IP Library › Granted Patent US 9,663,544
Granted Patent B2
US 9,663,544 · App. 13/558,250 · Granted May 30, 2017

Organic electroluminescent materials and devices

Inventors: Jui-Yi Tsai (Newton, NJ); Gregg Kottas (Ewing, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
C07F15/0033C09K11/06H01L51/0052H01L51/0054H01L51/0058H01L51/0067H01L51/0071H01L51/0072H01L51/0074H01L51/0085C09K2211/1029C09K2211/1044C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 9,663,544
App. No.
13/558,250
Granted
May 30, 2017
Kind
B2
Abstract

Heteroleptic cyclometallated complexes having a 6-membered ring cyclometallated to the metal, as shown in Formula (I), are provided: wherein ring A and ring B are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein L 1 is BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, or GeRR; wherein Z 1 and Z 2 are independently carbon or nitrogen; wherein at least one of Z 1 and Z 2 is carbon; wherein is a bidentate ligand selected from the group consisting of: wherein R 1 , R 2 , R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution; wherein R 1 , R 2 , R, R′, R a , R b , R c , and R d are each independently selected from various substituents; and wherein n is 1 or 2. Devices, such as organic light emitting devices (OLEDs) that comprise phosphorescent light emitting materials are also provided.

Claims (54)

1. A compound of Formula (I):

wherein ring A and ring B are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;

wherein L 1 is BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, or GeRR′;

wherein Z 1 and Z 2 are independently carbon or nitrogen;

wherein at least one of Z 1 and Z 2 is carbon;

wherein

is a bidentate ligand selected from the group consisting of:

wherein R 1 , R a , R b , R e , and R d may represent no substitution up to the maximum possible substitution;

wherein R 1 , R 2 , R, R′, R′ a , R a , R b , R c , and R d are each 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 any two adjacent substituents of R 1 , R 2 , R, R′, R a , R b , R c , and R d are optionally joined to form a ring and can be further substituted; and

wherein n is 1 or 2.

2. The compound of claim 1 , wherein

3. The compound of claim 1 , wherein A-L 1 -B is

4. The compound of claim 3 , wherein L 1 is CRR′, wherein R and R′ are alkyl.

5. The compound of claim 4 , wherein CRR′ is C(CH 3 ) 2 .

6. The compound of claim 1 , wherein A-L 1 -B is:

wherein R 6 is 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.

7. The compound of claim 1 , wherein A-L 1 -B is

wherein R 5 is 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.

8. The compound of claim 1 , wherein the ring A is an imidazole ring, which may be substituted as indicated, and Z 1 is nitrogen.

9. The compound of claim 1 , wherein A-L 1 -B is

wherein R 5 and R 6 are each 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.

10. The compound of claim 1 , wherein

is:

and wherein R 7 and R 8 are alkyl.

11. The compound of claim 1 , which is selected from the group consisting of:

12. 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 of Formula (I):

wherein ring A and ring B are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein L 1 is BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, or GeRR′;

wherein Z 1 and Z 2 are independently carbon or nitrogen;

wherein at least one of Z 1 and Z 2 is carbon;

wherein

is a bidentate ligand selected from the group consisting of:

wherein R 1 , R 2 , R′ a , R a , R b , R c , and R d may represent no substitution up to the maximum possible substitution;

wherein R 1 , R 2 , R, R′, R b , R c , and R d are each 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 any two adjacent substituents of R 1 , R 2 , R, R′, R a , R b , R c , and R d are optionally joined to form a ring and can be further substituted; and

wherein n is 1 or 2.

13. The first device of claim 12 , wherein the first device is a consumer product.

14. The first device of claim 12 , wherein the first device is an organic light-emitting device.

15. The first device of claim 12 , wherein the first device comprises a lighting panel.

16. The first device of claim 12 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.

17. The first device of claim 12 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

18. The first device of claim 12 , wherein the organic layer further comprises a host.

19. The first device of claim 18 , 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≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and C n H 2n —Ar 1 , or the host has no substitutions;

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.

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

, and combinations thereof.

21. The first device of claim 18 , wherein the host comprises a metal complex.

22. The first device of claim 18 , wherein the host comprises at least one of the chemical groups selected from the group consisting of carbazole, dibenzothiophene dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2012
From: TSAI, JUI-YI; KOTTAS, GREGG
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 028770/0109 →
Continuity (1)
Related Publication 20140027716A1 · Jan 30, 2014