BIBENZOTHIOPHENE DERIVATIVES

• US 20090292130A1
• Filed: 05/20/2008
• Published: 11/26/2009
• Est. Priority Date: 05/20/2008
• Status: Active Grant

• Current Assignee: The United States Of America As Represented By The Secretary Of The Army
• Original Assignee: The United States of America As Represented By The Secretary of Agriculture
• Inventors: Forsythe, Eric W., Morton, David C., Shi, Jianmin
• Granted Patent: US 7,964,741 B2
• Time in Patent Office: Days
• US Class Current: 549/41
• CPC Class Codes: C07D 345/00 Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
• CPC Class Codes: C07D 495/06 Peri-condensed systems

Abstract

Compounds containing bibenzochalcogenophene structures are provided in which the chalcogenide is sulfur, selenium, or tellurium. The compounds are characterized by planarity, rigid conjugation structure and high charge mobility making them useful as organic semiconductor in optical devices, electronic devices and integrated devices like organic field effect transistors (OFET) for thin film transistor liquid crystal display (LCD), electrophoretic display such as electronic paper, organic light emitting diode (OLED) for flat panel displays, organic radio frequency identification (ORFID) tags, organic photovoltaic (OPV), sensor devices, and analog and digital electronics.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein R in each occurrence C₁-C₄₈ alkyl, C₆-C₈ cycloalkyl, C₁-C₄₈ alkenyl, C₆-C₈ cycloalkenyl, C₂-C₄₈ alkynyl, C₄-C₄₈ aryl, or C₄-C₄₈ aryl containing the heteroatom.

3. The compound of claim 1, wherein R is in each occurrence C₁-C₄₈ fluoro alkyl, C₆-C₈ fluoro cycloalkyl, C₂-C₄₈ fluoro alkenyl, C₆-C₈ fluoro cycloalkenyl, C₂-C₄₈ fluoro alkynyl, C₄-C₄₈ fluoro aryl, C₄-C₄₈ fluoro aryl containing the heteroatom;

C₁-C₄₈ perfluoro alkyl, C₆-C₈ perfluoro cycloalkyl, C₂-C₄₈ perfluoro alkenyl, C₆-C₈ cycloperfluoro alkenyl, C₂-C₄₈ perfluoro alkynyl, C₄-C₄₈ perfluoro aryl, or C₄-C₄₈ perfluoro aryl containing the heteroatom.

4. The compound of claim 1, wherein R is in at least one occurrence the C₄-C₄₈ heteroatom containing aryl of:

5. The compound of claim 1, wherein G is in every occurrence the same and one of fluorine, chlorine or bromine.

6. The compound of claim 5, wherein G is in every occurrence

7. The compound of claim 6, wherein there is only a single Q per

8. The compound of claim 1, wherein n is 1 and R and G are such that the compound is:

9. The compound of claim 1, wherein said compound is:

10. The compound of claim 1, wherein R and G are such that the compound is:

11. The compound of claim 1, wherein R and G are such that the compound is:

12. The compound of claim 1, wherein R and G are such that the compound is:

13. The compound of claim 1, wherein R and G are such that the compound is:

14. The compound of claim 1, wherein R and C are such that the compound is:

15. The compound of claim 1, wherein R and G are such that the compound is:

16. The compound of claim 1, wherein R and C are such that the compound is:

17. The compound of claim 1, wherein R and C are such that the compound is: