IP Library › Granted Patent US 7,875,367
Granted Patent B2
US 7,875,367 · App. 11/826,781 · Granted Jan 25, 2011

Organoelectroluminescent compound and organoelectroluminescent device employing the same

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Quick Facts
Patent No.
US 7,875,367
App. No.
11/826,781
Granted
Jan 25, 2011
Kind
B2
Abstract

A cyclopentaphenanthrene-based compound is easy to prepare and excellent in solubility, color purity, and color stability. The cyclopentaphenanthrene-based compound is useful as a material for forming an organic layer, in particular, an emitting layer, in an organoelectroluminescent device, and as an organic dye or an electronic material such as a nonlinear optical material.

Claims (64)

1. A cyclopentaphenanthrene-based compound represented by Formula 1:

wherein each Q is independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group;

each Y is independently a substituted or unsubstituted C2-C30 alkylene group, a substituted or unsubstituted C6-C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same or different from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same or different from each other;

R 1 and R 2 are each independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group, and R 1 and R 2 can be optionally linked together to form a substituted or unsubstituted C3-C20 aliphatic ring, a substituted or unsubstituted C5-C30 heteroaliphatic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaromatic ring;

R 3 through R 16 are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group, with the proviso that, when X is hydrogen, and m and n are 0, at least one of R 9 through R 16 is not hydrogen; and

R 19 is hydrogen, halogen, a cyano group, a hydroxyl group, or a substituted or unsubstituted C1-C20 alkyl group.

2. The cyclopentaphenanthrene-based compound of claim 1 , wherein m is an integer of 1 to 3, and n is an integer of 1 to 3.

3. The cyclopentaphenanthrene-based compound of claim 1 , wherein the

in Formula 1 is represented by one of Formulae 2 through 5:

wherein each R 17 is independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group; and

A is a single bond, O, S, Se, or (CH 2 ) p where p is an integer of 1 to 5.

4. The cyclopentaphenanthrene-based compound of claim 1 , which is a compound selected from the group consisting of compounds represented by Formulae 6 through 8:

wherein each Q is independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group;

each Y is independently a substituted or unsubstituted C2˜C30 alkylene group, a substituted or unsubstituted C6˜C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same or different from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same or different from each other;

R 1 ′ and R 2 ′ are each independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

R 9 through R 16 are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group, with the proviso that, when X is hydrogen, and m and n are 0, at least one of R 9 through R 16 is not hydrogen; and

each R 18 is independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

5. The cyclopentaphenanthrene-based compound of claim 4 , wherein in Formulae 6 through 8, -[Q] m - is selected from the group consisting of chemical structures represented by Formulae 9A through 9R below:

wherein R′ and R″ are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

6. The cyclopentaphenanthrene-based compound of claim 4 , wherein in Formulae 6 through 8, —[Y] n —X is selected from the group consisting of chemical structures represented by Formulae 10A to 10R, 11A to 11S, 12A to 12Q, 13A to 13LL, 14A to 14R, and 15A to 15Z below:

wherein R′ and R″ are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

7. The cyclopentaphenanthrene-based compound of claim 4 , wherein m is an integer of 1 to 3, and n is an integer of 1 to 3.

8. The cyclopentaphenanthrene-based compound claim 1 , which is selected from the group consisting of compounds represented by Formulae 16 through 72 below:

9. An organoelectroluminescent device comprising:

a first electrode;

a second electrode; and

at least one organic layer interposed between the first electrode and the second electrode, the organic layer comprising a cyclopentaphenanthrene-based compound represented by Formula 1:

wherein each Q is independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group;

each Y is independently a substituted or unsubstituted C2-C30 alkylene group, a substituted or unsubstituted C6-C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same or different from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same or different from each other;

R 1 and R 2 are each independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group, and R 1 and R 2 can be optionally linked together to form a substituted or unsubstituted C3-C20 aliphatic ring, a substituted or unsubstituted C5-C30 heteroaliphatic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C2-C30 heteroaromatic ring;

R 3 through R 16 are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group, with the proviso that, when X is hydrogen, and m and n are 0, at least one of R 9 through R 16 is not hydrogen; and

R 19 is hydrogen, halogen, a cyano group, a hydroxyl group, or a substituted or unsubstituted C1-C20 alkyl group.

10. The organoelectroluminescent device of claim 9 , wherein the organic layer is an emitting layer, a hole injection layer, or a hole transport layer.

11. The organoelectroluminescent device of claim 9 , wherein the

in Formula 1 is represented by one of Formulae 2 through 5:

wherein each R 17 is independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group; and

A is a single bond, O, S, Se, or (CH 2 ) p where p is an integer of 1 to 5.

12. The organoelectroluminescent device of claim 9 , wherein the cyclopentaphenanthrene-based compound is selected from the group consisting of compounds represented by Formulae 6 through 8:

wherein each Q is independently a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group;

each Y is independently a substituted or unsubstituted C2˜C30 alkylene group, a substituted or unsubstituted C6˜C30 cycloalkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a substituted or unsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same or different from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same or different from each other;

R 1 ′ and R 2 ′ are each independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group;

R 9 through R 16 are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group; and

each R 18 is independently hydrogen, halogen, 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, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

13. The cyclopentaphenanthrene-based compound of claim 12 , wherein in Formulae 6 through 8, -[Q] m - is selected from the group consisting of chemical structures represented by Formulae 9A through 9R, and —[Y] n —X is selected from the group consisting of chemical structures represented by Formulae 10A to 10R, 11A to 11S, 12A to 12Q, 13A to 13LL, 14A to 14R, and 15A to 15Z below:

wherein R′ and R″ are each independently hydrogen, halogen, 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 arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group, —N(Z 1 )(Z 2 ) or —Si(Z 3 )(Z 4 )(Z 5 ) where Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

14. The organoelectroluminescent device of claim 9 , wherein the cyclopentaphenanthrene-based compound is selected from the group consisting of compounds represented by Formulae 16 through 72 below:

15. The organoelectroluminescent device of claim 9 , wherein said at least one organic layer comprises an emitting layer comprised of the cyclopentaphenanthrene-based compound.

16. The organoelectroluminescent device of claim 15 , wherein the emitting layer further comprises a fluorescent host material.

17. The organoelectroluminescent device of claim 15 , wherein the emitting layer further comprises a dopant material.

18. The organoelectroluminescent device of claim 15 , wherein the cyclopentaphenanthrene-based compound is used as a phosphorescent host material.

19. The organoelectroluminescent device of claim 18 , wherein the emitting layer further comprises at least one of 4,4′-N,N′-dicarbazole-biphenyl (CBP) and poly(n-vinylcarbazole) (PVK).

20. The organoelectroluminescent device of claim 15 , wherein the emitting layer comprises a host material represented by Formula 73 and a dopant of the cyclopentaphenanthrene-based compound:

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 Sep 25, 2007
From: PARK, SANG-HOON; KIM, YU-JIN; SON, JHUN-MO; CHOI, BYOUNG-KI; KWON, O-HYUN; KIM, MYEONG-SUK
To: SAMSUNG SDI CO., LTD.
Reel/Frame 019907/0471 →