Organic electroluminescence element

Patent metadata

Field	Value
Publication number	US-10428268-B2
Application number	US-201013522126-A
Country	US
Kind code	B2
Filing date	Dec 28, 2010
Priority date	Jan 15, 2010
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

A light emitting organic thin film including at least one compound represented by Formula (PQ-1) and at least one compound represented by Formula (BN-1).

In Formula (PQ-1), each of R a , R b and R c independently represents a hydrogen atom or an alkyl group, wherein any one of R a , R b and R c represents a hydrogen atom and the remaining two represent an alkyl group. Each of R 1 to R 5 independently represents a hydrogen atom, an alkyl group, an aryl group, a fluorine atom or a cyano group. Each of R x and R y independently represents an alkyl group or a phenyl group. In Formula (BN-1), Ar 1 represents an arylene group that may have a substituent Z. Ar 2 represents a condensed hydrocarbyl group that may have a substituent Z. Each of R 101 to R 113 independently represents a phenyl group, or the like.

First claim

The invention claimed is:

1. A light emitting organic thin film comprising at least one compound represented by Formula (PQ-1) and at least one compound represented by Formula (BN-1):

wherein, in Formula (PQ-1), each of R a , R b and R c independently represents a hydrogen atom or an alkyl group, any one of R a , R b and R c represents a hydrogen atom and the remaining two represent an alkyl group, each of R 1 to R 5 independently represents a hydrogen atom, an alkyl group, a phenyl group, a fluorine atom or a cyano group, and each of R x and R y represents a methyl group;
in Formula (BN-1), Ar 1 represents an arylene group that may have a substituent Z, Ar 2 represents a tetracenyl group that may have a substituent Z, each of R 101 to R 113 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenyl group that may have a substituent Z;
the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, an aryloxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof.

2. The light emitting organic thin film according to claim 1 ,
wherein, in Formula (PQ-1), two of R a , R b and R c represent a methyl group and the remaining one represents a hydrogen atom.

3. The light emitting organic thin film according to claim 2 ,
wherein, in Formula (PQ-1), R 1 to R 5 represent a hydrogen atom.

4. The light emitting organic thin film according to claim 1 ,
wherein, in Formula (PQ-1), R a and R c represent an alkyl group and R b represents a hydrogen group.

5. The light emitting organic thin film according to claim 4 ,
wherein, in Formula (PQ-1), R 1 to R 5 represent a hydrogen atom.

6. The light emitting organic thin film according to claim 1 ,
wherein, in Formula (BN-1), R 102 , R 105 , R 108 , R 109 , R 110 , R 111 and R 112 represent a hydrogen atom.

7. The light emitting organic thin film according to claim 1 ,
wherein, in Formula (PQ-1), R a and R c represent an alkyl group and R b represents a hydrogen group, and in Formula (BN-1), R 102 and R 105 represent a hydrogen atom.

8. A composition comprising the compound represented by Formula (PQ-1) and the compound represented by Formula (BN-1):

wherein, in Formula (PQ-1), each of R a , R b and R c independently represents a hydrogen atom or an alkyl group, any one of R a , R b and R c represents a hydrogen atom and the remaining two represent an alkyl group, each of R 1 to R 5 independently represents a hydrogen atom, an alkyl group, a phenyl group, a fluorine atom or a cyano group, and each of R x and R y represents a methyl group;
in Formula (BN-1), Ar 1 represents an arylene group that may have a substituent Z, Ar 2 represents a tetracenyl group that may have a substituent Z, each of R 101 to R 113 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenyl group that may have a substituent Z; and
the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, an aryloxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof.

9. An organic electroluminescence device comprising a pair of electrodes, and an organic layer including a light emitting layer disposed between the electrodes, on a substrate,
wherein the light emitting layer comprises at least one compound represented by Formula (PQ-1) and at least one compound represented by Formula (BN-1):

wherein, in Formula (PQ-1), each of R a , R b and R c independently represents a hydrogen atom or an alkyl group, any one of R a , R b and R c represents a hydrogen atom and the remaining two represent an alkyl group, each of R 1 to R 5 independently represents a hydrogen atom, an alkyl group, a phenyl group, a fluorine atom or a cyano group, and each of R x and R y represents a methyl group;
in Formula (BN-1), Ar 1 represents an arylene group that may have a substituent Z, Ar 2 represents a tetracenyl group that may have a substituent Z, each of R 101 to R 113 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a phenyl group that may have a substituent Z; and
the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, an aryloxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof.

10. The organic electroluminescence device according to claim 9
wherein the compound represented by Formula (BN-1) has no peak current value at 100 K to 150 K as determined by thermally stimulated current of a thin film formed to a film thickness of 100 nm by vacuum deposition of the compound.

11. The organic electroluminescence device according to claim 9 ,
wherein at least one layer of the organic layer is formed by a coating process using a solution or dispersion.

12. A display apparatus using the organic electroluminescence device according to claim 9 .

13. An illumination apparatus using the organic electroluminescence device according to claim 9 .

Assignees

• Ise Toshihiro
• Kitamura Tetsu
• Watanabe Toru
• Udc Ireland Ltd

Inventors

• Ise Toshihiro
• Kitamura Tetsu
• Watanabe Toru

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title