Difluoropyridine-based compound and organic electroluminescent device using the same
View Patent ↗A difluoropyridine-based compound includes at least one difluoropyridine group in its molecule. The difluoropyridine-based compound may be used as an electron injection material, an electron transport material, or a hole blocking material in full-color fluorescent or phosphorescent devices. The difluoropyridine-based compound has good electrical characteristics and a high charge transport capability. The difluoropyridine-based compound may be used to produce an organic electroluminescent device with high efficiency, low voltage, improved brightness, and a long life expectancy.
1. A difluoropyridine-based compound represented by Formula 1 below:
wherein Ar and Ar 1 are each selected from the group of a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
R 1 and R 2 are connected to form a ring or are each selected from the group of a hydrogen atom, halogen, a cyano group, a formyl group, a substituted alkyl group of 1-30 carbon atoms, an unsubstituted alkyl group of 1-30 carbon atoms, a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
n1 is an integer from 0 to 3; and
n2 is an integer from 2 to 6.
2. The difluoropyridine-based compound of claim 1 ,
wherein Ar and Ar 1 are each selected from the group of a phenyl group, a methylphenyl group, a trimethylphenyl group, an ethylphenyl group, an ethylbiphenyl group, an o-fluorophenyl group, an m-fluorophenyl group, a p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, an o-cumenyl group, an m-cumenyl group and a p-cumenyl group, a mesityl group, a phenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a methylnaphthyl group, an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthylenyl group, a fluorenyl group, an anthraquinolyl group, a methylanthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an ovalenyl group, a carbazolyl group, a lower alkyl carbazolyl group, a biphenyl group, a lower alkyl biphenyl group, a lower alkoxy biphenyl group, a thiophenyl group, an indolyl group, and a pyridyl group.
3. The difluoropyridine-based compound of claim 1 ,
wherein Ar and Ar 1 are each selected from the group of pyrazole, imidazole, oxazole, thiazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, oxadiazole, pyridine, pyridazine, pyrimidine, triazine, and derivatives thereof.
4. The difluoropyridine-based compound of claim 1 ,
wherein R 1 and R 2 are each selected from the group of hydrogen, a substituted alkyl group of 1-15 carbon atoms and an unsubstituted alkyl group of 1-15 carbon atoms.
5. The difluoropyridine-based compound of claim 1 ,
wherein Ar, R 1 , R 2 , and n2 are selected to form the difluoropyridine-based compounds represented by Formulae 2 through 6 below:
wherein Ar 1 is selected from the group of a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms; and
n1 is an integer from 0 to 3.
6. The difluoropyridine-based compound of claim 5 ,
wherein Ar 1 is selected from the group of:
7. The difluoropyridine-based compound of claim 1 ,
wherein Ar, R 1 , R 2 , and n2 are selected to form the difluoropyridine-based compounds represented by Formulae 7-13 below:
wherein Ar 1 is selected from the group of a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms; and
n1 is an integer from 0 to 3.
8. The difluoropyridine-based compound of claim 7 ,
wherein Ar 1 is selected from the group of:
9. The difluoropyridine-based compound of claim 1 ,
wherein Ar, Ar 1 , R 1 , R 2 , n1 and n2 are selected to form the difluoropyridine-based compounds represented by Formulae 14 through 29 below:
10. A method of preparing a difluoropyridine-based compound represented by Formula 1 below, comprising:
reacting a compound represented by Formula 1A below with a compound represented by Formula 1B or Formula 1C below:
wherein Ar and Ar 1 are each selected from the group of a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
X is a halogen compound;
R 1 and R 2 are connected to form a ring or are each selected from the group of a hydrogen atom, halogen, a cyano group, a formyl group, a substituted alkyl group of 1-30 carbon atoms, an unsubstituted alkyl group of 1-30 carbon atoms, a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
n1 is an integer from 0 to 3; and
n2 is an integer from 2 to 6.
11. The method of claim 10 ,
wherein Ar and Ar 1 are each selected from the group of pyrazole, imidazole, oxazole, thiazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, oxadiazole, pyridine, pyridazine, pyrimidine, triazine, and derivatives thereof;
X is Br or Cl;
R 1 and R 2 are each selected from the group of hydrogen, a substituted alkyl group of 1-15 carbon atoms, and an unsubstituted alkyl group of 1-15 carbon atoms;
n1 is an integer from 0 to 2; and
n2 is an integer from 3 to 4.
12. An organic electroluminescent (EL) device, comprising:
an organic layer positioned between a pair of electrodes,
wherein the organic layer comprises a difluoropyridine-based compound represented by Formula 1:
wherein Ar and Ar 1 are each selected from the group of a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
R 1 and R 2 are connected to form a ring or are each selected from the group of a hydrogen atom, halogen, a cyano group, a formyl group, a substituted alkyl group of 1-30 carbon atoms, an unsubstituted alkyl group of 1-30 carbon atoms, a substituted aryl group of 6-30 carbon atoms, an unsubstituted aryl group of 6-30 carbon atoms, a substituted heterocyclic compound of 4-30 carbon atoms, and an unsubstituted heterocyclic compound of 4-30 carbon atoms;
n1 is an integer from 0 to 3; and
n2 is an integer from 2 to 6.
13. The organic EL device of claim 12 ,
wherein the organic layer is an electron injection layer.
14. The organic EL device of claim 12 ,
wherein the organic layer is an electron transport layer, a hole blocking layer, or an electron transport/hole blocking layer.
15. The organic EL device of claim 12 ,
wherein the organic EL device has a structure selected from the group of first electrode/hole transport layer/light-emitting layer/electron transport layer/second electrode, first electrode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/second electrode, and first electrode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/second electrode.