylation reaction between an organosiloxane having a polymerizable reaction group (for example, an alkenyl group) and a hydrogen siloxane having a hydrogen atom bonded to a silicon atom. The conditions of the hydrosilylation reaction are not particularly limited, but heating at room temperature or higher, for example, 50 to 200 °C, in the presence of an addition reaction catalyst (for example, a platinum catalyst) if desired, can be mentioned.

[0066] [Luminescent particles] By forming the wavelength conversion material of the present invention into the shape of particles, it can also be used as luminescent particles. The material of the particles is not particularly limited. For example, when using organic polymer particles such as polystyrene beads, the compound represented by the above general formula (1) can be made into luminescent particles by impregnating the particles or adsorbing it on the particle surface, etc. Usually, it mainly exists in an impregnated state in the particles. In addition, inorganic particles such as silica gel or glass beads can also be used. In this case, the compound represented by the above general formula (1) can be made into luminescent particles by adsorbing it on the particle surface, etc. Specific examples of the material of the particles include homopolymers obtained by polymerizing monomers such as styrene, methacrylic acid, glycidyl (meth) acrylate, butadiene, vinyl chloride, vinyl acetate acrylate, methyl methacrylate, ethyl methacrylate, phenyl methacrylate, or butyl methacrylate, and copolymers obtained by polymerizing two or more monomers, cellulose, and cellulose derivatives, etc. A latex in which the above homopolymer or copolymer is uniformly suspended may also be used. In addition, examples of the particles include other organic polymer powders, inorganic substance powders, microorganisms, blood cells, cell membrane fragments, liposomes, microcapsules, etc. As the particles, latex particles are preferred.

[0067] When using latex particles, specific examples of the latex material include polystyrene, styrene-acrylic acid copolymer, styrene-methacrylic acid copolymer, styrene-glycidyl (meth)acrylate copolymer, styrene-styrene sulfonate copolymer, methacrylic acid polymer, acrylic acid polymer, acrylonitrile-butadiene-styrene copolymer, vinyl chloride-acrylic acid ester copolymer, polyvinyl acetate acrylate, and the like. As the latex, a copolymer containing at least styrene as a monomer is preferable, and a copolymer of styrene and acrylic acid or methacrylic acid is particularly preferable. The method for producing the latex is not particularly limited, and it can be produced by any polymerization method. However, when the above-mentioned luminescent particles are labeled with an antibody and used, the presence of a surfactant makes it difficult to immobilize the antibody. Therefore, for the production of the latex, surfactant-free emulsion polymerization, that is, emulsion polymerization without using an emulsifier such as a surfactant, is used, or after producing the latex by emulsion polymerization using an emulsifier such as a surfactant, it is preferable to remove or reduce the surfactant by purification. The method for removing or reducing the surfactant is not particularly limited, but a purification method in which the operation of removing the supernatant after sedimenting the latex by centrifugation is repeated is preferable. In the production of the latex, when surfactant-free emulsion polymerization is used, the average particle size can be controlled in the range of 80 to 300 nm by changing the reaction temperature, the monomer composition ratio (for example, the ratio of styrene to acrylic acid), and the amount of the polymerization initiator. In the production of the latex, when emulsion polymerization using a surfactant (for example, sodium dodecyl sulfate) is used, the average particle size can be controlled in the range of 30 to 150 nm by changing the amount of the surfactant, the reaction temperature, the monomer composition ratio (for example, the ratio of styrene to acrylic acid), and the amount of the polymerization initiator. The average particle size of the latex particles is synonymous with the average particle size of the luminescent particles described later, and the measurement method for the average particle size of the luminescent particles described later is also applied to the measurement method.

[0068] <Luminescent particles> By containing the compound represented by the general formula (1), the above luminescent particles suppress the aggregation of the compound in the latex particles due to the partial structure represented by the formula (A) that the compound represented by the general formula (1) has. As a result, when the number of moles of the compound (compound amount) with respect to the latex of the compound represented by the general formula (1) is increased, a fluorescence intensity corresponding to the compound amount can be obtained, and high luminance can be exhibited. The incident light and the emitted light for causing the above luminescent particles to emit light have the same meaning as the incident light and the emitted light in the above wavelength conversion material.

[0069] The emission maximum wavelength of the luminescent particles can be measured using a commercially available fluorescence spectrophotometer. For example, it can be measured using a fluorescence spectrophotometer RF-5300PC manufactured by Shimadzu Corporation.

[0070] The quantum yield of the luminescent particles is the ratio of the number of photons emitted as fluorescence to the number of photons absorbed by the luminescent particles. The quantum yield exhibited by the above luminescent particles is preferably 0.25 or more, more preferably 0.4 or more, still more preferably 0.5 or more, even more preferably 0.6 or more, and particularly preferably 0.7 or more. The upper limit of the quantum yield is not particularly limited, but generally it is 1.0 or less. The quantum yield of the above luminescent particles can be measured using a commercially available quantum yield measuring device. For example, it can be measured using an absolute PL quantum yield measuring device C9920-02 manufactured by Hamamatsu Photonics K.K.

[0071] (Method for measuring the average particle diameter (average particle size) of luminescent particles) The average particle size of the above-mentioned luminescent particles varies depending on the material of the particles, the concentration range for measuring the analyte, the measuring instrument, etc., but is preferably in the range of 0.001 to 10 μm (more preferably 0.01 to 1 μm), more preferably in the range of 30 to 500 nm, still more preferably in the range of 50 to 300 nm, particularly preferably in the range of 80 to 200 nm, and most preferably in the range of 100 to 150 nm. The average particle size of the luminescent particles that can be used in the present invention can be measured with a commercially available particle size distribution meter or the like. As the method for measuring the particle size distribution, optical microscopy, confocal laser microscopy, electron microscopy, atomic force microscopy, static light scattering method, laser diffraction method, dynamic light scattering method, centrifugal sedimentation method, electrical pulse measurement method, chromatography method, ultrasonic attenuation method, etc. are known, and devices corresponding to each principle are commercially available. Among these measurement methods, it is preferable to measure the average particle size of the luminescent particles using the dynamic light scattering method in view of the particle size range and ease of measurement. Commercially available measuring devices using dynamic light scattering include NanoTrack UPA (Nikkiso Co., Ltd.), dynamic light scattering type particle size distribution measuring device LB-550 (HORIBA, Ltd.), concentrated system particle size analyzer FPAR-1000 (Otsuka Electronics Co., Ltd.), etc. In the present invention, the average particle size is determined as the median diameter (d = 50) measured under the conditions of 25 °C, a viscosity of 0.8872 CP, and a refractive index of water of 1.330.

[0072] <Method for producing luminescent particles> The method for producing the above-mentioned luminescent particles is not particularly limited, but can be produced by mixing at least one compound represented by the above general formula (1) with particles. For example, the above-mentioned luminescent particles can be prepared by adding the compound represented by the above general formula (1) to particles such as latex particles. More specifically, the above-mentioned luminescent particles can be produced by adding a solution containing the compound represented by the above general formula (1) to a dispersion of particles containing any one or more of water and water-soluble organic solvents (tetrahydrofuran, methanol, etc.) and stirring.

[0073] <Dispersion> According to the present invention, a dispersion containing the above-mentioned luminescent particles is provided. The dispersion can be produced by dispersing the above-mentioned luminescent particles in a dispersion medium. Examples of the dispersion medium include water, an organic solvent, or a mixture of water and an organic solvent. As the organic solvent, alcohols such as methanol, ethanol, and isopropanol, and ether solvents such as tetrahydrofuran can be used. The solid content concentration of the luminescent particles in the dispersion is not particularly limited, but generally it is 0.1 to 20% by mass, preferably 0.5 to 10% by mass, and more preferably 1 to 5% by mass.

[0074] <Utilization of Luminescent Particles> When the number of moles (compound amount) of the compound represented by the general formula (1) with respect to the latex of the above-mentioned luminescent particles is increased, fluorescence intensity corresponding to the compound amount can be obtained, and high luminance can be exhibited. Therefore, the above-mentioned luminescent particles can be suitably used in a fluorescence detection method or the like, for example, in a fluorescence detection method for quantifying proteins, enzymes, or inorganic compounds.

[0075] [Light-Emitting Device] The light-emitting device of the present invention has a wavelength conversion unit using the wavelength conversion material of the present invention and a light source, and emits light of a target wavelength. In the present invention, a unit composed of a wavelength conversion unit and a light source may be referred to as a wavelength conversion unit. This wavelength conversion unit has a function of absorbing light (incident light) emitted (radiated) from the light source and emitting (wavelength-converting) light of a specific wavelength different from this light (usually, a longer wavelength than the wavelength of the incident light). At this time, the wavelength conversion unit absorbs all or part of the light from the light source and irradiates light of a specific wavelength. For example, when the light-emitting device of the present invention emits white light as a whole (such as a white LED or white lighting), it absorbs part of the blue light from the light source and emits red light or green light, and combined with the blue light from the light source, the device as a whole can emit white light. At this time, the wavelength conversion unit exhibits a function of converting into red light or green light. As the structure of the light-emitting device of the present invention, a conventionally known structure can be applied without particular limitation. Details will be described later. In the light-emitting device of the present invention, the arrangement of the wavelength conversion unit and the light source is not particularly limited. The wavelength conversion unit and the light source may be arranged in a state of being close to or in contact with each other, or may be arranged in a separated state or with other members interposed therebetween. As described above, the wavelength conversion material and the wavelength conversion unit of the present invention can also exhibit excellent light resistance and heat and humidity resistance. Therefore, the wavelength conversion unit and the light source can be arranged close to each other, or can be arranged in a state of being in contact with each other. Even if such an arrangement is adopted, the incident light can be wavelength-converted with excellent wavelength conversion efficiency to emit light as the emitted light, and can also emit light with a high quantum yield over a long period of time. The light-emitting device of the present invention can be used for a white LED or as a white LED. Even in this case, it can exhibit excellent wavelength conversion efficiency and can also exhibit excellent light resistance and heat and humidity resistance.

[0076] <Wavelength conversion unit> The wavelength conversion unit of the present invention is not particularly limited in its shape, dimensions, etc., as long as the wavelength conversion material of the present invention is used, and is appropriately set according to the application, etc. For example, the wavelength conversion unit used in the light-emitting device of the present invention may be the wavelength conversion material itself of the present invention or a molded body. When it is the wavelength conversion material itself of the present invention, it is usually formed by applying (coating or arranging) the wavelength conversion material of the present invention on the installation surface. In the case of a molded body, the shape is not particularly limited, and examples include a film shape, a plate shape (for example, a sheet shape, a film shape, a disk shape), a lens shape, a fiber shape, an optical waveguide shape, etc. One preferred embodiment is that the wavelength conversion unit is plate-shaped. In this case, the wavelength conversion unit (also referred to as a wavelength conversion filter) may be formed as a wavelength conversion layer using the wavelength conversion material of the present invention. The thickness of the wavelength conversion layer is not particularly limited, but for example, 10 to 3000 μm is preferred, and 30 to 2000 μm is more preferred.

[0077] The wavelength conversion unit may be a laminate (wavelength conversion member) provided on a substrate or the like. Examples of the substrate include a glass substrate and a resin substrate. Examples of the glass substrate include substrates made of various glasses such as soda lime glass, barium-strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium-borosilicate glass, and quartz. Examples of the resin substrate include substrates made of various resins such as polycarbonate, acrylic resin, polyethylene terephthalate, polyethersulfide, and polysulfone.

[0078] The wavelength conversion unit may have constituent members other than the substrate. Such constituent members are not particularly limited as long as they are commonly used for wavelength conversion members, and examples include a protective film (film) and the like.

[0079] The wavelength conversion unit can wavelength-convert incident light with excellent wavelength conversion efficiency and emit it as emitted light, and can also emit light with a high quantum yield over a long period of time. The quantum yield exhibited by the wavelength conversion unit is preferably 0.7 or more. The upper limit of the quantum yield is not particularly limited, but is generally 1.0 or less. In the present invention, the quantum yield can be measured using a commercially available quantum yield measuring device. For example, it can be measured for the wavelength conversion unit (thickness: 60 μm) using an absolute PL (photoluminescence) quantum yield measuring device: C9920-02 (manufactured by Hamamatsu Photonics).

[0080] When the wavelength conversion unit is a molded body, it is produced by molding the wavelength conversion material of the present invention into a predetermined shape. The molding method is not particularly limited, and examples include molding methods performed in a thermally molten state such as injection molding, and film-forming methods performed after melting the wavelength conversion material of the present invention. The film-forming method is not particularly limited, and examples include spin coating, roll coating, bar coating, Langmuir-Blodgett method, casting method, dipping method, screen printing method, bubble jet (registered trademark) method, inkjet method, vapor deposition method, electric field method, and the like. When the binder resin is a thermosetting resin or a photocurable resin, a mixture of the monomer and / or prepolymer of the binder resin and a compound represented by the general formula (1) defined in the present invention can be filled into a mold, or a film can be formed by the above-described film-forming method and polymerized by light or heat, and the above method can also be applied.

[0081] <Light source> The light source used in the light-emitting device of the present invention is not particularly limited as long as it emits an emission wavelength (wavelength light) capable of exciting at least the compound represented by the general formula (1) defined in the present invention, preferably all the fluorescent compounds contained in the wavelength conversion part. Examples of such light sources include incandescent bulbs, metal halide lamps, HID lamps (High Intensity Discharge Lamps), xenon lamps, sodium lamps, mercury lamps, fluorescent lamps, cold cathode tubes, cathodoluminescence, low-speed electron beam tubes, light-emitting diodes [e.g., GaP (red, green), GaP x As (1-x) (red, orange, yellow: 0 < x < 1), Al x Ga (1-x) As (red: 0 < x < 1), GaAs (red), SiC (blue), GaN (blue), ZnS, ZnSe], electroluminescence (e.g., inorganic EL using a ZnS matrix and a luminescent center, organic EL), lasers (e.g., gas lasers such as He-Ne lasers, CO2 lasers, Ar, Kr, He-Cd lasers, excimer lasers, nitrogen lasers, ruby lasers, yttrium-aluminum-garnet (YAG) lasers, glass lasers, etc., solid lasers, dye lasers, semiconductor lasers), sunlight, and the like. The light source is preferably a light-emitting diode, electroluminescence, or semiconductor laser, and more preferably a light-emitting diode.

