IP Library › Granted Patent US 11,482,678
Granted Patent B2
US 11,482,678 · App. 16/742,844 · Granted Oct 25, 2022

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.
H01L51/0061C07D209/88C09K11/06H01L27/3211H01L27/3248H01L51/006H01L51/5206H01L51/5218H01L51/5221H01L51/5234H05B33/14C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/185C09K2323/00H01L27/3209H01L51/0052H01L51/0058H01L51/0072H01L51/5016H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L2251/301H01L2251/308H01L2251/558Y10S428/917Y10T428/31504
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Quick Facts
Patent No.
US 11,482,678
App. No.
16/742,844
Granted
Oct 25, 2022
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 (90)

1. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a layer comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the layer having a second region formed under the green emission layer, a thickness of the second region being in the range of 1,400 to 1,800 Å, the layer being between the first electrode and the emission layer:

R 6 , R 7 , and R 8 independently being 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 2 -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 independently being a substituted or unsubstituted C 6 -C 30 aryl group or a substituted or unsubstituted C 2 -C 30 heteroaryl group,

each Y independently being 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 2 -C 30 hetero ring, and

each n independently being an integer from 0 to 5.

2. The organic light emitting device of claim 1 , wherein the compound represented by Formula 3 comprises a compound represented by Formula 3a:

R 6 , R 7 and R 8 independently being 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 2 -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; and

Q 4 being one selected from the group consisting of a hydrogen atom, a cyano group, a fluorine atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 hetero ring, and a substituted or unsubstituted amino group.

3. The organic light emitting device of claim 1 , wherein the compound represented by Formula 3 is any one of Compounds 46 through 62:

4. The organic light emitting device of claim 1 , wherein the compound represented by Formula 3 is Compound 56:

5. The organic light emitting device of claim 1 , wherein the layer comprising said at least one compound selected from the group of compounds 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.

6. The organic light emitting device of claim 1 , wherein the layer comprising said at least one compound selected from the group of compounds represented by Formula 3 is a hole injection layer or a hole transport layer.

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

8. The display device of claim 7 , 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.

9. The organic light emitting device of claim 1 , the first electrode being disposed on the substrate and being a reflective electrode, the second electrode being a semitransparent or transparent electrode, and light generated in the organic layer passes through the second electrode.

10. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a layer comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the layer having a second region formed under the green emission layer, a thickness of the second region being in the range of 1,400 to 1,800 Å, the layer being between the first electrode and the emission layer:

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

11. The organic light emitting device of claim 10 , wherein R 6 and R 7 are each a methyl group and R 8 is a phenyl.

12. The organic light emitting device of claim 11 , wherein the compound represented by Formula 3 has the following chemical structure:

13. The organic light emitting device of claim 10 , wherein the first electrode is formed on the substrate and is a reflective electrode, the second electrode is a semitransparent or transparent electrode, and light generated in the organic layer passes through the second electrode.

14. The organic light emitting device of claim 10 , 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.

15. A display device comprising the organic light emitting device of claim 10 .

16. The display device of claim 15 , 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.

17. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a region comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the region having a second region formed under the green emission layer, a thickness of the second region being in the range of 1,400 to 1,800 Å, the region being between the first electrode and the emission layer:

R 6 , R 7 , and R 8 independently being 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 2 -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 independently being a substituted or unsubstituted C 6 -C 30 aryl group or a substituted or unsubstituted C 2 -C 30 heteroaryl group,

each Y independently being 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 2 -C 30 hetero ring, and

each n independently being an integer from 0 to 5.

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

19. The display device of claim 18 , 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.

20. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a region comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the region having a second region formed under the green emission layer, a thickness of the second region being in the range of 1,400 to 1,800 Å, the region being between the first electrode and the emission layer:

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

21. A display device comprising the organic light emitting device of claim 20 .

22. The display device of claim 21 , 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.

23. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a region comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the region having a second region formed under the green emission layer, the region further comprising a hole transporting layer, a total thickness of the second region and the hole transporting layer being in the range of 1,600 to 2,000 Å, the region being between the first electrode and the emission layer:

R 6 , R 7 , and R 8 independently being 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 2 -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 independently being a substituted or unsubstituted C 6 -C 30 aryl group or a substituted or unsubstituted C 2 -C 30 heteroaryl group,

each Y independently being 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 2 -C 30 hetero ring, and

each n independently being an integer from 0 to 5.

24. A display device comprising the organic light emitting device of claim 23 .

25. The display device of claim 24 , 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.

26. An organic light emitting device, comprising:

a substrate;

a first electrode;

a second electrode, the first electrode is a reflective electrode, or the second electrode is a reflective electrode, the remaining being semitransparent or transparent electrodes; and

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

an emission layer comprising a green emission layer; and

a region comprising at least one compound selected from the group consisting of compounds represented by Formula 3, the region having a second region formed under the green emission layer, the region further comprising a hole transporting layer, a total thickness of the second region and the hole transporting layer being in the range of 1,600 to 2,000 Å, the region being between the first electrode and the emission layer:

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

27. A display device comprising the organic light emitting device of claim 26 .

28. The display device of claim 27 , 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 (10)
Continuation 16260111 · Jan 29, 2019
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 20200152884A1 · May 14, 2020
Cited By (1)
US 12,289,990