MONONUCLEAR TRIPODAL HEXADENTATE IRIDIUM COMPLEXES FOR USE IN OLEDS
The present invention relates to iridium complexes that are suitable for use in organic electroluminescent devices, in particular as emitters.
1 .- 13 . (canceled)
14 . A compound of the formula (1)
Ir(L) Formula (1)
where the ligand L has a structure of the following formula (2):
where the ligand L coordinates to the iridium atom via the positions identified by * and where the hydrogen atoms not shown explicitly may also be replaced by D, and where the symbols and indices used are as follows:
R is the same or different at each instance and is H, D, F, a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group in each case may also be deuterated; optionally two adjacent R radicals together may form a ring system;
R 1 is the same or different at each instance and is H, D, a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group in each case may also be deuterated; optionally two adjacent R 1 radicals together may form a ring system;
R 2 is the same or different at each instance and is H, D, a linear alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl group in each case may also be deuterated, or a phenyl or biphenyl group, each of which may be substituted by one or more alkyl groups having 1 to 10 carbon atoms, where the phenyl or biphenyl group, or the alkyl groups, may each also be deuterated; optionally two adjacent R 2 radicals together may form a ring system;
m is 1, 2 or 3;
n is the same or different at each instance and is 0, 1, 2 or 3;
o is 0 or 1;
p is 0, 1 or 2;
q is 0, 1 or 2; and
r is 0, 1 or 2.
15 . A compound as claimed in claim 14 , wherein when m=1 the ligand L is a structure of the formula (3a), when m=2 the ligand L is a structure of the formula (3b) or (3c), and when m=3 the ligand L is a structure of the formula (3d) or (3e):
where the hydrogen atoms not shown explicitly may also be replaced by D, and the symbols and indices have the definitions given in claim 14 .
16 . A compound as claimed in claim 14 , wherein the ligand L when o=1 and p=1 has a structure of the formula (4a), and in that the ligand L when o=1 and p=1 has a structure of the formula (4b):
where the hydrogen atoms not shown explicitly may also be replaced by D, and the symbols and indices have the definitions given in claim 14 .
17 . A compound as claimed in claim 14 , wherein the ligand L has a structure of the formula (7):
where the hydrogen atoms not shown explicitly may also be replaced by D, and the symbols and indices have the definitions given in claim 14 .
18 . A compound as claimed in claim 14 , wherein the substituents are as follows:
R is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 6 carbon atoms or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl groups may each also be deuterated;
R 1 is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 6 carbon atoms or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl groups may each also be deuterated; optionally two adjacent R 1 radicals together may form a ring system;
R 2 is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 6 carbon atoms or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl groups may each also be deuterated, or an optionally deuterated phenyl group which may be substituted by one or more optionally deuterated alkyl groups having 1 to 4 carbon atoms; optionally two adjacent R 2 radicals together may form a ring system.
19 . A compound as claimed in claim 14 , wherein the symbols and indices are as follows:
R is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms, where the alkyl groups may each also be deuterated;
R 1 is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms, where the alkyl groups may each also be deuterated; optionally two adjacent R 1 radicals together may form a ring system;
R 2 is the same or different at each instance and is selected from the group consisting of D, a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 or 4 carbon atoms, where the alkyl groups may each also be deuterated, or an optionally deuterated phenyl group which may be substituted by one or more optionally deuterated alkyl groups having 1 to 4 carbon atoms; optionally two adjacent R 2 radicals together may form a ring system;
m is 1 or 2;
n is the same or different at each instance and is 0, 1 or 2;
o is 1; or o is 0 or 1 when n on the same ligand=1 and R 2 is a phenyl group;
p is 0 or 1;
q is 0 or 1; and
r is 0 or 1.
20 . A compound as claimed in claim 14 , wherein the ligand L has a structure of the formula (8):
where the hydrogen atoms not shown explicitly may also be replaced by D, R, R 1 , R 2 and o have the definitions given in claim 14 , p=0 or 1, q=0 or 1 and r=0 or 1.
21 . A compound as claimed in claim 14 , wherein the ligand L has a structure of the formula (9):
where the hydrogen atoms not shown explicitly may also be replaced by D, R, R 1 and R 2 have the definitions given in claim 14 , q=0 or 1 and r=0 or 1.
22 . A process for preparing a compound as claimed in claim 14 by reaction of the free ligand L with iridium alkoxides of the formula (Ir-1), with iridium ketoketonates of the formula (Ir-2), with iridium halides of the formula (Ir-3) or with iridium carboxylates of the formula (Ir-4), or with iridium compounds that bear both alkoxide and/or halide and/or hydroxy and/or ketoketonate radicals,
where R has the definitions given in claim 14 , Hal=F, Cl, Br or I, and the iridium reactants may also take the form of the corresponding hydrates.
23 . A formulation comprising at least one compound as claimed in claim 14 and at least one solvent.
24 . A method comprising incorporating the compound as claimed in claim 14 in an electronic device.
25 . An electronic device comprising at least one compound as claimed in claim 14 .
26 . The electronic device as claimed in claim 25 which is an organic electroluminescent device, wherein the compound is used as an emitting compound in one or more emitting layers.