Compounds based on fluoranthene and use thereof
The invention relates to fluoranthene derivatives of the general formula (I) in which R 1 , R 2 , R 3 and a are each defined according to the description, with the proviso that at least one of the R 1 or R 2 radicals is not hydrogen, to processes for their preparation and to the use of the fluoranthene derivatives as emitter molecules in organic light-emitting diodes (OLEDs), to a light-emitting layer comprising the inventive fluoranthene derivatives as emitter molecules, to an OLED comprising the inventive light-emitting layer and to devices comprising the inventive OLED.
1. An OLED comprising as emitter molecules fluoranthene derivatives of the general formula (I)
wherein R 1 and R 2 are each independently selected from
a linear, branched or cyclic, halogen-, nitro-, ether- or carboxyl-substituted or unsubstituted C 1 - to C 20 -alkyl group, in which one or more nonadjacent carbon atoms of the alkyl group which is/are not bonded directly to the fluoranthene skeleton may be replaced by Si, P, O or S,
a C 6 - to C 30 -aryl group which may be unsubstituted or substituted by alkoxy-, C 6 - to C 14 -aryl groups, or linear, branched or cyclic C 1 - to C 20 -alkyl groups which may be unsubstituted or may in turn be substituted by halogen, nitro, ether or carboxyl groups and/or in which one or more carbon atoms of the alkyl groups may be replaced by Si, P, O or S, or a C 4 - to C 14 -heteroaryl group which is unsubstituted or substituted by the substituents specified with regard to the aryl group and comprises at least one nitrogen or sulfur atom,
a group of the formula (E)- or (Z)-CH═CH—C 6 R 4 5 in which R 4 is H or CH 3 , a group of the formula
an acryloyl or methacryloyl group, a vinyl ether radical or a group of the formula
in which Y 1 is —CH═CH 2 , (E)- or (Z)- CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 or glycidyl, and
a fused aromatic such as naphthalene, anthracene, pyrene, phenanthrene and perylene, which may be substituted by one or more halogen, nitro, ether or carboxyl radicals, and
wherein R 3 is hydrogen.
2. The OLED according to claim 1 , wherein R 1 and R 2 in the fluoranthene derivatives are each independently a C 6 - to C 14 -aryl group which is unsubstituted or substituted by linear or branched, unsubstituted C 1 - to C 8 -alkyl groups, halogen or nitro groups, or a C 4 - to C 10 -heteroaryl group which is unsubstituted or substituted correspondingly to the aryl group and comprises at least one nitrogen or sulfur atom.
3. The OLED according to claim 2 , wherein R 1 and R 2 in the fluoranthene derivatives are each independently a phenyl group which is unsubstituted or substituted by linear or branched, unsubstituted C 1 - to C 8 -alkyl groups, halogen or nitro groups, a thiophene radical, a pyrrole radical, a pyridine radical or a pyrimidine radical.
4. The OLED according to claim 3 , wherein R 1 and R 2 in the fluoranthene derivatives are each independently a phenyl group which bears no, one or two substituents.
5. A light-emitting layer comprising one or more fluoranthene derivatives of the general formula (I) as defined in claim 1 as emitter molecules.
6. An OLED comprising a light-emitting layer according to claim 5 .
7. A device selected from the group consisting of stationary visual display units such as visual display units of computers, televisions, visual display units in printers, kitchen appliances, and advertising panels, illuminations, information panels and mobile visual display units such as visual display units in cell phones, laptops, vehicles, and destination displays on buses and trains, comprising an OLED according to claim 6 .
8. An OLED comprising as emitter molecules fluoranthene derivatives of the following general formula (I):
wherein R 1 and R 2 are each independently selected from:
a C 6 - to C 14 -aryl group which is unsubstituted or substituted by linear or branched, unsubstituted C 1 - to C 8 -alkyl groups, halogen or nitro groups; and
a C 4 - to C 10 -heteroaryl group which is unsubstituted or substituted by linear or branched, unsubstituted C 1 - to C 8 -alkyl groups, halogen or nitro groups, and comprises at least one nitrogen or sulfur atom; and
wherein R 3 is hydrogen.
9. The OLED according to claim 8 , wherein R 1 and R 2 are each independently selected from a phenyl group which is unsubstituted or substituted by linear or branched, unsubstituted C 1 - to C 8 -alkyl groups, halogen or nitro groups, a thiophene radical, a pyrrole radical, a pyridine radical or a pyrimidine radical.
10. The OLED according to claim 9 , wherein R 1 and R 2 are each independently selected from a phenyl group which bears no, one or two substituents.
11. A light-emitting layer comprising as emitter molecules one or more fluoranthene derivatives of the general formula (I) according to claim 8 .
12. An OLED comprising the light-emitting layer according to claim 11 .
13. A device comprising the OLED according to claim 12 , wherein the device is selected from stationary visual display units, visual display units in computers, visual display units in televisions, visual display units in printers, visual display units in kitchen appliances, visual display units in advertising panels, visual display units in illuminations, visual display units in information panels, mobile visual display units, visual display units in cell phones, visual display units in laptops, visual display units in vehicles, destination displays on buses and destination displays on trains.