Cerium complex, luminescent solid, resin molded body, and scintillator material

Abstract

One aspect of the present disclosure relates to novel cerium complexes comprising cerium (III) ions and exhibiting strong blue emission.SOLUTION: A cerium complex comprising a cerium (III) ion, a thiocyanate ion, and a coordinating compound that interacts with the cerium (III) ion. The coordination compound is the first compound, the second compound, or a combination of these compounds. The first compound is a base softer than triphenylphosphine oxide in the HSAB rule. The second compound is a base harder than triphenylphosphine oxide in the HSAB rule and has a substituent that suppresses an interaction between the second compound and a cerium (III) ion.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to cerium complexes, luminescent solids, resin molded bodies, and scintillator materials. [Background technology]

[0002] US Pat. No. 5,699,499 discloses a luminescent cerium complex containing cerium(III) ions and organic ligands. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2023-130997 [Non-patent literature]

[0004] [Non-Patent Document 1] Eur. J. Inorg. Chem. 2021, 4273(2021) Summary of the Invention [Problem to be solved by the invention]

[0005] One aspect of the present disclosure relates to novel cerium complexes that contain cerium(III) ions and exhibit strong blue luminescence. [Means for solving the problem]

[0006] The present disclosure includes the following: [1] cerium(III) ions, thiocyanate ion, a coordinating compound that interacts with the cerium (III) ion; A cerium complex comprising: the coordinating compound is a first compound, a second compound, or a combination of the first compound and the second compound; the first compound is a compound that is a softer base than triphenylphosphine oxide according to the HSAB rule, the second compound is a compound that is a harder base than triphenylphosphine oxide according to the HSAB rule and has a substituent that suppresses the interaction between the second compound and the cerium (III) ion; Cerium complexes. [2] cerium(III) ions, thiocyanate ion, a coordinating compound that interacts with the cerium (III) ion; A cerium complex comprising: the coordinating compound is a first compound, a second compound, or a combination of the first compound and the second compound; The first compound is represented by the following formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I), or (1J): [ka] is a compound represented by R 1 , R 2 and R 3 are each independently an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group, or a hydrogen atom, and R 1 , R 2 and R 3 two selected from the group consisting of may be bonded to form a cyclic group, R 4 is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, R 5 is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, R 6 and R 7 are each independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted aryl group, and R6 and R 7 may be bonded to form a cyclic group, R 8 and R 9 are each independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted aryl group, and R 8 and R 9 may be bonded to form a cyclic group, R 10 , R 11 and R 12 are each independently an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group, or a hydrogen atom, and R 10 , R 11 and R 12 two selected from the group consisting of may be bonded to form a cyclic group, R 13 is an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom, R 14 , R 15 and R 16 are each independently an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group, or a hydrogen atom, and R 14 , R 15 and R 16 two selected from the group consisting of may be bonded to form a cyclic group, R 17 and R 18 are each independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted aryl group, and R 17 and R 18 may be bonded to form a cyclic group, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13, R 14 , R 15 , R 16 , R 17 and R 18 may contain a group obtained by removing one or more hydrogen atoms from a compound represented by formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I) or (1J), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 or R 18 is a substituted aliphatic hydrocarbon group, the substituent is a halogeno group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 or R 18 is a substituted aryl group, the substituent is a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group, The second compound is represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K), or (2L): [ka] [ka] [ka] [ka] is a compound represented by Z 1 is -OH, -NH2, or -NO2, Z 2 is -OH, -NH2, -NO2, or -COO - and R 21 and R 25 are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or -COOH, and multiple R 21 and R 25 may be the same or different, R 22 , R 23 and R 24 are each independently a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or -COOH, and multiple R 22 , R 23 and R 24 may be the same or different, R 21 , R 22 , R 23 , R24 and R 25 two selected from the group consisting of may be bonded to form a cyclic group, R 26 , R 30 , R 31 , R 34 , R 35 , R 36 and R 37 each independently represents a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group; R 27 , R 28 , R 29 , R 32 and R 33 each independently represents a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group; R 26 , R 27 , R 28 , R 29 and R 30 two selected from the group consisting of may be bonded to form a cyclic group, and R 31 , R 32 , R 33 , and R 34 two selected from the group consisting of may be bonded to form a cyclic group, R 40 is an alicyclic group which may have a substituent, and multiple R 40 may be the same or different, and R 40 is a substituted alicyclic group, the substituent is a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group, and two R 40 may be bonded to form a cyclic group, R 21 , R 22, R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 and R 40 may contain a group obtained by removing one or more hydrogen atoms from a compound represented by formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K) or (2L). Cerium complexes. [3] The cerium complex according to [2], wherein the coordinating compound is the first compound. [4] The cerium complex according to [2] or [3], wherein the first compound is a compound represented by formula (1A): [5] the first compound is Represented by formula (1B), R 4 is an optionally substituted alkyl group having 2 to 8 carbon atoms, an optionally substituted alkenyl group having 2 to 8 carbon atoms, or an optionally substituted aryl group, or Formula (1B-2) below: [ka] Represented by R 41 is an optionally substituted aliphatic hydrocarbon group or an optionally substituted arylene group. [6] The cerium complex according to [2], wherein the coordinating compound is the second compound. [7] The cerium complex according to [2] or [6], wherein the second compound is a compound represented by formula (2A): [8] A luminescent solid comprising the cerium complex according to any one of [1] to [7]. [9] an organic polymer; The cerium complex according to any one of [1] to [7] above, which is dispersed in the organic polymer; A resin molding material comprising:

[10] ) A scintillator material comprising the cerium complex according to any one of [1] to [7].

[11] The scintillator material according to

[10] , wherein the scintillator material is a resin molded product further containing an organic polymer, and the cerium complex is dispersed in the organic polymer.

[12] The scintillator material according to

[11] , having a thickness of 50 μm or more and 100 μm or less.

[13] The scintillator material according to any one of

[10] to

[12] , which is a scintillator material for measuring α rays. [Effects of the Invention]

[0007] A cerium complex containing cerium(III) ions and exhibiting strong blue luminescence can be provided. The cerium complex according to the present disclosure is resistant to oxidation and has high stability. The emission wavelength can be shifted by changing the type of coordinating compound. [Brief explanation of the drawings]

[0008] [Figure 1] 1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 2] 1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 3] 1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 4] 1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 5] 1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 6]1 shows the ultraviolet-visible absorption spectrum of a cerium complex. [Figure 7] 1 shows the emission spectrum of a cerium complex. [Figure 8] 1 shows the emission spectrum of a cerium complex. [Figure 9] 1 shows the emission spectrum of a cerium complex. [Figure 10] shows the change in the emission intensity of a scintillator material containing a cerium complex due to alpha particles. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention is not limited to the following examples.

[0010] The cerium complex according to the present disclosure includes a cerium(III) ion, a thiocyanate ion, and a coordinating compound that interacts with the cerium(III) ion. The coordinating compound can be a first compound, a second compound, or a combination of these compounds. The first compound is a compound that is a softer base than triphenylphosphine oxide according to the HSAB rule. The second compound is a compound that is a harder base than triphenylphosphine oxide according to the HSAB rule and has a substituent that inhibits the interaction of the second compound with the cerium(III) ion.

[0011] The cerium complex according to the present disclosure is represented, for example, by the following formula (I): In formula (I), L is a coordinating compound, and n is an integer of 1 to 9. - ) forms a coordinate bond with the cerium(III) ion. Ce(III)(SCN)3(L) n (I)

[0012] A cerium complex containing the first compound and / or the second compound can emit blue light upon irradiation with ultraviolet light, etc. The first compound, which is a relatively soft base according to the HSAB rule, interacts weakly with cerium(III) ions, which are hard acids, compared to common organic ligands such as triphenylphosphine. This weak interaction is thought to contribute to the strong blue emission of the cerium complex. The second compound, due to its hardness as a base, can interact somewhat strongly with cerium(III) ions, but the introduction of a substituent that suppresses the interaction causes it to interact relatively weakly with cerium(III) ions. Therefore, like the first compound, the second compound is thought to contribute to the strong blue emission of the cerium complex. The emission wavelength can also be shifted to any wavelength range by changing the type of coordinating compound.

[0013] The hardness and softness as a base in the HSAB rule can be compared, for example, based on chemical hardness. That is, the first compound may be a compound exhibiting a chemical hardness lower than that of triphenylphosphine oxide. The second compound may be a compound exhibiting a chemical hardness equal to or greater than that of triphenylphosphine oxide and having a substituent that suppresses the interaction between the second compound and cerium (III) ions. The chemical hardness η can be a value calculated by the following formula: η=(IA) / 2 where I is the ionization energy and A is the electron affinity. A low chemical hardness corresponds to a soft acid or base.

[0014] The first compound may be, for example, a compound having one or more functional groups selected from a phosphine group (-P<), a nitrile group (-CN), a mercapto group (-SH), a thio group (-S-), an arsine group (-As<), an isocyanide group (-NC), and a phosphite group (P(-O-)3). The phosphine group refers to a phosphorus atom substituted with one or more hydrocarbon groups, each of which may have a substituent. The thio group refers to a sulfur atom substituted with two hydrocarbon groups, each of which may have a substituent. The arsine group refers to an arsenic atom substituted with one or more hydrocarbon groups, each of which may have a substituent.

