Organic electroluminescent materials and devices
Devices containing novel carbazole-containing compounds are provided. The novel compounds also contain electron donor groups, aryl linkers, and at least one nitrogen heterocycle. These novel organic compounds can exhibit delayed fluorescence in the devices.
1. A compound, having a structure of Formula I:
wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from group consisting of CR 9 and N;
wherein any adjacent R 9 s are optionally joined to form a fused ring;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is N;
wherein L 1 is selected from the group consisting of:
and combinations thereof;
wherein X 1 is O, S, or CRR′;
wherein R, R′ are optionally joined to form a ring;
wherein n 1 is an integer from 1 to 20;
wherein L 1 can be further substituted by a substituent selected from the group consisting of alkyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is
which can be further substituted;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 do not contain an electron acceptor group;
wherein R 9 does not contain an electron donor group;
wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 , wherein R 9 is aryl, which can be further substituted; and
wherein at least one of the following is true:
(i) at least one of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that is
comprises an electron donor group independently selected from the group consisting of:
wherein X and Y are selected from the group consisting of O, S, NR 14 , m is an integer from 1 to 20, n 2 is an integer from 1 to 20, and wherein R 14 is selected from the group consisting of aryl and heteroaryl;
(ii) L 1 is selected from the group consisting of
and combinations thereof; and
(iii) Z 1 , Z 3 , and Z 5 are N.
2. The compound of claim 1 , meets condition (i) is met.
3. The compound of claim 1 , wherein condition (iii) is met.
4. The compound of claim 1 , wherein each of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that meets condition (i), comprises an electron donor group independently selected from the group consisting of:
5. The compound of claim 1 , wherein the compound has the formula:
wherein R 91 and R 92 are aryl, which can be further substituted.
6. The compound of claim 1 , wherein each of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that meets condition (i), comprises an electron donor group independently selected from the group consisting of:
7. The compound of claim 1 , wherein the compound is selected from the group consisting of:
8. The compound of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is
which is not further substituted.
9. The compound of claim 1 , wherein R 3 is
which is further substituted, and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are H.
10. The compound of claim 1 , wherein R 3 is
which is not further substituted, and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are H.
11. A first device comprising a first organic light emitting device, comprising:
an anode;
a cathode; and
an emissive layer, disposed between the anode and the cathode;
wherein the emissive layer comprises a compound having the formula:
wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from group consisting of CR 9 and N;
wherein any adjacent R 9 s are optionally joined to form a fused ring;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is N;
wherein L 1 is selected from the group consisting of:
and combinations thereof;
wherein X 1 is O, S, or CRR′;
wherein R, R′ are optionally joined to form a ring;
wherein n 1 is an integer from 1 to 20;
wherein L 1 can be further substituted by a substituent selected from the group consisting of alkyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is
which can be further substituted;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 do not contain an electron acceptor group;
wherein R 9 does not contain an electron donor group;
wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 , wherein R 9 is aryl, which can be further substituted; and
wherein at least one of the following is true:
(i) at least one of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , and R 8 that is
comprises an electron donor group independently selected from the group consisting of:
wherein X and Y are selected from the group consisting of O, S, NR 14 , m is an integer from 1 to 20, n 2 is an integer from 1 to 20, and wherein R 14 is selected from the group consisting of aryl and heteroaryl;
(ii) L 1 is selected from the group consisting of
and combinations thereof; and
(iii) Z 1 , Z 3 , and Z 5 are N.
12. The first device of claim 11 , wherein condition (i) is met.
13. The first device of claim 11 , wherein each of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that meets condition (i), comprises an electron donor group independently selected from the group consisting of:
14. The first device of claim 11 , wherein the compound has the formula:
wherein R 91 and R 92 are aryl, which can be further substituted.
15. The first device of claim 11 , wherein each of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that meets condition (i), comprises an electron donor group independently selected from the group consisting of:
16. The first device of claim 11 , wherein the compound is selected from the group consisting of:
17. The first device of claim 11 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is
which is not further substituted.
18. The first device of claim 11 , wherein R 3 is
which is not further substituted, and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are H.
19. The first device of claim 11 , wherein the first device is a consumer product 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, vehicles, a large area wall, theater or stadium screen, and a sign.
20. A compound, wherein the compound is