Heterocyclic compound and an organic light emitting device comprising the same
A heterocyclic compound represented by Formula 1 below: X is selected from the group consisting of nitrogen, boron, and phosphorous; and Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently selected from the group consisting of a C6-C30 substituted or unsubstituted aryl group, a C6-C30 substituted or unsubstituted aryloxy group, a C4-C20 substituted or unsubstituted heterocyclic group, and a C6-C20 fused polycyclic group. The heterocyclic compound can be included in emission layers of top emission and bottom emission organic light emitting devices.
1. A heterocyclic compound represented by Formula 1:
wherein X is selected from the group consisting of nitrogen, boron, and phosphorous; and
the Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each independently selected from the group consisting of a C6-C30 substituted or unsubstituted aryl group, a C6-C30 substituted or unsubstituted aryloxy group, a C4-C20 substituted or unsubstituted heterocyclic group, and a C6-C20 fused polycyclic group.
2. The heterocyclic compound of claim 1 , wherein:
the Ar 1 , Ar 2 , Ar 3 , and Ar 4 are each independently selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a carbazolyl group, a pyridyl group, a quinolyl group, and derivatives thereof, in which at least one of the hydrogen atoms is substituted with a C1-C5 short-chain alkyl group, a C1-C5 short-chain alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, or a halogen group.
3. The heterocyclic compound of claim 1 , wherein the Ar 1 and Ar 3 are identical, and the Ar 2 and Ar 4 are identical.
4. The heterocyclic compound of claim 1 , wherein X is nitrogen.
5. The heterocyclic compound of claim 1 , wherein the compound represented by Formula 1 is selected from the group consisting of the compounds represented by the formulae below:
6. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises a heterocyclic compound according to claim 1 .
7. The organic light emitting device of claim 6 , wherein the organic layer is a blue light emission layer.
8. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises a heterocyclic compound according to claim 2 .
9. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises a heterocyclic compound according to claim 3 .
10. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises a heterocyclic compound according to claim 4 .
11. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode,
wherein the organic layer comprises a heterocyclic compound according to claim 5 .
12. A method of preparing a heterocyclic compound represented by the following Formula 3, comprising subjecting a compound represented by the following Formula 4 to a cyclization reaction:
wherein the Ar 1 and Ar 2 are each independently selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a carbazolyl group, a pyridyl group, and a quinolyl group, and derivatives thereof, in which at least one of the hydrogen atoms is substituted with a C1-C5 short-chain alkyl group, a C1-C5 short-chain alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, or a halogen group.
13. The method of claim 12 , wherein the compound represented by Formula 4 is prepared by subjecting 2,5-dimethyl-1,4-phenylenediamine (a) to i) N-arylaton and ii) N-acylation:
wherein,
the Ar 1 and Ar 2 are each independently selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a carbazolyl group, a pyridyl group, and a quinolyl group, and derivatives thereof, in which at least one of the hydrogen atoms is substituted with a C1-C5 short-chain alkyl group, a C1-C5 short-chain alkoxy group, a cyano group, an amine group, a phenoxy group, a phenyl group, or a halogen group,
the L 1 is a leaving group selected from a bromo group, or an iodo group, and
the L 2 is a leaving group selected from a chloro group, a bromo group or an anhydride group.