Organic electroluminescent materials and devices
Novel organic compounds comprising ligands with deuterium substitution are provided. In particular, the compound is an iridium complex comprising methyl-d 3 substituted ligands. The compounds may be used in organic light emitting devices to provide devices having improved color, efficiency and lifetime.
1. A compound comprising a ligand having the structure:
wherein A and B may independently represent a 6-membered aromatic ring;
wherein A 1 and B 1 are independently C or N;
wherein A 2 and B 2 is C, and one of A 2 and B 2 is N;
wherein R A and R B may represent mono, di, or tri substitutions;
wherein X A and X B are independently C or a heteroatom;
wherein R A , R B , R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of R A , R B , R 1 and R 2 includes CD, CD 2 or CD 3 , wherein the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein R A , R B , R 1 and R 2 may be linked;
wherein R A , R B , R 1 and R 2 may be fused; and
wherein the ligand is coordinated to Ir.
2. The compound of claim 1 , wherein at least one of the substituents of R A and R B is CD 3 attached directly to ring A, ring B, or a ring that is conjugated or fused to ring A or ring B.
3. The compound of claim 1 , wherein X A and X B are independently C or N and when X A is N, R 1 is aryl.
4. The compound of claim 1 , wherein X A and X B are independently C or N and when X A is N, R 1 is phenyl further substituted with a group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the group includes at least one of CD, CD 2 or CD 3 .
5. The compound of claim 1 , wherein the ligand is selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 may be linked;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 may be fused; and
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 includes an alkyl group that includes CD, CD 2 , or CD 3 .
6. The compound of claim 5 , wherein the ligand has the formula:
7. The compound of claim 5 , wherein the ligand has the formula:
8. The compound of claim 5 , wherein the ligand has the formula:
9. The compound of claim 1 , wherein A is selected from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, and triazine.
10. The compound of claim 1 , wherein B is selected from the group consisting of benzene, pyridine.
11. The compound of claim 1 , wherein the ligand having FORMULA I is a ligand in a homoleptic compound.
12. The compound of claim 1 , wherein the ligand having FORMULA I is a ligand in a heteroleptic compound.
13. An organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound further comprising a ligand having the structure:
wherein A and B may independently represent a 6-membered aromatic ring;
wherein A 1 and B 1 are independently C or N;
wherein A 2 and B 2 is C, and one of A 2 and B 2 is N;
wherein R A and R B may represent mono, di, or tri substitutions;
wherein X A and X B are independently C or a heteroatom;
wherein R A , R B , R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of R A , R B , R 1 and R 2 includes CD, CD 2 or CD 3 , wherein the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein R A , R B , R 1 and R 2 may be linked;
wherein R A , R B , R 1 and R 2 may be fused; and
wherein the ligand is coordinated to Ir.
14. The device of claim 13 , wherein the ligand has the structure:
15. The device of claim 14 , wherein at least one of R A , R B , R 1 and R 2 is CD 3 .
16. The device of claim 13 , wherein at least one of the substituents of R A and R B is CD 3 attached directly to ring A, ring B, or a ring that is conjugated or fused to ring A or ring B.
17. The device of claim 13 , wherein X A and X B are independently C or N and when X A is N, R 1 is aryl.
18. The device of claim 13 , wherein X A and X B are independently C or N and when X A is N, R 1 is phenyl further substituted with a group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the group includes at least one of CD, CD 2 or CD 3 .
19. The device of claim 13 , wherein the ligand is selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 may be linked;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 may be fused; and
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 includes an alkyl group that includes CD, CD 2 , or CD 3 .
20. The device of claim 13 , wherein A is selected from the group consisting of imidazole, pyridine, pyridazine, pyrimidine, pyrazine, and triazine.
21. The device of claim 13 , wherein B is selected from the group consisting of benzene, pyridine.
22. The device of claim 13 , wherein the organic layer is an emissive layer and the compound is an emitting dopant.
23. The device of claim 22 , wherein the organic layer further comprises a host.
24. The device of claim 23 , wherein the host has the formula:
wherein R′ 1 , R′ 3 , R′ 5 , and R′ 6 may represent mono, di, tri, or tetra substitutions;
wherein R′ 2 and R′ 4 may represent mono, di, or tri substitutions; and
wherein each of R′ 1 , R′ 2 , R′ 3 , R′ 4 , R′ 5 , and R′ 6 is independently selected from the group consisting of hydrogen, alkyl and aryl.
25. The device of claim 23 , wherein the host is
26. A consumer product comprising a device, the device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand having the structure:
wherein A and B may independently represent a 6-membered aromatic ring;
wherein A 1 and B 1 are independently C or N;
wherein A 2 and B 2 are independently C, and one of A 2 and B 2 is N;
wherein R A and R B may represent mono, di, or tri substitutions;
wherein X A and X B are independently C or a heteroatom;
wherein R A , R B , R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl;
wherein at least one of R A , R B , R 1 and R 2 includes CD, CD 2 or CD 3 , whereby the deuterium atoms are provided within an alkyl chain or at the end of an alkyl chain;
wherein R A , R B , R 1 and R 2 may be linked;
wherein R A , R B , R 1 and R 2 may be fused; and
wherein the ligand is coordinated to Ir.