[0015] The second compound may be a compound having a coordinating functional group and a substituent other than a hydrogen atom. The substituent suppresses the interaction between the second compound (coordinating functional group) and the cerium (III) ion due to its bulkiness, the position of substitution, and other factors. The coordinating functional group possessed by the second compound may be, for example, a hydroxyl group, an amino group, a phosphine oxide group, a carboxylate anion (-COO - The substituent may be one or more groups selected from the group consisting of a nitrogen atom in a nitrogen-containing heteroaromatic compound, a nitrogen atom in a nitrogen-containing heteroaromatic compound, and a nitro group. The substituent may be directly bonded to the coordinating functional group, or may be bonded to a carbon atom bonded to the coordinating functional group via one or two covalent bonds. The substituent may be one or more groups selected from the group consisting of a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, and an alicyclic group.

[0016] Examples of the first compound include compounds represented by the following formulas (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I), and (1J). The coordinating compound constituting the cerium complex may be one or more first compounds selected from these compounds.

[0017] [ka]

[0018] In formula (1A), R 1 , R 2 and R 3 are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. 1 , R 2 and R 3 Two selected from the above may be bonded to form a cyclic group. In formula (1B), R 4 is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. In formula (1C), R 5 is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. In formula (1D), R 6 and R 7 are each independently an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 6 and R 7 may be bonded to form a cyclic group. In formula (1E), R 8 and R 9 are each independently an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 8 and R 9 may be bonded to form a cyclic group. In formula (1F), R 10 , R 11 and R 12 R are each independently an aliphatic hydrocarbon group which may have a substituent, an aromatic group which may have a substituent, or a hydrogen atom. 10 , R 11 and R 12 Two selected from the above may be bonded to form a cyclic group. In formula (1G), R 13 is an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. In formula (1H), R 14, R 15 and R 16 are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. 14 , R 15 and R 16 Two selected from the above may be bonded to form a cyclic group. In formula (1I), R 17 and R 18 are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom. 17 and R 18 may be bonded to form a cyclic group.

[0019] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 may contain a group in which one or more hydrogen atoms have been removed from the compound represented by formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I), or (1J). In other words, the first compound may contain a plurality of structures corresponding to the compound represented by formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I), or (1J).

[0020] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 or R 18 When is an aliphatic hydrocarbon group having a substituent, the substituent may be a halogeno group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 or R 18 When is an aryl group having a substituent, the substituent may be a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. The halogeno groups exemplified herein may be chloro or fluoro groups. As used herein, "halogenated" means substituted with one or more halogeno groups, such as chloro and fluoro groups.

[0021] R in formula (1A) 1 , R 2 and R 3 One or more of R may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 1 , R 2 and R 3 may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent.1 , R 2 or R 3 The aliphatic hydrocarbon group as R may be an alkyl group or an alkenyl group, and may be an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 1 to 8 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, an n-heptyl group, and an n-octyl group. 1 , R 2 or R 3 The aryl group as may be a phenyl group or a naphthyl group.

[0022] Specific examples of the compound represented by formula (1A) include compounds represented by the following formulas (101), (102), (103), (104), (105), (106), and (107). In formula (106), n represents an integer of 0 to 7. The aryl groups in formulas (101) to (105) may be substituted with one or more substituents.

[0023] [ka]

[0024] [ka]

[0025] R in formula (1B) 4 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group R includes the same groups as those exemplified as the aliphatic hydrocarbon group or aryl group. 4 may be an alkyl group having 1 to 8 or 2 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, or an aryl group which may have a substituent. The compound represented by formula (1B) may be a compound represented by the following formula (1B-2). The compound represented by formula (1B-2) is a compound represented by formula (1B) where R4 is an example of a compound containing a group in which one or more hydrogen atoms have been removed from the compound represented by formula (1B). 41 is an aliphatic hydrocarbon group which may have a substituent, or an arylene group which may have a substituent. 41 may be an alkylene group having 2 to 8 carbon atoms, an alkenylene group having 2 to 8 carbon atoms which may have a substituent, or an arylene group which may have a substituent.

[0026] [ka]

[0027] Specific examples of the compound represented by formula (1B) include compounds represented by the following formulas (110), (111), (112), and (113). In formula (110), n represents an integer of 0 to 7 or 1 to 7. In formula (111), n ​​represents an integer of 1 to 8. The phenyl group in formula (112) may be substituted with one or more substituents.

