Materials for electronic devices
The present application relates to a compound of a formula (I) which comprises a benzene group that is substituted with a group selected from carbazole derivatives and bridged amines and with an electron attracting group, wherein the two groups are located in the ortho-position in relation to one another. The present application further relates to the use of the compound of the formula (I) in an electronic device, and to a method of producing the compound of the formula (I).
1. A compound of the formula (I)
or a compound containing exactly two or three units of the formula (I) joined to one another via a single bond or an L group,
where:
L is any divalent or trivalent organic group;
A is a group of the formula (A)
bonded via the dotted bond;
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 R 1 radicals;
Y is the same or different at each instance and is a single bond, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, S═O or S(═O) 2 ;
B is the same or different at each instance and is selected from H, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more R 1 radicals, or an aryl group having 6 to 14 aromatic ring atoms, each of which may be substituted by one or more R 1 radicals;
R A is the same or different at each instance and is CF 3 , CN, and an E group, which is an aryl or heteroaryl group which has 6 to 14 aromatic ring atoms and may be substituted by one or more R 1 radicals, and which contains one or more V groups as constituents of the aromatic ring, where the V groups are the same or different at each instance and are selected from ═N—, ═C(F)—, ═C(CN)— and ═C(CF 3 )—, and where the heteroaryl group is not bonded via a nitrogen atom;
R B is selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 1 radicals, and an aryl group having 6 to 14 aromatic ring atoms, which may be substituted by one or more R 1 radicals;
R 1 is the same or different at each instance and is H, D, F, C(═O)R 2 , CN, Si(R 2 ) 3 , N(R 2 ) 2 , P(═O)(R 2 ) 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, where the abovementioned groups may each be substituted by one or more R 2 radicals and where one or more CH 2 groups in the abovementioned groups may be replaced by —R 2 C═CR 2 —, —C≡C—,Si(R 2 ) 2 , C═O, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, where two or more R 1 radicals may be joined to one another and may form a ring;
R 2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F; at the same time, two or more R 2 substituents may be joined to one another and may form a ring.
2. The compound as claimed in claim 1 , wherein the L group is a divalent group selected from alkylene groups having 1 to 20 carbon atoms, in which one or more CH 2 groups may be replaced by Si(R 1 ) 2 , O, S, C═O, C═NR 1 , C═O—O, C═O—NR 1 , NR 1 , P(═O)(R 1 ), SO or SO 2 and which may be substituted by one or more R 1 radicals, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more R 1 radicals, or is a trivalent group selected from aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more R 1 radicals.
3. The compound as claimed in claim 1 , wherein Ar 1 is the same or different at each instance and is an aromatic ring system which has 6 to 20 aromatic ring atoms and may be substituted by one or more R 1 radicals.
4. The compound as claimed in claim 1 , wherein the Y group is the same or different at each instance and is a single bond, C(R 1 ) 2 , NR 1 , O or S.
5. The compound as claimed in claim 1 , wherein the B group is the same or different at each instance and is H.
6. The compound as claimed in claim 1 , wherein the two R A radicals are the same or different and are CN.
7. The compound as claimed in claim 1 , wherein R B is the same or different at each instance and is H.
8. The compound as claimed in claim 1 , wherein the compound of the formula (I) corresponds to formula (I-3)
where the A and R A groups are each as defined in claim 1 .
9. A process for preparing the compound of formula (I) as claimed in claim 1 , which comprises introducing at least one carbazole derivative by nucleophilic aromatic substitution or Buchwald coupling, or in that at least one electron-deficient heteroaryl group is introduced by Suzuki coupling.
10. An oligomer containing one or more compounds of formula (I) as claimed in claim 1 , wherein the bond(s) to the oligomer may be localized at any positions substituted by R 1 or R 2 in formula (I).
11. An electronic device comprising at least one compound as claimed in claim 1 .
12. An electronic device comprising at least one oligomer as claimed in claim 10 .
13. An organic electroluminescent device comprising anode, cathode and at least one emitting layer, wherein at least one organic layer in the device, selected from emitting layers, comprises at least one compound as claimed in claim 1 .
14. An organic electroluminescent device comprising anode, cathode and at least one emitting layer, wherein at least one organic layer in the device, selected from emitting layers, comprises at least one oligomer as claimed in claim 10 .
15. The compound as claimed in claim 1 , wherein at least one R A radical is CN.
16. The compound as claimed in claim 1 , wherein Ar 1 is phenyl, which may be substituted by one or more radicals R 1 .
17. The compound as claimed in claim 1 , wherein R B is H and B is H.
18. The compound as claimed in claim 1 , wherein
R A is CN,
R B is H,
B is H and
Ar 1 is phenyl, which may be substituted by one or more radicals R 1 .
19. A compound of the formula (I)
where:
A is a group of the formula (A)
bonded via the dotted bond;
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 R 1 radicals;
Y is the same or different at each instance and is a single bond, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , P(═O)R 1 , O, S, S═O or S(═O) 2 ;
B is the same or different at each instance and is selected from H, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more R 1 radicals, or an aryl group having 6 to 14 aromatic ring atoms, each of which may be substituted by one or more R 1 radicals;
R A is the same or different at each instance and is CF 3 , CN, and an E group, which is an aryl or heteroaryl group which has 6 to 14 aromatic ring atoms and may be substituted by one or more R 1 radicals, and which contains one or more V groups as constituents of the aromatic ring, where the V groups are the same or different at each instance and are selected from ═N—, ═C(F)—, ═C(CN)— and ═C(CF 3 )—, and where the heteroaryl group is not bonded via a nitrogen atom;
R B is selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 1 radicals, and an aryl group having 6 to 14 aromatic ring atoms, which may be substituted by one or more R 1 radicals;
R 1 is the same or different at each instance and is H, D, F, C(═O)R 2 , CN, Si(R 2 ) 3 , N(R 2 ) 2 , P(═O)(R 2 ) 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, where the abovementioned groups may each be substituted by one or more R 2 radicals and where one or more CH 2 groups in the abovementioned groups may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, where two or more R 1 radicals may be joined to one another and may form a ring; and
R 2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F; at the same time, two or more R 2 substituents may be joined to one another and may form a ring.