Organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11910702-B2
Application number	US-201816158406-A
Country	US
Kind code	B2
Filing date	Oct 12, 2018
Priority date	Nov 7, 2017
Publication date	Feb 20, 2024
Grant date	Feb 20, 2024

Abstract

An OLED structure including a first organic layer disposed between the anode and the cathode is disclosed. The first organic layer includes a primary phosphorescent emitter and a first host, and where one of the following conditions is true: (1) the first organic layer further includes a secondary emitter; or (2) the OLED further includes a second organic layer disposed between the anode and the cathode, wherein the second organic layer includes a secondary emitter. The 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, and 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.

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 device 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 formula of M 1 (L A ) x (L B ) y (L C ) z ;
wherein L A , L B and L C are each a bidentate ligand;
wherein M 1 is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; 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 the metal M 1 ;
wherein L A is selected from the group consisting of:

L B and L C are each independently selected from the group consisting of:

wherein,
each X 1 to X 10 are independently selected from the group consisting of C and N;
at least one of X 1 to X 10 is N;
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″;
R′ and R″ are optionally fused or joined to form a ring;
each R a , R b , and R c represents from mono substitution to the maximum possible number of substitutions, or no substitution;
R′, R″, R a , R b , and R c 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
any two adjacent substituents of R a , R b , and R c can be fused or joined to form a ring or form a multidentate ligand;

wherein the primary phosphorescent emitter has a peak emission wavelength λmax that is ≥600 nm and ≤750 nm;
wherein the secondary emitter is a near-infrared emitter that has a peak emission wavelength λmax that is between 750 nm and 2500 nm;
wherein the first host has a lowest excited state triplet energy T 1 that is at least 0.1 eV higher than that of the primary phosphorescent emitter;
wherein the secondary emitter is selected from the group consisting of: a fluorescent emitter, a thermally activated delayed fluorescence emitter, and an emitter containing an unpaired electron in its ground state,
whereby Dexter energy transfer from the primary emitter to the secondary emitter is minimized to prevent formation of fluorophore triplet excitons.

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 wherein 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 wherein 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 wherein an average intermolecular distance between the primary phosphorescent emitter and the secondary emitter is ≥8 Å.

10. The OLED of claim 1 , wherein the condition (2) is true, whereby the primary emitter and the secondary emitter are spatially isolated to minimize any Dexter energy transfer and prevent formation of fluorophore triplet excitons.

11. The OLED of claim 10 , wherein the first organic layer and the second organic layer are separated by one or more layers of host or transport materials to achieve an interlayer separation distance of greater than 1 nm.

12. The OLED of claim 1 , wherein the condition (1) is true and the primary and secondary emitters are doped in the first organic layer at doping concentrations that result in donor-acceptor radius r, defined as the distance between the aromatic π-systems of the two emitters, being greater than 8 Å.

13. 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 device 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 formula of M 1 (L A ) x (L B ) y (L C ) z ;
wherein L A , L B and L C are each a bidentate ligand;
wherein M 1 is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; 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 the metal M 1 ;
wherein L A is selected from the group consisting of:

L B and L C are each independently selected from the group consisting of:

wherein,
each X 1 to X 10 are independently selected from the group consisting of C and N;
at least one of X 1 to X 10 is N;
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″;
R′ and R″ are optionally fused or joined to form a ring;
each R a , R b , and R c represents from mono substitution to the maximum possible number of substitutions, or no substitution;
R′, R″, R a , R b , and R c 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
any two adjacent substituents of R a , R b , and R c can be fused or joined to form a ring or form a multidentate ligand;

wherein the primary phosphorescent emitter has a

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K50/125

  specially adapted for multicolour light emission, e.g. for emitting white light · CPC title