IP Library Granted Patent US 6,849,348
Granted Patent B2
US 6,849,348 · App. 10/334,359 · Granted Feb 1, 2005

Complex fluorene-containing compounds

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Quick Facts
Patent No.
US 6,849,348
App. No.
10/334,359
Granted
Feb 1, 2005
Kind
B2
Abstract

An organic compound comprising a complex fluorene structure represented by one of the following formulas: wherein: X 1 , X 2 , X 3 , and X 4 are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

Claims (33)

1. An organic compound comprising a complex fluorene structure represented by one of the following formulas:

wherein:

X 1 , X 2 , X 3 , and X 4 for formulas I and II include carbon atoms and at least one nitrogen atom; R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

2. The organic compound having a complex fluorene structure of claim 1 is a molecule or a polymer or mixture thereof.

3. An electroluminescent material comprising one or more organic compounds having a complex fluorene structure of claim 1 .

4. An electroluminescent device comprising one or more active layers, wherein at least one of these active layers comprises one or more orgamc compounds having a complex fluorene structure of claim 1 .

5. An organic compound comprising a complex fluorene structure represented by one of the following formulas:

wherein:

X 1 , X 2 , X 3 , and X 4 for formulas I and II are individually the same or different and include a moiety containing CH or N; R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings and wherein the organic compound has a complex fluorene structure represented by formula (IV)

wherein Y 1 and Y 2 are each individually represented as a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or heteroaryl, and y 1 and y 2 are integers from 1 to 6, and wherein Y 1 and Y 2 are the same or different.

6. An electroluminescent material comprising one or more organic compounds having a complex fluorene structure of claim 5 .

7. An electroluminescent device comprising one or more active layers, wherein at least one of these active layers comprises one or more organic compounds having a complex fluorene structure of claim 5 .

8. An organic molecular compound comprising a complex fluorene structure represented by the formula:

wherein:

X 1 , X 2 , X 3 , and X 4 are individually the same or different and include a moiety containing CH or N, and X 1 , X 2 , X 3 , and X 4 include at least one moiety containing CH and one moiety containing N; R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

9. An electroluminescent device comprising one or more active layers, wherein at least one of these active layers comprises one or more organic compounds having a complex fluorene structure of claim 8 .

10. An electroluminescent material comprising one or more organic compounds having a complex fluorene structure of claim 8 .

11. An organic polymeric compound containing a complex fluorene structure represented by the formula:

wherein:

X 1 , X 2 , X 3 , and X 4 are individually the same or different and include a moiety containing CH or N, and R 1 , R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

12. An electroluminescent material comprising one or more organic compounds having a complex fluorene structure of claim 11 .

13. An electroluminescent device comprising one or more active layers, wherein at least one of these active layers comprises one or more organic compounds having a complex fluorene structure of claim 11 .

14. The organic compound having a complex fluorene structure of claim 11 is a polymer represented by repeating units of formula (VII) or (VIII)

wherein:

X 5 and X 6 are linking groups, Y 1 and Y 2 are each individually represented as a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or heteroaryl or other conjugated groups, x, y 1 and y 2 are integers from 0 to 6, and wherein Y 1 and Y 2 are the same or different.

15. An organic polymeric compound comprising a complex fluorene structure represented by one of the following formulas:

wherein:

X 1 , X 2 , X 3 , and X 4 for formulas I, and II are individually the same or different and include a moiety containing CH or N; R,, R 2 , R 3 , and R 4 are substituents each being individually hydrogen, or alkyl, or alkenyl, or alkynyl, or alkoxy of from 1 to 40 carbon atoms; aryl or substituted aryl of from 6 to 60 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 60 carbons; or F, Cl, or Br; or a cyano group; or a nitro group; or R 3 , or R 4 or both are groups that form fused aromatic or heteroaromatic rings.

16. An electroluminescent material comprising one or more organic compounds having a complex fluorene structure of claim 15 .

17. An electroluminescent device comprising one or more active layers, wherein at least one of these active layers comprises one or more organic compounds having a complex fluorene structure of claim 15 .

18. The organic compound having a complex fluorene structure of claim 15 is a polymer represented by repeating units of formula (V) or (VI)

wherein:

X 5 and X 6 are linking groups, Y 1 and Y 2 are each individually represented as a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or heteroaryl, x, y 1 and y 2 are integers from 0 to 6, and wherein Y 1 and Y 2 are the same or different.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2010
From: EASTMAN KODAK COMPANY
To: GLOBAL OLED TECHNOLOGY LLC
Reel/Frame 023998/0368 →