IP Library Granted Patent US 7,740,958
Granted Patent B2
US 7,740,958 · App. 11/678,367 · Granted Jun 22, 2010

Organic light-emitting device

Assignee: Canon Kabushiki Kaisha
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Quick Facts
Patent No.
US 7,740,958
App. No.
11/678,367
Granted
Jun 22, 2010
Kind
B2
Abstract

Provided is an organic light-emitting device capable of emitting light with high efficiency by incorporating a silyl compound in which a silyl group and an amino group are directly bonded to an anthracene ring particularly into its light-emitting layer. In the organic light-emitting device including: a pair of electrodes composed of an anode and a cathode; and an organic compound layer interposed between the pair of electrodes, wherein the organic compound layer contains the following silyl compound. A layer containing at least one kind of the silyl compound is a light-emitting layer.

Claims (33)

1. An organic light-emitting device, comprising:

a pair of electrodes composed of an anode and a cathode; and

a light-emitting organic compound layer interposed between the pair of electrodes,

wherein the light-emitting organic compound layer contains a light-emitting compound represented by the following general formula [1]:

where Ar 1 and Ar 2 each represent a group selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, Ar 1 and Ar 2 may be the same or different from each other, and Ar 1 and Ar 2 may be bonded to each other to form a ring,

R 1 , R 2 , and R 3 each represent a group selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, and R 1 , R 2 , and R 3 may be the same or different from one another,

X represents a group selected from the group consisting of a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, and X's may be the same or different from each other, and

a represents an integer of 0 or more to 8 or less.

2. An organic light-emitting device according to claim 1 , wherein the light-emitting layer contains a first compound represented by the general formula [1] and a second compound represented by the following general formula [2]:

where R 4 and R 5 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and R 4 and R 5 may be the same or different from each other,

R 6 and R 7 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, a cyano group, or a halogen atom, R 6 and R 7 may be the same or different from each other, and R 6 's or R 7 's may be the same or different from each other,

Ar 3 and Ar 4 each represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and Ar 3 and Ar 4 may be the same or different from each other,

m represents an integer of 1 or more to 10 or less, and

b and c each represent an integer of 0 or more to 3 or less.

3. An organic light-emitting device according to claim 1 , wherein the light-emitting layer contains a first compound represented by the general formula [1] and a second compound represented by the following general formula [3]:

where R 8 to R 11 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, a cyano group, or a halogen atom, R 8 to R 11 may be the same or different from one another, and R 8 's, R 9 's, R 10 's, or R 11 's may be the same or different from each other,

Ar 5 to Ar 8 each represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and Ar 5 to Ar 8 may be the same or different from one another, and

d, e, f, and g each represent an integer of 0 or more to 3 or less.

4. An organic light-emitting device according to claim 1 , wherein the light-emitting layer contains a first compound represented by the general formula [1] and a second compound represented by the following general formula [4]:

where R 12 and R 13 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and R 12 and R 13 may be the same or different from each other,

R 14 and R 15 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, a cyano group, or a halogen atom, R 14 and R 15 may be the same or different from each other, and R 14 's or R 15 's may be the same or different from each other,

R 16 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and R 16 's may be the same or different from each other,

Z 1 and Z 2 each represent a group selected from the group consisting of a direct single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted aralkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted divalent heterocyclic group, a substituted or unsubstituted silyl group, an ether group, a thioether group, and a carbonyl group, and each of Z 1 and Z 2 may further have a linking group,

Ar 9 and Ar 10 each represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, Ar 9 and Ar 10 may be the same or different from each other, and Ar 9 and Ar 10 may form a ring,

n represents an integer of 1 or more to 10 or less,

h and i each represent an integer of 0 or more to 3 or less, and

j represents an integer of 0 or more to 9 or less.

5. An organic light-emitting device according to claim 1 , wherein the light-emitting layer contains a first compound represented by the general formula [1] and a second compound represented by the following general formula [5]:

where Ar 11 represents a group selected from the group consisting of a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, and, when k represents 2 or more, Ar 11 's may be the same or different from each other,

Z 3 represents a group selected from the group consisting of a direct single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted aralkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted divalent heterocyclic group, a substituted or unsubstituted silyl group, an ether group, a thioether group, and a carbonyl group, Z 3 may further have a linking group, and, when k represents 2 or more, Z 3 's may be the same or different from each other,

R 17 represents a group selected from the group consisting of a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted amino group, and a substituted or unsubstituted silyl group, and, when p represents 2 or more, R 17 's may be the same or different from each other,

k represents an integer of 1 or more to 6 or less, and

p represents an integer of 0 or more to 5 or less provided that a relationship of k+p≦6 is satisfied.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2007
From: SAITOH, AKIHITO; YASHIMA, MASATAKA
To: CANON KABUSHIKI KAISHA
Reel/Frame 018928/0696 →
Priority Claims (1)
JP 2006-056957 · Mar 2, 2006 · national
Continuity (1)
Related Publication 20070207346A1 · Sep 6, 2007