Heterocyclic dinaphtho thieno thiophene (DNTT) compounds for use as organic semiconductor thin films in field effect transistors and related methods
Provided are a novel heterocyclic compound represented by formula (1), and a field-effect transistor having a semiconductor layer comprising the aforementioned compound. Also provided is a method for producing an intermediate enabling the production of the aforementioned novel heterocyclic compound. (In the formula, R 1 and R 2 represent a hydrogen atom, a C 2-16 alkyl group or an aryl group. However, when R 1 each independently represents a C 2-16 alkyl group or an aryl group, R 2 represents a hydrogen atom or each independently represents an aryl group; and when R 1 represents a hydrogen atom, R 2 each independently represents an aryl group.)
1. A heterocyclic compound represented by the following formula (1):
(wherein R 1 and R 2 each represent one of a hydrogen atom, a C2-C16 alkyl group, and an aryl group; when R 1 each independently represents a C2-C16 alkyl group or an aryl group, R 2 each represents a hydrogen atom or R 2 each independently represents an aryl group; and when R 1 represents a hydrogen atom, R 2 each independently represents an aryl group).
2. The heterocyclic compound according to claim 1 , wherein in the formula (1), R 1 each independently is a linear C5-C12 alkyl group, and R 2 each is a hydrogen atom.
3. The heterocyclic compound according to claim 1 , wherein in the formula (1), R 1 each independently is an aryl group having one of a phenyl structure, a naphthyl structure, and a biphenyl structure, and R 2 each is a hydrogen atom.
4. The heterocyclic compound according to claim 3 , wherein in the formula (1), R 1 each independently is an aryl group selected from the group consisting of a phenyl group, a 4-alkylphenyl group, a 1-naphthyl group, and a biphenyl group, and R 2 is a hydrogen atom.
5. The heterocyclic compound according to claim 1 , wherein in the formula (1), R 1 is a hydrogen atom, and R 2 each independently is an aryl group having one of a phenyl structure, a naphthyl structure, and a biphenyl structure.
6. The heterocyclic compound according to claim 5 , wherein in the formula (1), R 1 each is a hydrogen atom, and R 2 each independently is an aryl group selected from the group consisting of a phenyl group, a 4-alkylphenyl group, a 1-naphthyl group, and a biphenyl group.
7. An organic semiconductor material comprising one or two or more heterocyclic compounds represented by the formula (1) according to claim 1 .
8. An ink for creating a semiconductor device, comprising one or two or more heterocyclic compounds represented by the formula (1) according to claim 1 .
9. A method for producing an organic thin film, which comprises applying the ink according to claim 8 .
10. A method for producing a field effect transistor, comprising the step of forming an organic thin film on a substrate by the method according to claim 9 .
11. An organic thin film comprising one or two or more heterocyclic compounds represented by the formula (1) according to claim 1 .
12. A field effect transistor comprising an organic thin film according to claim 11 .
13. The field effect transistor according to claim 12 , wherein the field effect transistor is a bottom contact type.
14. The field effect transistor according to claim 12 , wherein the field effect transistor is a top contact type.
15. A method for producing an organic thin film, wherein the organic thin film according to claim 11 is formed by a deposition method.
16. A method for producing a field effect transistor, comprising the step of forming an organic thin film on a substrate by the method according to claim 15 .
17. A method for producing an intermediate compound represented by a formula (4) in production of a heterocyclic compound represented by a formula (2), the method comprising reacting a compound represented by a formula (3) with dimethyl disulfide:
(wherein R 3 represents a substituent);
(wherein R 3 and R 4 represent a substituent).
18. A method for producing an intermediate compound represented by a formula (6) in production of a heterocyclic compound represented by a formula (2), the method comprising reacting a compound represented by a formula (4) with a tin compound represented by a formula (5):
(wherein R 3 , R 4 , and R 5 represent a substituent).