Synthesis of cyclooctatetraene derivatives and their use as electron transporters in organic light emitting diodes

• US 6,350,875 B1
• Filed: 03/23/2001
• Issued: 02/26/2002
• Est. Priority Date: 08/16/1999
• Status: Expired due to Term

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Hong, Haiping, Lu, Ping, Weber, William P.
• Primary Examiner(s): SEAMAN, D MARGARET M
• Application Number:
  US09/816,527
• Publication Number:
  US 20020016474A1
• Time in Patent Office: 340 Days
• Field of Search: 546/173, 546/256, 546/255, 549/23, 549/15, 549/49, 549/59, 558/44, 568/331, 568/631, 570/127, 570/183
• US Class Current: 546/173
• CPC Class Codes: C07C 13/267 with a cyclo-octatriene or cyclo-octatetraene ring
• CPC Class Codes: C07C 13/28 Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
• CPC Class Codes: C07C 2/48 of only hydrocarbons containing a carbon-to-carbon triple bond
• CPC Class Codes: C07C 2601/18 with a ring being at least seven-membered
• CPC Class Codes: C07C 43/215 having unsaturation outside the six-membered aromatic rings
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/008 Triarylamine dyes containing no other chromophores

Abstract

The synthesis of asymmetric tetrasubstituted cyclooctatetraenes (“COTs”) and the use of said compounds in organic light emitting diodes is reported, wherein said COTs represent a class of wide gap electron transporters that are readily deposited in vacuum.

Claims

1. A cyclooctatetraene compound having a chemical structure as represented by the formula selected from the group consisting of:

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of phenyl, naphthyl, thienyl, benzthienyl, quinolinyl and pyridyl, each of which may be unsubstituted or substituted with at least one of lower alkyl, lower alkoxy, trifluoromethyl, halogen, nitro, CN, carbonyl and lower alkyl ester.

2. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted phenyl and substituted phenyl.

3. The cyclooctatetraene compound of claim 2, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are unsubstituted phenyl.

4. The cyclooctatetraene compound of claim 2, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are monosubstituted phenyl.

5. The cyclooctatetraene compound of claim 4, wherein the monosubstituted phenyl is monosubstituted with a methyl.

6. The cyclooctatetraene compound of claim 5, wherein the methyl is in the para-position.

7. The cyclooctatetraene compound of claim 4, wherein the monosubstituted phenyl is monosubstituted with a methoxy.

8. The cyclooctatetraene compound of claim 4, wherein the monosubstituted phenyl is monosubstituted with a trifluoromethyl.

9. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted naphthyl and substituted naphthyl.

10. The cyclooctatetraene compound of claim 9, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted β

-naphthyl and substituted β

-naphthyl.

11. The cyclooctatetraene compound of claim 9, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are unsubstituted naphthyl.

12. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted thienyl and substituted thienyl.

13. The cyclooctatetraene compound of claim 12, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted 3-thienyl and substituted 3-thienyl.

14. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted pyridyl and substituted pyridyl.

15. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted quinolinyl and substituted quinolinyl.

16. The cyclooctatetraene compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are selected from the group consisting of unsubstituted benzthienyl and substituted benzthienyl.

17. A cyclooctatetraene compound having a chemical structure as represented by the formula selected from the group consisting of:

wherein R is selected from the group consisting of a hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halogen, nitro, CN, carbonyl and lower alkyl ester.

18. The cyclooctatetraene compound of claim 17, wherein R is a lower alkyl.

19. The cyclooctatetraene compound of claim 18, wherein the lower alkyl is a methyl.

20. The cyclooctatetraene compound of claim 19, wherein the methyl is in the para-position.

21. The cyclooctatetraene compound of claim 17, wherein R is a hydrogen.

22. The cyclooctatetraene compound of claim 17, wherein R is a lower alkoxy.

23. The cyclooctatetraene compound of claim 22, wherein the lower alkoxy is a methoxy.

24. The cyclooctatetracne compound of claim 17, wherein R is a trifluoromethyl.

25. The cyclooctatetraene compound of claim 17, wherein R is a halogen.

26. The cyclooctatetraene compound of claim 17, wherein R is a nitro.

27. A cyclooctatetraene derivative formed as a tetramer of a single monomer wherein the monomer is selected from the group consisting of diphenylbutadiyne, di-p-tolylbutadiyne, di-p-methoxyphenylbutadiyne, bis-(b-naphthyl)butadiyne, bis(3-thienyl)butadiyne and bis(4-trifluoromethylphenyl)butadiyne.