Claims
- 1. A composition comprising a phenanthroline derivative having Formula I, shown in FIG. 1, wherein:
R1 and R2 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd; a, b, c, and d are 0 or an integer such that a+b=2n+1, and c+d=5, n is an integer; x is 0 or an integer from 1 through 3; y is 0, 1 or 2; with the proviso that there is at least one substituent on an aromatic group selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 2. The composition of claim 1, wherein R1 is selected from phenyl, substituted phenyl, biphenyl, substituted biphenyl, pyridyl, substituted pyridyl, bipyridyl, and substituted bipyridyl.
- 3. The composition of claim 2, wherein R1 is selected from substituted phenyl, substituted biphenyl, substituted pyridyl, substituted bipyridyl having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, CnHaFb, and C6HcFd.
- 4. The composition of claim 1, wherein at least one R1 is selected from substituted phenyl and substituted biphenyl having at least one substituent selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 5. The composition of claim 1, wherein the phenanthroline derivative is selected from Formulae I(b) through I(f) in FIG. 3.
- 6. A composition having a formula selected from Formula II(a) and Formula II(b) in FIG. 2, wherein:
R1 and R2 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd R3 is the same or different at each occurrence and is selected from a single bond and a group selected from alkylene, heteroalkylene, arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene; Q is selected from a single bond and a multivalent group; m is an integer of at least 2; n is an integer; p is 0 or 1,; x is 0 or an integer from 1 through 3; and y is 0, 1, or 2.
- 7. The composition of claim 6 wherein Q is selected from a hydrocarbon group with at least two points of attachment, selected from an aliphatic group, a heteroaliphatic group, an aromatic group, and a heteroaromatic group.
- 8. The composition of claim 7 wherein Q is selected from alkylene groups, heteroalkylene groups, alkenylene groups, heteroalkenylene groups, alkynylene groups, and heteroalkynylene groups.
- 9. The composition of claim 6 wherein Q is selected from single-ring aromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, single-ring heteroaromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, arylamines, silanes and siloxanes.
- 10. The composition of claim 6, wherein Q is selected from Formulae III(a) through III(h) in FIG. 4.
- 11. The composition of claim 6, wherein R1 is selected from phenyl, substituted phenyl, biphenyl, substituted biphenyl, pyridyl, substituted pyridyl, bipyridyl, and substituted bipyridyl.
- 12. The composition of claim 11, wherein R1 is selected from substituted phenyl, substituted biphenyl, substituted pyridyl, and substituted bipyridyl, having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 13. The composition of claim 6, wherein at least one R1 is selected from substituted phenyl and substituted biphenyl having at least one substituent selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 14. The composition of claim 6, wherein R3 is selected from a phenylene and a substituted phenylene.
- 15. The composition of claim 14 having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 16. The composition of claim 6, wherein R3 is selected from an alkylene group having from 1 through 20 carbon atoms.
- 17. The composition of claim 6, wherein there is at least one substituent on an aromatic group selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 18. An electronic device comprising at least one layer that comprises a phenanthroline derivative having Formula I, shown in FIG. 1, wherein:
R1 and R2 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd; a, b, c, and d are 0 or an integer such that a+b=2n+1, and c+d=5; n is an integer; x is 0 or an integer from 1 through 3; y is 0, 1 or 2; with the proviso that there is at least one substituent on an aromatic group selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 19. The device of claim 18, wherein R1 is selected from phenyl, substituted phenyl, biphenyl, substituted biphenyl, pyridyl, substituted pyridyl, bipyridyl, and substituted bipyridyl.
- 20. The device of claim 19, wherein R1 is selected from substituted phenyl, substituted biphenyl, substituted pyridyl, substituted bipyridyl having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, CnHaFb, and C6HcFd.
- 21. The device of claim 18, wherein at least one R1 is selected from substituted phenyl and substituted biphenyl having at least one substituent selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 22. The electronic device of claim 18, wherein the phenanthroline derivative is selected from Formulae I(a) through I(i) in FIG. 3.
