# US 2014/0191206 A1 · Organic Light-Emitting Device Having Improved Efficiency Characteristics and Organic Light-Emitting Display Apparatus Including the Same

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- Number: US 2014/0191206 A1
- Document ID: US20140191206A1
- Status: Published application
- Kind: A1
- Application number: 13/940,169
- Filed: 2013-07-11
- Published: 2014-07-10
- Earliest claimed: 2013-01-04
- Assignees: Samsung Display Co., Ltd.
- Inventors: Hwan-Hee Cho
- Web page: https://patentgrep.com/patent/US20140191206A1

## CPC

- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/16: Electron transporting layers
- H10K 50/181: {Electron blocking layers}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 2101/10: Triplet emission
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- H10K 2102/351: {Thickness}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic light-emitting device includes: a first electrode, a second electrode facing the first electrode, a phosphorescent emission layer between the first electrode and the second electrode, an electron transportation layer between the phosphorescent emission layer and the second electrode, an electron control layer between the phosphorescent emission layer and the electron transportation layer, and an electron blocking layer between the phosphorescent emission layer and the first electrode. An organic light-emitting display apparatus includes the organic light-emitting device.

## Claims

### Claim 1

An organic light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode,
a phosphorescent emission layer between the first electrode and the second electrode,
an electron transportation layer between the phosphorescent emission layer and the second electrode, and
an electron control layer between the phosphorescent emission layer and the electron transportation layer;
wherein:
the phosphorescent emission layer comprises a host material and a dopant material, and the electron control layer comprises an electron control material and a phosphorescent dopant;
a highest occupied molecular orbital (HOMO) energy level (EHH) of the host material, a lowest unoccupied molecular orbital (LUMO) energy level (ELH) of the host material, a highest occupied molecular orbital energy level (EHC) of the electron control material, and a lowest unoccupied molecular orbital energy level (ELC) of the electron control material satisfy |EHH−EHC|≦0.3 eV and |ELH−ELC|≦0.5 eV; and
a thickness of the electron control layer is in a range of about 10 to about 450.

### Claim 2

An organic light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode,
a phosphorescent emission layer between the first electrode and the second electrode,
an electron transportation layer between the phosphorescent emission layer and the second electrode,
an electron control layer between the phosphorescent emission layer and the electron transportation layer, and
an electron blocking layer between the phosphorescent emission layer and the first electrode;
wherein:
the phosphorescent emission layer comprises a host material and a dopant material, the electron control layer comprises an electron control material and a phosphorescent dopant, and the electron blocking layer comprises an electron blocking material;
a highest occupied molecular orbital energy level (EHH) of the host material, a lowest unoccupied molecular orbital energy level (ELH) of the host material, a highest occupied molecular orbital energy level (EHC) of the electron control material, a lowest unoccupied molecular orbital energy level (ELC) of the electron control material, and a lowest unoccupied molecular orbital energy level (ELB) of the electron blocking material satisfy |EHH−EHC|≦0.3 eV, |ELH−ELC|≦0.5 eV, and ELB>ELH; and
a thickness of the electron control layer is in a range of about 10 to about 450.

### Claim 3 (depends on 1)

The organic light-emitting device of claim 1, wherein a highest occupied molecular orbital energy level (EHH) of the host material, a lowest unoccupied molecular orbital energy level (ELH) of the host material, a highest occupied molecular orbital energy level (EHC) of the electron control material, and a lowest unoccupied molecular orbital energy level (ELC) of the electron control material satisfy 0≦EHH−EHC≦0.3 eV and 0≦ELH−ELC≦5 eV.

### Claim 4 (depends on 1)

The organic light-emitting device of claim 1, wherein electron mobility of the electron control material is equal to or higher than hole mobility of the electron control material.

### Claim 5 (depends on 1)

The organic light-emitting device of claim 1, wherein the highest occupied molecular orbital energy level (EHC) of the electron control material is in a range of about −5.2 eV to about −6.1 eV.

### Claim 6 (depends on 1)

The organic light-emitting device of claim 1, wherein the lowest unoccupied molecular orbital energy level (ELC) of the electron control material is in a range of about −2.5 eV to about −3.2 eV.

### Claim 7 (depends on 1)

The organic light-emitting device of claim 1, wherein a thickness of the electron control layer is in a range of about 30 Å to about 150 Å.

### Claim 8 (depends on 1)

The organic light-emitting device of claim 1, wherein the phosphorescent emission layer is a blue phosphorescent emission layer, a red phosphorescent emission layer, or a green phosphorescent emission layer.

