Particulate color conversion material, color conversion member, and light source unit, display, illumination device, and

Abstract

A particulate color conversion material according to one embodiment of the present invention is a particulate color conversion material having a matrix resin and at least one light-emitting material. The at least one light-emitting material contains an organic light-emitting material that emits delayed fluorescence having a half-value width of 50 nm or less.

Description

Technical Field

[0001] The present invention relates to a particulate color conversion material, a color conversion member, and a light source unit, a display, a lighting device and a color conversion substrate including the same. Background Art

[0002] There is a growing trend of research on the application of color conversion technology to liquid crystal displays, organic EL displays, lighting devices, etc. Color conversion refers to the conversion of light from a light emitter into light with a longer wavelength, for example, the conversion of blue light into green or red light.

[0003] By making a composition having the color conversion function (hereinafter referred to as "color conversion composition") into a sheet and combining it with, for example, a blue light source, it is possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By using the white light source obtained by combining the blue light source and the sheet having the color conversion function (hereinafter referred to as "color conversion sheet") as a light source unit such as a backlight unit, and combining the light source unit, a liquid crystal drive part, and a color filter, a full-color display can be produced. In addition, the white light source obtained by combining the blue light source and the color conversion sheet can also be directly used as a white light source (lighting device) such as LED lighting.

[0004] As a subject of liquid crystal displays using a color conversion method, the improvement of color reproducibility can be cited. In order to improve color reproducibility, it is effective to narrow the half-value width of each emission spectrum of blue, green, and red of the light source unit to improve the color purity of each color of blue, green, and red. As a solution, a technology using quantum dots obtained from inorganic semiconductor particles as a component of a color conversion composition has been proposed (for example, see Patent Document 1).

[0005] In addition, a technology has been proposed to use an organic light-emitting material with less concern about toxic elements such as cadmium as a component of a color conversion composition instead of quantum dots. As an example of a technology using an organic light-emitting material as a component of a color conversion composition, a technology using a coumarin derivative (for example, see Patent Document 2), a technology using a rhodamine derivative (for example, see Patent Document 3), and a technology using a pyrrole derivative (for example, see Patent Document 4) are disclosed. In addition, as an example of a technology for preventing degradation of an organic light-emitting material and improving durability, a technology for adding a light stabilizer is also disclosed (for example, see Patent Document 5).

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent Application Publication No. 2012-22028

[0009] Patent Document 2: Japanese Patent Application Publication No. 2007-273440

[0010] Patent Document 3: Japanese Patent Application Publication No. 2001-164245

[0011] Patent Document 4: Japanese Patent Application Publication No. 2011-241160

[0012] Patent Document 5: International Publication No. 2011 / 149028 Summary of the invention

[0013] Problems to be solved by the invention

[0014] As for the technology using quantum dots described in Patent Document 1, the half-value width of the green and red emission spectra is indeed narrow, and the color reproducibility is improved. However, on the other hand, quantum dots have weak resistance to heat, moisture in the air, and oxygen, and the durability is insufficient. In addition, quantum dots also have the problem of containing cadmium, etc.

[0015] In recent years, with the advancement of high definition such as 4K and 8K, high dynamic range (HDR), and high contrast based on local dimming, the required illuminance of the light source unit of the liquid crystal display has increased. As a result, the temperature of the light source unit has increased due to driving heat.

[0016] The technologies using organic light-emitting materials described in Patent Documents 2 to 4 can indeed improve color reproducibility, but the durability at high temperatures is insufficient. In addition, the existing technology such as the light stabilizer described in Patent Document 5 has the effect of improving durability, but it is insufficient as a technology for improving durability at high temperatures. In particular, in color conversion materials using organic light-emitting materials, there is a problem that the durability is significantly deteriorated at high temperatures, and the above-mentioned existing technologies have not yet been able to fully solve this problem.

[0017] The problem to be solved by the present invention is to simultaneously achieve improved color reproducibility and improved durability, especially improved durability at high temperatures, in color conversion materials used in light source units such as backlight units, displays such as liquid crystal displays, and lighting devices such as LED lighting.

[0018] Means for solving problems

[0019] In order to solve the above-mentioned problems and achieve the purpose, the present invention has the configuration described in any one of the following [1] to

[19] .

[0020] That is, the particulate color conversion material according to the present invention is characterized in that [1] it is a particulate color conversion material having a matrix resin and at least one luminescent material, wherein the at least one luminescent material includes an organic luminescent material that emits delayed fluorescence with a half-value width of less than 50 nm.

[0021] The particulate color conversion material according to the present invention is characterized in that [2] in the invention described in [1] above, the organic light-emitting material is a compound containing a partial structure represented by the general formula (1).

[0022] [Chemical formula 1]

[0023]

[0024] (In the general formula (1), B is a boron atom, N is a nitrogen atom, and C is a carbon atom. n is an integer of 0 to 2. When n is 0, the partial structure represented by the general formula (1) represents a direct bond structure between B and N.)

[0025] In addition, the particulate color conversion material according to the present invention is characterized in that [3] in the invention described in [2] above, the organic light-emitting material is a compound containing two or more partial structures represented by the general formula (1).

[0026] In addition, the particulate color conversion material according to the present invention is characterized in that [4] in the invention described in any one of [1] to [3] above, the organic light-emitting material contains a compound represented by the general formula (2) or (3).

[0027] [Chemical formula 2]

[0028]

[0029] (In the general formula (2) or (3), ring Za, ring Zb and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 6 to 30 ring carbon atoms. Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom. 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 When it is NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O. 1 and E 2Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2. 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. The substituent Ra is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxyl, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted substituted carboxyl, substituted or unsubstituted oxycarbonyl, substituted or unsubstituted ester, substituted or unsubstituted carbamoyl, substituted or unsubstituted amide, sulfonyl, substituted or unsubstituted sulfonate, substituted or unsubstituted sulfonamide, substituted or unsubstituted amino, substituted or unsubstituted imino, nitro, substituted or unsubstituted silyl, substituted or unsubstituted siloxane, substituted or unsubstituted borane, substituted or unsubstituted phosphine oxide, and substituents selected from the condensed ring and aliphatic ring formed with the adjacent substituent. In addition, the substituent Ra may be further substituted by the selected aforementioned substituents, and these substituents may be further substituted by the selected aforementioned substituents.)

[0030] In addition, the particulate color conversion material according to the present invention is characterized in that [5] in the invention described in [4] above, E in the general formula (2) is a boron atom, and E in the general formula (3) is 1 and E 2 It is BRa.

[0031] Furthermore, the color conversion member according to the present invention is characterized by [6] comprising a support body containing the particulate color conversion material according to any one of [1] to [5].

[0032] In addition, the color conversion component according to the present invention is characterized in that, [7] in the invention described in the above [6], the color conversion component includes: a first particulate color conversion material formed by a first luminescent material that exhibits luminescence with a peak wavelength observed in a region of greater than 500 nm and less than 580 nm and a first matrix resin; and a second particulate color conversion material formed by a second luminescent material that exhibits luminescence with a peak wavelength observed in a region of greater than 580 nm and less than 750 nm and a second matrix resin.

[0033] In addition, the color conversion member according to the present invention is characterized in that [8] in the invention described in [7] above, the first light-emitting material contains at least an organic light-emitting material that emits delayed fluorescence with a half-value width of 50 nm or less.

[0034] In addition, the color conversion member according to the present invention is characterized in that [9] in the invention described in [6] or [7] above, the second light-emitting material contains at least a compound represented by the general formula (4).

[0035] [Chemical formula 3]

[0036]

[0037] (In general formula (4), X is CR 7 or N. R 1 ~R 9 Each of them may be the same or different, and is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and a condensed ring and aliphatic ring formed with adjacent substituents. R 1 ~R 9 Each independently may be substituted. 1 ~R 9The substituents for each substitution are selected from hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxy, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted substituted carboxyl, substituted or unsubstituted oxycarbonyl, substituted or unsubstituted ester, substituted or unsubstituted carbamoyl, substituted or unsubstituted amide, sulfonyl, substituted or unsubstituted sulfonate, substituted or unsubstituted sulfonamide, substituted or unsubstituted amino, substituted or unsubstituted imino, nitro, substituted or unsubstituted silyl, substituted or unsubstituted siloxane, substituted or unsubstituted borane, substituted or unsubstituted phosphine oxide, and condensed rings and aliphatic rings formed with adjacent substituents.)

[0038] In addition, the color conversion component according to the present invention is characterized in that,

[10] in the invention described in any one of [6] to [9] above, the support body contains the particulate color conversion material described in any one of [1] to [5] above and at least one luminescent material.

[0039] In addition, the color conversion component of the present invention is characterized in that,

[11] in the invention described in the above-mentioned

[10] , the at least one luminescent material contains at least one of a compound containing a partial structure represented by general formula (1), a compound represented by general formula (2) and a compound represented by general formula (3).

[0040] [Chemical formula 4]

[0041]

[0042] (In the general formula (1), B is a boron atom, N is a nitrogen atom, and C is a carbon atom. n is an integer of 0 to 2. When n is 0, the partial structure represented by the general formula (1) represents a direct bond structure between B and N.)

[0043] [Chemical formula 5]

[0044]

[0045] (In the general formula (2) or (3), ring Za, ring Zb and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 6 to 30 ring carbon atoms. Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom.1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 When it is NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O. 1 and E 2 Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2. 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. The substituent Ra is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxyl, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted substituted carboxyl, substituted or unsubstituted oxycarbonyl, substituted or unsubstituted ester, substituted or unsubstituted carbamoyl, substituted or unsubstituted amide, sulfonyl, substituted or unsubstituted sulfonate, substituted or unsubstituted sulfonamide, substituted or unsubstituted amino, substituted or unsubstituted imino, nitro, substituted or unsubstituted silyl, substituted or unsubstituted siloxane, substituted or unsubstituted borane, substituted or unsubstituted phosphine oxide, and substituents selected from the condensed ring and aliphatic ring formed with the adjacent substituent. In addition, the substituent Ra may be further substituted by the selected aforementioned substituents, and these substituents may be further substituted by the selected aforementioned substituents.)

[0046] Furthermore, the color conversion member according to the present invention is characterized in that

[12] in the invention described in

[10] above, the at least one light-emitting material contains at least a compound represented by the general formula (4).

[0047] [Chemical formula 6]

[0048]

[0049] (In general formula (4), X is CR 7 or N. R 1 ~R 9 Each of them may be the same or different, and is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and a condensed ring and aliphatic ring formed with adjacent substituents. R 1 ~R 9 Each independently may be substituted. 1 ~R 9 The substituents for each substitution are selected from hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxy, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted substituted carboxyl, substituted or unsubstituted oxycarbonyl, substituted or unsubstituted ester, substituted or unsubstituted carbamoyl, substituted or unsubstituted amide, sulfonyl, substituted or unsubstituted sulfonate, substituted or unsubstituted sulfonamide, substituted or unsubstituted amino, substituted or unsubstituted imino, nitro, substituted or unsubstituted silyl, substituted or unsubstituted siloxane, substituted or unsubstituted borane, substituted or unsubstituted phosphine oxide, and condensed rings and aliphatic rings formed with adjacent substituents.)

[0050] In addition, the color conversion member according to the present invention is characterized in that

[13] in any one of the inventions [6] to

[12] , the oxygen permeability of the support is 1.0 cc / m 2 ·day·atm or less.

[0051] Furthermore, the color conversion member according to the present invention is characterized in that

[14] in any one of the inventions [6] to

[13] above, wherein an oxygen barrier layer is provided on at least a portion of the surface of the support.

[0052] In addition, the light source unit according to the present invention is characterized by

[15] comprising: a light source; and the particulate color conversion material described in any one of [1] to [5] above or the color conversion member described in any one of [6] to

[14] above.

[0053] In addition, the light source unit according to the present invention is characterized in that,

[16] in the invention described in

[15] above, the light source is a light emitting diode having a maximum light emission within a wavelength range of not less than 400 nm and not more than 500 nm.

[0054] In addition, the display according to the present invention is characterized in that

[17] it includes the light source unit described in

[15] or

[16] above.

[0055] In addition, the lighting device according to the present invention is characterized in that

[18] includes the light source unit described in

[15] or

[16] .

[0056] In addition, the color conversion substrate according to the present invention is characterized by

[19] containing the particulate color conversion material described in any one of [1] to [5] above or the color conversion member described in any one of [6] to

[14] above.

[0057] Effects of the Invention

[0058] The particulate color conversion material and the color conversion member using the same according to the present invention achieve both high color purity light emission and high durability, and therefore, have the effect of achieving both improved color reproducibility and improved durability. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] [ Figure 1 ] Figure 1 Schematic cross-sectional view showing a first example of a color conversion member according to an embodiment of the present invention.

[0060] [ Figure 2 ] Figure 2 It is a schematic cross-sectional view showing a second example of the color conversion member according to the embodiment of the present invention.

[0061] [ Figure 3 ] Figure 3 Schematic cross-sectional view showing a third example of the color conversion member according to the embodiment of the present invention.

[0062] [ Figure 4 ] Figure 4 Schematic cross-sectional view showing a fourth example of the color conversion member according to the embodiment of the present invention.

[0063] [ Figure 5 ] Figure 5 Schematic cross-sectional view showing a fifth example of the color conversion member according to the embodiment of the present invention.

[0064] [ Figure 6 ] Figure 6 Schematic cross-sectional view showing a sixth example of the color conversion member according to the embodiment of the present invention.

[0065] [ Figure 7 ] Figure 7 Schematic cross-sectional view showing a seventh example of the color conversion member according to the embodiment of the present invention. DETAILED DESCRIPTION

[0066] Hereinafter, preferred embodiments of the particulate color conversion material, color conversion member, and light source unit, display, lighting device, and color conversion substrate including the same according to the present invention will be specifically described. However, the present invention is not limited to the following embodiments and can be implemented with various modifications according to the purpose and application.

[0067] The particulate color conversion material involved in the embodiment of the present invention (hereinafter, sometimes simply referred to as "the particulate color conversion material of the present invention") is a particulate color conversion material having a matrix resin and at least one luminescent material. Specifically, the particulate color conversion material of the present invention is a particulate color conversion material containing at least one luminescent material in a matrix resin. In the particulate color conversion material of the present invention, at least one luminescent material contained in the matrix resin includes an organic luminescent material that emits delayed fluorescence with a half-value width of less than 50 nm. That is, the particulate color conversion material of the present invention has the organic luminescent material at least in the matrix resin. It should be noted that the details of the luminescent material possessed by the particulate color conversion material of the present invention will be described later.

[0068] In addition, the color conversion member according to the embodiment of the present invention (hereinafter, sometimes simply referred to as "the color conversion member of the present invention") includes a support containing the above-mentioned particulate color conversion material. That is, the color conversion member of the present invention includes the particulate color conversion material of the present invention and a support containing the particulate color conversion material.

[0069] Representative structural examples of the particulate color conversion material and the color conversion member according to the embodiment of the present invention include: Figure 1 to Figure 7 Example shown. Figure 1 Schematic cross-sectional view showing a first example of a color conversion member according to an embodiment of the present invention. Figure 2 It is a schematic cross-sectional view showing a second example of the color conversion member according to the embodiment of the present invention. Figure 3 Schematic cross-sectional view showing a third example of the color conversion member according to the embodiment of the present invention. Figure 4 Schematic cross-sectional view showing a fourth example of the color conversion member according to the embodiment of the present invention. Figure 5 Schematic cross-sectional view showing a fifth example of the color conversion member according to the embodiment of the present invention. Figure 6 Schematic cross-sectional view showing a sixth example of the color conversion member according to the embodiment of the present invention. Figure 7Schematic cross-sectional view showing a seventh example of the color conversion member according to the embodiment of the present invention.

[0070] like Figure 1 As shown in the figure, the color conversion member 1A of the first example comprises a particulate color conversion material 2a and a support 3a containing the particulate color conversion material 2a. Figure 1 As shown, a particulate color conversion material 2a is dispersed. The particulate color conversion material 2a is an example of the particulate color conversion material of the present invention, and is a material containing at least one light-emitting material in a matrix resin. Figure 1 In the illustrated structural example, the color conversion member 1A has a single-layer structure in which one kind of particulate color conversion material 2a is contained in a single-layer support 3a in a dispersed state.

[0071] like Figure 2 As shown in FIG. 1 , the color conversion member 1B of the second example includes two kinds of particulate color conversion materials 2a and 2b and a support 3a containing the two kinds of particulate color conversion materials 2a and 2b. Figure 2 As shown, particulate color conversion materials 2a and particulate color conversion materials 2b are dispersed. The particulate color conversion materials 2a and particulate color conversion materials 2b are materials containing at least one luminescent material in a matrix resin. For example, the particulate color conversion materials 2a and particulate color conversion materials 2b have different luminescent properties (color conversion properties) such as different luminescent colors. Figure 2 In the illustrated structural example, the color conversion member 1B has a single-layer structure in which two types of particulate color conversion materials 2a and particulate color conversion materials 2b are contained in a single-layer support 3a in a dispersed state.

[0072] like Figure 3 As shown in FIG. 1 , the color conversion member 1C of the third example includes two kinds of particulate color conversion materials 2a and 2b and two layers of supports 3a and 3b containing the two kinds of particulate color conversion materials 2a and 2b, respectively. In the two layers of supports 3a and 3b, one kind of particulate color conversion material 2a is dispersed in one support 3a, and another kind of particulate color conversion material 2b is dispersed in the other support 3b. It should be noted that the particulate color conversion materials 2a and 2b are the same as those of the color conversion member 1B of the second example described above. Figure 3 In the illustrated structural example, the color conversion member 1C has a laminated structure in which a single-layer support 3a containing a particulate color conversion material 2a in a dispersed state and a single-layer support 3b containing a particulate color conversion material 2b different from the particulate color conversion material 2a in a dispersed state are laminated.

[0073] like Figure 4 As shown in FIG. 1 , the color conversion member 1D of the fourth example includes a particulate color conversion material 2a, a support 3a containing the particulate color conversion material 2a, and an oxygen barrier layer 11 covering at least a portion of the surface of the support 3a. The oxygen barrier layer 11 is a layer having oxygen barrier properties. For example, the oxygen barrier layer 11 may be Figure 4 As shown, the two end surfaces ( Figure 4 The upper surface and the lower surface of the middle support body 3a are formed in a manner. It should be noted that, Figure 4 The particulate color conversion material 2a and the support 3a shown are different from the color conversion member 1A of the first example described above (see Figure 1 )same. Figure 4 In the structural example shown, the color conversion member 1D has Figure 1 The color conversion member 1A of the first example shown similarly has a laminated structure in which the oxygen barrier layers 11 are laminated on both end surfaces in the thickness direction of a support 3a including a particulate color conversion material 2a.

[0074] like Figure 5 As shown in FIG. 1 , the color conversion member 1E of the fifth example includes two kinds of particulate color conversion materials 2a and 2b, a support 3a containing the two kinds of particulate color conversion materials 2a and 2b, and an oxygen barrier layer 11 covering at least a portion of the surface of the support 3a. For example, the oxygen barrier layer 11 may be Figure 5 As shown, the two end surfaces ( Figure 5 The upper surface and the lower surface of the middle support body 3a are formed in a manner. It should be noted that, Figure 5 The particulate color conversion materials 2a, 2b and the support 3a shown in the figure are different from the color conversion member 1B of the second example described above (see Figure 2 )same. Figure 5 In the structural example shown, the color conversion member 1E has Figure 2 The color conversion member 1B of the second example shown similarly has a laminated structure in which the oxygen barrier layers 11 are laminated on both end surfaces in the thickness direction of a support 3a including particulate color conversion materials 2a and 2b.

[0075] like Figure 6 As shown in FIG. 1 , the color conversion member 1F of the sixth example includes two kinds of particulate color conversion materials 2a and 2b, two layers of supports 3a and 3b containing the two kinds of particulate color conversion materials 2a and 2b, respectively, and an oxygen barrier layer 11 covering at least a portion of each surface of the two layers of supports 3a and 3b. For example, the oxygen barrier layer 11 may be Figure 6 As shown, the support 3a containing the particulate color conversion material 2a is covered with one end surface ( Figure 6 The upper surface of the support 3a), and one end surface in the thickness direction of the support 3b containing the particulate color conversion material 2b ( Figure 6 It should be noted that, Figure 6 The laminate of two layers of supports 3a and 3b respectively containing two kinds of particulate color conversion materials 2a and 2b and the color conversion member 1C of the third example described above (see Figure 3 )same. Figure 6 In the structural example shown, the color conversion member 1F has Figure 3 The color conversion member 1C of the third example shown has a laminated structure in which the oxygen barrier layers 11 are laminated on both end surfaces in the thickness direction of the laminated body.

[0076] like Figure 7 As shown in FIG. 1 , the color conversion member 1G of the seventh example includes a particulate color conversion material 2a, a support 3a containing the particulate color conversion material 2a, and an oxygen barrier layer 11 covering the entire surface of the support 3a. For example, the oxygen barrier layer 11 may be Figure 7 As shown, the two end surfaces ( Figure 7 The upper and lower surfaces of the support body 3a and the side surfaces of the support body 3a (the end surfaces in the direction perpendicular to the thickness direction) are formed in the manner of the entire area. It should be noted that, Figure 7 The particulate color conversion material 2a and the support 3a shown are different from the color conversion member 1A of the first example described above (see Figure 1 )same. Figure 7 In the structural example shown, the color conversion member 1G has Figure 1 The color conversion member 1A of the first example shown similarly has a laminated structure in which the oxygen barrier layer 11 is laminated on the entire surface of a support 3a including a particulate color conversion material 2a.

[0077] It should be noted that the color conversion component of the present invention is not limited to the above Figures 1 to 7 For example, the color conversion member of the present invention may be a member containing three or more kinds of particulate color conversion materials in a single-layer support, a member containing two or more kinds of particulate color conversion materials in at least one layer of a multilayer support, or a member having a laminated structure in which three or more layers of supports containing one or more kinds of particulate color conversion materials are laminated. Figure 6 In the case where a multilayer support (for example, support 3a, 3b) is provided between two oxygen barrier layers 11 as in the color conversion member 1F of the sixth example shown in FIG. 1 , an oxygen barrier layer 11 sandwiched between the multilayer supports may be provided. Figure 2 The color conversion member 1B of the second example shown has a single-layer structure or a Figure 3 In the case of the same laminated structure as the color conversion member 1C of the third example shown in FIG. Figure 7 The color conversion member 1G of the seventh example shown in the figure similarly has an oxygen barrier layer 11 on all surfaces of the above-mentioned single-layer structure or the above-mentioned laminated structure. In addition, the color conversion member of the present invention may also have a support body (for example, a support body) containing one or more particulate color conversion materials. Figure 1 to Figure 7 The support bodies 3a and 3b shown in the example in the figure further contain a luminescent material different from the particulate color conversion material. In this case, the luminescent material is preferably contained in a state dispersed in the support body. In addition, between each layer of the laminated structure of the color conversion member of the present invention (for example, Figure 3 Between the support body 3a and the support body 3b shown, Figure 4 An adhesive layer or bonding layer is provided between the support 3a and the oxygen barrier layer 11 shown.

[0078] <Luminescent Materials>

[0079] The particulate color conversion material according to the embodiment of the present invention has at least one luminescent material (eg, organic luminescent material) in a matrix resin. Here, the luminescent material in the present invention refers to a material that emits light of a wavelength different from that of a certain light when irradiated with the light.

[0080] In order to achieve efficient color conversion, the luminescent material preferably exhibits a luminescent property with a high quantum yield. Generally, as the luminescent material, known luminescent materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, and quantum dots can be cited. However, in the present invention, from the perspective of uniformity of dispersion, reduction in usage, and reduction in environmental load, at least an organic luminescent material is used as one or more luminescent materials possessed by the particulate color conversion material. In addition, since the particulate color conversion material involved in the embodiment of the present invention contains at least an organic luminescent material in the matrix resin, it exhibits luminescence with high color purity.

[0081] Among many organic light-emitting materials, the particulate color conversion material involved in the embodiment of the present invention includes an organic light-emitting material that emits delayed fluorescence. Here, the organic light-emitting material that emits delayed fluorescence is explained on pages 87 to 103 of "The Most Advanced Organic EL" (edited by Chiba Ya Andachi and Hiroshi Fujimoto, published by CMC Publishing). In this document, it is explained as follows: By making the energy levels of the singlet excited state and the triplet excited state of the light-emitting material close, the reverse energy transfer from the triplet excited state with a low transition probability to the singlet excited state is generated with high efficiency, resulting in thermally activated delayed fluorescence (TADF). In addition, in this document, Figure 5 The generation mechanism of delayed fluorescence is described in . The light emission of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0082] In addition, it is reported that by aligning the energy level of the singlet excited state of the luminescent material with the energy level of the triplet excited state, the reverse energy transfer from the triplet excited state to the singlet excited state can be accelerated (Nature Photonics volume 14, pp. 643-649 (2020)). In addition, research on compounds with a higher energy level of the triplet excited state than the energy level of the singlet excited state of the luminescent material is also being actively conducted.

[0083] In this specification, an organic light-emitting material that efficiently transitions from a triplet excited state to a singlet excited state and emits fluorescence, including an organic light-emitting material that exhibits thermally activated delayed fluorescence, is referred to as an "organic light-emitting material that emits delayed fluorescence". In addition, hereinafter, this "organic light-emitting material that emits delayed fluorescence" may be referred to simply as a "delayed fluorescence material".

[0084] Generally, fluorescence is emitted from a singlet excited state generated after the luminescent material is excited by light. The triplet excited state of the luminescent material generated by intersystem crossing will be thermally deactivated at room temperature. Therefore, fluorescence will not be emitted from the triplet excited state of the luminescent material. On the other hand, as mentioned above, even if the delayed fluorescent material generates a triplet excited state, it will emit fluorescence after quickly converting to a singlet excited state. Therefore, the triplet excited state that cannot contribute to luminescence in a normal fluorescent luminescent material can also contribute to fluorescent luminescence. Therefore, high-efficiency luminescence can be obtained.

[0085] In addition, usually, the reactivity of the organic light-emitting material in the triplet excited state is high. In addition, in the case where the organic light-emitting material is a light-emitting material other than a delayed fluorescent material, the lifetime of the organic light-emitting material as a triplet excited state is long. Therefore, the organic light-emitting material in the triplet excited state is easy to react with the molecules around it. For example, in the presence of oxygen, oxygen with high reactivity and high mobility becomes the recipient of energy from the organic light-emitting material in the triplet excited state, generating singlet oxygen, thereby becoming the cause of oxidative degradation of the organic light-emitting material. On the other hand, in the absence of oxygen, the molecules around the organic light-emitting material will become the recipients of the above-mentioned energy. That is, even in the absence of oxygen and no singlet oxygen is generated, if the organic light-emitting material in the triplet excited state with high reactivity exists for a long time, the reaction of the organic light-emitting material with the molecules around it will also occur, thereby degrading the organic light-emitting material.

[0086] However, when the organic light-emitting material that becomes a triplet excited state is a delayed fluorescent material, the delayed fluorescent material in the triplet excited state can be quickly converted into a delayed fluorescent material in the singlet excited state. Therefore, the reaction between the delayed fluorescent material in the triplet excited state and the molecules around it is not easy to proceed, and thus, the degradation of the delayed fluorescent material caused by the reaction is not easy to occur, and the excellent durability of the delayed fluorescent material can be shown. That is, in order to show high durability, the reverse intersystem crossing of the delayed fluorescent material from the triplet excited state to the singlet excited state should be faster. For example, the rate constant of the reverse intersystem crossing is preferably 1.0×10 2 s -1 above.

[0087] As a molecular design that makes the energy level of the singlet excited state close to the energy level of the triplet excited state, it is effective to bond the electron donor skeleton to the electron acceptor skeleton in the same molecule. In this way, the HOMO (Highest occupied molecular orbital) orbit and the LUMO (Lowest unoccupied molecular orbital) orbit can be separated in the molecule. The electron donor skeleton and the electron acceptor skeleton can be directly bonded or bonded via a connecting group. As a connecting group in this case, it is preferably a skeleton containing aromatic hydrocarbons.

[0088] As the electron donor skeleton, for example, a skeleton having an amine nitrogen atom can be cited. Among them, preferably a skeleton comprising diarylamine, triarylamine, a skeleton comprising carbazole, a skeleton comprising benzocarbazole, a skeleton comprising indolecarbazole, a skeleton comprising phenoxazine, and a skeleton comprising phenothiazine. Among them, more preferably a skeleton comprising carbazole, a skeleton comprising benzocarbazole, a skeleton comprising indolecarbazole, and a skeleton comprising phenoxazine, and more preferably a skeleton comprising carbazole and a skeleton comprising phenoxazine.

[0089] On the other hand, as an electron acceptor skeleton, generally, a skeleton comprising a substituent with electron withdrawing property (i.e., an electron withdrawing group) can be cited. The so-called electron withdrawing group, also referred to as an electron accepting group, is an atomic group that utilizes an inductive effect and a resonance effect to attract electrons from a substituted atomic group in organic electronic theory. As an electron withdrawing group, a group that takes a positive value as a substituent constant (σp (para)) of Hammett's rule can be cited. The substituent constant (σp (para)) of Hammett's rule can be cited from the fifth edition of the basic revision of the Chemical Handbook (II-380 pages). It should be noted that there are also examples in which phenyl also takes a positive value, but in the present invention, phenyl is not included in the electron withdrawing group.