[0028] [ka]

[0029] R in formula (1C) 5 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The phenyl groups in formula (121) and (122) may be substituted with one or more substituents. Specific examples of the compound represented by formula (1C) include compounds represented by formula (120), (121), or (122). In formula (120), n represents an integer of 0 to 7. The phenyl groups in formulas (121) and (122) may be substituted with one or more substituents.

[0030] [ka]

[0031] R in formula (1D)6 or R 7 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group in formula (1D) includes the same groups as those exemplified as the aliphatic hydrocarbon group or aryl group. Specific examples of the compound represented by formula (1D) include compounds represented by formula (123) or (124) below. In formula (123), n represents an integer of 0 to 7. The phenyl group in formula (124) may be substituted with one or more substituents.

[0032] [ka]

[0033] R in formula (1E) 8 or R 9 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The phenyl group in formula (125) may be substituted with one or more substituents.

[0034] [ka]

[0035] R in formula (1F) 10 , R 11 and R 12 One or more of R may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 10 , R 11 and R 12 may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 10 , R 11 or R 12Examples of the aliphatic hydrocarbon group and aryl group are R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group in formula (1F) includes the same groups as those exemplified as the aliphatic hydrocarbon group or aryl group. Specific examples of the compound represented by formula (1F) include compounds represented by the following formulas (130), (131) or (132). In formula (130), n represents an integer of 0 to 7. The phenyl group in formula (132) may be substituted with one or more substituents.

[0036] [ka]

[0037] R in formula (1G) 13 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group in formula (1G) includes the same groups as those exemplified as the aliphatic hydrocarbon group or aryl group. Specific examples of the compound represented by formula (1G) include compounds represented by the following formulas (140), (141), (142), or (143). In formula (140), n represents an integer of 0 to 7. The phenyl group in formula (143) may be substituted with one or more substituents.

[0038] [ka]

[0039] R in formula (1H) 14 , R 15 and R 16 One or more of R may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 14 , R 15 and R 16 may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 14 , R 15 or R 16Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group in formula (1H) includes the same groups as those exemplified as the aliphatic hydrocarbon group or aryl group. Specific examples of the compound represented by formula (1H) include compounds represented by the following formulas (150), (151), or (152). In formula (150), n represents an integer of 0 to 7. The phenyl group in formula (152) may be substituted with one or more substituents.

[0040] [ka]

[0041] R in formula (1I) 17 and R 18 One or more of R may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 17 and R 18 may be an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent. 17 and R 18 may be bonded to form a cyclic group (e.g., a cyclohexane ring). 17 or R 18 Examples of the aliphatic hydrocarbon group and aryl group as R 1 , R 2 and R 3 The aliphatic hydrocarbon group or aryl group may be substituted with a substituent. Specific examples of the compound represented by formula (1I) include compounds represented by the following formulas (161), (162), (163), (164), (165), (166), (167), (168), (169), (170), (171), or (172). One or more hydrogen atoms in these compounds may be substituted with a substituent.

[0042] [ka]

[0043] Examples of the second compound as a coordinating compound include compounds represented by the following formulas (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K), and (2L). The coordinating compound constituting the cerium complex may be one or more second compounds selected from these compounds.

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] [ka]

[0048] R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 and R 40may contain a group in which one or more hydrogen atoms have been removed from a compound represented by formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K), or (2L). In other words, the second compound may contain a plurality of structures corresponding to the compound represented by formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K), or (2L).

[0049] In formula (2B), Z 1 is —OH, —NH2, or —NO2. 2 is -OH, -NH2, -NO2, or -COO - is.

[0050] In formulas (2A), (2B), (2C), (2D) and (2E), R 21 and R 25 are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or -COOH. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group. Multiple R 21 and R 25 When R is present, they may be the same or different. 21 and R 25 may each independently be a halogeno group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group), or —COOH.

[0051] In formulas (2A), (2B), (2C), (2D) and (2E), R 22 , R 23 and R 24are each independently a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or -COOH. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group. Multiple R 22 , R 23 and R 24 When present, they may be the same or different.

[0052] In formulas (2A), (2B), (2C), (2D) and (2E), R 21 , R 22 , R 23 , R 24 and R 25 Two selected from the following may be bonded to form a cyclic group. For example, R 21 and R 22 Bond with R 22 and R 23 Bond with R 23 and R 24 Bond with or R 24 and R 25 The bond may form a cyclic group.

[0053] In formula (2A), (2B), (2C), (2D) or (2E), R 21 , R 22 , R 23 , R 24 and R 25 In formula (2A), (2B), (2C), (2D), or (2E), R 21 and R 25 is an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or -COOH; and R 22 , R 23 and R 24 may be a hydrogen atom.

[0054] Specific examples of the compound represented by formula (2A) include compounds represented by the following formulas (201), (202), (203) and (204). X in formulas (201) to (204) is a halogeno group (for example, a chloro group or a fluoro group).

