Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device
View Patent ↗Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. This nitrogen-containing aromatic compound is represented by the general formula (1). Further, the present invention relates to organic electronic devices such as a light-emitting device, a thin-film transistor, and a photovoltaic device each using the nitrogen-containing aromatic compound. (L represents an m+n-valent aromatic hydrocarbon group or aromatic heterocyclic group, or a group arising from a triarylamine or a diaryl sulfone; X represents N-A, O, S, or Se; A represents an alkyl group or the like; R represent hydrogen, an alkyl group, an aromatic group, or the like; and m+n is an integer of 2 to 4.)
1. A nitrogen-containing aromatic compound, which is represented by formula (1):
in the formula (1), L represents an m+n-valent aromatic hydrocarbon group having 6 to 30 carbon atoms or aromatic heterocyclic group having 3 to 30 carbon atoms and free of a fused heterocycle having 4 or more rings, a group arising from a triarylamine having 9 to 30 carbon atoms, or a group arising from a diaryl sulfone having 6 to 24 carbon atoms, X's each represent N-A, O, S, or Se, A's each independently represent an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an ally group having 2 to 30 carbon atoms, a silyl group having 3 to 18 carbon atoms, an acyl group having 2 to 19 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, or an aromatic heterocyclic group having 3 to 50 carbon atoms and free of a fused heterocycle having 4 or more rings, R's each independently represent hydrogen, an alkyl group having 1 to 30 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an ally group having 2 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or an aromatic heterocyclic group having 3 to 30 carbon atoms and free of a fused heterocycle having 4 or more rings, m represents an integer of 1 to 4, n represents an integer of 0 to 3, and a sum of the m and the n is 2 to 4.
2. A nitrogen-containing aromatic compound according to claim 1 , wherein the n in formula (1) represents 0.
3. A nitrogen-containing aromatic compound. according to claim 1 , wherein the X's in formula (1) each represent N-A.
4. A compound according to claim 1 , wherein the m in formula (1) represents 2 or 3.
5. An organic semiconductor material, comprising the nitrogen-containing aromatic compound according to claim 1 .
6. An organic semiconductor thin film, which is formed of the organic semiconductor material according to claim 5 .
7. An organic electronic device, which is obtained, by using the organic semiconductor material according to claim 5 .
8. An organic electronic device according to claim 7 , wherein the organic electronic device is selected from a light-emitting device, a thin-film transistor, and a photovoltaic device.
9. An organic electronic device according to claim 8 , wherein the light-emitting device comprises an organic electroluminescence device.
10. An organic semiconductor material, comprising the nitrogen-containing aromatic compound according to claim 2 .
11. An organic semiconductor material, comprising the nitrogen-containing aromatic compound according to claim 3 .
12. An organic semiconductor material, comprising the :nitrogen-containing aromatic compound according to claim 4 .
13. An organic semiconductor thin film, which is formed of the organic semiconductor material according to claim 10 .
14. An organic semiconductor thin film, which is formed of the organic semiconductor material according to claim 11 .
15. An organic semiconductor thin film, which is formed of the organic semiconductor material according to claim 12 .
16. An organic electronic device, which is obtained by using the organic semiconductor material according to claim. 10 .
17. An organic electronic device, which is obtained by using the organic semiconductor material according to claim 11 .
18. An organic electronic device, which is obtained by using the organic semiconductor material according to claim 12 .
19. An organic electronic device according to claim 16 , wherein the organic electronic device is selected from a light-emitting device, a thin-film transistor, and a photovoltaic device.
20. An organic electronic device according to claim 17 , wherein the organic electronic device is selected from a light-emitting device, a thin-film transistor, and a photovoltaic device.
21. An organic electronic device according to claim 18 , wherein the organic electronic device is selected from a light-emitting device, a thin-film transistor, and a photovoltaic device.
22. An organic electronic device according to claim 19 , wherein the light-emitting device comprises an organic electroluminescence device.
23. An organic electronic device according to claim 20 , where the light-emitting device comprises an organic electroluminescence device.
24. An organic electronic device according to claim 21 , wherein the light-emitting device comprises an organic electroluminescence device.