Metal-organic coordination compound and method for producing the same

A metal-organic coordination compound, wherein the coordination compound comprises at least one divalent lanthanide coordinated by an electrically neutral cyclic organic ligand according to formula 1:

• wherein
• i is larger than 3;
• and
• n is equal to 1, 2, or 3;
• and
• L for each occurrence is independently selected from
• divalent cyclic organic groups that can be substituted with substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof and that are formed by removing two hydrogen atoms from an organic cyclic molecule that can be substituted with substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
• arylenes, preferably 5- or 6-membered ring aromatic or heteroaromatic group, or
• biradical fragments of
• and
• X is independently selected for each occurrence from the group of:
• wherein R1 and R2 are hydrogen or any covalently bound substituents being identical or different in each occurrence and selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• and
• wherein R1 and/or R2 are at least in 3 occurrences not hydrogen, and
• wherein two groups R2 can be covalently linked with each other, thereby forming a further cyclic element,
• wherein the cyclic organic ligand can be covalently linked with a polymer chain or a polymer backbone,
• it also being possible that two cyclic organic ligands of formula 1 are covalently linked with each other by one or two divalent linking groups which divalent linking groups are formed of one R1 of each of the two cyclic organic ligands of formula 1 that are covalently linked with each other,
• wherein one R1 and one R2 are covalently linked with each other thereby forming a polycyclic ligand, and/or wherein at least two R2 are covalently linked with each other, thereby forming a bridge to form a polycyclic ligand, wherein the coordination compound comprises at least one negatively charged anion, which is not covalently bound to the organic ligand, and has a molecular weight of at least 128 g/mol or includes more than 3 atoms and wherein the divalent lanthanide is Europium or Ytterbium wherein preferably the negatively charged anion has a molecular weight in the range of from 128 to 1000 g/mol.

A metal-organic coordination compound, wherein the coordination compound comprises at least one divalent lanthanide coordinated by a cyclic organic ligand according to formula 3:

• wherein
• Y for each occurrence independently is B or N or P
• X is independently selected for each occurrence from the group of:
• L for each occurrence independently is a divalent cyclic organic group that can be substituted with substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof and that is formed by removing two hydrogen atoms from an organic cyclic molecule that can be substituted with sub stituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or is a divalent group —CR1R1— or —SiR1R1—
• wherein R1 and R2 are hydrogen or any covalently bound substituents being identical or different in each occurrence and selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
• n1, n2, i independently are equal to 1, 2, 3, or 4,
• wherein the coordination compound comprises at least one negatively charged anion, which is not covalently bound to the organic ligand, and has a molecular weight of at least 128 g/mol or includes more than 3 atoms the divalent lanthanide is Europium or Ytterbium, and the cyclic organic ligand can be covalently linked with a polymer chain or a polymer backbone,
• wherein preferably the compound of formula 3 has one or more of the following features:
• Y is B or N, wherein preferably R2 is alkyl, alkoxy, carboxy, aryl, aryloxy or F,
• all three structural elements
• in the compound of formula 3 are identical,
• divalent cyclic organic groups L for each occurrence independently are divalent cyclic organic groups that can be substituted and that are formed by removing two hydrogen atoms from neighboring carbon and/or nitrogen atoms in the ring of an organic cyclic molecule that can be substituted, n1 and n2 being 1,
• cyclic organic groups are carbocyclic or heterocyclic groups, the heteroatoms being selected from P, N, Si, O, S
• if in
• and/or
• L is —CR1R1—, then n1 and/or n2 is 2,
• contains two groups X being
• wherein both R2 together form a group
• which is identical with group
• linking the two groups X,
• i is 2,
• the cyclic organic ligand according to formula 3 is electrically neutral.

A metal-organic coordination compound, wherein the coordination compound comprises at least one divalent lanthanide coordinated by a cyclic organic ligand according to formula 3:

• wherein
• Y for each occurrence independently is B or B—R2 or N or P
• X is independently selected for each occurrence from the group of:
• L for each occurrence independently is a divalent cyclic organic group that can be substituted with substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof and that is formed by removing two hydrogen atoms from an organic cyclic molecule that can be substituted with substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof or is a divalent group —CR1R1— or
• —SiR1R1—
• wherein R1 and R2 are hydrogen or any covalently bound substituents being identical or different in each occurrence and selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
• n1, n2, i independently are equal to 1, 2, 3, or 4,
• the cyclic organic ligand can be covalently linked with a polymer chain or a polymer backbone and wherein the divalent lanthanide is Europium or Ytterbium,
• with the exception of
• wherein the cyclic organic ligand according to formula 3 can be electrically neutral.