CERIUM (IV) COMPLEXES AND THEIR USE IN ORGANIC ELECTRONICS

Abstract

The present invention relates to an electronic component comprising a cerium IV complex, a doped semi-conductor matrix material comprising the cerium IV complex and at least one electron donor, the use of the cerium IV complex, especially as an organic semi-conductor, as a dopant in organic semiconductor matrix materials and as a charge injector in a charge injection layer, and new cerium IV complexes.

Claims

1. An electronic component comprising hole transport layer and/or a hole injection layer, which comprises at least one compound of the general formula (I.1)
Ce.sup.4+(L.sub.1L.sub.2L.sub.3L.sub.4).sup.4−  (I.1) or mixtures thereof, wherein L.sub.1; L.sub.2; L.sub.3; and L.sub.4 are independently from each other selected from a bidentate ligand having the general formula (I.2) ##STR00044## wherein X and W independently from each other represent O, S or NR.sup.6−; Y represents N or CR.sup.3−; R.sup.1, R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.8−; R.sup.3 represents hydrogen, CN, nitro, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.€-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; R.sup.6 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.8 represents CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.6-C.sub.14-aryl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

2. The electronic component according to claim 1 comprising hole transport layer and/or a hole injection layer, which comprises at least one compound of the general formula (I) ##STR00045## or mixtures thereof, wherein X and W independently from each other represent O, S or NR.sup.6−; Y represents N or CR.sup.3−; R.sup.1, R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.8−; R.sup.3 represents hydrogen, CN, nitro, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6 -alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; R.sup.6 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.8 represents CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.6-C.sub.14-aryl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

3. The electronic component according to claim 1, wherein R.sup.1 and R.sup.2 in ligands of formula (I.2) are independently selected from CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b and the group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 ##STR00046## ##STR00047## where # denotes the bond to the remaining molecule of formula (I.2) and (I), R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; R.sup.4a, R.sup.4b independently represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; and R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−.

4. The electronic component according to claim 3, wherein in A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 and A15 the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently from another selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-haloalkyl.

5. The electronic component according claim 1, wherein in ligands of formula (I.2) Y represents the radical CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro, halogen, CF.sub.3 and the group B consisting B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 and B15 ##STR00048## ##STR00049## where # denotes the bond to the remaining molecule of formula (I.2), R.sup.E, R.sup.G, R.sup.H, R.sup.I and R.sup.J are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; and R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5.

6. The electronic component according to claim 1, wherein in ligands of formula (I.2) R.sup.1 and R.sup.2 are independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, A1, A5, A16 and A17 ##STR00050## where # denotes the bond to the remaining molecule of formula (I.2), and wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-haloalkyl.

7. The electronic component according to claim 1, wherein in ligands of formula (I.2) Y represents a radical CR.sup.3 and wherein R.sup.3 is selected from hydrogen, CN, nitro, halogen, CF.sub.3 and B1 ##STR00051## where # denotes the bond to the remaining molecule of formulae (I.2) and (I), and wherein R.sup.E, R.sup.G, R.sup.H, R.sup.I and R.sup.J are independently selected from hydrogen, CN, fluorine and chlorine.

8. The electronic component according to claim 1, wherein the compounds of formula (I.1) are selected from compounds of formula (I.a′) Ce.sup.4+[(R.sup.1—C(—O)═C(R.sup.3)—C(═O)—R.sup.2)(R.sup.1—C(—O)═C(R.sup.3′)—C(═O)—R.sup.2′)(R.sup.1—C(—O)═C(R.sup.3″)—C(═O)—R.sup.2″) (R.sup.1″′—C(—O)═C(R.sup.3′″)— C(═O)—R.sup.2′″)].sup.4−(I.a′), wherein (R.sup.1, R.sup.2, R.sup.3), (R.sup.1′, R.sup.2′, R.sup.3′), (R.sup.1″, R.sup.2″, R.sup.3″) and (R.sup.1′″, R.sup.2′″, R.sup.3′″) are each selected from the definition given in one line of the following table TABLE-US-00004 R.sup.1, R.sup.1′, R.sup.1′′, R.sup.1′′′ R.sup.2, R.sup.2′, R.sup.2′′, R.sup.2′′′ R.sup.3, R.sup.3′, R.sup.3′′, R.sup.3′′′ methyl methyl H methyl methyl CN methyl methyl F methyl methyl Cl methyl methyl NO.sub.2 methyl methyl pentafluorophenyl methyl methyl tetrafluoro-2- (trifluoromethyl)phenyl methyl methyl tetrafluoro-3- (trifluoromethyl)phenyl methyl methyl tetrafluoro-4- (trifluoromethyl)phenyl methyl methyl tetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyl tetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methyl methyl tetrafluoro-3-benzonitrile methyl methyl tetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl H trifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO.sub.2 trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyl trifluoromethyl tetrafluoro-2- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-3- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl H pentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl F pentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethyl NO.sub.2 pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propyl heptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propyl heptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propyl heptafluoro-n-propyl heptafluoro-n- NO.sub.2 propyl heptafluoro-n-propyl heptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2- propyl (trifluoromethyl)phenyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3- propyl (trifluoromethyl)phenyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4- propyl (trifluoromethyl)phenyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propyl heptafluoro-isopropyl heptafluoro- H isopropyl heptafluoro-isopropyl heptafluoro- CN isopropyl heptafluoro-isopropyl heptafluoro- F isopropyl heptafluoro-isopropyl heptafluoro- Cl isopropyl heptafluoro-isopropyl heptafluoro- NO.sub.2 isopropyl heptafluor-iso-propyl heptafluoro- pentafluorophenyl isopropyl heptafluor-iso-propyl heptafluoro- tetrafluoro-2- isopropyl (trifluoromethyl)phenyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3- isopropyl (trifluoromethyl)phenyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4- isopropyl (trifluoromethyl)phenyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrile isopropyl tert-butyl tert-butyl H tert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyl tert-butyl Cl tert-butyl tert-butyl NO.sub.2 tert-butyl tert-butyl pentafluorophenyl tert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-3- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-4- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyl tert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyl tetrafluoro-2-benzonitrile tert-butyl tert-butyl tetrafluoro-3-benzonitrile tert-butyl tert-butyl tetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl H nonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butyl nonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Cl nonafluoro-n-butyl nonafluoro-n-butyl NO.sub.2 nonafluoro-n-butyl nonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2- (trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3- (trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4- (trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-benzonitrile pentafluorophenyl pentafluorophenyl H pentafluorophenyl pentafluorophenyl CN pentafluorophenyl pentafluorophenyl F pentafluorophenyl pentafluorophenyl Cl pentafluorophenyl pentafluorophenyl NO.sub.2 pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidy 4-pyrimidy H 4-pyrimidy 4-pyrimidy CN 4-pyrimidy 4-pyrimidy F 4-pyrimidy 4-pyrimidy Cl 4-pyrimidy 4-pyrimidy NO.sub.2 4-pyrimidy 4-pyrimidy pentafluorophenyl 4-pyrimidy 4-pyrimidy tetrafluoro-2- (trifluoromethyl)phenyl 4-pyrimidy 4-pyrimidy tetrafluoro-3- (trifluoromethyl)phenyl 4-pyrimidy 4-pyrimidy tetrafluoro-4- (trifluoromethyl)phenyl 4-pyrimidy 4-pyrimidy tetrafluoro-2-pyridyl 4-pyrimidy 4-pyrimidy tetrafluoro-3-pyridyl 4-pyrimidy 4-pyrimidy tetrafluoro-4-pyridyl 4-pyrimidy 4-pyrimidy tetrafluoro-2-benzonitrile 4-pyrimidy 4-pyrimidy tetrafluoro-3-benzonitrile 4-pyrimidy 4-pyrimidy tetrafluoro-4-benzonitrile 2-pyrimidy 2-pyrimidy H 2-pyrimidy 2-pyrimidy CN 2-pyrimidy 2-pyrimidy F 2-pyrimidy 2-pyrimidy Cl 2-pyrimidy 2-pyrimidy NO.sub.2 2-pyrimidy 2-pyrimidy pentafluorophenyl 2-pyrimidy 2-pyrimidy tetrafluoro-2- (trifluoromethyl)phenyl 2-pyrimidy 2-pyrimidy tetrafluoro-3- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl H bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-yl trifluoromethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3′,5′- pentafluoroethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 3′,5′- trifluoromethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 4-fluoro-3- pentafluoroethyl H trifluoromethyl-phenyl 4-fluoro-3- 3,5- H trifluoromethyl-phenyl bisftrifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl H 3,4,5-trifluorophenyl pentafluoroethyl H 4- 4- H (trifluoromethyl) (trifluoromethyl) phenyl phenyl 4- pentafluoroethyl H (trifluoromethyl) phenyl 2,4,6- 2,4,6- H tris(trifluoromethyl) tris(trifluoromethyl) phenyl phenyl 2,4,6- Pentafluoroethyl H tris(trifluoromethyl) phenyl 3,5- 3,5- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4,6- 2,4,6- CN tris(trifluoromethyl) tris(trifluoromethyl) phenyl phenyl 3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,4- 3,4- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,4- trifluoromethyl H bis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,4- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- 3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CN bis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6- pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′- pentafluoroethyl H bis(trifluoromethyl) phenyl)-2,6- bis(trifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF.sub.3 bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl CF.sub.3 bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl CF.sub.3 3,5- pentafluoroethyl CF.sub.3 bis(trifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF.sub.3 4- 4- CF.sub.3 (trifluoromethyl) (trifluoromethyl) phenyl phenyl phenyl phenyl CF.sub.3

9. The electronic component according to claim 1, wherein the compounds of formula (I.1) are selected from compounds of formula (I.a) ##STR00052## wherein R.sup.1, R.sup.2 and R.sup.3 are selected from TABLE-US-00005 R.sup.1 R.sup.2 R.sup.3 methyl methyl H methyl methyl CN methyl methyl F methyl methyl Cl methyl methyl NO.sub.2 methyl methyl pentafluorophenyl methyl methyl tetrafluoro-2-(trifluoromethyl)phenyl methyl methyl tetrafluoro-3-(trifluoromethyl)phenyl methyl methyl tetrafluoro-4-(trifluoromethyl)phenyl methyl methyl tetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyl tetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methyl methyl tetrafluoro-3-benzonitrile methyl methyl tetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl H trifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO.sub.2 trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyl trifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-3-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-4-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl H pentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl F pentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethyl NO.sub.2 pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propyl heptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propyl heptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propyl heptafluoro-n-propyl heptafluoro-n- NO.sub.2 propyl heptafluoro-n-propyl heptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propyl heptafluoro-isopropyl heptafluoro- H isopropyl heptafluoro-isopropyl heptafluoro- CN isopropyl heptafluoro-isopropyl heptafluoro- F isopropyl heptafluoro-isopropyl heptafluoro- Cl isopropyl heptafluoro-isopropyl heptafluoro- NO.sub.2 isopropyl heptafluor-iso-propyl heptafluoro- pentafluorophenyl isopropyl heptafluor-iso-propyl heptafluoro- tetrafluoro-2-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrile isopropyl tert-butyl tert-butyl H tert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyl tert-butyl Cl tert-butyl tert-butyl NO.sub.2 tert-butyl tert-butyl pentafluorophenyl tert-butyl tert-butyl tetrafluoro-2-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-3-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-4-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyl tert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyl tetrafluoro-2-benzonitrile tert-butyl tert-butyl tetrafluoro-3-benzonitrile tert-butyl tert-butyl tetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl H nonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butyl nonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Cl nonafluoro-n-butyl nonafluoro-n-butyl NO.sub.2 nonafluoro-n-butyl nonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-benzonitrile pentafluorophenyl pentafluorophenyl H pentafluorophenyl pentafluorophenyl CN pentafluorophenyl pentafluorophenyl F pentafluorophenyl pentafluorophenyl Cl pentafluorophenyl pentafluorophenyl NO.sub.2 pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidyl 4-pyrimidyl H 4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl 4-pyrimidyl F 4-pyrimidyl 4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO.sub.2 4-pyrimidyl 4-pyrimidyl pentafluorophenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl 2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl 2-pyrimidyl 2-pyrimidyl NO.sub.2 2-pyrimidyl 2-pyrimidyl pentafluorophenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl H bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-yl trifluoromethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3′,5′- pentafluoroethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 3′,5′- trifluoromethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 4-fluoro-3- pentafluoroethyl H trifluoromethyl-phenyl 4-fluoro-3- 3,5- H trifluoromethyl-pheny bis(trifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl H 3,4,5-trifluorophenyl pentafluoroethyl H 4- 4- H (trifluoromethyl)phenyl (trifluoromethyl)phenyl 4- pentafluoroethyl H (trifluoromethyl)phenyl 2,4,6- 2,4,6- H tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 2,4,6- Pentafluoroethyl H tris(trifluoromethyl)phenyl 3,5- 3,5- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4,6- 2,4,6- CN tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)- phenyl 3,4- 3,4- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,4- trifluoromethyl H bis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- 3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CN bis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6- pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′- pentafluoroethyl H bis(trifluoro- methyl)phenyl)-2,6- bisftrifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF.sub.3 bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl CF.sub.3 bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl CF.sub.3 3,5- pentafluoroethyl CF.sub.3 bis(trifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF.sub.3 4- 4-(trifluoromethyl)phenyl CF.sub.3 (trifluoromethyl)phenyl phenyl phenyl CF.sub.3

10. The electronic component according to claim 1, wherein L.sub.1, L.sub.2, L.sub.3 and L.sub.4 have the same meanings.

11. The electronic component according to claim 1 in form of an organic light-emitting diode, an organic solar cell, a photovoltaic cell, an organic diode or an organic transistor, preferably in form of a thin-film transistor, a Perovskite solar cell.

12. The electronic component according to claim 1, having a layer structure, which comprises 2, 3, 4, 5, 6, 7 or more layers.

