Organic semiconductor device and its production method, and compound
An organic semiconductor device which has an organic semiconductor layer formed by crystallizing a compound represented by the following formula (1) from a solution of the compound: wherein X 1 , X 2 and X 3 represent O, S, Se or Te; at least one of R 1 , R 2 , R 3 and R 4 represents a group that has both an aromatic ring to form a π-conjugated system with the skeleton to which it bonds, and a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20, and the remaining ones represent a hydrogen atom or a substituent.
1. An organic semiconductor device which has an organic semiconductor layer formed by crystallizing a compound represented by the following formula (1) from a solution of the compound:
wherein X 1 , X 2 and X 3 each independently represent an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom; at least one of R 1 , R 2 , R 3 and R 4 represents a group that has both an aromatic ring to form a π-conjugated system with the skeleton to which it bonds, and a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20, and the remaining ones each independently represent a hydrogen atom or a substituent; R 1 and R 2 may bond to each other to form a cyclic structure, and R 3 and R 4 may bond to each other to form a cyclic structure.
2. The organic semiconductor device according to claim 1 , wherein the organic semiconductor layer is formed by crystallizing a compound represented by the following formula (2) from a solution of the compound:
wherein X 1 , X 2 and X 3 each independently represent an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom; R 1 and R 3 each independently represent a hydrogen atom or a substituent; at least one of R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 21 and R 25 represents a group having a chainlike structure of which the number of the atoms of the main chain is from 4 to 20, and the remaining ones each independently represent a hydrogen atom or a substituent.
3. The organic semiconductor device according to claim 2 , wherein the group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20 has a structure represented by the following formula (5):
H—(CH 2 ) m —Ar— (5)
wherein Ar represents an aromatic linking group; and m indicates an integer of from 4 to 20.
4. The organic semiconductor device according to claim 2 , wherein the group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20 has a structure represented by the following formula (6):
H—(CH 2 ) m O—Ar— (6)
wherein Ar represents an aromatic linking group; and m indicates an integer of from 4 to 20.
5. The organic semiconductor device according to claim 2 , wherein at least one of R 13 and R 23 is a group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20.
6. The organic semiconductor device according to claim 2 , wherein at least one of R 13 and R 23 is a group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 8 to 20.
7. The organic semiconductor device according to claim 1 , wherein X 1 , X 2 and X 3 are the same atoms.
8. The organic semiconductor device according to claim 7 , wherein X 1 , X 2 and X 3 are sulfur atoms.
9. The organic semiconductor device according to claim 1 , wherein X 1 and X 3 are sulfur atoms and X 2 is a selenium atom or a tellurium atom.
10. The organic semiconductor device according to claim 1 , which is a field-effect transistor.
11. A method for producing an organic semiconductor device, which comprises forming an organic semiconductor layer by crystallizing a compound represented by the following formula (1) from a solution of the compound:
wherein X 1 , X 2 and X 3 each independently represent an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom; at least one of R 1 , R 2 , R 3 and R 4 represents a group that has both an aromatic ring to form a π-conjugated system with the skeleton to which it bonds, and a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20, and the remaining ones each independently represent a hydrogen atom or a substituent; R 1 and R 2 may bond to each other to form a cyclic structure, and R 3 and R 4 may bond to each other to form a cyclic structure.
12. The method for producing an organic semiconductor device according to claim 11 , wherein the organic semiconductor layer is formed by crystallizing a compound represented by the following formula (2) from a solution of the compound:
wherein X 1 , X 2 and X 3 each independently represent an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom; R 1 and R 3 each independently represent a hydrogen atom or a substituent; at least one of R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 and R 25 represents a group having a chainlike structure of which the number of the atoms of the main chain is from 4 to 20, and the remaining ones each independently represent a hydrogen atom or a substituent.
13. The method for producing an organic semiconductor device according to claim 11 , wherein the solution is a solution in a halogen solvent.
14. The method for producing an organic semiconductor device according to claim 11 , wherein the solvent is an aromatic solvent.
15. A compound having a structure represented by the following formula (2) from a solution of the compound:
wherein X 1 , X 2 and X 3 each independently represent an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom; R 1 and R 3 each independently represent a hydrogen atom or a substituent; at least one of R 11 , R 12 , R 13 , R 14 , R 15 , R 21 , R 22 , R 23 , R 24 and R 25 represents a group having a chainlike structure of which the number of the atoms of the main chain is from 4 to 20, and the remaining ones each independently represent a hydrogen atom or a substituent.
16. A compound according to claim 15 , wherein the group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20 has a structure represented by the following formula (5):
H—(CH 2 ) m —Ar— (5)
wherein Ar represents an aromatic linking group; and m indicates an integer of from 4 to 20.
17. The compound according to claim 15 , wherein the group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20 has a structure represented by the following formula (6):
H—(CH 2 ) m —Ar— (6)
wherein Ar represents an aromatic linking group; and m indicates an integer of from 4 to 20.
18. The compound according to claim 15 , wherein at least one of R 13 and R 23 is a group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 4 to 20.
19. The compound according to claim 15 , wherein at least one of R 13 and R 23 is a group having a chainlike structure in which the number of the carbon atoms constituting the main chain is from 8 to 20.
20. The compound according to claim 15 , wherein X 1 , X 2 and X 3 are the same atoms.
21. The compound according to claim 20 , wherein X 1 , X 2 and X 3 are sulfur atoms.
22. The compound according to claim 15 , wherein X 1 and X 3 are sulfur atoms and X 2 is a selenium atom or a tellurium atom.
23. An organic semiconductor device comprising the compound of claim 15 .