Organic pentacene semiconducting layers
A compound of formula 8 and uses thereof in various electronic devices and in a formulation for ink jet printing and in an organic semiconducting layer formulation.
1. A compound of formula 8
wherein
R 15 , R 16 , and R 17 each independently are the same or different and each independently represents an optionally substituted C 1 -C 40 carbyl or hydrocarbyl group; an optionally substituted C 1 -C 40 alkoxy group; an optionally substituted C 6 -C 40 aryloxy group; an optionally substituted C 7 -C 40 alkylaryloxy group; an optionally substituted C 2 -C 40 alkoxycarbonyl group; or an optionally substituted C 7 -C 40 aryloxycarbonyl group;
A represents silicon or germanium;
one or more of the carbon atoms of the polyacene skeleton is or are optionally replaced by a heteroatom selected from N, P, As, O, S, Se and Te;
one or more of R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10 and R 11 is or are F and the ones of R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10 and R 11 which are not F, are H; or
R 2 and R 3 and R 9 and R 10 together with the carbon atoms to which they are attached form an optionally substituted C 4 -C 10 saturated or unsaturated ring intervened by one or more oxygen or sulphur atoms or a group represented by formula —N(R a ), wherein R a is a hydrogen atom or a hydrocarbon group; and
the ring positions of the polyacene skeleton other than the 1, 2, 3, 4, 6, 8, 9, 10, 11 and 13 positions are unsubstituted.
2. A compound of claim 1 , wherein two or more of R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10 and R 11 are F.
3. A compound of claim 1 , wherein one or more of R 2 , R 3 , R 9 and R 10 is or are F.
4. A compound of claim 1 , wherein two or more of R 2 , R 3 , R 9 and R 10 are F.
5. A compound of claim 1 , wherein R 2 and R 3 and R 9 and R 10 together with the carbon atoms to which they are attached form an optionally substituted C 4 -C 10 saturated or unsaturated ring intervened by one or more oxygen or sulphur atoms or a group represented by formula —N(R a ), wherein R a is a hydrogen atom or a hydrocarbon group.
6. A compound of claim 1 , wherein one or more of the carbon atoms of the polyacene skeleton is or are replaced by a heteratom selected from N, P, As, O, S, Se and Te.
7. A compound of claim 1 , which is
8. A compound of claim 1 , wherein R 15 , R 16 and R 17 are each C 1-10 alkyl or C 6-10 aryl, which in each case is optionally substituted with halogen atoms.
9. A formulation comprising one or more compounds according to claim 1 and further comprising one or more solvents.
10. A formulation of claim 9 , wherein the solvent is dichloromethane, trichloromethane, monochlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, cetone, methylethylketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetralin, decalin or a mixture thereof.
11. A formulation of claim 9 , wherein the solvent is a xylene, toluene, tetralin or o-dichlorobenzene.
12. A formulation for ink jet printing comprising one or more compounds according to claim 1 and further comprising one or more solvents selected from substituted and non-substituted xylene derivatives; C 1-2 -alkyl formamide; substituted and non-substituted anisoles; substituted and non-substituted phenol-ether derivatives; substituted heterocycles; substituted pyridines; pyrazines; pyrimidines; pyrrolidinones; substituted and non-substituted N,N-di-C 1-2 -alkylanilines; substituted and non-substituted fluorinated or chlorinated aromatics; benzene derivatives having a benzene ring substituted by one or more substituents wherein the total number of carbon atoms among the one or more substituents is at least three; dodecylbenzene; 1-methyl-4-tert-butylbenzene; terpineol; limonene; isodurene; terpinolene; cymene; and diethylbenzene.
13. In an electronic device, wherein the improvement comprises the presence of one or more compounds according to claim 1 in an organic semiconducting layer in said electronic device.
14. A field effect transistor (FET), organic light emitting diode (OLED), photodetector, chemical detector, photovoltaic cell (PVs), capacitor sensor, logic circuit, display or memory device, comprising a compound according to claim 1 in an organic semiconducting layer.
15. In an electronic device, wherein the improvement comprises the presence of a compound according to claim 7 in an organic semiconducting layer in said electronic device.
16. A formulation comprising a compound according to claim 7 and one or more solvents, which one or more solvents are dichloromethane, trichloromethane, monochlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methylethylketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetralin, decalin or a mixture thereof.
17. A compound according to claim 1 , wherein four of R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , R 10 and R 11 , are F.
18. A compound according to claim 1 , wherein A represents silicon.
19. A compound according to claim 1 , wherein A represents germanium.
20. A compound of claim 1 , wherein R 15 , R 16 and R 17 are each C 1-10 alkyl.