Photosensitive composition

Abstract

To provide a photosensitive composition having favorable heat resistance and / or coatability.SOLUTION: A photosensitive composition according to the present invention, the photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C) and a photoinitiator (D), satisfies at least one of the following (a) to (c). (a) The photosensitive composition further contains a stabilizer (E) and the content of the stabilizer (E) is equal to or more than 8 mass% with respect to the total amount of the photosensitive composition. (b) The photopolymerizable compound (C) contains a methacrylate compound (C1) with the molecular weight of 180 or less. (c) The photopolymerizable compound (C) contains a compound (C2) having a vinyl ether group and a methacryloyl group in a same molecule.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a photosensitive composition, particularly a photosensitive composition suitable for ink for an inkjet printer.

Background Art

[0002] As a curable resin composition for forming a cured film such as a wavelength conversion film included in a display device such as an image display device, those containing semiconductor particles such as semiconductor quantum dots are known (Patent Document 1). Further, a method of manufacturing a wavelength conversion film or the like by an inkjet method using an ink composition containing semiconductor quantum dots has been studied (Patent Documents 2 and 3).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0004] Semiconductor particles such as semiconductor quantum dots are vulnerable to heat, and there may be a case where improvement in heat resistance of a cured film such as a wavelength conversion film formed from a photosensitive composition containing semiconductor particles is required. Further, the photosensitive composition may also be required to have better coatability.

[0005] An object of the present invention is to provide a photosensitive composition containing semiconductor particles, which has good heat resistance and / or coatability.

Means for Solving the Problems

[0006] The present invention is as follows. [1] A photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C), a photoinitiator (D), and a stabilizer (E), wherein the content of the stabilizer (E) is 8% by mass or more based on the total amount of the photosensitive composition. [2] A photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C), and a photoinitiator (D), wherein the photopolymerizable compound (C) contains a (meth)acrylate compound (C1) having a molecular weight of 180 or less. [3] A photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C), and a photoinitiator (D), wherein the photopolymerizable compound (C) contains a compound (C2) having a vinyl ether group and a (meth)acryloyl group in the same molecule. [4] The photosensitive composition according to any one of [1] to [3], wherein the photopolymerizable compound (C) contains a (meth)acrylate compound (C1) having a molecular weight of 180 or less. [5] The photosensitive composition according to any one of [1] to [4], wherein the photopolymerizable compound (C) contains a compound (C2) having a vinyl ether group and a (meth)acryloyl group in the same molecule. [6] The photosensitive composition according to any one of [1] to [5], wherein the photosensitive composition further contains a stabilizer (E), and the content of the stabilizer (E) is 8% by mass or more based on the total amount of the photosensitive composition. [7] The photosensitive composition according to any one of [1] to [6], wherein the viscosity of the compound (C1) at 25°C is 1.2 cP or less. [8] The photosensitive composition according to any one of [1] to [7], wherein the content of the compound (C1) is 5% by mass or more and 50% by mass or less based on the total amount of the photosensitive composition. [9] The photosensitive composition according to any one of [1] to [8], wherein the content of the compound (C2) is 5% by mass or more and 50% by mass or less based on the total amount of the photosensitive composition.

[10] The photosensitive composition according to any one of [1] to [9], wherein the content of the stabilizer (E) is 16% by mass or more based on the total amount of the photosensitive composition.

[11] The photosensitive composition according to any one of [1] to

[10] , wherein the content of the semiconductor particles (A) is 16% by mass or more and 45% by mass or less based on the total amount of the photosensitive composition.

[12] The photosensitive composition according to any one of [1] to

[11] , wherein the photopolymerizable compound (C) includes a compound (C3) having a carboxyl group and three or more functional groups other than the carboxyl group in the same molecule.

[13] The photosensitive composition according to

[12] , wherein the content of the compound (C3) is 25 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the semiconductor particles (A).

[14] The photosensitive composition according to any one of [1] to

[13] , wherein the viscosity of the photosensitive composition at 40 °C is 20 cP or less.

[15] The photosensitive composition according to any one of [1] to

[14] , wherein the content of the photoinitiator (D) is 8 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the photopolymerizable compound (C).

[16] The photosensitive composition according to any one of [1] to

[15] , further comprising a light scattering agent (B) having a volume-based median diameter of 0.15 μm or more.

[17] The photosensitive composition further comprises a solvent (F), The photosensitive composition according to any one of [1] to

[16] , wherein the content of the solvent (F) is 3.5% by mass or less based on the total amount of the photosensitive composition.

[18] The photosensitive composition according to any one of [1] to

[17] , which is an ink for an inkjet printer.

[19] Use of the photosensitive composition according to

[18] , which is ejected from a discharge head of an inkjet printer at a temperature of 40 °C or higher.

[20] A cured film formed from the photosensitive composition according to any one of [1] to

[18] .

[21] The cured film according to

[20] , having a vertical dimension of 9 μm or more and / or a horizontal dimension of 10 μm or more and 900 μm or less.

Advantages of the Invention

[0007] According to the present invention, a photosensitive composition having good heat resistance and / or coatability can be provided.

Brief Description of the Drawings

[0008]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0009] <Photosensitive Composition> The photosensitive composition according to the present invention is a photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C), and a photopolymerization initiator (D), and satisfies any one or more of the following (a) to (c). (a) Further contains a stabilizer (E), and the content of the stabilizer (E) is 8% by mass or more based on the total amount of the photosensitive composition (b) The photopolymerizable compound (C) contains a (meth)acrylate compound (C1) having a molecular weight of 180 or less (c) The photopolymerizable compound (C) contains a compound (C2) having a vinyl ether group and a (meth)acryloyl group in the same molecule

[0010] The photosensitive composition of the present invention only needs to satisfy any one of the above (a) to (c), but may satisfy any two of the above (a) to (c), or may satisfy all of the above (a) to (c).

[0011] In addition, the compounds exemplified as each component contained in or that can be contained in the photosensitive composition in this specification can be used alone or in combination of a plurality of types without particular notice.

[0012] <Semiconductor particles (A)> The semiconductor particles (A) are preferably luminescent (fluorescent) semiconductor particles. A cured film such as a wavelength conversion film formed from a photosensitive composition containing luminescent semiconductor particles can have excellent color reproducibility showing fluorescent emission in a desired wavelength range.

[0013] The semiconductor particles (A) may be red-emitting semiconductor particles that emit light having an emission peak wavelength in the range of 605 to 665 nm, may be green-emitting semiconductor particles that emit light having an emission peak wavelength in the range of 500 to 560 nm, or may be blue-emitting semiconductor particles that emit light having an emission peak wavelength in the range of 420 to 480 nm. Also, the light absorbed by the semiconductor particles (A) may be, for example, light having a wavelength in the range of 400 nm or more and less than 500 nm (blue light), or light having a wavelength in the range of 200 nm to 400 nm (ultraviolet light). The emission peak wavelength of the semiconductor particles (A) can be confirmed, for example, in an emission spectrum measured using an ultraviolet-visible spectrophotometer. Also, the full width at half maximum of the emission spectrum of the semiconductor particles (A) is preferably 60 nm or less, more preferably 55 nm or less, still more preferably 50 nm or less, and particularly preferably 45 nm or less. Thereby, light with higher color purity can be obtained. Also, the lower limit of the full width at half maximum of the emission spectrum of the semiconductor particles (A) is not particularly limited, but may be 5 nm or more, or may be 15 nm or more.

[0014] The luminescent semiconductor particles are particles composed of a semiconductor crystal, preferably nanoparticles composed of a semiconductor crystal. Preferred examples of the luminescent semiconductor particles include semiconductor quantum dots and compounds having a perovskite crystal structure (hereinafter referred to as "perovskite compounds"), and more preferably semiconductor quantum dots.

[0015] The average particle diameter of the semiconductor quantum dots is, for example, 0.5 nm or more and 20 nm or less, preferably 1 nm or more and 15 nm or less (for example, 2 nm or more and 15 nm or less). The average particle diameter of the semiconductor quantum dots can be determined using a transmission electron microscope (TEM).

[0016] The semiconductor quantum dots can be composed of a semiconductor material containing one or more elements selected from the group consisting of, for example, Group 2 elements, Group 11 elements, Group 12 elements, Group 13 elements, Group 14 elements, Group 15 elements, and Group 16 elements of the periodic table.

[0017] Specific examples of the semiconductor material that can form the semiconductor quantum dots include compounds of Group 14 elements and Group 16 elements such as SnS2, SnS, SnSe, SnTe, PbS, PbSe, PbTe; compounds of Group 13 elements and Group 15 elements such as GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, InGaN, InGaP; compounds of Group 13 elements and Group 16 elements such as Ga2O3, Ga2S3, Ga2Se3, Ga2Te3, In2O3, In2S3, In2Se3, In2Te3; compounds of Group 12 elements and Group 16 elements such as ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, HgO, HgS, HgSe, HgTe, ZnSTe, ZnSeS, ZnSeTe, CdSTe, CdSeTe, HgSTe, HgSeS, HgSeTe; compounds of Group 15 elements and Group 16 elements such as As2O3, As2S3, As2Se3, As2Te3, Sb2O3, Sb2S3, Sb2Se3, Sb2Te3, Bi2O3, Bi2S3, Bi2Se3, Bi2Te3; compounds of Group 2 elements and Group 16 elements such as MgS, MgSe, MgTe, CaS, CaSe, CaTe, SrS, SrSe, SrTe, BaS, BaSe, BaTe; and elements of Group 14 elements, Group 15 elements, or Group 16 elements such as Si, Ge.

