Patent ID: 11932659
Assignee: UDC IRELAND LIMITED
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  H  Y | IPC C  H

Claim 0:
1. A compound of formula (1):

MArpBArpmRBn  Formula (1)

wherein
M is the same or different in each instance and is an organometallic iridium complex comprising one tripodal, hexadentate, trianionic ligand;
Ar is the same or different in each instance and is a linear-bonded arylene group which has 6 to 30 aromatic ring atoms or a linear-bonded heteroarylene group which has 6 to 30 aromatic ring atoms and is optionally substituted by one or more R radicals;
B is a group of formula (2):, wherein
the dotted lines denote the linkages of this group to Ar or to RB;
Y1, Y2, and Y3 
are the same or different in each instance and are CR2, CRr2—CR2, CR2—CR2—CR2, CR2—CR2—CR2—CR2, CR═CR, or an ortho-bonded phenylene group which is optionally substituted by one or more R radicals; and wherein the Y1, Y2, and/or Y3 groups are optionally joined to one another by a single bond or via R radicals so as to define an oligocyclic group;

RB is the same or different in each instance and is M or H, D, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group is optionally substituted in each case by one or more R1 radicals, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R1 radicals;
R is the same or different in each instance and is H, D, F, Cl, Br, I, N(R1)2, CN, NO2, OR′, SR′, COOH, C(═O)N(R′)2, Si(R1)3, B(OR′)2, C(═O)R′, P(═O)(R′)2, S(═O)R′, S(═O)2R′, OSO2R1, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group is optionally substituted in each case by one or more R1 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by R1C═CR1, C≡C, Si(R1)2, C═O, NR1, 0, S, or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R1 radicals; and wherein two R radicals together optionally define a ring system;
R1 is the same or different in each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group is optionally substituted in each case by one or more R2 radicals, wherein one or more nonadjacent CH2 groups are optionally replaced by R2C═CR2, C≡C, Si(R2)2, C═O, NR2, O, S, or CONR2 or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R2 radicals; and wherein two or more R1 radicals together optionally define a ring system;
R2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by F;
n is 1, 2, 3, 4, 5, or 6;
p is the same or different in each instance and has a value from 1 to 100;
q is the same or different in each instance and has a value from 0 to 100; and
m is the same or different in each instance and has a value from 1 to 100;
wherein the tripodal, hexadentate ligand comprises three bidentate sub-ligands, which are the same or different, and coordinate to an iridium atom and the three bidentate sub-ligands are joined via a bridge of formula (3) or (4):, wherein
the dotted line denotes the bond of the bidentate sub-ligands to this structure;
X1 is the same or different in each instance and is CR or N;
A1 is the same or different in each instance and is C(R)2 or O;
A2 is the same or different in each instance and is CR, P(═O), B, or SiR, with the proviso that, when A2 is P(═O), B, or SiR, A1 is O and the A bonded to said A2 is not —C(═O)—NR1— or —C(═O)—O—;
A is the same or different in each instance and is —CR═CR—, —C(═O)—NR1—, —C(═O)—O—, —CR2—CR2—, or a group of formula (5):, wherein
the dotted line denotes the position of the direct bond of the bidentate sub-ligands to this structure and * denotes the position of the direct bond of the group of formula (5) to the central cyclic group in formula (3) or formula (4);
wherein in formula (3) and formula (4) at least one group A is a group of formula (5);

X2 is the same or different in each instance and is CR or N or two adjacent X2 groups together are NR, O, or S, so as to define a five-membered ring, and the remaining X2 groups are the same or different in each instance and are CR or N; or two adjacent X2 groups together are CR or N when one of the X3 groups in the cycle is N so as to define a five-membered ring; with the proviso that not more than two adjacent X2 groups are N;
X3 is C in each instance or one X3 group is N and the other X3 group in the same cycle is C, with the proviso that two adjacent X2 groups together are CR or N when one of the X3 groups in the cycle is N;
R′ is the same or different in each instance and is H, D, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group in each case is optionally substituted by one or more R1 radicals and wherein one or more nonadjacent CH2 groups are optionally replaced by Si(R1)2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R1 radicals; and
wherein the three bidentate sub-ligands, in addition to via the bridges of formulae (3) or (4), are also optionally closed via a further bridge to form a cryptate.