IP Library › Granted Patent US 11,380,854
Granted Patent B2
US 11,380,854 · App. 16/385,637 · Granted Jul 5, 2022

Heteroleptic iridium complexes as dopants

Inventors: Gregg Kottas (Ewing, NJ); Nasrin Ansari (Monmouth Jct., NJ); Zeinab Elshenawy (Holland, PA); Alan DeAngelis (Pennington, NJ); Chuanjun Xia (Lawrenceville, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/025C09K11/06H01L51/0054H01L51/0056H01L51/0058H01L51/0067H01L51/0072H01L51/0074H01L51/50H05B33/14C09K2211/1007C09K2211/1029C09K2211/1088C09K2211/185H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 11,380,854
App. No.
16/385,637
Granted
Jul 5, 2022
Kind
B2
Abstract

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Claims (54)

1. A compound having the formula:

wherein R 1 and R 2 are optionally linked;

wherein the sum of the number of carbon atoms in R 1 and R 2 is at least 2;

wherein R 3 , R 4 , R 5 , and R 6 are optionally linked;

wherein R a and R b represent mono-, di-, tri- or tetra-substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 comprises a moiety selected from the group consisting of partially or fully deuterated alkyl and partially or fully deuterated cycloalkyl, and

wherein n is 1 or 2.

2. The compound of claim 1 , wherein n is 2.

3. The compound of claim 1 , wherein X is O.

4. The compound of claim 1 , wherein at least one of R 1 and R 2 is partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl.

5. The compound of claim 1 , wherein R 1 is partially or fully deuterated alkyl.

6. The compound of claim 1 , wherein R 2 is partially or fully deuterated alkyl.

7. The compound of claim 1 , wherein R 1 or R 2 are independently selected from the group consisting of branched alkyl, cyclic alkyl, bicyclic alkyl, multicyclic alkyl, and partially or fully deuterated variants of the same.

8. The compound of claim 1 , wherein R 1 or R 2 is iso-propyl.

9. The compound of claim 1 , wherein R 1 or R 2 contain one or more deuterium atoms.

10. The compound of claim 1 , wherein R 1 and R 2 contain one or more deuterium atoms.

11. The compound of claim 1 , wherein R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, partially or fully deuterated variations thereof, and combinations thereof.

12. The compound of claim 1 , wherein at least one of R 3 , R 4 , R 5 and R 6 comprises partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl.

13. The compound of claim 1 , wherein at least two of R 3 , R 4 , R 5 or R 6 independently comprise partially or fully deuterated alkyl or partially or fully deuterated cycloalkyl.

14. A first device comprising a first organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:

wherein R 1 and R 2 are optionally linked;

wherein the sum of the number of carbon atoms in R 1 and R 2 is at least 2;

wherein R 3 , R 4 , R 5 , and R 6 are optionally linked;

wherein R a and R b represent mono-, di-, tri- or tetra-substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 comprises a moiety selected from the group consisting of partially or fully deuterated alkyl and partially or fully deuterated cycloalkyl; and

wherein n is 1 or 2.

15. The first device of claim 14 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

16. The first device of claim 14 , wherein the organic layer further comprises a host.

17. The first device of claim 16 , wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CHC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 , or no substitution;

wherein n is from 1 to 10; and

wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

18. The first device of claim 16 , wherein the host is selected from the group consisting of:

and combinations thereof.

19. A consumer product comprising a first organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:

wherein R 1 and R 2 are optionally linked;

wherein the sum of the number of carbon atoms in R 1 and R 2 is at least 2;

wherein R 3 , R 4 , R 5 , and R 6 are optionally linked;

wherein R a and R b represent mono-, di-, tri- or tetra-substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one of R a , R b , R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 comprises a moiety selected from the group consisting of partially or fully deuterated alkyl and partially or fully deuterated cycloalkyl, and

wherein n is 1 or 2.

20. The compound of claim 1 , wherein the compound is selected from the group consisting of:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2019
From: KOTTAS, GREGG; ANSARI, NASRIN; ELSHENAWY, ZEINAB; DEANGELIS, ALAN; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 048947/0573 →
Continuity (8)
Continuation 14875147 · Oct 5, 2015
Continuation 14156808 · Jan 16, 2014
Continuation 13193221 · Jul 28, 2011
Continuation 16385637
Continuation 14225591 · Mar 26, 2014
Continuation 12727615 · Mar 19, 2010
Provisional Application 61162476 · Mar 23, 2009
Related Publication 20190245153A1 · Aug 8, 2019
Cited By (2)
US 12,408,242 US 12,550,604