IP Library › Granted Patent US 7,501,189
Granted Patent B2
US 7,501,189 · App. 11/254,852 · Granted Mar 10, 2009

White organic electroluminescent device

Assignee: Idemitsu Kosan Co., Ltd.
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Quick Facts
Patent No.
US 7,501,189
App. No.
11/254,852
Granted
Mar 10, 2009
Kind
B2
Abstract

A white organic electroluminescent device ( 1 ) including an emitting layer ( 5, 6 and 7 ) interposed between an anode ( 2 ) and a cathode ( 9 ), the emitting layer ( 5, 6 and 7 ) emitting blue light, green light and red light, the emitting layer ( 6 ) containing a green dopant that is an aromatic amine compound represented by formula ( 1 ), wherein A 1 , A 2 and R 12 are a hydrogen atom, an alkyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an arylamino group, an alkylamino group or a halogen atom; d and e are independently 1 to 5; h is 1 to 9; R 11 is a secondary or tertiary alkyl or cycloalkyl group; f is 1 to 9; g is 0 to 8 and f+g+h is 2 to 10.

Claims (66)

1. A white organic electroluminescent device comprising an emitting layer interposed between an anode and a cathode,

the emitting layer comprising a host material including a unsymmetric anthracene compound represented by formula (2-1), a blue dopant, a green dopant and a red dopant, and emitting blue light, green light and red light,

wherein the blue dopant is at least one compound selected from styryl amines, amine-substituted styryl compounds, amine-substituted condensed aromatic rings and condensed-aromatic-ring containing compounds;

the green dopant is an aromatic amine compound represented by formula (1);

the red dopant is a compound containing a fluoranthene or perylene skeleton;

the affinity levels of the blue dopant, the green dopant and the red dopant satisfying the relationship

Af b <Af g <Af r ,

wherein Af g is 2.8 to 3.4 eV and

wherein Af b is the affinity level of the blue dopant, Af g is the affinity level of the green dopant and Af r is the affinity level of the red dopant; and

formulae (1) and (2-1) are:

wherein Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nucleus carbon atoms;

Ar′ is a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms;

X is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group. a nitro group or a hydroxyl group; and

a, b and c are each an integer of 0 to 4 and n is an integer of 1 to 3;

 wherein A 1 to A 2 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted aryamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms or a halogen atom; d and e are independently an integer of 1 to 5; h is an integer of 1 to 9; when d and e are independently 2 or more, A 1 s and A 2 s may be the same or different and may be joined together to form a saturated or unsaturated ring; provided that compounds where both of A 1 and A 2 are hydrogen atoms are excluded;

R 11 is a substituted or unsubstituted secondary or tertiary alkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted secondary or tertiary cycloalkyl group having 3 to 10 carbon atoms; f is an integer of 1 to 9; when f is 2 or more, R 11 s may be the same or different; R 12 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, or a halogen atom; g is an integer of 0 to 8; when g is 2 or more, R 12 s may be the same or different; and

f+g+h is an integer of 2 to 10.

2. The white organic electroluminescent device according to claim 1 , wherein the emitting layer has a three-layer structure of a blue emitting layer emitting blue light, a green emitting layer emitting green light and a red emitting layer emitting red light.

3. The white organic electroluminescent device according to claim 1 , wherein the emitting layer has a two-layer structure of a blue emitting layer emitting blue light, and a green/red emitting layer emitting green light and red light.

4. The white organic electroluminescent device according to claim 1 . wherein

the ionization potential of the green dopant is equal to or larger than the ionization potential of the blue dopant.

5. A white organic electroluminescent device comprising in sequence an anode, a blue emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a blue dopant, a green emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a green dopant, a red emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a red dopant, and a cathode,

wherein the blue dopant is at least one compound selected from styryl amines, amine-substituted styryl compounds, amine-substituted condensed aromatic rings and condensed-aromatic-ring containing compounds;

the green dopant is an aromatic amine compound represented by formula (1);

the red dopant is a compound containing a fluoranthene or perylene skeleton;

the affinity levels of the blue dopant and the green dopant satisfying the relationship

Af b <Af g ,

wherein Af g is 2.8 to 3.4 eV and

wherein Af b is the affinity level of the blue dopant and Af g is the affinity level of the green dopant;

the ionization potential of a green dopant forming the green emitting layer being equal to or larger than the ionization potential of a blue dopant forming the blue emitting layer; and

formulae (1) and (2-1) are:

 wherein Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nucleus carbon atoms;

Ar′ is a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms;

X is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substitute or unsubstituted arylthio group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; and

a, b, and c are each an integer of 0 to 4 and n is an integer of 1 to 3;

 wherein A 1 to A 2 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted aryamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms or a halogen atom; d and e are independently an integer of 1 to 5; h is an integer of 1 to 9; when d and e are independently 2 or more, A 1 s and A 2 s may be the same or different and may be joined together to form a saturated or unsaturated ring; provided that compounds where both of A 1 and A 2 are hydrogen atoms are excluded;

R 11 is a substituted or unsubstituted secondary or tertiary alkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted secondary or tertiary cycloalkyl group having 3 to 10 carbon atoms; f is an integer of 1 to 9; when f is 2 or more, R 11 s may be the same or different; R 12 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, or a halogen atom; g is an integer of 0 to 8; when g is 2 or more, R 12 s may be the same or different; and

f+g+h is an integer of 2 to 10.

6. A white organic electroluminescent device comprising in sequence an anode, a blue emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a blue dopant, a red emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a red dopant, a green emitting layer comprising a host material including an unsymmetric anthracene compound represented by formula (2-1) and a green dopant, and a cathode,

wherein the blue dopant is at least one compound selected from styryl amines, amine-substituted styryl compounds, amine-substituted condensed aromatic rings and condensed-aromatic-ring containing compounds;

the green dopant is an aromatic amine compound represented by formula (1);

the red dopant is a compound containing a fluoranthene or perylene skeleton;

the affinity levels of the green dopant and the red dopant satisfying the relationship

Af g <Af r ,

wherein Af g is 2.8 to 3.4 eV and

wherein Af g is the affinity level of the green dopant and Af r is the affinity level of the red dopant;

the ionization potential of a green dopant forming the green emitting layer being equal to larger than the ionization potential of a blue dopant forming the blue emitting layer; and

formulae (1) and (2-1) are:

 wherein Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nucleus carbon atoms;

Ar′ is a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms;

X is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nucleus carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; and

a, b and c are each an integer of 0 to 4 and n is an integer of 1 to 3;

 wherein A 1 to A 2 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted aryamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms or a halogen atom; d and e are independently an integer of 1 to 5; h is an integer of 1 to 9; when d and e are independently 2 or more, A 1 s and A 2 s may be the same or different and may be joined together to form a saturated or unsaturated ring; provided that compounds where both of A 1 and A 2 are hydrogen atoms are excluded;

R 11 is a substituted or unsubstituted secondary or tertiary alkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted secondary or tertiary cycloalkyl group having 3 to 10 carbon atoms; f is an integer of 1 to 9; when f is 2 or more, R 11 s may be the same or different; R 12 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 nucleus carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted arylamino group having 5 to 50 nucleus carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, or a halogen atom; g is an integer of 0 to 8; when g is 2 or more, R 12 s may be the same or different; and

f+g+h is an integer of 2 to 10.

7. The white organic electroluminescent device according to claim 5 , wherein the

affinity levels of the blue dopant, the green dopant and the red dopant satisfy the relationship

Af b <Af g <Af r ,

wherein Af g is 2.8 to 3.4 eV and

wherein Af b is the affinity level of the blue dopant, Af g is the affinity level of the green dopant and Af r is the affinity level of the red dopant.

8. The white organic electroluminescent device according to claim 6 , wherein the

affinity levels of the blue dopant, the green dopant and the red dopant satisfy the relationship

Af b <Af g <Af r ,

wherein Af g is 2.8 to 3.4 eV and

wherein Af b is the affinity level of the blue dopant, Af g is the affinity level of the green dopant and Af r is the affinity level of the red dopant.

9. The white organic electroluminescent device according to claim 1 , wherein the unsymmetric anthracene compound comprises only one anthracene ring.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2006
From: TOKAILIN, HIROSHI; KUMA, HITOSHI; KUBOTA, MINEYUKI; FUNAHASHI, MASAKAZU
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 017152/0896 →
Priority Claims (1)
JP 2004-158285 · May 27, 2004 · national
Continuity (2)
Continuation PCTJP200500924400 · May 20, 2005
Related Publication 20060127698A1 · Jun 15, 2006