IP Library Granted Patent US 7,906,227
Granted Patent B2
US 7,906,227 · App. 12/078,734 · Granted Mar 15, 2011

Indene derivative compound and organic light emitting device comprising the same

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Quick Facts
Patent No.
US 7,906,227
App. No.
12/078,734
Granted
Mar 15, 2011
Kind
B2
Abstract

Provided are an indene derivative compound represented by Formula 1 below and an organic light emitting device including the same: X—Ar 1 —Ar 2 —Y  Formula 1 wherein Ar 1 , Ar 2 and X are described in the detailed description, and Y is represented by one of Formulae 2a to 2d: wherein R 1 to R 4 and Z are described in the detailed description. An organic light emitting device having improved driving voltage properties, brightness, efficiency and color purity can be prepared by including the indene derivative compound.

Claims (32)

1. An indene derivative compound represented by Formula 1 below:

X—Ar 1 —Ar 2 —Y  Formula 1

wherein the Ar 1 is selected from the group consisting of:

wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group and a substituted or unsubstituted C 5 -C 30 heterocycloalkyl group,

Ar 2 is selected from the group consisting of a substituted or unsubstituted C 6 -C 15 arylene group, a substituted or unsubstituted C 5 -C 15 heteroarylene group, a substituted or unsubstituted C 5 -C 15 alkenylene group and a combination of at least two of them which are connected by a single bond,

X is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 3 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 20 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 arylalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 3 -C 30 arylamino group, a substituted or unsubstituted C 3 -C 30 arylsilane group and a group represented by one of Formulae 2a through 2d, and

Y is a group represented by one of Formulae 2a through 2d:

wherein R 1 to R 4 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 3 -C 20 cycloalkyl group, a substituted or unsubstituted C 5 -C 20 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 arylalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 3 -C 30 arylamino group and a substituted or unsubstituted C 3 -C 30 arylsilane group, and Z is O or S.

2. The indene derivative compound of claim 1 , wherein the Ar 2 is selected from the group consisting of

3. The indene derivative compound of claim 1 , wherein the R 1 to R 4 and X are each independently a hydrogen atom, a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, a phenyl group, a biphenyl group, a petalenyl group, an indenyl group, a naphthyl group, a biphenylenyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a phenalenyl group, a fluorenyl group, a methylanthryl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coroneryl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a fluorenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, a cyclohexyl group, an oxyranyl group, a pyrrolidinyl group, a pyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di(C 6 -C 50 aryl)amino group, a tri(C 6 -C 50 aryl)silyl group and derivatives thereof.

4. The indene derivative compound of claim 1 , being represented by one of Formulae 3 to 24 below:

5. An organic light emitting device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an indene derivative compound according to claim 1 .

6. An organic light emitting device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an indene derivative compound according to claim 2 .

7. An organic light emitting device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an indene derivative compound according to claim 3 .

8. An organic light emitting device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises an indene derivative compound according to claim 4 .

9. The organic light emitting device of claim 5 , wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

10. The organic light emitting device of claim 6 , wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

11. The organic light emitting device of claim 7 , wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

12. The organic light emitting device of claim 8 , wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

13. The organic light emitting device of claim 5 , further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the first electrode and the second electrode.

14. The organic light emitting device of claim 9 , wherein when the organic layer is an emitting layer, the emitting layer further comprises a phosphorescent or fluorescent dopant for red, green, blue or white color.

15. The organic light emitting device of claim 14 , wherein the phosphorescent dopant is an organic metal compound comprising at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm.

16. The organic light emitting device of claim 13 , comprising a structure selected from the group consisting of first electrode/hole injection layer/emitting layer/electron transport layer/electron injection layer/second electrode, first electrode/hole injection layer/hole transport layer/emitting layer/electron transport layer/electron injection layer/second electrode and first electrode/hole injection layer/hole transport layer/emitting layer/hole blocking layer/electron transport layer/electron injection layer/second electrode.

17. The indene derivative of claim 1 , with a structure as follows:

wherein in formula 1 of claim 1 Ar 1 is unsubstituted C 14 arylene;

Ar 2 is unsubstituted C 6 arylene;

X is unsubstituted C 6 aryl; and

Y is a group represented by Formula 2b:

wherein R 1 is unsubstituted C6 aryl,

R2 is unsubstituted C6 aryl,

R3 is hydrogen, and

R4 is hydrogen.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2012
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 029093/0177 →
MERGER Recorded Sep 21, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 029241/0599 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2009
From: SAMSUNG SDI CO., LTD.
To: SAMSUNG MOBILE DISPLAY CO., LTD.
Reel/Frame 023620/0798 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2008
From: KIM,MYEONG-SUK; SHIN,DONG-WOO; KIM,YU-JIN; CHOI,BYOUNG-KI; NOH,TAE-YONG; KWON,O-HYUN; LEE,TAE-WOO; HAN,EUN-SIL; PAEK,WOON-JUNG
To: SAMSUNG ELECTRONICS CO., LTD.,; SAMSUNG SDI CO., LTD.,
Reel/Frame 021035/0886 →