IP Library Granted Patent US 9,296,944
Granted Patent B2
US 9,296,944 · App. 13/522,045 · Granted Mar 29, 2016

Organic electroluminescence device

Inventors: Toshihiro Ise (Kanagawa, JP); Tetsu Kitamura (Kanagawa, JP); Toru Watanabe (Kanagawa, JP)
Assignee: UDC Ireland
C09K11/06H01L51/0054H01L51/0058H05B33/14C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/185H01L51/0085H01L51/5016H01L51/5268
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Quick Facts
Patent No.
US 9,296,944
App. No.
13/522,045
Granted
Mar 29, 2016
Kind
B2
Abstract

Provided is an organic electroluminescence device having a low drive voltage and excellent durability. Provided also is an organic electroluminescence device having low dependency of voltage increment after driving on temperature of usage environment. A light emitting organic thin film containing at least one compound represented by Formula (PQ-1) and a hydrocarbon compound having a specific structure, and an organic electroluminescence device using the same. 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.

Claims (48)

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 (Ch-1):

wherein 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, 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,

each of R 101 to R 110 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,

each of R 111 to R 115 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, provided that any one of R 111 to R 115 represents a condensed hydrocarbyl group that may have a substituent Z,

each of R 121 to R 125 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, provided that any one of R 121 to R 125 represents a condensed hydrocarbyl group that may have a substituent Z, and

the substituent Z represents an alkyl group, an alkenyl group, a phenyl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof, and a plurality of substituents Z may be bonded to each other to form an aryl ring.

2. The light emitting organic thin film according to claim 1 ,

wherein the compound represented by Formula (Ch-1) has no peak current value at 100K to 150K as determined by thermally stimulated current of a thin film formed to a film thickness of 100 nm by vacuum deposition of the compound.

3. The light emitting organic thin film according to claim 1 ,

wherein two of R a , R b and R c represent a methyl group and the remaining one represents a hydrogen atom.

4. The light emitting organic thin film according to claim 3 ,

wherein R 1 to R 5 represent a hydrogen atom.

5. The light emitting organic thin film according to claim 1 ,

wherein R a and R c represent an alkyl group, and R b represents a hydrogen group.

6. The light emitting organic thin film according to claim 1 ,

wherein R 101 to R 110 represent a hydrogen atom.

7. The light emitting organic thin film according to claim 1 ,

wherein any one of R 111 to R 115 represents a naphthyl or a phenanthryl group and the others represent a hydrogen atom, and

any one of R 121 to R 125 represents a naphthyl or a phenanthryl group and the others represent a hydrogen atom.

8. The light emitting organic thin film according to claim 1 ,

wherein R a and R c represent an alkyl group and R b represents a hydrogen group, and

any one of R 111 to R 115 represents a naphthyl or a phenanthryl group and the others represent a hydrogen atom, and

any one of R 121 to R 125 represents a naphthyl or a phenanthryl group and the others represent a hydrogen atom.

9. The light emitting organic thin film according to claim 1 ,

wherein a content of Cl, Br and I contained in the light emitting organic thin film is 100 ppm or less.

10. A composition comprising a compound represented by Formula (PQ-1) and a compound represented by Formula (Ch-1):

wherein 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, 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,

each of R 101 to R 110 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,

each of R 111 to R 115 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, provided that any one of R 111 to R 115 represents a condensed hydrocarbyl group that may have a substituent Z,

each of R 121 to R 125 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, provided that any one of R 121 to R 125 represents a condensed hydrocarbyl group that may have a substituent Z, and

the substituent Z represents an alkyl group, an alkenyl group, a phenyl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof, and a plurality of substituents Z may be bonded to each other to form an aryl ring.

11. 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 is the light emitting organic thin film according to claim 1 .

12. The organic electroluminescence device according to claim 11 ,

wherein at least one layer of the organic layer is formed by a coating process using a solution or dispersion.

13. A display apparatus using the organic electroluminescence device according to claim 11 .

14. An illumination apparatus using the organic electroluminescence device according to claim 11 .

15. 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 is the light emitting organic thin film according to claim 1 , and

the compound represented by Formula (Ch-1) of claim 1 has no peak current value at 100K to 150K as determined by thermally stimulated current of a thin film formed to a film thickness of 100 nm by vacuum deposition of the compound.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2013
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 029731/0363 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2012
From: ISE, TOSHIHIRO; KITAMURA, TETSU; WATANABE, TORU
To: FUJIFILM CORPORATION
Reel/Frame 028542/0049 →
Priority Claims (1)
JP 2010-007537 · Jan 15, 2010 · national
Continuity (1)
Related Publication 20120319568A1 · Dec 20, 2012