13. The electronic component according to claim 1, comprising an electron transport layer, which comprises at least of the compound of formula (I.1).

14. A doped semiconductor matrix material comprising at least one electron donor and at least one compound of the formula (I.1) or (I) as defined in any one of claims 1 to 10, wherein the electron donor is preferably selected from 4,4′,4″-tris(N(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA), 4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA), N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD), (2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spirobifluorene (spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine, N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)9,9-spiro-bifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N′-((9H-fluoren-9,9-diyl)bis(4,1-phenylen))bis(N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine) (BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1′-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)N-(6-methoxy-[1,1′-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1′-biphenyl]-4-yl)-N-(4-(6-([1,1-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, N,N-di([1,1-biphenyl]-4-yl)-3-(4-(di([1,1-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(9,9′-spirobi[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-Aamino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine, N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-Aamino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine, 9-(4-(6-(9H-carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole, N-([1,1-biphenyl]-4-yl)-3-(4-([1,1-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, 3-(4-(bis(6-methoxy-[1,1′-biphenyl]-3-yl)amino)phenyl)-N,N-bis(6-methoxy-[1,1-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N1-([1,1-biphenyl]-4-yl)-N1-(4-(6-([1,1′-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, N,N-di([1,1-biphenyl]-4-yl)-4′-(6-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1-biphenyl]-4-amine, N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N,N′-bis(9,9-dimethylfluoren-2-yl)-N,N′-diphenyl-benzidine (BF-DPB), N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1′-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine) (BPAPF), N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-4,4′-diamine (TDMFB), N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD), a mixture of N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and mixtures thereof.

15. A method for the production of organic semiconductor, doping agent in organic semiconductor matrix materials, especially as p-dopant in hole transport layers, electron transport material, charge injector in a charge injection layer, cathode material in organic batteries, electrochromic material, wherein a compound (I.1) or mixtures thereof or of a compound (I) or mixtures thereof, as defined in any one of claims 1 to 10 is employed.

16. A method for the production of organic conductor or as electrochromic material, wherein Ce(III) complex anions obtained by reduction of a compound (I.1) or (I) as defined in any one of claims 1 to 10 or of charge transfer complexes of a compound (I.1) or (I) as defined in any one of claims 1 to 10 with electron donors is employed.

17. (canceled)

18. A compound of the general formula (I.1)
Ce.sup.4+(L.sub.1L.sub.2L.sub.3L.sub.4).sup.4−(I.1), and mixtures thereof, wherein L.sub.1; L.sub.2; L.sub.3; and L.sub.4 are independently from each other a bidentate ligand having the general formula (I.2) ##STR00053## wherein X and W independently from each other represent O or S; Y represents CR.sup.3−; R.sup.1 represents A1 ##STR00054## wherein where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; R.sup.2 represents CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b; R.sup.3 represents hydrogen, CN, nitro and halogen; R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; or compounds of formula (I.a′) Ce.sup.4+[(R.sup.1—C(O)═C(R.sup.3)—C(═O)—R.sup.2)(R.sup.1′—C(—O)═C(R.sup.3′)—C(═O)—R.sup.2′)(R.sup.1″ —C(—O)═C(R.sup.3″)—C(═O)—R.sup.2″) (R.sup.1′′-C(—O)═C(R.sup.3′″—C(═O)—R.sup.2′″)].sup.4− (I.a′), wherein (R.sup.1, R.sup.2, R.sup.3), (R.sup.1′, R.sup.2′, R.sup.3′), (R.sup.1″, R.sup.2″, R.sup.3″) and (R.sup.1′″, R.sup.2′″, R.sup.3′″) are each selected from the definition given in one line of the following table TABLE-US-00006 R.sup.1, R.sup.1′, R.sup.1″, R.sup.1′′′ R.sup.2, R.sup.2′, R.sup.2″, R.sup.2′′′ R.sup.3, R.sup.3′, R.sup.3″, R.sup.3′′′ methyl methyl CN methyl methyl F methyl methyl Cl methyl methyl NO.sub.2 methyl methyl pentafluorophenyl methyl methyl tetrafluoro-2- (trifluoromethyl)phenyl methyl methyl tetrafluoro-3- (trifluoromethyl)phenyl methyl methyl tetrafluoro-4- (trifluoromethyl)phenyl methyl methyl tetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyl tetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methyl methyl tetrafluoro-3-benzonitrile methyl methyl tetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO.sub.2 trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyl trifluoromethyl tetrafluoro-2- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-3- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl H pentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl F pentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethyl NO.sub.2 pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile heptafluoro-n- heptafluoro-n- H propyl propyl heptafluoro-n- heptafluoro-n- CN propyl propyl heptafluoro-n- heptafluoro-n- F propyl propyl heptafluoro-n- heptafluoro-n- Cl propyl propyl heptafluoro-n- heptafluoro-n- NO.sub.2 propyl propyl heptafluoro-n- heptafluoro-n- pentafluorophenyl propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-2- propyl propyl (trifluoromethyl)phenyl heptafluoro-n- heptafluoro-n- tetrafluoro-3- propyl propyl (trifluoromethyl)phenyl heptafluoro-n- heptafluoro-n- tetrafluoro-4- propyl propyl (trifluoromethyl)phenyl heptafluoro-n- heptafluoro-n- tetrafluoro-2-pyridyl propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-3-pyridyl propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-4-pyridyl propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-2-benzonitrile propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-3-benzonitrile propyl propyl heptafluoro-n- heptafluoro-n- tetrafluoro-4-benzonitrile propyl propyl heptafluoro- heptafluoro- H isopropyl isopropyl heptafluoro- heptafluoro- CN isopropyl isopropyl heptafluoro- heptafluoro- F isopropyl isopropyl heptafluoro- heptafluoro- Cl isopropyl isopropyl heptafluoro- heptafluoro- NO.sub.2 isopropyl isopropyl heptafluor-iso- heptafluoro- pentafluorophenyl propyl isopropyl heptafluor-iso- heptafluoro- tetrafluoro-2- propyl isopropyl (trifluoromethyl)phenyl heptafluoro- heptafluoro- tetrafluoro-3- isopropyl isopropyl (trifluoromethyl)phenyl heptafluoro- heptafluoro- tetrafluoro-4- isopropyl isopropyl (trifluoromethyl)phenyl heptafluoro- heptafluoro- tetrafluoro-2-pyridyl isopropyl isopropyl heptafluoro- heptafluoro- tetrafluoro-3-pyridyl isopropyl isopropyl heptafluoro- heptafluoro- tetrafluoro-4-pyridyl isopropyl isopropyl heptafluoro- heptafluoro- tetrafluoro-2-benzonitrile isopropyl isopropyl heptafluoro- heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropyl heptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropyl isopropyl tert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyl tert-butyl Cl tert-butyl tert-butyl NO.sub.2 tert-butyl tert-butyl pentafluorophenyl tert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-3- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-4- (trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyl tert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyl tetrafluoro-2-benzonitrile tert-butyl tert-butyl tetrafluoro-3-benzonitrile tert-butyl tert-butyl tetrafluoro-4-benzonitrile nonafluoro-n- nonafluoro-n- H butyl butyl nonafluoro-n- nonafluoro-n- CN butyl butyl nonafluoro-n- nonafluoro-n- F butyl butyl nonafluoro-n- nonafluoro-n- Cl butyl butyl nonafluoro-n- nonafluoro-n- NO.sub.2 butyl butyl nonafluoro-n- nonafluoro-n- pentafluorophenyl butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-2- butyl butyl (trifluoromethyl)phenyl nonafluoro-n- nonafluoro-n- tetrafluoro-3- butyl butyl (trifluoromethyl)phenyl nonafluoro-n- nonafluoro-n- tetrafluoro-4- butyl butyl (trifluoromethyl)phenyl nonafluoro-n- nonafluoro-n- tetrafluoro-2-pyridyl butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-3-pyridyl butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-4-pyridyl butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-2-benzonitrile butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-3-benzonitrile butyl butyl nonafluoro-n- nonafluoro-n- tetrafluoro-4-benzonitrile butyl butyl pentafluorophenyl pentafluorophenyl H pentafluorophenyl pentafluorophenyl CN pentafluorophenyl pentafluorophenyl F pentafluorophenyl pentafluorophenyl Cl pentafluorophenyl pentafluorophenyl NO.sub.2 pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-3- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-4- (trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidyl 4-pyrimidyl H 4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl 4-pyrimidyl F 4-pyrimidyl 4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO.sub.2 4-pyrimidyl 4-pyrimidyl pentafluorophenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl 2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl 2-pyrimidyl 2-pyrimidyl NO.sub.2 2-pyrimidyl 2-pyrimidyl pentafluorophenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 3,5- trifluoromethyl H bis(trifluoro- methyl)-phenyl phenyl pentafluoroethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl H bis(trifluoro- methyl)-phenyl 3′,5′- pentafluoroethyl H bis(trifluoro- methyl-[1,1′- biphenyl]-4-yl 3′,5′- trifluoromethyl H bis(trifluoro- methyl-[1,1′- biphenyl]-4-yl 4-fluoro-3- pentafluoroethyl H trifluoromethyl- phenyl 4-fluoro-3- 3,5- H trifluoromethyl- bis(trifluoro- phenyl methyl)-phenyl 3,4,5- 3,4,5- H trifluorophenyl trifluorophenyl 3,4,5- pentafluoroethyl H trifluorophenyl 4- 4- H (trifluoro- (trifluoro- methyl)phenyl methyl)phenyl 4- pentafluoroethyl H (trifluoromethyl) phenyl 2,4,6- 2,4,6- H tris(trifluoro- tris(trifluoro- methyl)phenyl methyl)phenyl 2,4,6- Pentafluoroethyl H tris(trifluoro- methyl)phenyl 3,5- 3,5- CN bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 2,4,6- 2,4,6- CN tris(trifluoro- tris(trifluoro- methyl)phenyl methyl)phenyl 3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoro- phenyl methyl)-phenyl 3,4- 3,4- H bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 3,4- trifluoromethyl H bis(trifluoro- methyl)-phenyl 3,4- pentafluoroethyl 3,5-bis(trifluoromethyl)- bis(trifluoro- phenyl methyl)-phenyl 3,4- pentafluoroethyl H bis(trifluoro- methyl)-phenyl 3,4- 3,4- CN bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 4-cyano-3- 3,5- H (trifluoro- bis(trifluoro methyl)-phenyl methyl)-phenyl 4-cyano-3- pentafluoroethyl H (trifluoro- methyl)-phenyl 3,5- pentafluoroethyl CN bis(trifluoro- methyl)-phenyl 4-cyano-2,6- 4-cyano-2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 4-cyano-2,6- pentafluoroethyl H bis(trifluoro- methyl)-phenyl 2,4- 2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 2,4- 2,6- CN bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 4-(3',5'- pentafluoroethyl H bis(trifluoro- methyl)phenyl)-2,6- bis(trifluoro- methyl)-phenyl phenyl phenyl CN 3,5- 3,5- CF.sub.3 bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 3,5- trifluoromethyl CF.sub.3 bis(trifluoro- methyl)-phenyl phenyl pentafluoroethyl CF.sub.3 3,5- pentafluoroethyl CF.sub.3 bis(trifluoro- methyl)-phenyl 3,4,5- 3,4,5- CF.sub.3 trifluorophenyl trifluorophenyl 4- 4-(trifluoro- CF.sub.3 (trifluoromethyl) methyl)phenyl phenyl phenyl phenyl CF.sub.3

19. (canceled)

20. The compound according to claim 19 having the general formula (I) ##STR00055## and their charge transfer complexes, their reduction products and mixtures thereof, wherein X and W independently from each other represent O or S; Y represents CR.sup.3−; represents A1 ##STR00056## wherein where # denotes the bond to the remaining molecule of formula (I), R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; R.sup.2 represents CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b; R.sup.3 represents hydrogen, CN, nitro and halogen; R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; or compounds of formula (I.a) ##STR00057## wherein the definition of R.sup.1, R.sup.2 and R.sup.3 listed in the following table: TABLE-US-00007 R.sup.1 R.sup.2 R.sup.3 methyl methyl CN methyl methyl F methyl methyl Cl methyl methyl NO.sub.2 methyl methyl pentafluorophenyl methyl methyl tetrafluoro-2-(trifluoromethyl)phenyl methyl methyl tetrafluoro-3-(trifluoromethyl)phenyl methyl methyl tetrafluoro-4-(trifluoromethyl)phenyl methyl methyl tetrafluoro-2-pyridyl methyl methyl tetrafluoro-3-pyridyl methyl methyl tetrafluoro-4-pyridyl methyl methyl tetrafluoro-2-benzonitrile methyl methyl tetrafluoro-3-benzonitrile methyl methyl tetrafluoro-4-benzonitrile trifluoromethyl trifluoromethyl CN trifluoromethyl trifluoromethyl F trifluoromethyl trifluoromethyl Cl trifluoromethyl trifluoromethyl NO.sub.2 trifluoromethyl trifluoromethyl pentafluorophenyl trifluoromethyl trifluoromethyl tetrafluoro-2-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-3-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-4-(trifluoromethyl)phenyl trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile pentafluoroethyl pentafluoroethyl H pentafluoroethyl pentafluoroethyl CN pentafluoroethyl pentafluoroethyl F pentafluoroethyl pentafluoroethyl Cl pentafluoroethyl pentafluoroethyl NO.sub.2 pentafluoroethyl pentafluoroethyl pentafluorophenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile heptafluoro-n-propyl heptafluoro-n- H propyl heptafluoro-n-propyl heptafluoro-n- CN propyl heptafluoro-n-propyl heptafluoro-n- F propyl heptafluoro-n-propyl heptafluoro-n- Cl propyl heptafluoro-n-propyl heptafluoro-n- NO.sub.2 propyl heptafluoro-n-propyl heptafluoro-n- pentafluorophenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-(trifluoromethyl)phenyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propyl heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propyl heptafluoro-isopropyl heptafluoro- H isopropyl heptafluoro-isopropyl heptafluoro- CN isopropyl heptafluoro-isopropyl heptafluoro- F isopropyl heptafluoro-isopropyl heptafluoro- Cl isopropyl heptafluoro-isopropyl heptafluoro- NO.sub.2 isopropyl heptafluor-iso-propyl heptafluoro- pentafluorophenyl isopropyl heptafluor-iso-propyl heptafluoro- tetrafluoro-2-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-(trifluoromethyl)phenyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-pyridyl isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-2-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-3-benzonitrile isopropyl heptafluoro-isopropyl heptafluoro- tetrafluoro-4-benzonitrile isopropyl tert-butyl tert-butyl CN tert-butyl tert-butyl F tert-butyl tert-butyl Cl tert-butyl tert-butyl NO.sub.2 tert-butyl tert-butyl pentafluorophenyl tert-butyl tert-butyl tetrafluoro-2-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-3-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-4-(trifluoromethyl)phenyl tert-butyl tert-butyl tetrafluoro-2-pyridyl tert-butyl tert-butyl tetrafluoro-3-pyridyl tert-butyl tert-butyl tetrafluoro-4-pyridyl tert-butyl tert-butyl tetrafluoro-2-benzonitrile tert-butyl tert-butyl tetrafluoro-3-benzonitrile tert-butyl tert-butyl tetrafluoro-4-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl H nonafluoro-n-butyl nonafluoro-n-butyl CN nonafluoro-n-butyl nonafluoro-n-butyl F nonafluoro-n-butyl nonafluoro-n-butyl Cl nonafluoro-n-butyl nonafluoro-n-butyl NO.sub.2 nonafluoro-n-butyl nonafluoro-n-butyl pentafluorophenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-(trifluoromethyl)phenyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-pyridyl nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-2-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-3-benzonitrile nonafluoro-n-butyl nonafluoro-n-butyl tetrafluoro-4-benzonitrile pentafluorophenyl pentafluorophenyl H pentafluorophenyl pentafluorophenyl CN pentafluorophenyl pentafluorophenyl F pentafluorophenyl pentafluorophenyl Cl pentafluorophenyl pentafluorophenyl NO.sub.2 pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-(trifluoromethyl)phenyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 4-pyrimidyl 4-pyrimidyl H 4-pyrimidyl 4-pyrimidyl CN 4-pyrimidyl 4-pyrimidyl F 4-pyrimidyl 4-pyrimidyl Cl 4-pyrimidyl 4-pyrimidyl NO.sub.2 4-pyrimidyl 4-pyrimidyl pentafluorophenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-benzonitrile 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-benzonitrile 2-pyrimidyl 2-pyrimidyl H 2-pyrimidyl 2-pyrimidyl CN 2-pyrimidyl 2-pyrimidyl F 2-pyrimidyl 2-pyrimidyl Cl 2-pyrimidyl 2-pyrimidyl NO.sub.2 2-pyrimidyl 2-pyrimidyl pentafluorophenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-(trifluoromethyl)phenyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 3,5- 3,5- H bis(trifluoromethyl)- bisftrifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl H bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl H furan-2-yl pentafluoroethyl H 3,5- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3′,5′- pentafluoroethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 3′,5′- trifluoromethyl H bis(trifluoromethyl)- [1,1′-biphenyl]-4-yl 4-fluoro-3- pentafluoroethyl H trifluoromethyl-phenyl 4-fluoro-3- 3,5- H trifluoromethyl-phenyl bisftrifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl H 3,4,5-trifluorophenyl pentafluoroethyl H 4- 4- H (trifluoromethyl)phenyl (trifluoromethyl)phenyl 4- pentafluoroethyl H (trifluoromethyl)phenyl 2,4,6- 2,4,6- H tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 2,4,6- Pentafluoroethyl H tris(trifluoromethyl)phenyl 3,5- 3,5- CN bis(trifluoromethyl)- bisftrifluoromethyl)- phenyl phenyl 2,4,6- 2,4,6- CN tris(trifluoromethyl)phenyl tris(trifluoromethyl)phenyl 3,5- pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)- phenyl 3,4- 3,4- H bis(trifluoromethyl)- bisftrifluoromethyl)- phenyl phenyl 3,4- trifluoromethyl H bis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl 3,5-bis(trifluoromethyl)-phenyl bis(trifluoromethyl)- phenyl 3,4- pentafluoroethyl H bis(trifluoromethyl)- phenyl 3,4- 3,4- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- 3,5- H (trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-3- pentafluoroethyl H (trifluoromethyl)- phenyl 3,5- pentafluoroethyl CN bis(trifluoromethyl)- phenyl 4-cyano-2,6- 4-cyano-2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-cyano-2,6- pentafluoroethyl H bis(trifluoromethyl)- phenyl 2,4- 2,6- H bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 2,4- 2,6- CN bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 4-(3′,5′- pentafluoroethyl H bis(trifluoro- methyl)phenyl)-2,6- bis(trifluoromethyl)- phenyl phenyl phenyl CN 3,5- 3,5- CF.sub.3 bis(trifluoromethyl)- bis(trifluoromethyl)- phenyl phenyl 3,5- trifluoromethyl CF.sub.3 bis(trifluoromethyl)- phenyl phenyl pentafluoroethyl CF.sub.3 3,5- pentafluoroethyl CF.sub.3 bis(trifluoromethyl)- phenyl 3,4,5-trifluorophenyl 3,4,5-trifluorophenyl CF.sub.3 4- 4-(trifluoro- CF.sub.3 (trifluoromethyl)phenyl methyl)phenyl phenyl phenyl CF.sub.3

Description

DESCRIPTION OF THE INVENTION

[0086] The invention has the following advantages: [0087] The cerium-(IV)-complexes according to the invention have only low production costs. [0088] The cerium-(IV)-complexes according to the invention are advantageously suitable as electron acceptors for use as p-dopants and as electron transport materials in organic-electronic components. [0089] The cerium-(IV)-complexes according to the invention exhibit better conductivity compared to known electron acceptors. [0090] The cerium-(IV)-complexes according to the invention show an improved thermostability of the doped layers compared to the state of the art. [0091] Furthermore, the cerium (IV) complexes according to the invention are characterized by a higher doping efficiency. [0092] The cerium-(IV)-complexes according to the invention show only a low absorption of the doped layer. Therefore, parasitic absorption and emissions can be reduced or even prevented. [0093] The cerium-(IV)-complexes according to the invention are suitable for the production of organic and hybrid opto-electronic components, both by means of solvent processing and by vacuum reprocessing.

[0094] In the context of the invention, a bidentate ligand (also called didentate) is a ligand, which binds with two atoms to the metal atom (cerium atom).

[0095] In the context of the invention, a homoleptic cerium (IV) compound is a complex, wherein all ligands are identical.

[0096] In the context of the invention, a heteroleptic cerium (IV) compound is a complex, wherein the meaning of at least one ligand is different to the remaining ligands.

[0097] In the context of the invention, the prefix C.sub.n-C.sub.m indicates the number of carbon atoms that a molecule or residue designated thereby may contain.

[0098] In the context of the invention, the expression C.sub.1-C.sub.6-alkyl refers to unbranched or branched saturated hydrocarbon groups having 1 to 6 carbon atoms. C.sub.1-C.sub.6-alkyl are e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methyl propyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl. C.sub.1-C.sub.4-alkyl refers, e.g. to methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

[0099] In the context of the invention the expression C.sub.1-C.sub.6-alkoxy refers to an unbranched or branched saturated C.sub.1-C.sub.6-alkyl group as defined above, which is bound via an oxygen atom. Alkoxy radicals with 1 to 4 carbon atoms are preferred, particularly preferred are 1 or 2 carbon atoms. C.sub.1-C.sub.2-alkoxy is methoxy or ethoxy. C.sub.1-C.sub.4-alkoxy is e.g. methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C.sub.1-C.sub.6-alkoxy comprises the meanings given for C.sub.1-C.sub.4-alkoxy and additionally e.g. pentoxy, 1 methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy and 3,3-dimethylbutoxy.

[0100] In the context of the invention the expression C.sub.1-C.sub.6-alkylsulfanyl refers to an unbranched or branched saturated C.sub.1-C.sub.6-alkyl group as defined above, which is bound via a sulfur atom. Alkylsulfanyl radicals with 1 to 4 carbon atoms are preferred, particularly preferred are 1 or 2 carbon atoms. C.sub.1-C.sub.2-alkylsulfanyl is methylsulfanyl or ethylsulfanyl. C.sub.1-C.sub.4-alkylsulfanyl is e.g. methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, 1-methylethyl-sulfanyl (isopropylsulfanyl), butylsulfanyl, 1-methylpropylsulfonyl (sec-butylsulfanyl), 2-methylpropylsulfonyl (isobutylsulfanyl) or 1,1-dimethylethylsulfanyl (tert-butylsulfanyl). C.sub.1-C.sub.6-alkylthio comprises the meanings given for C.sub.1-C.sub.4-alkylsulfanyl and additionally also, e.g., pentylsulfanyl, 1-methylbutylsulfanyl, 2-methylbutylsulfanyl, 3-methylbutylsulfanyl, 1,1-dimethylpropylsulfanyl, 1,2-dimethylpropylsulfanyl, 2,2-dimethylpropylsulfanyl, 1-ethylpropylsulfanyl, hexylsulfanyl, 1-methylpentylsulfanyl, 2-methylpentylsulfanyl, 3-methylpentylsulfanyl, 4-methylpentylsulfanyl, 1,1-dimethylbutylsulfanyl, 1,2-dimethylbutylsulfanyl, 1,3-dimethylbutylsulfanyl, 2,2-dimethylbutylsulfanyl, 2,3-dimethylbutylsulfanyl, 3,3-dimethylbutylsulfanyl, 1-ethylbutylsulfanyl, 2-ethylbutylsulfanyl, 1,1,2-trimethylpropylsulfanyl, 1,2,2-trimethylpropylsulfanyl, 1-ethyl-1-methylpropylsulfanyl or 1-ethyl-2-methylpropylsulfanyl.

[0101] In the context of the invention the expressions haloalkyl, haloalkoxy and haloalkylsulfanyl refer to partially or fully halogenated alkyl, alkoxy or alkylsulfanyl. In other words, one or more hydrogen atoms, for example 1, 2, 3, 4 or 5 hydrogen atoms bonded to one or more carbon atoms of alkyl, alkoxy or alkylsulfanyl are replaced by a halogen atom, in particular by fluorine or chlorine.

[0102] The expression “halogen” denotes in each case fluorine, chlorine, bromine or iodine.

[0103] The expression “CN” denotes the cyano group (—C≡N).

[0104] The expression “aryl” comprises in the context of the invention mono- or polynuclear aromatic hydrocarbon radicals with usually 6 to 14, especially preferably 6 to 10 carbon atoms. Examples of aryl are especially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, etc. and especially phenyl or naphthyl.

[0105] The expression “hetaryl” comprises in the context of the invention mono- or polynuclear aromatic hydrocarbon radicals with 4 to 13 carbon atoms, wherein 1, 2 or 3 carbon atoms have been replaced by 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, said heteroatoms and heteroatom-containing groups, selected from N, O, S, SO and SO.sub.2. The hetaryl group may be attached to the remainder of the molecule via a ring carbon or via a ring nitrogen. Examples of 5- or 6-membered aromatic heterocyclic rings (also called heteroaromatic rings or hetaryl) are 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl. Examples of 8-, 9- or 10-membered aromatic heterobicyclic rings are hetaryl having one of the aforementioned 5- or 6-membered heteroaromatic rings and another aromatic carbocycle or 5- or 6-membered heterocycle fused thereto, for example a fused benzene, thiophen-, furan-, pyrrol-, pyrazol-, imidazol-, pyridin- or pyrimidin-ring. These bicyclic hetarylenes comprises e.g. quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, in particular 2-benzofuryl, benzothienyl, in particular 2-benzothienyl, benzo[b]thiazolyl, in particular 2-benzo[b]thiazolyl, benzoxazolyl, in particular 2-benzoxazolyl, benzothiazolyl, in particular 2-benzothiazolyl, benzimidazolyl, in particular 2-benzimidazolyl, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5yl, imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridin-2-yl.

[0106] When # appears in a formula, showing a preferred substructure of a compound of the present invention, it denotes the bond to the rest of the molecule.

[0107] Cerium Compounds of the Formulae (I.1) and (I)

[0108] The compound of formula (I.1)

Ce.sup.4+(L.sub.1L.sub.2L.sub.3L.sub.4).sup.4−(I.1), wherein

[0109] L.sub.1; L.sub.2; L.sub.3; and L.sub.4 are defined above and below, encompasses compounds, wherein [0110] all four ligands L.sub.1, L.sub.2, L.sub.3 and L.sub.4 have the same meanings, [0111] three of the four ligands have the same meanings, [0112] two of the four ligands have the same meanings, [0113] all four ligands L.sub.1, L.sub.2, L.sub.3 and L.sub.4 have different meaning.

[0114] Preferred are compounds of formula (I.1) wherein L.sub.1, L.sub.2, L.sub.3 and L.sub.4 have the same meanings.

[0115] In the cerium compounds of formula (I.1) L.sub.1, L.sub.2, L.sub.3 and L.sub.4 are independently from each other selected from bidentate ligands having the general formula (I.2). In the following preferred embodiments of the compounds (I.1) are directly defined by preferred embodiments of their bidentate ligands (I.2).

[0116] Preferred are compounds of formula (I) and ligands of formula (I.2), wherein R.sup.1 and R.sup.2 are independently selected from CN, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b and the group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17 A18 and A19

##STR00015## ##STR00016##

where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), [0117] R.sup.A, R.sup.B, R.sup.c, R.sup.D and R.sup.E are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; [0118] R.sup.4a, R.sup.4b independently represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0119] R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; and [0120] R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5.

[0121] Another preferred embodiment are compounds of formula (I) and ligands of formula (I.2), wherein R.sup.1 and R.sup.2 are independently selected from CN, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b and the group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 and A15, where [0122] R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; [0123] R.sup.4a, R.sup.4b independently represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0124] R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; and [0125] R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5.

[0126] Irrespective of their occurrence the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are preferably selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-haloalkyl.

[0127] Particularly preferred, the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently from each other selected from hydrogen, CN, fluorine and chlorine.

[0128] In another particular embodiment the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently from each other selected from hydrogen, CN, fluorine, chlorine and phenyl, which is substituted by 1 or 2 identical or different radicals selected from C.sub.1-C.sub.2-haloalkyl.

[0129] Especially preferred, the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E all represent fluorine.

[0130] Also especially preferred the radicals R.sup.A, R.sup.B, R.sup.D and R.sup.E are hydrogen and R.sup.C is 3,5-di(trifluoromethyl)phenyl.

[0131] Preferably in formula (I) and ligands of formula (I.2), R.sup.1 and R.sup.2 are independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, A1 and A5

##STR00017##

[0132] where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), and wherein

[0133] R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-haloalkyl.

[0134] In another preferred embodiment in formula (I) and ligands of formula (I.2) R.sup.1 and R.sup.2 are independently selected from A16 and A17

##STR00018##

[0135] where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), and wherein

[0136] R.sup.A, R.sup.B and R.sup.C are independently selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl and C.sub.1-C.sub.4-chloroalkyl. Preferably R.sup.A, R.sup.B and R.sup.C are all hydrogen.

[0137] In a preferred embodiment, in formula (I) and ligands of formula (I.2), R.sup.1 and R.sup.2 are independently selected from A1 and A5

##STR00019##

[0138] where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), and wherein

[0139] R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-haloalkyl.

[0140] In a particularly preferred embodiment in formula (I) and ligands of formula (I.2) R.sup.1 and R.sup.2 are independently selected from A1 and A5, wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from CN, fluorine and chlorine.

[0141] In another particularly preferred embodiment in formula (I) R.sup.1 and R.sup.2 are independently selected from A1 and A5, wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from CN, fluorine and chlorine.

[0142] In another preferred embodiment in formula (I) and ligands of formula (I.2), R.sup.1 and R.sup.2 are independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and A1, wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are independently selected from CN, fluorine and chlorine.

[0143] In another preferred embodiment, in formula (I), R.sup.1 and R.sup.2 are independently selected from C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl, C.sub.1-C.sub.4-chloroalkyl and A1, wherein R.sup.A, R.sup.B, R.sup.c, R.sup.D and R.sup.E are independently selected from CN, fluorine and chlorine.

[0144] In a particular embodiment, in formula (I) and ligands of formula (I.2), Wand R.sup.2 are independently selected from A1 and A5, wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are fluorine.

[0145] In a particular embodiment, in formula (I), R.sup.1 and R.sup.2 are independently selected from A1 and A5, wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are fluorine.

[0146] In another preferred embodiment in formula (I) and ligands of formula (I.2), R.sup.1 and R.sup.2 are′A1, wherein R.sup.A, R.sup.B, R.sup.D and R.sup.E are hydrogen and R.sup.C is 3,5-di(trifluoromethyl)phenyl.

[0147] In another preferred embodiment, in formula (I), R.sup.1 and R.sup.2 are A1, wherein R.sup.A, R.sup.B, R.sup.D and R.sup.E are hydrogen and R.sup.C is 3,5-di(trifluoromethyl)phenyl.

[0148] Preferred are compounds of formula (I) and ligands of formula (I.2), wherein Y represents the radical CR.sup.3 and R.sup.3 is selected from hydrogen, CN, nitro, halogen, CF.sub.3 and the group B consisting B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 and B15

##STR00020## ##STR00021##

where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2),

[0149] R.sup.F, R.sup.G, R.sup.H, R.sup.I and R.sup.J are independently selected from hydrogen, CN, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; and

[0150] R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5.

[0151] Irrespective of their occurrence the radicals R.sup.F, R.sup.G, R.sup.H, R.sup.I and R.sup.J are preferably selected from hydrogen, CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-fluoroalkyl and C.sub.1-C.sub.4-chloroalkyl.

[0152] In a preferred embodiment the radicals R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E represent independently CN, fluorine or chlorine.

[0153] In formula (I) and ligands of formula (I.2), Y preferably represents a radical CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro, halogen CF.sub.3 and B1

##STR00022##

[0154] where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), and wherein

[0155] R.sup.F, R.sup.G, R.sup.H, R.sup.I and R.sup.J are independently selected from hydrogen, CN, fluorine and chlorine.

[0156] In formula (I) and ligands of formula (I.2), Y preferably represents a radical CR.sup.3, wherein R.sup.3 represents B1

##STR00023##

[0157] where # denotes the bond to the remaining molecule of formula (I) and ligands of formula (I.2), and wherein

[0158] R.sup.E, R.sup.G, R.sup.H, R.sup.I and R.sup.J are independently selected from CN, fluorine and chlorine.

[0159] In another preferred embodiment, Y represents a radical CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro, fluorine, chlorine and CF.sub.3.

[0160] Irrespective of their occurrence, the radicals R.sup.4a und R.sup.4b are preferably selected from hydrogen and C.sub.1-C.sub.4-alkyl.

[0161] Irrespective of its occurrence, the radical R.sup.5 is preferably selected from CN, fluorine, chlorine, C.sub.1-C.sub.4-alkyl und C.sub.1-C.sub.4-haloalkyl.

[0162] Irrespective of its occurrence, the radical R.sup.6 is preferably selected from hydrogen and C.sub.1-C.sub.4-alkyl.

[0163] Irrespective of its occurrence, the radical R′ is preferably selected from hydrogen and C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

[0164] In a preferred first embodiment A, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0165] X and W represent S or O, in particular O; [0166] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0167] R.sup.1 and R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0168] Particular preferred are compounds of formula (I), wherein [0169] X and W represent S or O, in particular O; [0170] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0171] R.sup.1 and R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0172] In a preferred second embodiment B, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0173] X and W represent S or O, in particular O; [0174] Y represents CR.sup.3, wherein R.sup.3 represents B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular represents B1; [0175] R.sup.1 and R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represent C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0176] Particular preferred are compounds of formula (I), wherein [0177] X and W represent S or O, in particular O; [0178] Y represents CR.sup.3, wherein R.sup.3 represents B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular represents B1; [0179] R.sup.1 and R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represent C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0180] In a preferred third embodiment C, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0181] X and W represent S or O, in particular O; [0182] Y represents CR.sup.3, wherein R.sup.3 represents B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular represents B1; [0183] R.sup.1 and R.sup.2 independently from each other represent A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in particular represent A1 or A5.

[0184] Particular preferred are compounds of formula (I), wherein [0185] X and W represent S or O, in particular O; [0186] Y represents CR.sup.3, wherein R.sup.3 represents B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 or B15, in particular represents B1; [0187] R.sup.1 and R.sup.2 independently from each other represent A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in particular represent A1 or A5.

[0188] In a preferred fourth embodiment D, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0189] X and W represent S or O, in particular O; [0190] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0191] R.sup.1 and R.sup.2 independently from each other represent A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in particular represent A1 or A5.

[0192] Particular preferred are compounds of formula (I), wherein [0193] X and W represent S or O, in particular O; [0194] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0195] R.sup.1 and R.sup.2 independently from each other represent A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14 or A15, in particular represent A1 or A5.

[0196] In a preferred fifth embodiment E, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0197] X and W represent S or O, in particular O; [0198] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0199] R.sup.1 represents A1; [0200] R.sup.2 represents CN, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0201] Particular preferred are compounds of formula (I), wherein [0202] X and W represent S or O, in particular O; [0203] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in particular fluorine, CN and nitro; [0204] R.sup.1 represents A1; [0205] R.sup.2 represents CN, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0206] In a preferred sixth embodiment F, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0207] X and W represent S or O, in particular O; [0208] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in hydrogen; [0209] R.sup.1 and R.sup.2 independently from each other represent A16 or A17.

[0210] Particular preferred are compounds of formula (I), wherein [0211] X and W represent S or O, in particular O; [0212] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in hydrogen; [0213] R.sup.1 and R.sup.2 independently from each other represent A16 or A17.

[0214] In a preferred seventh embodiment G, compounds of formula (I) and ligands of formula (I.2) are preferred, wherein [0215] X and W represent S or O, in particular O; [0216] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in hydrogen; [0217] R.sup.1 represents A16 or A17; [0218] R.sup.2 represents CN, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0219] Particular preferred are compounds of formula (I), wherein [0220] X and W represent S or O, in particular O; [0221] Y represents CR.sup.3, wherein R.sup.3 is selected from hydrogen, CN, nitro and halogen, in hydrogen; [0222] R.sup.1 represents A16 or A17; [0223] R.sup.2 represents CN, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.5-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, in particular represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

[0224] Particular preferred are compounds of formula (I.a′) [0225] Ce.sup.4+[(R.sup.1—C(—O)═C(R.sup.3)—C(═O)—R.sup.2)(R.sup.1′—C(═O))═C(R.sup.3)—C(═O)—R.sup.2)(R.sup.1″-C(—O)═C(R.sup.3″)—C(═O)—R.sup.2″) (R.sup.1″ —C(—O)═C(R.sup.3″)—C(═O)—R.sup.2″)].sup.4−(I.a′, wherein [0226] (R.sup.1, R.sup.2, R.sup.3), (R.sup.1′, R.sup.2′, R.sup.3′), (R.sup.1″, R.sup.2, R.sup.3″) and (R.sup.1″′, R.sup.2″′, R.sup.3″′) are each selected from the definition given in one line of the following table 1

TABLE-US-00001 TABLE 1 R.sup.1, R.sup.1′, R.sup.1′′, R.sup.1′′′ R.sup.2, R.sup.2′, R.sup.2′′, R.sup.2′′′ R.sup.3, R.sup.3′, R.sup.3′′, R.sup.3′′′ 1. methyl methyl H 2. methyl methyl CN 3. methyl methyl F 4. methyl methyl Cl 5. methyl methyl NO.sub.2 6. methyl methyl pentafluorophenyl 7. methyl methyl tetrafluoro-2- (trifluoromethyl)phenyl 8. methyl methyl tetrafluoro-3- (trifluoromethyl)phenyl 9. methyl methyl tetrafluoro-4- (trifluoromethyl)phenyl 10. methyl methyl tetrafluoro-2-pyridyl 11. methyl methyl tetrafluoro-3-pyridyl 12. methyl methyl tetrafluoro-4-pyridyl 13. methyl methyl tetrafluoro-2-benzonitrile 14. methyl methyl tetrafluoro-3-benzonitrile 15. methyl methyl tetrafluoro-4-benzonitrile 16. trifluoromethyl trifluoromethyl H 17. trifluoromethyl trifluoromethyl CN 18. trifluoromethyl trifluoromethyl F 19. trifluoromethyl trifluoromethyl Cl 20. trifluoromethyl trifluoromethyl NO.sub.2 21. trifluoromethyl trifluoromethyl pentafluorophenyl 22. trifluoromethyl trifluoromethyl tetrafluoro-2- (trifluoromethyl)phenyl 23. trifluoromethyl trifluoromethyl tetrafluoro-3- (trifluoromethyl)phenyl 24. trifluoromethyl trifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl 25. trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl 26. trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl 27. trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl 28. trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile 29. trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile 30. trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile 31. pentafluoroethyl pentafluoroethyl H 32. pentafluoroethyl pentafluoroethyl CN 33. pentafluoroethyl pentafluoroethyl F 34. pentafluoroethyl pentafluoroethyl Cl 35. pentafluoroethyl pentafluoroethyl NO.sub.2 36. pentafluoroethyl pentafluoroethyl pentafluorophenyl 37. pentafluoroethyl pentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl 38. pentafluoroethyl pentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl 39. pentafluoroethyl pentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl 40. pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl 41. pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl 42. pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl 43. pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile 44. pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile 45. pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile 46. heptafluoro-n- heptafluoro-n- H propyl propyl 47. heptafluoro-n- heptafluoro-n- CN propyl propyl 48. heptafluoro-n- heptafluoro-n- F propyl propyl 49. heptafluoro-n- heptafluoro-n- Cl propyl propyl 50. heptafluoro-n- heptafluoro-n- NO.sub.2 propyl propyl 51. heptafluoro-n- heptafluoro-n- pentafluorophenyl propyl propyl 52. heptafluoro-n- heptafluoro-n- tetrafluoro-2- propyl propyl (trifluoromethyl)phenyl 53. heptafluoro-n- heptafluoro-n- tetrafluoro-3- propyl propyl (trifluoromethyl)phenyl 54. heptafluoro-n- heptafluoro-n- tetrafluoro-4- propyl propyl (trifluoromethyl)phenyl 55. heptafluoro-n- heptafluoro-n- tetrafluoro-2-pyridyl propyl propyl 56. heptafluoro-n- heptafluoro-n- tetrafluoro-3-pyridyl propyl propyl 57. heptafluoro-n- heptafluoro-n- tetrafluoro-4-pyridyl propyl propyl 58. heptafluoro-n- heptafluoro-n- tetrafluoro-2-benzonitrile propyl propyl 59. heptafluoro-n- heptafluoro-n- tetrafluoro-3-benzonitrile propyl propyl 60. heptafluoro-n- heptafluoro-n- tetrafluoro-4-benzonitrile propyl propyl 61. heptafluoro- heptafluoro- H isopropyl isopropyl 62. heptafluoro- heptafluoro- CN isopropyl isopropyl 63. heptafluoro- heptafluoro- F isopropyl isopropyl 64. heptafluoro- heptafluoro- Cl isopropyl isopropyl 65. heptafluoro- heptafluoro- NO.sub.2 isopropyl isopropyl 66. heptafluor- heptafluoro- pentafluorophenyl isopropyl isopropyl 67. heptafluor- heptafluoro- tetrafluoro-2- isopropyl isopropyl (trifluoromethyl)phenyl 68. heptafluoro- heptafluoro- tetrafluoro-3- isopropyl isopropyl (trifluoromethyl)phenyl 69. heptafluoro- heptafluoro- tetrafluoro-4- isopropyl isopropyl (trifluoromethyl)phenyl 70. heptafluoro- heptafluoro- tetrafluoro-2-pyridyl isopropyl isopropyl 71. heptafluoro- heptafluoro- tetrafluoro-3-pyridyl isopropyl isopropyl 72. heptafluoro- heptafluoro- tetrafluoro-4-pyridyl isopropyl isopropyl 73. heptafluoro- heptafluoro- tetrafluoro-2-benzonitrile isopropyl isopropyl 74. heptafluoro- heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropyl 75. heptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropyl isopropyl 76. tert-butyl tert-butyl H 77. tert-butyl tert-butyl CN 78. tert-butyl tert-butyl F 79. tert-butyl tert-butyl Cl 80. tert-butyl tert-butyl NO.sub.2 81. tert-butyl tert-butyl pentafluorophenyl 82. tert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl 83. tert-butyl tert-butyl tetrafluoro-3- (trifluoromethyl)phenyl 84. tert-butyl tert-butyl tetrafluoro-4- (trifluoromethyl)phenyl 85. tert-butyl tert-butyl tetrafluoro-2-pyridyl 86. tert-butyl tert-butyl tetrafluoro-3-pyridyl 87. tert-butyl tert-butyl tetrafluoro-4-pyridyl 88. tert-butyl tert-butyl tetrafluoro-2-benzonitrile 89. tert-butyl tert-butyl tetrafluoro-3-benzonitrile 90. tert-butyl tert-butyl tetrafluoro-4-benzonitrile 91. nonafluoro-n- nonafluoro-n- H butyl butyl 92. nonafluoro-n- nonafluoro-n- CN butyl butyl 93. nonafluoro-n- nonafluoro-n- F butyl butyl 94. nonafluoro-n- nonafluoro-n- Cl butyl butyl 95. nonafluoro-n- nonafluoro-n- NO.sub.2 butyl butyl 96. nonafluoro-n- nonafluoro-n- pentafluorophenyl butyl butyl 97. nonafluoro-n- nonafluoro-n- tetrafluoro-2- butyl butyl (trifluoromethyl)phenyl 98. nonafluoro-n- nonafluoro-n- tetrafluoro-3- butyl butyl (trifluoromethyl)phenyl 99. nonafluoro-n- nonafluoro-n- tetrafluoro-4- butyl butyl (trifluoromethyl)phenyl 100. nonafluoro-n- nonafluoro-n- tetrafluoro-2-pyridyl butyl butyl 101. nonafluoro-n- nonafluoro-n- tetrafluoro-3-pyridyl butyl butyl 102. nonafluoro-n- nonafluoro-n- tetrafluoro-4-pyridyl butyl butyl 103. nonafluoro-n- nonafluoro-n- tetrafluoro-2-benzonitrile butyl butyl 104. nonafluoro-n- nonafluoro-n- tetrafluoro-3-benzonitrile butyl butyl 105. nonafluoro-n- nonafluoro-n- tetrafluoro-4-benzonitrile butyl butyl 106. pentafluorophenyl pentafluorophenyl H 107. pentafluorophenyl pentafluorophenyl CN 108. pentafluorophenyl pentafluorophenyl F 109. pentafluorophenyl pentafluorophenyl Cl 110. pentafluorophenyl pentafluorophenyl NO.sub.2 111. pentafluorophenyl pentafluorophenyl pentafluorophenyl 112. pentafluorophenyl pentafluorophenyl tetrafluoro-2- (trifluoromethyl)phenyl 113. pentafluorophenyl pentafluorophenyl tetrafluoro-3- (trifluoromethyl)phenyl 114. pentafluorophenyl pentafluorophenyl tetrafluoro-4- (trifluoromethyl)phenyl 115. pentafluorophenyl pentafluorophenyl tetrafluoro-2-pyridyl 116. pentafluorophenyl pentafluorophenyl tetrafluoro-3-pyridyl 117. pentafluorophenyl pentafluorophenyl tetrafluoro-4-pyridyl 118. pentafluorophenyl pentafluorophenyl tetrafluoro-2-benzonitrile 119. pentafluorophenyl pentafluorophenyl tetrafluoro-3-benzonitrile 120. pentafluorophenyl pentafluorophenyl tetrafluoro-4-benzonitrile 121. 4-pyrimidyl 4-pyrimidyl H 122. 4-pyrimidyl 4-pyrimidyl CN 123. 4-pyrimidyl 4-pyrimidyl F 124. 4-pyrimidyl 4-pyrimidyl Cl 125. 4-pyrimidyl 4-pyrimidyl NO.sub.2 126. 4-pyrimidyl 4-pyrimidyl pentafluorophenyl 127. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 128. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 129. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 130. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-pyridyl 131. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl 132. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 133. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-benzonitrile 134. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-benzonitrile 135. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-benzonitrile 136. 2-pyrimidyl 2-pyrimidyl H 137. 2-pyrimidyl 2-pyrimidyl CN 138. 2-pyrimidyl 2-pyrimidyl F 139. 2-pyrimidyl 2-pyrimidyl Cl 140. 2-pyrimidyl 2-pyrimidyl NO.sub.2 141. 2-pyrimidyl 2-pyrimidyl pentafluorophenyl 142. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 143. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 144. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 145. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 146. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 147. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 148. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 149. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 150. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 151. 3,5-bis(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 152. 3,5-bis(trifiuoro- trifluoromethyl H methyl)-phenyl 153. phenyl pentafluoroethyl H 154. furan-2-yl trifluoromethyl H 155. furan-2-yl pentafluoroethyl H 156. 3,5-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 157. 3′,5′-bis(trifluoro- pentafluoroethyl H methyl)-[1,1′- biphenyl]-4-yl 158. 3′,5′-bis(trifluoro- trifluoromethyl H methyl)-[1,1′- biphenyl]-4-yl 159. 4-fluoro-3- pentafluoroethyl H trifluoromethyl- phenyl 160. 4-fluoro-3- 3,5-bis(trifluoro- H trifluoromethyl- methyl)-phenyl phenyl 161. 3,4,5-trifluoro- 3,4,5-trifluoro- H phenyl phenyl 162. 3,4,5-trifluoro- pentafluoroethyl H phenyl 163. 4-(trifluoro- 4-(trifluoro- H methyl)phenyl methyl)phenyl 164. 4-(trifluoro- pentafluoroethyl H methyl)phenyl 165. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- H methyl)phenyl methyl)phenyl 166. 2,4,6-tris(trifluoro- Pentafluoroethyl H methyl)phenyl 167. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 168. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- CN methyl)phenyl methyl)phenyl 169. 3,5-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 170. 3,4-bis(trifluoro- 3,4-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 171. 3,4-bis(trifluoro- trifluoromethyl H methyl)-phenyl 172. 3,4-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 173. 3,4-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 174. 3,4-bis(trifluoro- 3,4-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 175. 4-cyano-3-(tri- 3,5-bis(trifluoro- H fluoromethyl)- methyl)-phenyl phenyl 176. 4-cyano-3-(tri- pentafluoroethyl H fluoromethyl)- phenyl 177. 3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 178. 4-cyano-2,6- 4-cyano-2,6- H bis(trifluoro- bis(trifluoro- methyl)-phenyl methyl)-phenyl 179. 4-cyano-2,6- pentafluoroethyl H bis(trifluoro- methyl)-phenyl 180. 2,4-bis(trifluoro- 2,6-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 181. 2,4-bis(trifluoro- 2,6-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 182. 4-(3′,5′-bis pentafluoroethyl H (trifluoromethyl) phenyl)-2,6- bis(trifluoro- methyl)-phenyl 183. phenyl phenyl CN 184. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CF.sub.3 methyl)-phenyl methyl)-phenyl 185. 3,5-bis(trifluoro- trifluoromethyl CF3 methyl)-phenyl 186. phenyl pentafluoroethyl CF.sub.3 187. 3,5-bis(trifluoro- pentafluoroethyl CF.sub.3 methyl)-phenyl 188. 3,4,5-trifluoro- 3,4,5-trifluoro- CF.sub.3 phenyl phenyl 189. 4-(trifluoro- 4-(trifluoro- CF.sub.3 methyl)phenyl methyl)phenyl 190. phenyl phenyl CF.sub.3

[0227] Particularly preferred are the compounds of formula (I.a)

##STR00024##

[0228] wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in table 2:

