Phenacene compounds for organic electronics
Phenacene compounds of formula (I) are disclosed. All the variables in the formula are the same as defined in the description. A thin film semiconductor comprising the above compounds, and a field effect transistor device, a photovoltaic device, an organic light emitting diode device and a unipolar or complementary circuit device comprising the thin film are also disclosed.
1. Phenacene compounds of formula I
wherein
one of groups a, b and c is X and the other two groups are C—R 1 and C—R 2 , respectively,
one of groups d, e and f is X and the other two groups are C—R 5 and C—R 6 , respectively,
wherein X are, independently of each other, selected from the group consisting of O, S and Se,
R 1 -R 10 are independently of each other H, halogene, —CN, —NO 2 or a linear or branched, saturated or unsaturated C 1 -C 40 hydrocarbon residue, which can be substituted 1- to 5-fold with halogen (F, Cl, Br, I), —OR a , —NR a 2 , —CN and/or —NO 2 , and wherein one or more CH 2 -groups can be replaced by —O—, —S—, —NR b —, —OC(O)— or —C(O)—, and wherein R a and R b are independently of each other H, C 1 -C 30 akyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 1 -C 30 haloalkyl, C 2 -C 30 haloalkenyl, C 2 -C 30 haloalkynyl or C 2 -C 30 acyl.
2. Phenacene compounds according to claim 1 of formulae Ia-If
wherein
X and R 1 -R 10 are as defined in claim 1 .
3. Phenacene compounds according to claim 1 , wherein X is O.
4. Phenacene compounds according to claim 1 , wherein X is S.
5. Phenacene compounds according to claim 1 , wherein R 7 -R 10 are hydrogen.
6. Phenacene compounds according to claim 1 , wherein R 3 and R 4 are hydrogen.
7. Phenacene compounds according to claim 1 , wherein R 1 , R 2 , R 5 and R 6 are independently of each other hydrogen or a C 1-20 alkyl group.
8. Phenacene compounds according to claim 2 of formula Ia, wherein X is S, R 1 and R 5 are a C 1-20 alkyl group and R 2 -R 4 and R 6 -R 10 are hydrogen.
9. A thin film semiconductor comprising one or more compounds of claim 1 .
10. A field effect transistor device comprising the thin film semiconductor of claim 9 .
11. A photovoltaic device comprising the thin film semiconductor of claim 9 .
12. An organic light emitting diode device comprising the thin film semiconductor of claim 9 .
13. A unipolar or complementary circuit device comprising the thin film semiconductor of claim 9 .
14. Phenacene compounds according to claim 1 , wherein X is Se.
15. Phenacene compounds according to claim 1 , wherein said R 1 -R 10 are independently of each other selected from the group consisting of H, halogene, C 1 -C 30 alkyl, C 1 -C 30 alkoxy, C 1 -C 30 alkylthio, C 1 -C 30 alkenyl, C 2 -C 30 alkynyl, C 1 -C 30 haloalkyl, C 2 -C 30 haloalkenyl, and C 2 -C 30 haloalkynyl.
16. Phenacene compounds according to claim 1 , wherein said R 1 -R 10 are independently of each other selected from the group consisting of H, halogen, C 1 -C 30 alkyl and C 1 -C 30 alkoxy.
17. Phenacene compounds according to claim 1 , wherein said R 1 -R 10 are independently of each other selected from the group consisting of H, halogen, and C 1 -C 30 alkyl.