Rare earth complex
AssigneesTosoh Corporation, Sagami Chemical Research Institute
InventorsKeisuke ARAKI, Haruki MAEBAYASHI, Airi MASAKI, Naoyuki KOISO, Ryo NAKAGAME, Masanori YAMAMOTO, Ippei SASAKI, Kohei IWANAGA
Life of this patent
Estimating the term…
Abstract
A rare earth complex is represented by general formula (1). M3+·(HC)n·(L1)m1·(L2)m2·(XL)3-n (1) [In the formula, HC represents a quinolinonato ligand or coumarinato ligand, L1 represents, for example, a nitrogen-containing ligand, L2 represents, for example, water, XL represents, for example, a halide ion, M3+ represents a trivalent rare earth metal ion, n represents 1, 2 or 3, m1 represents 0, 1 or 2, and m2 represents 0 to 3.]
Claims21
1-32. (canceled)
A rare earth complex represented by general formula (1):
- [Formula 1]
- M3+·(HC)n·(L1)m1·(L2)m2·(XL)3-n (1)
- {HC is a quinolinonato ligand represented by general formula (1qu) or coumarinato ligand represented by general formula (1cu);
- wherein in the formula 2, RA represents a C1 to C6 haloalkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group. The aryl group and the heteroaryl group are optionally substituted with one or more substituents selected from the group consisting of C1 to C6 fluoroalkyl groups;
- C1 to C6 alkyloxy groups;
- C1 to C6 fluoroalkyloxy groups;
- C5 to C14 aryloxy groups;
- C1 to C6 monoalkylamino groups;
- C6 to C12 monoarylamino groups;
- C4 to C12 monoheteroarylamino groups;
- C2 to C12 dialkylamino groups;
- C10 to C24 diarylamino groups optionally substituted with one or more cyano groups, halogen atoms or C1 to C6 fluoroalkyl groups;
- C8 to C24 diheteroarylamino groups optionally substituted with one or more fluorine atoms or C1 to C6 fluoroalkyl groups;
- C3 to C20 heteroaryl groups;
- C2 to C13 acyl groups;
- methylenedioxy groups;
- ethylenedioxy groups;
- halogen atoms;
- hydroxyl groups;
- nitro groups and cyano groups;
- RB1, RB2, RB3, RB4 and RB5 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano groups and nitro groups;
- (wherein in the formula 3, RBA1 and RBA2 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA1 and RBA2 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA1 and RBA are bound);
- (wherein in the formula 4, RBO1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 5, RBS1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- of RB1, RB2, RB3 and RB4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- RB5 and RB1 optionally form a five-membered, six-membered or seven-membered ring together with the quinolinone ring system to which the RB5 and RB1 are bound;
- wherein in the formula 6, RA is synonymous with RA in general formula (1qu);
- RC1, RC2, RC3 and RC4 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group optionally substituted with one or more C1 to C6 alkyloxy groups, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano group and nitro groups;
- (wherein in the formula 7, RBA1 and RBA2 are synonymous with the meanings described above);
- (wherein in the formula 8, RBO1 is synonymous with the meaning described above);
- (wherein in the formula 9, RBS1 is synonymous with the meaning described above);
- of RC1, RC2, RC3 and RC4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- n represents 1, 2 or 3, and when n is 2 or 3, the plurality of quinolinonato ligands or coumarinato ligands may be the same or different from each other;
- m1 represents 0, 1 or 2, m2 represents 0 to 3, and 0≤m1+m2≤3;
- L1 represents a nitrogen-containing ligand having two or more nitrogen atoms possessing a lone pair or phosphorus ligand represented by general formula (3a) below or general formula (3b) below. When m1 is 2, the Lis may be the same or different from each other;
- wherein in the formulae 10 and 11, the XAs each independently represent a C1 to C10 alkyl group, aryl group represented by general formula (3c) below, substituted or unsubstituted amino group indicated by general formula (BA2) below or substituted or unsubstituted oxy group indicated by general formula (BO2) below;
- (wherein in the formula 12, the X1s each independently represent a hydrogen atom, halogen atom, C1 to C6 alkyl group, C1 to C6 alkyloxy group, C6 to C22 aryl group, C3 to C20 heteroaryl group, C5 to C14 aryloxy group, C1 to C6 haloalkyl group or C1 to C6 haloalkyloxy group, with the aryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 haloalkyl groups, C1 to C6 haloalkyloxy groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 13, RBA3 and RBA4 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA3 and RBA4 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA3 and RBA4 are bound);
- (wherein in the formula 14, RBO2 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- XH represents a C1 to C10 alkylene group, C2 to C10 alkenylene group, C2 to C10 alkynylene group, C5 to C24 arylene group or C4 to C23 heteroarylene group;
- L2 represents a neutral ligand selected from the group consisting of water, deuterium oxide, sulfoxide compounds, sulfone compounds, amide compounds, nitrile compounds, ester compounds, carbonyl compounds, ether compounds and alcohols;
- wherein when m2 is 2 or 3, the L2s may be the same or different from each other;
- XL represents a halide ion, nitrate ion, carboxylate ion, sulfonate ion or C5 to C12 β-diketonato ion;
- M3+ represents a trivalent rare earth metal ion}.
