IP Library › Granted Patent US 12,239,013
Granted Patent B2
US 12,239,013 · App. 18/364,552 · Granted Feb 25, 2025

Organic electroluminescent devices

Inventors: Eric A. Margulies (Ewing, NJ); Zhiqiang Ji (Ewing, NJ); Nicholas J. Thompson (Ewing, NJ); Geza Szigethy (Newtown, PA); Michael S. Weaver (Ewing, NJ); Jerald Feldman (Wilmington, DE)
Assignee: UNIVERSAL DISPLAY CORPORATION
H10K85/351H10K50/11H10K50/125H10K50/131H10K50/171H10K50/18H10K50/81H10K50/82H10K85/342H10K85/346H10K85/348H10K85/371H10K50/15H10K50/16H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 12,239,013
App. No.
18/364,552
Granted
Feb 25, 2025
Kind
B2
Abstract

Provided is an OLED structure includes an organic layer having a primary phosphorescent emitter and a first host; where one of the following conditions is true: (1) the organic layer further includes a secondary emitter; or (2) the OLED further includes a second organic layer where the second organic layer includes a secondary emitter. The primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm; the secondary emitter has a peak emission wavelength λmax that is ≥750 nm; the primary phosphorescent emitter is capable of transferring energy to the secondary emitter; the first host has a lowest excited state triplet energy T1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter; the primary phosphorescent emitter has the formula Pt(L 1 ) m ; L 1 can represent one or more ligands that are the same or different; each L 1 is independently monodentate or multidentate; and m represents a maximum possible number of ligands L 1 that can coordinate to Pt.

Claims (65)

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

an anode;

a cathode;

a first organic layer, disposed between the anode and the cathode;

wherein the first organic layer comprises a primary phosphorescent emitter and a first host;

wherein one of the following conditions is true:

(1) the first organic layer further comprises a secondary emitter; or

(2) the OLED further comprises a second organic layer disposed between the anode and the cathode, wherein the second organic layer comprises a secondary emitter;

wherein the primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm;

wherein the secondary emitter has a peak emission wavelength λmax that is ≥750 nm;

wherein the primary phosphorescent emitter is capable of transferring energy to the secondary emitter;

wherein the first host has a lowest excited state triplet energy Tl that is at least 0.1 eV higher than that of the primary phosphorescent emitter;

wherein the primary phosphorescent emitter has the formula Pt(L 1 ) m ;

wherein L 1 can represent one or more ligands that are the same or different;

wherein each L 1 is independently monodentate or multidentate;

wherein m represents a maximum possible number of ligands L 1 that can coordinate to Pt.

2. The OLED of claim 1 , wherein the condition (1) is true, and the first organic layer is the only layer containing the secondary emitter.

3. The OLED of claim 1 , wherein the condition (2) is true, and the second organic layer is the only layer containing the secondary emitter.

4. The OLED of claim 1 , wherein the secondary emitter has a peak absorption wavelength and the difference between the peak emission wavelength λ max of the primary phosphorescent emitter and the peak absorption wavelength λ max of the secondary emitter is less than 200 nm.

5. The OLED of claim 1 , wherein the first organic layer and the second organic layer are separated by one or more additional organic layers.

6. The OLED of claim 5 , wherein the separation between the first organic layer and the second organic layer is ≥1 nm.

7. The OLED of claim 1 , wherein the condition (1) is true, and the concentration of the primary phosphorescent emitter and concentration of the secondary emitter in the first organic layer are different.

8. The OLED of claim 1 , wherein the condition (1) is true, and the concentration of the primary phosphorescent emitter and the concentration of the secondary emitter in the first organic layer are each ≤10 wt. %.

9. The OLED of claim 1 , wherein the condition (1) is true, and an average intermolecular distance between the primary phosphorescent emitter and the secondary emitter is ≥8 Å.

10. The OLED of claim 1 , wherein the secondary emitter has the formula M 2 L 2 n ;

wherein M 2 is selected from the group consisting of the lanthanide metals;

wherein L 2 represents one or more ligands that are the same or different;

wherein each L 2 is independently monodentate or multidentate; and

wherein n represents a maximum possible number of L 2 ligands that can coordinate to M 2 .

11. The OLED of claim 10 , wherein the primary phosphorescent emitter has a lowest triplet energy T1 that is the same or higher than the energy of the emissive f-f transition Eff of the secondary emitter.

12. The OLED of claim 10 , wherein M 2 is selected from the group consisting of Eu, Nd, Yb, and Er.

13. The OLED of claim 10 , wherein the secondary emitter M 2 L 2 n is selected from the group consisting of:

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

wherein R A , R B , R C , R D , R E , and R F can represent mono to the maximum possible substitution, or no substitution;

wherein R A , R B , R C , R D , R E , and R F are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, benzonitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein L 3 and L 4 are each independently selected from direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof.

14. The OLED of claim 1 , wherein the secondary emitter is selected from a group consisting of a fluorescent emitter, a thermally activated delayed fluorescence emitter, and an emitter containing an unpaired electron in its ground state.

15. The OLED of claim 1 , wherein the primary phosphorescent emitter has a formula of Pt(L A ) x (L B ) y (L C ) z ;

wherein L A , L B and L C are each a bidentate ligand; and

wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of Pt.

16. The OLED of claim 15 , wherein L A , L B , and L C are each independently selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;

wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d can represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d are each independently a hydrogen or a substitutent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, benzonitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein any two adjacent substitutents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

17. The OLED of claim 1 , wherein the first host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

18. A consumer product comprising an OLED comprising:

an anode;

a cathode; and

a first organic layer disposed between the anode and the cathode;

wherein the first organic layer comprises a primary phosphorescent emitter and a first host;

wherein one of the following conditions is true:

(1) the first organic layer further comprises a secondary emitter; or

(2) the OLED further comprises a second organic layer disposed between the anode and the cathode, wherein the second organic layer comprises a secondary emitter;

wherein the primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm;

wherein the secondary emitter has a peak emission wavelength λmax that is ≥750 nm;

wherein the primary phosphorescent emitter is capable of transferring energy to the secondary emitter;

wherein the first host has a lowest excited state triplet energy T1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter;

wherein the primary phosphorescent emitter has the formula Pt(L 1 ) m ;

wherein L 1 can represent one or more ligands that are the same or different;

wherein each L 1 is independently monodentate or multidentate;

wherein m represents a maximum possible number of ligands L 1 that can coordinate to Pt;

wherein the consumer product is one 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 OLED, 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, a light therapy device, or a sign.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Aug 3, 2023
From: MARGULIES, ERIC A.; JI, ZHIQIANG; THOMPSON, NICHOLAS J.; SZIGETHY, GEZA; WEAVER, MICHAEL S.; FELDMAN, JERALD
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 064479/0076 →
Continuity (3)
Continuation 16158406 · Oct 12, 2018
Provisional Application 62582359 · Nov 7, 2017
Related Publication 20230380265A1 · Nov 23, 2023
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