[0082] As the light-emitting diode, a semiconductor light-emitting device having a light-emitting layer capable of emitting light with an emission wavelength capable of exciting at least the compound represented by the general formula (1) defined in the present invention is preferable. Examples of such a semiconductor light-emitting device include those having a light-emitting layer containing the above semiconductor. As the semiconductor other than the above semiconductor, a nitride semiconductor (In x Al y Ga (1-x-y) , 0 ≦ X, 0 ≦ Y, X + Y ≦ 1) that can emit light with a short wavelength capable of efficiently exciting the compound represented by the general formula (1) defined in the present invention is preferable. More preferably, the light-emitting layer does not contain the compound represented by the general formula (1) defined in the present invention. The semiconductor contained in the light-emitting layer is preferably an inorganic semiconductor. Examples of the semiconductor structure include a homo structure, a hetero structure, or a double hetero structure having a MIS (Metal-Insulator-Silicon) junction, a PIN junction, a pn junction, etc. The emission wavelength can be variously selected depending on the material of the light-emitting layer or its degree of mixed crystal. Further, it can also be a single quantum well structure or a multiple quantum well structure in which the light-emitting layer is formed into a thin film where a quantum effect occurs.

[0083] When emitting white light in the light-emitting device of the present invention described later, considering the complementary color relationship with the emission wavelength from the compound represented by the general formula (1) defined in the present invention or the deterioration of the binder resin, the emission wavelength (excitation wavelength) of the light source is preferably 350 to 480 nm. To further improve the excitation and emission efficiencies of the light source and the compound represented by the general formula (1) defined in the present invention, respectively, the emission wavelength is more preferably 380 to 450 nm. The light-emitting diode is usually disposed on a substrate having a patterned metal such as a copper foil. Here, examples of the substrate material include insulating organic compounds or inorganic compounds (e.g., glass, ceramics). As the organic compound, various polymer materials (e.g., epoxy resin, acrylic resin) can be used. Further, the shape of the substrate is not particularly limited, and various shapes such as a plate shape, a cup shape, and a porous plate shape can be selected.

[0084] The above semiconductor laser is not particularly limited, but preferably operates based on the following mechanism. That is, a semiconductor is pn-junctioned, a forward bias is applied thereto, minority carriers at a high energy level are injected, electrons flowing into the p-type region are recombined with holes, and holes flowing into the n-type region are recombined with electrons. As a result, a mechanism can be mentioned in which electrons transition from a high energy level to a low energy level, and photons corresponding to the energy difference are emitted. Examples of materials for the semiconductor laser include Group IV elements such as germanium and silicon, and direct-transition type Group III-V and II-VI compounds that do not involve lattice vibration, such as GaAs and InP. Further, these materials may be not only binary systems, but also multi-component systems such as ternary, quaternary, and quinary systems. Also, the laminated structure may be a double heterostructure provided with a cladding layer, or may have a configuration including a lower cladding layer, an active layer, and an upper cladding layer. Furthermore, a multiple quantum well structure may be applied.

[0085] The light-emitting device of the present invention may optionally include a color filter, by which color purity can be adjusted. The color filter is not particularly limited as long as it is commonly used. Examples of pigments used in the color filter include various pigments such as perylene pigments, lake pigments, azo pigments, quinacridone pigments, anthraquinone pigments, anthracene pigments, isoindoline pigments, isoindolinone pigments, phthalocyanine pigments, triphenylmethane basic dyes, indanthrone pigments, indophenol pigments, cyanine pigments, and dioxazine pigments, or a pigment mixture of two or more of these pigments, and furthermore, a mixture of the above pigments or pigment mixture and a binder resin (in a solid state dissolved or dispersed).

[0086] In the light-emitting device of the present invention, the compound represented by the general formula (1) defined in the present invention can convert incident light from a light source, preferably incident light in the above wavelength region, into emitted light of a predetermined wavelength with excellent conversion efficiency and emit light, and can also emit light over a long period of time. The light emitted by the light-emitting device of the present invention as a whole may be only the light wavelength-converted by the compound represented by the general formula (1) defined in the present invention or the wavelength-converting unit, or may be a mixed light of this light and the above wavelength light from the light source.

[0087] <Configuration of the light-emitting device> The configuration of the light-emitting device of the present invention is not particularly limited, and the following configurations can be mentioned. As a specific configuration, for example, a light source / wavelength conversion unit, a light source / translucent substrate / wavelength conversion unit, a light source / wavelength conversion unit / translucent substrate, a light source / translucent substrate / wavelength conversion unit / translucent substrate, a light source / wavelength conversion unit / color filter, a light source / translucent substrate / wavelength conversion unit / color filter, a light source / wavelength conversion unit / translucent substrate / color filter, a light source / translucent substrate / wavelength conversion unit / translucent substrate / color filter, a light source / translucent substrate / wavelength conversion unit / color filter / translucent substrate, a light source / wavelength conversion unit / color filter / translucent substrate. In each of the above configurations, the wavelength conversion unit uses the wavelength conversion material of the present invention. In addition to this, it may have another wavelength conversion unit that converts light into light different from the light converted by the wavelength conversion unit. In this case, the arrangement relationship between the wavelength conversion unit using the wavelength conversion material of the present invention and another wavelength conversion unit is not particularly limited, and they may be arranged in parallel, for example. In each of the above configurations, the components are arranged in a state of being in contact with or separated from each other.

[0088] The above translucent substrate refers to a substrate that can transmit 50% or more of visible light, and specifically, it has the same meaning as the base material that the above wavelength conversion unit may have. Also, the color filter has the same meaning as the color filter that the above wavelength conversion unit may have. The shapes of the translucent substrate and the color filter are not particularly limited, and may be plate-shaped or lens-shaped.

[0089] The light-emitting device of the present invention can be used for various applications, and preferably, display devices such as various displays, lighting devices, etc. can be mentioned. The display device is not particularly limited, and examples thereof include various (liquid crystal) displays, liquid crystal backlights, liquid crystal frontlights, liquid crystal display devices such as field sequential liquid crystal displays, and further traffic signals, traffic display devices, and the like. The lighting device is not particularly limited, and examples thereof include general lighting devices (appliances), local lighting devices, interior lighting devices, and the like.

[0090] The light-emitting device of the present invention can be manufactured by a known method. For example, each component used in the above-described configuration can be sequentially laminated to be manufactured, or each component can be bonded to be manufactured. The lamination order of the components is not particularly limited.

Examples

[0091] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited thereto.

[0092] Compounds (1-1), (1-2) and (2-1) used in the examples and comparative examples, and comparative compounds (1) to (3) are shown below.

[0093]

Chemical formula

[0094] Comparative compound (1) is compound G-32 described in paragraph

[0223] of Patent Document 1. Comparative compound (2) is compound (5-A) described in JP-A-2018-146659. Comparative compound (3) is compound (2) described in International Publication No. 2018 / 117073.

[0095] Hereinafter, the synthesis methods of compounds (1-1), (1-2) and (2-1) used in each example will be described in detail, but the starting materials, intermediates and synthetic routes are not limited thereto. In the present invention, room temperature means 25°C. The abbreviations used in the synthesis of each compound shown below represent the following compounds. DIPEA: N,N-Diisopropylethylamine DBU: 1,8-Diazabicyclo[5.4.0]undec-7-ene TMSOTf: Trimethylsilyl trifluoromethanesulfonate

[0096] Unless otherwise specified, the carrier in silica gel column chromatography was SNAP KP-Sil Cartridge (manufactured by Biotage), High Flash column W001, W002, W003, W004 or W005 [manufactured by Yamazen].

[0097] The MS spectrum was measured using an ACQUITY SQD LC / MS System [manufactured by Waters, ionization method: ESI (ElectroSpray Ionization)] or LCMS-2010EV [manufactured by Shimadzu Corporation, ionization method: an ionization method that simultaneously performs ESI and APCI (Atomospheric Pressure Chemical Ionization)].

[0098] (Synthesis Example) Based on the method described in JP-A-2010-18788, the following compounds (1-1A) and (1-2A) were synthesized.

[0099]

Chemical formula

[0100] Synthesis Example 1: Synthesis of Compound (1-1)

Chemical formula

[0101] Into a 100 ml three-necked flask, 100 mg of compound (1-1A), 5 ml of toluene, and a stir bar were added, and the mixture was stirred under a nitrogen atmosphere. Then, 0.17 ml of N,N-diisopropylethylamine and 0.19 ml of boron trifluoride diethyl ether complex were added, and the mixture was stirred at 50 - 55 °C for 2 hours. After returning to room temperature, it was purified by silica gel column chromatography using hexane and ethyl acetate as eluents, and 60 mg of compound (1-1) was obtained. The obtained compound was identified by LC-MS. [M+H + + =769.5

[0102] Synthesis Example 2: Synthesis of Compound (1-2)

Chemical Structure

[0103] Into a 100 ml three-necked flask, 100 mg of compound (1-2A), 5 ml of toluene, and a stir bar were added, and the mixture was stirred under a nitrogen atmosphere. Then, 0.2 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene and 0.2 ml of boron trifluoride diethyl ether complex were added, and the mixture was stirred at 100 °C for 2 hours. After returning to room temperature, it was purified by silica gel column chromatography using hexane and ethyl acetate as eluents, and 30 mg of compound (1-2) was obtained. The obtained compound was identified by LC-MS. [M+H + + =879.6

[0104] Synthesis Example 3: Synthesis of Compound (2-1)

Chemical Structure

[0105] ​​In a 100 ml three-necked flask, 0.1 g of potassium trifluoro(trifluoromethyl)borate, 2 ml of acetonitrile, and 0.21 ml of trimethylsilyl trifluoromethanesulfonate were added, and the mixture was stirred for 30 minutes or more under a nitrogen atmosphere. On the other hand, 100 mg of compound (1-1A), 2.5 ml of dichloromethane, and 0.29 ml of N,N-diisopropylethylamine were added to a 100 ml three-necked flask, a stir bar was added, and the mixture was stirred for 10 minutes or more at room temperature under nitrogen. Then, after cooling these two solutions to 10°C or lower, they were mixed and reacted at room temperature for 10 minutes. After returning to room temperature, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with dichloromethane. The organic layer was concentrated under reduced pressure. Purification was performed by silica gel column chromatography using hexane and ethyl acetate as eluents to obtain 40 mg of compound (2-1). The obtained compound was identified by LC-MS. [M+H + + =819.5

[0106] [Evaluation 1: Fluorescence intensity of fluorescent latex] (Preparation of fluorescent latex dispersion) Fluorescent latex particles were prepared as follows. ​As the latex particles, particles with an average particle size of 150 nm were used, which were prepared by polymerizing a mixture of styrene and acrylic acid with a mass ratio of 9 to 1 in a dispersed state in water. The average particle size was measured using a Zetasizer Nano ZS (trade name, manufactured by Malvern Panalytical) based on the aforementioned measurement conditions and using the dynamic light scattering method. To 25 mL of the latex dispersion with a solid content of 2% (500 mg of solid content mass) prepared above, 5 mL of THF was added dropwise and stirred for 10 minutes. Then, 2.5 mL of a THF solution of the test compound (any one of compounds (1-1), (1-2), and (2-1) and comparative compound (1)) was added dropwise over 15 minutes. The amounts of the compounds used for each sample are summarized in Table 1. The μmol / g of the compound amount in Table 1 represents the number of moles of the compound used per 1 g of the solid content of the latex. After the dropwise addition of the test compound was completed, it was stirred for 30 minutes and then concentrated under reduced pressure to remove THF. Thereafter, after centrifugation to precipitate the particles, ultrapure water was added and redispersed to produce fluorescent latex dispersions No. 101 to 104, 201, 202, 301 to 303, and c11 to c14 with a solid content concentration of 2%. Note that the average particle sizes of the prepared fluorescent latex particles, measured in the same manner as the above latex particles, were all 150 nm.

[0107] (Evaluation of the fluorescent latex dispersion) The relative fluorescence intensity at the emission maximum wavelength of the fluorescent latex dispersion with a solid content concentration of 2 mass% produced above was evaluated. Note that a sample obtained by diluting the latex dispersion 200-fold with ultrapure water was used, and the emission maximum wavelength and the fluorescence intensity at the emission maximum wavelength were evaluated using a fluorescence spectrophotometer RF-5300PC (trade name) manufactured by Shimadzu Corporation. For each test compound, based on the fluorescence intensity at the emission maximum wavelength with a compound amount of 6 μmol / g, the fluorescence intensities at the emission maximum wavelengths of other compound amounts were evaluated as relative fluorescence intensities. The results are summarized in Table 1.

[0108]

Table 1

[0109] From the results in Table 1, it can be seen that for Compounds (1-1), (1-2) and (2-1), which are the compounds represented by the general formula (1) defined in the present invention, a fluorescent latex showing higher fluorescence intensity can be obtained as the amount of the compound increases, as compared with Comparative Compound (1). Thus, when preparing a fluorescent latex, for the compound represented by the general formula (1) defined in the present invention, as compared with the compound not represented by the general formula (1) defined in the present invention, higher fluorescence intensity can be obtained as the concentration of the compound to be blended is increased, and a fluorescent latex showing high luminance can be obtained. This is presumably based on the fact that the association of the compound in the latex particles is suppressed by the partial structure represented by formula (A) possessed by the compound represented by the general formula (1) defined in the present invention.

[0110] (Examples) Example 1 After dissolving 30 g of polystyrene (trade name: PSJ-polystyrene SGP-10, manufactured by PS Japan Corporation) in 70 g of methylene chloride, 11.6 mg of Compound (1-1) was added (the number of moles of the compound per gram of the solid content in the composition was 0.5 μmol / g) to prepare a wavelength conversion material (wavelength conversion composition (solution)). Next, this wavelength conversion composition was spin-coated on a glass plate at 2000 revolutions and dried on a hot plate at 100°C to prepare a film-like wavelength conversion material (wavelength conversion member). The thickness of the obtained wavelength conversion layer was 60 μm.

[0111] Example 2 Cellulose acylate having an acetyl substitution degree of 2.87 was prepared as follows. First, 7.8 parts by mass of sulfuric acid as a catalyst was added to 100 parts by mass of cellulose, a carboxylic acid serving as a raw material for the acyl substituent was added, and an acylation reaction was carried out at 40°C. Aging was carried out at 40°C after this acylation. Further, the low molecular weight component of this cellulose acylate was washed and removed using acetone. Next, 30 g of this cellulose acetate was dissolved in 170 g of a methylene chloride-methanol mixed solvent (mass ratio 87:13), and then 11.6 mg of compound (1-1) (the number of moles of the compound per 1 g of the solid content in the composition is 0.5 μmol / g) was added to prepare a wavelength conversion material (wavelength conversion composition (solution)). Next, this wavelength conversion composition was spin-coated on a glass plate at 2000 revolutions and dried on a hot plate at 140 °C to produce a film-like wavelength conversion material (wavelength conversion member). The thickness of the obtained wavelength conversion layer was 60 μm.

[0112] Example 3 After dissolving 30 g of polymethyl methacrylate (manufactured by Aldrich, referred to as methacrylic resin in the table) in 300 mL of toluene, 11.6 mg of compound (1-1) (the number of moles of the compound per 1 g of the solid content in the composition is 0.5 μmol / g) was added to prepare a wavelength conversion material (wavelength conversion composition (solution)). Next, this wavelength conversion composition was spin-coated on a glass plate at 2000 revolutions and dried on a hot plate at 50 °C to produce a film-like wavelength conversion material (wavelength conversion member). The thickness of the obtained wavelength conversion layer was 60 μm.

[0113] Example 4 15 g of liquid A and 15 g of liquid B of a silicone resin (trade name: KER-2500, two-component mixed addition-curing type, manufactured by Shin-Etsu Chemical Co., Ltd.) were mixed, and then 11.6 mg of compound (1-1) (the number of moles of the compound per 1 g of the solid content in the composition is 0.5 μmol / g) was added and mixed at 2000 rpm (rotation per minute) using a planetary mixer (manufactured by Shinki Co., Ltd., trade name: Awatori Rentaro), and defoamed at 2200 rpm. Thus, a wavelength conversion material (wavelength conversion composition (solution)) was prepared. Next, this wavelength conversion composition was applied on a glass plate and heated on a hot plate at 60 °C for 2 hours and further at 150 °C for 4 hours to cure it. In this way, a film-like wavelength conversion material (wavelength conversion member) was produced. The thickness of the obtained wavelength conversion layer was 60 μm.

[0114] Examples 5 and 6, Comparative Examples 1 to 3 In the preparation of the wavelength conversion composition (solution) and the production of the wavelength conversion member in Example 1, except that the compounds shown in Table 2 were used instead of the compound (1-1), wavelength conversion compositions (solutions) with a molar number of the compound per 1 g of the solid content in the composition of 0.5 μmol / g were prepared in the same manner as in Example 1, and film-like wavelength conversion members were produced, respectively. The thickness of the obtained wavelength conversion layers was 60 μm in each case.

[0115] [Evaluation 2: Evaluation of Wavelength Conversion Materials] The absorption characteristics of each compound, the quantum yield, wavelength conversion performance, and moisture and heat resistance of the produced film-like wavelength conversion members (wavelength conversion layers) were evaluated as follows. The obtained results are summarized in Table 2.

[0116] [Evaluation of Absorption Characteristics of Compounds] Using a spectrophotometer UV-3600 (trade name) manufactured by Shimadzu Corporation, the molar extinction coefficient ε (l / mol·cm) and the half-width at the maximum absorption wavelength were measured and evaluated based on the following evaluation ranks. The above half-width means the width (distance) between two wavelengths showing the intensity of half of the maximum value at the maximum absorption wavelength. In the table, the evaluation of the molar extinction coefficient ε is described in the column of ε. Note that chloroform was used as the measurement solvent. In this test, for the molar extinction coefficient, an evaluation rank of "B" or higher (S to B) is considered qualified, and for the half-width, a narrower one is preferred from the viewpoint of improving color reproducibility, and an evaluation rank of "A" or higher (S or A) is considered qualified. [Evaluation Rank of Molar Extinction Coefficient ε] S: 130,000 or more A: 120,000 or more and less than 130,000 B: 110,000 or more and less than 120,000 C: 100,000 or more and less than 110,000 D: Less than 100,000 In the above evaluation ranks, the unit of ε is l / mol·cm. [Evaluation Rank of Half-Width] S: 30 nm or less A: Above 31 nm and below 35 nm B: Above 36 nm and below 40 nm C: Above 41 nm In the above evaluation ranks, the full width at half maximum is the value obtained by rounding off the digits after the decimal point.

[0117] <Measurement of Quantum Yield> Regarding the test piece (with a glass plate) obtained by cutting the fabricated film-shaped wavelength conversion member into a square with a length of 15 mm and a width of 15 mm, the quantum yield was measured using an absolute PL quantum yield measurement device: C9920-02 (trade name, manufactured by Hamamatsu Photonics). The excitation wavelength was set to a wavelength 50 nm shorter than the maximum absorption wavelength of the compound used in each wavelength conversion member. The quantum yields of the film-shaped wavelength conversion members of Examples 1 to 6 were all 0.7 or more, which was comparable to those of the film-shaped wavelength conversion materials of Comparative Examples 1 to 3, indicating that they had a sufficient quantum yield as wavelength conversion materials.

