IP Library Granted Patent US 7,754,349
Granted Patent B2
US 7,754,349 · App. 11/947,985 · Granted Jul 13, 2010

Silanylamine-based compound and organic light-emitting device including organic layer including the silanylamine-based compound

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Quick Facts
Patent No.
US 7,754,349
App. No.
11/947,985
Granted
Jul 13, 2010
Kind
B2
Abstract

A silanylamine-based compound is represented by Formula 1 below. An organic light-emitting device includes an organic layer that includes the silanylamine-based compound: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ar 1 , Ar 2 , and Ar 3 are as defined in the specification. The silanylamine-based compound has good electrical characteristics and charge transport capability, and thus, is useful as a hole injection material, a hole transport material, and/or an emitting material for fluorescent or phosphorescent devices capable of producing light of a full spectrum of colors, including red, green, blue, and white. Thus, the organic light-emitting device including the organic layer including the silanylamine-based compound shows high efficiency, a low driving voltage, and high brightness.

Claims (35)

1. A silanylamine-based compound represented by Formula 1 below:

wherein,

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 5 -C 30 aryloxy group, a substituted or unsubstituted C 5 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group, and adjacent groups selected from R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may optionally join together to form a saturated or unsaturated carbon ring; and

Ar 1 , Ar 2 , and Ar 3 are each independently hydrogen, a substituted or unsubstituted C 5 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group.

2. The silanylamine-based compound of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted C 5 -C 12 aryl group or a substituted or unsubstituted C 3 -C 15 heteroaryl group.

3. The silanylamine-based compound of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a phenyl group, a C 1 -C 5 alkylphenyl group, a C 1 -C 5 alkoxyphenyl group, a cyanophenyl group, a phenoxyphenyl group, a halophenyl group, a naphthyl group, a C 1 -C 5 alkylnaphthyl group, a C 1 -C 5 alkoxynaphthyl group, a cyanonaphthyl group, a halonaphthyl group, a fluorenyl group, a carbazolyl group, a C 1 -C 5 alkylcarbazolyl group, a biphenyl group, a C 1 -C 5 alkylbiphenyl group, a C 1 -C 5 alkoxybiphenyl group, or a pyridyl group.

4. The silanylamine-based compound of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a fluorenyl group, a carbazolyl group, a phenyl group, a naphthyl group, a biphenyl group, or an aryl group that is substituted by one, two, or three selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyano, phenoxy, phenyl, and halogen.

5. The silanylamine-based compound of claim 1 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently selected from the group consisting of a phenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-, m-, or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, and p-tolyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a pentalenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a fluorenyl group, an anthraquinolyl group, a phenanthryl group, a triphenylene group, a pentaphenyl group, a hexaphenyl group, and a carbazolyl group.

6. The silanylamine-based compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 6 -C 12 aryl group, a substituted or unsubstituted C 6 -C 12 aryloxy group, or a C 3 -C 12 heteroaryl group.

7. The silanylamine-based compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently a C 1 -C 10 alkyl group, a phenyl group, a halophenyl group, a cyanophenyl group, a C 1 -C 10 alkylphenyl group, a C 1 -C 10 alkoxyphenyl group, a biphenyl group, a halobiphenyl group, a naphthyl group, a halonaphthyl group, a C 1 -C 10 alkylnaphthyl group, or a C 1 -C 10 alkoxynaphthyl group.

8. The silanylamine-based compound of claim 1 , which is a compound 1, 4, 11, 21, or 22 below:

9. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

one or more organic layers interposed between the first electrode and the second electrode, wherein at least one of the one or more organic layers comprises the silanylamine-based compound of claim 1 .

10. The organic light-emitting device of claim 9 , wherein the organic layer comprising the silanylamine-based compound is a hole injection layer or a hole transport layer.

11. The organic light-emitting device of claim 9 , wherein the organic layer comprising the silanylamine-based compound is a single layer having hole injection capability and hole transport capability.

12. The organic light-emitting device of claim 10 , wherein the organic light-emitting device has one of the following structures:

first electrode/hole injection layer/emitting layer/second electrode;

first electrode/hole injection layer/hole transport layer/emitting layer/electron transport layer/second electrode; or

first electrode/hole injection layer/hole transport layer/emitting layer/electron transport layer/electron injection layer/second electrode structure.

13. The organic light-emitting device of claim 12 , further comprising at least one of a hole blocking layer and an electron blocking layer.

14. The organic light-emitting device of claim 11 , wherein the organic light-emitting device has one of the following structures:

first electrode/single layer having hole injection capability and hole transport capability/emitting layer/electron transport layer/second electrode or

first electrode/single layer having hole injection capability and hole transport capability/emitting layer/electron transport layer/electron injection layer/second electrode.

15. The organic light-emitting device of claim 14 , further comprising at least one of a hole blocking layer and an electron blocking layer.

16. The organic light-emitting device of claim 9 , wherein the organic layer comprising the silanylamine-based compound is an emitting layer.

17. The organic light-emitting device of claim 16 , wherein the emitting layer further comprises a phosphorescent or fluorescent material.

18. The organic light-emitting device of claim 9 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted C 5 -C 12 aryl group or a substituted or unsubstituted C 3 -C 15 heteroaryl group.

19. The organic light-emitting device of claim 9 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a phenyl group, a C 1 -C 5 alkylphenyl group, a C 1 -C 5 alkoxyphenyl group, a cyanophenyl group, a phenoxyphenyl group, a halophenyl group, a naphthyl group, a C 1 -C 5 alkylnaphthyl group, a C 1 -C 5 alkoxynaphthyl group, a cyanonaphthyl group, a halonaphthyl group, a fluorenyl group, a carbazolyl group, a C 1 -C 5 alkylcarbazolyl group, a biphenyl group, a C 1 -C 5 alkylbiphenyl group, a C 1 -C 5 alkoxybiphenyl group, or a pyridyl group.

20. The organic light-emitting device of claim 9 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently a fluorenyl group, a carbazolyl group, a phenyl group, a naphthyl group, a biphenyl group, or an aryl group that is substituted by one, two, or three selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyano, phenoxy, phenyl, and halogen.

21. The organic light-emitting device of claim 9 , wherein Ar 1 , Ar 2 , and Ar 3 are each independently selected from the group consisting of a phenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-, m-, or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-, and p-tolyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a pentalenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a fluorenyl group, an anthraquinolyl group, a phenanthryl group, a triphenylene group, a pentaphenyl group, a hexaphenyl group, and a carbazolyl group.

22. The organic light-emitting device of claim 9 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 6 -C 12 aryl group, a substituted or unsubstituted C 6 -C 12 aryloxy group, or a C 3 -C 12 heteroaryl group.

23. The organic light-emitting device of claim 9 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently a C 1 -C 10 alkyl group, a phenyl group, a halophenyl group, a cyanophenyl group, a C 1 -C 10 alkylphenyl group, a C 1 -C 10 alkoxyphenyl group, a biphenyl group, a halobiphenyl group, a naphthyl group, a halonaphthyl group, a C 1 -C 10 alkylnaphthyl group, or a C 1 -C 10 alkoxynaphthyl group.

24. The organic light-emitting device of claim 9 , wherein the silanylamine-based compound is which is a compound 1, 4, 11, 21, or 22 below:

Assignments (1)
MERGER Recorded Sep 21, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 029241/0599 →