Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-9512137-B2
Application number	US-201113509878-A
Country	US
Kind code	B2
Filing date	Aug 5, 2011
Priority date	Aug 5, 2010
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

An organic electroluminescence device sequentially includes an anode, an emitting layer, an electron-transporting region, and a cathode, the electron-transporting region including an electron-transporting material that includes a cyano group and an aromatic ring group.

First claim

The invention claimed is:

1. An organic electroluminescence device comprising, in order: an anode, an emitting layer, an electron-transporting region, and a cathode, the electron-transporting region comprising an electron-transporting material has a formula (ET),
A a L 1 -Ar 1 CN) b ) c   (ET)

wherein L 1 is a single bond or a substituted or unsubstituted (a+1)-valent aromatic ring group having 6 to 50 ring carbon atoms, Ar 1 is a substituted or unsubstituted (1+b)-valent aromatic ring group having 6 to 50 ring carbon atoms, a, b, and c are each independently an integer from 1 to 3, when L 1 and Ar1 have a substituent, the substituent is unsubstituted and selected from the group consisting of an alkyl group, an alkylsilyl group, a halogenated alkyl group, a phenyl group, a biphenyl group, terphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a 9,9-dimethylfluorenyl group, a benzanthryl group, a pyrenyl group, a cycloalkyl group, an alkoxy group, a heterocyclic group that does not include a nitrogen atom, an alkoxycarbonyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, and a carboxyl group, and A is a fused aromatic ring group having a formula selected from the group consisting of formulas (A-3), and A(5) to (A-7),

wherein c of R 31 to R 40 , R 51 to R 60 , R 61 to R 72 , or R 73 to R 86 , bond to L 1 as a single bond, and the remainder of R 1 to R 12 , R 21 to R 30 , R 31 to R 40 , R 51 to R 60 , R 61 to R 72 , or R 73 to R 86 , are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, wherein adjacent groups among the remainder of R 31 to R 40 , R 51 to R 60 , R 61 to R 72 , or R 73 to R 86 , may bond to form a ring.

2. The organic electroluminescence device of claim 1 , wherein the electron-transporting region further comprises a reducing dopant.

3. The organic electroluminescence device of claim 2 , wherein the reducing dopant is at least one substance selected from the group consisting of an alkali metal, an alkaline-earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline-earth metal oxide, an alkaline-earth metal halide, a rare earth metal oxide, a rare earth metal halide, an organic complex of art alkali metal, an organic complex of an alkaline-earth metal, and an organic complex of a rare earth metal.

4. A compound comprising a cyano group and an aromatic ring group, having a formula (ET),
A a L 1 -Ar 1 CN) b ) c   (ET)

wherein L 1 is a single bond or a substituted or unsubstituted (a+1)-valent aromatic ring group having 6 to 50 ring carbon atoms, Ar 1 is a substituted or unsubstituted (1+b)-valent aromatic ring group having 6 to 50 ring carbon atoms, a, b, and c are each independently an interger from 1 to 3, when L 1 and Ar 1 have a substituent, the substituent is unsubstituted and selected from the group consisting of an alkyl group, an alkylsilyl group, a halogenated alkyl group, a phenyl group, a biphenyl group, terphenyl group, a naphthyl group , a phenanthryl group, an anthryl group, a 9,9-dimethylfluorenyl group, a benzanthryl group, a pyrenyl group, a cycloalkyl group, an alkoxy group, a heterocyclic group that does not include a nitrogen atom, an alkoxycatbonyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, and a carboxyl group, and A is a fused aromatic ring group having a formula selected from the group consisting of formulas (A-3), and A(5) to (A-7),

wherein c of R 31 to R 40 , R 51 to R 60 , to R 61 to R 72 , or R 73 to R 86 bond to L 1 as a single bond, and the remainder of R 1 to R 12 , R 21 to R 30 , R 31 to R 40 , R 51 to R 60 , R 61 to R 72 , or R 73 to R 86 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, wherein adjacent groups among the remainder of R 31 to R 40 , R 51 to R 60 , R 61 to R 72 , or R 73 to R 86 may bond to forma ring.

5. The organic electroluminescence device of claim 1 , wherein the electron-transporting material comprises a fused aromatic ring group.

6. The organic electroluminescence device of claim 1 , wherein the electron-transporting material comprises a fused aromatic ring group.

7. The organic electroluminescence device of claim 1 , wherein the electron-transporting material comprises both a monocyclic aromatic ring group and a fused aromatic ring group.

8. The organic electroluminescence device of claim 5 , wherein the monocyclic aromatic ring group is a phenyl group, a biphenyl group, or a terphenyl group.

9. The organic electroluminescence device of claim 6 , wherein the fused aromatic ring group is a naphthyl group, a phenanthryl group, an anthryl group, a 9,9-dimethylfluorenyl group, a fluoranthenyl group, a benzanthryl group, a pyrcnyl group, a dihenzothiophenyl group, or a dibenzolliranyl group.

10. The organic electroluminescence device of claim 1 , further comprising a hole-transporting region between the anode and the emitting layer.

11. The organic electroluminescence device of claim 1 , wherein L 1 is a substituted or unsubstituted (a+1)-valent aromatic ring group having 6 to 12ring carbon atoms.

12. The organic electroluminescence device of claim 1 , wherein the (1+b)-valent aromatic ring group is a residue that corresponds to a phenyl group or a naphthyl group.

13. The organic electroluminescence device of claim 1 , wherein the emitting layer comprises an anthracene compound having a formula (4),

wherein Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic aromatic ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused aromatic ring group having 8 to 50 ring , a combination of the monocyclic aromatic ring group and the fused aromatic ring group, and R 101 to R 108 are each independently a group selected from a hydrogen atom, a substituted or unsubstituted monocyclic aromatic ring group having 5 to 50 ring atoms, a substituted or unsubstituted fused aromatic ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic aromatic ring roup and the fused aromatic ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.

14. The organic electroluminescence device of claim 1 , wherein the emitting layer comprises a pyrene compound having a formula (5),

Assignees

• Ito Hirokatsu
• Saito Hiroyuki
• Mizuki Yumiko
• Kawamura Masahiro
• Kawamura Yuichiro
• Idemitsu Kosan Co

Inventors

• Ito Hirokatsu
• Saito Hiroyuki
• Mizuki Yumiko
• Kawamura Masahiro
• Kawamura Yuichiro

Classifications

• C07C255/52

  to carbon atoms of six-membered aromatic rings being part of condensed ring systems · CPC title

• C07C2103/48

  Chemistry & Metallurgy · mapped topic

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• H01L51/5048

  Electricity · mapped topic

• C07C255/51

  containing at least two cyano groups bound to the carbon skeleton · CPC title