[0090] Examples of electron withdrawing groups include -F (σp: +0.20), -Cl (σp: +0.28), -Br (σp: +0.30), -I (σp: +0.30), -CO2R 12 (σp: in R 12 +0.45 for ethyl), -CONH2 (σp: +0.38), -COR 12 (σp: in R 12 +0.49 for methyl), -CF3 (σp: +0.51), -SO2R 12 (σp: in R 12 When it is a methyl group, it is +0.69), -NO2 (σp: +0.81), etc. 12 Each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of the above groups include the same substituents as those in the compounds represented by the general formula (2) or (3) described below.

[0091] Among the skeletons comprising electron withdrawing groups, preferably a skeleton comprising a heteroaryl having a partial structure formed by a carbon atom and a nitrogen atom being bonded by a double bond, a skeleton comprising a fluorinated substituent, a skeleton comprising a cyano group, a skeleton comprising a carbonyl group, a skeleton comprising a sulfoxide or a disulfoxide, and a skeleton comprising a phosphine oxide group, etc. Among them, from the viewpoint of the stability of the delayed fluorescent material, a skeleton comprising a heteroaryl having a partial structure formed by a carbon atom and a nitrogen atom being bonded by a double bond, a skeleton comprising a fluorinated substituent, and a skeleton comprising a cyano group are more preferred.

[0092] Among the skeletons of heteroaryl groups having a partial structure formed by double bonds between carbon atoms and nitrogen atoms, specifically, skeletons containing pyridine, pyrimidine, pyrazine, triazine, quinoline, quinoxaline, quinazoline or phenanthroline are preferred. Among them, skeletons containing pyrimidine, triazine, quinoxaline or quinazoline are more preferred, and skeletons containing triazine are further preferred.

[0093] Among the skeletons containing fluorinated substituents, more preferably the skeletons containing fluorinated aryl or fluoroalkyl. As the skeleton containing fluorinated aryl, preferably the fluorinated benzene ring, specifically, more preferably the skeleton containing fluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene or pentafluorobenzene. As the skeleton containing fluoroalkyl, preferably the skeleton containing the benzene ring substituted by trifluoromethyl, among them, more preferably the skeleton containing mono (trifluoromethyl) benzene or bis (trifluoromethyl) benzene.

[0094] Among the skeletons having a cyano group, a skeleton containing cyanobenzene, dicyanobenzene, or tricyanobenzene is more preferred.

[0095] An example of a compound in which the electron donor skeleton and the electron acceptor skeleton are bonded as described above is shown below, but the compound is not particularly limited thereto. It should be noted that the compound shown here is known to emit delayed fluorescence from previous documents.

[0096] [Chemical formula 7]

[0097]

[0098] In addition, as the delayed fluorescent material, in addition to the compound in which the above-mentioned electron donor skeleton and the electron acceptor skeleton are bonded, a compound including a partial structure represented by the following general formula (1) is also preferred.

[0099] [Chemical formula 8]

[0100]

[0101] In the general formula (1), B is a boron atom, N is a nitrogen atom, and C is a carbon atom. n is an integer of 0 to 2. When n is 0, the partial structure represented by the general formula (1) represents a structure in which B and N are directly bonded.

[0102] In the delayed fluorescence material comprising the partial structure represented by the general formula (1), the electron donor nitrogen atom and the electron acceptor boron atom are arranged at close positions in the molecule. Such a delayed fluorescence material is a compound that can separate the HOMO orbit from the LUMO orbit by utilizing the multiple resonance effect. By clearly separating the HOMO orbit from the LUMO orbit of the delayed fluorescence material, the energy level of the singlet excited state of the delayed fluorescence material can be made closer to the energy level of the triplet excited state, thereby making it easy to emit delayed fluorescence. In order to make the energy level of the singlet excited state closer to the energy level of the triplet excited state, the delayed fluorescence material is preferably a compound comprising two or more partial structures represented by the general formula (1) in the molecule.

[0103] In addition, in the delayed fluorescent material, if its π conjugated system is expanded, reverse intersystem crossing occurs more efficiently from the triplet excited state to the singlet excited state. Therefore, it is preferred that the π conjugated system of the delayed fluorescent material is expanded. From such a viewpoint, the delayed fluorescent material is preferably a material containing a compound represented by the following general formula (2) or general formula (3).

[0104] [Chemical formula 9]

[0105]

[0106] In the general formula (2) or (3), ring Za, ring Zb and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 6 to 30 ring carbon atoms.

[0107] In the general formula (2), Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom. 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring. E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O.

[0108] In the general formula (3), E 1 and E 2Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2. 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring. 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring.

[0109] The substituents Ra are each independently selected from hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxyl, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted Substituted carboxyl, substituted or unsubstituted oxycarbonyl, substituted or unsubstituted ester, substituted or unsubstituted carbamoyl, substituted or unsubstituted amide, sulfonyl, substituted or unsubstituted sulfonate, substituted or unsubstituted sulfonamide, substituted or unsubstituted amino, substituted or unsubstituted imino, nitro, substituted or unsubstituted silyl, substituted or unsubstituted siloxane, substituted or unsubstituted borane, substituted or unsubstituted phosphine oxide, and substituents selected from the condensed ring and aliphatic ring formed between adjacent substituents. In addition, the substituent Ra can be further substituted by a substituent selected from them. The substituent that replaces the substituent Ra can be further substituted by a substituent selected from them.

[0110] Furthermore, the compound represented by the general formula (2) or (3) preferably contains two or more partial structures represented by the general formula (1) in the molecule.

[0111] In all the above groups, hydrogen may be deuterium. This also applies to the compounds described below or their partial structures. In addition, in this specification, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms is an aryl group having 6 to 40 carbon atoms including the carbon atoms contained in the substituent substituted on the aryl group. The same applies to other substituents with specified carbon atoms.

[0112] When "substituted or unsubstituted" is described, "unsubstituted" means substitution with a hydrogen atom or a deuterium atom. The same also applies to the case where "substituted or unsubstituted" is described in the compounds or partial structures described below.

[0113] In addition, among all the above-mentioned groups, as the substituent in the case of substitution, there can be mentioned 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 carboxyl group, an oxycarbonyl group, an amide group, a sulfonyl group, a sulfonate group, a sulfonamide group, an amino group, a nitro group, a silyl group, a siloxane group, a borane group or a phosphine oxide group, etc. In addition, these substituents may be further substituted by the above-mentioned substituents.

[0114] The so-called alkyl, for example, represents a saturated aliphatic hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, which may or may not have a substituent. There is no particular restriction on the additional substituent when substituted, and for example, alkyl, halogen, aryl, heteroaryl, etc. can be cited, which is also universal in the following description. In addition, the carbon number of the alkyl is not particularly limited, but from the aspect of the ease of acquisition and the cost, it is preferably in the range of 1 to 20, more preferably in the range of 1 to 8.

[0115] The cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may or may not have a substituent. The number of carbon atoms in the alkyl part is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

[0116] The so-called heterocyclic group refers to an aliphatic ring having atoms other than carbon in the ring, such as a pyran ring, a piperidine ring, a cyclic amide, etc., which may or may not have a substituent. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0117] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, and may or may not have a substituent. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0118] The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, which may or may not have a substituent. The number of carbon atoms in the cycloalkenyl group is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

[0119] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, which may or may not have a substituent. The number of carbon atoms in the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

[0120] The so-called alkoxy group refers to a functional group such as methoxy, ethoxy, propoxy, etc., which is bonded to an aliphatic hydrocarbon group via an ether bond, and the aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20.

[0121] The so-called alkylthio group is a group obtained by replacing the oxygen atom of the ether bond of the alkoxy group with a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20.

[0122] The aryl ether group refers to a functional group such as a phenoxy group to which an aromatic hydrocarbon group is bonded via an ether bond, and the aromatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

[0123] The so-called aryl thioether group is a group obtained by replacing the oxygen atom of the ether bond of the aryl ether group with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

[0124] The aryl group includes, for example, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, triphenylenyl, benzanthryl, The aromatic hydrocarbon groups include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, triphenylene, benzofluoranthenyl, dibenzoanthryl, perylene, spiroenyl, etc. Among them, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, pyrenyl, fluoranthenyl, triphenylene. The aryl group may or may not have a substituent. The number of carbon atoms in the aryl group is not particularly limited, and is preferably in the range of 6 to 40, and more preferably in the range of 6 to 30.

[0125] In addition, the aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, and an anthracenyl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, further preferably a phenyl group, a biphenyl group, and a terphenyl group, and particularly preferably a phenyl group.

[0126] When each substituent is further substituted with an aryl group, the aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, and anthracenyl, more preferably phenyl, biphenyl, terphenyl, and naphthyl, and particularly preferably phenyl.

[0127] The so-called heteroaryl group refers to, for example, a cyclic aromatic group having atoms other than carbon in one or more rings, such as pyridyl, furyl, thienyl, quinolyl, isoquinolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, carbolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, dihydroindenocarbazolyl, benzoquinolyl, acridinyl, dibenzoacridinyl, benzimidazolyl, imidazopyridinyl, benzoxazolyl, benzothiazolyl, and phenanthrolinyl. The so-called naphthyridinyl group refers to any one of 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl and 2,7-naphthyridinyl. The heteroaryl group may or may not have a substituent. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 40, and more preferably in the range of 2 to 30.

[0128] In addition, as the heteroaryl group, pyridyl, furyl, thienyl, quinolyl, pyrimidinyl, triazine, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, phenanthrolinyl are preferred, pyridyl, furyl, thienyl, quinolyl are more preferred, and pyridyl is particularly preferred.

[0129] When each substituent is further substituted by a heteroaryl group, the heteroaryl group is preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazine group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzimidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, a phenanthroline group, more preferably a pyridyl group, a furyl group, a thienyl group, a quinolyl group, and particularly preferably a pyridyl group.

[0130] The so-called halogen refers to an atom selected from fluorine, chlorine, bromine and iodine. In addition, the carbonyl group, carboxyl group, oxycarbonyl group and carbamoyl group may or may not have a substituent. Here, as the substituent, for example, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group and the like can be cited, and these substituents may be further substituted.

[0131] The amino group is a substituted or unsubstituted amino group. As a substituent in the case of substitution, for example, an aryl group, a heteroaryl group, a straight-chain alkyl group, and a branched-chain alkyl group can be cited. As the aryl group and the heteroaryl group, a phenyl group, a naphthyl group, a pyridyl group, and a quinolyl group are preferred. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably in the range of 2 to 50, more preferably in the range of 6 to 40, and particularly preferably in the range of 6 to 30.

[0132] The so-called silyl group, for example, means an alkyl silyl group such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, vinyldimethylsilyl, and an aryl silyl group such as phenyldimethylsilyl, tert-butyldiphenylsilyl, triphenylsilyl, and trinaphthylsilyl. The substituent on silicon may be further substituted. The number of carbon atoms in the silyl group is not particularly limited, but is preferably in the range of 1 to 30.

[0133] The so-called siloxane group, for example, means a silicon compound group formed via an ether bond such as a trimethylsiloxane group. The substituent on the silicon may be further substituted. In addition, the so-called borane group is a substituted or unsubstituted borane group. As the substituent group in the case of substitution, for example, an aryl group, a heteroaryl group, a straight-chain alkyl group, a branched-chain alkyl group, an aryl ether group, an alkoxy group, and a hydroxyl group can be cited. Among them, an aryl group and an aryl ether group are preferred.

[0134] The so-called phosphine oxide group is -P(=O)R 10 R 11 The group represented by phosphine oxide group R 10 R 11 The substituent is selected from the same group as the substituent in the case of substitution described above.

[0135] Examples of the substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms in ring Za, ring Zb and ring Zc include a benzene ring, a naphthalene ring, a phenanthrene ring, Aromatic hydrocarbon rings such as anthracene rings and pyrene rings. Among them, from the viewpoint of ensuring solubility, a benzene ring is preferred. In addition, as a heteroaryl ring having 6 to 30 ring carbon atoms, an aromatic heteroaryl ring structure such as a pyridine ring, a quinoline ring, and a phenanthroline ring can be cited. Among them, from the viewpoint of ease of obtaining raw materials and the difficulty of synthesis, a pyridine ring is preferred.

[0136] In the general formula (2), the substituent Ra is preferably a group having 6 to 40 carbon atoms including the substituent. The substituent Ra is more preferably a substituted or unsubstituted aryl group. Examples of the substituted or unsubstituted aryl group include substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, etc. Among them, substituted or unsubstituted phenyl is more preferred.

[0137] In the general formula (3), the substituent Ra is preferably a group having 6 to 40 carbon atoms, including the substituent. The substituent Ra is more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group.

[0138] Z in the general formula (2) 1 and Z2 The reason for this is that the π-conjugated system of the compound represented by the general formula (2) is efficiently expanded, and reverse intersystem crossing from the triplet excited state to the singlet excited state occurs more efficiently, thereby further improving durability.

[0139] In addition, E in the general formula (2) is preferably a boron atom, and E in the general formula (3) is preferably 1 and E 2 The reason for this is that the π-conjugated system of the compound represented by the general formula (2) or (3) is efficiently expanded, and reverse intersystem crossing from the triplet excited state to the singlet excited state occurs more efficiently, thereby further improving durability.

[0140] In addition, ring Za, ring Zb and ring Zc are preferably benzene rings. This is because the π-conjugated system of the compound represented by general formula (2) or general formula (3) is efficiently expanded, and reverse intersystem crossing occurs more efficiently from the triplet excited state to the singlet excited state, thereby further improving durability.

[0141] The compound represented by the general formula (2) or the general formula (3) is a molecule that can separate the HOMO orbital from the LUMO orbital by utilizing the multiple resonance effect by optimally configuring the electron donor amine nitrogen atom and the electron acceptor boron atom, as described in Adv. Mater., 2016, 28, 2777-2781. From the viewpoint of clearly separating the HOMO orbital from the LUMO orbital and bringing the singlet excited state and the triplet excited state closer to each other so as to facilitate the emission of delayed fluorescence, in the general formula (2), it is preferred that E is a boron atom with strong electron acceptor properties, and Z 1 and Z 2 Both are NRa groups that are strong electron donors.

[0142] In addition, the luminescence spectrum of the compound represented by the general formula (2) or the general formula (3) becomes sharper than that of the compound formed by bonding the electron donor skeleton and the electron acceptor skeleton due to the multiple resonance effect of the compound. Therefore, by making the delayed fluorescence material a compound represented by the general formula (2) or the general formula (3), luminescence with high color purity can be obtained. That is, the compound represented by the general formula (2) or the general formula (3) is conducive to improving the color gamut of the display, and is therefore preferred as a delayed fluorescence material. In addition, the compound represented by the general formula (2) or the general formula (3) has ring Za, ring Zb, and ring Zc around the E atom in the general formula (2) or the general formula (3) where the LUMO orbit mainly exists locally, so that the LUMO orbit can be delocalized from the E atom to each ring. By delocalizing the LUMO orbit, the multiple resonance effect works efficiently, so that luminescence with higher color purity can be obtained. It should be noted that the above-mentioned E atom is an atom of E in the general formula (2), and is an atom of E in the general formula (3).1 and E 2 of each atom.