[0018] A semiconductor quantum dot may have a single-layer structure composed of a single semiconductor material, or may have a core-shell structure in which the surface of a core particle (core layer) composed of a single semiconductor material is coated with a coating layer (shell layer) composed of one or more different semiconductor materials. In the latter case, as the semiconductor material constituting the shell layer, a material having a larger bandgap energy than the semiconductor material constituting the core layer is usually used. The semiconductor quantum dot may have two or more shell layers. The shape of the semiconductor quantum dot is not particularly limited, and may be, for example, spherical or substantially spherical, rod-shaped, disk-shaped, or the like.

[0019] The perovskite compound is a compound having a perovskite crystal structure and containing A, B, and X as components. A is a component located at each vertex of an octahedron centered on B in the perovskite crystal structure and is a monovalent cation. X represents a component located at each vertex of an octahedron centered on B in the perovskite crystal structure and is at least one ion selected from the group consisting of halide ions and thiocyanate ions. B is a component located at the center of an octahedron having A at its vertices and an octahedron having X at its vertices in the perovskite crystal structure and is a metal ion.

[0020] From the viewpoint of maintaining a good crystal structure, the average particle size of the perovskite compound is preferably 3 nm or more, more preferably 4 nm or more, and even more preferably 5 nm or more. Also, from the viewpoint of suppressing precipitation of the perovskite compound in the photosensitive composition, the average particle size of the perovskite compound is preferably 5 μm or less, more preferably 500 nm or less, and even more preferably 100 nm or less. The average particle size of the perovskite compound can be determined using a transmission electron microscope (TEM).

[0021] The perovskite compound containing A, B, and X as components is not particularly limited, and may be a compound having any of a three-dimensional structure, a two-dimensional structure, and a pseudo-two-dimensional structure. In the case of a three-dimensional structure, the perovskite compound is represented by ABX (3+δ) . In the case of a two-dimensional structure, the perovskite compound is represented by A2BX (4+δ) . Here, δ is a number that can be appropriately changed according to the charge balance of B, and is -0.7 or more and 0.7 or less.

[0022] A perovskite compound represented by ABX (3+δ) Specific examples of compounds having a three-dimensional perovskite crystal structure represented by include CH3NH3PbBr3, CH3NH3PbCl3, CH3NH3PbI3, CH3NH3PbBr (3-y) I y (0 < y < 3), CH3NH3PbBr (3-y) Cl y (0 < y < 3), (H2N=CH-NH2)PbBr3, (H2N=CH-NH2)PbCl3, (H2N=CH-NH2)PbI3, CH3NH3Pb (1-a) Ca a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Sr a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) La a Br (3+δ) (0 < a ≤ 0.7, 0 < δ ≤ 0.7), CH3NH3Pb (1-a) Ba a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Dy a Br (3+δ) (0 < a ≤ 0.7, 0 < δ ≤ 0.7), CH3NH3Pb (1-a) Na a Br (3+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), CH3NH3Pb (1-a) Li a Br (3+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), CsPb (1-a) Na a Br (3+δ)(0 < a ≤ 0.7, -0.7 ≤ δ < 0), CsPb (1-a) Li a Br (3+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), CH3NH3Pb (1-a) Na a Br (3+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), CH3NH3Pb (1-a) Li a Br (3+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), CH3NH3Pb (1-a) Na a Br (3+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), CH3NH3Pb (1-a) Li a Br (3+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), (H2N = CH - NH2)Pb (1-a) Na a Br (3+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), (H2N = CH - NH2)Pb (1-a) Li a Br (3+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), (H2N = CH - NH2)Pb (1-a) Na a Br (3+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), (H2N = CH - NH2)Pb (1-a) Na a Br (3+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 3), CsPbBr3, CsPbCl3, CsPbI3, CsPbBr (3-y) I y (0 < y < 3) 、CsPbBr (3-y) Cl y (0 < y < 3), CH3NH3PbBr (3-y) Cl y (0 < y < 3), CH3NH3Pb (1-a) Zn a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Al a Br (3+δ) (0 < a ≤ 0.7, 0 ≤ δ ≤ 0.7), CH3NH3Pb (1-a) Co a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Mn a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Mg a Br3(0 < a ≤ 0.7), CsPb (1-a) Zn a Br3(0 < a ≤ 0.7), CsPb (1-a) Al a Br (3+δ) (0 < a ≤ 0.7, 0 < δ ≤ 0.7), CsPb (1-a) Co a Br3(0 < a ≤ 0.7), CsPb (1-a) Mn a Br3(0 < a ≤ 0.7), CsPb (1-a) Mg a Br3(0 < a ≤ 0.7), CH3NH3Pb (1-a) Zn a Br (3-y) I y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Al a Br (3+δ-y) I y (0 < a ≤ 0.7, 0 < δ ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Co a Br (3-y) I y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Mn a Br (3-y) I y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Mg a Br (3-y) I y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Zn a Br(3-y) Cl y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Al a Br (3+δ-y) Cl y (0 < a ≤ 0.7, 0 < δ ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Co a Br (3+δ-y) Cl y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Mn a Br (3-y) Cl y (0 < a ≤ 0.7, 0 < y < 3), CH3NH3Pb (1-a) Mg a Br (3-y) Cl y (0 < a ≤ 0.7, 0 < y < 3), (H2N = CH - NH2)Zn a Br3(0 < a ≤ 0.7), (H2N = CH - NH2)Mg a Br3(0 < a ≤ 0.7), (H2N = CH - NH2)Pb (1-a) Zn a Br (3-y) I y (0 < a ≤ 0.7, 0 < y < 3), (H2N = CH - NH2)Pb (1-a) Zn a Br (3-y) Cl y (0 < a ≤ 0.7, 0 < y < 3), etc. are preferably listed.

[0023] A perovskite compound, A2BX (4+δ) As preferable specific examples of the compound having a two - dimensional perovskite - type crystal structure represented by (C4H9NH3)2PbBr4, (C4H9NH3)2PbCl4, (C4H9NH3)2PbI4, (C7H 15 NH3)2PbBr4, (C7H 15 NH3)2PbCl4, (C7H 15 NH3)2PbI4, (C4H9NH3)2Pb (1-a) Li a Br (4+δ)(0 < a ≤ 0.7, -0.7 ≤ δ < 0), (C4H9NH3)2Pb (1-a) Na a Br (4+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0), (C4H9NH3)2Pb (1-a) Rb a Br (4+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0) (C7H 15 NH3)2Pb (1-a) Na a Br (4+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0) 、(C7H 15 NH3)2Pb (1-a) Li a Br (4+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0) 、(C7H 15 NH3)2Pb (1-a) RbaBr (4+δ) (0 < a ≤ 0.7, -0.7 ≤ δ < 0) (C4H9NH3)2Pb (1-a) Na a Br (4+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4), (C4H9NH3)2Pb (1-a) Li a Br (4+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4), (C4H9NH3)2Pb (1-a) Rb a Br (4+δ-y) I y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4) (C4H9NH3)2Pb (1-a) Na a Br (4+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4), (C4H9NH3)2Pb (1-a) Li a Br (4+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4), (C4H9NH3)2Pb (1-a) Rb a Br(4+δ-y) Cl y (0 < a ≤ 0.7, -0.7 ≤ δ < 0, 0 < y < 4), (C4H9NH3)2PbBr4, (C7H 15 NH3)2PbBr4, (C4H9NH3)2PbBr (4-y) Cl y (0 < y < 4), (C4H9NH3)2PbBr (4-y) I y (0 < y < 4), (C4H9NH3)2Pb (1-a) Zn a Br4(0 < a ≤ 0.7), (C4H9NH3)2Pb (1-a) Mg a Br4(0 < a ≤ 0.7), (C4H9NH3)2Pb (1-a) Co a Br4(0 < a ≤ 0.7), (C4H9NH3)2Pb (1-a) Mn a Br4(0 < a ≤ 0.7), (C7H 15 NH3)2Pb (1-a) Zn a Br4(0 < a ≤ 0.7), (C7H 15 NH3)2Pb (1-a) Mg a Br4(0 < a ≤ 0.7), (C7H 15 NH3)2Pb (1-a) Co a Br4(0 < a ≤ 0.7), (C7H 15 NH3)2Pb (1-a) Mn a Br4(0 < a ≤ 0.7), (C4H9NH3)2Pb (1-a) Zn a Br (4-y) I y (0 < a ≤ 0.7, 0 < y < 4), (C4H9NH3)2Pb (1-a) Mg a Br (4-y) I y (0 < a ≤ 0.7, 0 < y < 4), (C4H9NH3)2Pb (1-a) Co a Br (4-y) I y (0 < a ≤ 0.7, 0 < y < 4), (C4H9NH3)2Pb(1-a) Mn a Br (4-y) I y (0 < a ≤ 0.7, 0 < y < 4), (C4H9NH3)2Pb (1-a) Zn a Br (4-y) Cl y (0 < a ≤ 0.7, 0 < y < 4), (C4H9NH3)2Pb (1-a) Mg a Br (4-y) Cl y (0 < a ≤ 0.7, 0 < y < 4), (C4 H9NH3)2Pb (1-a) Co a Br (4-y) Cl y (0 < a ≤ 0.7, 0 < y < 4), (C4H9 NH3)2Pb (1-a) Mn a Br (4-y) Cl y (0 < a ≤ 0.7, 0 < y < 4), etc. can be mentioned.

[0024] The semiconductor particle (A) may be a ligand-containing semiconductor particle containing an organic ligand coordinated to the semiconductor particle. The organic ligand coordinated to the semiconductor particle can be, for example, an organic compound having a polar group exhibiting a coordination ability to the semiconductor particle. The organic ligand contained in the ligand-containing semiconductor particle may be an organic ligand added for the synthesis constraints of the ligand-containing semiconductor particle or for stabilization. For example, in Japanese Patent Application Laid-Open No. 2015-529698, the ligand-containing semiconductor particle contains hexanoic acid as an organic ligand from the viewpoint of particle size control, and the organic ligand is replaced with DDSA (dodecenyl succinic acid) for stabilization after synthesis. The organic ligand can be coordinated to the surface of the semiconductor particle, for example.

