Organic electroluminescence device comprising an azine compound and a rare earth metal, rare earth metal compound, and/or rare earth metal complex and an electronic equipment comprising said organic electroluminescence device
An organic electroluminescence device comprising an electron-transporting zone comprising i) at least one compound represented by formula (I), and ii) at least one rare earth metal, rare earth metal compound, and/or rare earth metal complex, wherein the electron-transporting zone does not comprise an alkali metal, an alkali metal compound, an alkali metal complex, an alkaline earth metal, an alkaline earth metal compound, and an alkaline earth metal complex; a material for an organic electroluminescence device comprising a combination of at least one compound of formula (I) and at least one rare earth metal, rare earth metal compound, and/or rare earth metal complex; an organic electroluminescence device comprising said organic electroluminescence device and the use of a compound of formula (I) in combination with at least one rare earth metal, rare earth metal compound, and/or rare earth metal complex, in an electron-transporting zone of an organic electroluminescence device, wherein the electron-transporting zone does not comprise an alkali metal, an alkali metal compound, an alkali metal complex, an alkaline earth metal, an alkaline earth metal compound, and an alkaline earth metal complex.
1 . An organic electroluminescence device, comprising:
a cathode;
an anode;
an organic thin film layer region comprising an emitting layer disposed between the cathode and the anode; and
an electron-transporting zone between the emitting layer and the cathode,
wherein electron-transporting zone comprises (a) an electron-transporting layer and (b) a hole-blocking layer and/or an electron-injecting layer,
wherein the electron-transporting zone does not comprise any of an alkali metal, an alkali metal compound, an alkali metal complex, an alkaline earth metal, an alkaline earth metal compound, and an alkaline earth metal complex,
wherein the electron-transporting zone comprises:
(i) Yb, a Yb compound, and/or a Yb complex, formed as a rare earth metal layer in an interfacial region of the electron transporting zone; and
(ii) a compound of formula (I) in the electron-transporting zone as (ii-a) an electron transport material in the electron-transporting layer contacting the rare earth metal layer or (ii-b) as an electron injection material in the electron-injecting layer contacting the rare earth metal layer:
wherein
Az is 3-pyridyl,
R 1 and R 2 are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO,
X 1 , X 2 , and X 3 are each independently N or CR 3 , at least two of X 1 , X 2 , and X 3 being N,
R a and R b are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms,
R 3 is hydrogen, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO, and
-(L 1 ) m -(L 2 ) n - is one of the following structures, the dotted lines being bonding sites:
2 . The organic electroluminescence device of claim 1 , wherein R 1 and R 2 are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 18 ring atoms.
3 . A material for an organic electroluminescence device, comprising:
Yb, a Yb compound, and/or a Yb complex; and
a compound of formula (I):
wherein
Az is 3-pyridyl,
R 1 and R 2 are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO,
X 1 , X 2 and X 3 are each independently N or CR 3 , at least two of X 1 , X 2 , and X 3 being
R a and R b are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms,
R 3 is hydrogen, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO, and
-(L 1 ) m -(L 2 ) n - is a structure, the dotted lines being bonding sites:
4 . An electronic equipment, comprising:
the organic electroluminescence device of claim 1 .
5 . The organic electroluminescence device of claim 2 , wherein R 1 and R 2 are each independently unsubstituted or substituted phenyl, unsubstituted or substituted biphenyl, unsubstituted or substituted naphthyl, or unsubstituted or substituted fluorenyl.
6 . The organic electroluminescence device of claim 1 , wherein the unsubstituted or substituted aromatic hydrocarbon group is present and has 6 to 18 ring atoms.
7 . The organic electroluminescence device of claim 1 , wherein -(L 1 ) m -(L 2 ) n - is:
8 . The organic electroluminescence device of claim 1 , wherein -(L 1 ) m -(L 2 ) n - is:
9 . The organic electroluminescence device of claim 1 , wherein
-(L 1 ) m -(L 2 ) n - is:
and
R 1 and/or R 2 are phenyl.
10 . The organic electroluminescence device of claim 1 , wherein
-(L 1 ) m -(L 2 ) n - is:
and
R 1 and R 2 are phenyl.
11 . The organic electroluminescence device of claim 1 , wherein
-(L 1 ) m -(L 2 ) n - is:
and
R 1 and R 2 are phenyl.
12 . The organic electroluminescence device of claim 1 , wherein
-(L 1 ) m -(L 2 ) n - is:
13 . The organic electroluminescence device of claim 1 , wherein
-(L 1 ) m -(L 2 ) n - is:
and
R 1 and R 2 are independently phenyl or biphenyl.
14 . The organic electroluminescence device of claim 1 , comprising the Yb as a sole rare earth metal in the rare earth metal layer.
15 . The material of claim 3 , comprising the Yb as a sole rare earth metal in the material.
16 . A material for an organic electroluminescence device, comprising:
Yb, a Yb compound, and/or a Yb complex; and
a compound of formula (I):
wherein
Az is phenanthroline,
R 1 and R 2 are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO,
X 1 , X 2 and X 3 are each independently N or CR 3 , at least two of X 1 , X 2 , and X 3 being N,
R a and R b are each independently an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms,
R 3 is hydrogen, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 30 ring atoms, an unsubstituted or substituted heteroaromatic group having 3 to 30 ring atoms, an unsubstituted or substituted alkyl group having 1 to 25 carbon atoms, an unsubstituted or substituted cycloalkyl group having 3 to 18 ring carbon atoms, CN, or R a R b PO, and
-(L 1 ) m -(L 2 ) n - is one of the following structures, the dotted lines being bonding sites: