Compound, composition, optical member, color conversion member, light absorption member, and light source unit, display and lighting device comprising same
Compounds with dicarboxylic acid anhydride structures enhance color purity and durability in displays and lighting devices, addressing the dual challenges of color reproducibility and durability in conventional technologies.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- TORAY INDUSTRIES INC
- Filing Date
- 2025-11-28
- Publication Date
- 2026-07-02
Smart Images

Figure JP2025041515_02072026_PF_FP_ABST
Abstract
Description
Compounds, compositions, optical components, color conversion components, light absorbing components, and light source units, displays, and lighting devices containing the same.
[0001] The present invention relates to compounds, compositions, optical components, color conversion components, light absorbing components, and light source units, displays, and lighting devices containing the same.
[0002] There is much research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, lighting devices, and other applications. Color conversion refers to the process of converting light emitted from a light source into longer wavelength light, such as converting blue light to green or red light.
[0003] By forming this color-converting composition (hereinafter referred to as the color-converting composition) into a sheet and combining it with, for example, a blue light source, it becomes possible to obtain the three primary colors of blue, green, and red from the blue light source, i.e., to obtain white light. A white light source formed by combining such a blue light source and a color-converting sheet (hereinafter referred to as the color-converting sheet) can be used as a light source unit such as a backlight unit, and by combining this light source unit with a liquid crystal drive unit and a color filter, it becomes possible to manufacture a full-color display. Furthermore, a white light source formed by combining a blue light source and a color-converting sheet can also be used as a white light source (lighting device) such as LED lighting.
[0004] One challenge for displays such as liquid crystal displays that utilize color conversion methods is improving color reproducibility and durability. To improve color reproducibility, it is effective to narrow the full width at half maximum of the blue, green, and red emission spectra of the light source unit and increase the color purity of each of the blue, green, and red colors. As a means of solving this, for example, color conversion materials containing organic fluorescent materials have been proposed (see, for example, Patent Documents 1 and 2).
[0005] Furthermore, to improve the color reproduction accuracy of the display, it is also effective to increase the color purity of the blue, green, and red light output, which is produced by absorbing a portion of the light from the light source unit. As a means of solving this problem, light-absorbing members containing organic light-absorbing materials have been proposed (see, for example, Patent Document 3).
[0006] Japanese Patent Publication No. 2010-61824, Japanese Patent Publication No. 2014-136771, Japanese Patent Publication No. 2006-189751
[0007] Conventionally, color conversion compositions and color conversion members with excellent color reproducibility can be obtained using the technologies described in Patent Documents 1 and 2. However, from the standpoint of achieving both improved color reproducibility and improved durability, conventional color conversion compositions and color conversion members have still been insufficient.
[0008] Furthermore, a display with excellent color reproduction can be obtained using the technology described in Patent Document 3. However, conventional displays have still been insufficient in terms of achieving both improved color reproduction and improved durability.
[0009] The problem that this invention aims to solve is to provide a compound suitable as an optical material used in light source units, displays, or lighting devices, and to achieve both improved color reproducibility and improved durability in compositions, optical components, color conversion components, or light absorbing components using this compound. In particular, this invention aims to provide a compound, composition, optical component, color conversion component, or light absorbing component that achieves both high color purity emission and light absorption and high durability.
[0010] To solve the above-mentioned problems and achieve the objective, the present invention has a configuration described in any one of the following [1] to
[25] .
[0011] In other words, the compound according to the present invention is characterized by being represented by the following general formula (1).
[0012] (In the above general formula (1), R 1 ~R 9may be the same or different, and is selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxy group, an oxycarbonyl group, an ester group, a carbamoyl group, an amide group, a sulfonyl group, a sulfonic acid ester group, a sulfonamide group, an amino group, an imino group, a nitro group, a silyl group, a siloxanyl group, a boryl group, and a phosphine oxide group. These Rs 1 ~R 9 may form a ring structure by linking adjacent groups to each other. However, among these Rs 1 ~R 9 at least one of R 1 ~R 7 is a group containing a dicarboxylic acid anhydride structure.)
[0013] Further, the compound according to the present invention is [2] in the invention described in [1] above, in the general formula (1), at least R 2 , R 5 and R 7 wherein any one of them is a group containing a dicarboxylic acid anhydride structure.
[0014] Further, the compound according to the present invention is [3] in the invention described in [1] or [2] above, in the general formula (1), at least R 7 is a group containing a dicarboxylic acid anhydride structure.
[0015] Further, the compound according to the present invention is [4] in the invention described in any one of [1] to [3] above, wherein the dicarboxylic acid anhydride structure is any one or more of a phthalic anhydride structure, a 1,2 - cyclohexanedicarboxylic acid anhydride structure, a succinic anhydride structure, and a maleic anhydride structure.
[0016] Further, the compound according to the present invention is [5] in the invention described in [1] above, wherein the group containing a dicarboxylic acid anhydride structure is a group represented by the following general formula (2).
[0017] (In the above general formula (2), L is a linking group composed of a combination of 1 to 5 groups selected from the group consisting of single bonds, alkylene groups, cycloalkylene groups, heterocyclic groups, alkenylene groups, cycloalkenylene groups, alkylylene groups, arylene groups, heteroarylene groups, ether bonds, thioether bonds, carbonyl groups, ester bonds, amide bonds, sulfonyl groups, sulfonic acid ester bonds, sulfonamide bonds, amino groups, imino groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups.)
[0018] Furthermore, the compounds according to the present invention are characterized in that, in the invention described in [5] above, L in the general formula (2) is a linking group composed of a combination of 1 to 5 elements selected from the group consisting of single bonds, arylene groups, carbonyl groups, ester bonds, and amide bonds.
[0019] Furthermore, the compounds according to the present invention are, in the invention described in [1] above, R in the general formula (1) 7 However, it is characterized by being a group represented by the following general formula (3).
[0020]
[0021] Furthermore, the compounds according to the present invention are, in the invention described in [1] above, R in the general formula (1) 1 ~R 6 The present invention is characterized in that at least one of the members is an ester group.
[0022] Furthermore, the compounds according to the present invention are, in the invention described in [1] above, R in the general formula (1) 1 ~R 6 The present invention is characterized in that at least one of the groups is an aryl group.
[0023] Furthermore, the compounds according to the present invention are, in the invention described in [1] above, R in the general formula (1) 1 ~R 6 A key feature is that at least one of them is an alkyl group.
[0024] Furthermore, the compounds according to the present invention
[11] in the invention described in [1] above, R in the general formula (1) 1 ~R 6 The present invention is characterized in that at least one of the groups is a group containing a fluorine atom.
[0025] Furthermore, the compounds according to the present invention are, in the invention described in [1] above, R in the general formula (1) 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 The characteristic feature is that at least one of the four sets of structures is a ring structure represented by one of the following general formulas (4A) to (4D).
[0026] (In the general formulas (4A) to (4D), R 101 , R 102 and R 201 ~R 204 Each of these may be the same or different, and is selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, ester group, carbamoyl group, amide group, sulfonyl group, sulfonic acid ester group, sulfonamide group, amino group, imino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocyclic ring. In addition, in each of the ring structures represented by the general formulas (4A) to (4D) above, R 101 and R 102 The rings may be formed. The "*" in the general formulas (4A) to (4D) indicates the connection to the pyromethene skeleton.
[0027] Furthermore, the composition according to the present invention is characterized by comprising
[13] a compound described in any one of [1] to
[12] above and a binder resin.
[0028] Furthermore, the optical member according to the present invention is characterized by comprising the composition described in
[13] above or a cured product thereof.
[0029] Furthermore, the color-converting member according to the present invention is characterized by comprising the composition described in
[13] above or a cured product thereof.
[0030] Furthermore, the light-absorbing member according to the present invention is characterized by comprising the composition described in
[13] above or a cured product thereof.
[0031] Furthermore, the light source unit according to the present invention is characterized by comprising
[17] a light source and the optical member described in
[14] above.
[0032] Furthermore, the light source unit according to the present invention is characterized by comprising
[18] a light source and the color conversion member described in
[15] above.
[0033] Furthermore, the light source unit according to the present invention is characterized by comprising
[19] a light source and the light absorbing member described in
[16] above.
[0034] Furthermore, the display according to the present invention is characterized by comprising
[20] a light source and the optical member described in
[14] above.
[0035] Furthermore, the display according to the present invention is characterized by comprising
[21] a light source and the color conversion member described in
[15] above.
[0036] Furthermore, the display according to the present invention is characterized by comprising
[22] a light source and the light absorbing member described in
[16] above.
[0037] Furthermore, the lighting device according to the present invention is characterized by comprising
[23] a light source and the optical member described in
[14] above.
[0038] Furthermore, the lighting device according to the present invention is characterized by comprising
[24] a light source and the color conversion member described in
[15] above.
[0039] Furthermore, the lighting device according to the present invention is characterized by comprising
[25] a light source and the light absorbing member described in
[16] above.
[0040] The compound, composition using the same, optical component, color conversion component, and light absorbing component according to the present invention achieve both high color purity and high durability, thereby enabling improved color reproducibility and improved durability simultaneously.
[0041] Figure 1 is a schematic cross-sectional view showing a first example of an optical member according to an embodiment of the present invention. Figure 2 is a schematic cross-sectional view showing a second example of an optical member according to an embodiment of the present invention. Figure 3 is a schematic cross-sectional view showing a third example of an optical member according to an embodiment of the present invention. Figure 4 is a schematic cross-sectional view showing a fourth example of an optical member according to an embodiment of the present invention. Figure 5 is a schematic cross-sectional view showing a fifth example of an optical member according to an embodiment of the present invention. Figure 6 is a schematic cross-sectional view showing a sixth example of an optical member according to an embodiment of the present invention.
[0042] The following describes preferred embodiments of the compounds, compositions, optical members, color conversion members, light absorbing members, and light source units, displays, and lighting devices containing them according to the present invention. However, the present invention is not limited to the following embodiments and can be modified in various ways depending on the purpose and application. Furthermore, matters listed as preferred examples in a particular embodiment can also be applied to other embodiments.
[0043] <Compounds> The compounds according to the embodiments of the present invention (hereinafter sometimes abbreviated as "compounds of the present invention") are organic light-emitting materials or organic light-absorbing materials. In the present invention, a light-emitting material is a material that emits light of a different wavelength from the light when irradiated with some light. An organic light-emitting material is a light-emitting material composed of organic compounds. In the present invention, a light-absorbing material is a material that absorbs at least a portion of the light when irradiated with some light. An organic light-absorbing material is a light-absorbing material composed of organic compounds. The organic light-absorbing material may also have the function of an organic light-emitting material. In detail, the compounds of the present invention are compounds represented by the following general formula (1).
[0044]
[0045] In general formula (1), R 1 ~R 9 These R groups may be the same or different, and are selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, ester group, carbamoyl group, amide group, sulfonyl group, sulfonic acid ester group, sulfonamide group, amino group, imino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. 1 ~R 9 The groups may be adjacent to each other and form a ring structure. However, these R 1 ~R 9 R in 1 ~R 7 At least one of these groups is a group containing a dicarboxylic acid anhydride structure.
[0046] In all of the above groups, hydrogen may be replaced with deuterium. This is also true for the compounds or substructures described below. Furthermore, in the following descriptions, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms refers to an aryl group whose total carbon number, including the carbon atoms in the substituents substituted on the aryl group, is 6 to 40. The same applies to other substituents that specify the number of carbon atoms.
[0047] In the phrase "substituted or unsubstituted," "unsubstituted" means that a hydrogen atom or a deuterium atom has been substituted. The same applies to the phrase "substituted or unsubstituted" in the compounds or substructures described below.
[0048] Furthermore, for all of the above groups, examples of substituents that may be substituted include alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, halogens, cyano groups, aldehyde groups, carbonyl groups, carboxyl groups, oxycarbonyl groups, ester groups, carbamoyl groups, amide groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, imino groups, amino groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, or phosphine oxide groups. These substituents may also be further substituted with the substituents mentioned above.
[0049] Alkyl groups refer to saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups, and may or may not have substituents. There are no particular restrictions on additional substituents when substitution occurs; for example, alkyl groups, halogens, aryl groups, heteroaryl groups, etc., can be used, and this point is also common to the following description. Furthermore, the number of carbon atoms in the alkyl group is not particularly limited, but from the standpoint of availability and cost, it is preferably in the range of 1 to 20, more preferably 1 to 8.
[0050] A cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as a cyclopropyl group, cyclohexyl group, norbornyl group, or adamantyl group, and may or may not have substituents. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably in the range of 3 to 20.
[0051] A heterocyclic group refers to an aliphatic ring having atoms other than carbon within the ring, such as a pyran ring, a piperidine ring, or a cyclic amide, and may or may not have substituents. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 to 20.
[0052] An alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, which may or may not have substituents. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 to 20.
[0053] A cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, cyclopentadienyl group, or cyclohexenyl group, which may or may not have substituents. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 to 20.
[0054] An alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and may or may not have substituents. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 to 20.
[0055] An alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether linkage, such as a methoxy group, ethoxy group, or propoxy group. This aliphatic hydrocarbon group may or may not have substituents. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.
[0056] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced by a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have substituents. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.
[0057] An aryl ether group refers to a functional group in which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have substituents. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 to 40.
[0058] An arylthioether group is an aryl ether group in which the oxygen atom in the ether bond is replaced by a sulfur atom. The aromatic hydrocarbon group in the arylthioether group may or may not have substituents. The number of carbon atoms in the arylthioether group is not particularly limited, but is preferably in the range of 6 to 40.
[0059] The aryl group refers to aromatic hydrocarbon groups such as phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, benzophenanthryl, benzoanthracenyl, chrysenyl, pyrenyl, fluoranthenyl, triphenylenyl, benzofluoranthenyl, dibenzoanthracenyl, perilenyl, and hericenyl groups. Among these, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, and triphenylenyl groups are preferred. The aryl group may or may not have substituents. The number of carbon atoms in the aryl group is not particularly limited, but is preferably in the range of 6 to 40, more preferably 6 to 30.
[0060] Furthermore, as the aryl group, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, and anthracenyl groups are preferred, and phenyl, biphenyl, terphenyl, and naphthyl groups are more preferred. Even more preferred are phenyl, biphenyl, and terphenyl groups, with phenyl being particularly preferred.
[0061] When each substituent is further substituted with an aryl group, the aryl group is preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, or anthracenyl group, and more preferably a phenyl group, biphenyl group, terphenyl group, or naphthyl group. Particularly preferred is a phenyl group.
[0062] Heteroaryl groups include, for example, pyridyl, furanyl, thienyl, quinolinyl, isoquinolinyl, pyrazinyl, pyrimidyl, pyridadinyl, triazinyl, naphthilidinyl, synnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and benzocarbazolyl groups. This refers to cyclic aromatic groups having one or more non-carbon atoms in the ring, such as a 1,5-naphthilidinyl group, a 1,6-naphthilidinyl group, a 1,7-naphthilidinyl group, a 1,8-naphthilidinyl group, a 2,6-naphthilidinyl group, or a 2,7-naphthilidinyl group. The heteroaryl group may or may not have substituents. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 40, more preferably 2 to 30.
[0063] Furthermore, preferred heteroaryl groups include pyridyl, furanyl, thienyl, quinolinyl, pyrimidyl, triazinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, and phenanthrolinyl groups, with pyridyl, furanyl, thienyl, and quinolinyl groups being more preferred. Particularly preferred is the pyridyl group.
[0064] When each substituent is further substituted with a heteroaryl group, the heteroaryl group is preferably a pyridyl group, furanyl group, thienyl group, quinolinyl group, pyrimidyl group, triazinyl group, benzofuranyl group, benzothienyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, or phenanthrolinyl group, and more preferably a pyridyl group, furanyl group, thienyl group, or quinolinyl group. Particularly preferred is a pyridyl group.
[0065] A halogen refers to an atom selected from fluorine, chlorine, bromine, and iodine. Furthermore, carbonyl groups, carboxyl groups, oxycarbonyl groups, ester groups, carbamoyl groups, amide groups, and imino groups may or may not have substituents. Examples of substituents include alkyl groups, cycloalkyl groups, aryl groups, and heteroaryl groups, and these substituents may be further substituted.
[0066] Sulfonyl group, sulfonic acid ester group, and sulfonamide group are, respectively, -S(=O)2R 10 , -S(=O)2OR 10 , -S(=O)2NR 10 R 11 These are groups represented by R. 10 and R 11 Each of these is selected from the same group as hydrogen atoms or substituents in the case of substitution described above.
[0067] An amino group is a substituted or unsubstituted amino group. Examples of substituents include aryl groups, heteroaryl groups, linear alkyl groups, and branched alkyl groups. Preferred aryl and heteroaryl groups are phenyl, naphthyl, pyridyl, and quinolinyl groups. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably 6 to 40, and most preferably 6 to 30.
[0068] The silyl group refers to alkylsilyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, and vinyldimethylsilyl, as well as arylsilyl groups such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl. The substituents on silicon may be further substituted. The number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.
[0069] A siloxanyl group refers to a silicon compound group via an ether bond, such as a trimethylsiloxanyl group. The substituent on the silicon may be further substituted. A boryl group refers to a substituted or unsubstituted boryl group. Examples of substituents include aryl groups, heteroaryl groups, linear alkyl groups, branched alkyl groups, aryl ether groups, alkoxy groups, and hydroxyl groups. Among these, aryl groups and aryl ether groups are preferred.
[0070] A phosphine oxide group is -P(=O)R 10 R 11 This is the group represented by . The R of the phosphine oxide group 10 and R 11 Each of these is selected from the same group as hydrogen atoms or substituents in the case of substitution described above.
[0071] Furthermore, in a compound represented by general formula (1), any two adjacent substituents (for example, R of general formula (1)) 2 and R 3 These rings may be linked to each other to form a conjugated or non-conjugated ring structure. In addition to carbon, the constituent elements of this ring structure may include elements selected from nitrogen, oxygen, sulfur, phosphorus, and silicon. Furthermore, this ring structure may be fused with another ring.
[0072] Compounds represented by general formula (1) exhibit high fluorescence quantum yield and have a small full width at half maximum of the emission spectrum at the peak emission wavelength, thus achieving both efficient color conversion and high color purity.
[0073] Furthermore, compounds represented by general formula (1) have a large molar extinction coefficient and a small full width at half maximum of the absorption spectrum at the peak wavelength of light absorption, thus enabling both efficient light absorption and high color purity.
[0074] Furthermore, by introducing appropriate substituents at appropriate positions, various properties and physical characteristics of compounds represented by general formula (1) can be adjusted, such as emission peak wavelength, luminous efficiency, absorption peak wavelength, extinction coefficient, color purity, thermal stability, photostability, and dispersibility.
[0075] One cause of photodegradation of organic light-emitting and organic light-absorbing materials is oxidative degradation of the material due to oxygen, particularly singlet oxygen generated by dye sensitization mechanisms. To improve the durability of organic light-emitting and organic light-absorbing materials, it is crucial to develop materials that exhibit high stability against oxygen.
[0076] Compounds represented by general formula (1) are those in general formula (1) where R 1 ~R 7 Because at least one of the groups contains a dicarboxylic acid anhydride structure, the electron density of the central skeleton of the compound is reduced, resulting in high stability against oxygen. As a result, the durability of the compound can be further improved.
[0077] From the viewpoint of enhancing the above-mentioned effect of improving stability against oxygen, in general formula (1), at least R 2 , R 5 and R 7 Preferably, one of these groups contains a dicarboxylic acid anhydride structure. In particular, in general formula (1), at least R 7 It is more preferable that the group contains a dicarboxylic acid anhydride structure.
[0078] In the present invention, the dicarboxylic acid anhydride structure is a structure in which two carboxyl groups undergo dehydration condensation to form a cyclic structure. The dicarboxylic acid anhydride structure in the compound represented by general formula (1) is not particularly limited, but it is preferably one or more of the following, for example, a phthalic anhydride structure, a 1,2-cyclohexanedicarboxylic acid anhydride structure, a succinic anhydride structure, and a maleic anhydride structure. In the present invention, R in general formula (1) 1 ~R 7 R 7 It is more preferable that at least one of the groups is a group containing a dicarboxylic acid anhydride structure, and it is particularly preferable that the dicarboxylic acid anhydride structure is one or more of the phthalic acid anhydride structure, the 1,2-cyclohexanedicarboxylic acid anhydride structure, the succinic acid anhydride structure, and the maleic acid anhydride structure.
[0079] One preferred example of a compound represented by general formula (1) is a group containing a dicarboxylic acid anhydride structure, which is represented by the following general formula (2).
[0080]
[0081] In general formula (2), L is a linking group composed of a combination of 1 to 5 groups selected from the group consisting of single bonds, alkylene groups, cycloalkylene groups, heterocyclic groups, alkenylene groups, cycloalkenylene groups, alkylylene groups, arylene groups, heteroarylene groups, ether bonds, thioether bonds, carbonyl groups, ester bonds, amide bonds, sulfonyl groups, sulfonic acid ester bonds, sulfonamide bonds, amino groups, imino groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups.
[0082] In general formula (2), it is more preferable that L is a linking group composed of 1 to 5 elements selected from the group consisting of single bonds, arylene groups, carbonyl groups, ester bonds, and amide bonds, as this allows the conjugated system to spread smoothly and enhances the effect of reducing the electron density of the central skeleton by the dicarboxylic acid anhydride structure. In particular, it is even more preferable that L is a linking group composed of 1 to 3 elements selected from the group consisting of single bonds, arylene groups, and ester bonds.
[0083] Another preferred example of a compound represented by general formula (1) is R in general formula (1). 7 One characteristic is that the group is represented by the following general formula (3). In this case, the effect of reducing the electron density of the central skeleton of the compound represented by general formula (1) is strengthened, which is particularly preferable.
[0084]
[0085] A preferred embodiment of the compound represented by general formula (1) is R in general formula (1). 1 ~R 6 One example is that at least one of them is an ester group. In this case, the electron density of the central skeleton of the compound represented by general formula (1) is further reduced, and the durability of the compound can be further improved. In particular, R in general formula (1) 2 ~R 5 It is more preferable that at least one of them is an ester group, and R in general formula (1) 2 and R 5 It is even more preferable that at least one of these R is an ester group, 2 and R 5 It is particularly preferable that both are ester groups. Furthermore, it is preferable that the ester group contains a fluorine atom, more preferably an aryl group containing a fluorine atom, and particularly preferable an aryl group substituted with an alkyl fluoride group. It is also preferable that the ester group contains a dicarboxylic acid anhydride structure.
[0086] A preferred embodiment of the compound represented by general formula (1) is R in general formula (1). 1 ~R6 At least one of them is an aryl group. In this case, the rigidity of the central skeleton of the compound represented by the general formula (1) is increased, and the durability of the compound can be further improved. Among them, R in the general formula (1) 1 , R 3 , R 4 and R 6 It is more preferable that at least one of them is an aryl group, and it is even more preferable to satisfy at least one of the following conditions (i) and (ii). Condition (i) is the condition that both R 1 and R 3 are aryl groups. Condition (ii) is the condition that both R 4 and R 6 are aryl groups. Also, it is particularly preferable that all of R 1 , R 3 , R 4 and R 6 are aryl groups.
[0087] Among R 1 to R 6 in the general formula (1), when at least one of them is an aryl group, the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, and among them, a phenyl group is particularly preferable. These groups may be further substituted. Also, when the aryl group contains a fluorine atom, it is preferable because the electron density of the central skeleton of the compound represented by the general formula (1) is reduced. It is more preferable that the aryl group is substituted with at least one of fluorine, an alkyl fluoride group, and an aryl group containing a fluorine atom. It is particularly preferable that the aryl group is substituted with at least one of fluorine and an alkyl fluoride group. It is also preferable that the aryl group contains a dicarboxylic anhydride structure.
[0088] As another preferable embodiment of the compound represented by the general formula (1), R 1 to R 6at least one of which is an alkyl group. In this case, in the central skeleton of the compound represented by the general formula (1), the reactivity of the highly reactive site can be reduced, and the durability of the compound can be further improved. Among them, R in the general formula (1) 1 , R 3 , R 4 and R 6 it is more preferable that at least one of them is an alkyl group, and it is even more preferable to satisfy at least one of the following conditions (i) and (ii). Condition (i) is the condition that both of the above R 1 and R 3 are alkyl groups. Condition (ii) is the condition that both of the above R 4 and R 6 are alkyl groups. Further, it is particularly preferable that all of the above R 1 , R 3 , R 4 and R 6 are alkyl groups.
[0089] 3 The condition is that at least one of them is a group containing a fluorine atom. Condition (ii-1) is the above R 2 and R 5 The condition is that at least one of the groups contains a fluorine atom. Condition (iii) is the above R 3 and R 6 The condition is that at least one of the groups contains a fluorine atom. Furthermore, it is more preferable that at least one of the following conditions (i), (iii-2), and (iii) is satisfied. Conditions (i) and (iii) are as described above. Condition (iii-2) is the above R 2 and R 5 The condition is that both groups contain a fluorine atom. It is also preferable that the fluorine atom-containing group includes a dicarboxylic acid anhydride structure.
[0091] Another preferred embodiment of the compound represented by general formula (1) is R in general formula (1). 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 One of the four sets of structures is a ring structure represented by one of the following general formulas (4A) to (4D). Each of the ring structures represented by general formulas (4A) to (4D) has a double bond. Therefore, by introducing one of these ring structures into the compound, the conjugation can be extended and the emission can be made to a longer wavelength. Furthermore, since the double bond site can be chemically bonded to the central skeleton by the ring structure introduced into the compound, excessive structural relaxation in the excited state can be suppressed, and emission with good color purity can be obtained.
[0092]
[0093] In general formulas (4A) to (4D), R 101 , R 102 and R 201 ~R 204Each of these may be the same or different, and is selected from the group consisting of hydrogen atoms, alkyl groups, cycloalkyl groups, heterocyclic groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, hydroxyl groups, thiol groups, alkoxy groups, alkylthio groups, aryl ether groups, arylthioether groups, halogens, cyano groups, aldehyde groups, carbonyl groups, carboxyl groups, oxycarbonyl groups, ester groups, carbamoyl groups, amide groups, sulfonyl groups, sulfonic acid ester groups, sulfonamide groups, amino groups, imino groups, nitro groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocyclic ring. In addition, in each ring structure represented by general formulas (4A) to (4D), R 101 and R 102 The rings may be formed. The asterisk (*) in general formulas (4A) to (4D) indicates the connection with the pyromethene skeleton.
[0094] For example, in a compound represented by general formula (1), R 1 and R 2 , and R 2 and R 3 One of the two sets of structures is a ring structure of one of the general formulas (4A) to (4D), R 4 , R 5 and R 6 The structure is preferably not a ring structure between adjacent groups. In particular, R 2 and R 3 It is more preferable that the structure is a ring structure represented by the general formula (4D).
[0095] Furthermore, as another example of a compound represented by general formula (1), R 1 and R 2 , and R 2 and R 3 One of the two sets of structures is a ring structure of one of the general formulas (4A) to (4D), R 4 and R 5 , and R 5 and R 6 It is preferable that one of the two sets of structures be a ring structure of any of the general formulas (4A) to (4D). In particular, R 2and R 3 , and R 5 and R 6 It is more preferable that both of the two sets of structures are ring structures of general formula (4D).
[0096] In the ring structure represented by general formula (4D), Ar is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, or a substituted or unsubstituted pyrazine ring. Furthermore, since thermal and photochemical stability is improved when Ar is a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzene ring is preferred as Ar in general formula (4D).
[0097] In general formulas (4A) to (4D), R 101 and R 102 It is preferable that R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, because this allows the compound represented by general formula (1) to exhibit better thermal and photostability. In particular, R 101 and R 102 When R is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, the fluorescence quantum yield is high, therefore these R 101 and R 102 Preferred substituents are substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups. Specific examples of these preferred substituents include methyl, ethyl, isopropyl, and tert-butyl groups as alkyl groups, and phenyl groups as aryl groups. Among these, methyl and phenyl groups are particularly preferred from the viewpoint of ease of synthesis and dispersibility. When these groups are the substituents, quenching due to aggregation of molecules is suppressed.
[0098] Furthermore, in general formulas (4A) to (4D), R 101 and R 102 The two may form a ring. 101 and R 102The formation of a ring suppresses structural relaxation, resulting in sharper luminescence. Furthermore, the suppression of thermal vibrations throughout the molecule improves thermal stability. 101 and R 102 A preferred example of a case where and form a ring is when they form a spirofluorene ring. Specifically, R 101 and R 102 Both are benzene rings, and they form a ring structure.
[0099] Another preferred embodiment of the compound represented by general formula (1) is R in general formula (1). 7 It is preferable that the group is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. In particular, it is preferable that the decrease in photostability due to excessive twisting of the carbon-carbon bond is suppressed. 7 It is preferable that this is a substituted or unsubstituted phenyl group.
[0100] Furthermore, R in general formula (1) 7 If R is a group represented by the following general formula (5), 7 By making it moderately bulky, the decrease in fluorescence quantum yield due to concentration quenching, etc., can be suppressed. Also, R 7 This can reduce the reactivity around the carbon atom to which it is bonded, thereby improving photostability. Therefore, R 7 The structure is preferably represented by general formula (5).
[0101]
[0102] In general formula (5), r is selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, ester group, carbamoyl group, amide group, amino group, imino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. k is an integer from 1 to 3. If k is 2 or greater, r may be the same or different.
[0103] From the viewpoint of achieving a moderately bulky structure and further suppressing the decrease in fluorescence quantum yield, r in general formula (5) is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group. Among these aryl groups, phenyl groups and naphthyl groups are particularly preferred. When these aryl groups are substituted, substituents include alkyl groups, heterocyclic groups, alkenyl groups, hydroxyl groups, alkoxy groups, aryl ether groups, aryl groups, heteroaryl groups, halogens, cyano groups, carboxyl groups, and ester groups. These groups may be further substituted. When r in general formula (5) is an aryl group, k in general formula (5) is preferably 1 or 2, and more preferably 2.
[0104] Furthermore, from the viewpoint of controlling fluorescence and absorption wavelengths and improving compatibility with solvents, it is preferable that r in general formula (5) be a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen. Among these, from the viewpoint of dispersibility, a tert-butyl group and a methoxy group are particularly preferred as r.
[0105] In general formula (1), R 8 and R 9The group is preferably fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, a fluorine-containing alkoxy group, a fluorine-containing aryloxy group, a fluorine-containing heteroaryloxy group, or a cyano group. In particular, R is preferred because it is stable to excitation light and yields a higher fluorescence quantum yield. 8 and R 9 It is more preferable that the group be a fluorine or cyano group.
[0106] Furthermore, from the viewpoint of suppressing aggregation of materials due to thermal diffusion, etc., and the resulting decrease in quantum yield, in general formula (1), R 1 ~R 7 At least one of them is preferably a moderately bulky substituent. In particular, R 2 , R 5 , R 7 It is more preferable that at least one of the substituents is moderately bulky, R 2 , R 5 , R 7 It is particularly preferable that all of these substituents are moderately bulky.
[0107] R 2 and R 5 Examples of moderately bulky substituents include substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted ester groups. Of the above bulky substituents, substituted or unsubstituted ester groups are more preferred, substituted or unsubstituted aryl ester groups are even more preferred, and substituted or unsubstituted phenyl ester groups are particularly preferred. Among these, phenyl ester groups substituted with aryl groups are particularly suitable as the above bulky substituents.
[0108] R 7 Examples of moderately bulky substituents include substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. Among these, substituted or unsubstituted phenyl groups are more preferred, and the group represented by the above general formula (5) is particularly preferred.
[0109] Furthermore, another preferred embodiment of the compound represented by general formula (1) is R 1 ~R7 It is preferable that at least one of them is an electron-withdrawing group. In particular, (1) R 1 ~R 6 (2) R 7 (3) R 1 ~R 6 At least one of them is an electron-withdrawing group, and R 7 It is preferable that the group is an electron-withdrawing group. By introducing an electron-withdrawing group into a compound represented by general formula (1), the electron density of the central skeleton of the compound can be significantly reduced. As a result, the stability of the compound against oxygen is further improved, and consequently, the durability of the compound can be further improved.
[0110] Electron-withdrawing groups, also called electron-accepting groups, are groups of atoms that attract electrons from substituted atomic groups through inductive or resonance effects in organic electron theory. Examples of electron-withdrawing groups include those whose substituent constant (σp (para)) in Hammett's rule takes a positive value. The substituent constant (σp (para)) in Hammett's rule can be quoted from the Chemical Handbook Basic Edition, 5th Revised Edition (II-380). Although phenyl groups also sometimes take a positive value as described above, phenyl groups are not included as electron-withdrawing groups in this invention.
[0111] Examples of electron-withdrawing groups include -F (σp: +0.20), -Cl (σp: +0.28), -Br (σp: +0.30), -I (σp: +0.30), and -CO2R. 12 (σp:R 12 When it is an ethyl group, +0.45), -CONH2 (σp: +0.38), -COR 12 (σp:R 12 When it is a methyl group, +0.49), -CF3 (σp: +0.51), -SO2R 12 (σp:R 12 Examples include when it is a methyl group (+0.69), -NO2 (σp: +0.81), etc. 12Each of these independently represents a hydrogen atom, a substituted or unsubstituted ring-forming aromatic hydrocarbon group with 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group with 1 to 30 carbon atoms. Specific examples of each of these groups are the same as those given above.
[0112] Preferred electron-withdrawing groups include fluorine, fluorinated aryl groups, fluorinated heteroaryl groups, fluorinated alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups, substituted or unsubstituted amide groups, substituted or unsubstituted sulfonyl groups, or cyano groups. This is because these groups are difficult to decompose chemically.
[0113] More preferred electron-withdrawing groups include fluorine-containing alkyl groups, substituted or unsubstituted acyl groups, substituted or unsubstituted ester groups, or cyano groups. This is because they prevent concentration quenching and improve the emission quantum yield. Particularly preferred electron-withdrawing groups are substituted or unsubstituted ester groups.
[0114] One preferred example of a compound represented by general formula (1) is R 1 , R 3 , R 4 and R 6 All of them may be the same or different, and are substituted or unsubstituted phenyl groups, and furthermore, R 7 One example is when the group is represented by general formula (2). In this case, R 7 It is more preferable that the group is represented by general formula (3). Also, R 1 , R 3 , R 4 and R 6 It is more preferable that at least one of these is substituted with at least one group selected from fluorine, alkyl fluoride, and aryl groups containing a fluorine atom.
[0115] Another preferred example of a compound represented by general formula (1) is R 1 , R 3 , R 4 and R6 All of them may be the same or different, and are substituted or unsubstituted alkyl groups, and further, R 7 One example is when the group is represented by general formula (2). In this case, R 7 It is more preferable that the group is represented by general formula (3). Also, R 2 and R 5 These may be the same or different, more preferably substituted or unsubstituted ester groups, and even more preferably substituted or unsubstituted aryl ester groups.
[0116] As yet another preferred example of a compound represented by general formula (1), R 1 , R 3 , R 4 and R 6 All of them may be the same or different, and are substituted or unsubstituted alkyl groups, and further, R 2 and R 5 One example is when the group is represented by general formula (2). In this case, R 7 It is more preferable that the group is represented by general formula (2) or general formula (5).
[0117] As yet another preferred example of a compound represented by general formula (1), R 2 and R 3 The structure is a ring structure represented by the general formula (4D), where Ar in the general formula (4D) is a substituted or unsubstituted benzene ring, and R in the general formula (4D) 101 and R 102 and may be the same or different, and are substituted or unsubstituted alkyl groups or substituted or unsubstituted phenyl groups, and R in general formula (1) 7 One example is when the group is represented by general formula (2). In this case, R 4 and R 6 These may be the same or different, and are more preferably substituted or unsubstituted phenyl groups. Among them, R 4 and R 6It is more preferable that at least one of these is a phenyl group substituted with at least one group selected from fluorine, alkyl fluoride, and aryl groups containing a fluorine atom. Also, R in general formula (4D) 101 and R 102 It is also preferable that the two elements form a ring.
[0118] As yet another preferred example of a compound represented by general formula (1), R 2 and R 3 The structure is a ring structure represented by the general formula (4D), where Ar in the general formula (4D) is a substituted or unsubstituted benzene ring, and R in the general formula (4D) 101 and R 102 and may be the same or different, and are substituted or unsubstituted alkyl groups or substituted or unsubstituted phenyl groups, and R in general formula (1) 4 , R 5 and R 6 One example is when at least one of them is a group represented by general formula (2). In this case, R 7 It is more preferable that the group is represented by general formula (2) or general formula (5). Also, the R in general formula (4D) 101 and R 102 It is also preferable that the two elements form a ring.
[0119] An example of the structure of a compound represented by general formula (1) is shown below, but the compound is not limited to this example. In particular, the fluorine (F) bonded to the boron atom (B) in the structure of the compound may be a cyano group (CN).
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126] Each of the compounds exemplified above may be a compound in which some of the hydrogen atoms in its structure are substituted with deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a fluorine atom. In particular, each of the above compounds may be a compound in which the said some of the hydrogen atoms are substituted with a fluorinated alkyl group, a fluorinated phenyl group, or a fluorine atom.
[0127] <Composition> The composition according to the embodiment of the present invention (hereinafter sometimes abbreviated as "the composition of the present invention") comprises at least a compound represented by general formula (1) and a binder resin. The compound represented by general formula (1) (the compound of the present invention) is an organic light-emitting material or an organic light-absorbing material, as described above. The light-emitting material, light-absorbing material, and binder resin contained in the composition of the present invention will be described in order below.
[0128] One embodiment of the composition of the present invention is a color conversion composition. In the present invention, a color conversion composition is a composition that emits light of a different wavelength from the light when irradiated with some light.
[0129] The composition of the present invention preferably contains the following luminescent material (a) as a luminescent material, such as an organic luminescent material which is a compound represented by general formula (1). The luminescent material (a) is a luminescent material that exhibits emission observed in the region of peak wavelength between 500 nm and 580 nm when excitation light in the wavelength range of 400 nm to 500 nm is used. Hereafter, emission observed in the region of peak wavelength between 500 nm and 580 nm will be referred to as "green emission" as needed.
[0130] Furthermore, it is preferable that the composition of the present invention contains the above-described luminescent material (a) and the following luminescent material (b). As described above, luminescent material (a) is a luminescent material that exhibits emission with a peak wavelength of 500 nm to less than 580 nm when excitation light with a wavelength in the range of 400 nm to 500 nm is used. Luminescent material (b) is a luminescent material that exhibits emission observed in the region of 580 nm to 750 nm when excited by excitation light with a wavelength in the range of 400 nm to 500 nm and emission from luminescent material (a). Hereafter, emission observed in the region of 580 nm to 750 nm will be referred to as "red emission" as needed.
[0131] Since a portion of the excitation light in the wavelength range of 400 nm to 500 nm is partially transmitted through the composition or optical component of the present invention (a component containing the composition or a cured product thereof), when a blue LED with a sharp emission peak is used, it exhibits a sharp emission spectrum in blue, green, and red, and white light with good color purity can be obtained. As a result, especially in displays, a wider color gamut with more vivid colors can be efficiently created. Furthermore, in lighting applications, compared to white LEDs that combine blue LEDs and yellow phosphors, which are currently mainstream, the emission characteristics in the green and red regions are improved, resulting in a desirable white light source with improved color rendering.
[0132] Examples of luminescent materials (a) include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153; cyanine derivatives such as indocyanine green; fluorescein derivatives such as fluorescein, fluorescein isothiocyanate, and carboxyfluorescein diacetate; phthalocyanine derivatives such as phthalocyanine green; perylene derivatives such as diisobutyl-4,10-dicyanoperylene-3,9-dicarboxylate; pyromethene derivatives; stilbene derivatives; oxazine derivatives; naphthalimide derivatives; pyrazine derivatives; benzimidazole derivatives; benzoxazole derivatives; benzothiazole derivatives; imidazopyridine derivatives; azole derivatives; compounds having condensed aryl rings such as anthracene and their derivatives; aromatic amine derivatives; and organometallic complex compounds. Compounds represented by the above-mentioned general formula (1) are also suitable as luminescent materials included in the composition of the present invention because they exhibit luminescence with high color purity. The composition of the present invention may contain two or more luminescent materials (a), including at least one compound represented by the general formula (1).
[0133] Examples of the luminescent material (b) include cyanine derivatives such as 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyllyl)-4H-pyran, rhodamine derivatives such as rhodamine B, rhodamine 6G, rhodamine 101, and sulforhodamine 101, pyridine derivatives such as 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)-pyridinium-perchlorate, perylene derivatives such as N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-bisdicarboimide, as well as porphyrin derivatives, pyromethene derivatives, oxazine derivatives, pyrazine derivatives, compounds having condensed aryl rings such as naphthacene and dibenzodiindenoperylene and their derivatives, and organometallic complex compounds. Furthermore, the compound represented by the above-mentioned general formula (1) is also suitable as a luminescent material to be included in the composition of the present invention because it exhibits luminescence with high color purity. The composition of the present invention may contain two or more light-emitting materials (b) including a compound represented by general formula (1) as at least one light-emitting material.
[0134] In one embodiment of the composition of the present invention, the compound represented by general formula (1) is a light-emitting material that exhibits emission observed in the region of 500 nm to less than 580 nm when excitation light is used, such as the light-emitting material (a) described above. In this case, high-purity green emission is obtained, and the color reproducibility in the green region is improved. For this reason, it is preferable that the compound represented by general formula (1) is a light-emitting material that exhibits the green emission (for example, light-emitting material (a)).
[0135] Another aspect of the composition of the present invention is that the compound represented by general formula (1) is a light-emitting material (e.g., light-emitting material (b)) that exhibits emission observed in the region of 580 nm to less than 750 nm, as described above. In this case, a red emission with high color purity is obtained, and the color reproducibility in the red region is improved. For this reason, it is preferable that the compound represented by general formula (1) is a light-emitting material that exhibits the red emission.
[0136] As mentioned above, in order to improve color reproducibility, it is preferable that the full width at half maximum (FWHM) of the emission spectra of blue, green, and red be small, and in particular, small FWHMs of the emission spectra of green and red light are effective in improving color reproducibility. For example, the FWHM of the emission spectrum of the above-mentioned light-emitting material (a) is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 35 nm or less, and particularly preferably 30 nm or less. The FWHM of the emission spectrum of the above-mentioned light-emitting material (b) is preferably 60 nm or less, more preferably 50 nm or less, even more preferably 45 nm or less, and particularly preferably 40 nm or less.
[0137] The content of the luminescent material in the composition of the present invention can be selected according to the molar extinction coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the thickness and transmittance of the optical component (color conversion sheet, etc.) to be fabricated. Here, the content of the luminescent material refers to the total content if the composition of the present invention contains two or more types of luminescent materials. The content of the luminescent material is 1.0 × 10¹⁶ per 100 parts by weight of the binder resin contained in the composition of the present invention.-2 Preferably, the amount is between parts by weight and 5 parts by weight.
[0138] Furthermore, if the composition of the present invention contains both a light-emitting material (a) that emits green light and a light-emitting material (b) that emits red light, a portion of the green light will be converted to red light, therefore the content of the above-mentioned light-emitting material (a) w a And the content of the luminescent material (b) w b That is, lol a ≧w b It is preferable that the relationship is as follows. Also, the content ratio w of these light-emitting materials (a) and (b) a :w b The ratio is preferably 200:1 to 3:1. However, the content w a and content w b This is a weight percentage relative to the weight of the binder resin contained in the composition of the present invention.
[0139] The compositions of the present invention may contain, as optional, other compounds in addition to the compound represented by general formula (1) as the luminescent material. For example, to increase the energy transfer efficiency from excitation light to the compound represented by general formula (1), the compositions of the present invention may contain an assist dopant. Furthermore, if emission color is to be considered, the compositions of the present invention may further contain a desired organic luminescent material or known luminescent materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots, and may contain two or more of these. In order to achieve highly efficient color conversion, the luminescent material is preferably a material that exhibits luminescence characteristics with a high quantum yield, and among these, quantum dots and organic luminescent materials are preferred. Furthermore, from the viewpoint of dispersion uniformity, reduction of usage, and reduction of environmental impact, it is even more preferable to use an organic luminescent material as the luminescent material.
[0140] Examples of organic light-emitting materials include those listed below. For example, compounds having condensed aryl rings such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluorantene, fluorene, and indene, and their derivatives, are suitable organic light-emitting materials. In addition, compounds having heteroaryl rings such as furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine, as well as their derivatives and borane derivatives, are suitable organic light-emitting materials.
[0141] Furthermore, suitable organic light-emitting materials include stilbene derivatives such as 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)ethenyl)biphenyl, and 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, pyromethene derivatives, and diketopyrrolo[3,4-c]pyrrole derivatives. Also, suitable organic light-emitting materials include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole and their metal complexes, cyanine compounds such as indocyanine green, xanthene compounds such as fluorescein, eosin, and rhodamine, and thioxanthene compounds.
[0142] Furthermore, polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives and their metal complexes, porphyrin derivatives and their metal complexes, oxazine compounds such as Nile Red and Nile Blue, helicene compounds, and aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine are listed as suitable organic light-emitting materials. In addition, organometallic complex compounds such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), europium (Eu), and rhenium (Re) are listed as suitable organic light-emitting materials. However, the organic light-emitting materials in the present invention are not limited to those listed above.
[0143] The organic light-emitting material may be a fluorescent light-emitting material or a phosphorescent light-emitting material, but a fluorescent light-emitting material is preferred in order to achieve high color purity. Furthermore, as mentioned above, in order to improve color reproducibility, it is preferable that the full width at half maximum of the emission spectra of each color (blue, green, and red) is small. For this reason, the full width at half maximum of the emission spectrum at the emission peak wavelength of at least one light-emitting material contained in the composition of the present invention is preferably 60 nm or less, and more preferably 50 nm or less.
[0144] Examples of organic light-emitting materials other than compounds represented by general formula (1) are shown below, but the compositions of the present invention are not particularly limited to these.
[0145]
[0146] Another embodiment of the composition of the present invention is a light-absorbing composition. In the present invention, a light-absorbing composition is a composition that absorbs at least a portion of light when irradiated with some light, and whose main function is light absorption. Here, the light-absorbing composition in the present invention may also have a color conversion function, but if its main function is to utilize the color-converted light as output light, it is classified as a color-converting composition. One example of a light-absorbing composition that also has a color conversion function is when the emission quantum yield of the light-absorbing composition is not zero but sufficiently low, for example, when the emission quantum yield of the light-absorbing composition is less than 50%.
[0147] The light-absorbing composition of the present invention preferably contains at least one of light-absorbing material (c) and light-absorbing material (d). Here, light-absorbing material (c) is a material having a peak wavelength of absorption spectrum in the region of 470 nm to less than 530 nm. Light-absorbing material (d) is a material having a peak wavelength of absorption spectrum in the region of 540 nm to less than 640 nm.
[0148] As the light-absorbing material (c), the same group of materials as the light-emitting material (a) described above can be suitably used. In particular, the compound represented by the general formula (1) described above can be suitably used as the light-absorbing material (c) because it has a large molar extinction coefficient and a small full width at half maximum of the absorption spectrum at the peak wavelength of light absorption.
[0149] As the light-absorbing material (d), the same group of materials as the light-emitting material (b) described above can be suitably used. In particular, the compound represented by the general formula (1) described above can be suitably used as the light-absorbing material (d) because it has a large molar extinction coefficient and a small full width at half maximum of the absorption spectrum at the peak wavelength of light absorption.
[0150] <Binder Resin> The composition of the present invention includes a binder resin in addition to the compound represented by general formula (1). Preferably, the binder resin is a material with excellent moldability, transparency, heat resistance, etc. Examples of binder resins include, for example, photocurable resist materials having reactive vinyl groups such as acrylic acid-based, methacrylic acid-based, polyvinyl cinnamate-based, and ring rubber-based materials; epoxy resins; silicone resins (including organopolysiloxane cured products (crosslinked products) such as silicone rubber and silicone gel); urea resins; fluororesins; polycarbonate resins; acrylic resins; urethane resins; melamine resins; polyvinyl resins; polyamide resins; phenolic resins; polyvinyl alcohol resins; cellulose resins; aliphatic ester resins; aromatic ester resins; aliphatic polyolefin resins; and aromatic polyolefin resins. Furthermore, mixtures or copolymers of these resins may be used as the binder resin. By appropriately designing these resins, a binder resin useful for the composition of the present invention and for optical components using the composition can be obtained.
[0151] Among these resins, from the viewpoint of transparency and dispersibility of light-emitting and light-absorbing materials, it is preferable to use acrylic resin, copolymer resins containing acrylic acid ester or methacrylic acid ester moieties, polyester resins, cycloolefin resins, epoxy resins, or silicone resins. Furthermore, from the viewpoint of heat resistance, hydrogenated styrene resins, resins having a fluorene skeleton, and copolymer resins containing these resins can also be suitably used.
[0152] Examples of binder resins include thermosetting resins, photocurable resins, and thermoplastic resins. Thermoplastic resins are suitable as binder resins because they have few reactive functional groups and few reactive impurities such as polymerization initiators and crosslinking agents. Furthermore, from the viewpoint of heat resistance, thermosetting resins and photocurable resins can be suitably used as binder resins.
[0153] When the binder resin is a thermoplastic resin, the glass transition temperature (Tg) of the binder resin is not particularly limited, but is preferably 30°C to 180°C. When the Tg of the binder resin is 30°C or higher, the molecular motion of the binder resin due to heat from incident light from a light source and operating heat from equipment is suppressed, thereby suppressing changes in the dispersion state of light-emitting materials and light-absorbing materials in the binder resin, and thus preventing deterioration of the durability of the composition. Furthermore, when the Tg of the binder resin is 180°C or lower, the flexibility of the binder resin when molded into a sheet or the like can be ensured. The Tg of the binder resin is more preferably 50°C to 170°C, even more preferably 70°C to 160°C, and particularly preferably 90°C to 150°C. The glass transition temperature of thermoplastic resins can be measured using a commercially available measuring instrument (for example, a differential scanning calorimeter manufactured by Seiko Electronics Industries, Ltd. (product name DSC6220, heating rate 0.5°C / min)).
[0154] Furthermore, the binder resin is preferably a polymer or hydrogenated product of at least one monomer selected from the group consisting of acrylic acid esters, methacrylic acid esters, and styrene, with a Tg of 100°C or higher. In this case, a Tg of 110°C or higher is more preferable, and 120°C or higher is particularly preferable. These resins can be obtained by known methods, such as copolymerizing each raw material monomer in the presence of a polymerization initiator, or by performing structural transformation after polymerization through chemical reactions such as addition reactions, substitution reactions, or oxidation-reduction reactions. Commercially available products can also be used as binder resins.
[0155] <Additives> In addition to the compound represented by general formula (1) and the binder resin, the composition of the present invention may optionally contain other components (e.g., additives). Examples of additives include fillers, light stabilizers, antioxidants, processing and heat stabilizers, light-resistant stabilizers such as ultraviolet absorbers, dispersants and leveling agents for stabilizing the coating film, scattering agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, pigments, and adhesion aids such as silane coupling agents as film surface modifiers.
[0156] Examples of fillers include fumed silica, glass powder, quartz powder and other fine particles, titanium dioxide, zirconia oxide, barium titanate, zinc oxide, and silicone fine particles. The composition of the present invention may contain two or more of these as fillers.
[0157] Examples of light stabilizers include, but are not limited to, complexes or salts with organic acids containing tertiary amines, catechol derivatives, and at least one transition metal selected from the group consisting of nickel (Ni), scandium (Sc), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co), copper (Cu), yttrium (Y), zirconium (Zr), molybdenum (Mo), silver (Ag), and lanthanides. Furthermore, these light stabilizers may be used individually or in combination.
[0158] Examples of antioxidants include phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol, but the product is not limited to these. These antioxidants may be used individually or in combination.
[0159] Examples of processing and heat stabilizing agents include phosphorus-based stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine, but are not limited to these. These stabilizers may be used individually or in combination.
[0160] Examples of light-resistant stabilizers include benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, as well as hindered amine compounds such as piperidine derivatives and their oxides, including bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, and 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate. However, the list is not limited to these. These light-resistant stabilizers may be used individually or in combination.
[0161] As scattering particles, inorganic particles having a refractive index of 1.7 to 2.8 are preferred. Examples of such inorganic particles include titania, zirconia, alumina, ceria, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfides, titanium or zirconium hydroxides, and the like.
[0162] In the composition of the present invention, the content of these additives can be set according to the molar extinction coefficient, fluorescence quantum yield, and absorption intensity at the excitation wavelength of the compound, as well as the size, thickness, and transmittance of the optical component to be fabricated. The lower limit of the content of these additives is 1.0 × 10¹⁶ per 100 parts by weight of the binder resin. -3 Preferably, it is 1.0 × 10 parts by weight or more. -2 It is more preferably 1.0 × 10 parts by weight or more. -1 It is particularly preferable that the amount be parts by weight or more. Furthermore, the content (upper limit) of these additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, and particularly preferably 10 parts by weight or less, per 100 parts by weight of the binder resin.
[0163] <Solvent> In addition to the compound represented by general formula (1) and binder resin, the composition of the present invention may further contain a solvent. Preferably, the solvent can adjust the viscosity of the resin in a fluid state and does not excessively affect the luminescence and durability of the luminescent material. Examples of such solvents include water, 2-propanol, ethanol, toluene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, cyclohexane, tetrahydrofuran, acetone, terpineol, texanol, 1,2-dimethoxyethane, methyl cellsolve, ethyl cellsolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, propylene glycol monomethyl ether acetate, and the like. The composition of the present invention may use one of these solvents, or it may be possible to use a mixture of two or more of these solvents. Among these solvents, toluene, methyl ethyl ketone, methyl acetate, ethyl acetate, and tetrahydrofuran are preferably used because they leave little residual solvent after drying.
[0164] In the optical member described later according to embodiments of the present invention, the amount of residual solvent in the optical functional layer of the optical member (the amount of solvent remaining in the optical functional layer after drying) is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and particularly preferably 0.5% by mass or less, from the viewpoint of further improving the durability of the optical member. The amount of residual solvent in the optical functional layer can be measured by gas chromatography.
[0165] <Method for Manufacturing the Composition> An example of a method for manufacturing the composition according to the embodiment of the present invention is described below. In this method, the composition can be obtained by mixing the aforementioned light-emitting material, light-absorbing material, binder resin, and other additives and solvents as needed to a predetermined composition, and then homogeneously mixing or kneading them using a stirrer / kneader. Examples of stirrers / kneaders include homogenizers, orbital stirrers, three-roller stirrers, ball mills, planetary ball mills, bead mills, etc. Degassing under vacuum or reduced pressure conditions is also preferably performed after mixing or dispersion, or during the mixing or dispersion process. In addition, certain components may be mixed in advance, or treatments such as aging may be performed. It is also possible to remove the solvent using an evaporator to obtain the desired solid content concentration.
[0166] <Optical Component> An optical component according to an embodiment of the present invention (hereinafter sometimes abbreviated as "optical component of the present invention") includes the above-mentioned composition (composition of the present invention) or a cured product thereof.
[0167] One embodiment of the optical component of the present invention is a color-converting component. That is, the color-converting component includes the composition of the present invention or a cured product thereof. In the present invention, a color-converting component refers to an optical component that emits light of a different wavelength from the light when irradiated with some light.
[0168] Another embodiment of the optical member of the present invention is a light-absorbing member. That is, the light-absorbing member includes the composition of the present invention or a cured product thereof. In the present invention, a light-absorbing member is an optical member that absorbs at least a portion of the light when irradiated with some light, and whose main function is light absorption. Here, the light-absorbing member in the present invention may also have a color conversion function, but if its main function is to utilize the color-converted light as output light, it is classified as a color-converting member. One example of a light-absorbing member that also has a color conversion function is when the emission quantum yield of the light-absorbing member is not zero but sufficiently low, for example, when the emission quantum yield of the light-absorbing member is less than 50%.
[0169] The shape of the optical component of the present invention is not particularly limited. For example, the shape of the optical component of the present invention may be layered, granular, fibrous, etc. One embodiment of the optical component of the present invention is an optical sheet. The optical sheet comprises an optical functional layer which includes an optical functional layer containing the composition of the present invention, or a layer which includes a cured product formed by curing the composition (a cured product of the composition of the present invention).
[0170] When the optical component of the present invention is a color conversion component, the optical functional layer provided by the color conversion component is a color conversion layer. When the optical component of the present invention is a light absorbing component, the optical functional layer provided by the light absorbing component is a light absorbing layer.
[0171] The optical member of the present invention may have a single optical functional layer or may have multiple optical functional layers. When the optical member of the present invention has multiple optical functional layers, each of these optical functional layers may be directly laminated or laminated via an intermediate layer such as an adhesive layer. Furthermore, the optical member of the present invention may have a base layer or a barrier layer as needed, and may have two or more of these layers.
[0172] The substrate layer of the optical component of the present invention is not particularly limited, and a layer made of a known substrate such as metal, film, glass, ceramic, or paper can be used. Among these, glass and resin films are preferably used. As for the resin film, films made of resins such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyphenylene sulfide, polycarbonate, polypropylene, polyimide, aramid, and silicone are preferred. For ease of peeling of the sheet, the surface of the substrate layer may be pre-treated for release. Similarly, to improve the adhesion between layers, the surface of the substrate layer may be pre-treated for easy adhesion.
[0173] When the above-mentioned substrate layer is a film-like layer, there are no particular restrictions on the thickness of the substrate layer, but a lower limit of 12 μm or more is preferred, and a lower limit of 38 μm or more is preferred. Furthermore, an upper limit of 5000 μm or less is preferred, and a lower limit of 3000 μm or less is preferred.
[0174] Furthermore, the substrate constituting the above-mentioned substrate layer can also be, for example, a barrier film, a light guide plate, a diffuser plate, a diffuser film, a prism sheet, a reflective polarizing film, a wavelength-selective reflective film, a wavelength-selective transmitted film, or a wavelength-selective absorbent film.
[0175] The barrier layer of the optical component of the present invention is preferably one that suppresses the intrusion of oxygen, moisture, heat, etc., into the optical functional layer. The optical component of the present invention may have two or more such barrier layers. For example, the optical component of the present invention may have barrier layers on both sides of the optical functional layer, or it may have a barrier layer on one side of the optical functional layer.
[0176] The optical component of the present invention preferably has an oxygen barrier layer as one aspect of the barrier layer. Having an oxygen barrier layer in the optical component of the present invention is preferable because it can suppress oxidative degradation of the light-emitting material and light-absorbing material in the optical functional layer due to singlet oxygen generated by a dye sensitization mechanism or the like.
[0177] Examples of oxygen barrier layers include layers composed of inorganic oxides such as silicon oxide, aluminum oxide, titanium oxide, tantalum oxide, zinc oxide, tin oxide, indium oxide, yttrium oxide, and magnesium oxide; inorganic nitrides such as silicon nitride, aluminum nitride, titanium nitride, and silicon carbide nitride; metal oxide thin films or metal nitride thin films with other elements added to these; or films containing various resins such as polyvinylidene chloride, acrylic resins, silicone resins, melamine resins, urethane resins, fluororesins, and polyvinyl alcohol resins such as saponified vinyl acetate. The oxygen barrier layer may contain two or more of these materials.
[0178] Typical structural examples of the optical member of the present invention include, for example, the optical sheet structures shown in the first to sixth examples below. However, the optical member of the present invention is not limited to the optical sheet structures shown below.
[0179] Figure 1 is a schematic cross-sectional view showing a first example of an optical member according to an embodiment of the present invention. As shown in Figure 1, the first example of optical member 1A is an optical sheet having a laminated structure of a base layer 10 and an optical functional layer 11. This optical functional layer 11 is a layer containing the composition of the present invention, and can be obtained, for example, by curing the composition of the present invention. In this structural example of optical member 1A, the optical functional layer 11 is laminated on the base layer 10.
[0180] Figure 2 is a schematic cross-sectional view showing a second example of an optical member according to an embodiment of the present invention. As shown in Figure 2, the optical member 1B of the second example is an optical sheet having a laminated structure of a plurality of base material layers 10A, 10B and an optical functional layer 11. In this structural example of optical member 1B, the optical functional layer 11 is sandwiched between the plurality of base material layers 10A, 10B.
[0181] Figure 3 is a schematic cross-sectional view showing a third example of an optical member according to an embodiment of the present invention. As shown in Figure 3, the optical member 1C of the third example is an optical sheet having a laminated structure of a plurality of base material layers 10A, 10B, an optical functional layer 11, and a plurality of barrier layers 12A, 12B. In this structural example of optical member 1C, the optical functional layer 11 is sandwiched between the plurality of barrier layers 12A, 12B, and furthermore, the laminate of these optical functional layer 11 and the plurality of barrier layers 12A, 12B is sandwiched between the plurality of base material layers 10A, 10B. Each of these plurality of barrier layers 12A, 12B is an oxygen barrier layer in the optical member 1C that prevents deterioration of the optical functional layer 11 by oxygen. Note that each of these plurality of barrier layers 12A, 12B is not limited to an oxygen barrier layer, but may also be a layer that prevents deterioration of the optical functional layer 11 by moisture or heat.
[0182] Figure 4 is a schematic cross-sectional view showing a fourth example of an optical member according to an embodiment of the present invention. As shown in Figure 4, the optical member 1D of the fourth example is an optical sheet having a laminated structure in which a plurality of optical functional layers 11A and 11B are sandwiched between a plurality of base material layers 10A and 10B. In this structural example of the optical member 1D, the laminate of the plurality of optical functional layers 11A and 11B is laminated on a base material layer 10A in the order of optical functional layer 11A, optical functional layer 11B, and further, another base material layer 10B is laminated on top of this optical functional layer 11B. That is, the optical member 1D comprises a plurality of base material layers 10A and 10B and a plurality of optical functional layers 11A and 11B, and the plurality of optical functional layers 11A and 11B are sandwiched between the plurality of base material layers 10A and 10B.
[0183] Figure 5 is a schematic cross-sectional view showing a fifth example of an optical member according to an embodiment of the present invention. As shown in Figure 5, the fifth example of optical member 1E is an optical sheet having a laminated structure in which an intermediate layer 13 is sandwiched between a plurality of optical functional layers 11A and 11B, and the laminate of these plurality of optical functional layers 11A and 11B and the intermediate layer 13 is sandwiched between a plurality of base material layers 10A and 10B. In this structural example of optical member 1E, the laminate of the plurality of optical functional layers 11A and 11B and the intermediate layer 13 is laminated on a base material layer 10A in the order of optical functional layer 11A, intermediate layer 13, and optical functional layer 11B, and furthermore, another base material layer 10B is laminated on top of this optical functional layer 11B. In other words, the optical member 1E comprises a plurality of base material layers 10A, 10B, a plurality of optical functional layers 11A, 11B, and an intermediate layer 13, and contains a laminated structure of optical functional layer 11B / intermediate layer 13 / optical functional layer 11A sandwiched between these plurality of base material layers 10A, 10B.
[0184] Figure 6 is a schematic cross-sectional view showing a sixth example of an optical member according to an embodiment of the present invention. As shown in Figure 6, the sixth example of optical member 1F is an optical sheet having a laminated structure in which an intermediate layer 13 is sandwiched between a plurality of optical functional layers 11A, 11B, the laminate of these plurality of optical functional layers 11A, 11B and the intermediate layer 13 is sandwiched between a plurality of barrier layers 12A, 12B, and the laminate of these plurality of optical functional layers 11A, 11B, the intermediate layer 13 and the barrier layers 12A, 12B is sandwiched between a plurality of base material layers 10A, 10B. These plurality of barrier layers 12A, 12B are formed so as to sandwich the laminate of the plurality of optical functional layers 11A, 11B via the intermediate layer 13 from both sides in the lamination direction. In this example of the structure of optical member 1F, the barrier layer 12A, optical functional layer 11A, intermediate layer 13, optical functional layer 11B, and barrier layer 12B are laminated on the base material layer 10A in this order. As a result, a laminate with a layered structure consisting of a barrier layer 12B / optical functional layer 11B / intermediate layer 13 / optical functional layer 11A / barrier layer 12A is formed on the base material layer 10A. Furthermore, as shown in Figure 6, the base material layer 10B is laminated on the barrier layer 12B at the upper end in the lamination direction of this laminate.
[0185] In each of the optical members 1A, 1B, 1C, 1D, 1E, and 1F shown in Figures 1 to 6, the layers of the laminated structure may be in direct contact with each other, or they may be laminated via an adhesive layer (not shown).
[0186] Another embodiment of the optical component of the present invention (an embodiment different from the optical sheet described above) is an optical substrate. This optical substrate, for example, comprises a plurality of optical functional layers on a substrate. Although not specifically shown, partitions may be formed on the optical substrate, and in this optical substrate, the optical functional layers can be arranged between the partitions (in recesses).
[0187] The optical component of the present invention may further include, depending on the required function, an auxiliary layer having a light diffusion layer, an adhesive layer, an anti-reflective function, an anti-glare function, an anti-reflective anti-glare function, a hard coat function (abrasion resistance function), an anti-static function, an anti-fouling function, an electromagnetic wave shielding function, an infrared cut function, an ultraviolet cut function, a polarization function, a color tuning function, and so on.
[0188] <Method for Manufacturing Optical Components> The method for manufacturing optical components according to the embodiments of the present invention is not particularly limited as long as it is a method that can mold the composition of the present invention into a desired shape. For example, one method is to form an optical functional layer in the optical component of the present invention by applying the composition of the present invention onto a substrate and drying it. If the binder resin contained in the composition of the present invention is a thermosetting resin, the optical functional layer may be formed by applying the composition to a substrate or the like and then heating and curing the composition. If the binder resin contained in the composition of the present invention is a photocurable resin, the optical functional layer may be formed by applying the composition to a substrate or the like and then photocuring the composition. Other methods include kneading the composition of the present invention while heating it and molding it using an extruder, or putting the composition of the present invention into a mold and molding it by heating, cooling, drying, etc.
[0189] In the method for manufacturing optical components described above, the composition of the present invention can be applied using a reverse roll coater, blade coater, comma coater, slit die coater, direct gravure coater, offset gravure coater, kiss coater, natural roll coater, air knife coater, roll blade coater, two-stream coater, rod coater, wire bar coater, applicator, dip coater, curtain coater, spin coater, knife coater, etc. However, the application of the composition is not limited to these methods.
[0190] In the method for manufacturing optical components described above, the coating of the composition can be dried using a general heating device such as a hot air dryer or an infrared dryer. In this case, the heating temperature is preferably 60°C to 200°C, and the heating time is preferably 2 minutes to 4 hours. It is also possible to heat-cur the composition in stages using methods such as step curing.
[0191] When forming an optical functional layer by heat curing of the above composition, an example of a heating device is a hot air oven. In this case, the heating conditions can be selected according to the binder resin in the composition. For example, a heating temperature of 100°C to 300°C is preferred, and a heating time of 1 minute to 2 hours is preferred.
[0192] When forming an optically functional layer by photocuring of the above composition, it is preferable to irradiate the composition with high-energy light such as ultraviolet light. In this case, the light irradiation conditions can be selected according to the binder resin in the composition. For example, the wavelength of the irradiated light is preferably 200 nm to 500 nm, and the irradiation dose is preferably 10 mJ / cm². 2 ~10 J / cm 2 It is preferable.
[0193] Furthermore, in the manufacturing method of the optical component described above, it is also possible to change the substrate layer as needed after the optical functional layer has been fabricated. In this case, simple methods include, for example, replacing the layer using a hot plate, or using a vacuum laminator or a dry film laminator.
[0194] <Light Source Unit> A light source unit according to an embodiment of the present invention (hereinafter sometimes abbreviated as "light source unit of the present invention") is configured to include at least a light source and the above-described composition or optical member. Examples of the optical member include the above-described color conversion member and light absorbing member. That is, the optical unit of the present invention includes at least a light source and at least one of the optical member, color conversion member, and light absorbing member of the present invention. When the light source unit of the present invention includes the above-described composition, the arrangement of the light source and the composition is not particularly limited, and the composition may be applied directly to the light source, or the composition may be applied to a substrate such as a film or glass that is separated from the light source. Furthermore, when the light source unit of the present invention includes the above-described optical member, the arrangement of the light source and the optical member is not particularly limited, and the light source and the optical member may be in close contact, or they may be in a remote configuration separated from each other. In addition, the light source unit of the present invention may further include a color filter for the purpose of increasing color purity, and may also include optical members such as a prism sheet, a reflective polarizing film, or a diffusion film for the purpose of improving brightness or uniformizing emitted light.
[0195] One embodiment of the light source unit of the present invention is a configuration comprising an optical member (optical sheet) having the configuration illustrated in Figure 5, wherein the light source is located below the plane of Figure 5 (below the base material layer 10A), and a prism sheet and a reflective polarizing film are laminated above the plane of Figure 5 (above the base material layer 10B). A diffuser plate may be provided between the light source and the optical member shown in Figure 5, and a reflector plate may be provided below the light source.
[0196] Another embodiment of the light source unit of the present invention includes a light source and a light guide plate, wherein an optical functional layer formed by directly applying the composition of the present invention is laminated on the light-emitting side of the light guide plate. In a light source unit having this configuration, a light diffusion layer or a wavelength-selective transmission layer may be further formed on the optical functional layer.
[0197] The light source unit of the present invention is useful for various light sources such as spatial illumination and backlighting. Specifically, the light source unit of the present invention can be used in applications such as displays, lighting devices, interiors, signs, and billboards, but is particularly suitable for use in displays and lighting devices.
[0198] <Light Source> The light source unit of the present invention can be any light source that emits light in a wavelength range that can be absorbed by the light-emitting material or light-absorbing material used in the composition of the present invention. For example, any excitation light source such as a hot cathode tube, cold cathode tube, fluorescent light source such as inorganic electroluminescence (EL), organic EL element light source, light-emitting diode (LED) light source, incandescent light source, or sunlight can be used in principle. Among these, from the viewpoint of color purity, LEDs or organic EL elements are preferred as the light source, and LEDs are more preferred.
[0199] For example, in display and lighting applications, LEDs or organic EL elements having maximum emission in the wavelength range of 400 nm to 500 nm are preferred light sources from the viewpoint of improving the color purity of blue light. Furthermore, as the above light source, blue LEDs having maximum emission in the wavelength range of 430 nm to 480 nm are more preferred, and blue LEDs having maximum emission in the wavelength range of 445 nm to 470 nm are particularly preferred.
[0200] The above light source may have one type of emission peak or two or more types of emission peaks, but to improve color purity, one with one type of emission peak is preferable. It is also possible to use multiple light sources with different types of emission peaks in any combination.
[0201] <Displays and Lighting Devices> A display according to an embodiment of the present invention comprises at least a light source unit having a light source and the composition or optical member of the present invention as described above. That is, the display comprises a light source and at least one of the composition or optical member of the present invention, a color conversion member, and a light absorbing member. For example, a display such as a liquid crystal display uses the above-described light source unit as its backlight unit and is configured to emit white light with high color purity of blue, green, and red by combining a blue LED light source with a color conversion composition or color conversion member that converts a portion of the blue light from the blue LED light source into green and red light. Alternatively, a display according to the present invention may be configured to emit white light with high color purity of blue, green, and red by combining a white LED light source or a white organic EL element light source with a light absorbing composition or light absorbing member that absorbs a portion of the blue, green, and red light from these white light sources.
[0202] Furthermore, an illumination device according to an embodiment of the present invention comprises at least a light source unit having a light source and the composition or optical member of the present invention, as described above. That is, the illumination device comprises a light source and at least one of the composition or optical member of the present invention, a color conversion member, and a light absorbing member. For example, this illumination device is configured to emit white light by combining a blue LED light source as a light source unit with a color conversion composition or color conversion member that converts the blue light from this blue LED light source into light with a longer wavelength.
[0203] The present invention will be described below with reference to examples, but the present invention is not limited to the following examples. First, the evaluation methods and materials such as light-emitting materials and light-absorbing materials in the examples and comparative examples will be described.
[0204] < 11H-NMR measurement > Compound 1 H-NMR was performed using a superconducting FTNMR EX-270 (manufactured by JEOL Ltd.) with deuterated chloroform solution.
[0205] <Measurement of emission spectrum> In measuring the emission spectrum, the luminescent material compound is dissolved in toluene at a rate of 1 × 10⁻⁶ -5 The compound was dissolved at a concentration of mol / L, and its emission spectrum was measured using a fluorescence spectrophotometer (Fluoromax 4, Horiba, Ltd.). From the obtained emission spectrum, the emission wavelength (peak wavelength) and full width at half maximum (FMAX) of the compound were determined. These results are shown in Tables 1 to 3 below.
[0206] <Measurement of Absorption Spectrum> In the measurement of the absorption spectrum, a compound that is a light-absorbing material is dissolved in toluene at a concentration of 1 × 10⁻¹⁶. -5 The compound was dissolved at a concentration of mol / L, and its absorption spectrum was measured using an ultraviolet-visible-near-infrared spectrophotometer (UH5700, Hitachi, Ltd.). From the obtained absorption spectrum, the absorption wavelength (peak wavelength) and full width at half maximum (FMAX) of the compound were determined. These results are shown in Tables 4 and 5 below.
[0207] <Evaluation of Light Durability> In the evaluation of the light durability of the color conversion material, in each example and comparative example, a light-emitting device equipped with the fabricated color conversion material and a blue LED element (USHIO EPITEX; model number SMBB450H-1100, emission peak wavelength: 450 nm) was subjected to a current of 300 mA to light up the blue LED element, and the initial emission peak intensity was measured using a spectroradiometer (CS-1000, Konica Minolta). The distance between the color conversion material and the blue LED element in this light-emitting device was set to 3 cm. Subsequently, the light from the blue LED element was continuously irradiated in a 50°C environment, and the time until the emission peak intensity decreased by 5% was observed to evaluate the light durability of the color conversion material.
[0208] In evaluating the photodurability of the light-absorbing material, in each example and comparative example, a light-emitting device equipped with the fabricated light-absorbing material and a blue LED element (USHIO EPITEX; model number SMBB450H-1100, emission peak wavelength: 450 nm) was subjected to a 300 mA current to light up the blue LED element, and the initial peak intensity of the blue light transmitted through the light-absorbing material was measured using a spectroradiometer (CS-1000, Konica Minolta). The distance between the light-absorbing material and the blue LED element in this light-emitting device was set to 3 cm. Subsequently, the photodurability of the light-absorbing material was evaluated by continuously irradiating it with light from the blue LED element in a 50°C environment and observing the time until the peak intensity of the blue light transmitted through the light-absorbing material increased by 5%.
[0209] <Luminescent Materials, Light-Absorbing Materials> In the following examples and comparative examples, compounds D-1 to D-16 were used as luminescent materials or light-absorbing materials contained in optical components such as color conversion sheets. Compounds D-1 to D-16 are the compounds shown below.
[0210]
[0211]
[0212]
[0213] (Synthesis Example 1) The synthesis method for compound D-1 in Synthesis Example 1 of the present invention will be described below.
[0214]
[0215] In the synthesis of compound D-1, 4-hydroxyphenylbenzaldehyde (244 mg) was placed in a flask and purged with nitrogen. Dehydrated dichloromethane (10 mL) was added, and the mixture was stirred at room temperature to form a homogeneous solution, which was then cooled to 0°C. Trimellitus anhydride chloride (463 mg) and triethylamine (364 mg) were slowly added, and the mixture was stirred at room temperature for 2 hours. Then, water (20 mL) was slowly added, the mixture was stirred, and the organic layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The resulting reaction product was purified by silica gel chromatography to obtain compound M-1 (334 mg) as a white solid.
[0216] Next, a mixed solution of compound M-1 (334 mg), ethyl 2,4-dimethylpyrrole-3-carboxylate (597 mg), and anhydrous dichloromethane (11 mL) was stirred at room temperature under a nitrogen atmosphere. Trifluoroacetic acid (1 drop) was added, and the mixture was stirred for 1 hour under a nitrogen atmosphere. An anhydrous dichloromethane solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (425 mg) was added, and the mixture was stirred for a further 3 hours. After the reaction was complete, boron trifluoride diethyl ether complex (603 mg) and diisopropylethylamine (330 mg) were added, and the mixture was stirred for 2 hours. Then, water (20 mL) was added and the mixture was stirred, and the organic layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The resulting reaction product was purified by silica gel chromatography to obtain compound D-1 (246 mg) as an orange solid. 1 The results of the 1H-NMR analysis are shown below. From these analysis results, it was confirmed that the obtained compound was compound D-1. 1 H-NMR (CDCl3, ppm): 9.08 (s, 1H), 9.05 (d, 1H), 8.96 (d, 1H), 7.53 (d, 2H), 7.26 (d, 2H), 4.27 (q, 4H), 2.83 (s, 6H), 1.63 (s, 6H), 1.32 (t, 6H)
[0217] (Synthesis Example 2) The synthesis method for compound D-6 in Synthesis Example 2 of the present invention will be described below.
[0218]
[0219] In the synthesis of compound D-6, a mixed solution of ethyl 2,4-dimethylpyrrole-3-carboxylate (334 mg), trimellitic anhydride chloride (632 mg), and anhydrous toluene (10 mL) was heated under a nitrogen stream for 4 hours under reflux. This mixed solution was cooled to room temperature, and water (20 mL) was slowly added to the cooled solution, which was then stirred, and the organic layer was separated. This organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The resulting reaction product was purified by silica gel chromatography to obtain compound M-2 (546 mg) as a pale yellow solid.
[0220] Next, a mixed solution of compound M-2 (546 mg), ethyl 2,4-dimethylpyrrole-3-carboxylate (294 mg), and anhydrous dichloromethane (11 mL) was stirred at room temperature under a nitrogen atmosphere. Methanesulfonic anhydride (557 mg) was added, and the mixture was stirred at 100°C for 4 hours under a nitrogen atmosphere. This mixed solution was cooled to room temperature, and after cooling, water (20 mL) was slowly added to the mixed solution and stirred, and the organic layer was separated. This organic layer was dried over sodium sulfate, filtered, and the solvent was removed by distillation. Anhydrous dichloromethane (11 mL) was added, and then boron trifluoride diethyl ether complex (182 mg) and diisopropylethylamine (99 mg) were added, and the mixture was stirred for 2 hours. After that, water (20 mL) was added and the mixture was stirred, and the organic layer was separated. This organic layer was dried over magnesium sulfate, filtered, and the solvent was removed by distillation. The reaction product was purified by silica gel chromatography to obtain compound D-6 (175 mg) as an orange solid. 1 The results of the 1H-NMR analysis are shown below. From these analysis results, it was confirmed that the obtained compound was compound D-6. 1 H-NMR (CDCl3, ppm): 8.93 (d, 1H), 7.86 (d, 1H), 7.68 (s, 1H), 4.27 (q, 4H), 2.83 (s, 6H), 1.63 (s, 6H), 1.32 (t, 6H)
[0221] Compounds other than those mentioned above can also be easily synthesized by changing various starting materials. Furthermore, according to known methods, the fluorine on the boron atoms can be replaced with a cyano group by reacting a boron fluoride complex, in which fluorine is substituted on the boron atoms, with trimethylsilyl cyanide and a boron trifluoride diethyl ether complex.
[0222] <Scattering Agent> In the following examples and comparative examples, titanium dioxide particles "JR-301" (manufactured by Teika Co., Ltd.) were used as the scattering agent.
[0223] Example 1 In Example 1, first, PMMA resin "BR-85" (manufactured by Mitsubishi Chemical Corporation) was used as the binder resin. 100 parts by weight of this binder resin was mixed with 0.30 parts by weight of compound D-1 as a light-emitting material, 3 parts by weight of JR-301 as a scattering agent, and 300 parts by weight of ethyl acetate as a solvent. These mixtures were then stirred and defoamed at 1000 rpm for 20 minutes using a planetary stirring and defoaming device "Mazelstar" (registered trademark) KK-400 (manufactured by Kurabo Corporation). This yielded a resin composition for producing a color conversion layer (color conversion composition of Example 1).
[0224] Next, the resin composition for producing the color conversion layer obtained above was applied onto "Lumirror" U34 (manufactured by Toray Industries, Inc., 75 μm thick) using a film applicator, and heated and dried at 120°C for 20 minutes. This formed a color conversion layer with an average film thickness of 17 μm.
