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 5-membered or 6-membered aromatic ring;
wherein A 1 , A 2 , B 1 , and B 2 are independently C or 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;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A 2 =N,
(ii) ring A is a 6-membered ring, A 2 =N, and R 1 and R A are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A 2 =N, X A =N, and R 1 is aryl, and
(iv) R 1 and R 2 are linked or fused to each other.
2. The compound of claim 1 , wherein the ligand has the structure:
3. The compound of claim 2 , wherein at least one of R A , R B , R 1 and R 2 includes CD 3 .
4. 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.
5. 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.
6. 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 substituent selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the substituent includes at least one of CD, CD 2 or CD 3 .
7. The compound of claim 1 , wherein A is selected from the group consisting of imidazole, pyrazole, triazole, oxazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, and triazine.
8. The compound of claim 1 , wherein B is selected from the group consisting of benzene, pyridine, furan, pyrrole, and thiophene.
9. The compound of claim 1 , wherein the compound is a homoleptic compound.
10. The compound of claim 1 , wherein the compound is a heteroleptic compound.
11. 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 comprising a ligand having the structure:
wherein A and B may independently represent a 5-membered or 6-membered aromatic ring;
wherein A 1 , A 2 , B 1 , and B 2 are independently C or 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;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A 2 =N,
(ii) ring A is a 6-membered ring, A 2 =N, and R 1 and R A are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A 2 =N, X A =N, and R 1 is aryl, and
(iv) R 1 and R 2 are linked or fused to each other.
12. The device of claim 11 , wherein the organic layer is an emissive layer and the compound is an emitting dopant.
13. The device of claim 12 , wherein the organic layer further comprises a host.
14. 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 5-membered or 6-membered aromatic ring;
wherein A 1 , A 2 , B 1 , and B 2 are independently C or 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;
wherein the ligand is coordinated to Pt; and
at least one of the following is true:
(i) ring A is a 5-membered aromatic ring and A 2 =N,
(ii) ring A is a 6-membered ring, A 2 =N, and R 1 and R A are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl,
(iii) A 2 =N, X A =N, and R 1 is aryl, and
(iv) R 1 and R 2 are linked or fused to each other.
15. The consumer product of claim 14 , wherein the consumer product is selected from the group consisting of flat panel displays, computer 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, vehicles, a wall, theater or stadium screen, and a sign.
16. The compound of claim 1 , wherein ring A is 5-membered aromatic ring and A 2 =N.
17. The compound of claim 1 , wherein ring A is a 6-membered ring,
wherein A 2 =N; and
wherein R 1 and R A are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, and alkynyl.
18. The compound of claim 1 , wherein A 2 =N, X A =N, and R 1 is aryl.
19. The compound of claim 1 , wherein R 1 and R 2 are linked or fused to each other.