IP Library Granted Patent US 7,648,777
Granted Patent B2
US 7,648,777 · App. 11/336,877 · Granted Jan 19, 2010

Blue electroluminescent compound and organic electroluminescent device using the same

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Quick Facts
Patent No.
US 7,648,777
App. No.
11/336,877
Granted
Jan 19, 2010
Kind
B2
Abstract

An organic electroluminescent compound and an organic electroluminescent device using the same. The organic electroluminescent compound having Formula 1 can be used as blue electroluminescent compound. The organic electroluminescent device using the organic electroluminescent compound having Formula 1 has improved luminous efficiency and color purity.

Claims (30)

1. A compound having Formula 1:

wherein each of R 1 through R 8 and R 1 ′ through R 8 ′ is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group;

X is Se; and

Y is N or P.

2. The compound of claim 1 , wherein each of R 1 through R 8 ′ in Formula 1 is independently selected from the group consisting of Formulae (1a) through (1h):

wherein each of R 9 , R 10 , and R 11 is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group.

3. An organic electroluminescent device having an organic layer comprising the compound of claim 1 .

4. An organic electroluminescent device, comprising:

a pair of electrodes;

an organic layer between the pair of electrodes, the organic layer being a light-emitting layer comprising a phenoxazine dimer having Formula 1:

wherein each of R 1 through R 8 and R 1 ′ through R 8 ′ in Formula 1 is independently selected from the group consisting of Formulae (1a) through (1h):

wherein each of R 9 , R 10 , R 11 is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group;

X is O; and

Y is N.

5. The organic electroluminescent device of claim 4 , wherein the organic electroluminescent compound is represented by Formula 3:

6. The organic electroluminescent device of claim 4 , wherein the light-emitting layer is formed by a light-emitting layer forming composition comprising 0.01 to 20% by weight of the phenoxazine dimer having Formula 1 based on the weight of a host.

7. An organic electroluminescent device, comprising:

a first electrode;

a second electrode;

a light-emitting layer between the first electrode and the second electrode; and

optionally a hole transport layer between the light-emitting layer and the first electrode, at least one of the light-emitting layer and the optional hole transport layer formed from a phenoxazine dimer represented by Formula 2:

wherein each of R 12 , R 12 ′ and R 13 is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C5-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group; and

wherein the phenoxazine dimer is selected from the group consisting of Formulae 3 and 5 through 9:

8. A compound having Formula 1:

wherein each of R 1 through R 8 and R 1 ′ through R 8 ′ is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group;

X is O, S, or Se; and

Y is P.

9. The compound of claim 1 , wherein each of R 1 through R 8 and R 1 ′ through R 8 ′ in Formula 1 is independently selected from the group consisting of Formulae (1a) through (1h):

wherein each of R 9 , R 10 , and R 11 is independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heteroarylalkyl group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C5-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkyl ester group, and a substituted or unsubstituted C6-C30 aryl ester group.

10. An organic electroluminescent device having an organic layer comprising the compound of claim 8 .

Assignments (3)
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 Dec 18, 2008
From: SAMSUNG SDI CO., LTD.
To: SAMSUNG MOBILE DISPLAY CO., LTD.
Reel/Frame 022034/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 23, 2006
From: PARK, SANG-HOON; NOH, TAE-YONG; KWON, O-HYUN; KIM, SANG-YEOL; SON, JHUN-MO; LEE, SUNG-HUN
To: SAMSUNG SDI CO., LTD.
Reel/Frame 017502/0137 →