# US 10,121,972 B2 · Composite material, light-emitting element, light-emitting device, electronic device, and lighting device

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- Number: US 10,121,972 B2
- Document ID: US10121972B2
- Status: Granted
- Kind: B2
- Application number: 15/819,231
- Filed: 2017-11-21
- Published: 2018-03-15
- Granted: 2018-11-06
- Earliest claimed: 2011-03-23
- Assignees: Semiconductor Energy Laboratory Co., Ltd.
- Applicants: Semiconductor Energy Laboratory Co., Ltd.
- Inventors: Kaori Ogita; Hiromi Nowatari; Harue Osaka; Takahiro Ushikubo; Satoshi Seo; Takako Takasu
- Web page: https://patentgrep.com/patent/US10121972B2

## CPC

- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/342: {comprising iridium}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL

## Abstract

A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite material in which light absorption due to charge-transfer interaction is unlikely to occur is provided. A composite material having a high visible-light-transmitting property is provided. A composite material including a hydrocarbon compound and an inorganic compound exhibiting an electron-accepting property with respect to the hydrocarbon compound is provided. The hydrocarbon compound has a substituent bonded to a naphthalene skeleton, a phenanthrene skeleton, or a triphenylene skeleton and has a molecular weight of 350 to 2000, and the substituent has one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

## Claims

### Claim 1

A light-emitting element comprising:
first and second electrodes;
a light-emitting layer between the first and second electrodes; and
a layer between the first electrode and the light-emitting layer,
wherein:
the layer contains an organic compound and a transition metal oxide,
a molecular weight of the organic compound is in a range of 350 or more and 2000 or less,
the organic compound has an absorption peak at shorter than 380 nm,
the organic compound has a skeleton with a substituent,
the skeleton is selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton, and
the substituent has at least one ring selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

### Claim 2 (depends on 1)

The light-emitting element according to claim 1, wherein the layer has a stacked structure of a first layer containing the organic compound and the transition metal oxide, and a second layer containing a second organic compound in contact with the first layer.

### Claim 3 (depends on 2)

The light-emitting element according to claim 2, wherein the second organic compound is the same as the organic compound.

### Claim 4 (depends on 2)

The light-emitting element according to claim 2, wherein:
the second organic compound is different from the organic compound,
a molecular weight of the second organic compound is in a range of 350 or more and 2000 or less,
the second organic compound has a second skeleton with a second substituent,
the second skeleton is selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton, and
the second substituent has at least one ring selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

### Claim 5 (depends on 1)

The light-emitting element according to claim 1, wherein the substituent is bonded to the α- or β-position of the naphthalene skeleton, the 9-position of the phenanthrene skeleton, or the 2-position of the triphenylene skeleton.

### Claim 6 (depends on 1)

The light-emitting element according to claim 1, wherein the substituent is a phenyl group.

### Claim 7 (depends on 1)

A light-emitting device comprising the light-emitting element according to claim 1.

### Claim 8

A light-emitting element comprising:
first and second electrodes;
first and second light-emitting layers between the first and second electrodes; and
a layer between the first and second light-emitting layers,
wherein:
the layer includes an organic compound and a transition metal oxide,
a molecular weight of the organic compound is in a range of 350 or more and 2000 or less,
the organic compound has an absorption peak at shorter than 380 nm,
the organic compound has a skeleton with a substituent,
the skeleton is selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton, and
the substituent has at least one ring selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

### Claim 9 (depends on 8)

The light-emitting element according to claim 8, wherein the layer has a stacked structure of a first layer containing the organic compound and the transition metal oxide, and a second layer containing a second organic compound in contact with the first layer.

### Claim 10 (depends on 9)

The light-emitting element according to claim 9, wherein the second organic compound is the same as the organic compound.

### Claim 11 (depends on 9)

The light-emitting element according to claim 9, wherein:
the second organic compound is different from the organic compound,
a molecular weight of the second organic compound is in a range of 350 or more and 2000 or less,
the second organic compound has a second skeleton with a second substituent,
the second skeleton is selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton, and
the second substituent has at least one ring selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

### Claim 12 (depends on 8)

The light-emitting element according to claim 8, wherein the substituent is bonded to the α- or β-position of the naphthalene skeleton, the 9-position of the phenanthrene skeleton, or the 2-position of the triphenylene skeleton.

### Claim 13 (depends on 8)

The light-emitting element according to claim 8, wherein the substituent is a phenyl group.

### Claim 14 (depends on 8)

A light-emitting device comprising the light-emitting element according to claim 8.