IP Library › Granted Patent US 11,641,753
Granted Patent B2
US 11,641,753 · App. 16/045,876 · Granted May 2, 2023

Organic light-emitting device

Inventors: Sunghun Lee (Hwaseong-si, KR); Sangdong Kim (Seoul, KR); Seungyeon Kwak (Suwon-si, KR); Hyun Koo (Seongnam-si, KR); Jungin Lee (Seoul, KR); Kyuyoung Hwang (Anyang-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H01L51/5016C07F15/0086C09K11/06H01L51/0087H01L51/5004H01L51/5044H01L51/5056H01L51/5072C09K2211/1044C09K2211/185H01L51/0054H01L51/0067H01L51/0072H01L2251/5384H01L2251/552
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Quick Facts
Patent No.
US 11,641,753
App. No.
16/045,876
Granted
May 2, 2023
Kind
B2
Abstract

An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, wherein the emission layer includes an electron transport host, a hole transport host, and a dopant, wherein the dopant includes an organometallic compound, and wherein the organometallic compound does not comprise iridium, wherein the organic light-emitting device satisfies predetermined parameters described in the specification.

Claims (71)

1. An organic light-emitting device comprising:

a first electrode,

a second electrode facing the first electrode, and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer, and the emission layer comprises an electron transport host, a hole transport host, and a dopant,

wherein the electron transport host comprises a triphenylene group and a triazine group, and the hole transport host comprises a carbazole group,

the dopant comprises an organometallic compound, and the organometallic compound does not comprise iridium,

the organic light-emitting device satisfies a condition of

LUMO(dopant)−LUMO(host-E)≥0.15 eV and LUMO(host-E)−HOMO(host-H)>T1(dopant),

wherein LUMO(dopant) indicates a lowest unoccupied molecular orbital (LUMO) energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(host-E) indicates a LUMO energy level (expressed in electron volts) of the electron transport host in the emission layer,

HOMO(host-H) indicates a highest occupied molecular orbital (HOMO) energy level (expressed in electron volts) of the hole transport host in the emission layer, and

T1(dopant) indicates a triplet energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(dopant), LUMO(host-E), and HOMO(host-H) each indicate a negative value measured by differential pulse voltammetry using ferrocene as a reference material, and

T1(dopant) is a value calculated from a peak wavelength of a phosphorescence spectrum of the dopant measured using a luminescence measuring device.

2. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of 0.15 eV≤LUMO(dopant)−LUMO(host-E)≤0.6 electron volts.

3. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of 0 electron volts<[LUMO(host-E)−HOMO(host-H)]−T1(dopant)≤0.5 electron volts.

4. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO(dopant)<LUMO(host-H), wherein LUMO(host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.

5. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO(host-E)<LUMO(host-H), wherein LUMO(host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.

6. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO(host-E)<LUMO(dopant)<LUMO(host-H), wherein LUMO(host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.

7. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of HOMO(host-E)<HOMO(host-H).

8. The organic light-emitting device of claim 1 , wherein the dopant is an organometallic compound including platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), ruthenium (Ru), rhenium (Re), beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), palladium (Pd), silver (Ag), or gold (Au).

9. The organic light-emitting device of claim 1 , wherein the dopant is an organometallic compound having a square-planar coordination structure.

10. The organic light-emitting device of claim 1 , wherein the dopant satisfies a condition of T1(dopant)≤E gap (dopant)>T1(dopant)+0.5 electron volts,

wherein E gap (dopant) is a difference between HOMO(dopant) and LUMO(dopant) of the dopant, and

HOMO(dopant) indicates a HOMO energy level of the dopant, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.

11. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of −2.8 electron volts ≤LUMO(dopant)≤−2.3 electron volts and −6.0 electron volts ≤HOMO(dopant)≤−4.5 electron volts, wherein HOMO(dopant) indicates a HOMO energy level of the dopant, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.

12. The organic light-emitting device of claim 1 , wherein the dopant comprises a metal M and an organic ligand, and the metal M and the organic ligand form one, two, or three cyclometalated rings.

13. The organic light-emitting device of claim 1 , wherein the dopant comprises a metal M and a tetradentate organic ligand capable of forming three or four cyclometalated rings with the metal M,

the metal M is platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), ruthenium (Ru), rhenium (Re), beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), palladium (Pd), silver (Ag), or gold (Au), and the tetradentate organic ligand comprises a benzimidazole group and a pyridine group.

