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US 12,419,192 B2Granted
Organic electroluminescence devices
AssigneeMerck Patent GmbH
InventorsAmir Parham, Jonas Kroeber, Jens Engelhart, Anja Jatsch, Christian Eickhoff, Christian Ehrenreich, Dominik Joosten
Life of this patent
Estimating the term…
Abstract
The invention relates to organic electroluminescence devices containing indone carbazole derivatives.
Claims13
An organic electroluminescent device comprising anode, cathode and at least one emitting layer containing at least one phosphorescent compound, characterized in that the emitting layer contains at least one compound of formula (1)
- where the symbols and indices used are as follows:
- X two adjacent X are a group of the following formula (2), and the two other X are CR,
- where the two dotted bonds represent the linkage of this group;
- HetAr is an electron-deficient heteroaryl group which is selected from the groups of formulae (HetAr-2), (HetAr-4), (HetAr-5), and (HetAr-7)
- where (HetAr-2) is not a quinazoline group;
- Y is the same or different at each instance and is CR or N, with the proviso that at least two symbols Y and not more than three symbols Y are N;
- R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R1)2, N(Ar′)2, CN, NO2, OR1, SR1, COOR1, 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 an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R1)2, C═O, NR1, O, S or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals;
- R′ is the same or different at each instance and is a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the straight-chain, branched or cyclic alkyl group may in each case be substituted by one or more R1 radicals and where one or more nonadjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R1 radicals;
- it is also possible here for two R′ radicals together to form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
- Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals;
- R1 if the same or different at 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 an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by 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 may be substituted in each case by one or more R2 radicals;
- it is possible here for two or more R1 radicals together to form a ring system;
- R2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which it is also possible for one or more hydrogen atoms to be replaced by F;
- m is 0, 1 or 2;
- and
- n is the same or different at each instance and is 0, 1, 2, 3 or 4.
13 more elements
A formulation comprising at least one compound of formula (1)
- where the symbols and indices used are as follows:
- X two adjacent X are a group of the following formula (2), and the two other X are CR,
- where the two dotted bonds represent the linkage of this group;
- HetAr is an electron-deficient heteroaryl group which is selected from the group consisting of formulae (HetAr-2), (HetAr-4), (HetAr-5), and (HetAr-7)
- where (HetAr-2) is not a quinazoline group;
- Y is the same or different at each instance and is CR or N, with the proviso that at least two symbols Y and not more than three symbols Y are N;
- R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R1)2, N(Ar′)2, CN, NO2, OR1, SR1, COOR1, 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 an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals and where one or more nonadjacent CH2 groups may be replaced by Si(R1)2, C═O, NR1, O, S or CONR1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals;
- R′ is the same or different at each instance and is a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the straight-chain, branched or cyclic alkyl group may in each case be substituted by one or more R1 radicals and where one or more nonadjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R1 radicals;
- it is also possible here for two R′ radicals together to form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system;
- Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals;
- R1 if the same or different at 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 an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by 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 may be substituted in each case by one or more R2 radicals;
- it is possible here for two or more R1 radicals together to form a ring system;
- R2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which it is also possible for one or more hydrogen atoms to be replaced by F;
- m is 0, 1 or 2;
- and
- n is the same or different at each instance and is 0, 1, 2, 3 or 4
- and at least one phosphorescent compound and at least one solvent.
14 more elements
Dependencies are inferred from the claim text.