Heterocyclic compound and organic light emitting device comprising the same
View Patent ↗Provided is a heterocyclic compound represented by Formula I: wherein Ar 1 is a linking group and a C6-C16 arylene or heteroarylene group; Ar 2 and Ar 3 are each independently a C6-C20 aryl group, a C4-C20 heteroaryl group or a C6-C20 fused polycyclic group; Ar 4 is a C6-C20 aryl group, a C6-C20 aryloxy group, a C4-C20 heteroaryl group or a C6-C20 fused polycyclic group; and Ar 1 and Ar 3 , or Ar 2 and Ar 3 may be connected to each other to form a ring. The heterocyclic compound has high electrical stability and excellent charge transporting capability, and thus can be efficiently used as a material for forming at least one of a hole injecting layer, a hole transporting layer and an emitting layer suitable for fluorescent and phosphorescent devices realizing all colors including red, green, blue and white.
1. A heterocyclic compound represented by Formula I:
wherein Ar 1 is a bivalent linking group and is a C6-C16 substituted or unsubstituted arylene or heteroarylene group;
Ar 2 and Ar 3 are each independently selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group;
Ar 4 is selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C6-C20 substituted or unsubstituted aryloxy group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group; and
optionally, Ar 1 and Ar 3 or Ar 2 and Ar 3 are connected to each other to form a ring.
2. The heterocyclic compound of claim 1 , wherein Ar 2 and Ar 3 are each independently selected from the group consisting of a phenyl group, a tolyl group, a fluorophenyl group, a biphenyl group, a (N,N′-diphenyl)aminophenyl group, a naphthyl group, a phenylcarbazolyl group and a dimethylfluorenyl group.
3. The heterocyclic compound of claim 1 , wherein Ar 4 is selected from the group consisting of a phenyl group, a tolyl group, a cyanophenyl group, a fluorophenyl group, a biphenyl group, a naphthyl group and a naphthylphenyl group.
4. The heterocyclic compound of claim 1 , wherein Ar 1 is a phenylene group or a biphenylene group.
5. The heterocyclic compound of claim 1 , wherein Ar 1 and Ar 3 or Ar 2 and Ar 3 are connected to each other to form a carbazolyl group.
6. The heterocyclic compound of claim 1 , wherein the compound represented by Formula I is selected from the group consisting of the compounds represented by the formulae below:
7. The heterocyclic compound of claim 1 , wherein the compound represented by Formula I is selected from the group consisting of the compounds represented by Formulae 1 through 183:
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, the organic layer comprising at least one layer comprised of the heterocyclic compound of claim 1 , said at least one layer being at least one selected from the group consisting of a hole injection layer, a hole transport layer and an emission layer.
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, the organic layer comprising a heterocyclic compound. represented by Formula I:
wherein Ar 1 is a bivalent linking group and is a C6-C16 substituted or unsubstituted arylene or heteroarylene group;
Ar 2 and Ar 3 are each independently selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group;
Ar 4 is selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C6-C20 substituted or unsubstituted aryloxy group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group; and
Ar 1 and Ar 3 or Ar 2 and Ar 3 are optionally connected to each other to form a ring.
10. The organic light emitting device of claim 9 , wherein the organic layer is a hole injection layer or a hole transport layer.
11. The organic light emitting device of claim 9 , wherein the organic layer is a single layer having hole injecting and transporting functions.
12. The organic light emitting device of claim 9 , wherein the organic layer is an emission layer.
13. The organic light emitting device of claim 9 , wherein the heterocyclic compound represented by Formula I is used as a fluorescent or phosphorescent host in an emission layer.
14. The organic light emitting device of claim 9 , wherein Ar 2 and Ar 3 are each independently selected from the group consisting of a phenyl group, a tolyl group, a fluorophenyl group, a biphenyl group, a (N,N′-diphenyl)aminophenyl group, a naphthyl group, a phenylcarbazolyl group and a dimethylfluorenyl group.
15. The organic light emitting device of claim 9 , wherein Ar 4 is selected from the group consisting of a phenyl group, a tolyl group, a cyanophenyl group, a fluorophenyl group, a biphenyl group, a naphthyl group and a naphthylphenyl group.
16. The organic light emitting device of claim 9 , wherein Ar 1 is a phenylene group or a biphenylene group.
17. The organic light emitting device of claim 9 , wherein Ar 1 and Ar 3 or Ar 2 and Ar 3 are connected to each other to form a carbazolyl group.
18. A method of preparing a heterocyclic compound represented by Formula I, comprising:
performing a cyclization reaction of the compound (b) represented by
to prepare a compound (c) represented by
and
reacting the compound (c) and
to prepare the heterocyclic compound represented by Formula I:
wherein L 1 and L 2 are leaving group;
Ar 1 is a bivalent linking group and is a C6-C16 substituted or unsubstituted arylene or heteroarylene group;
Ar 2 and Ar 3 are each independently selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group;
Ar 4 is selected from the group consisting of a C6-C20 substituted or unsubstituted aryl group, a C6-C20 substituted or unsubstituted aryloxy group, a C4-C20 substituted or unsubstituted heteroaryl group and a C6-C20 substituted or unsubstituted fused polycyclic group; and
Ar 1 and Ar 3 or Ar 2 and Ar 3 are optionally connected to each other to form a ring.
19. The method of claim 18 , wherein the compound (b) is prepared by reacting 5-dimethyl-1,4-phenylenediamine and
20. The method of claim 18 , wherein Ar 2 and Ar 3 are each independently selected from the group consisting of a phenyl group, a tolyl group, a fluorophenyl group, a biphenyl group, a (N,N′-diphenyl)aminophenyl group, a naphthyl group, a phenylcarbazolyl group and a dimethylfluorenyl group;
Ar 4 is selected from the group consisting of a phenyl group, a tolyl group, a cyanophenyl group, a fluorophenyl group, a biphenyl group, a naphthyl group and a naphthylphenyl group; and
Ar 1 is a phenylene group or a biphenylene group.