Dendritic molecule containing metal phthalocyanine, method of preparing the same and organic light emitting diode comprising the dendritic molecule
View Patent ↗A dendritic molecule represented by Formula 3: where Pc is metal phthalocyanine represented by Formula 2: where M is a core metal of the dendritic molecule; n is an integer in the range of 1 to 50; each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH 2 , CO, SO 2 and NHCO; and each of the Rs is independently selected from the group consisting of CN, COOH, SO 3 H and PO 3 H. The dendritic molecule containing metal phthalocyanine is dissolved in an organic solvent, and thus can be used to easily form a hole injection layer or a hole transport layer using solution deposition. The hole injection layer comprising the dendritic molecule containing metal phthalocyanine has good adhesion to an electrode and improved hole injection ability. The organic light emitting diode including the hole injection layer exhibits high luminance and emitting efficiency.
1. A dendritic molecule obtained from reacting a compound represented by Formula 3 and a metal or a metal compound, and optionally replacing CN group with R which is selected from the group consisting of COOH, SO 3 H and PO 3 H, the dendritic molecule including metal phthalocyanine represented by Formula 2:
where X is a bivalent linking group selected from the group consisting of CH 2 , SO 2 and NHCO;
where M is a core metal of the dendritic molecule.
2. The dendritic molecule of claim 1 , wherein the metal or the metal compound includes a metal element selected from the group consisting of Cu, Co, Ni, Ti, Fe, Ru and Zn.
3. A dendritic molecule represented by Formula 1:
where Pc is metal phthalocyanine represented by Formula 2:
where M is a core metal of the dendritic molecule;
n is an integer in the range of 2 to 50;
each of the Xs is a bivalent linking group independently selected from the group consisting of CH 2 , CO, SO 2 and NHCO; and
each of the Rs is independently selected from the group consisting of CN, COOH, SO 3 H and PO 3 H.
4. The dendritic molecule of claim 3 , wherein the core metal M of the metal phthalocyanine of Formula 2 is selected from the group consisting of Cu, Co, Ni, Ti, Fe, Ru and Zn.
5. The dendritic molecule of claim 3 , wherein the core metal M is Cu, and all of the Rs are COOH.
6. The dendritic molecule of claim 1 , represented by one of the below Formulae:
7. A dendritic molecule represented by one of Formulae 5 and 6:
8. The dendritic molecule of claim 7 , represented by Formula 6:
9. The dendritic molecule of claim 1 , having a molecular weight of 1,000 to 100,000.
10. An organic light emitting diode, comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a layer comprised of a dendritic molecule represented by Formula 1:
where Pc is metal phthalocyanine represented by Formula 2:
where M is a core metal of the dendritic molecule;
n is an integer in the range of 1 to 50;
each of the Xs is a bivalent linking group independently selected from the group consisting of O, S, CH 2 , CO, SO 2 and NHCO; and
each of the Rs is independently selected from the group consisting of CN, COOH, SO 3 H and PO 3 H; and
wherein the layer comprised of the dendritic molecule represented by Formula 1 is a buffer layer, a hole injection layer or a hole transport layer.
11. The organic light emitting diode of claim 10 , wherein the metal or the metal compound includes a metal element selected from the group consisting of Cu, Co, Ni, Ti, Fe, Ru and Zn.
12. The organic light emitting diode of claim 10 , further comprising at least one layer selected from the group consisting of an emissive layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, disposed between the first electrode and the second electrode.
13. The organic light emitting diode of claim 10 , wherein the organic layer has a structure selected from the group consisting of a stacked structure of a hole injection layer and an emissive layer, a stacked structure of a hole injection layer, an emissive layer and an electron injection layer, a stacked structure of a hole injection layer, a hole transport layer and an emissive layer, a stacked structure of a hole injection layer, a hole transport layer, an emissive layer and an electron injection layer, a stacked structure of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer and an electron injection layer, and a stacked structure of a hole injection layer, a hole transport layer, an emissive layer, a hole blocking layer, an electron transport layer and an electron injection layer.
14. The organic light emitting diode of claim 10 , wherein the dendritic molecule is represented by one of Formulae 4A through 4H:
15. The organic light emitting diode of claim 10 , wherein the dendritic molecule is represented by one of Formulae 5 and 6:
16. The organic light emitting diode of claim 10 , wherein X is selected from the group consisting of S, CH 2 , CO, SO 2 and NHCO.
17. The organic light emitting diode of claim 10 , wherein X is selected from the group consisting of CH 2 , CO and SO 2 .
18. The dendritic molecule of claim 1 , wherein where X is selected from the group consisting of CH 2 and SO 2 .
19. A dendritic molecule represented by Formula 1:
where Pc is metal phthalocyanine represented by Formula 2:
where M is a core metal of the dendritic molecule;
n is an integer in the range of 1 to 50;
each of the Xs is a bivalent linking group independently selected from the group consisting of CH 2 , SO 2 and NHCO; and
each of the Rs is independently selected from the group consisting of CN, COOH, SO 3 H and PO 3 H.