A method of manufacturing a rare earth complex (1), the method comprising allowing an enol represented by general formula (4b) or general formula (4c) below, a phosphorus ligand indicated by general formula (3a) below;
- a phosphorus ligand indicated by general formula (3b) below;
- or a nitrogen-containing compound having two or more nitrogen atoms possessing a lone pair, which is represented by L1, or/and a neutral ligand, which is represented by L2, selected from the group consisting of;
- water;
- deuterium oxide;
- a sulfoxide compound;
- sulfone compound;
- amide compound;
- nitrile compound;
- ester compound;
- carbonyl compound;
- ether compound and alcohol and a rare earth compound to react together;
- {HC is a quinolinonato ligand represented by general formula (1qu) or coumarinato ligand represented by general formula (1cu);
- wherein in the formula 24, RA represents a C1 to C6 haloalkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the aryl group and the heteroaryl group being optionally substituted with one or more substituents selected from the group consisting of C1 to C6 fluoroalkyl groups;
- C1 to C6 alkyloxy groups;
- C1 to C6 fluoroalkyloxy groups;
- C5 to C14 aryloxy groups;
- C1 to C6 monoalkylamino groups;
- C6 to C12 monoarylamino groups;
- C4 to C12 monoheteroarylamino groups;
- C2 to C12 dialkylamino groups;
- C10 to C24 diarylamino groups optionally substituted with one or more cyano groups, halogen atoms or C1 to C6 fluoroalkyl groups;
- C8 to C24 diheteroarylamino groups optionally substituted with one or more fluorine atoms or C1 to C6 fluoroalkyl groups;
- C3 to C20 heteroaryl groups;
- C2 to C13 acyl groups;
- methylenedioxy groups;
- ethylenedioxy groups;
- halogen atoms;
- hydroxyl groups;
- nitro groups and cyano groups;
- RB1, RB2, RB3, RB4 and RB5 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano groups and nitro groups;
- (wherein in the formula 25, RBA1 and RBA2 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA1 and RBA2 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA1 and RBA are bound);
- (wherein in the formula 26, RBO1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 27, RBS1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- of RB1, RB2, RB3 and RB4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- RB5 and RB1 optionally form a five-membered, six-membered or seven-membered ring together with the quinolinone ring system to which the RB5 and RB1 are bound;
- wherein in the formula 28, RA is synonymous with RA in general formula (1qu);
- RC1, RC2, RC3 and RC4 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group optionally substituted with one or more C1 to C6 alkyloxy groups, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano groups and nitro groups;
- (wherein in the formula 29, RBA1 and RBA2 are synonymous with the meanings described above);
- (wherein in the formula 30, RBO1 is synonymous with the meaning described above);
- (wherein in the formula 31, RBS1 is synonymous with the meaning described above);
- of RC1, RC2, RC3 and RC4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- n represents 1, 2 or 3. When n is 2 or 3, the plurality of quinolinonato ligands or coumarinato ligands may be the same or different from each other;
- m1 represents 0, 1 or 2, m2 represents 0, 1, 2 or 3, and 0≤m1+m2≤3;
- L1 represents a nitrogen-containing ligand having two or more nitrogen atoms possessing a lone pair or phosphorus ligand represented by general formula (3a) below or general formula (3b) below. When m1 is 2, the Lis may be the same or different from each other;
- wherein in the formulae 32 and 33, the XAs each independently represent a C1 to C10 alkyl group, aryl group represented by general formula (3c) below, substituted or unsubstituted amino group indicated by general formula (BA2) below or substituted or unsubstituted oxy group indicated by general formula (BO2) below;
- (wherein in the formula 34, the X1s each independently represent a hydrogen atom, halogen atom, C1 to C6 alkyl group, C1 to C6 alkyloxy group, C6 to C22 aryl group, C3 to C20 heteroaryl group, C5 to C14 aryloxy group, C1 to C6 haloalkyl group or C1 to C6 haloalkyloxy group, with the aryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 haloalkyl groups, C1 to C6 haloalkyloxy groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 35, RBA3 and RBA4 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA3 and RBA4 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA3 and RBA4 are bound);
- (wherein in the formula 36, RBO2 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- XH represents a C1 to C10 alkylene group, C2 to C10 alkenylene group, C2 to C10 alkynylene group, C5 to C24 arylene group or C4 to C23 heteroarylene group;
- L2 represents a neutral ligand selected from the group consisting of water, deuterium oxide, a sulfoxide compound, sulfone compound, amide compound, nitrile compound, ester compound, carbonyl compound, ether compound and alcohol;
- when m2 is 2 or 3, the L2s may be the same or different from each other;
- XL represents a halide ion, nitrate ion, carboxylate ion, sulfonate ion or C5 to C12 β-diketonato ion;
- M3+ represents a trivalent rare earth metal ion}.
A method of manufacturing a rare earth complex (1), the method comprising allowing a diketonato complex represented by general formula (1aq) below and a phosphorus ligand represented by general formula (3a) below;
- a phosphorus ligand represented by general formula (3b) below;
- or a nitrogen-containing ligand having two or more nitrogen atoms possessing a lone pair;
- which is represented by L1, or/and a neutral ligand, which is represented by L2, selected from the group consisting of;
- water;
- deuterium oxide;
- a sulfoxide compound;
- sulfone compound;
- amide compound;
- nitrile compound;
- ester compound;
- carbonyl compound;
- ether compound and alcohol to react together;
- {HC is a quinolinonato ligand represented by general formula (1qu) or coumarinato ligand represented by general formula (1cu);
- wherein in the formula 38, RA represents a C1 to C6 haloalkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group;
- with the aryl group and the heteroaryl group being optionally substituted with one or more substituents selected from the group consisting of C1 to C6 fluoroalkyl groups;
- C1 to C6 alkyloxy groups;
- C1 to C6 fluoroalkyloxy groups;
- C5 to C14 aryloxy groups;
- C1 to C6 monoalkylamino groups;
- C6 to C12 monoarylamino groups;
- C4 to C12 monoheteroarylamino groups;
- C2 to C12 dialkylamino groups;
- C10 to C24 diarylamino groups optionally substituted with one or more cyano groups, halogen atoms or C1 to C6 fluoroalkyl groups;
- C8 to C24 diheteroarylamino groups optionally substituted with one or more fluorine atoms or C1 to C6 fluoroalkyl groups;
- C3 to C20 heteroaryl groups;
- C2 to C13 acyl groups;
- methylenedioxy groups;
- ethylenedioxy groups;
- halogen atoms;
- hydroxyl groups;
- nitro groups and cyano groups;
- RB1, RB2, RB3, RB4 and RB5 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano groups and nitro groups;
- (wherein in the formula 39, RBA1 and RBA2 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA1 and RBA2 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA1 and RBA are bound);
- (wherein in the formula 40, RBO1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 41, RBS1 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- of RB1, RB2, RB3 and RB4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- RB5 and RB1 optionally form a five-membered, six-membered or seven-membered ring together with the quinolinone ring system to which the RB5 and RB1 are bound;
- wherein the formula 42, RA is synonymous with RA in general formula (1qu);
- RC1, RC2, RC3 and RC4 each independently represent a hydrogen atom, halogen atom, C1 to C10 alkyl group, C2 to C4 alkenyl group optionally substituted with one or more C1 to C6 alkyloxy groups, C1 to C6 haloalkyl group, C6 to C22 aryl group, C3 to C20 heteroaryl group, cyano group, nitro group, C7 to C14 aralkyl group optionally substituted with one or more halogen atoms, substituted or unsubstituted amino group indicated by general formula (BA1) below, substituted or unsubstituted oxy group indicated by general formula (BO1) below or substituted or unsubstituted thio group indicated by general formula (BS1) below, with the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, cyano groups and nitro groups;
- (wherein in the formula 43, RBA1 and RBA2 are synonymous with the meanings described above);
- (wherein in the formula 44, RBO1 is synonymous with the meaning described above);
- (wherein in the formula 45, RBS1 is synonymous with the meaning described above);
- of RC1, RC2, RC3 and RC4, two adjacent substituents optionally form a five-membered, six-membered or seven-membered ring together with the benzene ring to which the substituents are bound;
- n represents 1, 2 or 3. When n is 2 or 3, the plurality of quinolinonato ligands or coumarinato ligands may be the same or different from each other;
- m1 represents 0, 1 or 2, m2 represents 0 to 3, and 0≤m1+m2≤3;
- L1 represents a nitrogen-containing ligand having two or more nitrogen atoms possessing a lone pair or phosphorus ligand represented by general formula (3a) below or general formula (3b) below. When m1 is 2, the L1s may be the same or different from each other
- wherein in the formulae 46 and 47, the XAs each independently represent a C1 to C10 alkyl group, aryl group represented by general formula (3c) below, substituted or unsubstituted amino group indicated by general formula (BA2) below or substituted or unsubstituted oxy group indicated by general formula (BO2) below;
- (wherein in the formula 48, the X1s each independently represent a hydrogen atom, halogen atom, C1 to C6 alkyl group, C1 to C6 alkyloxy group, C6 to C22 aryl group, C3 to C20 heteroaryl group, C5 to C14 aryloxy group, C1 to C6 haloalkyl group or C1 to C6 haloalkyloxy group, with the aryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 haloalkyl groups, C1 to C6 haloalkyloxy groups, hydroxyl groups, cyano groups and nitro groups);
- (wherein in the formula 49, RBA3 and RBA4 each independently represent a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups. RBA3 and RBA4 optionally form a five-membered, six-membered or seven-membered ring including the nitrogen atom to which the RBA3 and RBA4 are bound);
- (wherein in the formula 50, RBO2 represents a hydrogen atom, C1 to C6 alkyl group, C6 to C22 aryl group or C3 to C20 heteroaryl group, with the alkyl group, the aryl group and the heteroaryl group optionally being substituted with one or more substituents selected from the group consisting of halogen atoms, C1 to C6 alkyloxy groups, C1 to C6 fluoroalkyl groups, C2 to C13 acyl groups, hydroxyl groups, cyano groups and nitro groups);
- XH represents a C1 to C10 alkylene group, C2 to C10 alkenylene group, C2 to C10 alkynylene group, C5 to C24 arylene group or C4 to C23 heteroarylene group;
- L2 represents a neutral ligand selected from the group consisting of water, deuterium oxide, a sulfoxide compound, sulfone compound, amide compound, nitrile compound, ester compound, carbonyl compound, ether compound and alcohol;
- when m2 is 2 or 3, the L2s may be the same or different from each other;
- XL represents a halide ion, nitrate ion, carboxylate ion, sulfonate ion or C5 to C12 β-diketonato ion;
- M3+ represents a trivalent rare earth metal ion;
- in the formulae, m represents 0, 1, 2 or 3;
- in the formulae, Q1 represents a neutral molecule, when m is not 0 and when m1 is 0, it is impossible that Q1 and L2 are the same, and m and m2 are equal at the same time.
Dependencies are inferred from the claim text.