Cyclopentaphenanthrene-based compound and organic electroluminescent device using the same
View Patent ↗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.
1. 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 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; and
R 1 and R 2 together or independently form a substituted or unsubstituted non-heterocyclic ring, and Z 1 , Z 2 , Z 3 , and Z 4 are substituted or unsubstituted non-heterocyclic rings,
wherein at least one of m and n is not 0.
2. The organic compound of claim 1 , wherein in Formula 1, R 1 and R 2 are linked together to form one of the 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, or —(CH 2 ) s —, where s is an integer of 1 to 5.
3. The organic compound of claim 1 , which is selected from the group consisting of compounds represented by Formulae 6 through 8 below:
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 ′ together or independently form a substituted or unsubstituted non-heterocyclic ring, and Z 1 , Z 2 , Z 3 , and Z 4 are independently substituted or unsubstituted non-heterocyclic rings; 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,
wherein at least one of m and n is not 0.
4. The organic compound of claim 1 , which is one of compounds represented by Formulae 14, 18-21, 37 and 39: