IP Library Granted Patent US 8,367,219
Granted Patent B2
US 8,367,219 · App. 12/285,090 · Granted Feb 5, 2013

Anthracene-based compound and organic light emitting device employing the same

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Quick Facts
Patent No.
US 8,367,219
App. No.
12/285,090
Granted
Feb 5, 2013
Kind
B2
Abstract

Provided are an anthracene-based compound represented by Formula 1 or 2 and an organic light emitting device employing the same: where R is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group or a substituted or unsubstituted C2-C30 heteroaryl group, L is a bivalent linking group and a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group, and m is an integer of 0 to 3.

Claims (39)

1. An anthracene-based compound, represented by any one of Formulae 3 to 6 below:

wherein R 1 to R 17 are identical to or different from each other and are each independently one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group;

Ar 1 , Ar 2 and Ar 3 are identical to or different from each other, and Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group;

L is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group; and

m 1 is an integer of 2 to 3, and m 2 is an integer of 1 to 3.

2. The anthracene-based compound of claim 1 , wherein L is independently selected from the groups represented by formulae A-1 through A-21:

wherein R′ is identical to or different from each other within the formulas and across formulas and is one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group.

3. An anthracene-based compound of claim 1 , wherein Ar 1 , Ar 2 and Ar 3 are identical to or different from each other and are each independently represented by one of formulae B-1 through B-17:

wherein R′ is identical to or different from each other within the formulas and across formulas and is one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group.

4. An anthracene-based compound of claim 1 , wherein the compound is one of the compounds represented by Formulae 39-42 and 45-50 below:

5. An anthracene-based compound represented by one of Formulae 3 to 6:

wherein R 1 to R 17 are identical to or different from each other and 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 C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group;

Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of Formulae B-1 through B-17:

L is one of the groups represented by formulae A-1 through A-21:

wherein R′ is identical to or different from each other within the formulas and across formulas and is one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group; and

m 1 is an integer of 2 to 3, and m 2 is an integer of 1 to 3.

6. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, the organic layer comprising an anthracene-based compound of claim 5 .

7. An organic light emitting device comprising:

a first electrode;

a second electrode; and

at least one organic layer located between the first electrode and the second electrode, said at least one organic layer comprising an anthracene-based compound represented by any one of Formulae 3 to 6 below:

wherein R 1 to R 17 are identical to or different from each other and are each independently one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1 -C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group;

Ar 1 , Ar 2 and Ar 3 are identical to or different from each other, and Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group;

L is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group; and

m 1 is an integer of 2 to 3, and m 2 is an integer of 1 to 3.

8. The organic light emitting device of claim 7 , wherein the at least one layer comprising a compound represented by Formulae 3 to 6 is one selected from the group consisting of an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

9. The organic light emitting device of claim 7 , wherein said at least one organic layer further comprises at least one layer selected from the group consisting of an emitting layer, 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; located between the first electrode and the second electrode.

10. The organic light emitting device of claim 7 , wherein the layer comprising a compound represented by Formulae 3 to 6 further comprises an organic metal complex.

11. The organic light emitting device of claim 7 , wherein the layer comprising a compound represented by Formulae 3 to 6 further comprises an ionic salt.

12. The organic light emitting device of claim 7 , wherein L is one of the groups represented by the formulae below:

wherein R′ is identical to or different from each other within the formulas and across formula and is one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group.

13. The organic light emitting device of claim 7 , wherein Ar 1 , Ar 2 and Ar 3 are identical to or different from each other and are each independently represented by one of formulae B-1 through B-17:

wherein R′ is identical to or different from each other within the formulas and across formulas and is one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group.

14. The organic light emitting device of claim 7 , wherein the anthracene-based compound is one of the compounds represented by Formulae 39-42 and 45-50:

15. An anthracene-based compound represented by one of Formula 51 or Formula 52:

wherein R 1 to R 17 are identical to or different from each other and are each independently one selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted. C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group and a substituted or unsubstituted C2-C30 heteroaryl group;

Ar 1 , Ar 2 and Ar 3 are identical to or different from each other, and Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group;

L is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group.

16. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, the organic layer comprising an anthracene-based compound of claim 15 .

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 Aug 17, 2012
From: PARK, SANG-HOON; KWON, O-HYUN; YANG, SEUNG-GAK; KIM, YU-JIN; CHOI, YU-RI
To: SAMSUNG ELECTRONICS CO., LTD.,; SAMSUNG SDI CO., LTD.,
Reel/Frame 028806/0830 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2009
From: SAMSUNG SDI CO., LTD.
To: SAMSUNG MOBILE DISPLAY CO., LTD.
Reel/Frame 023620/0798 →