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

Patent metadata

Field	Value
Publication number	US-9716232-B2
Application number	US-201214240702-A
Country	US
Kind code	B2
Filing date	Sep 6, 2012
Priority date	Sep 9, 2011
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

The present specification provides an organic light emitting device comprising: a first electrode, a second electrode, and organic material layers formed of one or more layers comprising a light emitting layer disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound of Formula 1, or a compound in which a heat-curable or photocurable functional group is introduced into this compound.

First claim

The invention claimed is:

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 by 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 substituted or unsubstituted by 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 different from each other,
R 2 is a phenyl group substituted or unsubstituted by one or more substituent groups 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 nitrile group, and a nitro group; or a biphenyl group substituted or unsubstituted by one or more substituent groups 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 nitrile group, and a nitro group,
R 3 is a p-terphenyl group substituted or unsubstituted by one or more substituent groups 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 nitrile group, and a nitro group; a p-tetraphenyl group substituted or unsubstituted by one or more substituent groups 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 nitrile group, and a nitro group; or a naphthyl group substituted or unsubstituted by one or more substituent groups 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 nitrile 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 condensated cycle with an adjacent group, and
n means the number of substituent groups, 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 substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms.

3. The dibenzothiophene-based compound of claim 1 , wherein R 2 is a phenyl group; or a biphenyl group.

4. The dibenzothiophene-based compound of claim 1 , wherein R 3 is a p terphenyl group or a p tetraphenyl group.

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

6. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 are different from each other, R 2 is a phenyl group, and R 3 is a p terphenyl group.

7. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 are different from each other, R 2 is a biphenyl group, and R 3 is a p terphenyl group.

8. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 are different from each other, R 2 is a phenyl group, and R 3 is a p tetraphenyl group.

9. The dibenzothiophene-based compound of claim 1 , wherein R 2 and R 3 are different from each other, R 2 is a biphenyl group, and R 3 is a p tetraphenyl group.

10. The dibenzothiophene-based compound of claim 1 , wherein L 1 is a phenylene group, a biphenylene group, or a fluorenylene group substituted by an alkyl group, R 1 is hydrogen, or a phenyl group substituted or unsubstituted by an alkyl group having 1 to 20 carbon atoms, R 2 and R 3 are different from each other, R 2 is a phenyl group or a biphenyl group, and R 3 is a p terphenyl group or a p tetraphenyl group.

11. The dibenzothiophene-based compound of claim 1 , wherein Formula 1 is any one of the following Formulas 1-1 to 1-8

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

13. The organic light emitting device of claim 12 , wherein the organic material layers comprise a hole transport layer, and the hole transport layer comprises the dibenzothiophene-based compound.

14. The organic light emitting device of claim 12 , wherein the organic material layers comprise a first hole transport layer and a second hole transport layer, the first hole transport layer comprises the dibenzothiophene-based compound and the second hole transport layer comprises an aromatic amine compound.

15. The organic light emitting device of claim 14 , wherein the first hole transport layer is interposed between the light emitting layer and the second hole transport layer.

16. The organic light emitting device of claim 14 , wherein the first hole transport layer is in contact with the light emitting layer.

17. The organic light emitting device of claim 12 , wherein the organic material layers comprise a hole injection layer, or a layer simultaneously injecting and transporting holes and the hole injection layer and the layer simultaneously injecting and transporting holes comprises the dibenzothiophene-based compound.

18. The organic light emitting device of claim 12 , wherein the organic material layers comprise an electron injection and electron transport layer, and the electron injection or electron transport layer comprises the dibenzothiophene-based compound.

19. The organic light emitting device of claim 12 , wherein the organic material layers comprise the light emitting layer, and the light emitting layer comprises the dibenzothiophene-based compound, or the compound in which the heat curable or photocurable functional group is introduced into the dibenzothiophene based compound.

Assignees

• Huh Jungoh
• Park Tae Yoon
• Jang Jungi
• Hong Sung Kil
• Lg Chemical Ltd

Inventors

• Huh Jungoh
• Park Tae Yoon
• Jang Jungi
• Hong Sung Kil

Classifications

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L51/0052 Primary

  Electricity · mapped topic