Organic light emitting devices

1. An electroluminescent device comprising an anode, a cathode, a buffer layer in contact with said anode, and a luminescent region provided between said anode and cathode, said luminescent region comprising;

an electron injection and transporting zone and at least one of a hole injection and transporting zone and a mixed charge transport layer, wherein said electron injection and transporting zone and/or said mixed charge transporting layer comprises an azole compound of the formula (1):

wherein one X represents N and the other X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component.

2. The electroluminescent device of claim 1 , wherein said alkyl group has from 1 to about 6 carbon atoms and said alkoxy group has from 1 to about 6 carbon atoms.

3. The electroluminescent device of claim 1 , wherein said Ar is an aryl group having from about 6 to about 30 carbons or a heteroaryl group.

4. The electroluminescent device of claim 3 , wherein said aryl group is selected from the group consisting of a phenyl, a naphthyl, and an anthryl and said heteroaryl group is selected from the group consisting of a pyridyl and a quinolyl.

5. The electroluminescent device of claim 1 , wherein said electron injection and transporting zone is provided adjacent said cathode.

6. The electroluminescent device of claim 5 , wherein said electron injection and transporting zone comprises one or more layers.

7. The electroluminescent device of claim 6 , wherein at least one of said layers comprises said azole compound of formula I.

8. The electroluminescent device of claim 6 , wherein a portion of one or more of said layers comprises said azole compound of formula I.

9. The electroluminescent device of claim 6 , wherein a layer in direct contact with said cathode comprises said azole compound of formula I.

10. The electroluminescent device of claim 1 , wherein said hole injection and transport zone is provided on said anode, said hole injection and transporting zone comprising compounds selected from the group consisting of aromatic tertiary amines, indolocarbazoles, aromatic hydrocarbons and mixtures thereof.

11. The electroluminescent device of claim 10 , wherein a luminescent material is additionally provided in said hole injection and transporting zone and/or said electron injection and transporting zone.

12. The electroluminescent device of claim 1 , wherein a mixed charge transport layer is provided in between said electron injection and transporting zone and said anode.

13. The electroluminescent device of claim 12 , wherein said mixed charge transport layer comprises an electron transport material and a hole transport material.

14. The electroluminescent device of claim 13 , wherein said mixed charge transport layer comprises about 20 wt % to about 80 wt % of the hole transport material.

15. The electroluminescent device of claim 13 , wherein electron transport material is selected from the group consisting of an azole compound of formula I, metal chelates, stilbenes, triazines, aromatic hydrocarbons and mixtures thereof.

16. The electroluminescent device of claim 12 , wherein said mixed charge transport layer is comprised of a luminescent material.

17. The electroluminescent device of claim 13 , wherein said mixed charge transport layer additionally comprises a luminescent material.

18. The electroluminescent device of claim 1 , wherein said buffer layer comprises a material selected from the group consisting of a phthalocyanine or derivatives thereof, an aromatic tertiary amine, a polyaniline, a polythiophene and mixtures thereof.

19. An electroluminescent device comprising an anode, a cathode and a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone and at least one of a hole injection and transporting zone and a mixed charge transport layer, wherein said electron injection and transporting zone and/or said mixed charge transporting layer comprises an azole compound

selected from the group consisting of 1-methy1-2-(phenyl)imidazo [4,5-f]-[1,10] phenanthroline, 1-methyl-2-(2-pyridyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(1-naphthyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl)imidazo [4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-methyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-t-butyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-naphthyl)imidazo[4,5-f]-[1,10] phenanthroline, 1and mixtures thereof.

20. The electroluminescent device of claim 19 , wherein said azole compound is 1-methyl-2-(9-anthryl)imidazo[4,5-f]-[1,10] phenanthroline.

21. An electroluminescent device comprising an anode, a cathode and a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone and at least one of a hole injection and transporting zone and a mixed charge transport layer, wherein said electron injection and transporting zone and/or said mixed charge transporting layer comprises an azole compound of the formula (II):

wherein R 1 , R 2 , R 3 , R 4 and R 5 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group with from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

R is a hydrocarbyl group of from 1 to about 30 carbons or an aryl group containing about 6 to about 20 carbons.

22. The electroluminescent device of claim 21 , wherein said alkyl for R 2 , R 3 , R 4 and R 5 is selected from the group consisting of methyl, ethyl, propyl and butyl.

23. The electroluminescent device of claim 22 , wherein R 5 905 is an aryl group.

24. The electroluminescent device of claim 23 , wherein said aryl group for R5 is selected from the group consisting of a phenyl, a naphthyl, an anthryl, and a styryl.

25. The electroluminescent device of claim 21 , wherein said electron injection and transporting zone is provided adjacent said cathode.

26. The electroluminescent device of claim 25 , wherein said electron injection and transporting zone comprises one or more layers.

27. The electroluminescent device of claim 26 , wherein at least one of said layers comprises said azole compound of formula II.

28. The electroluminescent device of claim 25 , wherein a portion of one or more of said layers comprises said an azole compound of formula I:

wherein X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component.

29. The electroluminescent device of claim 25 , wherein a layer in direct contact with said cathode comprises said an azole compound of formula I:

wherein X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component.

30. The electroluminescent device of claim 21 , wherein said hole injection and transporting zone is provided on said anode, said hole injection and transporting zone comprising compounds selected from the group consisting of aromatic tertiary amines, indolocarbazoles, aromatic hydrocarbons and mixtures thereof.

31. The electroluminescent device of claim 30 , wherein said hole injection and transporting zone and/or said electron injection and transporting zone additionally comprises a luminescent material.

32. The electroluminescent device of claim 21 , wherein a mixed charge transport layer is provided in between said electron injection and transporting zone and said anode.

33. The electroluminescent device of claim 32 , wherein said mixed charge transport layer comprises an electron transport material and a hole transport material.

34. The electroluminescent device of claim 33 , wherein said mixed charge transport layer comprises about 20 wt % to about 80 wt % of the hole transport material.

35. The electroluminescent device of claim 34 , wherein electron transport material is selected from the group consisting of an azole compound of formula I, metal chelates, stilbenes, triazines, aromatic hydrocarbons and mixtures thereof wherein the azole compound of formula I is:

wherein X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component.

36. The electroluminescent device of claim 32 , wherein said mixed charge transport layer is comprised of a luminescent material.

37. The electroluminescent device of claim 33 , wherein said mixed charge transport layer additionally comprises a luminescent material.

38. The electroluminescent device of claim 21 , wherein a buffer layer is provided in contact with said anode, said buffer layer comprising a material selected from the group consisting of a phthalocyanine or derivatives thereof, an aromatic tertiary amine, a polyaniline, a polythiophene and mixtures thereof.

39. The electroluminescent device of claim 21 , wherein said azole compound is selected from the group consisting of 1-methyl-2-(9-anthryl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-methyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-t-butyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-naphthyl)imidazo [4,5-f]-[1,10] phenanthroline and mixtures thereof.

40. The electroluminescent device of claim 39 , wherein said azole compound is 1-methyl-2-(9-anthryl)imidazo[4,5-f]-[1,10] phenanthroline.

41. An organic electroluminescent device comprising;

an anode and a cathode; and

a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone adjacent said cathode and a hole injection and transporting zone adjacent said anode, wherein said electron injection and transporting zone comprises one or more azole compounds of a formula I and/or formula II,

wherein a compound of formula I comprises:

wherein one X represents N and the other X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons:

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component; and

a compound of formula II comprises:

wherein R 1 , R 2 , R 3 , R 4 and R 5 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group with from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

R is a hydrocarbyl group of from 1 to about 30 carbons or an aryl group containing about 6 to about 20 carbons.

42. The device of claim 41 , wherein said electron injection and transporting zone is provided in direct contact with said cathode.

43. The device of claim 41 , wherein said electron injection and transporting zone comprises one or more layers.

44. An organic electroluminescent device comprising;

an anode and a cathode;

a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone adjacent said cathode and a hole injection and transporting zone adjacent said anode, wherein said electron injection and transporting zone comprises one or more layers, and one or more azole compounds of formula I and/or formula II with at least one of said layers comprising an azole compound of formula II,

wherein a compound of formula I comprises:

wherein one X represents N and the other X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component; and

a compound of formula II comprises:

wherein R 1 , R 2 , R 3 , R 4 and R 5 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group with from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

R is a hydrocarbyl group of from 1 to about 30 carbons or an aryl group containing about 6 to about 20 carbons.

45. The device of claim 43 , wherein a portion of one or more of said layers comprises said azole compound of formula I.

46. The device of claim 45 , wherein a layer in direct contact with said cathode comprises said azole compound of formula I.

47. The device of claim 41 , wherein said hole injection and transporting zone is provided in direct contact with said anode, said hole injection and transporting zone comprising compounds selected from the group consisting of aromatic tertiary amines, indolocarbazoles, aromatic hydrocarbons and mixtures thereof.

48. The device of claim 41 , wherein said hole injection and transporting zone and/or said electron injection and transporting zone additionally comprises a luminescent material.

49. The device of claim 41 , wherein a mixed charge transport layer is provided in between said electron injection and transporting zone and said anode.

50. The device of claim 49 , wherein said mixed charge transport layer comprises an electron transport material and a hole transport material.

51. The device of claim 50 , wherein said mixed charge transport layer comprises about 20 wt % to about 80 wt % of the hole transport material.

52. The device of claim 51 , wherein electron transport material is selected from the group consisting of an azole compound of formula I, metal chelates, stilbenes, triazines, aromatic hydrocarbons and mixtures thereof.

53. The device of claim 49 , wherein said mixed charge transport layer is comprised of a luminescent material.

54. The device of claim 50 , wherein said mixed charge transport layer additionally comprises a luminescent material.

55. The device of claim 41 , wherein said buffer layer comprises a material selected from the group consisting of a phthalocyanine or derivatives thereof, an aromatic tertiary amine, a polyaniline, a polythiophene and mixtures thereof.

56. An organic electroluminescent device comprising:

an anode and a cathode;

a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone adjacent said cathode and a hole injection and transporting zone adjacent said anode, wherein said electron injection and transporting zone comprises one or more azole compounds

is selected from the group consisting of 1-methyl-2-phenyl)imidazo [4,5-f]-[1,10] phenanthroline, 1-methyl-2-(2-pyridyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(1-naphthyl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl)imidazo[4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-methyl) imidazo [4,5-f]-[1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-t-butyl)imidazo[4,5-f]-1,10] phenanthroline, 1-methyl-2-(9-anthryl-10-naphthyl)imidazo[4,5-f]-[1,10] phenanthroline and mixtures thereof.

57. The device of claim 56 , wherein said azole compound is 1-methyl-2-(9-anthryl)imidazo[4,5-f]-[1,10] phenanthroline.

58. A method to reduce power consumption and increase power conversion efficiency in an organic light emitting device comprising an anode, a cathode, a buffer layer in contact with said anode, and a luminescent region provided between said anode and cathode, said luminescent region comprising:

an electron injection and transporting zone and at least one of a hole injection and transporting zone and a mixed charge transport layer,

wherein said method comprises providing an azole compound of a formula I and/or formula II in said electron injection and transporting zone and/or said mixed charge transporting layer, wherein a compound of formula I comprises:

wherein one X represents N and the other X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 1 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component; and

a compound of formula II comprises:

wherein R 1 , R 2 , R 3 , R 4 and R 5 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbons atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group with from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

R is a hydrocarbyl group of from 1 to about 30 carbons or an aryl group containing about 6 to about 20 carbons.

59. An electron transport material comprising an azole compound of the following formula:

wherein R 1 , R 2 , R 3 , R 4 and R 5 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group with from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

R is a hydrocarbyl group of from 1 to about 30 carbons or an aryl group containing about 6 to about 20 carbons.

60. A photoreceptor, solar cell and/or organic electronic device comprising the electron transport material of claim 59 .

61. An electroluminescent device comprising an anode, a cathode, a buffer layer in contact with said anode, and a luminescent region provided between said anode and cathode, said luminescent region comprising;

an electron injection and transporting zone and at least one of a hole injection and transporting zone and a mixed charge transport layer, wherein said electron injection and transporting zone and/or said mixed charge transporting layer comprises an azole compound of formula (I):

wherein X represents CH or N;

Y is an atom or a group selected from the group consisting of O, S, and —N(R)—, wherein R is a hydrocarbyl group of from 8 to about 30 carbons;

R 1 and R 2 are each a substituent selected from the group consisting of hydrogen, an alkyl group of from 1 to about 25 carbon atoms, an aryl group of about 6 to about 30 carbon atoms, an alkoxy group of from 1 to about 25 carbon atoms, a halogen, and a cyano group; and

Ar is an aromatic component.

62. The organic electroluminescent device of claim 41 , further comprising a buffer layer in contact with the anode.