TABLE-US-00002 TABLE 2 R.sup.1 R.sup.2 R.sup.3 1. methyl methyl H 2. methyl methyl CN 3. methyl methyl F 4. methyl methyl Cl 5. methyl methyl NO.sub.2 6. methyl methyl pentafluorophenyl 7. methyl methyl tetrafluoro-2- (trifluoromethyl)phenyl 8. methyl methyl tetrafluoro-3- (trifluoromethyl)phenyl 9. methyl methyl tetrafluoro-4- (trifluoromethyl)phenyl 10. methyl methyl tetrafluoro-2-pyridyl 11. methyl methyl tetrafluoro-3-pyridyl 12. methyl methyl tetrafluoro-4-pyridyl 13. methyl methyl tetrafluoro-2-benzonitrile 14. methyl methyl tetrafluoro-3-benzonitrile 15. methyl methyl tetrafluoro-4-benzonitrile 16. trifluoromethyl trifluoromethyl H 17. trifluoromethyl trifluoromethyl CN 18. trifluoromethyl trifluoromethyl F 19. trifluoromethyl trifluoromethyl Cl 20. trifluoromethyl trifluoromethyl NO.sub.2 21. trifluoromethyl trifluoromethyl pentafluorophenyl 22. trifluoromethyl trifluoromethyl tetrafluoro-2- (trifluoromethyl)phenyl 23. trifluoromethyl trifluoromethyl tetrafluoro-3- (trifluoromethyl)phenyl 24. trifluoromethyl trifluoromethyl tetrafluoro-4- (trifluoromethyl)phenyl 25. trifluoromethyl trifluoromethyl tetrafluoro-2-pyridyl 26. trifluoromethyl trifluoromethyl tetrafluoro-3-pyridyl 27. trifluoromethyl trifluoromethyl tetrafluoro-4-pyridyl 28. trifluoromethyl trifluoromethyl tetrafluoro-2-benzonitrile 29. trifluoromethyl trifluoromethyl tetrafluoro-3-benzonitrile 30. trifluoromethyl trifluoromethyl tetrafluoro-4-benzonitrile 31. pentafluoroethyl pentafluoroethyl H 32. pentafluoroethyl pentafluoroethyl CN 33. pentafluoroethyl pentafluoroethyl F 34. pentafluoroethyl pentafluoroethyl Cl 35. pentafluoroethyl pentafluoroethyl NO.sub.2 36. pentafluoroethyl pentafluoroethyl pentafluorophenyl 37. pentafluoroethyl pentafluoroethyl tetrafluoro-2- (trifluoromethyl)phenyl 38. pentafluoroethyl pentafluoroethyl tetrafluoro-3- (trifluoromethyl)phenyl 39. pentafluoroethyl pentafluoroethyl tetrafluoro-4- (trifluoromethyl)phenyl 40. pentafluoroethyl pentafluoroethyl tetrafluoro-2-pyridyl 41. pentafluoroethyl pentafluoroethyl tetrafluoro-3-pyridyl 42. pentafluoroethyl pentafluoroethyl tetrafluoro-4-pyridyl 43. pentafluoroethyl pentafluoroethyl tetrafluoro-2-benzonitrile 44. pentafluoroethyl pentafluoroethyl tetrafluoro-3-benzonitrile 45. pentafluoroethyl pentafluoroethyl tetrafluoro-4-benzonitrile 46. heptafluoro-n-propyl heptafluoro-n- H propyl 47. heptafluoro-n-propyl heptafluoro-n- CN propyl 48. heptafluoro-n-propyl heptafluoro-n- F propyl 49. heptafluoro-n-propyl heptafluoro-n- Cl propyl 50. heptafluoro-n-propyl heptafluoro-n- NO.sub.2 propyl 51. heptafluoro-n-propyl heptafluoro-n- pentafluorophenyl propyl 52. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2- propyl (trifluoromethyl)phenyl 53. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3- propyl (trifluoromethyl)phenyl 54. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4- propyl (trifluoromethyl)phenyl 55. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-pyridyl propyl 56. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-pyridyl propyl 57. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-pyridyl propyl 58. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-2-benzonitrile propyl 59. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-3-benzonitrile propyl 60. heptafluoro-n-propyl heptafluoro-n- tetrafluoro-4-benzonitrile propyl 61. heptafluoro- heptafluoro- H isopropyl isopropyl 62. heptafluoro- heptafluoro- CN isopropyl isopropyl 63. heptafluoro- heptafluoro- F isopropyl isopropyl 64. heptafluoro- heptafluoro- Cl isopropyl isopropyl 65. heptafluoro- heptafluoro- NO.sub.2 isopropyl isopropyl 66. heptafluoro- heptafluoro- pentafluorophenyl isopropyl isopropyl 67. heptafluoro- heptafluoro- tetrafluoro-2- isopropyl isopropyl (trifluoromethyl)phenyl 68. heptafluoro- heptafluoro- tetrafluoro-3- isopropyl isopropyl (trifluoromethyl)phenyl 69. heptafluoro- heptafluoro- tetrafluoro-4- isopropyl isopropyl (trifluormethyl)phenyl 70. heptafluoro- heptafluoro- tetrafluoro-2-pyridyl isopropyl isopropyl 71. heptafluoro- heptafluoro- tetrafluoro-3-pyridyl isopropyl isopropyl 72. heptafluoro- heptafluoro- tetrafluoro-4-pyridyl isopropyl isopropyl 73. heptafluoro- heptafluoro- tetrafluoro-2-benzonitrile isopropyl isopropyl 74. heptafluoro- heptafluoro- tetrafluoro-3-benzonitrile isopropyl isopropyl 75. heptafluoro- heptafluoro- tetrafluoro-4-benzonitrile isopropyl isopropyl 76. tert-butyl tert-butyl H 77. tert-butyl tert-butyl CN 78. tert-butyl tert-butyl F 79. tert-butyl tert-butyl Cl 80. tert-butyl tert-butyl NO.sub.2 81. tert-butyl tert-butyl pentafluorophenyl 82. tert-butyl tert-butyl tetrafluoro-2- (trifluoromethyl)phenyl 83. tert-butyl tert-butyl tetrafluoro-3- (trifluoromethyl)phenyl 84. tert-butyl tert-butyl tetrafluoro-4- (trifluoromethyl)phenyl 85. tert-butyl tert-butyl tetrafluoro-2-pyridyl 86. tert-butyl tert-butyl tetrafluoro-3-pyridyl 87. tert-butyl tert-butyl tetrafluoro-4-pyridyl 88. tert-butyl tert-butyl tetrafluoro-2-benzonitrile 89. tert-butyl tert-butyl tetrafluoro-3-benzonitrile 90. tert-butyl tert-butyl tetrafluoro-4-benzonitrile 91. nonafluoro-n-butyl nonafluoro-n- H butyl 92. nonafluoro-n-butyl nonafluoro-n- CN butyl 93. nonafluoro-n-butyl nonafluoro-n- F butyl 94. nonafluoro-n-butyl nonafluoro-n- Cl butyl 95. nonafluoro-n-butyl nonafluoro-n- NO.sub.2 butyl 96. nonafluoro-n-butyl nonafluoro-n- pentafluorophenyl butyl 97. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-2- butyl (trifluoromethyl)phenyl 98. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-3- butyl (trifluormethyl)phenyl 99. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-4- butyl (trifluoromethyl)phenyl 100. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-2-pyridyl butyl 101. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-3-pyridyl butyl 102. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-4-pyridyl butyl 103. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-2-benzonitrile butyl 104. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-3-benzonitrile butyl 105. nonafluoro-n-butyl nonafluoro-n- tetrafluoro-4-benzonitrile butyl 106. pentafluorophenyl pentafluoro- H phenyl 107. pentafluorophenyl pentafluoro- CN phenyl 108. pentafluorophenyl pentafluoro- F phenyl 109. pentafluorophenyl pentafluoro- Cl phenyl 110. pentafluorophenyl pentafluoro- NO.sub.2 phenyl 111. pentafluorophenyl pentafluoro- pentafluorophenyl phenyl 112. pentafluorophenyl pentafluoro- tetrafluoro-2- phenyl (trifluoromethyl)phenyl 113. pentafluorophenyl pentafluoro- tetrafluoro-3- phenyl (trifluoromethyl)phenyl 114. pentafluorophenyl pentafluoro- tetrafluoro-4- phenyl (trifluoromethyl)phenyl 115. pentafluorophenyl pentafluoro- tetrafluoro-2-pyridyl phenyl 116. pentafluorophenyl pentafluoro- tetrafluoro-3-pyridyl phenyl 117. pentafluorophenyl pentafluoro- tetrafluoro-4-pyridyl phenyl 118. pentafluorophenyl pentafluoro- tetrafluoro-2-benzonitrile phenyl 119. pentafluorophenyl pentafluoro- tetrafluoro-3-benzonitrile phenyl 120. pentafluorophenyl pentafluoro- tetrafluoro-4-benzonitrile phenyl 121. 4-pyrimidyl 4-pyrimidyl H 122. 4-pyrimidyl 4-pyrimidyl CN 123. 4-pyrimidyl 4-pyrimidyl F 124. 4-pyrimidyl 4-pyrimidyl Cl 125. 4-pyrimidyl 4-pyrimidyl NO.sub.2 126. 4-pyrimidyl 4-pyrimidyl pentafluorophenyl 127. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 128. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 129. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 130. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-pyridyl 131. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-pyridyl 132. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-pyridyl 133. 4-pyrimidyl 4-pyrimidyl tetrafluoro-2-benzonitrile 134. 4-pyrimidyl 4-pyrimidyl tetrafluoro-3-benzonitrile 135. 4-pyrimidyl 4-pyrimidyl tetrafluoro-4-benzonitrile 136. 2-pyrimidyl 2-pyrimidyl H 137. 2-pyrimidyl 2-pyrimidyl CN 138. 2-pyrimidyl 2-pyrimidyl F 139. 2-pyrimidyl 2-pyrimidyl Cl 140. 2-pyrimidyl 2-pyrimidyl NO.sub.2 141. 2-pyrimidyl 2-pyrimidyl pentafluorophenyl 142. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2- (trifluoromethyl)phenyl 143. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3- (trifluoromethyl)phenyl 144. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4- (trifluoromethyl)phenyl 145. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-pyridyl 146. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-pyridyl 147. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-pyridyl 148. 2-pyrimidyl 2-pyrimidyl tetrafluoro-2-benzonitrile 149. 2-pyrimidyl 2-pyrimidyl tetrafluoro-3-benzonitrile 150. 2-pyrimidyl 2-pyrimidyl tetrafluoro-4-benzonitrile 151. 3,5-bis(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 152. 3,5-bis(trifluoro- trifluoromethyl H methyl)-phenyl 153. phenyl pentafluoroethyl H 154. furan-2-yl trifluoromethyl H 155. furan-2-yl pentafluoroethyl H 156. 3,5-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 157. 3′,5′-bis(trifluoro- pentafluoroethyl H methyl)-[1,1′- biphenyl]-4-yl 158. 3′,5′-bis(trifluoro- trifluoromethyl H methyl)-[1,1′- biphenyl]-4-yl 159. 4-fluoro-3-trifluoro- pentafluoroethyl H methyl-phenyl 160. 4-fluoro-3-trifluoro- 3,5-bis(trifluoro- H methyl-phenyl methyl)-phenyl 161. 3,4,5-trifluorophenyl 3,4,5-trifluoro- H phenyl 162. 3,4,5-trifluorophenyl pentafluoroethyl H 163. 4-(trifluoro- 4-(trifluoro- H methyl)phenyl methyl)phenyl 164. 4-(trifluoro- pentafluoroethyl H methyl)phenyl 165. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- H methyl)phenyl methyl)phenyl 166. 2,4,6-tris(trifluoro- Pentafluoroethyl H methyl)phenyl 167. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 168. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- CN methyl)phenyl methyl)phenyl 169. 3,5-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 170. 3,4-bis(trifluoro- 3,4-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 171. 3,4-bis(trifluoro- trifluoromethyl H methyl)-phenyl 172. 3,4-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 173. 3,4-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 174. 3,4-bis(trifluoro- 3,4-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 175. 4-cyano-3-(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 176. 4-cyano-3-(trifluoro- pentafluoroethyl H methyl)-phenyl 177. 3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 178. 4-cyano-2,6-bis(tri- 4-cyano-2,6- H fluoromethyl)- bis(trifluoro- phenyl methyl)-phenyl 179. 4-cyano-2,6-bis(tri- pentafluoroethyl H fluoromethyl)- phenyl 180. 2,4-bis(trifluoro- 2,6-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 181. 2,4-bis(trifluoro- 2,6-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 182. 4-(3′,5′-bis(trifluoro- pentafluoroethyl H methyl)phenyl)-2,6- bis(trifluoromethyl)- phenyl 183. phenyl phenyl CN 184. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CF.sub.3 methyl)-phenyl methyl)-phenyl 185. 3,5-bis(trifluoro- trifluoromethyl CF.sub.3 methyl)-phenyl 186. phenyl pentafluoroethyl CF.sub.3 187. 3,5-bis(trifluoro- pentafluoroethyl CF.sub.3 methyl)-phenyl 188. 3,4,5- 3,4,5- CF.sub.3 trifluorophenyl trifluorophenyl 189. 4-(trifluoro- 4-(trifluoro- CF.sub.3 methyl)phenyl methyl)phenyl 190. phenyl phenyl CF.sub.3

[0229] Especially preferred are the compounds of formula (I.a), wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in table 3:

TABLE-US-00003 TABLE 3 R.sup.1 R.sup.2 R.sup.3 191. pentafluorophenyl pentafluorophenyl H 192. phenyl phenyl CN 193. tert-butyl tert-butyl H 194. tert-butyl tert-butyl CN 195. 3,5-bis(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 196. 3,5-bis(trifluoro- trifluoromethyl H methyl)-phenyl 197. phenyl pentafluoroethyl H 198. furan-2-yl trifluoromethyl H 199. furan-2-yl pentafluoroethyl H 200. 3,5-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 201. 3′,5′-bis(trifluoro- pentafluoroethyl H methyl)-[1,1′- biphenyl]-4-yl 202. 3′,5′-bis(trifluoro- trifluoromethyl H methyl)-[1,1′- biphenyl]-4-yl 203. 4-fluoro-3-trifluoro- pentafluoroethyl H methyl-phenyl 204. 4-fluoro-3-trifluoro- 3,5-bis(trifluoro- H methyl-phenyl methyl)-phenyl 205. 3,4,5-trifluorophenyl 3,4,5-trifluoro- H phenyl 206. 3,4,5-trifluorophenyl pentafluoroethyl H 207. 4-(trifluoro- 4-(trifluoro- H methyl)phenyl methyl)phenyl 208. 4-(trifluoro- pentafluoroethyl H methyl)phenyl 209. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- H methyl)phenyl methyl)phenyl 210. 2,4,6-tris(trifluoro- Pentafluoroethyl H methyl)phenyl 211. 3,5-bis(trifluoro- 3,5-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 212. 2,4,6-tris(trifluoro- 2,4,6-tris(trifluoro- CN methyl)phenyl methyl)phenyl 213. 3,5-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 214. 3,4-bis(trifluoro- 3,4-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 215. 3,4-bis(trifluoro- trifluoromethyl H methyl)-phenyl 216. 3,4-bis(trifluoro- pentafluoroethyl 3,5-bis(trifluoromethyl)- methyl)-phenyl phenyl 217. 3,4-bis(trifluoro- pentafluoroethyl H methyl)-phenyl 218. 3,4-bis(trifluoro- 3,4-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 219. 4-cyano-3-(trifluoro- 3,5-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 220. 4-cyano-3-(trifluoro- pentafluoroethyl H methyl)-phenyl 221. 3,5-bis(trifluoro- pentafluoroethyl CN methyl)-phenyl 222. 4-cyano-2,6-bis(tri- 4-cyano-2,6- H fluoromethyl)- bis(trifluoro- phenyl methyl)-phenyl 223. 4-cyano-2,6-bis(tri- pentafluoroethyl H fluoromethyl)- phenyl 224. 2,4-bis(trifluoro- 2,6-bis(trifluoro- H methyl)-phenyl methyl)-phenyl 225. 2,4-bis(trifluoro- 2,6-bis(trifluoro- CN methyl)-phenyl methyl)-phenyl 226. 4-(3′,5′-bis(trifluoro- pentafluoroethyl H methyl)phenyl)-2,6- bis(trifluoromethyl)- phenyl

[0230] In formula (I.a) the four ligands L.sub.2, L.sub.3 and L.sub.4 bound to the cerium atom have the same meanings.

[0231] The homoleptic compounds of formulae (I.1) and (I) are produced by reacting the β-diketone ligand with a ceric salt. Usually the ceric salt is soluble in the reaction medium. Suitable salts are ceric ammonium nitrate and ceric ammonium sulphate. The β-diketone ligands are either commercial available or they can be prepared by a synthesis known to a skilled person.

[0232] The heteroleptic compounds of formula (I.1) are produced by [0233] mixing two different homoleptic cerium compounds in a suitable solvent, [0234] mixing a homoleptic cerium compound with a ligand or its alkaline/earth alkaline salt different from the ligands of the compound, [0235] vapor deposition of two different homoleptic cerium compounds, [0236] vapor deposition (vapor co-condensation) of homoleptic cerium compounds with a ligand different from the ligands of the compound.

[0237] Component

[0238] In the context of the invention, an electronic component is understood to be a discrete or integrated electrical component, which uses the properties of compounds of the general formula (I.1) or (I) or semiconductor matrix materials containing a compound of the general formula (I.1) or (I). In a special embodiment, the electronic component has a layer structure comprising in particular 2, 3, 4, 5, 6, 7 or more layers, wherein at least one of the layers contains at least one compound of the general formula (I.1) or (I). In particular, the electronic component has a layer structure comprising in particular 2, 3, 4, 5, 6, 7 or more layers, wherein at least one of the layers contains at least one compound of the general formula (I). Each of the layers may also contain inorganic materials, or the component may also comprise layers, which are composed entirely from inorganic materials.

[0239] Preferably, the electronic component is selected from organic field effect transistors (OFETs), organic electroluminescent devices, organic solar cells (OSCs), devices for electrophotography, organic optical detectors, organic photoreceptors, light-emitting electrochemical cells (LECs) and organic laser diodes. Organic field effect transistors (OFETs) are preferably organic thin film transistors (OTFTs). Organic electroluminescent devices are preferably organic light-emitting diodes (OLEDs). Organic solar cells are preferably exciton solar cells, dye sensitized solar cells (DSSCs) or perovskite solar cells. Devices for electrophotography are preferably photoconductive materials in organic photoconductors (OPC).

[0240] Preferably, the electronic component according to the invention is in the form of an organic light-emitting diode, an organic solar cell, a photovoltaic cell, an organic diode or an organic transistor, preferably a field effect transistor or thin-film transistor or a Perovskite solar cell.

[0241] The electronic component may be preferably an organic electro-luminescent device, in particular in the form of an organic light-emitting diode (OLED). An organic electroluminescent device comprises a cathode, an anode and at least one emitting layer. In addition to these layers, it may also comprise other layers, e.g. one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge generation layers. Intermediate layers, which have e.g. an exciton-blocking-function can also be inserted between two emitting layers. Not all of these layers must necessarily be present.

[0242] A preferred embodiment is an electronic component, in particular in the form of an OLED, wherein the layer comprising the compound of formula (I.1) or (I) is a hole transport layer or a hole injection layer. Especially, the electronic component, in particular in the form of an OLED, wherein the layer comprising the compound of formula (I) is a hole transport layer, a hole injection layer or an electron blocking layer. Generally, a hole injection layer is a layer which facilitates electron injection from the anode into the organic semiconductor matrix material. The hole injection layer can be placed directly adjacent to the anode. A hole transport layer transports the holes from the anode to the emitting layer and is located between a hole injection layer and an emitting layer.

[0243] A preferred embodiment is an electronic component in the form of an organic solar cell. Generally organic solar cells are layered and usually comprises at least the following layers: anode, at least one photoactive layer and cathode. These layers are generally applied to a substrate commonly used for this purpose. The photoactive region of the solar cell may comprise two layers, each of which has a homogeneous composition and forms a flat donor-acceptor heterojunction. A photoactive region can also comprise a mixed layer and form a donor-acceptor heterojunction in the form of a donor-acceptor bulk heterojunction. In addition to these layers, the organic solar cell can also comprises other layers, e.g. selected from [0244] Layers with electron transport layer properties (electron transport layer, ETL), [0245] Layers comprising a hole-conducting material (hole transport layer, HTL), these do not have to absorb radiation, [0246] Exciton and hole blocking layers (e.g. EBLs), these must not absorb, and [0247] Multiplier layers.

[0248] Another preferred embodiment is an electronic component in the form of an organic solar cell, wherein the layer, which comprises the compound of formula (I.1) or (I), has electron conductivity properties (electron transport layer, ETL). Especially, the electronic component is in the form of an organic solar cell, wherein the layer, which comprises the compound of formula (I), has electron conductivity properties (electron transport layer, ETL).

[0249] A special embodiment is an electronic component, especially in the form of an organic solar cell, wherein the layer, which comprises at least one of the compounds of formula (I.1) or (I) is part of a pn-junction connecting a light absorbing unit to an additional light absorbing unit in a tandem device or in a multi-stacked device and/or a pn-junction connecting a cathode or an anode to a light absorbing unit. In particular, the electronic component is in the form of an organic solar cell, wherein the layer which comprises at least one of the compounds of formula (I) is part of a pn-junction connecting a light absorbing unit to an additional light absorbing unit in a tandem device or in a multi-stacked device and/or a pn-junction connecting a cathode or an anode to a light absorbing unit.

[0250] Semiconductor Matrix Materials

[0251] The compounds of formula (I.1) or (I) according to the invention and used according to the invention, as well as their charge transfer complexes, their reduction products, can be used as doping agents in organic semiconductor matrix materials, in particular as p-dopant in hole transport layers. The doped semiconductor matrix material, preferably comprising at least one electron donor and at least one compound of the formula (I.1) or (I), as defined above. The electron donor is preferably selected from 4,4′,4″-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA), 4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA), N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD), (2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spiro-bifluorene (spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine, N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-spiro-bifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine) (BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, diaminoterphenylene, diaminotrimethylphenylindanes, N,N′-bis(9,9-dimethylfluoren-2-yl)-N,N′-diphenyl-benzidine (BF-DPB), N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine) (BPAPF), N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-4,4′-diamine (TDMFB), N-([1,1′-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD), N([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and mixtures thereof.

[0252] Suitable diaminoterphenyls are described in DE 102012007795. Diaminotrimethylphenylindanes are described in WO 2018/206769.

[0253] In particular, the electron donors are selected from 4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), 4,4′,4″-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA), N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD), (2,2′,7,7′-tetrakis-(N,N-diphenylamino)-9,9′-spirobifluorene (spiro-TTB), N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine, N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-spiro-bifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N′-((9H-fluoren-9,9-diyl)bis(4,1-phenylen))bis(N-([1,1-biphenyl]-4-yl)-[1,1-biphenyl]-4-amine) (BPAPF), N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl) -N-(6-methoxy-[1,1-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine, phenyl]-4-yl)-N-(4-(6-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, N,N′-di([1,1′-biphenyl]-4-yl)-3-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(9,9′-spirobi[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine, N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine, 9-(4-(6-(9H-carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole, N-([1,1-biphenyl]-4-yl)-3-(4-([1,1-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, 3-(4-(bis(6-methoxy-[1,1′-biphenyl]-3-yl)amino)phenyl)N,N-bis(6-methoxy-[1,1-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N1-([1,1′-biphenyl]-4-yl)-N1-(4-(6-([1,1-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, N,N-di([1,1′-biphenyl]-4-yl)-4′-(6-(4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1′-biphenyl]-4-amine, N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N,N′-bis(9,9-dimethyl-fluoren-2-yl)N,N′-diphenyl-benzidine (BF-DPB), N,N′-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine) (BPAPF), N4,N4,N4′,N4′-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)1,1′-biphenyl]-4,4′-diamine (TDMFB), N-([1,1′-biphenyl]-2-yl)-N(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene](spiro-MeO-TPD), a mixture of N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and mixtures thereof.

[0254] Of course, other suitable organic semiconductor matrix materials, especially hole-conducting materials with semiconducting properties, can also be used.

[0255] Doping

[0256] The doping can take place in particular in such a manner that the molar ratio of matrix molecule to compounds of formula (I.1) or (I) is 10000: 1 to 1:1, preferably 1000: 1 to 2: 1, especially 5:1 to 100: 1. In particular, the doping can take place in particular in such a manner that the molar ratio of matrix molecule to compounds of formula (I) is 10000:1 to 1:1, preferably 1000:1 to 2:1, especially 5:1 to 100: 1.

[0257] Preparation of the Doped Semiconductor Matrix Material

[0258] The doping of the particular matrix material (in the following also indicated as hole-conducting matrix HT) with the compounds of the general formula (I.1) or (I) according to the invention and used according to the invention can be produced by one or a combination of the following processes: [0259] a) Mixed evaporation in the vacuum with a source for HT and a source for at least one compound of the general formula (I.1) and (I) in particular at least one compound of the general formula (I). [0260] b) Sequential deposition of HT and at least one compound of the general formula (I.1) or (I), in particular at least one compound of the general formula (I), with subsequent inward diffusion of the doping agent by thermal treatment. [0261] c) Doping of an HT layer by a solution of at least one compound of the general formula (I.1) or (I), in particular at least one compound of the general formula (I), with subsequent evaporation of the solvent by thermal treatment. [0262] d) Surface doping of an HT layer by a layer of at least one compound of the general formula (I.1) or (I), in particular at least one compound of the general formula (I), applied on either or both surfaces of the HT layer. [0263] e) Preparation of a solution of host and at least one compound of the general formula (I.1) or (I), in particular at least one compound of the general formula (I), and forming a film from the solution e.g. by coating, casting or printing techniques or other film preparing techniques known to a person skilled in the art.

[0264] Another object of the invention is the use of a compound (I.1) or a mixture thereof or the use of a compound (I) or a mixture thereof, in particular the use of a compound (I) or a mixture thereof as defined above [0265] as organic semiconductor, [0266] as doping agent in organic semiconductor matrix materials, especially as p-dopant in hole transport layers, [0267] as electron transport material, [0268] as charge injector in a charge injection layer, [0269] as cathode material in organic batteries, [0270] as electrochromic material.

[0271] A further object of the invention is the use of Ce(III) complex anions obtained by reduction of a compound (I.1) or (I) as defined above or of charge transfer complexes of a compound (I.1) or (I) as defined above with electron donors as organic conductor or as electrochromic material.

[0272] A further object of the invention are compounds of the general formula (I.1)

Ce.sup.4+(L.sub.1L.sub.2L.sub.3L.sub.4).sup.4−  (I.1),

and mixtures thereof, wherein

[0273] L.sub.1; L.sub.2; L.sub.3; and L.sub.4 are independently from each other a bidentate ligand having the general formula (I.2)

##STR00025##

wherein [0274] X and W independently from each other represent O, S or NR.sup.6; [0275] Y represents N or CR.sup.3−;

[0276] R.sup.1, R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.8−; [0277] R.sup.3 represents hydrogen, CN, nitro, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0278] R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0279] R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; [0280] R.sup.6 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0281] R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−, [0282] R.sup.8 represents CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.6-C.sub.14-aryl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl;

[0283] with the proviso that the following compounds are excluded:

##STR00026## ##STR00027##

[0284] A further object of the invention are compounds of the general formula (I)

##STR00028##

[0285] and their charge transfer complexes, their reduction products and mixtures thereof, wherein [0286] X and W independently from each other represent 0, S or NR.sup.6; [0287] Y represents N or CR.sup.3; [0288] R.sup.1, R.sup.2 independently from each other represent CN, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.8−; [0289] R.sup.3 represents hydrogen, CN, nitro, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, NR.sup.4aR.sup.4b, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0290] R.sup.4aR.sup.4b independently from each other represent hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0291] R.sup.5 represents CN, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl; [0292] R.sup.6 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.6-C.sub.14-aryl or hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NR.sup.7, O, S, SO and SO.sub.2, wherein aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−, [0293] R.sup.7 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.6-C.sub.14-aryl, wherein aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R.sup.5−; [0294] R.sup.8 represents CN, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.6-C.sub.14-aryl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl;

[0295] with the proviso that the following compounds are excluded:

##STR00029## ##STR00030##

[0296] The following examples illustrate the invention without limiting it in any way.

Examples

[0297] Synthesis of 1:

##STR00031##

[0298] 1,3-bis(perfluorophenyl)propane-1,3-dione was prepared according to literature (R. Filler et al., J. Org. Chem. 35(4), 1970, 930).

[0299] 1,3-Bis(perfluorophenyl)propane-1,3-dione (1.61 g, 4.00 mmol) was dissolved in ethanol (50 ml) and 1M NaOH in ethanol (4 ml, 4 mmol) was added. The solution was stirred for 5 minutes, then ceric (IV) ammonium nitrate (0.55 g, 1 mmol) was added. The dark red solution was stirred for 2 hours. The volatiles were removed in vacuo and the residue suspended in hexane (40 ml). After refluxing for 10 min, the suspension was filtered while hot and the filtrate was allowed to cool to room temperature. Dark red crystals were isolated by vacuum filtration and dried under vacuum. The solid was recrystallized from hexane filtered and dried (0.77 g, 0.43 mmol, 44% yield).

[0300] .sup.1H NMR (300 MHz, CDCl.sub.3) δ 6.09.

[0301] .sup.19F NMR (282 MHz, CDCl.sub.3) δ-139.25, −139.31, −149.63, −149.70, −149.78, −160.69, −160.70, 160.73, −160.78, −160.80, −160.85, −160.88, −160.89.

[0302] Melting point: 183° C.

[0303] Cyclovoltametry in dichloromethane showed the following:

E.sub.1/2(vs.Fc/Fc.sup.+)=+0,13V

[0304] Cyclovoltametry in acetonitrile showed the following:

E.sub.1/2(vs.Fc/Fc.sup.+)=+0,1V

[0305] Preparation of the samples:

[0306] A substrate (laboratory glass 1×1 cm) was cleaned with acetone, ethanol and isopropanol in an ultrasonic bath.

[0307] The following solutions/concentrations were used for solvent processing: [0308] 1. spiro-MeO-TAD (N2,N2,N2′,N2′,N7,N7,N7′,N7′-octakis(4-methoxyphenyl)-9,9′-spirobi[9H-fluoren]-2,2′,7,7′-tetramine) in chlorobenzene: 30 mg/ml [0309] 2. Dopant 1 and Spiro-MeO-TAD and in chlorbenzene: 3 mg/ml (dopant 1) and 30 mg/ml Spiro-MeO-TAD

[0310] A spincoater from Sawatec AG, Switzerland, was used for the application of the layers. For this purpose, the substrate surface was wetted with solution (a drop was placed in the middle of the substrate). The spin coating was carried out for 60 seconds at 1000 rpm with closed lid and open ventilation slits. Subsequently, gold metal contacts were deposited by evaporation in a vacuum (10-7 mbar) (30 nm, 1 Å/s).

[0311] Conductivity Spiro-MeG-TAD without dopant: <1.Math.10.sup.−9 S/cm

[0312] Conductivity Spiro-MeG-TAD with 10 wt % 1 as dopant: 8.4.Math.10.sup.−5 S/cm

[0313] The compound has been solution processed together with the hole transport material CAS [1364603-07-5]. At a doping concentration of 4 mol % a conductivity of 2.6.Math.10.sup.−6 S/cm has been achieved.

[0314] Synthesis of 2:

##STR00032##

[0315] Compound 2 is commercially available and was sublimated without decomposition. The sublimation temperature T.sub.Tsubl was 130 to 140° C. (pressure; 2.Math.10.sup.−6 mbar).

[0316] Synthesis of 3:

##STR00033##

[0317] 2-Benzoyl-3-oxo-3-phenylpropanenitrile was prepared according to literature (Lava R. Kadel, John R. Kromer, Curtis E. Moore, David M. Eichhorn Polyhedron 125, 2017, 206-218.).

[0318] 2-Benzoyl-3-oxo-3-phenylpropanenitrile (0,50 g, 2 mmol) was dissolved in ethanol (15 ml), and 1M NaOH in ethanol (2 ml, 2 mmol) was added. The solution was stirred for 5 minutes, then ceric(IV) ammonium nitrate (0,27 g, 0.5 mmol) dissolved in ethanol (5 ml) was added. The dark red solution was stirred for 15 min and after that filtered. The dark solid was washed with water (100 ml) and ethanol (10 ml) and dried. 460 mg of a dark red solid were obtained.

