Naphthalenetetracarboxylic acid derivatives and their use as semiconductors
The present invention relates to naphthalenetetracarboxylic acid derivates, to a process for their preparation and to their use, especially as an n-type semiconductor.
1. A compound of the general formula I
where
at least one of the R 1 , R 2 , R 3 and R 4 radicals is a substituent which is selected from Br, F and CN, and the remaining radicals are each hydrogen,
Y 1 is O or NR a , where R a is hydrogen or an organyl radical,
Y 2 is O or NR b , where R b is hydrogen or an organyl radical,
Z 1 and Z 2 are each independently O or NR c , where R c is an organyl radical,
Z 3 and Z 4 are each independently O or NR d , where R d is an organyl radical,
where, in the case that Y 1 is NR a and at least one of the Z 1 and Z 2 radicals is NR c , R a with one R c radical may also together be a bridging group having 2 to 5 atoms between the flanking bonds, and
where, in the case that Y 2 is NR b and at least one of the Z 3 and Z 4 radicals is NR d , R b with one R d radical may also together be a bridging group having 2 to 5 atoms between the flanking bonds,
and provided that one of the following conditions apply:
a) three of the R 1 , R 2 , R 3 and R 4 radicals are each bromine or are each fluorine or are each cyano, and the remaining radical is hydrogen;
b) R 1 and R 2 are each independently selected from fluorine and cyano, and R 3 and R 4 are each hydrogen;
c) R 1 and R 3 are each independently selected from fluorine and cyano, and R 2 and R 4 are each hydrogen; or
d) R 1 and R 2 are each bromine, and R 3 and R 4 are each hydrogen.
2. The compound according to claim 1 , wherein three of the R 1 , R 2 , R 3 and R 4 radicals are each bromine or are each fluorine or are each cyano, and the remaining radical is hydrogen.
3. The compound according to claim 1 , wherein R 1 and R 2 are each independently selected from fluorine and cyano, and R 3 and R 4 are each hydrogen.
4. The compound according to claim 1 , wherein R 1 and R 3 are each independently selected from fluorine and cyano, and R 2 and R 4 are each hydrogen.
5. The compound according to claim 1 , wherein R 1 and R 2 are each bromine, and R 3 and R 4 are each hydrogen.
6. A compound of the formula:
7. A semiconductor comprising the compound of the general formula I as defined in claim 1 .
8. A semiconductor comprising the compound of claim 6 .
9. The compound according to claim 2 , wherein three of the R 1 , R 2 , R 3 and R 4 radicals are each bromine, and the remaining radical is hydrogen.
10. The compound according to claim 2 , wherein three of the R 1 , R 2 , R 3 and R 4 radicals are each fluorine, and the remaining radical is hydrogen.
11. The compound according to claim 2 , wherein three of the R 1 , R 2 , R 3 and R 4 radicals are each cyano, and the remaining radical is hydrogen.