Triarylamine-based compound, method of preparing the same, and organic light emitting device using the triarylamine-based compound
View Patent ↗A triarylamine-based compound of formula 1, a method of preparing the same, and an organic light emitting device including the triarylamine-based compound of formula 1: where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; R is a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group; n is an integer of 1 through 3; and m is an integer of 1 through 3. The triarylamine-based compound of formula 1 has excellent electrical properties and a great charge transporting capability. An organic light emitting device including an organic layer formed of the triarylamine-based compound has high efficiency, low operating voltage, great luminance, and long lifetime.
1. 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 triarylamine-based compound represented by one of formulae 2-4:
where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and
each R is independently a C1-C30 alkyl group.
2. The organic light emitting device of claim 1 , wherein the organic layer is at least one selected from the group consisting of a hole injection layer, a hole transport layer, and an emission layer.
3. The organic light emitting device of claim 1 , wherein the organic layer comprises a layer having hole injecting and hole transporting capabilities.
4. A method of preparing a triarylamine-based compound of one of formulae 2-4:
where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and
each R is independently a C1-C30 alkyl group,
the method comprising:
reacting compounds of formulae 8 through 10:
where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and
each R is independently a C1-C30 alkyl group.
5. The method of claim 4 , wherein the reaction is performed in the presence of tri(dibenzylideneacetone)dipalladium(0) at a reaction temperature of 50 to 150° C.
6. The method of claim 4 , wherein the compound of formula 8 is prepared by reacting a compound of formula 11 with butyl lithium and then by reacting the resultant product with copper chloride:
where R is a C1-C30 alkyl group.
7. The method of claim 6 , wherein the reaction temperature for the preparation of the compound of formula 8 is in the range of −78° C. to 0° C.
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 a triarylamine-based compound prepared by the method of claim 4 .
9. The organic light emitting device of claim 8 , wherein the reacting of the compounds of formulae 8 through 10 is performed in the presence of tri(dibenzylideneacetone)dipalladium(0) at a reaction temperature of 50° C. to 150° C.
10. The organic light emitting device of claim 8 , wherein the compound of formula 8 is prepared by reacting a compound of formula 11 with butyl lithium and then by reacting the resultant product with copper chloride:
where R is a C1-C30 alkyl group.
11. The organic light emitting device of claim 10 , wherein the reaction temperature for the preparation of the compound of formula 8 is in the range of −78° C. to 0° C.
12. The organic light emitting device of claim 1 , wherein the triarylamine-based compound is represented by formula 2:
where Ar 1 through Ar 4 are as described in claim 14 , and R is a C1-C10 alkyl group.
13. The organic light emitting device of claim 1 , wherein the triarylamine-based compound is represented by formula 3:
where each of Ar 1 through Ar 4 is as described in claim 14 , and R is a C1-C10 alkyl group.
14. The organic light emitting device of claim 1 , wherein the triarylamine-based compound is represented by formula 4:
where each of Ar 1 through Ar 4 is as described in claim 14 , and R is a C1-C10 alkyl group.
15. The organic light emitting device of claim 1 , wherein the triarylamine-based compound is selected from the group consisting of the compounds represented by formulae below: