Patent ID: 11917901
Assignee: UDC IRELAND LIMITED
Field: Electrical machinery, apparatus, energy (Electrical engineering)
Classification: CPC H  C  Y | IPC C  H

Claim 19:
20. A compound of formula (1):

M(L)n(L′)m  (1)

which comprises a moiety M(L)n of formula (2):, wherein

M is iridium or platinum;
CyC is an aryl or heteroaryl group having 5 to 18 aromatic ring atoms or a fluorene group, wherein CyC is coordinated to M via a carbon atom, is optionally substituted by one or more radicals R, and is bonded to CyD via a covalent bond wherein CyC and CyD are optionally linked to one another via a group selected from the group consisting of C(R1)2, C(R1)2—C(R1)2—, NR1, O, and S;
CyD is a heteroaryl group having 5 to 18 aromatic ring atoms, wherein CyD is coordinated to M via a neutral nitrogen atom or via a carbene carbon atom, is optionally substituted by one or more radicals R, and is bonded to CyC via a covalent bond wherein CyD and CyC are optionally linked to one another via a group selected from the group consisting of C(R1)2, C(R1)2—C(R1)2—, NR1, O, and S;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R1)2, CN, NO2, OH, COOH, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1, P(═O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R1, wherein one or more non-adjacent CH2 groups is optionally replaced by R1C═CR1, C≡C, Si(R1)2, C═O, NR1, O, S, or CONR1 and wherein one or more H atoms is optionally replaced by D, F, Cl, Br, I, or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R1, an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R1, or a diarylamino group, diheteroarylamino group, or arylheteroaryl-amino group having 10 to 40 aromatic ring atoms optionally substituted by one or more radicals R1; and wherein two adjacent radicals R optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R2, wherein one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, —C≡C, Si(R2)2, C═O, NR2, O, S, or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R2, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R2, an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R2, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms optionally substituted by one or more radicals R2; and wherein two or more adjacent radicals R1 with one another or R1 with R optionally form a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system;
R2 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by F; and wherein two or more substituents R2 optionally form a mono- or polycyclic, aliphatic ring system with one another;
L′ is, identically or differently on each occurrence, a co-ligand;
n is 1, 2, or 3;
m is 0, 1, 2, 3, or 4;
and wherein
a plurality of ligands L are optionally linked to one another or L is optionally linked to L′ via a single bond or a divalent or trivalent bridge and thus form a tridentate, tetradentate, pentadentate, or hexadentate ligand system;
a substituent R optionally additionally coordinates to the metal; and
wherein CyD contain(s) two adjacent carbon atoms which are each substituted by radicals R, wherein the respective radicals R, together with the C atoms, form a ring of formula (3) or (4):, wherein R1 and R2 are as defined above and the dashed bonds indicate the linking of the two carbon atoms in the ligand;
A1 is C(R3)2, S, or NR3;
A2 is C(R1)2, O, S, NR3, or C(═O);
A3 is C(R3)2, O, S, NR3, or C(═O);
G is an alkylene group having 1, 2 or 3 C atoms and is optionally substituted by one or more radicals R2, —CR2═CR2—, or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms optionally substituted by one or more radicals R2; and
R3 is, identically or differently on each occurrence, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R2 wherein one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, —C≡C, Si(R2)2, C═O, NR2, O, S, or CONR2 and wherein one or more H atoms is optionally replaced by D or F, an aromatic or hetero aromatic ring system having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R2, an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R2; wherein two radicals R3 bonded to the same carbon atom optionally form an aliphatic or aromatic ring system with one another to form a spiro system; and wherein R3 optionally forms an aliphatic ring system with an adjacent radical R or R1;
with the proviso that two heteroatoms are not bonded directly to one another in A1-A2-A3 and
with the proviso that the radicals R on CyC do not join together to form a ring with the radicals R on CyD.