Organic electroluminescent materials and devices
A compound having a structure according to formula (I) is disclosed. In formula (I), Cu is a monovalent copper atom; *C is a carbene carbon; X 1 and X 2 are selected from alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, arylalkyl, aryloxy, aryl, heteroalkyl, heteroaryl, and combinations thereof; X 1 is bonded to *C by a C atom, and X 2 is bonded to *C by an N atom; X 1 and X 2 are optionally joined to form a ring; and Y is selected halide, alkyl, cycloalkyl, alkoxy, amino, phosphine, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, arylalkyl, aryloxy, aryl, heteroalkyl, heteroaryl, and combinations thereof. A formulation containing compound having a structure according to formula (I), and a device with an organic layer comprising disposed between an anode and a cathode, that includes a compound having a structure according to formula (I) are also described.
1. A compound comprising a structure according to formula (I):
wherein C* is a carbene carbon, X 1 is bonded to C* by a C atom, and X 2 is bonded to C* by a N atom, and X 1 and X 2 join to form a 5 membered or 6-membered heterocyclic ring A, wherein ring A is optionally substituted with at least one substituent
selected from the group consisting of alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, aryloxy, aryl, heteroalkyl, heteroaryl, and combinations thereof;
and
Y is selected from the group consisting of halide, alkyl, cycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroalkyl, and heteroaryl.
2. The compound of claim 1 , wherein Y includes a carbene carbon that is coordinated to the Cu atom.
3. The compound of claim 1 , wherein the ring A is part of a polycyclic ring system.
4. The compound of claim 1 , wherein Cu—Y comprises a structure selected from the group consisting of:
wherein R is selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, arylalkyl, aryloxy, aryl, heteroalkyl, and heteroaryl.
5. The compound of claim 1 , wherein Cu—Y comprises a structure selected from the group consisting of:
wherein R 1 and R 2 are independently selected from the group consisting of alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, arylalkyl, aryloxy, aryl, heteroalkyl, and heteroaryl.
6. The compound of claim 1 , wherein Y is selected from the group consisting of aryl, heteroalkyl, and heteroaryl.
7. The compound of claim 1 selected from the group consisting of:
wherein z is 2, or 3;
wherein R, R 1 , R 2 , and R 3 , are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, arylalkyl, aryloxy, aryl, heteroalkyl, and heteroaryl.
8. The compound of claim 7 , wherein Y in formula (I) is selected from the group consisting of aryl, heteroalkyl, and heteroaryl.
9. A consumer product including a display, the display including an organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of claim 1 and a host.
10. The product of claim 9 selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, a wall, theater or stadium screen, and a sign.
11. An organic light emitting device that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer is an emissive layer that comprises a compound of claim 1 and a host, the compound being an emissive dopant.
12. An organic light emitting device that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound of claim 1 and a host, the compound being a non-emissive dopant.
13. The device of claim 11 , wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
14. The device of claim 11 , wherein the host is a compound selected from the group consisting of:
and combinations thereof.
15. An organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of claim 7 and a host, wherein the organic layer is an emissive layer.