14. The organic light-emitting device of claim 1 , wherein the electron transport host further comprises at least one electron transport moiety selected from a cyano group, a π electron-depleted nitrogen-containing cyclic group, and groups represented by the following formulae:

wherein *, *′, and *″ in the formulae above each indicate a binding site to a neighboring atom.

15. The organic light-emitting device of claim 1 , wherein the electron transport host has a lowest anion decomposition energy of 2.5 electron volts or more.

16. The organic light-emitting device of claim 1 , further comprising

a hole transport region disposed between the first electrode and the emission layer,

wherein the hole transport region comprises an amine-containing compound.

17. An organic light-emitting device comprising:

a first electrode,

a second electrode facing the first electrode,

light-emitting units in a number of m that are stacked between the first electrode and the second electrode, wherein the light-emitting units comprise at least one emission layer, and

charge-generation layers in a number of m−1 that are disposed between two neighboring light-emitting units selected from the light-emitting units in the number of m, wherein the charge-generation layers include an n-type charge-generation layer and a p-type charge-generation layer,

wherein m is an integer greater than or equal to 2,

a maximum emission wavelength of light emitted by at least one of the light-emitting units in the number of m is different from a maximum emission wavelength of light emitted by at least one of the other light-emitting units,

the emission layer comprises an electron transport host, a hole transport host, and a dopant,

wherein the electron transport host comprises a triphenylene group and a triazine group, and the hole transport host comprises a carbazole group,

the dopant comprises an organometallic compound, provided that the organometallic compound does not comprise iridium, and

the organic light-emitting device satisfies a condition of

LUMO(dopant)−LUMO(host-E)≥0.15 electron volts and LUMO(host-E)−HOMO(host-H)>T1(dopant),

wherein LUMO(dopant) indicates a LUMO energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(host-E) indicates a LUMO energy level (expressed in electron volts) of the electron transport host in the emission layer,

HOMO(host-H) indicates a HOMO energy level (expressed in electron volts) of the hole transport host in the emission layer,

T1(dopant) indicates a triplet energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(dopant), LUMO(host-E), and HOMO(host-H) each indicate a negative value measured by differential pulse voltammetry using ferrocene as a reference material, and

T1(dopant) indicates a value calculated from a peak wavelength of a phosphorescence spectrum of the dopant measured using a luminescence measuring device.

18. An organic light-emitting device comprising:

a first electrode,

a second electrode facing the first electrode, and

light-emitting units in a number of m that are stacked between the first electrode and the second electrode,

wherein m is an integer of greater than or equal to 2,

a maximum emission wavelength of light emitted by at least one of the light-emitting units in the number of m is different from a maximum emission wavelength of light emitted by at least one of the other light-emitting units,

the emission layer includes an electron transport host, a hole transport host, and a dopant,

wherein the electron transport host comprises a triphenylene group and a triazine group, and the hole transport host comprises a carbazole group,

the dopant includes an organometallic compound, provided that the organometallic compound does not include iridium, and

the organic light-emitting device satisfies a condition of

LUMO(dopant)−LUMO(host-E)≥0.15 electron volts and LUMO(host-E)−HOMO(host-H)>T1 (dopant),

wherein LUMO(dopant) indicates a LUMO energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(host-E) indicates a LUMO energy level (expressed in electron volts) of the electron transport host in the emission layer,

HOMO(host-H) indicates a HOMO energy level (expressed in electron volts) of the hole transport host in the emission layer,

T1(dopant) indicates a triplet energy level (expressed in electron volts) of the dopant in the emission layer,

LUMO(dopant), LUMO(host-E), and HOMO(host-H) each indicate a negative value measured by differential pulse voltammetry using ferrocene as a reference material, and

T1(dopant) indicates a value calculated from a peak wavelength of a phosphorescence spectrum of the dopant measured using a luminescence measuring device.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2018
From: LEE, SUNGHUN; KIM, SANGDONG; KWAK, SEUNGYEON; KOO, HYUN; LEE, JUNGIN; HWANG, KYUYOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 046465/0572 →
Priority Claims (1)
KR 10-2017-0097132 · Jul 31, 2017 · national
Continuity (1)
Related Publication 20190058144A1 · Feb 21, 2019
Cited By (1)
US 12,324,298