IP Library Granted Patent US 9,553,270
Granted Patent B2
US 9,553,270 · App. 14/240,855 · Granted Jan 24, 2017

Material for organic light-emitting device, and organic light-emitting device using same

Inventors: Jungoh Huh (Seoul, KR); Tae Yoon Park (Daejeon, KR); Jungi Jang (Daejeon, KR); Sung Kil Hong (Daejeon, KR)
Assignee: LG CHEM, LTD.
H01L51/0052C07D307/91C09K11/06H01L51/006H01L51/0061H01L51/0073H01L51/0074H01L51/50H01L51/5012H01L51/5056H01L51/5064H01L51/5072H01L51/5088
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Quick Facts
Patent No.
US 9,553,270
App. No.
14/240,855
Granted
Jan 24, 2017
Kind
B2
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 (26)

1. A dibenzothiophene-based compound represented by the following Formula 1:

Wherein L 1 is an arylene group having 6 to 40 carbon atoms; or a fluorenylene group substituted with an alkyl group,

R 1 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,

R 2 and R 3 are the same as each other, and are each 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, 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,

R 4 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.

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

3. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 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.

4. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 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.

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

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

R 1 is hydrogen, or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, and

R 2 and R 3 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.

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

8. 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 .

9. 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.

10. 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.

11. 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, and

the second hole transporting layer comprises an aromatic amine compound.

12. 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.

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

14. 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.

15. 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.

16. 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.

17. 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2014
From: HUH, JUNGOH; PARK, TAE YOON; JANG, JUNGI; HONG, SUNG KIL
To: LG CHEM, LTD
Reel/Frame 032292/0350 →
Priority Claims (1)
KR 10-2011-0091943 · Sep 9, 2011 · national
Continuity (1)
Related Publication 20140197402A1 · Jul 17, 2014