IP Library Granted Patent US 9,634,264
Granted Patent B2
US 9,634,264 · App. 13/673,338 · Granted Apr 25, 2017

Organic electroluminescent materials and devices

Inventors: Scott Beers (Flemington, NJ); Chuanjun Xia (Lawrenceville, NJ); Harvey Wendt (Medford Lakes, NJ); Suman Layek (Lawrenceville, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/06C09K2211/185
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Quick Facts
Patent No.
US 9,634,264
App. No.
13/673,338
Granted
Apr 25, 2017
Kind
B2
Abstract

Novel iridium complexes containing phenylpyridine and pyridyl aza-benzo fused ligands are described. These complexes are useful as light emitters when incorporated into OLEDs.

Claims (47)

1. A compound having the formula Ir(L A ) n (L B ) 3-n , having the structure:

wherein A 1 and A 2 are carbon or nitrogen;

wherein A 6 , A 7 , and A 8 are carbon;

wherein A 5 is nitrogen;

wherein X is O, S, or Se;

wherein R 1 , R 2 , R 3 , and R 4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;

wherein any adjacent substitutions in R 1 , R 2 , R 3 , and R 4 are optionally linked together to form a ring;

wherein R 1 , R 2 , R 3 , and R 4 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; and

wherein n is an integer from 1 to 3.

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

3. The compound of claim 1 , wherein A 1 and A 2 are carbon.

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

5. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

6. The compound of claim 1 , wherein R 2 is alkyl.

7. The compound of claim 6 , wherein the alkyl is deuterated or partially deuterated.

8. The compound of claim 1 , wherein R 3 is alkyl.

9. The compound of claim 8 , wherein the alkyl is deuterated or partially deuterated.

10. The compound of claim 1 , wherein L B is selected from the group consisting of:

11. The compound of claim 1 , wherein L A is selected from the group consisting of:

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

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

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

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(L A ) n (L B ) 3-n , having the structure:

wherein A 1 and A 2 are carbon or nitrogen;

wherein A 6 , A 7 , and A 8 are carbon;

wherein A 5 is nitrogen;

wherein X is O, S, or Se;

wherein R 1 , R 2 , R 3 , and R 4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;

wherein any adjacent substitutions in R 1 , R 2 , R 3 , and R 4 are optionally linked together to form a ring;

wherein R 1 , R 2 , R 3 , and R 4 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, sulfanyl, sulfonyl, phosphino, and combinations thereof; and

wherein n is an integer from 1 to 3.

15. The first device of claim 14 , wherein the first device is a consumer product.

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

17. The first device of claim 14 , wherein the first device comprises a lighting panel.

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

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

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

21. The first device of claim 20 , 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.

22. The first device of claim 20 , wherein the host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

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

and combinations thereof.

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2013
From: BEERS, SCOTT; XIA, CHUANJUN; WENDT, HARVEY; LAYEK, SUMAN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 029638/0518 →
Continuity (1)
Related Publication 20140131663A1 · May 15, 2014