[0118] <Evaluation of Wavelength Conversion Performance> Regarding the test piece obtained by cutting the fabricated film-shaped wavelength conversion member into a square with a length of 15 mm and a width of 15 mm, the emission spectrum was measured using a fluorescence spectrometer RF5300PC (trade name, manufactured by Shimadzu Corporation). The wavelength conversion performance was evaluated based on the following evaluation ranks for the maximum wavelength of the emission spectrum. When the maximum emission wavelength is "B" or higher in the evaluation rank, it indicates that the wavelength conversion material and the wavelength conversion member are each suitable as a wavelength conversion material or a wavelength conversion member capable of converting incident light into red light emission. - Evaluation Rank of Maximum Emission Wavelength - AA: 600 nm or more and less than 650 nm A: 580 nm or more and less than 600 nm B: 560 nm or more and less than 580 nm C: 540 nm or more and less than 560 nm D: 520 nm or more and less than 540 nm E: 480 nm or more and less than 520 nm

[0119] <Damp Heat Resistance Test> A test piece obtained by cutting the fabricated film-like wavelength conversion member into a square with a length of 40 mm and a width of 40 mm was stored in a thermo-hygrostat (product name: ESPEC CORP PR-4T, manufactured by Espec Corporation) under the following test conditions. The absorbance at the maximum absorption wavelength before and after storage was measured using a UV3150 spectrophotometer (product name, manufactured by Shimadzu Corporation). The absorbance retention rate after 7 days was calculated as the percentage of the absorbance after storage at the maximum absorption wavelength to the absorbance before storage at the maximum absorption wavelength ([absorbance after storage at the maximum absorption wavelength / absorbance before storage at the maximum absorption wavelength] × 100), and the obtained absorbance retention rate was evaluated based on the following evaluation ranks. In this test, for the damp heat resistance test, a rating of "C" or higher (A - C) is considered a pass. - Test Conditions - Storage time: 7 days Set temperature: 85°C Set humidity: 85RH% - Evaluation Ranks - A: 80% or more B: 70% or more and less than 80% C: 60% or more and less than 70% D: 50% or more and less than 60% E: Less than 50%

[0120]

Table 2

[0121] From the results in Table 2, the following can be understood. For the wavelength conversion compositions or wavelength conversion members of the comparative examples that do not contain the compound represented by the general formula (1) defined in the present invention, the molar extinction coefficients of the compounds were all small. In contrast, it can be seen that the wavelength conversion composition or wavelength conversion member containing the compound represented by the general formula (1) defined in the present invention both have a large molar extinction coefficient while maintaining a quantum yield comparable to that of the comparative example, and exhibit excellent wavelength conversion efficiency compared to the comparative example. That is, the wavelength conversion composition and wavelength conversion member of the examples, whether they are solution compositions or film-like wavelength conversion members (solid compositions) as mixtures with binder resins, improve the molar extinction coefficient significantly while maintaining the conventional quantum yield, and exhibit excellent wavelength conversion functions. Moreover, they also exhibit excellent wavelength conversion performance towards red light.

[0122] [Evaluation 3: Solubility of Compounds] [Solubility] The solubility in the following solvents or raw material monomers of the resin, namely Media A - G, was evaluated. The evaluation method was to add 0.1 ml of the solvent to 1 g (mg) of each compound to dissolve the compound, and visually determine the solubility based on the following evaluation ranks. In this test, an evaluation rank of "B" or higher is considered qualified. [Evaluation Rank] A: Completely dissolved B: Mostly dissolved C: Slightly dissolved D: Mostly insoluble

[0123] [Table 3]

[0124] [Table Note] Media A: Ethyl acetate Media B: Toluene Media C: 2-Phenoxyethyl acrylate Media D: Cyclohexyl acrylate Media E: Isobornyl acrylate Media F: Tetrahydrofurfuryl acrylate Media G: 1,6-Hexanediol diacrylate

[0125] From the results in Table 3, the following can be seen. The comparative compound (1), which is not a compound represented by the general formula (1) defined in the present invention, was inferior in solubility to the solvent or raw material monomer. On the other hand, both the compounds (1-1) and (2-1), which are compounds represented by the general formula (1) defined in the present invention, were excellent in solubility in the solvent or raw material monomer.

[0126] As a result, the compound represented by the general formula (1) defined in the present invention has a larger molar extinction coefficient and excellent solubility compared to the conventional dipyrromethene boron complex compound. The wavelength conversion material and wavelength conversion member of the present invention containing the compound represented by the general formula (1) can easily make the compound represented by the general formula (1) uniformly present at a higher concentration in the wavelength conversion material, and a high-brightness wavelength conversion material and wavelength conversion member can be obtained.

Claims

1. A compound represented by the following general formula (1A). 【Chemical 1】 In the formula, R １ to R ７ represent a hydrogen atom or a substituent. R ８ and R ９ represent an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxy group, a sulfanyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, a cyano group or a halogen atom. However, R ８ and R ９ at least one of which is an alkyl halide group, an alkyloxy halide group or a cyano group, and R １ to R ９ at least one of which has a partial structure represented by the following formula (A). 【Chemical Formula 2】 In the formula, R １１ to R １６ represents a hydrogen atom or an alkyl group, and * represents a bonding site.

2. The compound according to claim 1, wherein the compound is a compound represented by the following general formula (2A) or (3A). [Chemical Formula 3] wherein, R １ , R ３ ~R ９ , R １２ , R １４ and R １６ are synonymous with the above-mentioned R １ , R ３ ~R ９ , R １２ , R １４ and R １６ .

3. Said R ８ and R ９ The compound according to claim 1 or 2, wherein at least one of them is an alkyl halide group or a cyano group.

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