[0025] The organic ligand coordinating to the semiconductor particles may be one type of ligand or two or more types of ligands. When the organic ligand is an organic compound having a polar group, the organic ligand usually coordinates to the semiconductor particles via the polar group. The coordination of the organic ligand is confirmed by the uniform dispersion of the semiconductor particles in a dispersion medium suitable for the organic ligand.

[0026] The polar group is preferably at least one group selected from the group consisting of, for example, a thiol group (-SH), a carboxyl group (-COOH), and an amino group (-NH2). The polar group selected from this group can be advantageous in enhancing the coordination property to the semiconductor particles. High coordination property can contribute to the improvement of color unevenness of the cured film and / or the patterning property of the photosensitive composition. Among them, from the viewpoint of obtaining a cured film (such as a wavelength conversion film) with more excellent light-emitting characteristics, the polar group is more preferably at least one group selected from the group consisting of a thiol group and a carboxyl group. The organic ligand may have one or two or more polar groups.

[0027] The molecular weight of the organic ligand coordinating to the semiconductor particles is not particularly limited, but is, for example, 50 or more and 500 or less, preferably 80 or more and 400 or less. When the molecular weight of the organic ligand is within this range, ligand-containing semiconductor particles can be prepared with excellent reproducibility.

[0028] The organic ligand is, for example, represented by the following formula: Y-Z It can be an organic compound represented by the formula. In the formula, Y is the above-mentioned polar group, and Z is a monovalent hydrocarbon group which may contain a heteroatom (such as N, O, S, halogen atom, etc.). The hydrocarbon group may have one or more unsaturated bonds such as carbon-carbon double bonds. The hydrocarbon group may have a linear, branched or cyclic structure. The number of carbon atoms of the hydrocarbon group is, for example, 1 or more and 40 or less, and may also be 1 or more and 30 or less. The methylene group contained in the hydrocarbon group may be substituted with -O-, -S-, -C(=O)-, -C(=O)-O-, -O-C(=O)-, -C(=O)-NH-, -NH-, etc. Usually, the hydrocarbon group often does not contain a heteroatom for the convenience of preparing ligand-containing semiconductor particles. The organic ligand represented by Y-Z is preferably a saturated fatty acid having 5 or more and 12 or less carbon atoms or an unsaturated fatty acid having 5 or more and 12 or less carbon atoms.

[0029] The group Z may contain a polar group. For specific examples of the polar group, the above description regarding the polar group Y is cited. Usually, the group Z often does not contain a polar group for the convenience of preparing ligand-containing semiconductor particles.

[0030] Specific examples of the organic ligand having a carboxyl group as the polar group Y include formic acid, acetic acid, propionic acid, and saturated or unsaturated fatty acids. Specific examples of saturated or unsaturated fatty acids include saturated fatty acids such as butyric acid, pentanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid; monounsaturated fatty acids such as myristoleic acid, palmitoleic acid, oleic acid, eicosenoic acid, erucic acid, nervonic acid; polyunsaturated fatty acids such as linoleic acid, α-linolenic acid, γ-linolenic acid, stearidonic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosatetraenoic acid, docosadienoic acid, adrenic acid (eicosatetraenoic acid).

[0031] Specific examples of the organic ligand having a thiol group or an amino group as the polar group Y include organic ligands in which the carboxyl group of the organic ligand having a carboxyl group as the polar group Y exemplified above is replaced with a thiol group or an amino group.

[0032] The content of the semiconductor particles (A) is preferably 10% by mass or more, more preferably 16% by mass or more, still more preferably 17% by mass or more, even more preferably 18% by mass or more, particularly preferably 20% by mass or more, and most preferably 25% by mass or more, based on the total amount of the photosensitive composition. Also, it is preferably 45% by mass or less, more preferably 40% by mass or less, and still more preferably 35% by mass or less. When the content of the semiconductor particles (A) is within the above range, sufficient light conversion efficiency can be obtained in the cured film (such as a wavelength conversion film).

[0033] <Light scattering agent (B)> The photosensitive composition of the present invention preferably contains a light scattering agent (B). By including the light scattering agent (B), the light scattering property of the light from the light source irradiated on the wavelength conversion film formed from the photosensitive composition is improved. Examples of the light scattering agent (B) include particles of a metal or a metal oxide, glass particles, etc. Examples of the metal oxide include TiO2, SiO2, BaTiO3, ZnO, etc.

[0034] The volume-based median diameter of the light scattering agent (B) is, for example, 0.03 μm or more, preferably 0.10 μm or more, more preferably 0.15 μm or more, and still more preferably 0.20 μm or more, and is, for example, 20 μm or less, preferably 5 μm or less, and still more preferably 1 μm or less.

[0035] The content of the light scattering agent (B) is usually 0.001% by mass or more and 50% by mass or less, preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and still more preferably 1% by mass or more, based on the total amount of the photosensitive composition. Also, it is preferably 30% by mass or less, more preferably 15% by mass or less, and still more preferably 10% by mass or less.

[0036] <Photopolymerizable compound (C)> Examples of the photopolymerizable compound (C) include a photoradical polymerizable compound that is cured by a radical polymerization reaction upon irradiation with light, and a photocationic polymerizable compound that is cured by a cationic polymerization reaction upon irradiation with light. The photopolymerizable compound (C) is preferably a photoradical polymerizable compound. The weight average molecular weight of the photopolymerizable compound (C) is preferably 3000 or less.

[0037] Examples of the photoradical polymerizable compound include compounds having a polymerizable ethylenic unsaturated bond, and among them, (meth)acrylate compounds are preferable. Examples of the (meth)acrylate compound include a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule, a bifunctional (meth)acrylate monomer having two (meth)acryloyloxy groups in the molecule, and a polyfunctional (meth)acrylate monomer having three or more (meth)acryloyloxy groups in the molecule.

[0038] Examples of monofunctional (meth)acrylate monomers include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, dodecyl (meth)acrylate, hexadecyl (meth)acrylate, octadecyl (meth)acrylate, cyclohexyl (meth)acrylate, methoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, glycidyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, succinic acid mono(2-acryloyloxyethyl), N-[2-(acryloyloxy)ethyl]phthalimide, N-[2-(acryloyloxy)ethyl]tetrahydrophthalimide, 2-(2-vinyloxyethoxy)ethyl (meth)acrylate, ω-carboxy-polycaprolactone monoacrylate, and the like.

[0039] Examples of the bifunctional (meth)acrylate monomer include 1,3-butylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol hydroxypivalate di(meth)acrylate, di(meth)acrylate in which two hydroxyl groups of tris(2-hydroxyethyl) isocyanurate are substituted by (meth)acryloyloxy groups, di(meth)acrylate in which two hydroxyl groups of a diol obtained by adding 4 moles or more of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol are substituted by (meth)acryloyloxy groups, di(meth)acrylate in which two hydroxyl groups of a diol obtained by adding 2 moles of ethylene oxide or propylene oxide to 1 mole of bisphenol A are substituted by (meth)acryloyloxy groups, di(meth)acrylate in which two hydroxyl groups of a triol obtained by adding 3 moles or more of ethylene oxide or propylene oxide to 1 mole of trimethylolpropane are substituted by (meth)acryloyloxy groups, di(meth)acrylate in which two hydroxyl groups of a diol obtained by adding 4 moles or more of ethylene oxide or propylene oxide to 1 mole of bisphenol A are substituted by (meth)acryloyloxy groups, and the like.

[0040] Examples of the polyfunctional (meth)acrylate monomer include glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, pentaerythritol triacrylate succinic acid monoester, dipentaerythritol pentaacrylate succinic acid monoester, and the like.

[0041] Examples of the photocationic polymerizable compound include a compound having at least one oxetane ring (4-membered ring ether) in the molecule (hereinafter sometimes simply referred to as "oxetane compound"), a compound having at least one oxirane ring (3-membered ring ether) in the molecule (hereinafter sometimes simply referred to as "epoxy compound"), and vinyl ether compounds.

[0042] Examples of the oxetane compound include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis〔(3-ethyl-3-oxetanyl)methoxymethyl〕benzene, 3-ethyl-3-(phenoxymethyl)oxetane, di〔(3-ethyl-3-oxetanyl)methyl〕ether, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, phenol novolak oxetane, and the like. These oxetane compounds can be easily obtained as commercial products. As commercial products, all of them are sold under the trade names of Toagosei Co., Ltd., including "ARON OXETANE (registered trademark) OXT-101", "ARON OXETANE (registered trademark) OXT-121", "ARON OXETANE (registered trademark) OXT-211", "ARON OXETANE (registered trademark) OXT-221", "ARON OXETANE (registered trademark) OXT-212", and the like.

[0043] Examples of the epoxy compound include aromatic epoxy compounds, glycidyl ethers of polyols having an alicyclic ring, aliphatic epoxy compounds, alicyclic epoxy compounds, and the like.

[0044] Examples of the aromatic epoxy compound include bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, and diglycidyl ether of bisphenol S; novolak-type epoxy resins such as phenol novolak epoxy resin, cresol novolak epoxy resin, and hydroxybenzaldehyde phenol novolak epoxy resin; and polyfunctional epoxy resins such as glycidyl ether of tetrahydroxyphenylmethane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol.

[0045] As the glycidyl ether of a polyol having an alicyclic ring, there may be mentioned those obtained by glycidyl etherifying a nuclear hydrogenated polyhydroxy compound obtained by subjecting an aromatic polyol to a selective hydrogenation reaction on the aromatic ring under pressure in the presence of a catalyst. Examples of the aromatic polyol include bisphenol-type compounds such as bisphenol A, bisphenol F, and bisphenol S; novolak-type resins such as phenol novolak resin, cresol novolak resin, and hydroxybenzaldehyde phenol novolak resin; and polyfunctional compounds such as tetrahydroxydiphenylmethane, tetrahydroxybenzophenone, and polyvinylphenol. By reacting epichlorohydrin with the alicyclic polyol obtained by subjecting the aromatic ring of these aromatic polyols to a hydrogenation reaction, a glycidyl ether can be obtained. Among such glycidyl ethers of polyols having an alicyclic ring, preferably there may be mentioned the diglycidyl ether of hydrogenated bisphenol A.

[0046] Examples of the aliphatic epoxy compound include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts. Specifically, diglycidyl ether of 1,4-butanediol; diglycidyl ether of 1,6-hexanediol; triglycidyl ether of glycerin; triglycidyl ether of trimethylolpropane; diglycidyl ether of polyethylene glycol; diglycidyl ether of propylene glycol; diglycidyl ether of neopentyl glycol; and polyglycidyl ethers of polyether polyols obtained by adding one or more alkylene oxides (ethylene oxide, propylene oxide) to an aliphatic polyhydric alcohol such as ethylene glycol, propylene glycol, or glycerin.

[0047] An alicyclic epoxy compound is a compound having at least one structure in the molecule that forms an oxirane ring together with the carbon atoms of the alicyclic ring. Compounds such as the "Celloxide" series and "Cyclomer" (both manufactured by Daicel Corporation), and the "Silacure UVR" series (manufactured by Dow Chemical Company) can be used.

[0048] Examples of the vinyl ether compound include 2-hydroxyethyl vinyl ether, triethylene glycol vinyl monoether, tetraethylene glycol divinyl ether, trimethylolpropane trivinyl ether, and the like.

[0049] The photopolymerizable compound (C) preferably contains a (meth)acrylate compound (C1) (hereinafter sometimes simply referred to as "compound (C1)") having a molecular weight of 180 or less. The compound (C1) is not particularly limited as long as it has a molecular weight of 180 or less and has a (meth)acryloyloxy group. When the photosensitive composition contains the compound (C1), the viscosity of the composition can be reduced and the coatability is further improved.

[0050] Examples of the compound (C1) include a monofunctional (meth)acrylate monomer having a molecular weight of 180 or less and having one (meth)acryloyloxy group in the molecule, and a bifunctional (meth)acrylate monomer having a molecular weight of 180 or less and having two (meth)acryloyloxy groups in the molecule. From the viewpoint of viscosity reduction, it is preferably a monofunctional (meth)acrylate monomer having a molecular weight of 180 or less.

[0051] Examples of the monofunctional (meth)acrylate monomer having a molecular weight of 180 or less include compounds having a molecular weight of 180 or less among the compounds described as the above monofunctional (meth)acrylate monomers. The monofunctional (meth)acrylate monomer having a molecular weight of 180 or less is preferably at least one compound selected from (meth)acrylic acid alkyl esters having a molecular weight of 180 or less, (meth)acrylic acid aryl esters having a molecular weight of 180 or less, and (meth)acrylic acid aralkyl esters having a molecular weight of 180 or less.

[0052] Examples of the alkyl (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, and hexyl (meth)acrylate. Examples of the aryl (meth)acrylate include phenyl (meth)acrylate. Examples of the aralkyl (meth)acrylate include benzyl (meth)acrylate.

[0053] The hydrogen atom of the alkyl group in the alkyl (meth)acrylate, the hydrogen atom of the aryl group in the aryl (meth)acrylate, and the hydrogen atom of the aralkyl group in the aralkyl (meth)acrylate may be substituted with substituents such as a hydroxy group, an amino group, and an alkoxy group (preferably a C 1-4 alkoxy group), etc., but it is preferably unsubstituted as long as the molecular weight of the compound does not exceed 180.

[0054] The compound (C1) is preferably an alkyl (meth)acrylate having a molecular weight of 180 or less, more preferably a C 1-4 alkyl (meth)acrylate, and particularly preferably ethyl (meth)acrylate. Further, the molecular weight of the compound (C1) is preferably 160 or less, more preferably 150 or less, still more preferably 140 or less, and for example, 86 or more.

[0055] The compound (C1) preferably has a viscosity at 25°C of 2.5 cP or less, more preferably 2.0 cP or less, still more preferably 1.2 cP or less, particularly preferably 1.0 cP or less, most preferably 0.8 cP or less, and for example, 0.1 cP or more.

[0056] When the photopolymerizable compound (C) contains the compound (C1), its content is preferably 5% by mass or more, more preferably 15% by mass or more, still more preferably 25% by mass or more, particularly preferably 30% by mass or more, with respect to the total amount of the photopolymerizable compound (C), and is preferably 75% by mass or less, more preferably 60% by mass or less, still more preferably 55% by mass or less, particularly preferably 50% by mass or less. Also, when the photopolymerizable compound (C) contains the compound (C1), its content is preferably 5% by mass or more, more preferably 8% by mass or more, still more preferably 10% by mass or more, particularly preferably 13% by mass or more, most preferably 17% by mass or more, with respect to the total amount of the photosensitive composition, and is preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less.

[0057] The photopolymerizable compound (C) preferably contains a compound (C2) (hereinafter sometimes simply referred to as "compound (C2)") having a vinyl ether group and a (meth)acryloyl group (preferably a (meth)acryloyloxy group) in the same molecule. When the photosensitive composition contains the compound (C2), aggregation of semiconductor particles can be suppressed, the dispersibility of the semiconductor particles is improved, and as a result, the photoconversion efficiency of the cured film obtained from the photosensitive composition is further improved. Further, when the photosensitive composition contains the compound (C2), the viscosity of the photosensitive composition can be reduced and the coatability is further improved.

[0058] The number of vinyl ether groups in the compound (C2) is preferably 1 or more and 4 or less, more preferably 1 or more and 2 or less, particularly preferably 1. The number of (meth)acryloyl groups in the compound (C2) is preferably 1 or more and 4 or less, more preferably 1 or more and 2 or less, particularly preferably 1.

[0059] Examples of the compound (C2) include 2-vinyloxyethyl (meth)acrylate, 3-vinyloxypropyl (meth)acrylate, 2-vinyloxypropyl (meth)acrylate, 1-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxyethyl (meth)acrylate, 4-vinyloxybutyl (meth)acrylate, 3-vinyloxybutyl (meth)acrylate, 2-vinyloxybutyl (meth)acrylate, 1-methyl-3-vinyloxypropyl (meth)acrylate, 2-methyl-3-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxypropyl (meth)acrylate, 1,1-dimethyl-2-vinyloxyethyl (meth)acrylate, 6-vinyloxyhexyl (meth)acrylate, 4-vinyloxycyclohexyl (meth)acrylate, (4-vinyloxymethylcyclohexyl)methyl (meth)acrylate, (3-vinyloxymethylcyclohexyl)methyl (meth)acrylate, (2-vinyloxymethylcyclohexyl)methyl (meth)acrylate, (4-vinyloxymethylphenyl)methyl (meth)acrylate, (3-vinyloxymethylphenyl)methyl (meth)acrylate, 2-vinyloxymethylphenylmethyl (meth)acrylate, 2-(2-vinyloxyisopropoxy)ethyl (meth)acrylate, 2-(2-vinyloxyethoxy)ethyl (meth)acrylate, 2-(2-vinyloxyethoxy)propyl (meth)acrylate, 2-(2-vinyloxyisopropoxy)propyl (meth)acrylate, 2-(2-vinyloxyethoxy)isopropyl (meth)acrylate, 2-(2-vinyloxyisopropoxy)isopropyl (meth)acrylate, 2-{2-(2-vinyloxyethoxy)ethoxy}ethyl (meth)acrylate, 2-{2-(2-vinyloxyisopropoxy)ethoxy}ethyl (meth)acrylate, 2-{2-(2-vinyloxyisopropoxy)isopropoxy}ethyl (meth)acrylate, 2-{2-(2-vinyloxyethoxy)ethoxy}propyl (meth)acrylate, 2-{2-(2-vinyloxyethoxy)isopropoxy}propyl (meth)acrylate, 2-{2-(2-vinyloxyisopropoxy)ethoxy}propyl (meth)acrylate, 2-{2-(2-vinyloxyisopropoxy)isopropoxy}propyl (meth)acrylate(Meth)acrylic acid 2-{2-(2-vinyloxyethoxy)ethoxy}isopropyl, (meth)acrylic acid 2-{2-(2-vinyloxyethoxy)isopropoxy}isopropyl, (meth)acrylic acid 2-{2-(2-vinyloxyisopropoxy)ethoxy}isopropyl, (meth)acrylic acid 2-{2-(2-vinyloxyisopropoxy)isopropoxy}isopropyl, (meth)acrylic acid 2-[2-{2-(2-vinyloxyethoxy)ethoxy}ethoxy]ethyl, (meth)acrylic acid 2-[2-{2-(2-vinyloxyisopropoxy)ethoxy}ethoxy]ethyl, (meth)acrylic acid 2-(2-[2-{2-(2-vinyloxyethoxy)ethoxy}ethoxy]ethoxy)ethyl, etc. may be mentioned.

[0060] As the compound (C2), vinyloxy C (meth)acrylate 1-6 alkyl or (meth) (Vinyloxy C (meth)acrylate 1-4 (alkoxy)C 1-4 alkyl is preferred, and (vinyloxy C (meth)acrylate 1-4 (alkoxy)C 1-4 alkyl is more preferred, and 2-(2-vinyloxyethoxy)ethyl (meth)acrylate is particularly preferred.

