Dendrimer and organic light-emitting device using the same
View Patent ↗A dendrimer and an organic light-emitting device including an organic layer having the dendrimer.
1. A dendrimer compound comprising a core unit, a bridge unit, and a dendron unit,
wherein the core unit comprises a functional group selected from the group consisting of functional groups represented by Formulas 11 to 15 below:
where *** is a binding site with the bridge unit
wherein the bridge unit comprises a divalent or trivalent functional group selected from the group consisting of a substituted or unsubstituted C 6 -C 50 aromatic hydrocarbon and a substituted or unsubstituted C 3 -C 50 hetero aromatic hydrocarbon, and
wherein the dendron unit comprises a monovalent fluorene-based functional group represented by Formula 1 below:
where Z is selected from the group consisting of
Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 50 aryl group and a substituted or unsubstituted C 3 -C 50 heteroaryl group,
X 1 and X 2 are each independently selected from the group consisting of nitrogen (N), boron (B), and phosphorus (P),
Y 1 , Y 2 , Y 3 , and Y 4 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 1 -C 50 alkylene group, a substituted or unsubstituted C 2 -C 50 alkenylene group, a substituted or unsubstituted C 2 -C 50 alkynylene group, a substituted or unsubstituted C 3 -C 50 cycloalkylene group, a substituted or unsubstituted C 1 -C 50 alkoxylene group, a substituted or unsubstituted C 6 -C 50 arylene group, and a substituted or unsubstituted C 3 -C 50 heteroarylene group,
R 1 , R 2 , and R 3 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 2 -C 50 alkenyl group, a substituted or unsubstituted C 2 -C 50 alkynyl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 1 -C 50 alkoxy group, a substituted or unsubstituted C 6 -C 50 aryl group, and a substituted or unsubstituted C 3 -C 50 heteroaryl group,
R′ and R″ are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, and a substituted or unsubstituted C 3 -C 50 heteroaryl group, wherein at least two adjacent groups of R 1 , R 2 , R 3 , R′ and R″ are linked to form a saturated or unsaturated ring, and
* is a binding site between the bridge unit and one selected from the group consisting of Ar 1 , Z, and the fluorene group in Formula 1.
2. The dendrimer compound of claim 1 , wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a phenyl group, a halophenyl group, a cyanophenyl group, a phenoxyphenyl group, a C 1 -C 15 alkyl phenyl group, a di(C 1 -C 15 alkyl) phenyl group, a C 1 -C 15 alkoxy phenyl group, a di(C 1 -C 15 alkoxy) phenyl group, C 6 -C 15 aryl phenyl group, a di(C 6 -C 15 aryl) phenyl group, a naphthyl group, a halonaphthyl group, a cyanonaphthyl group, a phenoxynaphthyl group, a C 1 -C 15 alkyl naphthyl group, a di(C 1 -C 15 alkyl) naphthyl group, a C 1 -C 15 alkoxy naphthyl group, a di(C 1 -C 15 alkoxy) naphthyl group, a C 6 -C 15 aryl naphthyl group, a di(C 6 -C 15 aryl) naphthyl group, an anthryl group, a halo-anthryl group, a cyanoanthryl group, a phenoxyanthryl group, a C 1 -C 15 alkyl anthryl group, a di(C 1 -C 15 alkyl) anthryl group, a C 1 -C 15 alkoxy anthryl group, a di(C 1 -C 15 alkoxy) anthryl group, a C 6 -C 15 aryl anthryl group, a di(C 6 -C 15 aryl) anthryl group, a phenanthryl group, a halophenanthryl group, a cyanophenanthryl group, a phenoxyphenanthryl group, a C 1 -C 15 alkyl phenanthryl group, a di(C 1 -C 15 alkyl) phenanthryl group, a C 1 -C 15 alkoxy phenanthryl group, a di(C 1 -C 15 alkoxy) phenanthryl group, a C 6 -C 15 aryl phenanthryl group, a di(C 6 -C 15 aryl) phenanthryl group, a fluorenyl