Organic phosphorescent material and organic optoelectronic device
View Patent ↗The invention provides a cyclometallated complex comprising the structure of formula I wherein: M is a d-block transition metal; B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted and optionally fused to one or more other aryl or heteroaryl rings; A is a five- or six-membered heteroaryl ring comprising at least three nitrogen atoms; R 1 is a group other than hydrogen; n is zero or an integer equal to or greater than one; and A and B are optionally fused or linked by one or more covalent bonds. The invention also provides the use of such complexes in optoelectronic devices, and in particular in organic light emitting devices.
1. A luminescent organic light emitting cyclometallated complex comprising the structure of formula I
wherein:
M is a d-block transition metal;
B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted and optionally fused to one or more other aryl or heteroaryl rings;
A is triazole or tetrazole;
R 1 is a group other than hydrogen;
n is zero or an integer equal to or greater than one; and
A and B are optionally fused or linked by one or more covalent bonds, and wherein the complex is capable of emitting light having a blue color.
2. A cyclometallated complex according to claim 1 wherein B is a five-membered ring.
3. A cyclometallated complex according to claim 2 wherein B is selected from the group consisting of thiophene, furan and pyrrole.
4. A cyclometallated complex according to claim 1 wherein B is a six-membered ring.
5. A cyclometallated complex according to claim 4 wherein B is selected from the group consisting of benzene, pyridine, pyrazine and pyrimidine.
6. A cyclometallated complex according to claim 1 wherein M is selected from the group consisting of iridium, rhodium, palladium, platinum, gold, osmium and ruthenium.
7. A cyclometallated complex according to claim 6 wherein M is selected from the group consisting of iridium and platinum.
8. A cyclometallated complex according to claim 1 wherein n is greater than or equal to one and at least one group R 1 is an electron-donating group.
9. A cyclometallated complex according to claim 8 wherein n is greater than one.
10. A cyclometallated complex according to claim 8 wherein said electron-donating group is selected from the group consisting of alkylamino, arylamino, alkyl, alkoxy, aryl and carbazole groups.
11. A cyclometallated complex according to claim 1 wherein said ring B is substituted with at least one electron-withdrawing group.
12. A cyclometallated complex according to claim 11 wherein said electron-withdrawing group is selected from the group consisting of halogen atoms, haloalkyl groups, sulfoxides and sulfones.
13. A cyclometallated complex according to claim 12 wherein said electron-withdrawing group is selected from fluorine or perfluorinated C 1-6 haloalkyl groups.
14. A cyclometallated complex according to claim 1 wherein A comprises a triazole group substituted with at least one group R 1 which is an electron donating group, B comprises a phenyl group substituted with at least one fluorine or fluorinated group and said d-block transition metal is iridium.
15. A cyclometallated complex according to claim 1 wherein ring A is substituted with at least one group R 1 which is a dendron.
16. A cyclometallated complex according to claim 1 wherein ring B is substituted with at least one dendron.
17. A cyclometallated complex according to claim 1 wherein ring A is substituted with at least one group R 1 which is a dendron or ring B is substituted with at least one dendron, wherein said dendron comprises a carbazole moiety or a triarylamine moiety.
18. A polymer comprising a luminescent organic light emitting cyclometallated complex according to claim 1 , wherein the complex is incorporated in a main chain or a side chain of the polymer.
19. A polymer comprising a luminescent organic light emitting cyclometallated complex comprising the structure of formula III:
wherein M is a d-block transition metal, A is a triazole or tetrazole which is optionally substituted or fused, B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted or fused, n is zero or greater than one and R 1 is a substituent other than hydrogen, wherein the complex is capable of emitting light having a blue color, and wherein the complex is incorporated in a main chain or a side chain of the polymer.
20. A polymer according to claim 18 wherein said polymer further comprises a carbazole or triarylamine group.
21. An optoelectronic device comprising a luminescent organic light emitting cyclometallated complex according to claim 1 .
22. An organic light emitting device comprising a luminescent organic light emitting cyclometallated complex according to claim 1 .
23. An organic light-emitting device according to claim 22 and comprising a phosphorescent layer wherein said phosphorescent layer comprises a luminescent organic light emitting cyclometallated complex comprising the structure of formula I
wherein:
M is a d-block transition metal;
B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted and optionally fused to one or more other aryl or heteroaryl rings;
A is triazole or tetrazole;
R 1 is a group other than hydrogen;
n is zero or an integer equal to or greater than one; and
A and B are optionally fused or linked by one or more covalent bonds, and wherein the complex is capable of emitting light having a blue colour.
24. An organic light-emitting device according to claim 22 and comprising a phosphorescent layer, wherein said phosphorescent layer comprises a polymer comprising a luminescent organic light emitting cyclometallated complex comprising the structure of formula I
wherein:
M is a d-block transition metal;
B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted and optionally fused to one or more other aryl or heteroaryl rings;
A is triazole or tetrazole;
R 1 is a group other than hydrogen;
n is zero or an integer equal to or greater than one; and
A and B are optionally fused or linked by one or more covalent bonds, wherein the complex is capable of emitting light having a blue color, and wherein the complex is incorporated in a main chain or a side chain of the polymer.
25. A polymer according to claim 19 wherein said polymer further comprises a carbazole or triarylamine group.
26. A cyclometallated complex according to claim 1 wherein ring A is substituted with at least one group R 1 which is a dendron or ring B is substituted with at least one dendron, wherein said dendron comprises a 1,3,5-substituted phenyl moiety.
27. A luminescent organic light emitting cyclometallated complex comprising the structure of formula II
wherein M is a d-block transition metal, A is triazole or tetrazole which is optionally substituted or fused, B is a five- or six-membered aryl or heteroaryl ring which is optionally substituted or fused, n is greater than one and R 1 is a dendron or a solubilising group, and wherein the complex is capable of emitting light having a blue colour.
28. A cyclometallated complex according to claim 1 which is phosphorescent.