IP Library › Granted Patent US 12,274,157
Granted Patent B2
US 12,274,157 · App. 18/497,730 · Granted Apr 8, 2025

Organic electroluminescent materials and devices

Inventors: Eric A. Margulies (Ewing, NJ); Zhiqiang Ji (Hillsborough, NJ); Jui-Yi Tsai (Newtown, PA); Chun Lin (Yardley, PA); Alexey Borisovich Dyatkin (Ambler, PA); Mingjuan Su (Ewing, NJ); Bin Ma (Plainsboro, NJ); Michael S. Weaver (Princeton, NJ); Julia J. Brown (Yardley, PA); Lichang Zeng (Lawrenceville, NJ); Walter Yeager (Yardley, PA); Alan Deangelis (Pennington, NJ); Chuanjun Xia (Lawrenceville, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H10K85/342C07F15/0033C09K11/06C09K2211/1007C09K2211/1011C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/185H10K50/11H10K50/81H10K50/82H10K2101/10
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Quick Facts
Patent No.
US 12,274,157
App. No.
18/497,730
Granted
Apr 8, 2025
Kind
B2
Abstract

A compound is disclosed that has a metal coordination complex structure having at least two ligands coordinated to the metal; wherein the compound has a first substituent R 1 at one of the ligands' periphery; wherein a first distance is defined as the distance between the metal and one of the atoms in R 1 where that atom is the farthest away from the metal among the atoms in R 1 ; wherein the first distance is also longer than any other atom-to-metal distance between the metal and any other atoms in the compound; and wherein when a sphere having a radius r is defined whose center is at the metal and the radius r is the smallest radius that will allow the sphere to enclose all atoms in the compound that are not part of R 1 , the first distance is longer than the radius r by at least 2.9 Å.

Claims (49)

1. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an emissive layer, disposed between the anode and the cathode, comprising a phosphorescent emitting compound;

wherein the phosphorescent emitting compound has an intrinsic emission spectrum with a FWHM value of no more than 45 nm;

wherein the OLED has an EQE of at least 25% measured at 0.1 mA/cm 2 at room temperature when a voltage is applied across the device;

wherein the phosphorescent emitting compound is a metal coordination complex;

wherein the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Au, Ag, and Cu;

wherein the phosphorescent emitting compound comprises a first benzene ring coordinated to the metal;

wherein the first benzene ring is fused by a second aromatic ring, which is fused by a third aromatic ring, which is fused by a fourth aromatic ring.

2. The OLED of claim 1 , wherein the FWHM is no more than 43 nm and the EQE is at least 27%.

3. The OLED of claim 1 , wherein the metal is Ir.

4. The OLED of claim 1 , wherein the metal is Pt.

5. The OLED of claim 1 , wherein the phosphorescent emitting compound has a horizontal dipole ratio of at least 0.7.

6. The OLED of claim 1 , wherein the phosphorescent emitting compound has a horizontal dipole ratio of at least 0.8.

7. The OLED of claim 1 , wherein the phosphorescent emitting compound has a horizontal dipole ratio of at least 0.9.

8. The OLED of claim 1 , wherein the emissive layer further comprises a host; and

wherein the compound has a horizontal dipole ratio that is higher by at least 5% when compared to the exact same device with mCP (1,3-bis(N-carbazolyl) benzene) as host.

9. The OLED of claim 1 , wherein the emissive layer further comprises a host; and

wherein the compound has a horizontal dipole ratio that is higher by at least 10% when compared to the exact same device with mCP (1,3-bis(N-carbazolyl) benzene) as host.

10. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an emissive layer, disposed between the anode and the cathode, comprising a phosphorescent emitting compound;

wherein the phosphorescent emitting compound has an intrinsic emission spectrum with a FWHM value of no more than 45 nm;

wherein the OLED has an EQE of at least 25% measured at 0.1 mA/cm 2 at room temperature when a voltage is applied across the device;

wherein the phosphorescent emitting compound is a metal coordination complex;

wherein the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Au, Ag, and Cu;

wherein the phosphorescent emitting compound comprises a first benzene ring coordinated to the metal;

wherein the first benzene ring is fused by a second aromatic ring, which is fused by a third aromatic ring, which is fused by a fourth aromatic ring.

11. The consumer product of claim 10 , wherein the FWHM is no more than 43 nm and the EQE is at least 27%.

12. The consumer product of claim 10 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, and a sign.

13. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an emissive layer, disposed between the anode and the cathode, comprising a phosphorescent emitting compound;

wherein the phosphorescent emitting compound has an intrinsic emission spectrum with a FWHM value of no more than 45 nm;

wherein the OLED has an EQE of at least 25% measured at 0.1 mA/cm 2 at room temperature when a voltage is applied across the device; and

wherein at least one of the following is true:

(i) the phosphorescent emitting compound has a horizontal dipole ratio of at least 0.9; or

(ii) the emissive layer further comprises a host; and the compound has a horizontal dipole ratio that is higher by at least 5% when compared to the exact same device with mCP (1,3-bis(N-carbazolyl) benzene) as host.

14. The OLED of claim 13 , wherein the phosphorescent emitting compound has a horizontal dipole ratio of at least 0.9.

15. The OLED of claim 14 , wherein the emissive layer further comprises a host; and

wherein the compound has a horizontal dipole ratio that is higher by at least 5% when compared to the exact same device with mCP (1,3-bis(N-carbazolyl) benzene) as host.

16. The OLED of claim 13 , wherein the emissive layer further comprises a host; and

wherein the compound has a horizontal dipole ratio that is higher by at least 5% when compared to the exact same device with mCP (1,3-bis(N-carbazolyl) benzene) as host.

17. A consumer product comprising an organic light-emitting device (OLED) of claim 13 .

18. The consumer product of claim 17 , wherein the FWHM is no more than 43 nm and the EQE is at least 27%.

19. The consumer product of claim 17 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, and a sign.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Oct 30, 2023
From: MARGULIES, ERIC A.; JI, ZHIQIANG; TSAI, JUI-YI; LIN, CHUN; DYATKIN, ALEXEY BORISOVICH; SU, MINGJUAN; MA, BIN; WEAVER, MICHAEL S.; BROWN, JULIA J.; YEAGER, WALTER; DEANGELIS, ALAN; ZENG, LICHANG; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 065392/0883 →
Continuity (10)
Continuation 17751890 · May 24, 2022
Continuation 16853899 · Apr 21, 2020
Continuation 15619217 · Jun 9, 2017
Provisional Application 62516329 · Jun 7, 2017
Provisional Application 62480746 · Apr 3, 2017
Provisional Application 62479795 · Mar 31, 2017
Provisional Application 62450848 · Jan 26, 2017
Provisional Application 62352139 · Jun 20, 2016
Provisional Application 62352119 · Jun 20, 2016
Related Publication 20240107874A1 · Mar 28, 2024
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