# US 11,444,251 B2 · Organic electroluminescent element

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- Number: US 11,444,251 B2
- Document ID: US11444251B2
- Status: Granted
- Kind: B2
- Application number: 16/349,056
- Filed: 2017-10-17
- Published: 2019-09-19
- Granted: 2022-09-13
- Earliest claimed: 2016-11-29
- Assignees: Merck Patent GmbH
- Applicants: Konica Minolta, Inc.
- Inventors: Kazuhiro Oikawa; Akihiro Kimura
- Web page: https://patentgrep.com/patent/US11444251B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl
- C07D 271/107: with two aryl or substituted aryl radicals attached in positions 2 and 5
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 471/14: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07F 9/65685: {the ring phosphorus atom being part of a phosphine oxide or thioxide}
- C07F 9/657163: {the ring phosphorus atom being bound to at least one carbon atom}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6565: {Oxadiazole compounds}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/16: Electron transporting layers
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- 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}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Provided is an organic electroluminescent element having high efficiency, a long lifetime, and bending resistance. An organic electroluminescent element includes a light emitting layer and an electron transport layer adjacent to the light emitting layer between a positive electrode and a negative electrode. A host compound of the light emitting layer has an ionization potential deeper than that of a light emitting dopant of the light emitting layer by 0.3 eV or more. At least one organic compound contained in the electron transport layer has a molecular dipole moment of 6.0 debye or more.

## Claims

### Claim 1

An organic electroluminescent element comprising: a light emitting layer; and an electron transport layer adjacent to the light emitting layer between a positive electrode and a negative electrode, wherein
a host compound of the light emitting layer has an ionization potential deeper than that of a light emitting dopant of the light emitting layer by 0.3 eV or more and 2.0 eV or less, and
at least one organic compound contained in the electron transport layer has a molecular dipole moment of 8.0 debye or more and 16.0 debye or less,
wherein the organic compound is a compound represented by the following general formula (1):
wherein Z1 and Z2 each represent a pyridine ring which may have a substituent, Z3 represents a simple bond, and R101 represents an aryl group which may have a substituent or an aromatic heterocyclic group which may have a substituent.

### Claim 2 (depends on 1)

The organic electroluminescent element according to claim 1, wherein the molecular dipole moment of the organic compound is 10.0 debye or more and 16.0 debye or less.

### Claim 3 (depends on 1)

The organic electroluminescent element according to claim 1, wherein the molecular dipole moment of the organic compound is 12.0 debye or more and 16.0 debye or less.

### Claim 4 (depends on 1)

The organic electroluminescent element according to claim 1, wherein the organic compound is a compound represented by general formula (1), containing only carbon, nitrogen, and hydrogen.

### Claim 5 (depends on 1)

The organic electroluminescent element according to claim 1, wherein a whole of constituent layers of the organic electroluminescent element contains a polar fluorinated solvent in an amount of 1000 ppm by mass or less.

### Claim 6 (depends on 5)

The organic electroluminescent element according to claim 5, wherein the polar fluorinated solvent is any one or more selected from a fluorinated alcohol, a fluorinated ester, and a fluorinated ether.

### Claim 7 (depends on 5)

The organic electroluminescent element according to claim 5, wherein the polar fluorinated solvent contains a fluorinated alcohol having 3 to 5 carbon atoms.

### Claim 8 (depends on 1)

The organic electroluminescent element according to claim 1, wherein the light emitting layer is formed of a compound having a molecular weight of 500 or more and 3,000 or less.

### Claim 9 (depends on 1)

The organic electroluminescent element according to claim 1, wherein the light emitting layer has a film thickness of 50 nm or more and 5 μm or less.

### Claim 10 (depends on 2)

The organic electroluminescent element according to claim 2, wherein a whole of constituent layers of the organic electroluminescent element contains a polar fluorinated solvent in an amount of 1000 ppm by mass or less.

### Claim 11 (depends on 2)

The organic electroluminescent element according to claim 2, wherein the light emitting layer is formed of a compound having a molecular weight of 500 or more and 3,000 or less.

### Claim 12 (depends on 2)

The organic electroluminescent element according to claim 2, wherein the light emitting layer has a film thickness of 50 nm or more and 5 μm or less.

### Claim 13 (depends on 3)

The organic electroluminescent element according to claim 3, wherein a whole of constituent layers of the organic electroluminescent element contains a polar fluorinated solvent in an amount of 1000 ppm by mass or less.

### Claim 14 (depends on 3)

The organic electroluminescent element according to claim 3, wherein the light emitting layer is formed of a compound having a molecular weight of 500 or more and 3,000 or less.

### Claim 15 (depends on 3)

The organic electroluminescent element according to claim 3, wherein the light emitting layer has a film thickness of 50 nm or more and 5 μm or less.