Organic semiconducting material and use thereof in organic devices

1. A compound of formula I:

EWG1-(T1) a -(T2) b -(Z) c -(T3) d -(T4) e -EWG2,

wherein parameters a, b, d and e are each independently of one another 0 or 1,

wherein parameter c is 1, 2, 3, 4 or 5,

wherein group Z is a block of two groups M and N, linked as *-M-N—* or *—N-M-*, where * designates the attachment to the groups T1 to T4 or electron-withdrawing groups EWG1 and EWG2,

wherein the group M each independently of one another are selected from:

wherein the group N each independently of one another are selected from:

wherein the group M and the group N are each linked such that at least one N atom of the group M and one O atom of the group N are each joined to one another via 2 C atoms, and designates the

attachment to other groups in the compound of the formula I,

wherein X 1 -X 16 independently of one another is selected from N or C—R, with the proviso that in the groups of the formula 3 and 6, in each case one group from the groups X 8 /X 7 and X 16 /X 15 designates the attachment to the other groups in the compound of the formula I,

wherein each R independently of any other is selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted and C atoms of the C 1 -C 20 alkyl may be replaced by heteroatoms; C 2 -C 20 alkenyl, O-alkyl, S-alkyl, O-alkenyl, S-alkenyl, alkynyl, aryl, heteroaryl, wherein hydrogen atoms may be substituted in all groups; CN, NR′R″, with R′ and R″ each independently of one another being selected from: H, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted and C atoms of the C 1 -C 20 alkyl may be replaced by heteroatoms,

wherein R 1 to R 3 each independently of one another are selected from a group composed of H, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted and C atoms of the C 1 -C 20 alkyl may be replaced by heteroatoms; substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, CN,

wherein each Q independently of any other is selected from S, O, Se, NR′″, where R′″ is defined as for R 1 to R 3 ,

wherein the electron-withdrawing groups EWG1 and EWG2 independently of one another are selected from:

and designates the attachment to the groups T1 to T4 or the group Z in the compound of the formula I,

wherein R 4 and R 12 each independently of one another is selected from H, CN, COOR, with the proviso that R 4 and R 12 cannot both be H,

wherein R is selected from the same group of compounds as defined in the case of R 1 to R 3 ,

wherein each R 13 independently of any other is selected from a group: H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, where, if the substituent R 5 or R 6 is present in the compound of the formula I, a ring closure between R 5 with R 13 or R 6 with R 13 is possible, with the proviso that the double bond from formula 11 is located in each case between R 5 and R 13 or between R 6 and R 13 ,

wherein V is O, S; Y is O, S, C(CN) 2 ; and U is O, S, C(CN) 2 ,

wherein R 7 and R 8 each independently of one another is selected from a group H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, where for each of the electron-withdrawing groups EWG1 and EWG2, each independently of one another in each case for each C═C double bond, both the E-isomer and the Z-isomer may be present,

wherein the groups T1, T2, T3 and T4 each independently of one another are selected from:

wherein designates the attachment to the other groups in the compound of the formula I,

wherein R5 and R6 each independently of one another is selected from a group: H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, wherein, if the substituent R 13 is present in the compound of the formula I, a ring closure may exist between R 5 with R 13 or R 6 with R 13 , with the proviso that between R 5 and R 13 or between R 6 and R 13 in each case the double bond from formula 11 is located, is possible,

wherein W 1 to W 8 each independently of one another is selected from N, CR, where R is defined as described above,

wherein X 17 to X 27 independently of one another is selected from C—R, where R is defined as described above, and with the proviso that in the groups of the formulae 12, 13 and 14, in each case one group from the groups X 20 /X 21 , X 23 /X 24 and X 26 /X 27 designates the attachment to the other groups in the compound of the formula I,

wherein A is S, O, NR″″, Se,

wherein Q is S, O, NR″″, Se, and

wherein for the groups A and Q, the substituent R″″ in each case independently of any other is selected from H, CN, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where the H atoms of the C 1 -C 20 alkyl may be substituted; C 2 -C 20 alkenyl, O-alkyl, S-alkyl, O-alkenyl, S-alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

2. The compound according to claim 1 , wherein the parameter c is 1.

3. The compound according to claim 1 , wherein the electron-withdrawing groups EWG1 or EWG2 are the following group:

4. The compound according to claim 3 , wherein R 4 and R 12 are CN.

5. The compound according to claim 1 , wherein at least one of the parameters a, b, d and e is 0.

6. The compound according to claim 1 , wherein c=1 and in the group Z, the group M is the group of formula 1:

7. The compound according to claim 6 , wherein X 1 and X 2 are C—R, with each R independently of any other selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl.

8. The compound according to claim 6 , wherein in the group Z, the group N is the group of formula 4:

9. The compound according to claim 8 , wherein X 9 and X 10 are C—R, with each R independently of any other being selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl.

10. The compound according to claim 5 , wherein parameter b is 1 and group T2 is the group of formula 10:

11. The compound according to claim 10 , wherein A is S or O.

12. The compound according to claim 11 , wherein in X 17 and X 18 , R independently at each occurrence is selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl.

13. The compound according to claim 5 , wherein parameter d=1 and the group T3 is selected from the groups of formulae 10 or 11:

respectively.

14. The compound according to claim 13 , wherein A ═S or O.

15. The compound according to claim 14 , wherein R in X 17 and X 18 independently at each occurrence is selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, R 5 and R 6 each independently of one another are selected from H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, and where, if the substituents R 5 and R 6 are present in the compound, a ring closure may exist between R 5 with R 13 or R 6 with R 13 , with the proviso that the double bond from formula 11 is located between R 5 and R 13 or between R 6 and R 13 .

16. The compound according to claim 15 , where the ring closure between the substituents R 5 with R 13 or R 6 with R 13 is present in the form of an optionally substituted cyclopentenyl ring or of an optionally substituted cyclohexenyl ring.

17. The compound according to claim 5 , wherein the parameter e=1 and the group T4 is a group of formula 10 or 11:

respectively.

18. The compound according to claim 17 , wherein A ═O or S.

19. The compound according to claim 18 , wherein in X 17 and X 18 , R is selected independently of any other from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl.

20. The compound according to claim 5 , wherein the parameter a=1 and the group T1 is a group of formula 10 or 11:

respectively.

21. The compound according to claim 20 , wherein A ═S or O.

22. The compound according to claim 21 , wherein R in X 17 and X 18 independently at each occurrence is selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, and R5 and R6 are each selected independently of one another from H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, where, if the substituent R 5 and R 6 is present in the compound, a ring closure between R 5 with R 13 and also between R 6 with R 13 is may exist, with the proviso that the double bond from formula 11 is located between R 5 and R 13 or between R 6 and R 13 .

23. The compound according to claim 21 , having the following structural formula II:

24. The compound according to claim 23 , wherein each A is O or S independently of one another.

25. The compound according to claim 23 , wherein independently of one another X 17 , X 18 , X 1 , X 2 , X 9 and X 10 are C—R, where R independently at each occurrence is selected from a group composed of H, halogen, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, and R 6 and R 6 each independently of one another are selected from H, CN, F, aryl, heteroaryl, C 2 -C 20 alkenyl, alkynyl, branched or linear, cyclic or open-chain C 1 -C 20 alkyl, where hydrogen atoms of the C 1 -C 20 alkyl may be substituted, and where, if the substituents R 5 and R 6 are present, a ring closure may be formed between R 5 with R 13 or R 6 with R 13 .

26. The compound according to claim 23 , wherein the parameter c is 1.

27. The compound according to claim 23 , wherein the parameter b is 1.

28. The compound according to claim 23 , wherein the parameter e is 1.

29. The compound according to claim 23 , wherein R 4 and R 12 each independently of one another are selected from H and CN, with the proviso that R 4 and R 12 cannot both be H.

30. Use of the compound according to claim 1 in an organic electronic component.

31. The use according to claim 30 , wherein the organic electronic component is an organic photoactive element, optionally a solar cell.

32. An organic electronic device comprising the compound according to claim 1 .

33. The organic electronic device according to claim 32 , comprising an electrode and a counterelectrode and at least one organic photoactive layer between the electrode and the counterelectrode, wherein the organic photoactive layer comprises the compound.