Synthesis of phenyl-substituted fluoranthenes by a diesel-alder and the use thereof

1. A fluoranthene of the general formula I

wherein R 1 , R 2 , R 3 are each independently hydrogen, alkyl, an aromatic radical, a fused aromatic ring system, or a heteroaromatic radical;

wherein at least one of the radicals R 1 , R 2 and/or R 3 is not hydrogen;

wherein

X is an alkyl radical or a radical of the formula (I′)

or an oligophenyl group; and

wherein, when X is a radical of the formula (I′), in the radial of the formula (I′), R 1 to R 3 have the same meanings as in formula (I);

wherein the oligophenyl group is a group of the general formula (IV)

wherein Ph is in each case phenyl which, optionally, may be substituted in all 5 substitutable positions by a group of the formula (IV),

wherein, in the oligophenyl group of the general formula (IV), the indexes m 1 , m 3 and m 5 are each 0 and m 2 and m 4 are each 1, or the indexes m 2 and m 4 are each 0 and m 1 , m 3 and m 5 are each 1;

when X is an alkyl radical n is 2 or 3,

when X is a radical of the formula (I′) n is 1,

when X is an oligophenyl group n is 1;

with the proviso that R 1 , R 2 , R 3 and X are not at the same time phenyl.

2. The fluoranthene according to claim 1 , wherein R 1 and R 3 are each a phenyl radical.

3. A fluoranthene of the general formula I

wherein R 1 , R 2 , R 3 are each independently hydrogen, alkyl, an aromatic radical, a fused aromatic ring system, or a heteroaromatic radical;

wherein at least one of the radicals R 1 , R 2 and/or R 3 is not hydrogen;

wherein

X is an alkyl radical, and

n is 2 or 3.

4. An organic light-emitting diode comprising as an emitter molecule a fluoranthene of the general formula (I)

wherein R 1 , R 2 , R 3 are each independently hydrogen, alkyl, an aromatic radical, a fused aromatic ring system, or a heteroaromatic radical;

wherein at least one of the radicals R 1 , R 2 and/or R 3 is not hydrogen;

wherein

X is an alkyl radical or a radical of the formula (I′)

or an oligophenyl group;

wherein, when X is a radical of the formula (I′), in the radial of the formula (I′), R 1 to R 3 have the same meanings as in formula (I);

wherein the oligophenyl group is a group of the general formula (IV)

wherein Ph is in each case phenyl which, optionally, may be substituted in all 5 substitutable positions by a group of the formula (IV),

wherein, in the oligophenyl group of the general formula (IV), the indexes m 1 , m 3 and m 5 are each 0 and m 2 and m 4 are each 1, or the indexes m 2 and m 4 are each 0 and m 1 , m 3 and m 5 are each 1; and

when X is an alkyl radical n is 2 or 3,

when X is a radical of the formula (I′) n is 1,

when X is an oligophenyl group n is 1.

5. A light-emitting layer comprising one or more floranthenes of the general formula (I) according to claim 1 .

6. An organic light-emitting diode (OLED) comprising the light-emitting layer according to claim 5 .

7. A device selected from the group consisting of a stationary VDU and a mobile VDU; comprising an OLED according to claim 6 .

8. An organic light-emitting diode comprising as an emitter molecule the fluoranthene according to claim 1 .

9. A light-emitting layer comprising one or more fluoranthenes of the general formula (I) as defined in claim 2 as emitter molecule(s).

10. An organic light-emitting diode (OLED) comprising the light-emitting layer according to claim 9 .

11. A device selected from the group consisting of a stationary VDU and a mobile VDU; comprising the OLED according to claim 10 .

12. The device according to claim 7 , wherein the device is a stationary VDU, and wherein the stationary VDU is selected from the group consisting of a computer VDU, a television VDU, a printer VDU, a kitchen appliance VDU, an advertising sign VDU, a lighting VDU, and an information sign VUD.

13. The device according to claim 7 , wherein the device is a mobile VDU, and wherein the mobile VDU is selected from the group consisting of a mobile telephone VDU, a laptop VDU, a vehicle VDU, a bus destination VDU, and a train destination VDU.

14. The device according to claim 11 , wherein the device is a stationary VDU, and wherein the stationary VDU is selected from the group consisting of a computer VDU, a television VDU, a printer VDU, a kitchen appliance VDU, an advertising sign VDU, a lighting VDU, and an information sign VDU.

15. The device according to claim 11 , wherein the device is a mobile VDU, and wherein the mobile VDU is selected from the group consisting a mobile telephone VDU, a laptop VDU, a vehicle VDU, a bus destination VDU and a train destination VDU.

16. The device of claim 7 , wherein the device is a stationary VDU.

17. The device of claim 7 , wherein the device is a mobile VDU.

18. The device of claim 11 , wherein the device is a stationary VDU.