# US 2014/0197402 A1 · Material for organic light-emitting device, and organic light-emitting device using same

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- Number: US 2014/0197402 A1
- Document ID: US20140197402A1
- Status: Published application
- Kind: A1
- Application number: 14/240,855
- Filed: 2012-09-06
- Published: 2014-07-17
- Earliest claimed: 2011-09-09
- Assignees: LG Chem, Ltd.
- Inventors: Jungoh Huh; Tae Yoon Park; Jungi Jang; Sung Kil Hong
- Web page: https://patentgrep.com/patent/US20140197402A1

## CPC

- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/008: {Triarylamine dyes containing no other chromophores}
- C09K 11/06: containing organic luminescent materials
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- 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 50/15: Hole transporting layers
- H10K 50/156: {comprising a multilayered structure}
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present invention provides an organic light emitting device including a dibenzothiophene-based compound and an organic material layer composed of one more layers including a first electrode, a second electrode and a light emitting layer disposed between the first electrode and the second electrode, in which one or more layers of the organic material layer include the dibenzothiophene-based compound of Formula 1 or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

## Claims

### Claim 1

A dibenzothiophene-based compound represented by the following Formula 1:
Wherein L1 is an arylene group having 6 to 40 carbon atoms; or a fluorenylene group substituted with an alkyl group,
R1 is hydrogen; an alkyl group having 1 to 20 carbon atoms; an alkoxy group having 1 to 20 carbon atoms; or an aryl group having 6 to 12 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms,
R2 and R3 are the same as each other, and are each an aryl group having 10 to 16 ring-membered carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorenyl group, a carbazole group, a nitrile group, a thiophene group unsubstituted or substituted with a phenyl group, a benzothiophene group and a nitro group; a carbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorenyl group, a carbazole group, a nitrile group, a thiophene group unsubstituted or substituted with a phenyl group, a benzothiophene group and a nitro group; a thiophenyl group unsubstituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorenyl group, a carbazole group, a nitrile group, a thiophene group unsubstituted or substituted with a phenyl group, a benzothiophene group and a nitro group; or a heterocyclic group including one or more of N, S and O atoms and having 5 to 12 ring-membered carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorenyl group, a carbazole group, a nitrile group, a thiophene group unsubstituted or substituted with a phenyl group, a benzothiophene group and a nitro group,
R4 is hydrogen; an alkyl group having 1 to 20 carbon atoms; or an alkoxy group having 1 to 20 carbon atoms, and may form an aliphatic, aromatic or hetero condensed ring with an adjacent group, and
n means the number of substituents and is an integer of 1 to 6.

### Claim 2 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein R1 is hydrogen or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

### Claim 3 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein R2 and R3 are the same as each other, and are each an aryl group having 10 to 16 ring-membered carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorenyl group, a carbazole group, a nitrile group, a thiophene group unsubstituted or substituted with a phenyl group, a benzothiophene group and a nitro group.

### Claim 4 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein R2 and R3 are the same as each other, and are each a biphenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a nitrile group and a nitro group; or a phenyl group which is substituted with one or more substituents selected from the group consisting of a thiophene group unsubstituted or substituted with a phenyl group and a benzothiophene group.

### Claim 5 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein L1 is a phenylene group, a biphenylene group or a fluorenylene group unsubstituted or substituted with an alkyl group.

### Claim 6 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein L1 is a phenylene group, a biphenylene group or a fluorenylene group substituted with an alkyl group,
R1 is hydrogen, or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, and
R2 and R3 are the same as each other, and are each a biphenyl group, a phenyl group substituted with a thiophene group unsubstituted or substituted with a phenyl group, or a phenyl group substituted with benzothiophene.

### Claim 6 (depends on 1)

The dibenzothiophene-based compound of claim 1, wherein Formula 1 is any one of Formulas 1-1 to 1-9.

### Claim 8 (depends on 1)

An organic light emitting device comprising an organic material layer composed of one more layers comprising a first electrode, a second electrode and a light emitting layer disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the dibenzothiophene-based compound of claim 1 or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 9 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a hole transporting layer and the hole transporting layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 10 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a two-layered hole transporting layer and at least one layer of the hole transporting layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 11 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a first hole transporting layer and a second hole transporting layer,
the first hole transporting layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound, and
the second hole transporting layer comprises an aromatic amine compound.

### Claim 12 (depends on 11)

The organic light emitting device of claim 11, wherein the first hole transporting layer is interposed between a light emitting layer and the second hole transporting layer.

### Claim 13 (depends on 11)

The organic light emitting device of claim 11, wherein the first hole transporting layer is in contact with the light emitting layer.

### Claim 14 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a hole injection layer and the hole injection layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 15 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a layer that simultaneously injects and transports holes and the layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 16 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises an electron injection and electron transporting layer and the electron injection or electron transporting layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 17 (depends on 8)

The organic light emitting device of claim 8, wherein the organic material layer comprises a light emitting layer and the light emitting layer comprises the dibenzothiophene-based compound or a compound in which a heat curable or photo curable functional group is introduced into the dibenzothiophene-based compound.

### Claim 18 (depends on 8)

The organic light emitting device of claim 8, wherein the heat curable or photo curable functional group is a vinyl group or an acryl group.