Platinum complex and organic light-emitting device using the same
View Patent ↗The present invention relates to a platinum complex as the following formula (I): wherein X, n, R 1 , R 2 , R 3 ,R 4 , R 5 , X 1 , X 2 , L 1 , and L 2 are defined the same as the specification. The present invention also further provides an organic light-emitting device using the same. The complexes of the present invention exhibit enhanced emission quantum yields, and short phosphorescence radiative lifetimes in the range of several microseconds so as to be applied in high efficiency OLEDs.
1. A platinum complex of the following formula (I):
wherein
X is a counter ion;
n is 0 or 1;
X 1 and X 2 independently are C or N;
R 1 , R 2 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
when X 1 is C;
R 1 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, and R 2 is omitted, when X 1 is N;
R 4 is H and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 4 and R 5 together are C4-C8 alkylene or bridged carbocyclic C4-C12 alkylene, when X 2 is C;
R 4 is omitted and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, when X 2 is N; and
L 1 and L 2 each are
when n is 1, or together are
when n is 0, wherein X 3 is C or N; R 6 and R 7 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 8 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; X 4 and X 5 independently are C or N; each R′ independently is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; X 6 and X 7 independently are C or N; R 9 is H and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 9 and R 10 together are C4-C8 alkylene or bridged carbocyclic C4-C12 alkylene, when X 6 is C; R 9 is omitted and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, when X 6 is N; R 11 , R 12 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
when X 7 is C; and R 11 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl and R 12 is omitted, when X 7 is N.
2. The platinum complex as claimed in claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 and X 7 each are C.
3. The platinum complex as claimed in claim 1 , wherein R 4 is H and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 4 and R 5 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
4. The platinum complex as claimed in claim 3 , wherein R 14 , R 15 , and R 16 each are methyl.
5. The platinum complex as claimed in claim 1 , wherein R 1 , R 2 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 4 is H; and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl.
6. The platinum complex as claimed in claim 5 , wherein R 5 is C1-C4 perfluoroalkyl.
7. The platinum complex as claimed in claim 6 , wherein R 5 is CF 3 .
8. The platinum complex as claimed in claim 1 , wherein R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
R 4 and R 5 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
9. The platinum complex as claimed in claim 1 , wherein R 9 is H and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 9 and R 10 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
10. The platinum complex as claimed in claim 9 , wherein R 14 , R 15 , and R 16 each are methyl.
11. The platinum complex as claimed in claim 1 , wherein R 11 , R 12 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 9 is H; and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl.
12. The platinum complex as claimed in claim 11 , wherein R 10 is C1-C4 perfluoroalkyl.
13. The platinum complex as claimed in claim 12 , wherein R 10 is CF 3 .
14. The platinum complex as claimed in claim 1 , wherein R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
R 9 and R 10 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
15. The platinum complex as claimed in claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 and X 7 each are C; R 1 , R 2 and R 3 independently are H or C1-8 alkyl, R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
R 4 is H and R 5 is C1-C4 perfluoroalkyl, or R 4 and R 5 together are
R 6 and R 7 each are H or C1-C8 alkyl; R 8 is H or C1-8 alkyl; each R′ independently is H or C1-C8 alkyl; R 9 is H and R 10 is C1-C4 perfluoroalkyl, or R 9 and R 10 together are
R 11 , R 12 and R 13 independently are H or C1-8 alkyl, R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
and R 14 , R 15 , and R 16 are C1-8 alkyl.
16. The platinum complex as claimed in claim 1 , wherein the platinum complex is
17. An organic light-emitting device, comprising:
an anode;
a cathode; and
one or more organic medium layers including a light-emitting layer disposed between the anode and the cathode,
wherein at least one layer of the organic medium layers comprises a platinum complex of the following formula (I):
wherein
X is a counter ion;
n is 0 or 1;
X 1 and X 2 independently are C or N;
R 1 , R 2 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
when X 1 is C;
R 1 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl and R 2 is omitted, when X 1 is N;
R 4 is H and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 4 and R 5 together are C4-C8 alkylene or bridged carbocyclic C4-C12 alkylene, when X 2 is C;
R 4 is omitted and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, when X 2 is N; and
L1 and L2 each are
when n is 1, or together are
when n is 0, wherein X 3 is C or N; R 6 and R 7 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 8 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; X 4 and X 5 independently are C or N; each R′ independently is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; X 6 and X 7 independently are C or N; R 9 is H and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, or R 9 and R 10 together are C4-C8 alkylene or bridged carbocyclic C4-C12 alkylene, when X 6 is C; R 9 is omitted and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, when X 6 is N; R 11 , R 12 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl, R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
when X 7 is C; and R 11 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl and R 12 is omitted, when X 7 is N.
18. The organic light-emitting device as claimed in claim 17 , wherein the light-emitting layer is made of at least one host material doped with the platinum complex.
19. The platinum complex as claimed in claim 17 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 and X 7 each are C.
20. The platinum complex as claimed in claim 17 , wherein R 1 , R 2 and R 3 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 4 is H; and R 5 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl.
21. The platinum complex as claimed in claim 17 , wherein R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
and R 4 and R 5 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
22. The platinum complex as claimed in claim 17 , wherein R 11 , R 12 and R 13 independently are H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl; R 9 is H; and R 10 is H, C1-C8 alkyl, phenyl, or C1-C4 perfluoroalkyl.
23. The platinum complex as claimed in claim 17 , wherein R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
and R 9 and R 10 together are
and R 14 , R 15 , and R 16 independently are C1-8 alkyl.
24. The platinum complex as claimed in claim 17 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 and X 7 each are C; R 1 , R 2 and R 3 independently are H or C1-8 alkyl, R 1 is H and R 2 and R 3 together are
or R 3 is H and R 1 and R 2 together are
R 4 is H and R 5 is C1-C4 perfluoroalkyl, or R 4 and R 5 together are
R 6 and R 7 each are H or C1-C8 alkyl; R 8 is H or C1-8 alkyl; each R′ independently is H or C1-C8 alkyl; R 9 is H and R 10 is C1-C4 perfluoroalkyl, or R 9 and R 10 together are
R 11 , R 12 and R 13 independently are H or C1-8 alkyl, R 11 is H and R 12 and R 13 together are
or R 13 is H and R 11 and R 12 together are
and R 14 , R 15 , and R 16 are C1-8 alkyl.
25. The organic light-emitting device as claimed in claim 17 , wherein the platinum complex is