Organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12239013-B2
Application number	US-202318364552-A
Country	US
Kind code	B2
Filing date	Aug 3, 2023
Priority date	Nov 7, 2017
Publication date	Feb 25, 2025
Grant date	Feb 25, 2025

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.

First claim

We claim:

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 transf

Assignees

• Universal Display Corp

Inventors

• Margulies Eric A
• Ji Zhiqiang
• Thompson Nicholas J
• Szigethy Geza
• Weaver Michael S
• Feldman Jerald

Classifications

• H10K85/351 Primary

  Metal complexes comprising lanthanides or actinides, e.g. comprising europium · CPC title

• H10K85/624

  containing six or more rings · CPC title

• H10K50/12 Primary

  comprising dopants · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title