IP Library › Granted Patent US 10,312,458
Granted Patent B2
US 10,312,458 · App. 14/875,147 · Granted Jun 4, 2019

Organic electroluminescent materials and devices

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 10,312,458
App. No.
14/875,147
Granted
Jun 4, 2019
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 (50)

1. A compound having the formula:

wherein R 1 and R 2 are optionally linked;

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, deuterium, partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, and combinations thereof;

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 , 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, S═O, SO 2 , SiRR′, and GeRR′;

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

wherein the compound is heteroleptic; and

wherein n is 1 or 2.

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

3. The compound of claim 1 , wherein R 1 is hydrogen and R 2 is selected from the group consisting of partially or fully deuterated alkyl, partially or fully deuterated cycloalkyl, and combinations thereof.

4. A compound having the formula:

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

wherein R 3 , R 4 , R 5 , 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 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 n is 1 or 2, and

wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variations thereof, and combinations thereof and R 2 is hydrogen.

5. The compound of claim 1 , wherein R 1 and R 2 are partially or fully deuterated alkyl.

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

7. The compound of claim 1 , wherein R 1 or R 2 is partially or fully deuterated iso-propyl.

8. 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, arylalkyl, and combinations thereof.

9. The compound of claim 1 , wherein at least one of R 3 , R 4 , R 5 and R 6 comprises a branched alkyl, cyclic alkyl, bicyclic alkyl, a multicyclic alkyl, or a partially or fully deuterated variant thereof.

10. The compound of claim 1 , wherein R 3 , R 4 , R 5 or R 6 contain one or more deuterium atoms.

11. 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 R 1 and R 2 are independently selected from the group consisting of hydrogen, deuterium, partially or fully deuterate alkyl, partially or fully deuterated cycloalkyl, and combinations thereof;

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 , 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, S═O, SO 2 , SiRR′, and GeRR′;

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

wherein the compound is heteroleptic; and

wherein n is 1 or 2.

12. The first device of claim 11 , wherein the first device is selected from the group consisting of a consumer product, an organic light-emitting device, a lighting panel, and a combination thereof.

13. The first device of claim 11 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

14. The first device of claim 11 , wherein the organic layer comprises a host, and 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≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 ;

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.

15. The first device of claim 14 , wherein the host has the formula:

16. The first device of claim 11 , wherein the organic layer comprises a host, and the host is selected from the group consisting of:

and combinations thereof.

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

18. The compound of claim 4 , wherein the compound is selected from the group consisting of:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 6, 2015
From: KOTTAS, GREGG; ANSARI, NASRIN; ELSHENAWY, ZEINAB; DEANGELIS, ALAN; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 036733/0710 →
Continuity (5)
Continuation 14156808 · Jan 16, 2014
Continuation 13193221 · Jul 28, 2011
Continuation In Part 12727615 · Mar 19, 2010
Provisional Application 61162476 · Mar 23, 2009
Related Publication 20160099425A1 · Apr 7, 2016
Cited By (5)
US 12,408,242 US 12,550,604 US 12,635,400 US 12,703,715 US 12,742,114