[0143] In addition, the substituent Ra in the general formula (2) or (3) is more preferably a structure in which it is bonded to at least one of the rings Za, Zb, and Zc. This is because by bonding the substituent Ra to at least one of the rings Za, Zb, and Zc, E in the general formula (2) and E in the general formula (3) are 1 and E 2 The steric protection effect is further enhanced, and the effect of suppressing the decrease in fluorescence quantum yield can be expected to be further improved.

[0144] An example of the compound represented by the general formula (2) or (3) is shown below, but the compound is not particularly limited thereto.

[0145] [Chemical formula 10]

[0146]

[0147] [Chemical formula 11]

[0148]

[0149] The luminous wavelength of the delayed fluorescent material is not particularly limited, but in order to extract the three primary colors of blue, green and red from a blue light source, it is preferably a luminous wavelength of green or red when the delayed fluorescent material is excited by blue light. That is, the delayed fluorescent material preferably exhibits luminescence with a peak wavelength observed in a region of 500 nm to less than 580 nm by using an excitation light with a wavelength in the range of 400 nm to 500 nm, or exhibits luminescence with a peak wavelength observed in a region of 580 nm to 750 nm by using an excitation light with a wavelength in the range of 400 nm to 500 nm.

[0150] Furthermore, in order to expand the color gamut and improve color reproducibility, it is preferred that the overlap of the emission spectra of the respective colors of blue, green, and red be small.

[0151] For example, when using blue light with a wavelength of 400 nm to 500 nm with appropriate excitation energy as excitation light, the luminescence with a peak wavelength observed in a region above 500 nm is used as green luminescence. In this case, the overlap of the luminescence spectrum of the excitation light and the green light becomes smaller, and the color reproducibility is improved, so it is preferred. From the perspective of making this effect greater, the lower limit of the peak wavelength of the luminescence when the luminescent material involved in the embodiment of the present invention exhibits green luminescence is more preferably 510 nm or more, further preferably 515 nm or more, and particularly preferably 520 nm or more.

[0152] In addition, in order to minimize the overlap between the excitation light and the luminescence spectrum of the red light, it is preferred to utilize the luminescence with a peak wavelength observed in a region less than 580 nm as the green luminescence. From the perspective of making this effect greater, the upper limit of the peak wavelength of the luminescence when the luminescent material according to the embodiment of the present invention exhibits green luminescence is more preferably 550 nm or less, further preferably 540 nm or less, and particularly preferably 535 nm or less.

[0153] In addition, when the luminescence with a peak wavelength observed in a region of 500 nm or more and less than 580 nm is used as green luminescence, the luminescence with a peak wavelength observed in a region of 580 nm or more is used as red luminescence. In this case, the overlap of the luminescence spectrum of green light and red light becomes smaller, and the color reproducibility is improved, so it is preferred. From the perspective of making this effect greater, the lower limit of the peak wavelength of luminescence when the luminescent material involved in the embodiment of the present invention presents red luminescence is more preferably more than 620 nm, more preferably more than 630 nm, and particularly preferably more than 635 nm.

[0154] The upper limit of the peak wavelength of red light is near the upper limit of the visible light region, that is, below 750nm, but when it is below 700nm, visibility becomes larger, so it is more preferred. From the perspective of making this effect greater, the upper limit of the peak wavelength when the luminescent material involved in the embodiment of the present invention exhibits red luminescence is further preferably below 680nm, and particularly preferably below 660nm.

[0155] That is, when blue light with a wavelength of 400 nm to 500 nm is used as the excitation light, the peak wavelength of the green light is preferably 500 nm to 580 nm, more preferably 510 nm to 550 nm, further preferably 515 nm to 540 nm, and particularly preferably 520 nm to 530 nm. In addition, the peak wavelength of the red light is preferably 580 nm to 750 nm, more preferably 620 nm to 700 nm, further preferably 630 nm to 680 nm, and particularly preferably 635 nm to 660 nm.

[0156] In addition, in order to reduce the overlap of the emission spectrum and improve the color reproducibility, it is preferred that the half-value width at the peak wavelength of the emission spectrum of each color of blue, green, and red (hereinafter referred to as the "half-value width of the emission spectrum") is small. It is particularly effective to improve the color reproducibility that the half-value width of each emission spectrum of green light and red light is small.

[0157] For example, the half-value width of the emission spectrum of green light is preferably 50 nm or less, more preferably 40 nm or less, further preferably 30 nm or less, and particularly preferably 25 nm or less. The half-value width of the emission spectrum of red light is preferably 80 nm or less, more preferably 60 nm or less, further preferably 50 nm or less, and particularly preferably 40 nm or less.

[0158] The delayed fluorescence material contained in the particulate color conversion material according to the embodiment of the present invention emits delayed fluorescence with a half-value width of 50 nm or less, and thus can achieve high color reproducibility. The so-called "delayed fluorescence with a half-value width of 50 nm or less" means that the half-value width of the emission spectrum of the delayed fluorescence material is 50 nm or less. The half-value width of the emission spectrum of the delayed fluorescence material in the present invention is more preferably 40 nm or less, further preferably 30 nm or less, and particularly preferably 25 nm or less.

[0159] It should be noted that there is no particular restriction on the shape of the luminescence spectrum of the delayed fluorescent material in the present invention. For example, from the perspective of achieving efficient utilization of excitation energy and increasing color purity, the luminescence spectrum of the delayed fluorescent material in the present invention is preferably a single peak. Here, the so-called single peak means the following state: within a certain wavelength region, there is no peak with an intensity of more than 5% of the intensity of the peak with the strongest intensity.

[0160] In addition, when the organic light-emitting material emits green light, the organic light-emitting material passes through an excited state having higher energy than when it emits red light. Therefore, compared with the organic light-emitting material that emits red light, the organic light-emitting material that emits green light (hereinafter, sometimes referred to as the green light-emitting material) is inherently more susceptible to degradation. In contrast, an organic light-emitting material that emits delayed fluorescence, especially a delayed fluorescence material including a compound represented by general formula (2) or general formula (3), can simultaneously achieve high color purity light emission and high durability. Therefore, in order to further improve the durability of the color conversion component, among the one or more light-emitting materials contained in the particulate color conversion material, it is preferred that at least the green light-emitting material (the first light-emitting material) is an organic light-emitting material that emits delayed fluorescence. That is, the delayed fluorescence material preferably emits light with a peak wavelength observed in a region of 500 nm or more and less than 580 nm by using excitation light with a wavelength in the range of 400 nm or more and 500 nm or less.

[0161] <Other luminescent materials>

[0162] In the particulate color conversion material involved in the embodiment of the present invention, as at least one luminescent material contained in the matrix resin, in addition to the above-mentioned delayed fluorescence material, a luminescent material other than an organic luminescent material that emits delayed fluorescence (other luminescent materials) may be further included. As the other luminescent material, for example, inorganic phosphors, fluorescent pigments, fluorescent dyes, quantum dots, and organic luminescent materials that do not emit delayed fluorescence can be cited. The other luminescent material may contain two or more of them. In order to achieve efficient color conversion, as the other luminescent material, it is preferred that the material exhibits luminescent characteristics with high quantum yield. Specifically, quantum dots and organic luminescent materials that do not emit delayed fluorescence are preferred, among which organic luminescent materials that do not emit delayed fluorescence are more preferred.

[0163] Examples of organic light-emitting materials that do not emit delayed fluorescence include naphthalene, anthracene, phenanthrene, pyrene, Preferred examples include compounds having a condensed aromatic ring such as tetracene, tri-o-phenylene, perylene, fluoranthene, fluorene, indene, and the like, and derivatives thereof.

[0164] In addition, as organic light-emitting materials that do not emit delayed fluorescence, for example, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirodisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine and other compounds having a heteroaryl ring, and their derivatives are preferred examples.

[0165] In addition, as organic light-emitting materials that do not emit delayed fluorescence, for example, borane derivatives, stilbene derivatives, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, aldazine derivatives, methylenepyrrole derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, coumarin derivatives, etc. can be cited as preferred examples. As stilbene derivatives, for example, 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene, etc. can be cited. As coumarin derivatives, for example, coumarin 6, coumarin 7, coumarin 153, etc. can be cited.

[0166] Preferred examples of organic light-emitting materials that do not emit delayed fluorescence include azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof.

[0167] In addition, as organic light-emitting materials that do not emit delayed fluorescence, for example, cyanine compounds, xanthene compounds, thioxanthene compounds, etc. can be cited as preferred examples. As cyanine compounds, for example, indocyanine green can be cited. As xanthene compounds and thioxanthene compounds, for example, fluorescein, eosin, rhodamine, etc. can be cited.

[0168] In addition, as organic light-emitting materials that do not emit delayed fluorescence, for example, polyphenylene compounds, naphthalimide derivatives, phthalocyanine derivatives and metal complexes thereof, porphyrin derivatives and metal complexes thereof, oxazine compounds, helicene compounds, etc. are preferred. As oxazine compounds, for example, Nile red, Nile blue, etc. are mentioned.

[0169] In addition, as an organic light-emitting material that does not emit delayed fluorescence, for example, aromatic amine derivatives and organic metal coordination compounds can be cited as preferred examples. As aromatic amine derivatives, for example, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine can be cited. As organic metal coordination compounds, for example, iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os) and rhenium (Re) can be cited.

[0170] An example of the above-mentioned organic light-emitting material is shown below, but the organic light-emitting material is not particularly limited thereto.

[0171] [Chemical formula 12]

[0172]

[0173] In addition, as an organic light-emitting material that does not emit delayed fluorescence, an organic light-emitting material including a partial structure represented by the above-mentioned general formula (1) is also preferable from the viewpoint of obtaining light emission with high color purity.

[0174] The above-mentioned organic light-emitting material that does not emit delayed fluorescence can be a fluorescent light-emitting material or a phosphorescent light-emitting material, but in order to achieve high color purity, it is preferably a fluorescent light-emitting material. Among them, from the perspective of imparting a high fluorescence quantum yield and better durability of chromaticity, it is preferred to use a pyrrole derivative. Among the pyrrole derivatives, a boron complex of pyrrole is preferred. As a boron complex of pyrrole, a compound represented by the general formula (4) described later can be cited as a preferred example.

[0175] Furthermore, in order to improve the efficiency of energy transfer from the excitation light to the delayed fluorescent material, the particulate color conversion material according to the embodiment of the present invention may further contain an auxiliary dopant such as rubrene.

[0176] The content of the luminescent material in the particulate color conversion material of the present invention depends on the molar absorption coefficient, luminescent quantum yield and absorption intensity at the excitation wavelength of the compound, as well as the size, thickness and transmittance of the prepared particulate color conversion material and color conversion member, but is usually preferably 1.0×10 -4In addition, the content of the luminescent material is more preferably 1.0×10 -3 Parts by weight or more and 10 parts by weight or less, particularly preferably 5.0×10 -3 More than 5 parts by weight.

[0177] <Matrix resin>

[0178] The particulate color conversion material according to the embodiment of the present invention is provided with a matrix resin containing at least one of the above-mentioned luminescent materials. In the particulate color conversion material, as the matrix resin, it is preferred to use a material having excellent molding processability, transparency, heat resistance, etc. As examples of such a matrix resin, for example, photocurable resist materials having reactive vinyl groups such as acrylic acid, methacrylic acid, polyvinyl cinnamate, and cyclorubber, epoxy resins, silicone resins (including organic polysiloxane 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, etc., can be cited. In addition, as the matrix resin, a mixture or copolymer of these resins can also be used. By appropriately designing these resins, a matrix resin useful for the particulate color conversion material of the color conversion member of the present invention can be obtained.

[0179] Among these resins, from the viewpoint of transparency and dispersibility of the organic light-emitting material, the matrix resin is preferably any one of acrylic resin, copolymer resin containing acrylate or methacrylate moiety, polyester resin, cycloolefin resin, epoxy resin, and silicone resin. In addition, from the viewpoint of heat resistance, a thermosetting resin or a photocurable resin can be preferably used as the matrix resin.

[0180] In addition, the glass transition temperature (Tg) of the matrix resin is not particularly limited, but is preferably 30°C to 180°C. When the Tg of the matrix resin is 30°C or higher, the molecular movement of the matrix resin caused by the heat generated by the incident light from the light source and the driving heat of the device can be suppressed, thereby suppressing the change in the dispersion state of the light-emitting material in the matrix resin, thereby preventing the durability of the particulate color conversion material from deteriorating. In addition, when the Tg of the matrix resin is 180°C or lower, the flexibility of the matrix resin when molded into a sheet or the like can be ensured. The Tg of the matrix resin is more preferably 50°C to 170°C, further preferably 70°C to 160°C, and particularly preferably 90°C to 150°C.

[0181] In addition, the molecular weight of the matrix resin also depends on the type of resin used, so it is not particularly limited, and is preferably 3000 to 1500000. When the molecular weight is less than 3000, the matrix resin becomes brittle, and the flexibility of the matrix resin when it is molded becomes low. In addition, when the molecular weight is greater than 1500000, there are problems such as excessive viscosity of the matrix resin during molding and reduced chemical stability of the matrix resin itself. The molecular weight of the matrix resin is more preferably 5000 to 1200000, further preferably 7000 to 1000000, and particularly preferably 10000 to 800000.

[0182] <Additives>

[0183] The particulate color conversion material according to the embodiment of the present invention may contain additives as other components in addition to the above-mentioned at least one luminescent material and the matrix resin. Examples of the additives include light stabilizers, antioxidants, processing and heat stabilizers, light resistance stabilizers such as ultraviolet absorbers, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, inorganic particles such as silica particles and organosilicon microparticles, and silane coupling agents.

[0184] As the light stabilizer, for example, tertiary amines, catechol derivatives, and at least one transition metal selected from the group consisting of Ni, Sc, V, Mn, Fe, Co, Cu, Y, Zr, Mo, Ag and lanthanoids, complexes or salts with organic acids, etc. can be cited, but there are no particular limitations. In addition, these light stabilizers can be used alone or in combination of multiple types.

[0185] Examples of the antioxidant include, but are not particularly limited to, phenolic antioxidants such as 2,6-di-tert-butyl-p-cresol and 2,6-di-tert-butyl-4-ethylphenol. These antioxidants may be used alone or in combination of two or more.

[0186] As processing and heat stabilizers, for example, phosphorus stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine can be cited, but are not particularly limited thereto. In addition, these stabilizers can be used alone or in combination of multiple types.

[0187] Examples of the light resistance stabilizer include benzotriazoles such as 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, but are not particularly limited thereto. These light resistance stabilizers may be used alone or in combination of two or more.

[0188] As scattering particles, for example, inorganic particles having a refractive index of 1.7 to 2.8 are preferred. Examples of the inorganic particles include titanium dioxide, zirconium oxide, aluminum oxide, cerium dioxide, tin oxide, indium oxide, iron oxide, zinc oxide, aluminum nitride, aluminum, tin, titanium or zirconium sulfide, titanium or zirconium hydroxide, and the like.