[0061] When the photopolymerizable compound (C) contains the compound (C2), its content is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, based on the total amount of the photopolymerizable compound (C), and preferably 85% by mass or less, more preferably 75% by mass or less, still more preferably 60% by mass or less, particularly preferably 50% by mass or less, and most preferably 40% by mass or less. Also, when the photopolymerizable compound (C) contains the compound (C2), its content is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 8% by mass or more, based on the total amount of the photosensitive composition, and preferably 50% by mass or less, more preferably 35% by mass or less, still more preferably 25% by mass or less.

[0062] The photopolymerizable compound (C) preferably contains a compound (C3) (hereinafter sometimes simply referred to as "compound (C3)") having a carboxyl group and three or more functional groups other than the carboxyl group in the same molecule. When the photosensitive composition contains the compound (C3), aggregation of semiconductor particles can be suppressed, the dispersibility of the semiconductor particles is improved, and as a result, the photoconversion efficiency of the cured film obtained from the photosensitive composition is further improved. Further, when the photosensitive composition contains the compound (C3), the curability of the photosensitive composition is improved. Furthermore, when the photosensitive composition contains the compound (C3), the heat resistance of the photosensitive composition is further improved. In particular, when the photosensitive composition contains the compound (C3) and a stabilizer (E) in an amount of 8% by mass or more based on the total amount of the photosensitive composition, the heat resistance of the photosensitive composition is further improved.

[0063] Examples of the functional group include a (meth)acryloyloxy group, an epoxy group, an oxetane group, etc., and among them, a (meth)acryloyloxy group is preferable. The number of functional groups possessed by one molecule of the compound (C3) is preferably 3 to 5, and more preferably 3. The number of carboxyl groups possessed by one molecule of the compound (C3) is preferably 1.

[0064] Examples of the compound (C3) include compounds obtained by esterifying a compound having three or more functional groups (particularly a (meth)acryloyloxy group) and a hydroxy group, such as pentaerythritol tri(meth)acrylate or dipentaerythritol penta(meth)acrylate, with a dicarboxylic acid. Specifically, for example, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and succinic acid, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and maleic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and maleic acid, etc. are mentioned. Among them, a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid is preferable.

[0065] When the photopolymerizable compound (C) contains the compound (C3), its content is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, and preferably 70% by mass or less, more preferably 60% by mass or less, still more preferably 50% by mass or less, and particularly preferably 40% by mass or less, based on the total amount of the photopolymerizable compound (C). When the photopolymerizable compound (C) contains the compound (C3), its content is preferably 20 parts by mass or more, more preferably 25 parts by mass or more, still more preferably 30 parts by mass or more, and particularly preferably 40 parts by mass or more, and preferably 110 parts by mass or less, more preferably 100 parts by mass or less, still more preferably 85 parts by mass or less, and particularly preferably 70 parts by mass or less, based on 100 parts by mass of the semiconductor particles (A).

[0066] The photopolymerizable compound (C) preferably contains at least one compound selected from the compound (C1), the compound (C2), and the compound (C3), more preferably contains at least the compound (C3), still more preferably contains a combination of the compound (C3) and the compound (C2) or a combination of the compound (C3) and the compound (C1), and particularly preferably contains all of the compound (C1), the compound (C2), and the compound (C3).

[0067] When the photopolymerizable compound (C) contains the compound (C1) and the compound (C3), the content of the compound (C1) relative to 1 part by mass of the compound (C3) is preferably 0.5 part by mass or more, more preferably 0.8 part by mass or more, still more preferably 1.0 part by mass or more, and preferably 5 parts by mass or less, more preferably 4 parts by mass or less, still more preferably 3 parts by mass or less. When the photopolymerizable compound (C) contains the compound (C2) and the compound (C3), the content of the compound (C2) relative to 1 part by mass of the compound (C3) is preferably 0.3 part by mass or more, more preferably 0.5 part by mass or more, still more preferably 0.8 part by mass or more, and preferably 5 parts by mass or less, more preferably 3 parts by mass or less, still more preferably 1.5 parts by mass or less. When the photopolymerizable compound (C) contains the compound (C1), the compound (C2), and the compound (C3), the total amount of the compound (C1) and the compound (C2) with respect to 1 part by mass of the compound (C3) is preferably 0.5 part by mass or more, more preferably 1.0 part by mass or more, still more preferably 1.5 part by mass or more, and is preferably 5 parts by mass or less, more preferably 4 parts by mass or less, still more preferably 3 parts by mass or less.

[0068] The total amount of the compound (C1), the compound (C2), and the compound (C3) is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 70% by mass or more, particularly preferably 90% by mass or more, and may be 100% by mass, with respect to the total amount of the photopolymerizable compound (C). In particular, when the photopolymerizable compound (C) contains the compound (C1) and the compound (C3), the total amount of the compound (C1) and the compound (C3) is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 60% by mass or more, particularly preferably 70% by mass or more, and may be 100% by mass, with respect to the total amount of the photopolymerizable compound (C). Also, when the photopolymerizable compound (C) contains the compound (C2) and the compound (C3), the total amount of the compound (C2) and the compound (C3) is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, particularly preferably 60% by mass or more, and may be 100% by mass, and is preferably 90% by mass or less, more preferably 80% by mass or less, with respect to the total amount of the photopolymerizable compound (C).

[0069] The content of the photopolymerizable compound (C) is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, particularly preferably 40% by mass or more, and is preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 65% by mass or less, particularly preferably 60% by mass or less, with respect to the total amount of the photosensitive composition.

[0070] <Photopolymerization initiator (D)> The photoinitiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light and initiate polymerization, and known photoinitiators can be used.

[0071] Examples of the photoinitiator (D) include oxime compounds such as O-acyl oxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, acylphosphine oxide compounds, and the like.

[0072] The O-acyl oxime compound is a compound having a structure represented by the following formula (d). Hereinafter, * represents a bond.

[0073]

Chemical formula

[0074] Examples of such O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetoxy-1-[4-(1-methyl-2-methoxyethoxy)-2-methylphenyl]-1-(9-ethyl-6-nitro-9H-carbazol-3-yl)methan-1-imine, and the like. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02, OXE03 (manufactured by BASF), N-1919, NCI-930, NCI-831 (manufactured by ADEKA) may also be used. These O-acyl oxime compounds are advantageous in that they can improve lithography performance.

[0075] The alkylphenone compound is a compound having a partial structure represented by the following formula (d4) or a partial structure represented by the following formula (d5). In these partial structures, the benzene ring may have a substituent.

[0076]

Chemical formula

[0077] Examples of the compound having the structure represented by the formula (d4) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl) phenyl]butan-1-one, etc. Commercially available products such as OMNIRAD (registered trademark) 369, 907, 379 (manufactured by IGM Resins) may also be used.

[0078] Examples of the compound having the structure represented by the formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzyldimethyl ketal, etc.

[0079] In terms of sensitivity, as the alkylphenone compound, the compound having the structure represented by the formula (d4) is preferred.

[0080] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), an imidazole compound in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboxyalkoxy groups (see, for example, JP-A-7-10913), and the like. Among them, a compound represented by the following formula or a mixture thereof is preferable.

[0081] [Chemical formula]

[0082] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0083] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.

[0084] Furthermore, examples of the photopolymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds, and the like. These are preferably used in combination with polymerization initiation aids such as amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0085] As the photopolymerization initiator (D), a photopolymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds is preferable, and a photopolymerization initiator containing an alkylphenone compound is more preferable from the viewpoint of sensitivity.

[0086] The content of the photopolymerization initiator (D) is preferably 3% by mass or more, more preferably 4% by mass or more, and preferably 40% by mass or less, more preferably 30% by mass or less, and may be 20% by mass or less, or may be 15% by mass or less, based on the total amount of the photosensitive composition. The content of the photopolymerization initiator (D) is preferably 3 parts by mass or more, more preferably 8 parts by mass or more, and preferably 70 parts by mass or less, more preferably 55 parts by mass or less, still more preferably 30 parts by mass or less, and may be 20 parts by mass or less, based on 100 parts by mass of the photopolymerizable compound (C). When the content of the photopolymerization initiator (D) is within the above range, the sensitivity tends to increase and the exposure time tends to be shortened, so the productivity of a cured film such as a wavelength conversion film tends to improve. Also, the content of the photopolymerization initiator (D) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and still more preferably 25 parts by mass or less, based on 100 parts by mass of the photopolymerizable compound (C). When the content of the photopolymerization initiator (D) is within the above range, a photosensitive composition with a lower viscosity can be provided. Furthermore, it is also preferable that the content of the photopolymerization initiator (D) is, for example, 15 parts by mass or more and 40 parts by mass or less, more preferably 15 parts by mass or more and 30 parts by mass or less, still more preferably 15 parts by mass or more and 25 parts by mass or less, based on 100 parts by mass of the photopolymerizable compound (C). When the content of the photopolymerization initiator (D) is within the above range, a photosensitive composition capable of providing a cured film with more excellent heat resistance can be provided.

[0087] <Stabilizer (E)> The photosensitive composition of the present invention may further contain a stabilizer (E). The stabilizer (E) is not particularly limited as long as it is a compound having a function of inactivating deterioration factors such as carbon radicals generated by the action of heat, light, etc., peroxy radicals generated by the oxidation of the generated carbon radicals, and hydroperoxides generated from peroxy radicals. Examples thereof include antioxidants, light stabilizers, and the like.

[0088] The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and phenolic antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like can be used.

[0089] Examples of phenolic antioxidants include Irganox (registered trademark) 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), 1076 (Irganox 1076: octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, manufactured by BASF Corporation), 1330 (Irganox 1330: 3,3’,3’’,5,5’,5’’-hexa-t-butyl-a,a’,a’’-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF Corporation), 3114 (Irganox 3114: 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), 3790 (Irganox 3790: 1,3,5-tris((4-t-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), 1035 (Irganox 1035: thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF Corporation), 1135 (Irganox 1135: benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF Corporation), 1520L (Irganox 1520L: 4,6-bis(octylthiomethyl)-o-cresol, manufactured by BASF Corporation), 3125 (Irganox 3125, manufactured by BASF Corporation), 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy 3’,5’-di-t-butylanilino)-1,3,5-triazine, manufactured by BASF Corporation), Adeka Stab (registered trademark) AO-80 (Adeka Stab AO-80: 3,9-bis(2-(3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5) Undecane (manufactured by ADEKA CORPORATION), Sumilizer (registered trademark) BHT, GA-80, GS (all manufactured by Sumitomo Chemical Company, Limited), Cyanox (registered trademark) 1790 (Cyanox 1790, manufactured by Cytec Industries Inc.), vitamin E (manufactured by Eisai Co., Ltd.), and the like.

[0090] As the phenolic antioxidant, an antioxidant having a hindered phenol structure in which a bulky organic group is bonded to at least one ortho position of the phenolic hydroxy group is preferable. As the bulky organic group, a secondary or tertiary alkyl group is preferable, and specifically, an isopropyl group, s-butyl group, t-butyl group, s-amyl group, t-amyl group, etc. may be mentioned. Among them, a tertiary alkyl group is preferable, and a t-butyl group or t-amyl group is particularly preferable.

[0091] Examples of the phosphorus-based antioxidant include Irgafos (registered trademark) 168 (Irgafos 168: tris(2,4-di-t-butylphenyl) phosphite, manufactured by BASF SE), 12 (Irgafos 12: tris[2-[[2,4,8,10-tetra-t-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl]amine, manufactured by BASF SE), 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF SE), Adeka Stab (registered trademark) 329K, PEP36, PEP-8 (all manufactured by ADEKA CORPORATION), Sandstab P-EPQ (manufactured by Clariant), Weston (registered trademark) 618, 619G (both manufactured by GE), Ultranox626 (manufactured by GE), and Sumilizer (registered trademark) GP (6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1.3.2]dioxaphosphepine) (manufactured by Sumitomo Chemical Company, Limited), and the like.

[0092] As the phosphorus-based antioxidant, an antioxidant having a group represented by the following formula (e1) is preferable.

[0093] [Chemical formula] [In formula (e1), R e1 ~R e5 each independently represents a hydrogen atom or an alkyl group, and * represents a bond.]

[0094] R e1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group, an ethyl group, or a t-butyl group. R e2 and R e4 are preferably a methyl group or a hydrogen atom, more preferably a hydrogen atom. R e5 and R e3 each independently are preferably an alkyl group, more preferably a secondary or tertiary alkyl group, and even more preferably a t-butyl group or a t-amyl group. The two units enclosed in parentheses may be bonded to each other to form a ring. The bonding of R e1 to each other refers to the mode in which the groups excluding the hydrogen atom from R e1 are bonded to each other. For example, when both of the two R e1 are hydrogen atoms, it refers to the mode in which the carbon atom to which R e1 in one benzene ring is bonded and the carbon atom to which R e1 in the other benzene ring is bonded are directly bonded to each other. e1

[0095] Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate, or distearyl thiodipropionate, and polyol β-alkyl mercaptopropionate ester compounds such as tetrakis[methylene(3-dodecylthio)propionate]methane.

[0096] As the light stabilizer, there is no particular limitation as long as it is a light stabilizer generally used industrially. For example, hindered amine light stabilizers and the like can be used. Examples of the hindered amine light stabilizers include AdekaStab (registered trademark) LA-52, LA-57, LA-63P, LA-68, LA-72, LA-77Y, LA-77G, LA-81, LA-82, LA-87, LA-402AF, LA-40MP, LA-40Si (all manufactured by ADEKA CORPORATION), Chimassorb (registered trademark) 944FDL, 2020FDL, TINUVIN622SF (all manufactured by BASF), and the like.

[0097] As the stabilizer (E), an antioxidant is preferable, a phenolic antioxidant or a phosphorus-based antioxidant is more preferable, and it is more preferable that it is an antioxidant having at least one of the above-mentioned hindered phenol structure and the group represented by the formula (e1), and it is even more preferable that it is an antioxidant having both the above-mentioned hindered phenol structure and the group represented by the formula (e1), and Sumilizer (registered trademark) GP is particularly preferable.

[0098] The content of the stabilizer (E) is, for example, 1% by mass or more, may be 2% by mass or more, and may be, for example, 60% by mass or less, preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, based on the total amount of the photosensitive composition. From the viewpoint of improving heat resistance, the content of the stabilizer (E) is preferably 8% by mass or more, more preferably 9% by mass or more, still more preferably 12% by mass or more, and particularly preferably 16% by mass or more, based on the total amount of the photosensitive composition. Also, from the viewpoint of reducing viscosity, the content of the stabilizer (E) may be, for example, 60% by mass or less, preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, even more preferably 20% or less, and particularly preferably 18% by mass or less, based on the total amount of the photosensitive composition.

[0099] <Solvent (F)> The photosensitive composition of the present invention may contain a solvent (F). When it contains the solvent (F), it is preferable that the content thereof is small. When the photosensitive composition contains the solvent (F), the content thereof is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3.5% by mass or less, particularly preferably 3.2% by mass or less, based on the total amount of the photosensitive composition. It may also be 0% by mass, may be 0.5% by mass or more, or may be 1% by mass or more. By reducing the content of the solvent (F), it becomes easy to control the film thickness when forming a cured film, and it is also possible to reduce the production cost and the load on the global environment and the working environment due to the solvent.

[0100] Examples of the solvent (F) include ester solvents (solvents containing -C(=O)-O-), ether solvents other than ester solvents (solvents containing -O-), ether ester solvents (solvents containing -C(=O)-O- and -O-), ketone solvents other than ester solvents (solvents containing -C(=O)-), alcohol solvents, aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

[0101] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and γ-butyrolactone.

[0102] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

[0103] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate, and the like.

[0104] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0105] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0106] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0107] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0108] As the solvent (F), an ester solvent, an ether ester solvent, an alcohol solvent, or an amide solvent is preferable, and an ether ester solvent is more preferable.

[0109] <Leveling agent (G)> The photosensitive composition of the present invention may further contain a leveling agent (G). Examples of the leveling agent (G) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms. These may have a polymerizable group in the side chain.

[0110] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan G.K.) etc. can be mentioned.

[0111] Examples of fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.) etc. can be mentioned.

[0112] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation) etc. can be mentioned.

[0113] The content of the leveling agent (G) is usually 0.001% by mass or more and 0.5% by mass or less, preferably 0.005% by mass or more and 0.3% by mass or less, more preferably 0.01% by mass or more and 0.2% by mass or less with respect to the total amount of the photosensitive composition.

[0114] The photosensitive composition of the present invention is a photosensitive composition containing semiconductor particles (A), a photopolymerizable compound (C), and a photopolymerization initiator (D), wherein the photopolymerizable compound (C) contains the compound (C1) and / or the compound (C2), or contains a stabilizer (E) of 8% by mass or more based on the total amount of the photosensitive composition. The photosensitive composition of the present invention preferably contains all of the compound (C1), the compound (C2), and a stabilizer (E) in a predetermined amount or more. When the photosensitive composition contains the compound (C1) and / or the compound (C2), the viscosity of the photosensitive composition can be reduced. Also, when the photosensitive composition contains the compound (C1) and / or the compound (C2), the heat resistance may be likely to decrease, but by adding a stabilizer (E) in a predetermined amount or more, the decrease in heat resistance can be suppressed. The photosensitive composition preferably further contains a compound (C3). By including the compound (C3) in the photosensitive composition, aggregation of the semiconductor particles can be suppressed, the dispersibility of the semiconductor particles is improved, and as a result, the photoconversion efficiency of the cured film obtained from the photosensitive composition is further improved. When the photosensitive composition contains the compound (C3), the viscosity of the photosensitive composition may tend to increase, but since the photosensitive composition contains the compound (C1) and / or the compound (C2), this increase in viscosity is suppressed. Also, when the compound (C1) and / or the compound (C2) are included to reduce the viscosity, the heat resistance may be likely to decrease, but as described above, since a stabilizer (E) in a predetermined amount or more is contained, the decrease in heat resistance can be suppressed. Furthermore, the content of the semiconductor particles (A) in the photosensitive composition is preferably 16% by mass or more and 45% by mass or less based on the total amount of the photosensitive composition. When the content of the semiconductor particles (A) is within the above range, sufficient photoconversion efficiency can be obtained in the cured film.

[0115] The viscosity of the photosensitive composition of the present invention at 40°C is preferably 20 cP or less, more preferably 15 cP or less, and even more preferably 10 cP or less. The lower limit is not particularly limited, and it may be 2 cP or more, 3 cP or more, or 5 cP or more. By setting the viscosity of the photosensitive composition within the above range, the coating property is improved. In particular, by setting the viscosity of the photosensitive composition within the above range, the photosensitive composition can be smoothly discharged from the discharge head of an inkjet printer and can be suitably used as an ink for an inkjet printer.

[0116] When used as an ink for an inkjet printer, the photosensitive composition of the present invention can be discharged from the discharge head of an inkjet printer at a temperature of 40°C or higher. Among the photosensitive compositions of the present invention, some have excellent heat resistance, and even when the temperature of the photosensitive composition is discharged under the condition of 40°C or higher, the physical properties (especially the light conversion efficiency) of the obtained cured film are good. The temperature of the photosensitive composition when discharged from the discharge head of an inkjet printer may be 50°C or higher, 60°C or higher, or 80°C or lower.

[0117] As other components, the photosensitive composition of the present invention may be used with additives such as a dispersant, a plasticizer, and a filler as needed.

[0118] Examples of the dispersant include, but are not limited to, surfactants such as cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based, and acrylic-based surfactants. The dispersant is preferably used in combination when the photosensitive composition contains a light scattering agent (B). By containing a dispersant in the photosensitive composition, the dispersibility of the light scattering agent (B) in the photosensitive composition is improved.

[0119] When the photosensitive composition contains a dispersant, its content is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less, particularly preferably 1% by mass or less, based on the total amount of the photosensitive composition. Also, it may be 0% by mass, may be 0.1% by mass or more, or may be 0.3% by mass or more. Further, from the viewpoint of reducing viscosity, it is preferably 3% by mass or less, more preferably 2% by mass or less, particularly preferably 1% by mass or less.

[0120] Also, the content of the additive is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less, particularly preferably 1% by mass or less, based on the total amount of the photosensitive composition. Also, it may be 0% by mass.

[0121] <Method for producing a photosensitive composition> The photosensitive composition of the present invention can be prepared by mixing semiconductor particles (A), a photopolymerizable compound (C), a photopolymerization initiator (D), and, if necessary, a light-scattering agent (B), a stabilizer (E), a solvent (F), a leveling agent (G), and other additives.

[0122] The mixing order of each component is not particularly limited, but it is preferable to first prepare a dispersion obtained by mixing semiconductor particles (A) and a photopolymerizable compound (C), and a light-scattering agent solution obtained by mixing a light-scattering agent (B) and a solvent (F), and then mix the obtained dispersion, light-scattering agent solution, and other components.

[0123] The ligand-containing semiconductor particles as the semiconductor particles (A) may be, for example, semiconductor particles having an organic ligand coordinated thereto, and then subjected to a ligand reduction treatment for reducing the coordination amount of the organic ligand to the semiconductor particles. The ligand reduction treatment can be, for example, a treatment for extracting the organic ligand coordinated to the semiconductor particles with an appropriate solvent.

[0124] <Cured film, patterned cured film, wavelength conversion film and display device> A cured film can be obtained by curing a film (layer) composed of a photosensitive composition. Specifically, a photosensitive composition is applied onto a substrate to form a coated film, and the obtained coated film is exposed to obtain a cured film.

[0125] As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate, silicon, and those with aluminum, silver, silver / copper / palladium alloy thin films, etc. formed on the above substrates can be used.

[0126] For the application of the photosensitive composition, various printing methods such as gravure printing method, offset printing method, letterpress printing method, screen printing method, transfer printing method, electrostatic printing method, and digital printing method, as well as coating methods such as gravure coating method, roll coating method, knife coating method, air knife coating method, bar coating method, dip coating method, kiss coating method, spray coating method, die coating method, comma coating method, inkjet method, spin coating method, and slit coating method, and methods combining these can be appropriately used.

[0127] As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less is preferable. For example, light with a wavelength of less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, or near 365 nm can be selectively extracted using a band-pass filter that extracts these wavelength ranges. Examples of the light source include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0128] Also, a patterned cured film can be formed from the photosensitive composition by patterning using methods such as photolithography, inkjet method, and printing method. In the photolithography method, loss of expensive composition materials occurs. Therefore, from the perspective of reducing material loss, it is preferable to adopt the inkjet method.

[0129] As a method for manufacturing a cured film patterned by an inkjet method, for example, after forming a bank on a substrate, a photosensitive composition is selectively adhered to a region partitioned by the bank on the substrate by the inkjet method, and the photosensitive composition is cured by exposure.

[0130] As the substrate, the substrate exemplified in the description of the method for manufacturing the cured film can be used.

[0131] Examples of the method for forming the bank include a photolithography method and an inkjet method, and it is preferable to form the bank by the inkjet method.

[0132] Examples of the inkjet method include a bubble jet (registered trademark) method using an electrothermal converter as an energy generating element, or a piezo jet method using a piezoelectric element.

[0133] As the light source used for exposure, the light source exemplified in the description of the method for manufacturing the cured film can be used.

[0134] The non-patterned cured film or the patterned cured film can be suitably used as a wavelength conversion film (wavelength conversion filter) that emits light having a wavelength different from the wavelength of light incident from a light emitting portion such as an LED. In particular, the patterned cured film is preferably positioned above a light emitting element such as an LED corresponding to each pattern. By wavelength-converting each light emitting element individually, the shape of the emission spectrum such as red, green, and blue can be appropriately adjusted, and high color reproducibility can be achieved. A display member having a wavelength conversion film can be suitably used for display devices such as liquid crystal display devices and organic EL devices.

[0135] FIG. 1 is a schematic cross-sectional view of an embodiment of a display member formed by an inkjet method. The display member 10 in FIG. 1 has a bank 2 formed on a substrate 1 and a light-emitting element 3 such as an LED installed between the banks 2. After the photosensitive composition of the present invention is adhered onto the light-emitting element 3 between the banks 2 by an inkjet method and then cured, a cured film 4 (wavelength conversion film) is obtained (hereinafter, each cured film patterned to the size between the banks 2 may be referred to as a "cured film pixel"). A color filter 5, a gas barrier layer 6, etc. may be positioned on each cured film pixel 4.

[0136] By forming the cured film pixel 4 by an inkjet method, patterning with a relatively large size becomes possible, and it can be suitably applied to large displays such as digital signage. Therefore, when adopting the inkjet method, the vertical dimension (L1) of the cured film pixel 4 formed from the photosensitive composition of the present invention is preferably 9 μm or more, more preferably 12 μm or more, still more preferably 15 μm or more, and may be 40 μm or less, or may be 30 μm or less. Note that the vertical dimension (L1) may be the same length as the horizontal dimension (L3) of the light-emitting element. Also, when adopting the inkjet method, the horizontal dimension (L2) of the cured film pixel 4 formed from the photosensitive composition of the present invention is preferably 10 μm or more, more preferably 30 μm or more, still more preferably 50 μm or more, even more preferably 80 μm or more, particularly preferably 100 μm or more, and may be 900 μm or less, may be 800 μm or less, or may be 700 μm or less.

[0137] Note that the vertical dimension (L1) of the cured film pixel 4 is the dimension in the base material thickness direction in a cross-section cut out in a direction perpendicular to the substrate. The cross-section is cut out at a location where the vertical dimension of the cured film pixel 4 is the largest. FIG. 1 shows a cross-section cut out in a direction perpendicular to the base material at a location where the vertical dimension of the cured film pixel 4 is the largest. The horizontal dimension (L2) of the above-mentioned cured film pixel 4 is the maximum dimension of the cured film pixel 4 in the direction horizontal to the substrate, and refers to the dimension (plan view dimension) when viewing the substrate from the vertical direction. The horizontal dimension (L3) of the light-emitting element is the maximum dimension of the light-emitting element in the direction horizontal to the substrate, and refers to the dimension (plan view dimension) when viewing the substrate from the vertical direction.

[0138] Note that the fact that the stabilizer (E) is contained in the cured film can be confirmed by analyzing the cured film by thermal desorption GC / MS. As the thermal desorption conditions and detection conditions of the stabilizer (E), the conditions described in the following examples can be used. When performing thermal desorption GC / MS on the cured film, it can be confirmed that the stabilizer (E) is contained in the cured film by the appearance of the MS spectrum due to the specific molecular structure of the stabilizer (E).

Examples

[0139] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited by the following examples, and it is of course possible to appropriately modify and implement it within the range that can conform to the gist of the foregoing and following descriptions, and all of them are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0140] In the experimental examples and comparative examples, the following materials were used. · Quantum dot dispersion liquid 1: A toluene dispersion liquid of quantum dots having an InP / ZnSeS structure and containing an organic ligand (maximum peak wavelength of the emission spectrum: 530 nm, full width at half maximum: 42 nm) · Quantum dot dispersion liquid 2: A toluene dispersion liquid of quantum dots having an InP / ZnSeS structure and containing an organic ligand (maximum peak wavelength of the emission spectrum: 630 nm, full width at half maximum: 42 nm) · Photopolymerizable compound (C3-1): Pentaerythritol succinic acid monoester · Photopolymerizable compound (C-2): ω-carboxy-polycaprolactone (n≈2) monoacrylate (Aronix (registered trademark) M-5300, manufactured by Toagosei Co., Ltd.) · Photopolymerizable compound (C-3): Glycerol triacrylate (Aronix (registered trademark) MT-3547, manufactured by Toagosei Co., Ltd.) · Photopolymerizable compound (C-4): Isobornyl acrylate · Photopolymerizable compound (C2-5): 2-(2-Vinyloxyethoxy)ethyl acrylate (VEEA (registered trademark), manufactured by Nippon Shokubai Co., Ltd.) · Photopolymerizable compound (C1-6): Ethyl methacrylate (Light Ester E, manufactured by Kyoeisha Chemical Co., Ltd., viscosity at 25°C: 0.7 cP) · Photoinitiator (D-1): OMNIRAD (registered trademark) 907, manufactured by IGM Resins · Photoinitiator (D-2): OMNIRAD (registered trademark) 369, manufactured by IGM Resins · Stabilizer (E-1): Sumilizer (registered trademark) GP, manufactured by Sumitomo Chemical Co., Ltd. · Solvent (F-1): Propylene glycol monomethyl ether acetate (hereinafter referred to as PGMEA) · Levelling agent (G-1): Megafac (registered trademark) F-554, manufactured by DIC Corporation

[0141] <Preparation of Quantum Dot 1> Toluene was removed from the quantum dot dispersion liquid 1 by vacuum distillation to obtain a dried product of quantum dot 1.

[0142] <Preparation of Quantum Dot 2> Toluene was removed from the quantum dot dispersion liquid 2 by vacuum distillation to obtain a dried product of quantum dot 2.

[0143] <Preparation of Light Scattering Agent Solution> 60 parts of titanium oxide particles (median diameter 0.23 μm based on volume), 10 parts of dispersant (in terms of solid content), and a total of 30 parts of PGMEA were mixed, and the titanium oxide particles were sufficiently dispersed using a bead mill.

[0144] <Experimental Example 1> The photopolymerizable compound described in Table 1 was added to the above quantum dots 1, and the mixture was stirred with an ultrasonic cleaner and a touch mixer until the solid matter disappeared, thereby obtaining a quantum dot monomer dispersion. To the obtained dispersion, a light scattering agent solution, a photopolymerization initiator, a stabilizer, and a leveling agent were added so as to have the formulation described in Table 1, and the mixture was stirred with a touch mixer to obtain quantum dot ink.

[0145] <Experimental Examples 2 to 14, Comparative Examples 1 to 3> Quantum dot ink was obtained in the same manner as in Experimental Example 1, except that the types and amounts of the semiconductor particles, light scattering agent, photopolymerizable compound, photopolymerization initiator, stabilizer, leveling agent, and solvent were changed to the formulations described in Table 1.

[0146]

Table 1

[0147] <Evaluation Test> (1) Curing Property Test The quantum dot ink was applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by spin coating, and then irradiated with light at an exposure amount of 200 mJ / cm 2 (standard for 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). When a cured film was obtained after light irradiation, it was marked as ○, and when it remained liquid after light irradiation, it was marked as ×. The results are shown in Table 1.

[0148] (2) Measurement of External Quantum Yield The Incident photon number was evaluated using the optical system 10a described in FIG. 2. In the optical system 10a, a light diffusing plate was placed on a substrate on which blue light-emitting diodes having a maximum peak wavelength of 445 nm were arranged, and this was used as the backlight 11a. On this backlight 11a, a glass substrate 12a before coating with a cured film was placed, and an electron-cooled back-surface incident type high S / N fiber multi-channel spectrometer QE65Pro (manufactured by Ocean Optics Co., Ltd.) equipped with an optical fiber was arranged vertically above the substrate surface, and spectrum measurement was performed. The distance between the surface of the substrate 12a and the detector unit 13a of the spectrometer was fixed at 5 cm. The Incident photon number was obtained according to Equation 1 for the obtained spectrum I(λ).

[0149] [Number]

[0150] Next, the Emittied photon number was evaluated using the optical system 10b described in FIG. 3. In the optical system 10b, a light diffusing plate was placed on a substrate on which blue light-emitting diodes having a maximum peak wavelength of 445 nm were arranged, and this was used as the backlight 11b. On this backlight 11b, a substrate 12b having a cured film 14 produced in the above-described curing test was placed, and an electron-cooled back-surface incident type high S / N fiber multi-channel spectrometer QE65Pro (manufactured by Ocean Optics Co., Ltd.) equipped with an optical fiber was arranged vertically above the substrate surface, and spectrum measurement was performed. The distance between the surface of the cured film 14 and the detector unit 13b of the spectrometer was fixed at 5 cm. The Emitted photon number was obtained according to Equation 2 for the obtained spectrum I(λ).

[0151] [Number]

[0152] From the above Incident photon number and Emitted photon number, the external quantum yield was obtained according to Equation 3. When the external quantum yield was less than 20%, it was marked as ×; when it was 20% or more and less than 26%, it was marked as △; when it was 26% or more, it was marked as 〇. The results are shown in Table 1.

[0153]

Number

[0154] (3) Measurement of conversion efficiency The substrate with the cured film prepared in the above-mentioned curability test was cut into 1 cm squares to obtain samples for evaluating the conversion efficiency. For the samples for evaluating the conversion efficiency, the conversion efficiency was measured using an absolute PL quantum yield measurement device (manufactured by Hamamatsu Photonics, product name C9920-02, excitation light 450 nm, room temperature, under atmosphere). When the conversion efficiency was 45% or more, it was marked as 〇; when it was 35% or more and less than 45%, it was marked as △; when it was less than 35%, it was marked as ×. The results are shown in Table 1.

[0155] (4) Measurement of viscosity Using a digital viscometer (model: DV2T) from BROOKFIELD, the viscosity of the quantum dot ink at 40 °C was measured. If the viscosity of the quantum dot ink was less than 14 cP, it was marked as ◎; if it was 14 cP or more and less than 16 cP, it was marked as 〇; if it was 16 cP or more and 20 cP or less, it was marked as △; if it exceeded 20 cP, it was marked as ×. The results are shown in Table 1.

[0156] (5) Heat resistance test The cured film obtained in the above-mentioned curability test was heated in an oven at 80 °C for 3 days. If the conversion efficiency after the heat resistance test was 95% or more of the conversion efficiency before the heat resistance test, it was marked as S; if it was 80% or more and less than 95%, it was marked as A; if it was 50% or more and less than 80%, it was marked as B; if it was less than 50%, it was marked as C. The results are shown in Table 1.

[0157] (6) Detection of stabilizer By thermal desorption GC / MS, the cured films of Experimental Examples 1 to 14 prepared in the above-mentioned curability test were analyzed under the following conditions. Apparatus: 7890B / 5977A (Unit 2) manufactured by Agilent Column: DB-5 (0.25 mm × 30 m, film thickness: 250 mm) Carrier gas: He, 1 mL / min Column temperature: 50 °C (5 min) → 10 °C / min → 320 °C (8 min) Detector: EI, m / z 20 - 600 Inlet temperature: 250 °C AuX temperature: 250 °C Split: 50:1 Sample amount: 300 - 600 mg Thermal desorption conditions: 180 °C (30 min) At this time, a spectral shape similar to the shape that appears when measuring the Sumilizer (registered trademark) GP under the same conditions was confirmed in the cured films of Experimental Examples 1 to 14. It was confirmed that the Sumilizer (registered trademark) GP sublimated under the above thermal desorption conditions based on the appearance of the MS spectrum caused by the specific molecular structure of the Sumilizer (registered trademark) GP.

Explanation of symbols

[0158] 10... Display member 1... Substrate 2... Bank 3... Light-emitting element 4... Cured film (wavelength conversion film) 5... Color filter 6... Gas barrier layer L1... Vertical dimension L2... Horizontal dimension L3... Horizontal dimension of the light-emitting element 10a, 10b... Optical system 11a, 11b... Backlight 12a, 12b... Substrate 13a, 13b... Spectrometer detection unit 14... Cured film

Claims

1. A photosensitive composition comprising semiconductor particles (A), a photopolymerizable compound (C), and a photoinitiator (D), wherein the content of the semiconductor particles (A) is 10% by mass or more based on the total amount of the photosensitive composition, the photopolymerizable compound (C) includes a compound (C3) having a carboxyl group and three or more functional groups other than the carboxyl group in the same molecule, and the viscosity of the photosensitive composition at 40 °C is 20 cP or less. A photosensitive composition.

2. The photosensitive composition according to claim 1, wherein the content of the semiconductor particles (A) is 16% by mass or more and 45% by mass or less based on the total amount of the photosensitive composition.

3. The photosensitive composition according to claim 1 or 2, wherein the content of the photopolymerizable compound (C) is 20% by mass or more and 80% by mass or less based on the total amount of the photosensitive composition.

4. The photosensitive composition according to any one of claims 1 to 3, wherein the content of the compound (C3) is 5% by mass or more based on the total amount of the photopolymerizable compound (C).

5. The photosensitive composition according to any one of claims 1 to 4, wherein the content of the compound (C3) is 25 parts by mass or more and 100 parts by mass or less based on 100 parts by mass of the semiconductor particles (A).

6. The photosensitive composition according to any one of claims 1 to 5, wherein the photosensitive composition further contains a light scattering agent (B) having a volume-based median diameter of 0.15 μm or more.

7. The photosensitive composition according to any one of claims 1 to 6, wherein the photosensitive composition further contains a stabilizer (E).

8. The photosensitive composition according to claim 7, wherein the content of the stabilizer (E) is 8% by mass or more based on the total amount of the photosensitive composition.

9. The photosensitive composition according to claim 8, wherein the content of the stabilizer (E) is 16% by mass or more based on the total amount of the photosensitive composition.

10. The photosensitive composition according to any one of claims 1 to 9, wherein the content of the photoinitiator (D) is 8 parts by mass or more and 55 parts by mass or less based on 100 parts by mass of the photopolymerizable compound (C).

11. The photosensitive composition further contains a solvent (F), and the content of the solvent (F) is 10% by mass or less based on the total amount of the photosensitive composition. The photosensitive composition according to any one of claims 1 to 10.

12. The photosensitive composition further contains a solvent (F), The photosensitive composition according to any one of claims 1 to 10, wherein the content of the solvent (F) is 3.5% by mass or less based on the total amount of the photosensitive composition.

13. The photosensitive composition according to any one of claims 1 to 12, which is an ink for an inkjet printer.

14. Use of the photosensitive composition according to claim 13, which is ejected from a discharge head of an inkjet printer at a temperature of 40 °C or higher.

15. A cured film formed from the photosensitive composition according to any one of claims 1 to 13.

16. The cured film according to claim 15, having a vertical dimension of 9 μm or more and / or a horizontal dimension of 10 μm or more and 900 μm or less.

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