[0319] Cyclovoltametry in dichloromethane showed the following potential:

E.sup.1/2(vs.Fc/Fc.sup.+)=+0,03V

[0320] Synthesis of 4:

##STR00034##

[0321] 4,4-Dimethyl-3-oxo-2-pivaloylpentanenitrile was prepared according to literature (C. M. Silvernail et al., Polyhedron 20, 2001, 3113.).

[0322] 4,4-Dimethyl-3-oxo-2-pivaloylpentanenitril (0,84 g, 4 mmol) was dissolved in ethanol (30 ml), and 1M NaOH in ethanol (4 ml, 4 mmol) was added. The solution was stirred for 5 minutes, then ceric(IV) ammonium nitrate (0,55 g, 1 mmol) dissolved in ethanol (10 ml) was added. The dark red solution was stirred for 15 min. The solvent was removed in vacuo. The residue was extracted with diethylether (50 ml) and filtered. The solvent of the filtrate was removed under vacuum. Dark red solid, 500 mg, 51% yield.

[0323] Compound 4 was sublimated. A dark red solid was obtained. The sublimation temperature T.sub.subl was 160° C. (pressure; 2.Math.10.sup.−6 mbar).

[0324] Cyclovoltametry in dichloromethane showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+)=−0,08V

[0325] Synthesis of 5

##STR00035##

[0326] Diisopropylamine (3 g, 30 mmol) was dissolved in 25 mL dry toluene. The solution was cooled to 0° C. and n-BuLi (n-butyllithium, 1.6M in hexane, 19 mL, 30 mmol) was added. After 10 min, 3′,5′-Bis(trifluoromethyl)acetophenone (7.68 g, 30 mmol) was added. After 1 min, 3′,5′ bis(trifluoromethyl)benzoyl chloride (5.5 g, 20 mmol) was added and the cooling bath was removed. After 2 min, acetic acid conc. (10 mL) was added followed by 20 mL of water and 10 mL of toluene. The two phases were separated, the organic phase was dried over MgSO.sub.4 and rotated off under reduced pressure. The crude diketone was recrystallized from hexane (yield of 1,3-bis(3,5-bis(trifluoromethyl)phenyl)propane-1,3-dione 3.2 g, 6.45 mmol, 33%).

[0327] 1,3-bis(3,5-bis(trifluoromethyl)phenyl)propane-1,3-dione (2.57 g, 5.18 mmol) was dissolved in ethanol (100 ml) and 1M NaOH in ethanol (5.2 ml, 5.2 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric ammonium nitrate (0.71 g, 1.3 mmol) in ethanol (40 ml) was added. The dark red solution was stirred for 15 min and filtered. The volatiles were removed in vacuo and the residue was redissolved in dichloromethane (DCM, 300 ml) and washed with water (100 ml). The organic phase was then dried over MgSO.sub.4 and concentrated under reduced pressure. Hexane (400 mL) was added to yield purple crystals, which were filtered and dried under vacuum (2.5 g, 1.17 mmol, 90% yield).

[0328] Melting point: 237° C. (onset) at 10 K/min, determined with DSC

[0329] Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+(MeCN):=−0.04V

[0330] The compound 5 was co-evaporated with the hole transport material spiro-MeO-TPD (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluoren]. At a doping concentration of 3 mol % a conductivity of 8.2.Math.10.sup.−5 S/cm has been achieved.

[0331] The compound was co-evaporated with the hole transport material MeO-TPD (N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine). At a doping concentration of 3 mol % a conductivity of 5.2.Math.10.sup.−5 S/cm has been achieved.

[0332] Synthesis of 6

##STR00036##

[0333] 1-(3,5-bis(trifluoromethyl)phenyl)-4,4,4-trifluorobutane-1,3-dione was prepared according to literature (Liu et al., Molecules 2016, 21, 828.).

[0334] 1-(3,5-bis(trifluoromethyl)phenyl)-4,4,4-trifluorobutane-1,3-dione (2 g, 5.68 mmol) was dissolved in ethanol (50 ml) and 1M NaOH in ethanol (5.6 ml, 5.6 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric (IV) ammonium nitrate (0.78 g, 1.42 mmol) in ethanol (20 ml) was added. The dark red solution was stirred for 15 min and filtered. The volatiles were removed in vacuo and the residue redissolved in dichloromethane (300 ml), washed with water (100 ml). The organic phase was then dried over MgSO.sub.4 and concentrated under reduced pressure. Hexane (50 mL) was added to the mixture and the latter was stored at −20° C. overnight. The isolated solid was then recrystallized from hot hexane (1 g, 0.64 mmol, 45%).

[0335] Melting point: 155° C. (peak) at 10 K/min determined with DSC Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+(MeCN):=+0.35V

[0336] The compound 6 was co-evaporated with the hole transport material BF-DPB (N,N′-bis(9,9-dimethyl-fluoren-2-yl)-N,N′-diphenyl-benzidine). With a doping concentration of 6 mol % a conductivity of 7.2.Math.10.sup.−6 S/cm has been achieved.

[0337] The compound was co-evaporated with the hole transport material MeO-TPD.

[0338] With a doping concentration of 9 mol % a conductivity of 1.6.Math.10.sup.−4 S/cm has been achieved.

[0339] The compound was co-evaporated with the hole transport material BPAPF.

[0340] With a doping concentration of 13 mol % a conductivity of 3.Math.10.sup.−5 S/cm has been achieved.

[0341] Synthesis of 7

##STR00037##

[0342] 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione is commercial available.

[0343] 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione (1.8 g, 8.1 mmol) was dissolved in ethanol (40 ml) and 1M NaOH in ethanol (8.1 ml, 8.1 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric (IV) ammonium nitrate (1.11 g, 2 mmol) in ethanol (20 ml) was added. The dark red precipitate was stirred for 15 min and filtered.

[0344] The solid was rinsed with water (100 ml). The latter was redissolved in dichloromethane (400 ml) and washed with water (2×200 ml). The organic phase was then dried over MgSO.sub.4 and concentrated under reduced pressure. Hexane (300 mL) was added to yield purple crystals, which were filtered, rinsed with hexane (50 ml), pentane (50 ml) and dried under vacuum (1.5 g, 1.46 mmol, 73% yield).

[0345] Melting point: 209° C. (peak) at 10 K/min determined with DSC Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+(MeCN):=+0.20V

[0346] Synthesis of 8

##STR00038##

[0347] 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione is commercial available.

[0348] 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione (1.57 g, 7.6 mmol) was dissolved in ethanol (40 ml) and 1M NaOH in ethanol (7.6 ml, 7.6 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric (IV) ammonium nitrate (1.04 g, 1.9 mmol) in ethanol (20 ml) was added. The dark red precipitate was stirred for 15 min and filtered. The solid was rinsed with water (100 ml). The latter was redissolved in dichloromethane (300 ml) and washed with water (100 ml). The organic phase was then dried over MgSO.sub.4 and concentrated under reduced pressure. Hexane (200 mL) was added to yield to purple crystals, which were filtered, rinsed with pentane (100 ml) and dried under vacuum (yield: 1.2 g, 1.32 mmol, 66%).

[0349] Melting point: 166° C. (peak) at 10 K/min determined with DSC.

[0350] Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+(MeCN):=+0.24V

[0351] Synthesis of 9

##STR00039##

[0352] 3′,5′ Bis(trifluoromethyl)acetophenone (4.32 g, 16.9 mmol) and ethyl 2,2,3,3,3-pentafluoropropanoate (4.86 g, 25.3 mmol) were dissolved in dry methanol (100 ml). MeONa (1.82, 33.8 mmol) in methanol (10 ml) was added and the mixture was refluxed for 2 hours. The resulting solutions was evaporated under reduced pressure. The crude was redissolved in EtOAc (100 ml) and HCl (6 M, 50 ml) was added. The organic phase was separated, dried over MgSO.sub.4 and rotated off. The red oily diketone was purified by vacuum distillation yielding to a pale yellow oil of 1-(3,5-bis(trifluoromethyl)phenyl)4,4,5,5,5-pentafluoropentane-1,3-dione (yield: 4.8 g, 12 mmol, 71%).

[0353] 1-(3,5-Bis(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoropentane-1,3-dione (2.22 g, 5.52 mmol) was dissolved in ethanol (50 ml) and 1M NaOH in ethanol (5.5 ml, 5.5 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric ammonium nitrate (0.76 g, 1.38 mmol) in ethanol (15 ml) was added. The dark red solution was stirred for 15 min and filtered. The solution was evaporated under reduced pressure. The red oil was extracted with hexane (10 ml) and crystallized upon standing overnight at room temperature. The isolated solid was recrystallized from hot hexane and stored at −20° C. (yield 2.02 g, 1.16 mmol, 84%).

[0354] Melting point: 129° C. (peak) at 10 K/min determined with DSC Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+(MeCN):=+0.46V

[0355] Synthesis of 10

##STR00040##

[0356] 1-(3′,5′-Bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)ethan-1-one (4 g, 12 mmol) was dissolved in THF (50 mL). The mixture was cooled to 0° C. and NaH (1.44 g, 60 mmol) was added.

[0357] The reaction mixture was stirred for 20 min, then ethyl 2,2,3,3,3-pentafluoropropanoate (6.9 g, 36 mmol) was added. The cold bath was removed and the mixture was stirred overnight. The solution was concentrated under reduced pressure, water (20 mL) was added followed by HCl (6M, 15 mL). The mixture was extracted with ethyl acetate (300 mL). The organic phase was washed with water (50 mL) and brine (50 mL), dried over MgSO.sub.4 and rotated off. The crude material was purified by filtration over silica (DCM as eluent), yielding a pale red solid of 1-(3′,5′-bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)-4,4,4-trifluorobutane-1,3-dione (yield: 3.2 g, 62%). 1-(3′,5′-bis(trifluoromethyl)-[1,1-biphenyl]-4-yl)-4,4,5,5,5-pentafluoropentane-1,3-dione (1.52 g, 3.17 mmol) was dissolved in ethanol (50 ml) and 1M NaOH in ethanol (3.2 ml, 3.2 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric (IV) ammonium nitrate (0.43 g, 0.79 mmol) in ethanol (20 ml) was added. The dark red solution was stirred for 15 min and filtered. The volatiles were removed in vacuo and the residue was redissolved in DCM (250 ml) and washed with water (100 ml). The organic phase was dried over MgSO.sub.4 and rotated off under reduced pressure. The mixture was redissolved in DCM (50 mL) and hexane (200 mL) was added. The solution was concentrated under reduced pressure and stored at −20° C. yielding dark red crystals, which were filtered and dried under vacuum (yield 0.6 g, 0.3 mmol, 37%).

[0358] Melting point: 214° C. (peak) at 10 K/min determined with DSC

[0359] Cyclovoltametry in acetonitrile showed the following potential:

E.sub.1/2(vs.Fc/Fc.sup.+:=+0.43V

[0360] Synthesis of 11

##STR00041##

[0361] Methyl 4-cyano-3-(trifluoromethyl)benzoate (2.09 g, 9.12 mmol) was dissolved in THF (50 mL). The mixture was cooled to 0° C. and NaH (706 mg, 29.4 mmol) was added. The reaction mixture was stirred for 20 min, then 1-(3,5-bis(trifluoromethyl)phenyl)ethan-1-one (1.95 g, 7.6 mmol) was added. The cold bath was removed and the mixture was stirred overnight. The solution was concentrated under reduced pressure, water (10 mL) was added followed by HCl (6M, 10 mL). The mixture was extracted with ethyl acetate (40 mL). The organic phase was washed with water (50 mL) and brine (50 mL), dried over MgSO.sub.4 and rotated off. The crude material was purified recrystallization from hot EtOH, yielding a colorless microcrystalline solid (1.32 g, 39%).

[0362] Complex:

[0363] 4-(3-(3,5-bis(trifluoromethyl)phenyl)-3-oxopropanoyl)-2-(trifluoromethyl)benzonitrile (1.32 g, 2.91 mmol) was dissolved in EtOH (50 ml) and 1M NaOH in EtOH (2.9 ml, 2.9 mmol) was added. The solution was stirred for 5 minutes, then a solution of ceric ammonium nitrate (0.4 g, 0.73 mmol) in EtOH (20 ml) was added. The dark red solution was stirred for 15 min and concentrated under reduced pressure. The dark red precipitate was filtered and rinsed with water (50 mL), EtOH (5 mL) and hexanes (15 mL). The isolated solid was dried under vacuum (1.06 g, 1.16 mmol, 75%).

[0364] Potential measured in acetonitrile+0,10V vs. Fc/Fc.sup.+.

[0365] Synthesis of 12 (Mixture of Homoleptic and Heteroleptic Cer-Complexes)

##STR00042##

[0366] A mixture of the ligands L.sup.1 (1.00 g) and L.sup.2 (1.02 g) with the molar ratio of 1:1) has been dissolved in 10 ml of EtOH. 9.2 ml of a 1M-solution of NaOH in EtOH was added in one portion while stirring. 1.26 g of ceric ammonium nitrate (CAN) dissolved in 10 ml of EtOH were added dropwise. The red precipitated was filtered off and washed two times with water. After drying the red powder was analyzed by mass spectrometry (Atmospheric Pressure Chemical Ionization APCI-, Advion ASAP Mass Spectrometer). The mass spectrum indicated formation of the two homoleptic complexes Ce(L.sup.1).sub.4 and Ce(L.sup.2).sub.4 as well as all possible heteroleptic complexes as depicted above.

[0367] Synthesis of 13: (Heteroleptic Cer-Complex)

##STR00043##

[0368] 52 mg of ligand salt NaL.sup.3 were dissolved in 10 ml EtOH and 216 mg of the complex Ce(L.sup.2).sub.4 were added. To the resulting suspension, 5 ml of THF were added and a homogeneous red solution was formed. Mass spectrometric analysis (Atmospheric Pressure Chemical Ionization APCI-, Advion ASAP Mass Spectrometer) of that solution showed partial formation of the new complex Ce(L.sup.2).sub.3L.sup.3.