[0055] [ka]

[0056] Specific examples of the compound represented by formula (2E) include compounds represented by the following formulae (210), (211), (212), (213), (214), (215), (216) and (217). X in formulae (210) to (213) is a halogeno group (e.g., a chloro group or a fluoro group). R in formulae (214) to (217) x is R in formula (2E). 21 and R 25 is defined similarly.

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] In formula (2F), R 26 and R 30 are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. 27 , R 28 and R 29 are each independently a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group. R 26 , R 27 , R 28 , R 29 and R 30 Two selected from the following may be bonded to form a cyclic group. For example, R 26 and R 27 Bond with R 27 and R 28 Bond with R 28 and R 29 Bond with or R 29 and R 30 The bond may form a cyclic group.

[0064] In formula (2G), R 31 and R 34 are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. 32 and R 33are each independently a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group. R 31 , R 32 , R 33 , and R 34 Two selected from the following may be bonded to form a cyclic group. For example, R 31 and R 32 Bond with R 32 and R 33 Bond with or R 33 and R 34 The bond may form a cyclic group.

[0065] In formula (2H), R 35 , R 36 and R 37 are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group.

[0066] In formulas (2I), (2J), (2K) and (2L), R 40 is an alicyclic group which may have a substituent. 40 When present, they may be the same or different. 40When R is an alicyclic group having a substituent, the substituent is a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group. The alkyl group and alkoxy group contained in these groups may have 1 to 8 carbon atoms. The aryl group contained in these groups may be a phenyl group. 40 Examples of alicyclic groups as R include a cyclohexyl group and an adamantyl group. 40 may be bonded to form a cyclic group.

[0067] Specific examples of the compound represented by formula (2I) include a compound represented by the following formula (220). Specific examples of the compound represented by formula (2L) include a compound represented by the following formula (221) or (222). The alicyclic groups in formulas (220) to (222) may have one or more substituents.

[0068] [ka]

[0069] [ka]

[0070] The cerium complexes of the present disclosure can be formed, for example, by a method comprising dissolving a coordinating compound in a solution containing cerium(III) thiocyanate and a solvent. In the solution, a cerium complex is formed, which includes the coordinating compound that interacts with cerium(III) ions. Removal of the solvent from the solution provides a luminescent solid containing the cerium complex.

[0071] The cerium complex can be combined with other materials as needed to form various luminescent bodies. For example, a luminescent resin molded body having any shape can be obtained from a resin molding material containing an organic polymer and a cerium complex. In the resin molded body, the cerium complex is usually dispersed in the organic polymer.

[0072] The organic polymer to be combined with the cerium complex may be a transparent resin, and examples of the organic polymer include polystyrene, polycarbonate, polyethylene terephthalate, styrene-methyl methacrylate copolymer (SMMA), polyvinyl toluene, and ABS resin.

[0073] The content of the cerium complex in the resin molded product may be, for example, 0.1% by mass or more and 50% by mass or less based on the total amount of the organic polymer and the cerium complex.

[0074] The resin molded article containing an organic polymer and a cerium complex may be a resin film. The resin film, which is a resin molded article, can be produced, for example, by a method including removing the solvent from a film of a resin molding material containing an organic polymer, a cerium complex, and a solvent.

[0075] The cerium complex according to the present disclosure emits strong light upon absorption of radiation such as α-rays, and therefore can also be used as a scintillator material for detecting radiation (particularly α-rays). The scintillator material containing the cerium complex can be used in solid scintillators or liquid scintillators.

[0076] A resin molded body containing an organic polymer and a cerium complex can be used as a solid scintillator material for constituting a solid scintillator. In the case of a solid scintillator for α-ray measurement, taking into consideration elastic scattering and the photoelectric effect, which are the main interactions with background γ-rays, as well as the Compton effect, it is important that the effective atomic number of the scintillator material is small and that the solid scintillator has an appropriately designed thickness in the direction of radiation incidence. Considering the interaction with radiation such as γ-rays, it is desirable that the resin molded body constituting the solid scintillator for α-ray measurement is a resin film having a thin thickness in the direction of radiation incidence, and that the range of α-rays is equal to or less than the thickness of the resin film. The ratio of the α-ray ranges of two materials can be calculated using the following formula:

[0077]

number

[0078] In the above formula, R1 and R2 represent the range of α-rays, ρ0 and ρ1 represent density, and A0 and A1 represent atomic weight. For example, the range of α-rays in the resin molded product according to the present disclosure can be calculated from the relationship between the atomic weight of aluminum and the known range in aluminum. From the above formula, it can be seen that the range of α-rays in the resin molded product according to the present disclosure can be, for example, about 100 μm or less. Therefore, the thickness of the resin film constituting the solid scintillator for α measurement may be, for example, 100 μm or less. The thickness of the resin film constituting the solid scintillator may be 50 μm or more from the viewpoint of ease of production.

[0079] The resin molded article containing the organic polymer and cerium complex according to the present disclosure has a density of 4.08 g / cm, which is lower than that of ZnS(Ag), which is commonly used as a solid scintillator for measuring alpha rays. 2 For example, a resin molded product containing mainly polystyrene and a cerium complex has a density of 1.04 g / cm 3A resin molded article with a low density has a low probability of interaction with gamma rays, and is therefore suitable for alpha ray measurement.

[0080] When a solid scintillator is used in radiation measurement, the luminescence generated in the solid scintillator is generally amplified by a photomultiplier tube and converted into an electrical signal. Therefore, it is desirable to select a photomultiplier tube that has high sensitivity in the wavelength region of the luminescence of the solid scintillator. A scintillator material containing an organic polymer and a cerium complex can emit light in various different wavelength regions depending on the type of coordination compound, etc. Therefore, the wavelength region of the luminescence of the scintillator material constituting the solid scintillator can be easily changed to match the wavelength region to which the photomultiplier tube has high sensitivity. As a result, the degree of freedom in designing a radiation measuring instrument is increased.

[0081] The cesium complexes according to the present disclosure tend to exhibit a shorter luminescence lifetime than general scintillator materials. When measuring radiation using a solid scintillator in a high-dose environment, the influence of dead time must be taken into consideration, and a short luminescence lifetime can reduce the influence of dead time. Therefore, high-precision radiation measurement is possible in a high-dose environment. In addition, since the luminescence lifetime of a scintillator material containing a cesium complex can be arbitrarily changed based on the type of coordination compound, etc., solid scintillators can be easily designed to suit the radiation environment.

[0082] The cerium complex according to the present disclosure can also be used as a liquid scintillator material in a liquid scintillator. By applying the liquid scintillator, radiation can be measured by liquid scintillation counting. Liquid scintillation counting is a technique in which a substance to be measured (e.g., a radioactive substance that emits α-rays) is directly dissolved in a liquid scintillator, and the luminescence generated by the interaction between charged particles from the substance to be measured and the liquid scintillator is converted into an electrical signal, which is amplified and measured. Liquid scintillation counting, due to its measurement principle, can reduce problems such as self-absorption, making it possible to measure low-energy β-rays such as H-3 or C-14, and short-range α-rays.

[0083] In radiation measurement using a liquid scintillator, the effect of quenching must be taken into consideration. Quenching is a phenomenon in which the intensity of luminescence decreases due to the interaction between charged particles from the substance to be measured and the liquid scintillator, and can be broadly classified into chemical quenching and color quenching. In color quenching, light is weakened due to the optical properties of the color of the solution. The cerium complex according to the present disclosure is easily capable of forming a solution with high transparency, and is therefore advantageous in terms of reducing the effect of color quenching in the liquid scintillator.

[0084] The liquid scintillator material constituting the liquid scintillator may contain, for example, a cerium complex and a solvent in which the cerium complex is dissolved. The solvent may be, for example, dichloromethane. The liquid scintillator material can be obtained by dissolving a solid of a cerium complex containing a coordinating compound in a solvent. The solid of a cerium complex containing a coordinating compound can be obtained, for example, by removing the solvent from a solution of a cerium complex containing a coordinating compound, such as acetonitrile.

[0085] [Example] The present invention is not limited to the following examples. 1. Cerium complex The following coordinating compounds were prepared: Pentafluoropyridine (pyF, second compound) Triphenylphosphine (TPP, first compound) Triphenylphosphine oxide (TPPO) [ka]

[0086] 50 mg of cerium(III) trifluoromethanesulfonate, 75 mg (4.5 equivalents) of tetrabutylammonium thiocyanate, and 2 equivalents of each coordinating compound were dissolved in 7 mL of solvent. The precipitate that formed in the solution was removed by filtration using a syringe filter to obtain a complex solution containing a cerium(III) complex having a thiocyanate ion and a coordinating compound. Complex solutions were prepared using chloroform, acetonitrile, or dichloromethane as the solvent, combining the materials shown in Table 1, #1-0 to #3-3. In #1-0, #2-0, and #3-0, no coordinating compound was used.