[0225] When a sheet-like color-converting member having the color-converting layer formed as described above was continuously irradiated with light from a blue LED element in a 50°C environment, the time it took for the light emission peak intensity to decrease by 5% (light durability) was 50 hours. Comparing this light durability (light durability of Example 1) with Comparative Example 1 described later, Example 1 showed an improvement of approximately 1.7 times in light durability. The light-emitting material and evaluation results of Example 1 are shown in Table 1 below.
[0226] Examples 2-7 In Examples 2-7, the luminescent material was changed to one of those listed in Table 1, and the amount of luminescent material mixed was adjusted to be the same as the amount of compound D-1 in Example 1. Otherwise, the sheet-like color-converting members were manufactured and evaluated in the same manner as in Example 1. The luminescent material and evaluation results for each of Examples 2-7 are shown in Table 1.
[0227] Comparative Example 1 In Comparative Example 1, the luminescent material was changed to one of those listed in Table 1, and the amount of luminescent material mixed was adjusted to be the same as the amount of compound D-1 in Example 1. Otherwise, a sheet-like color-converting member was manufactured and evaluated in the same manner as in Example 1. The luminescent material and evaluation results for Comparative Example 1 are shown in Table 1.
[0228] Examples 8-9 In Examples 8-9, the luminescent material was changed to one of those listed in Table 2, and the amount of luminescent material mixed was adjusted to be the same as the amount of compound D-1 in Example 1. Otherwise, the sheet-like color-converting members were manufactured and evaluated in the same manner as in Example 1. The luminescent material and evaluation results for each of Examples 8-9 are shown in Table 2.
[0229] Comparative Example 2 In Comparative Example 2, the luminescent material was changed to one of those listed in Table 2, and the amount of luminescent material mixed was adjusted to be the same amount as compound D-1 in Example 1. Otherwise, the sheet-like color-converting member was manufactured and evaluated in the same manner as in Example 1. The luminescent material and evaluation results for Comparative Example 2 are shown in Table 2.
[0230] Example 10 In Example 10, a sheet-like color-converting member was prepared in the same manner as in Example 1, except that 0.03 parts by weight of compound D-10 was mixed with 100 parts by weight of binder resin as a light-emitting material.
[0231] When the sheet-like color-converting material obtained as described above was continuously irradiated with light from a blue LED element in a 50°C environment, the time it took for the light emission peak intensity to decrease by 5% (light durability) was 250 hours. Comparing this light durability (light durability of Example 10) with Comparative Example 3 described later, Example 10 showed an improvement of approximately 1.7 times in light durability. The light-emitting material and evaluation results of Example 10 are shown in Table 3 below.
[0232] Examples 11-13 In Examples 11-13, the luminescent material was changed to that listed in Table 3, and the amount of luminescent material mixed was adjusted to be the same as the amount of compound D-10 in Example 10. Otherwise, the sheet-like color-converting members were manufactured and evaluated in the same manner as in Example 10. The luminescent material and evaluation results for each of Examples 11-13 are shown in Table 2.
[0233] Comparative Example 3 In Comparative Example 3, the luminescent material was changed to the one listed in Table 3, and the amount of luminescent material mixed was adjusted to be the same amount as compound D-10 in Example 10. Otherwise, the sheet-like color-converting member was manufactured and evaluated in the same manner as in Example 10. The luminescent material and evaluation results for Comparative Example 3 are shown in Table 3.
[0234] Example 14 In Example 14, first, the acrylic resin "Oricox KC-7000" (manufactured by Kyoeisha Chemical Co., Ltd.) was used as the binder resin. 100 parts by weight of this binder resin were mixed with 0.42 parts by weight of compound D-8 as a light-absorbing material and 300 parts by weight of ethyl acetate as a solvent. These mixtures were then stirred and defoamed at 300 rpm for 30 minutes using a planetary stirring and defoaming device "Mazelstar" (registered trademark) KK-400 (manufactured by Kurabo Corporation). This yielded a resin composition for producing a light-absorbing layer (the light-absorbing composition of Example 14).
[0235] Next, the resin composition for fabricating the light-absorbing layer obtained above was applied onto "Lumirror" U34 (manufactured by Toray Industries, Inc., 75 μm thick) using a film applicator, and then heated and dried at 120°C for 20 minutes. This formed a light-absorbing layer with an average thickness of 17 μm.
[0236] When a sheet-shaped light-absorbing member having the light-absorbing layer formed as described above was continuously irradiated with light from a blue LED element in an environment of 50°C, the time it took for the peak intensity of the blue light transmitted through the light-absorbing member to increase by 5% (light durability) was 1000 hours. Comparing this light durability (light durability of Example 14) with Comparative Example 4 described later, Example 14 showed an improvement of approximately 2.6 times in light durability. The light-absorbing material and evaluation results of Example 14 are shown in Table 4 below.
[0237] Example 15 In Example 15, the light-absorbing material was changed to the one listed in Table 4, and the amount of light-absorbing material mixed was adjusted to be the same amount as compound D-8 in Example 14. Otherwise, a sheet-like light-absorbing member was fabricated and evaluated in the same manner as in Example 14. The light-absorbing material and evaluation results for Example 15 are shown in Table 4.
[0238] Comparative Example 4 In Comparative Example 4, the light-absorbing material was changed to the one listed in Table 4, and the amount of light-absorbing material mixed was adjusted to be the same amount as compound D-8 in Example 14. Otherwise, a sheet-like light-absorbing member was prepared and evaluated in the same manner as in Example 14. The light-absorbing material and evaluation results for Comparative Example 4 are shown in Table 4.
[0239] Example 16 In Example 16, a sheet-like light-absorbing member was prepared in the same manner as in Example 14, except that 0.03 parts by weight of compound D-12 was mixed with 100 parts by weight of binder resin as a light-absorbing material.
[0240] When the sheet-like light-absorbing material obtained as described above was continuously irradiated with light from a blue LED element in a 50°C environment, the time it took for the peak intensity of the blue light transmitted through the light-absorbing material to increase by 5% (light durability) was 700 hours. Comparing this light durability (light durability of Example 16) with Comparative Example 5 described later, Example 16 showed an improvement of approximately 3.9 times in light durability. The light-absorbing material and evaluation results of Example 16 are shown in Table 5 below.
[0241] Example 17 In Example 17, the light-absorbing material was changed to the one listed in Table 5, and the amount of light-absorbing material mixed was adjusted to be the same amount as compound D-12 in Example 16. Otherwise, a sheet-like light-absorbing member was fabricated and evaluated in the same manner as in Example 16. The light-absorbing material and evaluation results for Example 17 are shown in Table 5.
[0242] Comparative Example 5 In Comparative Example 5, the light-absorbing material was changed to the one listed in Table 5, and the amount of light-absorbing material mixed was adjusted to be the same amount as compound D-12 in Example 16. Otherwise, a sheet-like light-absorbing member was fabricated and evaluated in the same manner as in Example 16. The light-absorbing material and evaluation results for Comparative Example 5 are shown in Table 5.
[0243]
[0244]
[0245]
[0246]
[0247]
[0248] As described above, the compounds, compositions, optical components, color conversion components, light absorbing components, and light source units, displays, and lighting devices containing the same according to the present invention are useful for achieving both improved color reproducibility and improved durability (high light durability), and are particularly suitable for achieving both high color purity emission and light absorption and high durability.
[0249] 1A, 1B, 1C, 1D, 1E, 1F Optical components 10, 10A, 10B Substrate layers 11, 11A, 11B Optical functional layers 12A, 12B Barrier layers 13 Intermediate layer
Claims
1. A compound characterized by being represented by the following general formula (1). (In the above general formula (1), R 1 ~R 9 These R groups may be the same or different, and are selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, ester group, carbamoyl group, amide group, sulfonyl group, sulfonic acid ester group, sulfonamide group, amino group, imino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. 1 ~R 9 The groups may be adjacent to each other and form a ring structure. However, these R 1 ~R 9 R in 1 ~R 7 At least one of these groups contains a dicarboxylic acid anhydride structure.
2. In the general formula (1), at least one of R 2 , R 5 and R 7 is a group containing a dicarboxylic anhydride structure, The compound according to claim 1, characterized in that.
3. In the general formula (1) above, at least R 7 The compound according to claim 1, characterized in that it is a group containing a dicarboxylic acid anhydride structure.
4. The compound according to claim 1, characterized in that the dicarboxylic acid anhydride structure is one or more of the phthalic anhydride structure, the 1,2-cyclohexanedicarboxylic acid anhydride structure, the succinic anhydride structure, and the maleic anhydride structure.
5. The compound according to claim 1, characterized in that the group containing the dicarboxylic acid anhydride structure is a group represented by the following general formula (2). (In the above general formula (2), L is a linking group composed of a combination of 1 to 5 groups selected from the group consisting of single bonds, alkylene groups, cycloalkylene groups, heterocyclic groups, alkenylene groups, cycloalkenylene groups, alkylylene groups, arylene groups, heteroarylene groups, ether bonds, thioether bonds, carbonyl groups, ester bonds, amide bonds, sulfonyl groups, sulfonic acid ester bonds, sulfonamide bonds, amino groups, imino groups, silyl groups, siloxanyl groups, boryl groups, and phosphine oxide groups.) 6. The compound according to claim 5, characterized in that L in the general formula (2) is a linking group composed of a combination of 1 to 5 elements selected from the group consisting of a single bond, an arylene group, a carbonyl group, an ester bond, and an amide bond.
7. R in the general formula (1) 7 The compound according to claim 1, characterized in that it is a group represented by the following general formula (3).
8. R in the general formula (1) 1 ~R 6 The compound according to claim 1, characterized in that at least one of them is an ester group.
9. R in the general formula (1) 1 ~R 6 The compound according to claim 1, characterized in that at least one of them is an aryl group.
10. R in the general formula (1) 1 ~R 6 The compound according to claim 1, characterized in that at least one of them is an alkyl group.
11. R in the general formula (1) 1 ~R 6 The compound according to claim 1, characterized in that at least one of them is a group containing a fluorine atom.
12. R in the general formula (1) 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 The compound according to claim 1, characterized in that at least one of the four sets of structures is a ring structure represented by one of the following general formulas (4A) to (4D). (In the general formulas (4A) to (4D), R 101 , R 102 and R 201 ~R 204 Each of these may be the same or different, and is selected from the group consisting of hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, aryl group, heteroaryl group, hydroxyl group, thiol group, alkoxy group, alkylthio group, aryl ether group, arylthioether group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, ester group, carbamoyl group, amide group, sulfonyl group, sulfonic acid ester group, sulfonamide group, amino group, imino group, nitro group, silyl group, siloxanyl group, boryl group, and phosphine oxide group. Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocyclic ring. In addition, in each of the ring structures represented by the general formulas (4A) to (4D) above, R 101 and R 102 The rings may be formed. The "*" in the general formulas (4A) to (4D) indicates the connection to the pyromethene skeleton.
13. A composition characterized by comprising a compound according to any one of claims 1 to 12, and a binder resin.
14. An optical component comprising the composition described in claim 13 or a cured product thereof.
15. A color-changing member characterized by comprising the composition described in claim 13 or a cured product thereof.
16. A light-absorbing member characterized by comprising the composition described in claim 13 or a cured product thereof.
17. A light source unit comprising a light source and the optical member described in claim 14.
18. A light source unit comprising a light source and a color conversion member as described in claim 15.
19. A light source unit comprising a light source and a light-absorbing member as described in claim 16.
20. A display comprising a light source and the optical member described in claim 14.
21. A display comprising a light source and a color conversion member as described in claim 15.
22. A display comprising a light source and a light-absorbing member as described in claim 16.
23. An illumination device comprising a light source and an optical member as described in claim 14.
24. A lighting device comprising a light source and a color conversion member as described in claim 15.
25. A lighting device comprising a light source and a light-absorbing member as described in claim 16.