### Claim 9 (depends on 2)

The organic light-emitting device of claim 2, wherein a thickness of the electron blocking layer is in a range of about 10 to about 1000.

### Claim 10 (depends on 2)

The organic light-emitting device of claim 2, wherein the electron blocking material comprises at least one of a triphenylamine derivative, a carbazole derivative, or a spirodifluorene derivative.

### Claim 11 (depends on 1)

The organic light-emitting device of claim 1, wherein the electron control material comprises a compound represented by Formula 1:
wherein:
R1 to R7 are each independently hydrogen, deuterium, halogen, a hydroxyl group, a cyano group, a nitro group, an amino group, carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, or a substituted or unsubstituted C6-C30 aryl group;
Ar1, Ar2, and Ar3 are each independently a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C2-C30 heteroaryl group, or a group represented by —N(Q1)(Q2),
Q1 and Q2 are each independently hydrogen, deuterium, halogen, a hydroxyl group, a cyano group, an amino group, a nitro group, carboxyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylthio group, or a substituted or unsubstituted C2-C30 heteroaryl group,
L1, L2 and L3 are each independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group, and
a, b and c are each independently an integer of 0 to 3.

### Claim 12 (depends on 1)

The organic light-emitting device of claim 1, wherein the electron control material comprises at least one compound represented by one of Formulae 2 or 3:
wherein:
R1 to R12 and R21 to R28 are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted pyrenyl group,
Ar1, Ar2, and Ar3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted bipyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiopenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzocarbazolyl group,
L1, L2 and L3 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted picenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted pentacenylene group, a substituted or unsubstituted hexacenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted imidazolinylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted purinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted indolizinylene group, a substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted phenanthridinylene group, a substituted or unsubstituted pyranylene group, a substituted or unsubstituted chromenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted isoxazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzopuranylene group, a substituted or unsubstituted triazinylene group, or a substituted or unsubstituted oxadiazolylene group, and
a, b, and c are each independently an integer of 0 to 1.

### Claim 13 (depends on 1)

The organic light-emitting device of claim 1, wherein the electron control material comprises at least one of Compounds 1 or 2 below:

### Claim 14 (depends on 1)

The organic light-emitting device of claim 1, wherein the phosphorescent dopant of the electron control material is an Ir complex, a Pt complex, a Pd complex, or an Os complex.

### Claim 15 (depends on 1)

The organic light-emitting device of claim 1, wherein the phosphorescent dopant of the electron control material is any one of the following compounds:

### Claim 16 (depends on 1)

The organic light-emitting device of claim 1, wherein the host material comprises a bipolar compound comprising a hole transportation unit and an electron transportation unit.

### Claim 17 (depends on 1)

The organic light-emitting device of claim 1, wherein the host material comprises a mixture of a bipolar compound having a hole transportation unit and an electron transportation unit, and a compound having at least a hole transportation unit.

### Claim 18 (depends on 1)

The organic light-emitting device of claim 1, wherein the electron control material comprises a compound represented by Formula 4:
<Formula 4>
wherein:
R31 to R42 are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted pyrenyl group,
Ar11 and Ar12 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted bipyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted isooxazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzooxazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzocarbazolyl group,
L11, L12, and L13 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted picenylene group, a substituted or unsubstituted perylenylene group, a substituted or unsubstituted pentacenylene group, a substituted or unsubstituted hexacenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted imidazolinylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted purinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted indolizinylene group, a substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted phenanthridinylene group, a substituted or unsubstituted pyranylene group, a substituted or unsubstituted chromenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted isoxazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted triazinylene group, or a substituted or unsubstituted oxadiazolylene group, and
p, q, and r are each independently an integer of 0 to 1.

### Claim 19 (depends on 18)

The organic light-emitting device of claim 18, wherein the electron transportation layer further comprises a metal complex represented by Formula 5:
M+L− <Formula 5>
wherein:
M is an alkali metal; and
L is an aromatic compound selected from selected from the group consisting of anthracene, naphthalene, diphenylanthracene, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, quinolinol, benzoquinolinol, acridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfluorene, bipyridyl, phenanthroline, phthalocyanine, porphyrin, and derivatives thereof.

### Claim 20 (depends on 1)

An organic light-emitting display apparatus comprising:
a transistor comprising a source, a drain, a gate, and an active layer; and
the organic light-emitting device of claim 1, wherein the first electrode of the organic light-emitting device is electrically connected to the source or the drain of the transistor.