CONJUGATED COMPOUND, NITROGENATED CONDENSED-RING COMPOUND, NITROGENATED CONDENSED-RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT

• US 20100301314A1
• Filed: 11/27/2008
• Published: 12/02/2010
• Est. Priority Date: 11/30/2007
• Status: Active Grant

• Current Assignee: Sumitomo Chemical Company Limited
• Original Assignee: Osaka University, Sumitomo Chemical Company Limited
• Inventors: Nitani, Masashi, Okabe, Makoto, Aso, Yoshio, Ueda, Masato, Ie, Yutaka
• Granted Patent: US 8,378,338 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: C07D 277/60 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 333/78 condensed with rings other than six-membered or with ring systems containing such rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C09B 3/78 Other dyes in which the anthracene nucleus is condensed with one or more carbocyclic rings
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/001 Pyrene dyes
• CPC Class Codes: H10K 10/484 characterised by the channel regions
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

According to the first invention group there are provided conjugated compounds having two or more groups represented by the following formula (I) or the following formula (II):

wherein one of Ar and Ar′ represents a C6 or greater divalent aromatic hydrocarbon group and the other represents a C4 or greater divalent heterocyclic group, wherein the groups each may have a substituent, with the proviso that the groups as a whole contain no fluorine atoms, R¹ and R² each independently represent a hydrogen atom, a halogen atom or a monovalent group, and Ar″ represents a trivalent aromatic hydrocarbon or trivalent heterocyclic group; when the conjugated compound has two or more groups represented by formula (I), the portion excluding these groups contain no fluorine atoms.

According to the second group of the present invention there are provided nitrogen-containing fused-ring compounds represented by the following formula (α-I):

in formula (α-I), R²¹ and R²² each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z²¹ and Z²² each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix);

wherein R²³, R²⁴, R²⁵ and R²⁶ each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R²³ and R²⁴ may bond together to form a ring, the left side and the right side of the group represented by formula (α-viii) may be interchanged.

Claims

1. A conjugated compound having two or more groups represented by the following formula (I) or formula (II):

6. The conjugated compound according to claim 1, wherein the group represented by formula (II) is a group represented by the following formula (IV):

7. The conjugated compound according to claim 6 having two or more groups represented by formula (IV).

8. The conjugated compound according to claim 7, wherein the conjugated compound having two or more groups represented by formula (IV) is a conjugated compound represented by the following formula (VI):

9. The conjugated compound according to, claim 6, wherein each Z² is a group represented by formula (xii).

10. An organic thin film comprising the conjugated compound according to claim 1.

11. An organic thin-film device comprising the organic thin film according to claim 10.

12. An organic thin-film transistor comprising:

a source electrode and drain electrode;

an organic semiconductor layer that is to serve as a current channel between the electrodes; and

a gate electrode that is to control the level of current flowing through the current channel;

wherein the organic semiconductor layer comprises the organic thin film according to claim 10.

13. An organic solar cell comprising the organic thin film according to claim 10.

14. An optical sensor comprising the organic thin film according to claim 10.

2. The conjugated compound according to claim 2, wherein the group represented by formula (I) is a group represented by the following formula (III):

3. The conjugated compound according to claim 2 having two or more groups represented by formula (III).

4. The conjugated compound according to claim 4, wherein the conjugated compound having two or more groups represented by formula (III) is a conjugated compound represented by the following formula (V):

5. The conjugated compound according to claim 4, wherein at least one group of Ar¹, Ar² and Ar³ is an optionally substituted thienylene group, with the proviso that the group as a whole contains no fluorine atoms.

15. A nitrogen-containing fused-ring compound represented by the following formula (α

-I);

16. The nitrogen-containing fused-ring compound according to claim 15, wherein Z²¹ and Z²² are groups represented by formula (α

-ii).

17. The nitrogen-containing fused-ring compound according to claim 15 represented by the following formula (α

-I-I);

18. The nitrogen-containing fused-ring compound according to claim 15, wherein at least one of R²¹ and R²² is a group represented by the following formula (IV):

24. An organic thin film comprising the nitrogen-containing fused-ring compound according to claim 15.

25. An organic thin-film device comprising the organic thin film according to claim 24.

26. An organic thin-film transistor comprising the organic thin film according to claim 24.

27. An organic solar cell comprising the organic thin film according to claim 24.

28. An optical sensor comprising the organic thin film according to claim 24.

19. A nitrogen-containing fused-ring polymer having a repeating unit represented by the following formula (α

-II);

20. The nitrogen-containing fused-ring polymer according to claim 19, wherein Z²¹ and Z²² are groups represented by formula (α

-ii).

21. The nitrogen-containing fused-ring polymer according to, claim 19 having at least one repeating unit represented by the formula (α

-II) and at least one repeating unit represented by the following formula (α

-III);

[Chemical Formula 15]



Ar²¹

 

 

(α

-III)

in formula (α

-III), Ar²¹ represents a divalent aromatic hydrocarbon or divalent heterocyclic group, which may have a substituent.

22. The nitrogen-containing fused-ring polymer according to claim 21, wherein Ar²¹ is a group represented by the following formula (α

-IV);

23. The nitrogen-containing fused-ring polymer according to claim 22, wherein Z²³ is a group represented by formula (α

-ii).

29. An organic thin film comprising the nitrogen-containing fused-ring polymer according to claim 19.

30. An organic thin-film device comprising the organic thin film according to claim 29.

31. An organic thin-film transistor comprising the organic thin film according to claim 29.

32. An organic solar cell comprising the organic thin film according to claim 29.

33. An optical sensor comprising the organic thin film according to claim 29.