- 23. An electronic device comprising at least one layer that comprises a composition having a formula selected from Formula II(a) and Formula II(b) in FIG. 2, wherein:
R1 and R2 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd, R3 is the same or different at each occurrence and is selected from a single bond and a group selected from alkylene, heteroalkylene, arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene; Q is selected from a single bond and a multivalent group; m is an integer equal to at least 2; n is an integer; p is 0 or 1; x is 0 or an integer from 1 through 3; and y is 0, 1, or 2.
- 24. The device of claim 23 wherein Q is selected from a hydrocarbon group with at least two points of attachment, selected from an aliphatic group, a heteroaliphatic group, an aromatic group, and a heteroaromatic group.
- 25. The device of claim 24 wherein Q is selected from alkylene groups, heteroalkylene groups, alkenylene groups, heteroalkenylene groups, alkynylene groups, and heteroalkynylene groups.
- 26. The device of claim 23 wherein Q is selected from single-ring aromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, single-ring heteroaromatic groups, multiple-ring aromatic groups, fused-ring aromatic groups, arylamines, silanes and siloxanes.
- 27. The device of claim 23, wherein Q is selected from Formulae III(a) through III(h) in FIG. 4.
- 28. The device of claim 23, wherein R1 is selected from phenyl, substituted phenyl, biphenyl, substituted biphenyl, pyridyl, substituted pyridyl, bipyridyl, and substituted bipyridyl.
- 29. The device of claim 28, wherein R1 is selected from substituted phenyl, substituted biphenyl, substituted pyridyl, and substituted bipyridyl, having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 30. The device of claim 23, wherein at least one R1 is selected from substituted phenyl and substituted biphenyl having at least one substituent selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 31. The device of claim 23, wherein R3 is selected from a phenylene and a substituted phenylene.
- 32. The device of claim 31 having at least one substituent selected from alkyl, heteroalkyl, aryl, heteroaryl, arylalkylene, heteroarylalkylene, F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 33. The device of claim 23, wherein R3 is selected from an alkylene group having from 1 through 20 carbon atoms.
- 34. The device of claim 23, wherein there is at least one substituent on an aromatic group selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 35. A composition comprising a phenanthroline derivative having Formula II, shown in FIG. 2, wherein:
R2 and R3 are the same or different at each occurrence and are selected from H, alkyl, heteroalkyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd; a, b, c, and d are integers such that a+b=2n+1, and c+d=5, x is 0 or an integer from 1 through 3; y is 0, 1 or 2; with the proviso that there is at least one substituent on an aromatic group selected from F, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd.
- 36. A composition selected from Formula II(a) in FIG. 2, wherein:
Q is selected from a single bond and a multivalent group; m is an integer from 2 through 10; R3 is the same or different at each occurrence and is selected from a single bond and a group selected from alkylene, heteroalkylene, arylene, heteroarylene, arylenealkylene, and heteroarylenealkylene; R1 and R2 are the same or different at each occurrence and are selected from H, alkyl, heteroalkyl, aryl, heteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFdy is 0, 1 or 2. a, b, c, and d are integers such that a+b=2n+1, and c+d=5,
- 37. The composition of claim 36 wherein Q is selected from Formulae III(a) through III(h) in FIG. 4.
- 38. An electronic device comprising at least one layer comprising the composition of any one of claims 35 through 37.
- 39. An electronic device of claims 35 through 37, wherein the device is a light-emitting diode, light-emitting electrochemical cell, or a photodetector.
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority from U.S. Provisional Application Serial No. 60/394767, filed Jul. 10, 2002, and U.S. Provisional Application Serial No. 60/458277, filed Mar. 28, 2003.
Provisional Applications (2)
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Number |
Date |
Country |
|
60394767 |
Jul 2002 |
US |
|
60458277 |
Mar 2003 |
US |