IP Library › Granted Patent US 7,990,053
Granted Patent B2
US 7,990,053 · App. 12/838,066 · Granted Aug 2, 2011

Cyclopentaphenanthrene-based compound and organic electroluminescent device using the same

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Quick Facts
Patent No.
US 7,990,053
App. No.
12/838,066
Granted
Aug 2, 2011
Kind
B2
Abstract

Provided are a cyclopentaphenanthrene-based compound and an organic EL device using the same. The 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, a light-emitting layer in an organic EL device, and as an organic dye or an electronic material such as a nonlinear optical material.

Claims (63)

1. An organic electroluminescent (EL) device comprising:

a first electrode;

a second electrode; and

at least one organic layer located between the first electrode and the second electrode, the organic layer comprising an organic compound represented by formula 1:

wherein Y and Q are the same or different and each is 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;

m is an integer of 0 to 5;

n is an integer of 0 to 5;

R 1 and R 2 , when linked together, form one of rings represented by Formulae 2 through 5:

wherein “R 9 ”s are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group; and

A is a single bond, —O—, —S—, —(CH 2 ) s —, where s is an integer of 1 to 5;

R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group;

Z 1 , Z 2 , Z 3 , and Z 4 are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C8-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

X is a single bond, —CH═CH—, —O—, —S—, —Se—, or —C(R′R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10; and

o is 0 or 1.

2. The organic EL device of claim 1 , wherein the organic layer is a light-emitting layer, a hole injection layer, or a hole transport layer.

3. The organic EL device of claim 1 , wherein the organic EL device further comprising at least one 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.

4. An organic electroluminescent (EL) device, comprising:

a first electrode;

a second electrode; and

an organic layer comprising an emissive layer between the first electrode and the second electrode, the organic layer comprising an organic compound represented by Formula 1:

wherein Y and Q are the same or different and each is 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;

m is an integer of 0 to 5;

n is an integer of 0 to 5;

R 1 and R 2 are the same or different and each is a hydrogen, a 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 unsubsututed C2-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, R 1 and R 2 may be linked together, and R 1 and R 2 , when linked together, 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 , R 4 , R 5 , R 6 , R 7 , and R 8 are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group;

Z 1 , Z 2 , Z 3 , and Z 4 are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C8-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

X is a single bond, —CH═CH—, —O—, —S—, —Se—, or —C(R′R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10; and

o is 0or 1.

5. The organic EL device of claim 4 , wherein the organic layer is the emissive layer.

6. The organic EL device of claim 4 , wherein the organic layer further comprises a hole injection layer located between the first electrode and the emissive layer, and at least one of the emissive layer and the hole injection layer comprises the organic compound represented by Formula 1.

7. The organic EL device of claim 6 , wherein the hole injection layer comprises the organic compound represented by Formula 1.

8. The organic EL device of claim 4 , wherein the organic layer further comprises a hole injection layer located between the first electrode and the emissive layer, and a hole transport layer located between the hole injection layer and the emissive layer, and at least one of the emissive layer, the hole injection layer and the hole transport layer comprises the organic compound represented by Formula 1.

9. The organic EL device of claim 8 , wherein the hole transport layer comprises the organic compound represented by Formula 1.

10. The organic EL device of claim 4 , wherein in Formula 1, R 1 and R 2 , when linked together, form one of rings represented by Formulae 2 through 5:

wherein “R 9 ”s are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group; and

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

11. The organic EL device of claim 4 , wherein the organic compound is one of the compounds represented by Formulae 6 through 8:

wherein Y and Q are the same or different and each is 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;

m is an integer of 0 to 5;

n is an integer of 0 to 5;

R 1 ′ and R 2 ′ are the same or different and each is a hydrogen, a 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 C2-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;

Z 1 , Z 2 , Z 3 , and Z 4 are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

X is a single bond, —CH═CH—, —O—, —S—, —Se—, or —C(R′, R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10;

o is 0 or 1; and

“R 10 ”s are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group.

12. The organic EL device of claim 4 , wherein the organic compound is one of the compounds represented by Formulae 9 through 46:

13. An organic electroluminescent (EL) device, comprising:

a first electrode;

a second electrode;

an emissive layer located between the first electrode and the second electrode;

a hole injection layer located between the first electrode and the emissive layer;

a hole transport layer located between the hole injection layer and the emissive layer, at least one of the emissive layer, the hole injection layer and the hole transport layer is an organic layer comprising an organic compound selected from the group consisting of compounds represented by Formulae 6 through 8:

wherein Y and Q are the same or different and each is 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;

m is an integer of 0 to 5;

n is an integer of 0 to 5;

R 1 ′ and R 2 ′ are the same or different and each is a hydrogen, a 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 C2-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;

Z 1 , Z 2 , Z 3 , and Z 4 are the same or different and each is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 allylaryl group, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C2-C30 heteroarylene group;

X is a single bond, —CH═CH—, —O—, —S—, —Se—, or —C(R′, R″)— where R′ and R″ are the same as R 3 , or —(CH 2 ) p — where p is an integer of 1 to 10;

o is 0 or 1; and

“R 10 ”s are the same or different and each is a hydrogen, a 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 C2-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(G 1 )(G 2 ), or —Si(G 3 )(G 4 )(G 5 ) where G 1 , G 2 , G 3 , G 4 , and G 5 are each independently a 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 C2-C30 heterocycloalkyl group.

14. The organic El device of claim 13 , wherein the organic layer is the emissive layer.

15. The organic EL device of claim 13 , wherein the organic layer is the hole injection layer.

16. The organic EL device of claim 13 , wherein the organic layer is the hole transport layer.

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