[0189] The content of these additives in the particulate color conversion material according to the embodiment of the present invention depends on the molar absorption coefficient, luminescence quantum yield and absorption intensity at the excitation wavelength of the compound, as well as the size, thickness and transmittance of the prepared particulate color conversion material and color conversion member, but is preferably 1.0×10 -3 parts by weight or more, more preferably 1.0×10 -2 Parts by weight or more, particularly preferably 1.0×10 -1 Furthermore, the content 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, based on 100 parts by weight of the base resin.

[0190] <Color conversion material in granular form>

[0191] As described above, the particulate color conversion material of the present invention is a particulate color conversion material containing at least one luminescent material in a matrix resin, and can be handled as a powder. Therefore, by mixing a plurality of particulate color conversion materials for use, it is easy to finely adjust the wavelength conversion characteristics. For example, in the case of converting the color of a portion of blue light to obtain white light, a green conversion material containing a luminescent material that emits green light and a red conversion material containing a luminescent material that emits red light are prepared as particulate color conversion materials, and the mixing amount thereof is adjusted, thereby making it easy to adjust the white balance and color temperature of the white light.

[0192] Furthermore, by controlling the particle size, shape, and refractive index of the matrix resin of the particulate color conversion material, the color conversion characteristics of the particulate color conversion material can be adjusted, and functions other than color conversion can be imparted to the particulate color conversion material, such as light scattering.

[0193] In the particulate color conversion material of the present invention, each particle of the color conversion material is independent of each other. Therefore, when highly active species such as free radical species are generated in a particle group of the particulate color conversion material or a color conversion component using the particulate color conversion material due to light irradiation under high temperature conditions, the highly active species can be suppressed from propagating to the entire particle group. As a result, the accelerated degradation of the particle group of the particulate color conversion material or the entire color conversion component using the particulate color conversion material can be suppressed.

[0194] In addition, in the particulate color conversion material of the present invention, at least the above-mentioned delayed fluorescent material is used as one or more luminescent materials contained in the matrix resin. Therefore, the durability of the particulate color conversion material and the color conversion member using the same can be further improved, and the high color purity and high durability of the particulate color conversion material and the color conversion member using the same can be achieved at the same time. Generally, in the particulate color conversion material and the color conversion member using the same, there are more interfaces compared to the state of the continuous phase such as a film, so it is easy to increase the number of excitations of the luminescent material due to reflection at the interface. This is caused by the following reasons: a part of the luminescence of the luminescent material encapsulated in the particulate color conversion material is reflected at the interface between the inside and outside of the particle of the particulate color conversion material, so that the luminescent material inside the particle is excited again. The increase in the number of excitations leads to an increase in the number of organic luminescent materials in the triplet excited state, an increase in the probability of generating highly active chemical species such as singlet oxygen generated by energy transfer from the organic luminescent material in the triplet excited state, and an increase in the chance of these active species reacting with surrounding molecules, thereby promoting the degradation and decomposition of the organic luminescent material in the particulate color conversion material. In contrast, the delayed fluorescent material can rapidly convert the triplet excited state into the singlet excited state as described above, and therefore is less likely to deteriorate even if the number of excitations increases due to reflection at the interface, and can exhibit excellent durability.

[0195] The average particle size of the particulate color conversion material of the present invention is preferably 0.0010 μm to 100 μm, more preferably 0.010 μm to 30 μm, and particularly preferably 0.010 μm to 10 μm. The average particle size of the particulate color conversion material can be obtained by measuring the particle size distribution by microscopic observation or laser diffraction scattering method, but in principle, it is obtained from the measurement result of the particle size distribution based on microscopic observation. Among them, when the particle size of 1 μm or less is obtained from the measurement result of the particle size distribution based on the laser diffraction scattering method, the particle size based on the laser diffraction scattering method is used as the average particle size of the particulate color conversion material. In addition, in the case of measuring the particle size distribution based on microscopic observation, there is no particular limitation. For example, the particle size of about 100 independent particles in the powder of the particulate color conversion material can be measured and the average value thereof can be calculated to obtain the average particle size of the particulate color conversion material.

[0196] The shape of the particulate color conversion material of the present invention is not particularly limited, and for example, it can be as described above. Figures 1 to 7The particulate color conversion materials 2a and 2b shown in the figure may be spherical, or may be ellipsoidal or other shapes other than spherical. The shape of the particulate color conversion material of the present invention is preferably a shape with high sphericity. By making the sphericity of the particulate color conversion material high, the optical loss caused by undesired light scattering on the particle surface of the particulate color conversion material and multiple reflections inside the particles can be reduced. In addition, the degradation of the luminescent material (e.g., the organic luminescent material in the particulate color conversion material) caused by multiple excitations can be suppressed.

[0197] <Method for producing a particle-shaped color conversion material>

[0198] The method for producing the particulate color conversion material according to the embodiment of the present invention is not particularly limited as long as it is a method that can mold a matrix resin containing at least one luminescent material into a particulate form. For example, the particulate color conversion material can be produced by methods such as interfacial polymerization, W / O liquid drying, Stober method, spray drying, in-situ polymerization, phase separation from an aqueous solution, phase separation from an organic solvent, melt dispersion cooling, and gas suspension coating.

[0199] Among them, as a simple method for preparing a particulate color conversion material, the following method can be cited: a composition prepared by mixing a predetermined amount of the aforementioned luminescent material, a matrix resin, and a solvent is dried by a spray drying method to form a particulate shape. From the viewpoint that the shape of the obtained particles is close to a sphere, as a preferred method for preparing a particulate color conversion material, the following method can be cited: a method in which a composition prepared by mixing a predetermined amount of the aforementioned luminescent material, a matrix resin, and an organic solvent is made into a W / O emulsion, and then dried by a W / O liquid drying method to form a particulate shape; a method in which a composition prepared by mixing a predetermined amount of the aforementioned luminescent material, a raw material monomer forming a matrix resin, and a solvent is polymerized by an in-situ polymerization method, especially an emulsion polymerization method in which a surfactant is used to react in a state where the composition is made into a W / O emulsion, and then formed into a particulate shape.

[0200] In addition, when a particulate color conversion material is produced by a W / O liquid drying method, the following method can also be cited as a preferred method for producing the particulate color conversion material: a method in which the heat resistance of the particles is improved by cross-linking and curing the matrix resin at any stage in the W / O emulsion state of the above-mentioned composition, or in the particulate state during or after the removal of the organic solvent from the above-mentioned composition.

[0201] As the solvent, for example, water, 2-propanol, ethanol, toluene, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, cyclohexane, tetrahydrofuran, acetone, terpineol, TEXANOL, 1,2-dimethoxyethane, methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1-methoxy-2-propanol, propylene glycol monomethyl ether acetate, etc. can be cited. It is also possible to mix two or more of these solvents and use them. Among these solvents, toluene, methyl ethyl ketone, methyl acetate, ethyl acetate, and tetrahydrofuran are preferably used from the aspect of less residual solvent after drying.

[0202] <Support>

[0203] The particulate color conversion material of the present invention can be used only by itself (i.e., in the form of particles). In addition, from the viewpoint of further improving the applicability to optical components, the particulate color conversion material of the present invention is preferably used in the form of being contained in a support. The support containing the particulate color conversion material of the present invention can be, for example, Figures 1 to 7 As shown, it is used as the color conversion member of the present invention.

[0204] There is no particular limitation on the material of the support, and known metals, resins, glass, ceramics, paper, etc. can be used. However, from the viewpoint of transparency and processability, the support is preferably obtained from a resin. In the case where the support is obtained from a resin, it is more preferred that the particulate color conversion material is dispersed in the support. In the present invention, dispersion means that other substances are dispersed in a substance that forms one phase, and the distribution may be uneven or uniform. However, when it is described as dispersing the particulate color conversion material, it does not include a method in which the particulate color conversion material is completely dissolved in the dispersion medium to form a uniform phase. In order to confirm whether the particulate color conversion material of the present invention is dispersed in the support, methods such as naked eye observation, microscopic observation, emission spectroscopy measurement, and refractive index measurement can be appropriately adopted. As a preferred resin for the support, for example, the resins exemplified in the above-mentioned matrix resin can be cited.

[0205] When the support is obtained from a resin, the difference in SP value between the matrix resin of the particulate color conversion material and the resin forming the support is preferably 0.5 (cal / cm 3 ) 0.5 By making the difference in SP value 0.5 (cal / cm 3 ) 0.5 The above-mentioned method can disperse the particulate color conversion material in the support without dissolving it. The difference in the SP value is more preferably 1.0 (cal / cm 3 ) 0.5 More preferably, 1.5 (cal / cm3 ) 0.5 Above, particularly preferably 2.0 (cal / cm 3 ) 0.5 In addition, if the difference in the SP value is too large, the particles will aggregate and become the cause of extinction. Therefore, the upper limit of the difference in the SP value is more preferably 4.0 (cal / cm 3 ) 0.5 Below, more preferably 3.0 (cal / cm 3 ) 0.5 Below, particularly preferably 2.5 (cal / cm 3 ) 0.5 the following.

[0206] Furthermore, when the support is obtained from a resin, the SP value of the matrix resin of the particulate color conversion material is preferably larger than the SP value of the resin forming the support.

[0207] The properties of the support are not particularly limited, and examples include supports in liquid, gel, and solid states. The shape of the support is not particularly limited, and examples include granular, block, and sheet shapes. In addition, the shape of the support may be a form filled in a mold. Among them, from the viewpoint of further improving the applicability to the light source unit described later, the shape of the support is preferably sheet-shaped.

[0208] On the other hand, from the viewpoint of integration with an LED light source and integration with a patterned member, a method of filling the support body into a mold is also preferred as a method of forming the support body.

[0209] The particulate color conversion material contained in the support may be one kind or two or more kinds.

[0210] As one embodiment of the color conversion member of the present invention, it is preferred that at least two kinds of particulate color conversion materials are contained in the same support: a particulate color conversion material containing a first luminescent material (green luminescent material) that emits green light (hereinafter referred to as the first particulate color conversion material); and a particulate color conversion material containing a second luminescent material (red luminescent material) that emits red light (hereinafter referred to as the second particulate color conversion material). Thus, the color conversion member of the present invention can convert the color of a part of blue light to obtain white light.

[0211] That is, with respect to the color conversion component of the present invention, it is preferred that the color conversion component comprises the above-mentioned particulate color conversion material and a support body, wherein the particulate color conversion material comprises: a first particulate color conversion material formed by a first light-emitting material exhibiting light emission with a peak wavelength observed in a region of not less than 500 nm and not more than 580 nm and a first matrix resin; and a second particulate color conversion material formed by a second light-emitting material exhibiting light emission with a peak wavelength observed in a region of not less than 580 nm and not more than 750 nm and a second matrix resin.

[0212] In the present invention, it is more preferable that the first luminescent material of the first particulate color conversion material contains at least an organic luminescent material (delayed fluorescent material) that emits delayed fluorescence with a half-value width of 50 nm or less. As described above, by making the green luminescent material (i.e., the first luminescent material) that passes through an excited state with high energy a material containing the delayed fluorescent material or the delayed fluorescent material itself, the durability of the color conversion member can be further improved.

[0213] On the other hand, in the present invention, the second light-emitting material of the second particulate color conversion material preferably contains at least one of a compound including a partial structure represented by the above general formula (1), a compound represented by general formula (2), and a compound represented by general formula (3).

[0214] In the present invention, from the viewpoint of obtaining light emission with high color purity, it is also preferred that the second light emitting material of the second particulate color conversion material contains at least a compound represented by the general formula (4) described later.

[0215] As another embodiment of the color conversion member of the present invention, a color conversion member composed of a plurality of supports containing particulate color conversion materials is also preferred. For example, as a color conversion member of this other embodiment, a color conversion member composed of a support containing a first particulate color conversion material that emits green light and a support containing a second particulate color conversion material that emits red light can be cited. That is, as a preferred embodiment of the present invention, a color conversion member can be cited that includes a first support having a first particulate color conversion material formed of a first luminescent material that emits light with a peak wavelength observed in a region of 500 nm or more and less than 580 nm and a first matrix resin, and a second support having a second particulate color conversion material formed of a second luminescent material that emits light with a peak wavelength observed in a region of 580 nm or more and less than 750 nm and a second matrix resin. As a method of combining a plurality of supports, although it also depends on the shape of each support to be combined, a method of arranging on the same plane, a method of laminating, etc. can be cited.

[0216] As these first luminescent material and second luminescent material, there is no particular limitation, and known luminescent materials such as inorganic phosphors, fluorescent pigments, fluorescent dyes, quantum dots, etc. can be cited. In particular, from the aspect of being able to obtain white light with high color reproducibility, as the first luminescent material and the second luminescent material, organic luminescent materials are preferred.

[0217] By optimizing the combination of the organic light-emitting material and the matrix resin in each of the first particulate color conversion material and the second particulate color conversion material, the light emission peak wavelength of the organic light-emitting material can be shifted to a desired wavelength, thereby expanding the color gamut. That is, the first matrix resin of the first particulate color conversion material and the second matrix resin of the second particulate color conversion material can be the same resin or different resins. It should be noted that the two matrix resins are different from each other, which means that the composition of the resin is different.

[0218] In addition, the SP value, which is a dissolution parameter of the matrix resin, has a strong correlation with the peak wavelength of the luminescence of the organic light-emitting material. In a matrix resin with a large SP value, the excited state of the organic light-emitting material is stabilized due to the interaction between the matrix resin and the organic light-emitting material. Therefore, compared with a matrix resin with a small SP value, the peak wavelength of the luminescence of the organic light-emitting material is shifted to the long wavelength side. Therefore, by dispersing the organic light-emitting material in a matrix resin with an optimal SP value, the peak wavelength of the luminescence of the organic light-emitting material can be optimized.

[0219] For example, when the SP value of the first matrix resin is SP A (cal / cm 3 ) 0.5 The SP value of the second matrix resin is set as SP B (cal / cm 3 ) 0.5 When SP A ≤SP B In this case, the difference between the emission peak wavelengths of green light and red light in the first particulate color conversion material and the second particulate color conversion material becomes larger than when the organic light emitting materials are dispersed in the same matrix resin, resulting in an expanded color gamut.

[0220] Among them, SP is preferred B ≥9.5. SP B The larger the value of , the longer the peak wavelength of the red light in the second particulate color conversion material becomes, and as a result, deep red light can be emitted from the second particulate color conversion material. From the viewpoint of making this effect greater, it is more preferable to B ≥10.0.

[0221] SP BThere is no particular upper limit on the value of SP B The matrix resin with a ratio of ≤15.0 has good dispersibility in the organic light-emitting material and can be preferably used. From the viewpoint of making this effect greater, SP B ≤14.0, further preferred SP B ≤13.0, especially preferred SP B ≤12.0.

[0222] In addition, in SP A When ≤11.0, the peak wavelength of green light in the first particulate color conversion material can be suppressed from being increased, and as a result, the difference between the peak wavelengths of green light and red light in the first particulate color conversion material and the second particulate color conversion material becomes larger. A ≤11.0. From the viewpoint of making this effect greater, SP A ≤10.5, further preferred SP A ≤10.0.

[0223] SP A There is no particular lower limit, but A The matrix resin with a value of ≥7.0 has good dispersibility in the organic light-emitting material and can be preferably used. From the viewpoint of making this effect greater, SP A ≥7.4, further preferred SP A ≥7.8, especially preferred SP A ≥8.0.

[0224] Here, the solubility parameter (SP value) is a value generally used and calculated from the types and ratios of monomers constituting the resin using the Fedors method described in Poly. Eng. Sci., vol. 14, No. 2, pp. 147-154 (1974), etc. The SP value of a mixture of multiple resins can also be calculated by the same method. For example, the SP value of polymethyl methacrylate can be calculated to be 9.9 (cal / cm 3 ) 0.5 , it can be calculated that the SP value of polyethylene terephthalate (PET) is 11.6 (cal / cm 3 ) 0.5 , it can be calculated that the SP value of bisphenol A epoxy resin is 10.9 (cal / cm 3 ) 0.5 .

[0225] Typical SP values ​​of the resins are shown in Table 1. The first matrix resin and the second matrix resin described above can be arbitrarily used in combination from among the resins shown in Table 1, for example.

[0226] [Table 1]

[0227] (Table 1)

[0228]

[0229] As another embodiment of the color conversion member of the present invention, it is also preferred that the support of the color conversion member contains at least one luminescent material in addition to the particulate color conversion material of the present invention. Among them, from the viewpoint of color purity, the support of the color conversion member more preferably contains at least one organic luminescent material, and particularly preferably contains at least one of a compound containing a partial structure represented by the above-mentioned general formula (1), a compound represented by the general formula (2), and a compound represented by the general formula (3). In addition, from the viewpoint of obtaining luminescence with high color purity, it is also preferred that the support of the color conversion member contains at least a compound represented by the general formula (4) as one of the above-mentioned luminescent materials.

[0230] [Chemical formula 13]

[0231]

[0232] In the general formula (4), X is CR 7 or N. R 1 ~R 9 Each of them may be the same or different, and is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxyl, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and a condensed ring and aliphatic ring formed with adjacent substituents. R 1 ~R 9 Each independently may be substituted. 1 ~R 9 The substituents for each substitution are selected from the same group as the substituent Ra in the above-mentioned general formula (2) or (3).

[0233] From the viewpoint of photostability, X in the general formula (4) is preferably CR 7 In addition, from the viewpoint of providing a higher fluorescence quantum yield and being less likely to undergo thermal decomposition and from the viewpoint of photostability, it is preferred that X in the general formula (4) is CR 7 , and R 7 The aryl group is preferably a substituted or unsubstituted aryl group, and is more preferably a substituted or unsubstituted phenyl group, from the viewpoint of not impairing the emission wavelength.

[0234] In the general formula (4), R 8and R 9 Preferably, R is fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group, or a cyano group. In particular, R is stable with respect to the excitation light and can obtain a higher fluorescence quantum yield. 8 and R 9 More preferred is fluorine or cyano.

[0235] As a first preferred example of the compound represented by the general formula (4), the following can be mentioned: 1 , R 3 , R 4 and R 6 All of them may be the same or different and are substituted or unsubstituted phenyl. In addition, X is CR 7 , and R 7 is a substituted or unsubstituted phenyl group. In this case, R is particularly preferably 1 , R 3 , R 4 , R 6 and R 7 At least one of them is a phenyl group substituted by a methoxy group.

[0236] As a second preferred example of the compound represented by the general formula (4), the following can be mentioned: 1 , R 3 , R 4 and R 6 All of them may be the same or different and are substituted or unsubstituted alkyl groups. In addition, X is CR 7 , and R 7 is a substituted or unsubstituted phenyl group. In this case, R 2 and R 5 They may be the same or different, and are particularly preferably substituted or unsubstituted ester groups.

[0237] As a third preferred example of the compound represented by the general formula (4), R 1 With R 2 , R 2 With R 3 , R 4 With R 5 , and R 5 With R 6At least one of the four groups is a ring structure of any one of the following general formulae (5A) to (5D). Each ring structure represented by each of the general formulae (5A) to (5D) has a double bond. Therefore, by introducing any of the ring structures into the above-mentioned compound, the conjugation can be expanded, thereby achieving a long wavelength of luminescence. In addition, by introducing the ring structure into the above-mentioned compound, the double bond site can be fixed to the central skeleton by chemical bonds, thereby suppressing excessive structural relaxation in the excited state and obtaining luminescence with good color purity. In this third example, as a preferred example, the following cases can be cited: R 2 and R 3 is a ring structure represented by the general formula (5D), wherein Ar in the general formula (5D) is a substituted or unsubstituted benzene ring, and R in the general formula (5D) is 101 and R 102 Each of them may be the same or different, and is a substituted or unsubstituted alkyl or a substituted or unsubstituted phenyl, and X is CR 7 , and R 7 is a substituted or unsubstituted phenyl group. In this case, R 4 and R 6 Each of them may be the same or different, and is more preferably a substituted or unsubstituted phenyl group. 101 With R 102 In the general formulas (5A) to (5D), R 101 , R 102 and R 201 ~R 204 R in the above general formula (4) 1 ~R 7 Synonymous.

[0238] [Chemical formula 14]

[0239]

[0240] As another aspect of the color conversion member of the present invention, it is also preferred that the support of the color conversion member has oxygen barrier properties. The so-called oxygen barrier properties refer to the property of low oxygen permeability. In the present invention, the oxygen permeability of the support is preferably 1.0 cc / m 2 ·day·atm or less, more preferably 0.5cc / m 2 ·day·atm or less, particularly preferably 0.1cc / m 2 ·day·atm or less.

[0241] It should be noted that the oxygen permeability is a value measured using a flat test piece with uniform film thickness, at a temperature of 20° C. and a humidity of 0% RH, using an oxygen permeability measuring device (model name: “OXTRAN” (registered trademark) (“OXTRAN” 2 / 20)) manufactured by MOCON (USA) in accordance with the electrolytic sensor method described in JIS K7126-2 (2006), unless otherwise specified.

[0242] As described above, in the absence of oxygen, the reaction of the highly reactive triplet excited state organic light-emitting material with the surrounding molecules will become the main cause of the degradation of the organic light-emitting material. However, in the case where the organic light-emitting material in the triplet excited state is a delayed fluorescent material, the delayed fluorescent material in the triplet excited state can be quickly converted into a delayed fluorescent material in the singlet excited state. Therefore, in the absence of oxygen, the delayed fluorescent material shows much better durability than the conventional organic light-emitting material (organic light-emitting material that does not emit delayed fluorescence).

[0243] In addition, as another embodiment of the color conversion member of the present invention, it is also preferable that the color conversion member is, for example, Figures 4 to 7 As shown in the figure, at least a portion of the surface of the support has an oxygen barrier layer (i.e., an oxygen barrier layer). When the oxygen barrier layer blocks the permeation of oxygen into the support, as described above, the delayed fluorescent material can show much better durability than the conventional organic light-emitting materials. In the present invention, the oxygen permeability of the oxygen barrier layer is preferably 2.0 cc / m 2 ·day·atm or less, more preferably 1.0cc / m 2 ·day·atm or less, more preferably 0.5cc / m 2 ·day·atm or less, particularly preferably 0.1cc / m 2 ·day·atm or less.

[0244] In addition, as the above-mentioned oxygen barrier layer, a glass layer, an inorganic oxide layer, an inorganic nitride layer, a resin layer, etc. can be cited. As the inorganic oxide constituting the above-mentioned oxygen barrier layer, silicon oxide and aluminum oxide are preferred from the viewpoint of cost, among which aluminum oxide can be particularly preferably used. As for the resin layer as an example of the above-mentioned oxygen barrier layer, from the viewpoint of the height of oxygen barrier property, a layer formed of a polyol-based resin is more preferred, among which a layer formed of a saponified product of vinyl acetate such as polyvinyl alcohol, an ethylene-vinyl alcohol copolymer, and a mixture containing these resins is particularly excellent in oxygen barrier property, and is therefore further more preferred.

[0245] As another embodiment of the color conversion member of the present invention, a color conversion member in which a support containing a particulate color conversion material has oxygen barrier properties and at least a portion of the surface of the support is covered with the above-mentioned oxygen barrier layer can also obtain higher oxygen barrier properties, so it is preferred. For example, as a configuration of the color conversion member in this other embodiment, an oxygen barrier layer such as a barrier film is stacked on both sides of a layer (color conversion layer) of the color conversion member obtained from the particulate color conversion material of the present invention and the support having oxygen barrier properties. In this case, the oxygen barrier property of the support can be used to prevent oxygen from invading the end of the entire surface of the support that is not covered by the barrier film, and the degradation of the particulate color conversion material in the end can be suppressed.

[0246] The support that can be used for the color conversion member of the present invention may contain additives as required in addition to the above-mentioned particulate color conversion material and luminescent material. Examples of such additives include light absorbing pigments, light absorbing pigments, antioxidants, processing and heat stabilizers, light resistance stabilizers such as ultraviolet absorbers, dispersants, leveling agents, plasticizers, crosslinking agents such as epoxy compounds, curing agents such as amines, acid anhydrides, and imidazoles, adhesion aids, inorganic particles such as titanium oxide particles, zirconium oxide particles, and silicon dioxide particles, and silane coupling agents.

[0247] <Method for producing color conversion member>

[0248] The method for producing the color conversion member according to the embodiment of the present invention is not particularly limited as long as it is a method that can shape the support body containing the particulate color conversion material of the present invention into a desired shape. For example, the following method can be cited: the particulate color conversion material of the present invention, the resin that becomes the support body, and the solvent are mixed to produce a composition, and then the composition is applied to a substrate and dried, thereby forming the support body containing the particulate color conversion material of the present invention into a sheet. In addition, the following method can also be cited: the particulate color conversion material of the present invention and the resin that becomes the support body are mixed while being heated, and the molding is performed using an extruder.

[0249] <Color conversion substrate>

[0250] The color conversion substrate according to the embodiment of the present invention (hereinafter, sometimes simply referred to as "the color conversion substrate of the present invention") is configured to include at least the particulate color conversion material of the present invention or the color conversion member of the present invention. For example, the color conversion substrate of the present invention includes a plurality of color conversion layers on a transparent substrate. In the present invention, the color conversion layer preferably includes a red conversion layer and a green conversion layer. The red conversion layer is formed of a fluorescent material that absorbs at least blue light and emits red light. The green conversion layer is formed of a fluorescent material that absorbs at least blue light and emits green light. In addition, a partition wall may be formed on the color conversion substrate of the present invention, and the color conversion layer is preferably arranged between the partition walls (recessed portion). The color conversion substrate of the present invention may be a substrate in which excitation light is incident from the transparent substrate side and light is observed from the side opposite to the transparent substrate, or may be a substrate in which excitation light is incident from the color conversion layer side and light is observed from the transparent substrate side. When blue light having a peak wavelength of 440 nm or more and 460 nm or less is irradiated to the color conversion substrate, the quantum yield of the color conversion layer is generally 0.5 or more, preferably 0.7 or more, more preferably 0.8 or more, and particularly preferably 0.9 or more.

[0251] <Ink>

[0252] The particulate color conversion material or color conversion member of the present invention can also be used in ink. The ink according to the embodiment of the present invention (hereinafter, sometimes referred to as "the ink of the present invention") is composed of a liquid, gel or solid state containing at least the particulate color conversion material or color conversion member of the present invention, and can be used for recording text, etc., and coloring the surface. The ink of the present invention can achieve both high color purity luminescence and high durability by using the particulate color conversion material or color conversion member of the present invention, and therefore, it can be preferably used as a fluorescent ink for security printing purposes.

[0253] <Light source unit>

[0254] The light source unit according to the embodiment of the present invention (hereinafter, sometimes referred to as "the light source unit of the present invention") is configured to include at least a light source and the above-mentioned particulate color conversion material or color conversion member. In the light source unit of the present invention, there is no particular limitation on the configuration method of the light source and the particulate color conversion material or color conversion member. The light source and the particulate color conversion material or color conversion member may be closely attached to each other, or may be a remote phosphor in which the light source and the particulate color conversion material or color conversion member are separated. In addition, for the purpose of improving color purity, the light source unit of the present invention may be configured to include a color filter.

[0255] <Light Source>

[0256] Regarding the type of light source possessed by the light source unit of the present invention, any light source can be used as long as it is a light source that shows light emission in the wavelength region that the luminescent material used in the particulate color conversion material or color conversion member of the present invention can absorb. For example, any light source of excitation light such as a hot cathode tube, a cold cathode tube, an inorganic electroluminescence (EL) or the like, an organic EL element light source, an LED light source, an incandescent light source, or sunlight, etc. can be used in principle. Among them, an LED light source is a preferred light source. For example, a light emitting diode having a maximum light emission in a wavelength range of 400nm to 500nm is a more preferred LED light source. In display and lighting applications, from the perspective of improving the color purity of blue light, a light emitting diode (blue LED light source) having a maximum light emission in a wavelength range of 400nm to 500nm is a further preferred light source. In addition, as a light source possessed by the light source unit of the present invention, a blue LED light source having a maximum light emission in a wavelength range of 430nm to 480nm is more preferred, and a blue LED light source having a maximum light emission in a wavelength range of 450nm to 470nm is further preferred.

[0257] The light source may be a light source having one luminous peak or a light source having more than two luminous peaks, but in order to improve color purity, a light source having one luminous peak is preferred. In addition, a plurality of light sources having different types of luminous peaks may be used in combination as desired.

[0258] The light source unit of the present invention is useful in various light sources such as space lighting and backlight. Specifically, the light source unit of the present invention can be used for displays, lighting devices, interior decoration, signs, signboards, etc., and is particularly preferably used for displays and lighting devices.

[0259] <Display, lighting device>

[0260] The display according to the embodiment of the present invention includes at least a light source unit including a light source and a particulate color conversion material or a color conversion member as described above. For example, the light source unit described above can be used as a backlight unit in a display such as a liquid crystal display.

[0261] In addition, the lighting device according to the embodiment of the present invention includes at least a light source unit including a light source and a particulate color conversion material or a color conversion member as described above. For example, the lighting device is configured in such a manner that a blue LED light source as the light source unit is combined with a particulate color conversion material or a color conversion member that converts blue light from the blue LED light source into light with a longer wavelength, thereby emitting white light.

[0262] Example

[0263] The present invention will be described below with reference to examples, but the present invention is not limited to the following examples. First, the measurement methods, evaluation methods, and light-emitting materials in the examples and comparative examples will be described.