[0087] [Table 1]

[0088] The solvent was distilled off from each of the complex solutions #1-0 to #3-3 to obtain solids containing cerium complexes. Mass spectrometry using the solid obtained in #2-2 as a sample did not confirm the parent signals of the thiocyanate ion and the cerium(III) complex with the coordination compound, but did confirm the signal of its fragment component, [Ce(SCN)4]. The results of mass spectrometry are shown below. ESI-MS (m / z): [Ce(SCN)4] - calculated for C4CeN4S4 -1 , 371.80;found, 371.81.

[0089] 2. Absorption characteristics The UV-visible absorption spectra of the cerium complexes were measured using the complex solutions #1-0 to #3-3. Figures 1 and 2 show the UV-visible absorption spectra of the cerium complexes in a complex solution containing chloroform. Figures 3 and 4 show the UV-visible absorption spectra of the cerium complexes in a complex solution containing acetonitrile. Figures 5 and 6 show the UV-visible absorption spectra of the cerium complexes in a complex solution containing dichloromethane. Figures 2, 4, and 6 show enlarged views of the area around 500 nm. The absorption band at wavelengths of 300 to 400 nm, which is attributed to the fd transition of the cerium(III) ion, shifted with the introduction of the coordination compound, suggesting that the coordination compound interacts with the cerium(III) ion. Figures 2, 4, and 6 show a tendency for the absorption intensity around 500 nm to decrease with the introduction of the coordination compound tpp. The absorption band around 500 nm is thought to be derived from cerium(IV) ions produced by the oxidation of cerium(III) ions, suggesting that the introduction of a coordination compound can form a cerium(III) complex that is resistant to oxidation and highly stable.

[0090] 3. Luminous properties Each of the complex solutions #1-0 to #3-3 was irradiated with ultraviolet light at a wavelength of 365 nm, and the luminescence state of each complex solution was observed. The complex solution without a coordinating compound (nan) and the complex solutions with pyF or tpp as a coordinating compound emitted strong blue light when irradiated with ultraviolet light.

[0091] Figures 7, 8, and 9 show the emission spectra (excitation wavelength: 300 nm) of each complex solution. When tpp was introduced as a coordinating compound, the emission wavelength was significantly shifted to the long wavelength side compared to when no coordinating compound was introduced (nan).

[0092] The luminescence decay curves were measured for the complex solution containing acetonitrile and the complex solution containing chloroform. The luminescence lifetimes τ1 and τ2 calculated from the luminescence decay curves, as well as the average luminescence lifetime τ aveThe luminescence lifetimes are shown in Table 1. τ1 is the luminescence lifetime due to fast energy transfer from the excited singlet state of the ligand via the excited state of the rare earth ion. τ2 is the luminescence lifetime due to slow energy transfer from the excited triplet state of the ligand via the excited state of the rare earth ion. Alternatively, τ1 and τ2 are due to the formation of multiple complex structures. Following the standard method, the excitation light spectrum and emission spectrum of the reference and cerium complex were measured using an integrating sphere, and the luminescence quantum yield was calculated using the difference in the integrated excitation light intensity between the reference and cerium complex and the integrated intensity of the luminescence from the cerium complex. The cerium complex incorporating tpp as a coordinating compound exhibited a relatively high luminescence quantum efficiency of 49%.

[0093] 4.Scintillator characteristics A complex solution containing acetonitrile as the solvent and no additional coordinating compound was prepared using the same procedure as in "1. Complex Solution." A solid cerium complex was obtained by removing the solvent from the complex solution. The resulting solid is believed to contain a cerium complex having a thiocyanate ion and acetonitrile as the coordinating compound. The solid cerium complex was dissolved in dichloromethane. Polystyrene was further dissolved in the resulting solution to obtain a coating liquid (resin molding material) containing the cerium complex and polystyrene. A film of the coating liquid was applied to a substrate, and a resin film containing the cerium complex and polystyrene was formed by removing the dichloromethane from the coating film.

[0094] The resin film was irradiated with alpha particles (americium-241), and the change in the integrated luminescence intensity at wavelengths from 300 nm to 650 nm was measured. Figure 10 shows the change in luminescence intensity due to alpha particle irradiation. Clear luminescence was observed triggered by the irradiation of alpha particles. These results confirmed that the resin film can function as a scintillator material.

Claims

1. cerium (III) ions, thiocyanate ion, a coordinating compound that interacts with the cerium (III) ion; A cerium complex comprising: the coordinating compound is a first compound, a second compound, or a combination of the first compound and the second compound; the first compound is a compound that is a softer base than triphenylphosphine oxide according to the HSAB rule; the second compound is a compound that is a harder base than triphenylphosphine oxide according to the HSAB rule and has a substituent that suppresses the interaction between the second compound and the cerium (III) ion; Cerium complexes.

