IP Library Granted Patent US 10,573,821
Granted Patent B2
US 10,573,821 · App. 16/260,111 · Granted Feb 25, 2020

Phenylcarbazole-based compounds and fluorene-based compounds and organic light emitting device and flat panel display device comprising the same

Inventors: Seok-Hwan Hwang (Yongin-si, KR); Young-Kook Kim (Yongin-si, KR); Yoon-Hyun Kwak (Yongin-si, KR); Jong-Hyuk Lee (Yongin-si, KR); Kwan-Hee Lee (Yongin-si, KR); Min-Seung Chun (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0061C07D209/88C09K11/06H01L27/3211H01L27/3248H01L51/006H01L51/5206H01L51/5218H01L51/5221H01L51/5234H05B33/14C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/185H01L27/3209H01L51/0052H01L51/0058H01L51/0072H01L51/5016H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L2251/301H01L2251/308H01L2251/558Y10S428/917Y10T428/10Y10T428/31504
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Quick Facts
Patent No.
US 10,573,821
App. No.
16/260,111
Granted
Feb 25, 2020
Kind
B2
Abstract

An organic light emitting device including: a substrate; a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including an emission layer, wherein one of the first electrode and the second electrode is a reflective electrode and the other is a semitransparent or transparent electrode, and wherein the organic layer includes a layer having at least one of the compounds having at least one carbazole group, and a flat panel display device including the organic light emitting device. The organic light emitting device has low driving voltage, excellent current density, high brightness, excellent color purity, high efficiency, and long lifetime.

Claims (50)

1. An organic light emitting device comprising:

a substrate;

a first electrode;

a second electrode; and

an organic layer interposed between the first electrode and the second electrode, the organic layer comprising an emission layer,

the organic layer comprising a layer comprising a compounds represented by Formula 3:

where R 6 , R 7 and R 8 are each independently one selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 4 -C 30 hetero ring, a substituted or unsubstituted C 5 -C 30 polycyclic condensed ring, a hydroxy group, a cyano group, and a substituted or unsubstituted amino group, wherein two or more of R 6 , R 7 and R 8 can be optionally bound with one another to form a saturated or unsaturated carbon ring;

Ar 3 is a biphenyl group;

each Y is independently one selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 hetero ring; and

each n of the Yn between the carbazole and the nitrogen is 1, and n of the Yn between the fluorene and the nitrogen is 0.

2. The organic light emitting device of claim 1 , wherein R 6 and R 7 are each a methyl group and R 8 is a phenyl.

3. The organic light emitting device of claim 1 , wherein the compound represented by Formula 3 has the following chemical structure:

4. The organic light emitting device of claim 1 , wherein the layer comprising the compound represented by Formula 3 is one of a hole injection layer, a hole transport layer, and a single layer having hole injecting and transporting properties.

5. The organic light emitting device of claim 1 , wherein the layer comprising the compound represented by Formula 3 is a hole injection layer.

6. The organic light emitting device of claim 5 , wherein the emission layer comprises a red emission region, and a thickness of a first region of the hole injection layer under the red emission region is in a range of 1,600 to 2,200 Å.

7. The organic light emitting device of claim 5 , wherein the emission layer comprises a green emission region, and a thickness of a second region of the hole injection layer under the green emission region is in a range of 1,400 to 1,800 Å.

8. The organic light emitting device of claim 5 , wherein the emission layer comprises a blue emission region, and a thickness of a third region of the hole injection layer under the blue emission region is in a range of 1,000 to 1,400 Å.

9. The organic light emitting device of claim 5 , wherein the emission layer comprises a red emission region, a blue emission region and a green emission region;

the hole injection layer comprises a first region under the red emission region, a second region under the green emission region and a third region under the blue emission region; and

a thickness of the first region is in a range of 1,600 to 2,200 Å, a thickness of the second region is in a range of 1,400 to 1,800 Å, and a thickness of the third region is in a range of 1,000 to 1,400 Å.

10. The organic light emitting device of claim 5 , wherein the organic layer further comprises a hole transport layer.

11. The organic light emitting device of claim 10 , wherein the emission layer comprises a red emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the red emission region is in a range of 2,000 to 2,400 Å.

12. The organic light emitting device of claim 11 , wherein a thickness of the region of the hole injection layer under the red emission region is in a range of 1,600 to 2,200 Å.

13. The organic light emitting device of claim 10 , wherein the emission layer comprises a green emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the green emission region is in a range of 1,600 to 2,000 Å.

14. The organic light emitting device of claim 13 , wherein a thickness of the region of the hole injection layer under the green emission region is in a range of 1,400 to 1,800 Å.

15. The organic light emitting device of claim 10 , wherein the emission layer comprises a blue emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the blue emission region is in a range of 1,200 to 1,600 Å.

16. The organic light emitting device of claim 15 , wherein a thickness of the region of the hole injection layer under the blue emission region is in a range of 1,000 to 1,400 Å.

17. A display device comprising the organic light emitting device of claim 1 .

18. The display device of claim 17 , wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

19. An organic light emitting device comprising:

a substrate;

a first electrode;

a second electrode; and

an organic layer interposed between the first electrode and the second electrode, the organic layer comprising:

an emission layer comprising at least one of a red emission region, a green emission region and a blue emission region; and

a layer comprising a compound represented by Formula 3, the layer having at least one of a first region under the red emission region, a second region under the green emission region and a third region under the blue emission region, a thickness of the first region being in a range of 1,600 to 2,200 Å, a thickness of the second region being in a range of 1,400 to 1,800 Å, a thickness of the third region being in a range of 1,000 to 1,400 Å:

where R 6 , R 7 and R 8 are each independently one selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 4 -C 30 hetero ring, a substituted or unsubstituted C 5 -C 30 polycyclic condensed ring, a hydroxy group, a cyano group, and a substituted or unsubstituted amino group, wherein two or more of R 6 , R 7 and R 8 can be optionally bound with one another to form a saturated or unsaturated carbon ring;

Ar 3 is a biphenyl group;

each Y is independently one selected from the group consisting of a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, and a substituted or unsubstituted C 4 -C 30 hetero ring; and

each n of the Yn between the carbazole and the nitrogen is 1, and n of the Yn between the fluorene and the nitrogen is 0.

20. The organic light emitting device of claim 19 , wherein R 6 and R 7 are each a methyl group and R 5 is a phenyl.

21. The organic light emitting device of claim 19 , wherein the compound represented by Formula 3 has the following chemical structure:

22. The organic light emitting device of claim 19 , wherein the layer comprising the compound represented by Formula 3 is one of a hole injection layer, a hole transport layer, and a single layer having hole injecting and transporting properties.

23. The organic light emitting device of claim 19 , wherein the layer comprising the compound represented by Formula 3 is a hole injection layer.

24. The organic light emitting device of claim 23 , wherein the organic layer further comprises a hole transport layer.

25. The organic light emitting device of claim 24 , wherein the emission layer comprises a red emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the red emission region is in a range of 2,000 to 2,400 Å.

26. The organic light emitting device of claim 24 , wherein the emission layer comprises a green emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the green emission region is in a range of 1,600 to 2,000 Å.

27. The organic light emitting device of claim 24 , wherein the emission layer comprises a blue emission region, and a total thickness of a region of the hole transport layer and the hole injection layer under the blue emission region is in a range of 1,200 to 1,600 Å.

28. A display device comprising the organic light emitting device of claim 19 .

29. The display device of claim 28 , wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

Priority Claims (4)
KR 10-2004-0022877 · Apr 2, 2004 · national
KR 10-2004-0054700 · Jul 14, 2004 · national
KR 10-2004-0098747 · Nov 29, 2004 · national
KR 10-2006-0048306 · May 29, 2006 · national
Continuity (9)
Continuation 15871007 · Jan 14, 2018
Continuation 15266959 · Sep 15, 2016
Continuation 14607326 · Jan 28, 2015
Continuation 13439586 · Apr 4, 2012
Continuation 11806039 · May 29, 2007
Continuation In Part 11286421 · Nov 25, 2005
Continuation In Part 11181706 · Jul 13, 2005
Continuation In Part 11097182 · Apr 4, 2005
Related Publication 20190157568A1 · May 23, 2019