IP Library Granted Patent US 10,211,413
Granted Patent B2
US 10,211,413 · App. 13/351,972 · Granted Feb 19, 2019

Organic electroluminescent materials and devices

Inventors: Bin Ma (Plainsboro, NJ); Zeinab M. Elshenawy (Holland, PA); Chuanjun Xia (Lawrenceville, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/06C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,211,413
App. No.
13/351,972
Granted
Feb 19, 2019
Kind
B2
Abstract

Novel heteroleptic iridium complexes are disclosed. The complexes contain a phenyl pyridine ligand and another ligand containing a dibenzofuran, dibenzothiophene, dibenzoselenophene, or carbazole linked to an imidazole or benzimidazole fragment. These complexes are useful materials when incorporated into OLED devices.

Claims (60)

1. A compound having a structure of formula:

wherein R 1 , R 2 , and R 3 represent mono-, di-, tri-, tetra-substitution or no substitution;

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, and combinations thereof;

wherein R4 is

wherein ring C is a 6-membered carbocyclic ring;

wherein R′ 1 , R′ 2 , and R′ 3 are selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combination thereof;

wherein at least one of R′ 1 and R′ 2 is not hydrogen or deuterium;

wherein R 7 represents mono-, di-, tri-, or tetra-substitution;

wherein R 7 is selected from the group consisting of hydrogen and a substitution selected from the group consisting of 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, combinations thereof, and partially or fully deuterated variations thereof;

wherein X is selected from the group consisting of O, S, and Se;

wherein m is 1 or 2; and

wherein at least one of the following is true:

(i) at least one R 7 is a substitution; and

(ii)(b) at least two R 2 are independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, combinations thereof, and partially or fully deuterated variations thereof.

2. The compound of claim 1 , wherein:

(ii)(b) at least two R 2 are independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, combinations thereof, and partially or fully deuterated variations thereof.

3. The compound of claim 1 , wherein (i) at least one R 7 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryl, heteroaryl, combinations thereof, and partially or fully deuterated variations thereof.

4. The compound of claim 1 , wherein ring C is phenyl.

5. The compound of claim 1 , wherein R′ 1 and R′ 2 are selected from the group consisting of methyl, ethyl, isopropyl, and phenyl; and wherein R′ 3 is H.

6. The compound of claim 1 , wherein R′ 1 is isopropyl, R′ 2 is isopropyl, and R′ 3 is H.

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

8. The compound of claim 1 , wherein the compound is

9. The compound of claim 1 , wherein the compound is

10. The compound of claim 1 , wherein m is 2.

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 a structure of formula:

wherein R 1 , R 2 , and R 3 represent mono-, di-, tri-, tetra-substitution or no substitution;

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, and combinations thereof;

wherein R4 is

wherein ring C is a 6-membered carbocyclic ring;

wherein R′ 1 , R′ 2 , and R′ 3 are selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combination thereof;

wherein at least one of R′ 1 and R′ 2 is not hydrogen or deuterium;

wherein R 7 represents mono-, di-, tri-, or tetra-substitution;

wherein R 7 is selected from the group consisting of hydrogen and a substitution selected from the group consisting of 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, combinations thereof, and partially or fully deuterated variations thereof;

wherein X is selected from the group consisting of O, S, and Se;

wherein m is 1 or 2; and

wherein at least one of the following is true:

(i) at least one R 7 is a substitution; and

(ii)(b) at least two R 2 are independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, combinations thereof, and partially or fully deuterated variations thereof.

12. The device of claim 11 , wherein:

(ii)(b) at least two R 2 are independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, combinations thereof, and partially or fully deuterated variations thereof.

13. 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, and a lighting panel.

14. The first device of claim 11 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.

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

16. The first device of claim 11 , 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≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and 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.

18. The first device of claim 17 , wherein the host comprises one or more compounds having the formula:

wherein p is 0 or 1.

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

and combinations thereof.

20. The first device of claim 16 , wherein the host comprises a metal complex.

21. The device of claim 11 , wherein X is O.

22. The device of claim 11 , wherein the compound is

23. The device of claim 11 , wherein the compound is

24. The device of claim 11 , wherein at least one R7 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryl, heteroaryl, combinations thereof, and partially or fully deuterated variations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2012
From: MA, BIN; ELSHENAWY, ZEINAB; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 027933/0981 →
Continuity (1)
Related Publication 20130181190A1 · Jul 18, 2013
Cited By (3)
US 12,635,400 US 12,668,606 US 12,703,715