IP Library Granted Patent US 11,289,668
Granted Patent B2
US 11,289,668 · App. 16/120,932 · Granted Mar 29, 2022

Organic light-emitting device

Inventors: Seungyeon Kwak (Suwon-si, KR); Hyun Koo (Seongnam-si, KR); Sangdong Kim (Seoul, KR); Jiwhan Kim (Seoul, KR); Sunghun Lee (Hwaseong-si, KR); Hyeonho Choi (Seoul, KR); Seokhwan Hong (Seoul, KR); Kyuyoung Hwang (Anyang-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H01L51/5028C09K11/06H01L51/0059H01L51/502H01L51/5016H01L51/5064H01L51/0053H01L51/0054H01L51/0067H01L51/0072H01L51/0087H01L2251/5384H01L2251/55
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Quick Facts
Patent No.
US 11,289,668
App. No.
16/120,932
Granted
Mar 29, 2022
Kind
B2
Abstract

An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer comprises a host and a dopant, wherein the emission layer emits a phosphorescent light, wherein the dopant is an organometallic compound, and wherein the emission layer satisfies certain parameters described in the specification.

Claims (89)

1. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

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

wherein

the emission layer comprises a host and a dopant,

the emission layer emits a phosphorescent light,

the dopant is an organometallic compound,

a photoluminescence quantum yield (PLQY) of the dopant is about 0.8 or greater and about 1.0 or less,

a decay time of the dopant is about 0.1 microseconds or greater and about 2.9 microseconds or less,

0.1 electron volts≤HOMO (dopant)−HOMO (host)≤about 0.4 electron volts, wherein the HOMO (dopant) represents a highest occupied molecular orbital (HOMO) energy level (expressed in electron volts) of the dopant, and the HOMO (host) represents, in a case where the host comprised in the emission layer comprises one type of host, a HOMO energy level (expressed in electron volts) of the one type of host; or in a case where the host comprised in the emission layer is a mixture of two or more different types of host, a highest HOMO energy level from among HOMO energy levels (expressed in electron volts) of the two or more different types of host,

the PLQY of the dopant is a PLQY of Film 1,

the decay time of the dopant is calculated from a time-resolved photoluminescence (TRPL) spectrum with respect to Film 1,

Film 1 has a thickness of 40 nanometers obtained by vacuum-deposition of the host and the dopant comprised in the emission layer in a weight ratio of 90:10 on a quartz substrate at a vacuum degree of 10 −7 torr,

the HOMO (dopant) is a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of 1,4-bis(triphenylsilyl)benzene and the dopant comprised in the emission layer in a weight ratio of 85:15 on an ITO substrate at a vacuum degree of 10 −7 torr, and

the HOMO (host) is, i) in a case where the host comprises one type of host, a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of the one type of host on an ITO substrate at a vacuum degree of 10 −7 torr; or ii) in a case where the host is a mixture of two or more different types of host, a largest negative value from among negative values measured by using a photoelectron spectrometer in an ambient atmosphere with respect to films having a thickness of 40 nanometers obtained by vacuum-deposition of each of the two or more different types of host on an ITO substrate at a vacuum degree of 10 −7 torr.

2. The organic light-emitting device of claim 1 , wherein the emission energy of a maximum emission wavelength of an emission spectrum of the dopant is about 2.31 electron volts or greater and about 2.48 electron volts or less and the emission energy of a maximum emission wavelength of an emission spectrum of the dopant is calculated from a maximum emission wavelength of an emission spectrum with respect to Film 1.

3. The organic light-emitting device of claim 1 , wherein the PLQY of the dopant is about 0.9 or greater and about 1.0 or less.

4. The organic light-emitting device of claim 1 , wherein a decay time of the dopant is about 1.0 microseconds or greater and about 2.9 microseconds or less.

5. The organic light-emitting device of claim 1 , wherein 0.1 electron volts≤HOMO (dopant)−HOMO (host)≤about 0.25 electron volts.

