IP Library › Granted Patent US 6,869,699
Granted Patent B2
US 6,869,699 · App. 10/391,176 · Granted Mar 22, 2005

P-type materials and mixtures for electronic devices

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Quick Facts
Patent No.
US 6,869,699
App. No.
10/391,176
Granted
Mar 22, 2005
Kind
B2
Abstract

A p-type mixture for use in an electronic device including a host including a dihydrophenazine compound, and a dopant provided in the host.

Claims (85)

1. A p-type mixture for use in an electronic device, comprising:

a) a host including a nonpolymeric dihydrophenazine compound of the formula:

 wherein:

R 1 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 2 to form 5 or 6 member ring systems;

R 4 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 3 to form 5 or 6 member ring systems;

R 5 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl, substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 6 to form 5 or 6 member ring systems;

R 8 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 7 to form 5 or 6 member ring systems;

R 2 and R 3 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, halogen aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, thioaryl, thioalkyl, or connected to form 5 or 6 member ring systems;

R 6 and R 7 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, halogen, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, thioaryl, thioalkyl, or connected to form 5 or 6 member ring systems;

R 9 and R 10 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl;

wherein one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , is something other than hydrogen; and

b) a dopant provided in the host.

2. The p-type mixture according to claim 1 wherein the dihydrophenazine compound is of the formula:

3. The p-type mixture according to claim 1 wherein the dihydrophenazine compound is of the formula:

4. The p-type mixture according to claim 1 wherein the dihydrophenazine compound is of the formula:

5. The p-type mixture according to claim 1 wherein the dihydrophenazine is of the formula:

6. The p-type mixture according to claim 1 wherein the dihydrophenazine compound is of the formula:

7. The p-type mixture according to claim 1 wherein the dihydrophenazine compound is of the formula:

8. The p-type mixture according to claim 1 wherein the dopant is of the formula:

9. The p-type mixture according to claim 1 wherein the dopant is of the formula:

10. The p-type mixture according to claim 1 wherein the dopant is of the formula:

11. The p-type mixture according to claim 1 wherein the dopant is:

i) iodine (I 2 );

ii) iron (III) chloride (FeCl 3 );

iii) iron (III) fluoride (FeF 3 ); or

iv) antimony (V) chloride (SbCl 5 ).

12. The p-type mixture according to claim 1 wherein the dopant is a material having strong electron withdrawing properties.

13. A p-type mixture for use in an electronic device, comprising:

a) a host including a nonpolymeric dihydrophenazine compound of the formula:

 wherein:

R 1 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino or connected to R 11 to form 5 or 6 member ring systems;

R 4 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino or connected to R 14 to form 5 or 6 member ring systems;

R 5 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl, substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 6 to form 5 or 6 member ring systems;

R 6 and R 7 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, haloge aryl aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, thioaryl, thioalkyl, or connected to form 5 or 6 member ring systems;

R 8 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, or connected to R 7 to form 5 or 6 member ring systems;

R 9 and R 10 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl;

R 11 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl, substituted alkenyl, alkoxy, aryloxy, amino, connected to R 1 to form 5 or 6 member ring systems or connected to R 12 to form 5 or 6 member ring systems;

R 12 and R 13 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, halogen, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, thioarkyl, thioalkyl, or connected to form 5 or 6 member ring systems;

R 14 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, amino, connected to R 4 to form 5 or 6 member ring systems or connected to R 13 to form 5 or 6 member ring systems; and

b) a dopant provided in the host.

14. The p-type mixture according to claim 13 wherein the dopant is of the formula:

15. The p-type mixture according to claim 13 wherein the dopant is of the formula:

16. The p-type mixture according to claim 13 wherein the dopant is of the formula:

17. The p-type mixture according to claim 13 wherein the dopant is:

i) iodine (I 2 );

ii) iron (III) chloride (FeCl 3 );

iii) iron (III) fluoride (FeF 3 ); or

iv) antimony (V) chloride (SbCl 5 ).

18. The p-type mixture according to claim 13 wherein the dopant is a material having strong electron withdrawing properties.

19. A p-type mixture e for use in an electronic device, comprising:

a) a host including a nonpolymeric dihydrophenazine compound of the formula:

 wherein:

R 1 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 4 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 5 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl, substituted alkenyl, alkoxy, aryloxy, or amino;

R 8 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 9 and R 10 are individually hydrogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl; and

b) a dopant provided in the host.

20. The p-type mixture according to claim 19 wherein the dopant is of the formula:

21. The p-type mixture e according to claim 19 wherein the dopant is of the formula:

22. The p-type mixture e according to claim 19 wherein the dopant is of the formula:

23. The p-type mixture e according to claim 19 wherein the dopant is:

i) iodine (I 2 );

ii) iron (III) chloride (FeCl 3 );

iii) iron (III) fluoride (FeF 3 ); or

iv) antimony (V) chloride (SbCl 5 ).

24. The p-type mixture according to claim 19 wherein the dopant is a material having strong electron withdrawing properties.

25. p-type mixture e for use in an electronic device, comprising:

a) a host including a nonpolymeric dihydrophenazine compound of the formula:

 wherein:

R 1 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 4 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 5 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl, substituted alkenyl, alkoxy, aryloxy, or amino;

R 8 is hydrogen, halogen, alkyl of from 1 to 24 carbon atoms, which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl, alkoxy, aryloxy, or amino;

R 9 and R 10 are individually hydrogen, alkyl from 1 to 24 carbon which are branched, unbranched, or cyclic, aryl or substituted aryl of from 5 to 24 carbon atoms, heterocyclic or substituted heterocyclic, alkenyl or substituted alkenyl; and

b) a dopant provided in the host.

26. The p-type mixture according to claim 25 wherein the dopant is of the formula:

27. The p-type mixture according to claim 25 wherein the dopant is of the formula:

28. The p-type mixture according to claim 25 wherein the dopant is of the formula:

29. The p-type mixture according to claim 25 wherein the dopant is:

i) iodine (I 2 );

ii) iron (III) chloride (FeCl 3 );

iii) iron (III) fluoride (FeF 3 ); or

iv) antimony (V) chloride (SbCl 5 ).

30. The p-type mixture according to claim 25 wherein the dopant is a material having strong electron withdrawing properties.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2010
From: EASTMAN KODAK COMPANY
To: GLOBAL OLED TECHNOLOGY LLC
Reel/Frame 023998/0368 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2003
From: KLUBEK, KEVIN P.; LIAO, LIANG-SHENG; VARGAS, J. R.; TANG, CHING W.
To: EASTMAN KODAK COMPANY
Reel/Frame 013889/0718 →