IP Library Granted Patent US 10,428,268
Granted Patent B2
US 10,428,268 · App. 13/522,126 · Granted Oct 1, 2019

Organic electroluminescence element

Inventors: Toshihiro Ise (Kanagawa, JP); Tetsu Kitamura (Kanagawa, JP); Toru Watanabe (Kanagawa, JP)
Assignee: UDC Ireland Limited
C09K11/06H01L51/0058H01L51/0085H05B33/14C07F15/0033C09K2211/1029C09K2211/185H01L51/006H01L51/0037H01L51/0059H01L51/0072H01L51/0081H01L51/5016
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Quick Facts
Patent No.
US 10,428,268
App. No.
13/522,126
Granted
Oct 1, 2019
Kind
B2
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.

Claims (31)

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 .

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 028545/0323 →
Priority Claims (1)
JP 2010-007540 · Jan 15, 2010 · national
Continuity (1)
Related Publication 20120292608A1 · Nov 22, 2012