6. The organic light-emitting device of claim 1 , wherein

the PLQY of the dopant is about 0.975 or greater and about 1.0 or less,

the decay time of the dopant is about 2.0 microseconds or greater and about 2.5 microseconds or less, and

0.15 electron volts≤HOMO (dopant)−HOMO (host)≤about 0.25 electron volts.

7. The organic light-emitting device of claim 1 , wherein the dopant is an iridium-free organometallic compound.

8. The organic light-emitting device of claim 1 , wherein the dopant is an organometallic compound comprising 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 comprising platinum.

10. The organic light-emitting device of claim 1 , wherein the dopant has a square-planar coordination structure.

11. The organic light-emitting device of claim 1 , wherein the dopant comprises a metal M and an organic ligand, wherein the metal M and the organic ligand are capable of together forming one, two, or three cyclometalated rings.

12. The organic light-emitting device of claim 1 , wherein

the dopant comprises a metal M and a tetradentate organic ligand, wherein the metal M and the tetradentate organic ligand are capable of together forming three or four cyclometalated rings,

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.

13. The organic light-emitting device of claim 1 , wherein

the host comprises an electron transporting host and a hole transporting host,

the electron transporting host comprises at least one electron transporting moiety,

the hole transporting host does not comprise an electron transporting moiety, and

the at least one electron transporting moiety is selected from a cyano group, a π electron-depleted nitrogen-containing cyclic group, and a group represented by one of following Formulae:

wherein, in the Formulae above, *, *′, and *″ each indicate a binding site to an adjacent atom.

14. The organic light-emitting device of claim 13 , wherein

the electron transporting host comprises at least one π electron-depleted nitrogen-free cyclic group and at least one electron transporting moiety,

the hole transporting host comprises at least one π electron-depleted nitrogen-free cyclic group and does not comprise an electron transporting moiety, and

the at least one electron transporting moiety is a cyano group or a π electron-depleted nitrogen-containing cyclic group.

15. The organic light-emitting device of claim 14 , wherein

the π electron-depleted nitrogen-containing cyclic group is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinolic group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, or a condensed ring group in which at least one of the foregoing groups is condensed with at least one cyclic group, and

the π electron-depleted nitrogen-free cyclic group is a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, or a triindolobenzene group.

16. The organic light-emitting device of claim 13 , wherein

the electron transporting host comprises i) at least one selected from a cyano group, a pyrimidine group, a pyrazine group, and a triazine group and ii) a triphenylene group, and

the hole transporting host comprises a carbazole group.

17. The organic light-emitting device of claim 13 , wherein the electron transporting host comprises at least one cyano group.

18. The organic light-emitting device of claim 1 , wherein

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

the hole transport region comprises an amine-containing compound.

19. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

emission units in the number of m stacked between the first electrode and the second electrode and comprising at least one emission layer; and

charge generating layers in the number of m−1 disposed between each two adjacent emission units from among the m emission units, the each m−1 charge generating layers comprising an n-type charge generating layer and a p-type charge generating layer,

wherein m is an integer of 2 or greater,

a maximum emission wavelength of light emitted from at least one of the emission units in the number of m differs from that of light emitted from at least one of the other emission units,

the emission layer comprises a host and a dopant,

the emission layer emits a phosphorescent light,

the dopant is an organometallic compound,

a photoluminescence quantum yield (PLOY) of the dopant is about 0.8 or greater and about 1.0 or less,

a decay time of the dopant is about 0.1 microseconds or greater and about 2.9 microseconds or less,

0.1 electron volts≤HOMO (dopant)−HOMO (host)≤about 0.4 electron volts, wherein the HOMO (dopant) represents a highest occupied molecular orbital (HOMO) energy level (expressed in electron volts) of the dopant, and the HOMO (host) represents, in a case where the host comprised in the emission layer comprises one type of host, a HOMO energy level (expressed in electron volts) of the one type of host; or in a case where the host comprised in the emission layer is a mixture of two or more different types of host, a highest HOMO energy level from among HOMO energy levels (expressed in electron volts) of the two or more different types of host,

the PLQY of the dopant is a PLQY of Film 1,

the decay time of the dopant is calculated from a time-resolved photoluminescence (TRPL) spectrum with respect to Film 1,