2. cerium (III) ions, thiocyanate ion, a coordinating compound that interacts with the cerium (III) ion; A cerium complex comprising: the coordinating compound is a first compound, a second compound, or a combination of the first compound and the second compound; The first compound is represented by the following formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I), or (1J): 【Chemistry 1】 is a compound represented by R １ , R ２ and R ３ are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom, and R １ , R ２ and R ３ two selected from the group consisting of may be bonded to form a cyclic group, R ４ is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, R ５ is an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, R ６ and R ７ are each independently an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, and R ６ and R ７ may be bonded to form a cyclic group, R ８ and R ９ are each independently an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, and R ８ and R ９ may be bonded to form a cyclic group, R １０ , R １１ and R １２ are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom, and R １０ , R １１ and R １２ two selected from the group consisting of may be bonded to form a cyclic group, R １３ is an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom, R １４ , R １５ and R １６ are each independently an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom, and R １４ , R １５ and R １６ two selected from the group consisting of may be bonded to form a cyclic group, R １７ and R １８ are each independently an aliphatic hydrocarbon group which may have a substituent, or an aryl group which may have a substituent, and R １７ and R １８ may be bonded to form a cyclic group, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ and R １８ may contain a group obtained by removing one or more hydrogen atoms from a compound represented by formula (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H), (1I) or (1J), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ or R １８ is a substituted aliphatic hydrocarbon group, the substituent is a halogeno group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ or R １８ is a substituted aryl group, the substituent is a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group, The second compound is represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K), or (2L): 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 is a compound represented by Z １ But -OH, -NH ２ , or -NO ２ and Z ２ But -OH, -NH ２ , -NO ２ , or -COO － and R ２１ and R ２５ are each independently a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or —COOH; and ２１ and R ２５ may be the same or different, R ２２ , R ２３ and R ２４ are each independently a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, an aryloxy group, or —COOH; and ２２ , R ２３ and R ２４ may be the same or different, R ２１ , R ２２ , R ２３ , R ２４ and R ２５ two selected from the group consisting of may be bonded to form a cyclic group, R ２６ , R ３０ , R ３１ , R ３４ , R ３５ , R ３６ and R ３７ each independently represents a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group; R ２７ , R ２８ , R ２９ , R ３２ and R ３３ each independently represents a hydrogen atom, a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, or an aryloxy group; R ２６ , R ２７ , R ２８ , R ２９ and R ３０ two selected from the group may be bonded to form a cyclic group, and R ３１ , R ３２ , R ３３ , and R ３４ two selected from the group consisting of may be bonded to form a cyclic group, R ４０ is an alicyclic group which may have a substituent, and there are multiple R ４０ may be the same or different, R ４０ is a substituted alicyclic group, the substituent is a halogeno group, an alkyl group, a halogenated alkyl group, an arylalkyl group, an alkoxyalkyl group, an alkoxy group, a halogenated alkoxy group, an arylalkoxy group, an aryl group, a halogenated aryl group, an alkylaryl group, an alkoxyaryl group, or an aryloxy group, and two R ４０ may be bonded to form a cyclic group, R ２１ , R ２２ , R ２３ , R ２４ , R ２５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ , R ３４ , R ３５ , R ３６ , R ３７ and R ４０ may contain a group obtained by removing one or more hydrogen atoms from a compound represented by formula (2A), (2B), (2C), (2D), (2E), (2F), (2G), (2H), (2I), (2J), (2K) or (2L), Cerium complexes.

3. 3. The cerium complex of claim 2, wherein said coordinating compound is said first compound.

4. 4. The cerium complex according to claim 3, wherein the first compound is a compound represented by formula (1A):

5. the first compound is Represented by formula (1B), R ４ is an alkyl group having 2 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, or an aryl group which may have a substituent, or The following formula (1B-2): 【Transformation 6】 is represented by R ４１ The cerium complex according to claim 3 , wherein is an aliphatic hydrocarbon group which may have a substituent, or an arylene group which may have a substituent.

6. 3. The cerium complex of claim 2, wherein said coordinating compound is said second compound.

7. 7. The cerium complex according to claim 6, wherein the second compound is a compound represented by formula (2A):

8. A luminescent solid comprising a cerium complex according to any one of claims 1 to 7.

9. an organic polymer; The cerium complex according to any one of claims 1 to 7, which is dispersed in the organic polymer; A resin molded article comprising:

10. A scintillator material comprising the cerium complex according to any one of claims 1 to 7.

11. 11. The scintillator material according to claim 10, wherein the scintillator material is a resin molded product further containing an organic polymer, and the cerium complex is dispersed in the organic polymer.

12. The scintillator material of claim 11 having a thickness of 50 μm or more and 100 μm or less.

13. The scintillator material according to claim 10, which is a scintillator material for measuring alpha rays.

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