Claims
- 1. A photoactive electronic device comprising:
(a) an anode; (b) a cathode, said cathode having a work function energy level E3; (c) a photoactive layer positioned between said anode and said cathode, said photoactive layer comprising a cyclometalated complex of a transition metal, said cyclometalated complex having a LUMO energy level E2 and a HOMO energy level E4; and (d) an electron transport and/or anti-quenching layer positioned between said cathode and said photoactive layer, said electron transport and/or anti-quenching layer having a LUMO energy level E1 and a HOMO energy level E5, with the proviso that: (1) E1−E3<1V, (2) E1−E2>−1V, and (4) E4−E5>−1V.
- 2. The device of claim 1 wherein E1−E2>0.
- 3. The device of claim 1 wherein E4−E5>0.
- 4. The device of claim 1 wherein said electron transport and/or anti-quenching layer has an electron mobility of at least 10−7 cm2/(V·sec).
- 5. The device of claim 1 wherein the electron transport and/or anti-quenching layer comprises a phenanthroline derivative.
- 6. The device of claim 5 wherein the phenanthroline derivative has Formula II shown in FIG. 4, 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; and 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.
- 7. The device of claim 6, wherein n is an integer from 1 through 12.
- 8. The device of claim 5 wherein the phenanthroline derivative is selected from Formulae II(a) through II(i) in FIG. 5.
- 9. The device of claim 5 wherein the phenanthroline derivative has Formula III(a), shown in FIG. 6, 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; p is 0 or 1; and x is 0 or an integer from 1 through 3.
- 10. The device of claim 9, wherein:
m is an integer from 2 through 10; n is in integerfrom 1 through 12; and with the proviso that when Q is a single bond, p is 0.
- 11. The device of claim 5, wherein the phenanthroline derivative has Formula III(b), shown in FIG. 6, 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; p is 0 or 1; and x is 0 or an integer from 1 through 3.
- 12. The device of claim 1 wherein the electron transport and/or anti-quenching layer comprises a quinoxaline derivative.
- 13. The device of claim 12 wherein the quinoxaline derivative has Formula V, shown in FIG. 8, wherein:
R4 and R5 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylenearyl, alkenylaryl, alkynylaryl, alkyleneheteroaryl, alkenylheteroaryl, alkynylheteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd, or both of R5 together may constitute an arylene or heteroarylene group; a, b, c, and d are 0 or an integer such that a+b=2n+1, and c+d=5; n is an integer; and w is 0 or an integer from 1 through 4.
- 14. The device of claim 13 wherein n is an integer from 1 through 12.
- 15. The device of claim 12 wherein the quinoxaline derivative is selected from Formulae V(a), V(b), V(d) through V(i) and V(k) through V(ag) in FIG. 9.
- 16. The device of claim 12, wherein the quinoxaline derivative is selected from Formulae V(c) and V(j) in FIG. 9.
- 17. The device of claim 12 wherein the quinoxaline derivative has Formula VI, shown in FIG. 10, wherein:
R4 and R5 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylenearyl, alkenylaryl, alkynylaryl, alkyleneheteroaryl, alkenylheteroaryl, alkynylheteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd, or both of R5 together may constitute an arylene or heteroarylene group; 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; a, b, c, and d are 0 or an integer such that a+b=2n+1, and c+d=5; m is an integer equal to at least 2; n is an integer; and p is 0 or 1.
- 18. The device of claim 17, wherein:
m is an integer from 2 through 10; n is an integer from 1 through 12; and p is 0.
- 19. The device of claim 12 wherein the quinoxaline derivative is selected from Formulae VI(b) through VI(g) and VI(i) through VI(k) in FIG. 11.
- 20. The device of claim 12 wherein the quinoxaline derivative is selected from Formulae VI(a), VI(h), VI(l) and VI(m) in FIG. 11.
- 21. The device of claim 12, wherein the quinoxaline derivative has Formula VI(m) shown in FIG. 11.
- 22. The device of claim 12 wherein the quinoxaline derivative has Formula VII, shown in FIG. 12, wherein:
R4 and R5 are the same or different at each occurrence and are selected from H, F, Cl, Br, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylenearyl, alkenylaryl, alkynylaryl, alkyleneheteroaryl, alkenylheteroaryl, alkynylheteroaryl, CnHaFb, OCnHaFb, C6HcFd, and OC6HcFd, or both of R5 together may constitute an arylene or heteroarylene group; 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; a, b, c, and d are 0 or an integer such that a+b=2n+1, and c+d=5; m is an integer equal to at least 2; n is an integer; and p is 0 or 1.
- 23. The device of claims 1-22, wherein the device is a light-emitting diode, a light-emitting electrochemical cell, or a photodetector.
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority from U.S. Provisional Application Serial No. 60/394,767, filed Jul. 10, 2002, and U.S. Provisional Application Serial No. 60/458,277, filed Mar. 28, 2003.
Provisional Applications (2)
|
Number |
Date |
Country |
|
60397767 |
Jul 2002 |
US |
|
60458277 |
Mar 2003 |
US |