Film 1 is a film having a thickness of 40 nanometers obtained by vacuum-deposition of the host and the dopant comprised in the emission layer in a weight ratio of 90:10 on a quartz substrate at a vacuum degree of 10 −7 torr,

the HOMO (dopant) is a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of 1,4-bis(triphenylsilyl)benzene and the dopant comprised in the emission layer in a weight ratio of 85:15 on an ITO substrate at a vacuum degree of 10 −7 torr, and

the HOMO (host) is, i) in a case where the host comprises one type of host, a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of the one type of host on an ITO substrate at a vacuum degree of 10 −7 torr; or ii) in a case where the host is a mixture of two or more different types of host, a largest negative value from among negative values measured by using a photoelectron spectrometer in an ambient atmosphere with respect to films having a thickness of 40 nanometers obtained by vacuum-deposition of each of the two or more different types of host on an ITO substrate at a vacuum degree of 10 −7 torr.

20. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

emission layers in the number of m stacked between the first electrode and the second electrode,

wherein

m is an integer of 2 or greater,

a maximum emission wavelength of light emitted from at least one of the emission layers in the number of m differs from that of light emitted from at least one of the other emission layers,

the emission layer comprises a host and a dopant,

the emission layer emits a phosphorescent light,

the dopant is an organometallic compound,

a photoluminescence quantum yield (PLOY) of the dopant is about 0.8 or greater and about 1.0 or less,

a decay time of the dopant is about 0.1 microseconds or greater and about 2.9 microseconds or less,

0.1 electron volts≤HOMO (dopant)−HOMO (host)≤about 0.4 electron volts, wherein the HOMO (dopant) represents a highest occupied molecular orbital (HOMO) energy level (expressed in electron volts) of the dopant, and the HOMO (host) represents, in a case where the host comprised in the emission layer comprises one type of host, a HOMO energy level (expressed in electron volts) of the one type of host; or in a case where the host comprised in the emission layer is a mixture of two or more different types of host, a highest HOMO energy level from among HOMO energy levels (expressed in electron volts) of the two or more different types of host,

the PLQY of the dopant is a PLQY of Film 1,

the decay time of the dopant is calculated from a time-resolved photoluminescence (TRPL) spectrum with respect to Film 1,

Film 1 is a film having a thickness of 40 nm obtained by vacuum-deposition of the host and the dopant comprised in the emission layer in a weight ratio of 90:10 on a quartz substrate at a vacuum degree of 10 −7 torr,

the HOMO (dopant) is a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of 1,4-bis(triphenylsilyl)benzene and the dopant comprised in the emission layer in a weight ratio of 85:15 on an ITO substrate at a vacuum degree of 10 −7 torr, and

the HOMO (host) is, i) in a case where the host comprises one type of host, a negative value measured by using a photoelectron spectrometer in an ambient atmosphere with respect to a film having a thickness of 40 nanometers obtained by vacuum-deposition of the one type of host on an ITO substrate at a vacuum degree of 10 −7 torr; or ii) in a case where the host is a mixture of two or more different types of host, a largest negative value from among negative values measured by using a photoelectron spectrometer in an ambient atmosphere with respect to films having a thickness of 40 nanometers obtained by vacuum-deposition of each of the two or more different types of host on an ITO substrate at a vacuum degree of 10 −7 torr.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2021
From: KWAK, SEUNGYEON; KOO, HYUN; KIM, SANGDONG; KIM, JIWHAN; LEE, SUNGHUN; CHOI, HYEONHO; HONG, SEOKHWAN; HWANG, KYUYOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 058014/0453 →
Priority Claims (2)
KR 10-2017-0113561 · Sep 5, 2017 · national
KR 10-2018-0105124 · Sep 4, 2018 · national
Continuity (1)
Related Publication 20190074468A1 · Mar 7, 2019
Cited By (5)
US 12,268,044 US 12,274,117 US 12,532,597 US 12,550,606 US 12,563,962