Fluorene-based compound and organo-electroluminescent device using the same
View Patent ↗Provided herein are fluorene-based compounds including a fluorene or a spirofluorene structure at both terminals and a spacer including one or more atoms between the both terminals. The invention further provides an organo-electroluminescent device having an organic layer in which the fluorene-based compound is introduced. The fluorene-based compound can be readily manufactured using dry and wet processes, and the organo-electroluminescent device using the same has excellent properties in color purity, internal and external efficiency, and thermal, optical and electric stability.
1. A fluorene-based compound represented by Formula 1 below:
where L is selected from the group consisting of a substituted or unsubstituted C 2 ˜C 30 alkylene group, a substituted or unsubstituted C 6 ˜C 30 cycloalkylene group, a substituted or unsubstituted C 6 ˜C 30 arylene group, a substituted or unsubstituted C 2 ˜C 30 heteroarylene group, and a substituted or unsubstituted C 2 ˜C 30 alkenylene group;
k is an integer from 0 to 2,
j is an integer from 0 to 2,
X is
where R 3 and R 4 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 ˜C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group;
m is an integer from 1 to 3,
R 5 and R 6 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group;
r 1 , r 2 , r 3 , r 4 , r 5 and r 6 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 ˜C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group.
2. A fluorene-based compound represented by Formula 2 below:
where L is selected from the group consisting of a substituted or unsubstituted C 2 ˜C 30 alkylene group, a substituted or unsubstituted C 6 ˜C 30 cycloalkylene group, a substituted or unsubstituted C 6 ˜C 30 arylene group, a substituted or unsubstituted C 2 ˜C 30 heteroarylene group, and a substituted or unsubstituted C 2 ˜C 30 alkenylene group;
k is an integer from 0 to 2,
j is an integer from 0 to 2,
X is
where R 3 and R 4 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 ˜C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group;
m is an integer from 1 to 3,
R 5 and R 6 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 ˜C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group;
r 1 , r 2 , r 3 , r 4 , r 5 and r 6 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 C 1 ˜C 20 alkyl group, a substituted or unsubstituted C 3 ˜C 20 cycloalkyl group, a substituted or unsubstituted C 5 ˜C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 ˜C 20 alkoxy group, a substituted or unsubstituted C 6 ˜C 30 aryl group, a substituted or unsubstituted C 6 ˜C 30 aralkyl group, and a substituted or unsubstituted C 2 ˜C 30 heteroaryl group.
3. The fluorene-based compound of claim 1 , wherein the alkyl group, the alkoxy group, the aryl group, the aralkyl group, the heteroaryl group, the cycloalkyl group, and the heterocycloalkyl group in the Formulae 1 and 2 can be substituted and the substituent is at least one selected from the group consisting of —F, —Cl, —Br, —CN, —NO 2 , and —OH; a C 1 ˜C 20 alkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 1 ˜C 20 alkoxy group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 6 ˜C 30 aryl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 2 ˜C 30 heteroaryl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 5 ˜C 20 cycloalkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, and a C 5 ˜C 30 heterocycloalkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH.
4. The fluorene-based compound of claim 2 , wherein the alkyl group, the alkoxy group, the aryl group, the aralkyl group, the heteroaryl group, the cycloalkyl group, and the heterocycloalkyl group in the Formulae 1 and 2 can be substituted and the substituent is at least one selected from the group consisting of —F, —Cl, —Br, —CN, —NO 2 , and —OH; a C 1 ˜C 20 alkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 1 ˜C 20 alkoxy group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 6 ˜C 30 aryl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 2 ˜C 30 heteroaryl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, a C 5 ˜C 20 cycloalkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH, and a C 5 ˜C 30 heterocycloalkyl group unsubstituted or substituted by —F, —Cl, —Br, —CN, —NO 2 or —OH.
5. The fluorene-based compound of claim 1 , wherein the compound of Formula 1 is selected from the group consisting of compounds represented by any one of the Formulas below:
6. The fluorene-based compound of claim 2 , wherein the compound of Formula 2 is selected from the group consisting of compounds of either of the Formulas below:
7. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 1 .
8. The organo-electroluminescent device of claim 7 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
9. The organo-electroluminescent device of claim 7 , further comprising at least one layer 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.
10. The organo-electroluminescent device of claim 8 , further comprising at least one layer 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.
11. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 2 .
12. The organo-electroluminescent device of claim 11 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
13. The organo-electroluminescent device of claim 11 , further comprising at least one layer 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.
14. The organo-electroluminescent device of claim 12 , further comprising at least one layer 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.
15. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 3 .
16. The organo-electroluminescent device of claim 15 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
17. The organo-electroluminescent device of claim 15 , further comprising at least one layer 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.
18. The organo-electroluminescent device of claim 16 , further comprising at least one layer 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.
19. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 4 .
20. The organo-electroluminescent device of claim 19 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
21. The organo-electroluminescent device of claim 19 , further comprising at least one layer 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.
22. The organo-electroluminescent device of claim 20 , further comprising at least one layer 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.
23. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 5 .
24. The organo-electroluminescent device of claim 23 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
25. The organo-electroluminescent device of claim 23 , further comprising at least one layer 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.
26. The organo-electroluminescent device of claim 24 , further comprising at least one layer 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.
27. An organo-electroluminescent device comprising:
a first electrode;
a second electrode; and
at least one organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises the fluorene-based compound of claim 6 .
28. The organo-electroluminescent device of claim 27 , wherein the organic layer is an emitting layer, a hole injection layer or a hole transport layer.
29. The organo-electroluminescent device of claim 27 , further comprising at least one layer 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.
30. The organo-electroluminescent device of claim 28 , further comprising at least one layer 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.
31. A method of making an organo-electroluminescent device comprising depositing:
an organic layer comprising the fluorene-based compound of claim 1 between a first electrode and a second electrode.
32. A method of making an organo-electroluminescent device comprising depositing:
an organic layer comprising the fluorene-based compound of claim 2 between a first electrode and a second electrode.