Materials for organic electroluminescent devices

1. A compound of formula (1-1) or formula (1-2)

where the symbols used are as follows:

X is O or S;

Y is S or CR 2 ;

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 R radicals, where Ar comprises only aryl groups or heteroaryl groups having up to 15 aromatic ring atoms and no carbazolyl groups as heteroaryl groups, and no 9,9′-spirobifluorene groups;

R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R substituents bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic aliphatic ring system which may be substituted by one or more R 4 radicals;

R 1 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 1 substituents or two R 1 and R 3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

R 2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 2 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

R 3 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 1 and R 3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

Ar 1 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 R 4 radicals; at the same time, two Art radicals bonded to the same phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R 4 ), C(R 4 ) 2 , O and S;

R4 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(R 5 ) 2 , C(═O)R 5 , 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 R 5 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 5 C═CR 5 , C═O, C═S, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 5 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 5 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 5 radicals; at the same time, it is optionally possible for two R 4 substituents bonded to the same carbon atom or adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 5 radicals;

R 5 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 R 5 substituents together to form a mono- or polycyclic, aliphatic ring system,

wherein in formula (1-2) X is O and/or Y is CR 2 .

2. The compound according to claim 1 , wherein X is O.

3. The compound according to claim 1 , wherein Y is CR 2 .

4. The compound according to claim 1 , wherein the compound is a compound of the formula (2)

where the symbols have the definitions given in claim 1 , and where one R 2 and one R 4 bonded to a carbon atom are replaced by the single bond.

5. The compound according to claim 1 , wherein the compound is a compound of one of the formulae (2-1) and (2-2),

where the symbols have the definitions given in claim 1 , and where one R 2 in formula (2-1) and one R 4 bonded to a carbon atom in formula (2-2) are replaced by the single bond.

6. The compound according to claim 5 , wherein, in formula (2-2), the R 2 replaced by the single bond is not arranged on the six-membered ring bonded to the nitrogen atom.

7. A mixture comprising at least one compound according to claim 1 and at least one further compound and/or at least one solvent.

8. A method comprising utilizing the compound according to claim 1 or the mixture according to claim 7 in an electronic device.

9. An electronic device comprising at least one compound according to claim 1 or the mixture according to claim 7 .

10. The electronic device according to claim 9 , wherein it is an organic electroluminescent device.

11. The electronic device according to claim 10 , wherein the compound is used in an emitting layer, or in a hole transport layer or in an electron blocker layer.

12. The compound according to claim 1 , wherein X is O and Y is CR 2 .

13. The compound according to claim 1 , wherein Ar is selected from phenyl, ortho-, meta- or para-biphenyl, terphenyl, quaterphenyl, or 1-, 2-, 3- or 4-fluorenyl, and Y is CR 2 and X is O.

14. A compound of formula (1-1) or formula (1-2)

where the symbols used are as follows:

X is O or S;

Y is S or CR 2 ;

wherein in formula (1-2) X is O and/or Y is CR 2 ;

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 R radicals, where Ar comprises only aryl groups or heteroaryl groups having up to 15 aromatic ring atoms and no carbazolyl groups as heteroaryl groups, and no 9,9′-spirobifluorene groups;

R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R substituents bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic aliphatic ring system which may be substituted by one or more R 4 radicals;

R 1 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 1 substituents or two R 1 and R 3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

R 2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 2 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

R 3 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , 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 R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C═O, C═S, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R 4 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals; at the same time, it is optionally possible for two R 1 and R 3 substituents bonded to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 4 radicals;

Ar 1 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 R 4 radicals; at the same time, two Art radicals bonded to the same phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R 4 ), C(R 4 ) 2 , O and S;

R 4 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(R 5 ) 2 , C(═O)R 5 , 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 R 5 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 5 C═CR 5 , C═O, C═S, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 R 5 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 5 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 5 radicals; at the same time, it is optionally possible for two R 4 substituents bonded to the same carbon atom or adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 5 radicals;

R 5 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 R 5 substituents together to form a mono- or polycyclic, aliphatic ring system.

15. The compound according to claim 14 , wherein X is O.

16. The compound according to claim 14 , wherein Y is CR 2 .

17. The compound according to claim 14 , wherein the compound is a compound of the formula (2)

wherein the symbols have the definitions given in claim 14 , and where one R 2 and one R 4 bonded to a carbon atom are replaced by the single bond.

18. The compound according to claim 14 , wherein the compound is a compound of one of the formulae (2-1) and (2-2),

wherein the symbols have the definitions given in claim 14 , and where one R 2 in formula (2-1) and one R 4 bonded to a carbon atom in formula (2-2) are replaced by the single bond.

19. The compound according to claim 18 , wherein, in formula (2-2), the R 2 replaced by the single bond is not arranged on the six-membered ring bonded to the nitrogen atom.

20. A mixture comprising at least one compound according to claim 14 and at least one further compound and/or at least one solvent.