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US 12,454,542 B2Granted
Metal complexes for use as emitters in organic electroluminescence devices
AssigneeUDC Ireland Limited
InventorsPhilipp Stoessel, Christian Ehrenreich
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Abstract
The present invention relates to metal complexes which are substituted by aromatic and icylic aliphatic substituents and are suitable for use as emitters in organic electroluminescent devices. The electronic devices of the invention, especially organic electroluminescent devices, are notable for advantages that are not accompanied by a deterioration in the further electronic properties. The invention provides a compound of the following formula (1): wherein B is a group of the following formula (2):
Claims20
A compound of formula (1):
- wherein
- M is the same or different in each instance and is an organometallic iridium complex comprising three bidentate, monoanionic ligands or one tripodal, hexadentate, trianionic ligand;
- Ar is the same or different in each instance and is a linear-bonded arylene 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, CR2—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, OR1, SR1, 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 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, O, 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, OSOR2, 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;
- and
- provided that Ar is substituted by at least two alkyl groups.
19 more elements
Dependencies are inferred from the claim text.