[0264] <Measurement of Color Conversion Characteristics>

[0265] In the measurement of color conversion characteristics, each color conversion member and prism sheet to be evaluated were placed on a planar light-emitting device equipped with a blue LED element having a peak emission wavelength of 450 nm. A current of 30 mA was passed through the planar light-emitting device in this state to light up the blue LED element, and the emission spectrum, chromaticity, and brightness were measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta).

[0266] <Calculation of color gamut>

[0267] In the calculation of the color gamut, the color gamut in the (u', v') color space is calculated when the color purity is improved by using a color filter, based on the luminous spectrum obtained by measuring the above-mentioned color conversion characteristics and the spectral data of the transmittance of the color filter. In addition, for the area of ​​the color gamut in the calculated (u', v') color space, it is evaluated according to the following benchmarks based on the ratio when the color gamut area of ​​the BT.2020 standard is taken as 100%. As the evaluation result of the area of ​​the color gamut in the (u', v') color space, "A" means that the above ratio is greater than 91%. "B" means that the above ratio is greater than 86% and less than 90%. "C" means that the above ratio is greater than 81% and less than 85%. In this evaluation result, the higher the above ratio, the wider the color gamut, and the better the color reproducibility of the color conversion component.

[0268] <Durability Evaluation>

[0269] In the durability evaluation, a current of 30 mA was passed through a light-emitting device equipped with a color conversion member and a blue LED element (manufactured by USHIO EPITEX; model SMBB450H-1100, emission peak wavelength: 450 nm) prepared in each embodiment and comparative example, so that the blue LED element was lit, and the initial emission peak intensity was measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta). It should be noted that the distance between the color conversion member and the blue LED element in the light-emitting device was set to 3 cm. Then, light from the blue LED element was continuously irradiated in an environment of 60° C., and the time until the emission peak intensity decreased by 5% was observed, thereby evaluating the durability of the color conversion member.

[0270] <Evaluation of end degradation>

[0271] In the evaluation of end degradation, light irradiation was performed for 300 hours under the same conditions as the above-mentioned durability evaluation. Compared with the center of the sample, the luminous intensity was visually confirmed to be greatly reduced in the range of several mm from the end of the sample, and the evaluation was performed according to the following criteria. As the evaluation result of end degradation, "A" means that the distance from the above-mentioned end is greater than 0 mm and less than 1 mm. "B" means that the distance from the above-mentioned end is greater than 1 mm and less than 5 mm. "C" means that the distance from the above-mentioned end is greater than 5 mm. Among them, the sample of the color conversion component used for the measurement used a sheet sample cut into a size of 30 mm×30 mm.

[0272] <Determination of oxygen permeability>

[0273] In the measurement of oxygen permeability, a planar test piece with uniform film thickness was used as the evaluation object. Unless otherwise specified, the oxygen permeability of the planar test piece was measured at a temperature of 20° C. and a humidity of 0% RH using an oxygen permeability measuring device (model name: "OXTRAN" (registered trademark) ("OXTRAN" 2 / 20) manufactured by MOCON (USA) based on the electrolytic sensor method described in JIS K7126-2 (2006).

[0274] <Luminescent Materials>

[0275] In the following examples and comparative examples, compounds G-1, G-2, G-3, G-4, G-5, and R-1 were used as the luminescent materials contained in the particulate color conversion material or the color conversion member. Compounds G-1, G-2, G-3, G-4, G-5, and R-1 are the compounds shown below. Among them, compounds G-1, G-3, G-4, and G-5 are compounds that emit delayed fluorescence (delayed fluorescence materials).

[0276] [Chemical formula 15]

[0277]

[0278] [Chemical formula 16]

[0279]

[0280] Example 1

[0281] In Example 1, first, polyester resin T1 (SP value = 10.7 (cal / cm 3 ) 0.5) as a matrix resin, with respect to 100 parts by weight of the matrix resin, 0.10 parts by weight of compound G-1 as a luminescent material and 600 parts by weight of tetrahydrofuran as a solvent are mixed. Using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), the mixture is stirred and degassed at 300 rpm for 30 minutes to obtain a color conversion composition. The color conversion composition is dried by a spray drying method and further pulverized by a mortar to prepare a particulate color conversion material. For the particulate color conversion material, the particle size of 100 independent particles is measured using ECLIPSE L200N (manufactured by Nikon Co., Ltd.), and the average value is calculated. As a result, the average particle size is about 1 μm. The particle size is obtained by selecting the part with the largest diameter for measurement.

[0282] Next, hydrogenated SEBS copolymer resin T2 (SP value = 8.5 (cal / cm 3 ) 0.5 , oxygen permeability>2000cc / m 2 ·day·atm) as a material for a support, 300 parts by weight of cyclohexane as a solvent were mixed with 100 parts by weight of the resin. A planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.) was used to stir and degas their mixture at 300 rpm for 30 minutes to obtain a support resin liquid.

[0283] Finally, the above-mentioned particulate color conversion material and the support resin liquid were mixed, and the mixture was stirred and degassed at 1000 rpm for 20 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.) to prepare a color conversion dispersion liquid. The color conversion dispersion liquid was applied to a slide glass plate using an applicator, and heated and dried at 120° C. for 30 minutes to prepare a color conversion member (including the particulate color conversion material) with an average film thickness of 12 μm.

[0284] When the color of the light (blue light) from the blue LED element is converted using the color conversion member produced as described above, if only the light emitting area of ​​green light is selected, a high color purity green light emission with a peak wavelength of 523nm and a half-value width of the emission spectrum at the peak wavelength of 38nm is obtained. In addition, when the light from the blue LED element is continuously irradiated according to the above method, the time (light durability) until the brightness decreases by 5% is about 60 hours. In Example 1, when compared with Comparative Example 3 described later, the light durability is improved by about 2.4 times. The color conversion member of Example 1 and the evaluation results are shown in Table 2-1 described later.

[0285] Embodiments 2 to 4

[0286] In Examples 2 to 4, except that compounds G-3 to G-5 were used as luminescent materials, respectively, the color conversion components were prepared and evaluated in the same manner as in Example 1. The mixing amount of the luminescent material was adjusted so that the conversion rate when converting light from a blue LED element into green light was the same as that of compound G-1 in Example 1. The color conversion component and evaluation results of Example 2 are shown in Table 2-1.

[0287] Comparative Examples 1 and 2

[0288] In Comparative Examples 1 and 2, except that Coumarine 6 (manufactured by Sigma-Aldrich) or Compound G-2 was used as the luminescent material, the color conversion member was prepared and evaluated in the same manner as in Example 1. The mixing amount of the luminescent material was adjusted so that the conversion rate when converting light from a blue LED element into green light was the same as that of Compound G-1 in Example 1. The color conversion members and evaluation results in each of Comparative Examples 1 and 2 are shown in Table 2-1.

[0289] Comparative Examples 3 to 8

[0290] In Comparative Examples 3 to 8, the color conversion compositions prepared in Examples 1 to 4 and Comparative Examples 1 and 2 were applied onto a glass plate using a film applicator, heated at 120°C for 30 minutes, and dried to prepare a film-like color conversion member (excluding a particulate color conversion material). In each of Comparative Examples 3 to 8, the peak wavelength and half-value width when the color of light from a blue LED element was converted using the prepared color conversion member were measured to evaluate durability. The color conversion members and evaluation results in each of Comparative Examples 3 to 8 are shown in Table 2-2 described below. The oxygen permeability of the polyester resin T1 is 600 cc / m 2 ·day·atm.

[0291] Example 5

[0292] In Example 5, polyvinyl alcohol resin T3 (SP value = 12.6 (cal / cm 3 ) 0.5 , oxygen permeability = 0,4cc / m 2 ·day·atm) as a material for a support body, and 400 parts by weight of a water / 2-propanol mixed solution as a solvent were mixed with 100 parts by weight of the resin while heating and stirring, thereby obtaining a resin liquid for a support body.

[0293] Next, the particulate color conversion material prepared in Example 1 was mixed with the support resin liquid of Example 5, and the mixture was stirred and degassed at 1000 rpm for 20 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby preparing a color conversion dispersion liquid. The color conversion dispersion liquid was applied to a slide glass plate using an applicator, and heated and dried at 100° C. for 60 minutes to prepare a color conversion member (including the particulate color conversion material) with an average film thickness of 9 μm.

[0294] When the color conversion member produced as described above is used to convert the color of light from a blue LED element, if only the light emitting area of ​​green light is selected, a high color purity green light emission with a peak wavelength of 523nm and a half-value width of the emission spectrum at the peak wavelength of 38nm is obtained. In addition, when the light from the blue LED element is continuously irradiated according to the above method, the time until the brightness decreases by 5% is about 600 hours. In Example 5, when compared with Example 1, the light durability is improved by about 10 times. The color conversion member and evaluation results of Example 5 are shown in Table 3 described below.

[0295] Embodiments 6 to 8

[0296] In Examples 6 to 8, color conversion members were prepared and evaluated in the same manner as in Example 5, except that the particulate color conversion materials prepared in Examples 2 to 4 were used as the particulate color conversion materials. The color conversion members and evaluation results in each of Examples 6 to 8 are shown in Table 3.

[0297] Example 9

[0298] In Example 9, polyvinyl alcohol resin T5 (SP value = 12.2 (cal / cm 3 ) 0.5 , oxygen permeability = 0.8cc / m 2 The color conversion member of Example 9 and the evaluation results are shown in Table 3.

[0299] Example 10

[0300] In Example 10, ethylene vinyl alcohol copolymer resin T6 (SP value = 10.9 (cal / cm 3 ) 0.5 , oxygen permeability = 4.0cc / m 2 ·day·atm) as the material for the support, the same operation as in Example 5 was carried out to produce and evaluate the color conversion member.

[0301] Table 3 shows the color conversion member of Example 10 and the evaluation results.

[0302] Comparative Examples 9 and 10

[0303] In Comparative Examples 9 and 10, color conversion members were prepared and evaluated in the same manner as in Example 5 except that the particulate color conversion materials prepared in Comparative Examples 1 and 2 were used as the particulate color conversion materials. The color conversion members and evaluation results in Comparative Examples 9 and 10 are shown in Table 3.

[0304] Embodiment 11

[0305] In Example 11, first, polyester resin T1 (SP value = 10.7 (cal / cm 3 ) 0.5 ) as a matrix resin, 0.10 parts by weight of compound G-1 as a luminescent material and 600 parts by weight of tetrahydrofuran as a solvent were mixed with respect to 100 parts by weight of the matrix resin. The mixture was stirred and degassed at 300 rpm for 30 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a color conversion composition. The color conversion composition was dried by a spray drying method and further pulverized in a mortar to prepare a first particulate color conversion material having an average particle size of about 1 μm.

[0306] In the same manner as above, polyester resin T1 (SP value = 10.7 (cal / cm 3 ) 0.5 ) as a matrix resin, 0.10 parts by weight of compound R-1 as a luminescent material and 600 parts by weight of tetrahydrofuran as a solvent were mixed with respect to 100 parts by weight of the matrix resin. The mixture was stirred and degassed at 300 rpm for 30 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a color conversion composition. The color conversion composition was dried by a spray drying method and further pulverized in a mortar to prepare a second particulate color conversion material having an average particle size of about 1 μm.

[0307] Next, hydrogenated SEBS copolymer resin T2 (SP value = 8.5 (cal / cm 3 ) 0.5) as a material for a support, 300 parts by weight of cyclohexane as a solvent were mixed with 100 parts by weight of the resin. A planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.) was used to stir and degas their mixture at 300 rpm for 30 minutes to obtain a support resin liquid.

[0308] Finally, the first particulate color conversion material and the second particulate color conversion material are mixed with a support resin solution and stirred to prepare a color conversion dispersion liquid. The color conversion dispersion liquid is applied to a glass plate using an applicator, and heated and dried at 120° C. for 30 minutes to prepare a color conversion member (including the particulate color conversion material).

[0309] When the color conversion component made as described above is used to convert the color of the light (blue light) from the blue LED element, a part of the blue light is converted into green light and red light to obtain white light. If only the light-emitting area of ​​green light is selected, a green light with a peak wavelength of 523nm and a half-value width of the light-emitting spectrum at the peak wavelength of 36nm with high color purity is obtained. In addition, if only the light-emitting area of ​​red light is selected, a red light with a peak wavelength of 641nm and a half-value width of the light-emitting spectrum at the peak wavelength of 50nm with high color purity is obtained. The area of ​​the color gamut in the (u', v') color space is 91% relative to the color gamut area of ​​the BT.2020 standard. The color conversion component and evaluation results of Example 11 are shown in Table 4 described later. In Table 4, "color gamut area" is the area of ​​the color gamut in the (u', v') color space. In addition, "A" to "C" in the "color gamut area" column represent the evaluation results of the area of ​​the color gamut.

[0310] Example 12

[0311] In Example 12, acrylic resin T4 (SP value = 9.8 (cal / cm 3 ) 0.5 ) was used as the base resin of the second particulate color conversion material, and the same operation as in Example 11 was performed to produce and evaluate the color conversion member. The color conversion member of Example 12 and the evaluation results are shown in Table 4.

[0312] Example 13

[0313] In Example 13, acrylic resin T4 (SP value = 9.8 (cal / cm 3 ) 0.5) was used as the base resin of the first particulate color conversion material. The same operation as in Example 11 was followed to produce and evaluate the color conversion member. The color conversion member of Example 13 and the evaluation results are shown in Table 4.

[0314] Embodiment 14

[0315] In Example 14, first, polyester resin T1 (SP value = 10.7 (cal / cm 3 ) 0.5 ) as a matrix resin, with respect to 100 parts by weight of the matrix resin, 0.10 parts by weight of compound G-1 as a luminescent material, 0.10 parts by weight of compound R-1, and 600 parts by weight of tetrahydrofuran as a solvent were mixed. The mixture was stirred and degassed at 300 rpm for 30 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a color conversion composition. The color conversion composition was dried by a spray drying method and further pulverized in a mortar to prepare a first particulate color conversion material having an average particle size of about 1 μm.

[0316] Next, hydrogenated SEBS copolymer resin T2 (SP value = 8.5 (cal / cm 3 ) 0.5 ) As a material for the support, a resin liquid for the support is obtained in the same manner as in Example 3.

[0317] Finally, the first particulate color conversion material and the support resin liquid were mixed and stirred to prepare a color conversion dispersion. The color conversion dispersion was applied to a glass plate using an applicator, heated at 120° C. for 30 minutes, and dried to prepare a color conversion member (including the particulate color conversion material). The prepared color conversion member was evaluated in the same manner as in Example 11. The color conversion member of Example 14 and the evaluation results are shown in Table 4.

[0318] Comparative Example 11

[0319] In Comparative Example 11, Coumarine 6 (manufactured by Sigma-Aldrich) was used as the luminescent material of the first particulate color conversion material, and the conversion rate when converting light from a blue LED element into green light was adjusted and mixed in the same manner as that of Compound G-1 of Example 11, and Lumogen F Red 305 (manufactured by BASF) was used as the luminescent material of the second particulate color conversion material, and the amount of the substance was adjusted and mixed in the same manner as that of Compound R-1 of Example 11. The color conversion member was prepared and evaluated in the same manner as in Example 11. The color conversion member of Comparative Example 11 and the evaluation results are shown in Table 4.