group, a halofluorenyl group, a cyanofluorenyl group, a phenoxyfluorenyl group, a C 1 -C 15 alkyl fluorenyl group, a di(C 1 -C 15 alkyl) fluorenyl group, a C 1 -C 15 alkoxy fluorenyl group, a di(C 1 -C 15 alkoxy) fluorenyl group, a C 6 -C 15 aryl fluorenyl group, a di(C 6 -C 15 aryl) fluorenyl group, a pyridyl group, a halopyridyl group, a cyanopyridyl group, a phenoxypyridyl group, a C 1 -C 15 alkyl pyridyl group, a di(C 1 -C 15 alkyl) pyridyl group, a C 1 -C 15 alkoxy pyridyl group, a di(C 1 -C 15 alkoxy) pyridyl group, a C 6 -C 15 aryl pyridyl group, a di(C 6 -C 15 aryl) pyridyl group, a pyrenyl group, a halopyrenyl group, a cyanopyrenyl group, a phenoxypyrenyl group, a C 1 -C 15 alkyl pyrenyl group, a di(C 1 -C 15 alkyl) pyrenyl group, a C 1 -C 15 alkoxy pyrenyl group, a di(C 1 -C 15 alkoxy) pyrenyl group, a C 6 -C 15 aryl pyrenyl group, a di(C 6 -C 15 aryl) pyrenyl group, a phenanthrolinyl group, a halophenanthrolinyl group, a cyanophenanthrolinyl group, a phenoxyphenanthrolinyl group, a C 1 -C 15 alkyl phenanthrolinyl group, a di(C 1 -C 15 alkyl) phenanthrolinyl group, a C 1 -C 15 alkoxy phenanthrolinyl group, a di(C 1 -C 15 alkoxy) phenanthrolinyl group, a C 6 -C 15 aryl phenanthrolinyl group, a di(C 6 -C 15 aryl) phenanthrolinyl group, a quinolinyl group, a haloquinolinyl group, a cyanoquinolinyl group, a phenoxyquinolinyl group, a C 1 -C 15 alkyl quinolinyl group, a di(C 1 -C 15 alkyl) quinolinyl group, a C 1 -C 15 alkoxy quinolinyl group, a di(C 1 -C 15 alkoxy) quinolinyl group, a C 6 -C 15 aryl quinolinyl group, a di(C 6 -C 15 aryl) quinolinyl group, a carbazolyl group, a halocarbazolyl group, a cyanocarbazolyl group, a phenoxycarbazolyl group, a C 1 -C 15 alkyl carbazolyl group, a di(C 1 -C 15 alkyl) carbazolyl group, a C 1 -C 15 alkoxy carbazolyl group, a di(C 1 -C 15 alkoxy) carbazolyl group, a C 6 -C 15 aryl carbazolyl group, and a di(C 6 -C 15 aryl) carbazolyl group.
3. The dendrimer compound of claim 1 , wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a phenyl group, a halophenyl group, a cyanophenyl group, a biphenyl group, a dimethylfluorenyl group, a carbazolyl group, and a diphenylcarbazolyl group.
4. The dendrimer compound of claim 1 , wherein X 1 and X 2 are nitrogen (N).
5. The dendrimer compound of claim 1 , wherein Y 1 , Y 2 , Y 3 , and Y 4 are each independently selected from the group consisting of a single bond, a methylene group, an ethylene group, a propylene group, an isobutylene group, a sec-butylene group, a phenylene group, a methylphenylene group, an ethylphenylene group, an o-, m- and p-fluorophenylene group, a dichlorophenylene group, a cyanophenylene group, a dicyanophenylene group, a trifluoromethoxyphenylene group, a biphenylene group, a halobiphenylene group, a cyanobiphenylene group, a methylbiphenylene group, an ethylbiphenylene group, a methoxybiphenylene group, and an ethoxybiphenylene group.
6. The dendrimer compound of claim 1 , wherein Y 1 , Y 2 , Y 3 , and Y 4 are each independently selected from the group consisting of a single bond, a methylene group, an ethylene group, a propylene group, an isobutylene group, a sec-butylene group, a phenylene group, or a diphenylene group.
7. The dendrimer compound of claim 1 , wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a phenyl group, a methylphenyl group, an ethylphenyl group, an o-, m- and p-fluorophenyl group, a dichlorophenyl group, a cyanophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, a biphenyl group, a halobiphenyl group, a cyanobiphenyl group, a methylbiphenyl group, an ethylbiphenyl group, a methoxybiphenyl group, and an ethoxybiphenyl group.
8. The dendrimer compound of claim 1 , wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a phenyl group, or a biphenyl group.
9. The dendrimer compound of claim 1 , wherein the fluorene-based functional group is selected from the group consisting of functional groups represented by Formulae 2 to 6 below:
where, * is a binding site with the bridge unit.
10. The dendrimer compound of claim 1 , wherein the bridge unit comprises a functional group selected from the group consisting of functional groups represented by Formulas 7 to 10 below:
where ** is a binding site with an adjacent unit.
11. The dendrimer compound of claim 1 , wherein the average molecular weight of the dendrimer compound is from about 1,000 to 100,000.
12. The dendrimer compound of claim 1 , wherein the dendrimer further comprises a surface unit that is selected from the group consisting of a substituted or unsubstituted C 6 -C 50 aryl group and a substituted or unsubstituted C 3 -C 50 heteroaryl group at the end of the dendron unit.
13. The dendrimer compound of claim 1 , wherein the dendrimer is selected from the group consisting of compounds represented by Dendrimer 1 to 6:
14. An organic light-emitting device comprising a pair of electrodes and an organic layer interposed between the electrodes, wherein the organic layer comprises a dendrimer compound according to claim 1 .
15. The organic light-emitting device of claim 14 , wherein the organic layer comprises at least one selected from the group consisting of an emission layer, a hole injection layer, and a hole transport layer.
16. The organic light-emitting device of claim 14 , wherein the organic layer comprises an emission layer.
17. The organic light-emitting device of claim 14 , wherein the dendrimer is a host of a green or red dopant.
18. An organic light-emitting device comprising a pair of electrodes and an organic layer interposed between the electrodes, wherein the organic layer comprises a dendrimer compound according to claim 12 .
19. The organic light-emitting device of claim 18 , wherein the organic layer comprises at least one selected from the group consisting of an emission layer, a hole injection layer, and a hole transport layer.
20. A dendrimer compound comprising a core unit, a bridge unit, and a dendron unit,
wherein the core unit comprises a trivalent or tetravalent functional group selected from the group consisting of a substituted or unsubstituted C 1 -C 50 aliphatic hydrocarbon, a substituted or unsubstituted C 6 -C 50 aromatic hydrocarbon, and a substituted or unsubstituted C 3 -C 50 hetero aromatic hydrocarbon,
wherein the bridge unit comprises a functional group selected from the group consisting of functional groups represented by Formulas 7 to 10 below:
where ** is a binding site with an adjacent unit
and wherein the dendron unit comprises a monovalent fluorene-based functional group represented by Formula 1 below:
where Z is selected from the group consisting of
Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 50 aryl group and a substituted or unsubstituted C 3 -C 50 heteroaryl group,
X 1 and X 2 are each independently selected from the group consisting of nitrogen (N), boron (B), and phosphorus (P),
Y 1 , Y 2 , Y 3 , and Y 4 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 1 -C 50 alkylene group, a substituted or unsubstituted C 2 -C 50 alkenylene group, a substituted or unsubstituted C 2 -C 50 alkynylene group, a substituted or unsubstituted C 3 -C 50 cycloalkylene group, a substituted or unsubstituted C 1 -C 50 alkoxylene group, a substituted or unsubstituted C 6 -C 50 arylene group, and a substituted or unsubstituted C 3 -C 50 heteroarylene group,
R 1 , R 2 , and R 3 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 2 -C 50 alkenyl group, a substituted or unsubstituted C 2 -C 50 alkynyl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 1 -C 50 alkoxy group, a substituted or unsubstituted C 6 -C 50 aryl group, and a substituted or unsubstituted C 3 -C 50 heteroaryl group,
R′ and R″ are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, deuterium, tritium, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 50 aryl group, and a substituted or unsubstituted C 3 -C 50 heteroaryl group, wherein at least two adjacent groups of R 1 , R 2 , R 3 , R′ and R″ are linked to form a saturated or unsaturated ring, and
* is a binding site between the bridge unit and one selected from the group consisting of Ar 1 , Z, and the fluorene group in Formula 1.
21. An organic light-emitting device comprising a pair of electrodes and an organic layer interposed between the electrodes, wherein the organic layer comprises a dendrimer compound according to claim 20 .