Organic thin film transistor, organic semiconductor thin film, and organic semiconductor material

1. An organic thin film transistor containing a compound represented by the following formula (1) in a semiconductor active layer:

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

2. The organic thin film transistor according to claim 1 , wherein at least one of R 2 , R 3 , R 8 and R 9 represents a substituent represented by the formula (W).

3. The organic thin film transistor according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (2-1) or (2-2):

wherein R 1 , R 3 to R 7 , and R 9 to R 12 each independently represent a hydrogen atom or a substituent; L a and L b each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R a and R b each independently represent a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein R 1 , R 2 , R 4 to R 8 , and R 10 to R 12 each independently represent a hydrogen atom or a substituent; L c and L d each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R c and R d each independently represent a substituted or unsubstituted alkyl group having 6 to 12carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

4. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), R a , R b , R c and R d represent an alkyl group having 6 to 12 carbon atoms.

5. The organic thin film transistor according to claim 3 , wherein in the formula (2-1) or (2-2), R a , R b , R c and R d represent a linear alkyl group having from 6 to 12carbon atoms.

6. The organic thin film transistor according to claim 3 , wherein in formula (2-1) or (2-2), L a , L b , L c and L d represent a single bond.

7. An organic semiconductor material for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

8. A material for an organic thin film transistor, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

9. A coating solution for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

10. A coating solution for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent, and a polymer binder.

11. An organic semiconductor thin film for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent.

12. An organic semiconductor thin film for a non-light emitting organic semiconductor device, containing the compound represented by the following formula (1):

wherein R 1 to R 12 each independently represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the following formula (W), or all of R 1 to R 12 represent a hydrogen atom:

*-L-R  Formula (W)

wherein * represents a position bonded to the naphthobisbenzofuran skeleton; L represents a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R represents a substituted or unsubstituted alkyl group having 6 to 12 carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms:

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L- 11) and (L-12), R′ each independently represent ahydrogen atom or a substituent, and a polymer binder.

13. The organic semiconductor thin film for a non-light emitting organic semiconductor device according to claim 11 which is produced by a solution coating method.

14. The organic thin film transistor according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (2-1) or (2-2):

wherein R 1 , R 3 to R 7 , and R 9 to R 12 each independently represent a hydrogen atom or a substituent; L a and L b each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R a and R b each independently represent a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein R 1 , R 2 , R 4 to R 8 , and R 10 to R 12 each independently represent a hydrogen atom or a substituent; L c and L d each independently represent a single bond, a divalent linking group represented by any one of the following formulae (L-1) to (L-12), or a divalent linking group containing 2 or more divalent linking groups each represented by any one of the following formulae (L-1) to (L-12) bonded to each other; and R e and R d each independently represent a substituted or unsubstituted alkyl group having 2 or more carbon atoms, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms,

wherein in the formulae (L-1) to (L-12), the wavy line represents a position bonded to the naphthobisbenzofuran skeleton, and * represents a position bonded to R in the formula (W); in the formula (L-1), n represents an integer of 1 or more; in the formula (L-10), m represents 4; in the formulae (L-11) and (L-12), m represents 2; and in the formulae (L-2), (L-10), (L-11) and (L-12), R′ each independently represent a hydrogen atom or a substituent,

wherein in the formula (2-1) or (2-2), R a , R b , R c and R d represent a linear alkyl group having from 6 to 12 carbon atoms, and

wherein the number of the substituent other than the substituent represented by the formula (W) in R 1 to R 12 is 0.