[0320] Embodiment 15

[0321] In Example 15, first, polyester resin T1 (SP value = 10.7 (cal / cm 3 ) 0.5 ) as a base resin, 0.10 parts by weight of compound G-1 as a luminescent material and 600 parts by weight of tetrahydrofuran as a solvent were mixed with respect to 100 parts by weight of the base resin. The mixture was stirred and degassed at 300 rpm for 30 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a color conversion composition. The color conversion composition was dried by a spray drying method and further pulverized in a mortar to prepare a particulate color conversion material with an average particle size of about 1 μm.

[0322] Next, acrylic resin T4 (SP value = 9.8 (cal / cm 3 ) 0.5 , oxygen permeability = 600cc / m 2 ·day·atm) as a material for a support, 0.03 weight part of compound R-1 as a luminescent material, 200 weight parts of ethyl acetate as a solvent, and 200 weight parts of 1-methoxy-2-propanol were mixed with respect to 100 weight parts of the resin. The mixture was stirred and degassed at 300 rpm for 30 minutes using a planetary stirring and degassing device "Mazel Star" (registered trademark) KK-400 (manufactured by Kurabo Co., Ltd.), thereby obtaining a resin liquid for a support.

[0323] Finally, the particulate color conversion material and the support resin solution were mixed and stirred to prepare a color conversion dispersion, which was applied to a glass plate using an applicator, heated at 120° C. for 30 minutes, and dried to prepare a color conversion member (including the particulate color conversion material).

[0324] When the color conversion component made as described above is used to convert the color of the light from the blue LED element, if only the light-emitting area of ​​green light is selected, a green light with a peak wavelength of 523nm and a half-value width of the light-emitting spectrum at the peak wavelength of 33nm with high color purity is obtained. In addition, if only the light-emitting area of ​​red light is selected, a red light with a peak wavelength of 630nm and a half-value width of the light-emitting spectrum at the peak wavelength of 49nm with high color purity is obtained. The area of ​​the color gamut in the (u', v') color space is 86% relative to the color gamut area of ​​the BT.2020 standard. The color conversion component and evaluation results of Example 15 are shown in Table 5 described below. In Table 5, "color gamut area" is the area of ​​the color gamut in the (u', v') color space. In addition, "A" to "C" in the "color gamut area" column represent the evaluation results of the area of ​​the color gamut.

[0325] Example 16

[0326] In Example 16, the color conversion dispersion prepared in Example 5 was applied onto "Cerapeel" (registered trademark) BLK (a release film manufactured by Toray Advanced Film Co., Ltd.) using an applicator, and heated and dried at 100°C for 60 minutes to prepare a color conversion member (including a particulate color conversion material) having an average film thickness of 9 μm.

[0327] Next, as the oxygen barrier laminate film 1 constituting the oxygen barrier layer, a coated alumina-deposited polyethylene terephthalate film "Barrialox" (registered trademark) 1011SBR2 (manufactured by Toray Co., Ltd., with a thickness of 12 μm and an oxygen permeability of about 0.1 cc / m 2 ·day·atm), a thermosetting adhesive layer is formed on the coating layer by a coating method, and an oxygen barrier laminate film 1 is laminated on one side of the above-mentioned color conversion member. Then, "Cerapeel" (registered trademark) BLK is peeled off from the color conversion member, and an oxygen barrier laminate film 1 having a thermosetting adhesive layer formed in the same manner as above is laminated on the peeled surface. In this way, a color conversion member (including a particulate color conversion material) having oxygen barrier layers on both sides is produced.

[0328] When the color conversion member produced as described above was used and light from a blue LED element was continuously irradiated, the time until the brightness decreased by 5% (light durability) was about 1000 hours. In the durability evaluation of this Example 16, when compared with Comparative Example 12 described later, an improvement in light durability of about 8.3 times was shown. In addition, no end degradation was confirmed at the end of the sample. The color conversion member of Example 16 and the evaluation results are shown in Table 6-1 described later.

[0329] Embodiment 17

[0330] In Example 17, a thermosetting adhesive layer was formed on a polyethylene terephthalate film "Lumirror" (registered trademark) U48 (produced by Toray Co., Ltd., with a thickness of 50 μm) by a coating method, and an ethylene-vinyl alcohol copolymer film (ethylene content of 32 mol%, thickness of 12 μm) was laminated thereon as an oxygen barrier layer. Thus, an oxygen barrier laminated film 2 constituting an oxygen barrier layer was prepared. The oxygen permeability of the oxygen barrier laminated film 2 was about 0.7 cc / m 2 ·day·atm. A color conversion member (including a particulate color conversion material) was prepared and evaluated in the same manner as in Example 16, except that a thermosetting adhesive layer was formed on the ethylene-vinyl alcohol copolymer film of the oxygen barrier laminate film 2. The color conversion member and evaluation results of Example 17 are shown in Table 6-1.

[0331] Embodiment 18

[0332] In Example 18, the color conversion member (including the particulate color conversion material) was prepared and evaluated in the same manner as in Example 16, except that the color conversion dispersion prepared in Example 1 was used and heated at 120° C. for 30 minutes and dried to prepare a color conversion member (including the particulate color conversion material) having an average film thickness of 12 μm.

[0333] The color conversion member and evaluation results of Example 18 are shown in Table 6-1.

[0334] Embodiment 19

[0335] In Example 19, the color conversion member (including the particulate color conversion material) was prepared and evaluated in the same manner as in Example 17, except that the color conversion dispersion prepared in Example 1 was used and heated at 120° C. for 30 minutes and dried to prepare a color conversion member (including the particulate color conversion material) having an average film thickness of 12 μm.

[0336] The color conversion component of Example 19 and the evaluation results are shown in Table 6-1.

[0337] Embodiment 20

[0338] In Example 20, as the oxygen barrier laminate film 3 constituting the oxygen barrier layer, an uncoated alumina vapor-deposited polyethylene terephthalate film "Barrialox" (registered trademark) 1011HG (produced by Toray Co., Ltd., with a thickness of 12 μm and an oxygen permeability of about 1.5 cc / m 2·day·atm) and forming a thermosetting adhesive layer on the aluminum oxide layer of the film, the same operation as in Example 18 was carried out to prepare and evaluate the color conversion member (including the particulate color conversion material). The color conversion member of Example 20 and the evaluation results are shown in Table 6-1.

[0339] Comparative Example 12

[0340] In Comparative Example 12, the color conversion composition prepared in Example 1 was applied to "Cerapeel" (registered trademark) BLK (a release film manufactured by Toray Advanced Film Co., Ltd.) using an applicator, and heated and dried at 120°C for 30 minutes to prepare a film-like color conversion member (not including a particulate color conversion material). On both sides of the film-like color conversion member, an oxygen barrier laminated film 3 was laminated in the same manner as in Example 20, thereby preparing a color conversion member of Comparative Example 12 having oxygen barrier layers on both sides (not including a particulate color conversion material). Then, the color conversion member of Comparative Example 12 was evaluated. The color conversion member of Comparative Example 12 and the evaluation results are shown in Table 6-2.

[0341] [Table 2-1]

[0342]

[0343] [Table 2-2]

[0344]

[0345] [Table 3]

[0346]

[0347] [Table 4]

[0348]

[0349] [Table 5]

[0350]

[0351] [Table 6-1]

[0352]

[0353] [Table 6-2]

[0354]

[0355] Industrial Applicability

[0356] As described above, the particulate color conversion material, the color conversion member, and the light source unit, the display, the lighting device, and the color conversion substrate including the same according to the present invention are suitable for achieving both improved color reproducibility and improved durability.

[0357] Description of Reference Numerals

[0358] 1A, 1B, 1C, 1D, 1E, 1F, 1G color conversion components

[0359] 2a, 2b Granular color conversion material

[0360] 3a, 3b support body

[0361] 11 Oxygen barrier layer

Claims

1. A particulate color conversion material comprising a matrix resin and at least one luminescent material, wherein: The at least one light-emitting material includes an organic light-emitting material that emits delayed fluorescence having a half-value width of 50 nm or less.

2. The particulate color conversion material according to claim 1, wherein The organic light-emitting material is a compound containing a partial structure represented by general formula (1), [Chemical formula 1] In the general formula (1), B is a boron atom, N is a nitrogen atom, and C is a carbon atom; n is an integer from 0 to 2; when n is 0, the partial structure represented by the general formula (1) represents a direct bond structure between B and N.

3. The particulate color conversion material according to claim 2, wherein The organic light-emitting material is a compound containing two or more partial structures represented by the general formula (1).

4. The particulate color conversion material according to claim 1, wherein The organic light-emitting material comprises a compound represented by general formula (2) or general formula (3), [Chemical formula 2] In the general formula (2) or (3), ring Za, ring Zb and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 6 to 30 ring carbon atoms; Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom; 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring; 2 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring; E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O; E 1 and E 2 Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2; in E 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring; 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring; the substituent Ra is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxyl, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amide group, a sulfonyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted siloxane group, a substituted or unsubstituted borane group, a substituted or unsubstituted phosphine oxide group, and substituents selected from the condensed ring and aliphatic ring formed with the adjacent substituent; in addition, the substituent Ra may be further substituted by the substituents selected above, and these substituents may be further substituted by the substituents selected above.

5. The particulate color conversion material according to claim 4, wherein E in the general formula (2) is a boron atom, and E in the general formula (3) is 1 and E 2 It is BRa.

6. A color conversion component, characterized in that A support body including the particulate color conversion material according to any one of claims 1 to 5 is provided.

7. The color conversion member according to claim 6, wherein The color conversion component comprises: a first particulate color conversion material composed of a first luminescent material that emits luminescence having a peak wavelength observed in a region of 500 nm to less than 580 nm and a first matrix resin; and A second particulate color conversion material is formed of a second light emitting material that emits light with a peak wavelength observed in a region of 580 nm to 750 nm, and a second matrix resin.

8. The color conversion member according to claim 7, wherein The first light-emitting material includes at least an organic light-emitting material that emits delayed fluorescence having a half-value width of 50 nm or less.

9. The color conversion member according to claim 7, wherein The second light-emitting material contains at least a compound represented by the general formula (4), [Chemical formula 3] In the general formula (4), X is CR 7 or N; R 1 ~R 9 each may be the same or different, and is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and a condensed ring and aliphatic ring formed with adjacent substituents; R 1 ~R 9 Each independently may be substituted; for these R 1 ~R 9 The substituents for each substitution are selected from hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxy, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted The substituted or unsubstituted carboxyl group, substituted or unsubstituted oxycarbonyl group, substituted or unsubstituted ester group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted amide group, sulfonyl group, substituted or unsubstituted sulfonate group, substituted or unsubstituted sulfonamide group, substituted or unsubstituted amino group, substituted or unsubstituted imino group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted siloxane group, substituted or unsubstituted borane group, substituted or unsubstituted phosphine oxide group, and condensed ring and aliphatic ring formed with adjacent substituents.

10. The color conversion member according to claim 6, wherein The support further contains at least one light-emitting material.

11. The color conversion member according to claim 10, wherein The at least one light-emitting material contains at least one of a compound having a partial structure represented by the general formula (1), a compound represented by the general formula (2), and a compound represented by the general formula (3), [Chemical formula 4] In the general formula (1), B is a boron atom, N is a nitrogen atom, and C is a carbon atom; n is an integer from 0 to 2; when n is 0, the partial structure represented by the general formula (1) represents a direct bond structure between B and N; [Chemical formula 5] In the general formula (2) or (3), ring Za, ring Zb and ring Zc are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl ring having 6 to 30 ring carbon atoms; Z 1 and Z 2 Each is independently an oxygen atom, NRa (a nitrogen atom having a substituent Ra) or a sulfur atom; 1 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring; 2 In the case of NRa, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring; E is a boron atom, a phosphorus atom, SiRa (a silicon atom having a substituent Ra), or P=O; E 1 and E 2 Each is independently BRa (boron atom having substituent Ra), PRa (phosphorus atom having substituent Ra), SiRa2 (silicon atom having two substituent Ra), P(=O)Ra2 (phosphine oxide having two substituent Ra) or P(=S)Ra2 (phosphine sulfide having two substituent Ra), C=O (carbonyl), S(=O) or S(=O)2; in E 1 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zb to form a ring; 2 In the case of BRa, PRa, SiRa2, P(=O)Ra2 or P(=S)Ra2, the substituent Ra may be bonded to the ring Za or the ring Zc to form a ring; the substituent Ra is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxyl, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amide group, a sulfonyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted siloxane group, a substituted or unsubstituted borane group, a substituted or unsubstituted phosphine oxide group, and substituents selected from the condensed ring and aliphatic ring formed with the adjacent substituent; in addition, the substituent Ra may be further substituted by the substituents selected above, and these substituents may be further substituted by the substituents selected above.

12. The color conversion member according to claim 10, wherein The at least one luminescent material contains at least a compound represented by the general formula (4), [Chemical formula 6] In the general formula (4), X is CR 7 or N; R 1 ~R 9 each may be the same or different, and is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, carbamoyl, amino, nitro, silyl, siloxane, borane, phosphine oxide, and a condensed ring and aliphatic ring formed with adjacent substituents; R 1 ~R 9 Each independently may be substituted; for these R 1 ~R 9 The substituents for each substitution are selected from hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted alkynyl, hydroxy, thiol, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylether, substituted or unsubstituted arylthioether, halogen, cyano, aldehyde, substituted or unsubstituted carbonyl, substituted or unsubstituted The substituted or unsubstituted carboxyl group, substituted or unsubstituted oxycarbonyl group, substituted or unsubstituted ester group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted amide group, sulfonyl group, substituted or unsubstituted sulfonate group, substituted or unsubstituted sulfonamide group, substituted or unsubstituted amino group, substituted or unsubstituted imino group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted siloxane group, substituted or unsubstituted borane group, substituted or unsubstituted phosphine oxide group, and condensed ring and aliphatic ring formed with adjacent substituents.

13. The color conversion member according to claim 6, wherein The oxygen permeability of the support is 1.0 cc / m 2 ·day·atm or less.

14. The color conversion member according to claim 6, wherein The support has an oxygen barrier layer on at least a portion of its surface.

15. A light source unit, characterized in that have: light source; and The particulate color conversion material according to any one of claims 1 to 5.

16. The light source unit according to claim 15, wherein: The light source is a light emitting diode having a maximum light emission within a wavelength range of 400 nm to 500 nm.

17. A display, characterized in that A light source unit according to claim 15 is provided.

18. A lighting device, characterized in that A light source unit according to claim 15 is provided.

19. A color conversion substrate, characterized in that Contains the particulate color conversion material according to any one of claims 1 to 5.

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