Cyclopentaphenanthrene-based compound and organoelectroluminescent device employing the same
View Patent ↗The present invention is related to a cyclopentaphenanthrene-based compound and an organic electroluminescence device using the same. In particular, the cyclopentaphenanthrene-based compound offers several advantages, including easy processibility, high solubility, superior color purity, color stability and thermal stability. Moreover, the cyclopentaphenanthrene-based compound may be used not only as a material for forming an organic layer of an organic electroluminescence device, particularly, a light-emitting layer, but also as a material of an organic pigment or nonlinear optical substance.
1. A cyclopentaphenanthrene-based compound represented by Formula 1,
wherein X is C, N, O, or S, where when X is C, a and b are both 1, when X is N, one of a and b is 0, and when X is O or S, a and b are both 0;
wherein R 1 and R 2 are each selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, a substituted or unsubstituted C 6 -C 30 heteroaryloxy, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, or wherein R 1 and R 2 are interconnected to form a saturated or unsaturated C 3 -C 30 ring; R 3 , R 3 ′, R 4 , R 4 ′, R 5 and R 5 ′ are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 arylalkyl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group;
wherein R 1 and R 2 are not both hydrogen; and
wherein m is an integer in the range of 2 to about 5,000.
2. A cyclopentaphenanthrene-based compound represented by Formula 2, wherein the compound comprises an arylene repeating unit (Ar),
wherein X is C, N, O or S, where when X is C, a and b are both 1, when X is N, one of a and b is 0, and when X is O or S, a and b are both 0;
wherein R 1 and R 2 are each selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, a substituted or unsubstituted C 6 -C 30 heteroaryloxy, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, or wherein R 1 and R 2 are interconnected to form a saturated or unsaturated C 3 -C 30 ring: R 3 , R 3 ′, R 4 , R 4 ′, R 5 and R 5 ′ are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 arylalkyl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group;
wherein R 1 and R 2 are not both hydrogen;
wherein m is an integer in the range of 2 to about 5,000;
wherein Ar is a substituted or unsubstituted C 6 -C 30 arylene, or a substituted or unsubstituted C 2 -C 30 heteroarylene group; and
wherein n is a real number in the range of about 0.01 to about 1.
3. The cyclopentaphenanthrene-based compound of claim 2 , wherein the Ar unit has a structure selected from the group consisting of structures represented by Formula 3:
wherein Y is O or S; and
wherein R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of a hydrogen, a hydroxyl, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group.
4. The cyclopentaphenanthrene-based compound of claim 2 represented by Formula 4,
wherein R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group.
5. The cyclopentaphenanthrene-based compound of claim 1 represented by Formula 5,
wherein R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group.
6. The cyclopentaphenanthrene-based compound of claim 1 represented by Formula 6,
wherein R 1 and R 2 are each independently a substituted or unsubstituted C 1 -C 12 alkyl group.
7. The cyclopentaphenanthrene-based compound of claim 6 represented by Formula 7,
8. The cyclopentaphenanthrene-based compound of claim 2 represented by Formula 8,
wherein R 1 , R 2 and R 6 are each independently a substituted or unsubstituted C 1 -C 12 alkyl group; and
wherein n is a real number in the range of about 0.01 to about 0.99.
9. The cyclopentaphenanthrene-based compound of claim 8 represented by Formula 9,
Formula 9
10. An organic electroluminescent device, comprising: an organic layer between a pair of electrodes, wherein the organic layer comprises a cyclopentaphenanthrene-based compound of:
wherein X is C, N, O or S, where when X is C, a and b are both 1, when X is N, one of a and b is 0, and when X is O or S, a and b are both 0;
wherein R 1 and R 2 are each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, a substituted or unsubstituted C 6 -C 30 heteroaryloxy, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, or R 1 and R 2 are interconnected to form a saturated or unsaturated C 3 -C 30 ring; where R 3 , R 3 ′, R 4 , R 4 ′, R 5 and R 5 ′ are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 arylalkyl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group; and
wherein m is an integer in the range of 2 to about 5,000.
11. The organic electroluminescence device of claim 10 , wherein the organic layer is a light-emitting layer or a hole transport layer.
12. An organic electroluminescent device, comprising:
an organic layer between a pair of electrodes, wherein the organic layer comprises a cyclopentaphenanthrene-based compound of:
wherein X is C, N, O or S, where when X is C, a and b are both 1, when X is N, one of a and b is 0, and when X is O or S, a and b are both 0;
wherein R 1 and R 2 are each independently selected from the group consisting of a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, a substituted or unsubstituted C 6 -C 30 heteroaryloxy and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, or R 1 and R 2 are interconnected to form a saturated or unsaturated C 3 -C 30 ring; where R 3 , R 3 ′, R 4 , R 4 ′, R 5 and R 5 ′ are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 arylalkyl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group;
wherein m is an integer in the range of 2 to about 5,000;
wherein Ar is a substituted or unsubstituted C 6 -C 30 arylene, or a substituted or unsubstituted C 2 -C 30 heteroarylene group; and
wherein n is a real number in the range of about 0.01 to about 1.
13. The organic electroluminescence device of claim 12 , wherein the Ar unit has a structure selected from the group consisting of:
wherein Y is O or S; and
wherein R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of a hydrogen, a hydroxyl, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, and a substituted or unsubstituted C 2 -C 30 heteroaryl group.
14. The organic electroluminescence device of claim 12 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 4,
wherein R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group.
15. The organic electroluminescence device of claim 10 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 5,
wherein R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of a hydrogen, a hydroxy, a substituted or unsubstituted amino, a cyano, a halogen atom, a substituted or unsubstituted C 1 -C 30 alkyl, a substituted or unsubstituted C 3 -C 30 cycloalkyl, a substituted or unsubstituted C 1 -C 30 alkoxy, a substituted or unsubstituted C 6 -C 30 aryl, a substituted or unsubstituted C 6 -C 30 aryloxy, a substituted or unsubstituted C 6 -C 30 arylalkyl, a substituted or unsubstituted C 2 -C 30 heteroaryl, and a substituted or unsubstituted C 2 -C 30 heteroaryloxy group.
16. The organic electroluminescence device of claim 10 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 6,
wherein R 1 and R 2 are each independently a substituted or unsubstituted C 1 -C 12 alkyl group.
17. The organic electroluminescence device of claim 16 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 7,
18. The organic electroluminescence device of claim 12 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 8,
wherein R 1 , R 2 and R 6 are each independently a substituted or unsubstituted C 1 -C 12 alkyl group; and
wherein n is a real number in the range of about 0.01 to about 0.99.
19. The organic electroluminescence device of claim 18 , wherein the cyclopentaphenanthrene-based compound is represented by Formula 9,
where n is a real number in the range of about 0.01 to about 0.99; and m is an integer in the range of 2 to about 5,000.