Organic electroluminescent apparatus
AssigneeMerck Patent GmbH
InventorsAmir Hossain PARHAM, Christian EHRENREICH
Life of this patent
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Abstract
The present invention relates to an organic electroluminescent device comprising a mixture comprising an electron-transporting host material and a hole-transporting host material, and to a formulation comprising a mixture of the host materials and to a mixture comprising the host materials. The electron-transporting host material corresponds to a compound of the formula (1) from the class of dibenzofuran or dibenzothiophene derivatives containing a substituted pyridine, pyrimidine or triazine unit and a substituted further dibenzofuran or dibenzothiophene unit.
Claims16
-15. (canceled)
An organic electroluminescent device comprising an anode, a cathode and at least one organic layer, containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of the formula (1) as host material 1 and at least one compound of the formula (2) as host material 2
- where the symbols and indices used are as follows:
- X is the same or different at each instance and is CR0 or N, where at least one symbol X is N;
- X2 is the same or different at each instance and is CH, CR1 or N, where not more than 2 symbols X2 can be N;
- Y and Y1 are the same or different at each instance and are selected from O and S;
- L is the same or different at each instance and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms;
- L1 is the same or different at each instance and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms;
- R0 at each instance is independently H, D or an unsubstituted or partly or fully deuterated aromatic ring system having 6 to 18 carbon atoms;
- R* at each instance is independently D or an aromatic or heteroaromatic ring system that has 6 to 18 carbon atoms and may be partly or fully deuterated;
- R# is the same or different at each instance and is selected from the group consisting of D, F, Cl, Br, I, CN, NO2, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, Si(R2)2, C═O, C═S, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
- R is the same or different at each instance and is selected from the CN group, an aromatic ring system having 6 to 40 aromatic ring atoms and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, where the ring systems may be substituted by one or more R2 radicals and where the heteroaromatic ring system is bonded via N when the heteroaromatic ring system contains a nitrogen atom;
- R1 is the same or different at each instance and is selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms;
- at the same time, it is possible for two substituents R1 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R2 radicals;
- R2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, NH2, N(R3)2, C(═O)Ar1, C(═O)H, C(═O)R3, P(═O)(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by HC═CH, R3C═CR3, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NH, NR3, O, S, CONH or CONR3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems, where it is optionally possible for two or more adjacent substituents R2 to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R3 radicals;
- R3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms;
- at the same time, it is possible for two or more adjacent R3 substituents together to form a mono- or polycyclic, aliphatic ring system;
- Ar1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R3 radicals;
- at the same time, two Ar1 radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R3), C(R3)2, O and S;
- Ar2 and Ar3 at each instance are each independently an aryl or heteroaryl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
- A at each instance is independently a group of the formula (3) or (4),
- Ar at each instance is in each case independently an aryl group which has 6 to 40 aromatic ring atoms and may be substituted by one or more R# radicals, or a heteroaryl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R# radicals;
- * indicates the binding site to the formula (2);
- a, b, c at each instance are each independently 0 or 1, where the sum total of the indices at each instance a+b+c is 1;
- m and o at each instance are independently 0, 1, 2, 3 or 4;
- n and p at each instance are each independently 0, 1, 2 or 3;
- and
- q, r, s, t at each instance are each independently 0 or 1.
A mixture comprising at least one compound of the formula (1) as host material 1 and at least one compound of the formula (2) as host material 2
- where the symbols and indices used are as follows:
- X is the same or different at each instance and is CR0 or N, where at least one symbol X is N;
- X2 is the same or different at each instance and is CH, CR1 or N, where not more than 2 symbols X2 can be N;
- Y and Y1 are the same or different at each instance and are selected from O and S;
- L is the same or different at each instance and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms;
- L1 is the same or different at each instance and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms;
- R0 at each instance is independently H, D or an unsubstituted or partly or fully deuterated aromatic ring system having 6 to 18 carbon atoms;
- R* at each instance is independently D or an aromatic or heteroaromatic ring system that has 6 to 18 carbon atoms and may be partly or fully deuterated;
- R# is the same or different at each instance and is selected from the group consisting of D, F, Cl, Br, I, CN, NO2, C(═O)R2, P(═O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, Si(R2)2, C═O, C═S, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
- R is the same or different at each instance and is selected from the CN group, an aromatic ring system having 6 to 40 aromatic ring atoms and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, where the ring systems may be substituted by one or more R2 radicals and where the heteroaromatic ring system is bonded via N when the heteroaromatic ring system contains a nitrogen atom;
- R1 is the same or different at each instance and is selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms;
- at the same time, it is possible for two substituents R1 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R2 radicals;
- R2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, NH2, N(R3)2, C(═O)Ar1, C(═O)H, C(═O)R3, P(═O)(Ar1)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by HC═CH, R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NH, NR3, O, S, CONH or CONR3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems, where it is optionally possible for two or more adjacent substituents R2 to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R3 radicals;
- R3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms;
- at the same time, it is possible for two or more adjacent R3 substituents together to form a mono- or polycyclic, aliphatic ring system;
- Ar1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R3 radicals;
- at the same time, two Ar1 radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R3), C(R3)2, O and S;
- Ar2 and Ar3 at each instance are each independently an aryl or heteroaryl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
- A at each instance is independently a group of the formula (3) or (4),
- Ar at each instance is in each case independently an aryl group which has 6 to 40 aromatic ring atoms and may be substituted by one or more R# radicals, or a heteroaryl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R# radicals;
- * indicates the binding site to the formula (2);
- a, b, c at each instance are each independently 0 or 1, where the sum total of the indices at each instance a+b+c is 1;
- m and o at each instance are independently 0, 1, 2, 3 or 4;
- n and p at each instance are each independently 0, 1, 2 or 3;
- and
- q, r, s, t at each instance are each independently 0 or 1.
Dependencies are inferred from the claim text.