IP Library › Granted Patent US 6,939,624
Granted Patent B2
US 6,939,624 · App. 09/978,455 · Granted Sep 6, 2005

Organometallic compounds and emission-shifting organic electrophosphorescence

Assignees: Universal Display Corporation; The University of Southern California; The Trustees of Princeton University
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Quick Facts
Patent No.
US 6,939,624
App. No.
09/978,455
Granted
Sep 6, 2005
Kind
B2
Abstract

Emissive phosphorescent organometallic compounds are described that produce improved electroluminescence, particularly in the blue region of the visible spectrum. Organic light emitting devices employing such emissive phosphorescent organometallic compounds are also described. Also described is an organic light emitting layer including a host material having a lowest triplet excited state having a decay rate of less than about 1 per second; a guest material dispersed in the host material, the guest material having a lowest triplet excited state having a radiative decay rate of greater than about 1×10 5 or about 1×10 6 per second and wherein the energy level of the lowest triplet excited state of the host material is lower than the energy level of the lowest triplet excited state of the guest material.

Claims (39)

1. An organic light emitting device having an emissive layer comprising an organometallic compound, wherein the organometallic compound comprised consists of

a metal having an atomic number of at least 72;

at least one mono-anionic, bidentate, carbon coordination ligand bound to the metal, wherein the at least one mono-anionic, bidentate, carbon-coordination ligand is substituted with at least one of an electron donating substituent and an electron withdrawing substituent, and

at least one non mono-anionic, bidentate, carbon coordination ligand bound to the metal,

wherein the mono-anionic, bidentate, carbon-coordination ligand is selected from the group consisting of

wherein

wherein R 1 , R 2 , R 3 and R 4 are, independently, hydrogen, halogen, alkyl or aryl.

2. The organic light emitting device of claim 1 , wherein the metal is selected from the group consisting of Os, Ir, Pt and Au.

3. The organic light emitting device of claim 2 , wherein the metal is selected from the group consisting of Ir and Pt.

4. The organic light emitting device of claim 1 , wherein the non mono-anionic, bidentate, carbon coordination ligand is selected from the group consisting of

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

X is selected from the group consisting of CH and N; and

R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are, independently, hydrogen, halogen, alkyl or aryl.

5. The organic light emitting device of claim 4 , wherein the non mono-anionic, bidentate, carbon coordination ligand is selected from the group consisting of

6. The organic light emitting device of claim 1 , wherein the emissive layer further comprises:

a host material having a lowest triplet excited state having a first decay rate of less than about 1 per second; wherein the organometallic compound is present as a guest material dispersed in the host material, the organometallic compound having a lowest triplet excited state having a radiative decay rate of greater than about 1×10 5 per second and wherein the energy level of the lowest triplet excited state of the host material is lower than the energy level of the lowest triplet excited state of the organometallic compound.

7. The organic light emitting device of claim 6 , wherein the energy difference between the lowest triplet excited state of the organometallic compound and a corresponding relaxed state of the organometallic compound has a corresponding wavelength of about 420 nm to 480 nm for blue light emission.

8. The organic light emitting device of claim 6 , wherein the energy difference between the lowest triplet excited state of the organometallic compound and a corresponding relaxed state of the organometallic compound has a corresponding wavelength of about 480 nm to 510 nm for aqua-blue light emission.

9. The organic light emitting device of claim 6 , wherein the host material has a bandgap with an energy difference corresponding to about 470 nm and the organometallic compound has a lowest triplet excited state at an energy level at about 450 nm.

10. The organic light emitting device of claim 6 , wherein the host material is an electron transport layer.

11. The organic light emitting device of claim 6 , wherein the host material conducts electrons primarily through hole transmission.

12. The organic light emitting device of claim 6 , wherein the ratio of the host material and organometallic compound decay rates is at least about 1:1000 to about 5:1000.

13. The organic light emitting device of claim 6 , wherein the host material is TPD.

14. The organic light emitting device of claim 6 , wherein a plurality of organometallic compounds are dispersed in the host material.

15. An organic light emitting device having an emissive layer comprising an organometallic compound, wherein the organometallic compound comprised consists of

a metal having an atomic number of at least 72;

at least one mono-anionic, bidentate, carbon coordination ligand bound to the metal, wherein the at least one mono-anionic, bidentate, carbon-coordination ligand is substituted with at least one of an electron donating substituent and an electron withdrawing substituent; and

at least one non (mono-anionic, bidentate, carbon coordination) ligand bound to the metal,

wherein the non-(mono-anionic, bidentate, carbon-coordination) ligand is selected from the group consisting of

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

X is selected from the group consisting of CH and N; and

R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are, independently, hydrogen, halogen, alkyl or aryl.

16. The organic light emitting device of claim 15 , wherein the non mono-anionic, bidentate, carbon coordination ligand is selected from the group consisting of

17. The organic light emitting device of claim 15 , wherein the metal is selected from the group consisting of Os, Ir, Pt and Au.

18. The organic light emitting device of claim 17 , wherein the metal is selected from the group consisting of Ir and Pt.

19. The organic light emitting device of claim 15 , wherein the mono-anionic, bidentate, carbon coordination ligand is selected from the group consisting of

wherein X=S or O; and

R 1 , R 2 , R 3 , R 4 and R 5 are, independently, hydrogen, halogen, alkyl, aryl.

20. An organic light emitting device having an emissive layer comprising an organometallic compound, wherein the organometallic compound has the chemical structure represented by a formula selected from the group consisting of

Assignments (4)
PARTIAL ASSIGNMENT Recorded Apr 5, 2007
From: UNIVERSAL DISPLAY CORPORATION
To: TRUSTEES OF PRINCETON UNIVERSITY, THE; SOUTHERN CALIFORNIA, UNIVERSITY OF, THE
Reel/Frame 019129/0231 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2002
From: ADACHI, CHIHAYA; BALDO, MARC A.; FORREST, STEPHEN R.
To: TRUSTEES OF PRINCETON UNIVERSITY, THE
Reel/Frame 012968/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2002
From: LAMANSKY, SERGEY; THOMPSON, MARK E.; ADAMOVICH, VADIM; DJUROVICH, PETER I.
To: UNIVERSITY OF SOUTHERN CALIFORNIA, THE
Reel/Frame 012538/0686 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2002
From: KWONG, RAYMOND
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 012538/0723 →
Continuity (3)
Continuation In Part 0963776600 · Aug 11, 2000
Provisional Application 6028381400 · Apr 13, 2001
Related Publication 20020182441A1 · Dec 5, 2002