IP Library Granted Patent US 8,710,493
Granted Patent B2
US 8,710,493 · App. 13/386,826 · Granted Apr 29, 2014

Organic electroluminescent element

Inventors: Kazuki Nishimura (Sodegaura, JP); Toshinari Ogiwara (Sodegaura, JP); Hitoshi Kuma (Sodegaura, JP); Kenichi Fukuoka (Sodegaura, JP); Chishio Hosokawa (Sodegaura, JP); Yukitoshi Jinde (Sodegaura, JP)
Assignee: Idemitsu Kosan Co., Ltd.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,710,493
App. No.
13/386,826
Granted
Apr 29, 2014
Kind
B2
Abstract

An organic electroluminescence device includes an anode, a cathode and layers between the anode and the cathode, the layers at least including a hole transporting layer, a first emitting layer, a second emitting layer and an electron transporting layer, in which the first emitting layer includes a first host material and a first luminescent material and the second emitting layer is continuously formed on the first emitting layer near the cathode and includes a second host material and a second luminescent material. The second host material is a monoazine derivative, a diazine derivative, or a triazine derivative. The first and second luminescent materials are different metal complexes.

Claims (87)

1. An organic electroluminescence device comprising:

an anode,

a cathode; and

layers between the anode and the cathode, the layers comprising a hole transporting layer, a first emitting layer, a second emitting layer, and an electron transporting layer, wherein

the first emitting layer comprises a first host material and a first luminescent material,

the second emitting layer is continuously formed on the first emitting layer near the cathode and comprises a second host material and a second luminescent material,

the second host material is a monoazine derivative, a diazine derivative, or a triazine derivative, wherein a monoazine ring of the monoazine derivative, a diazine ring of the diazine derivative and a triazine ring of the triazine derivative are optionally fused with a ring structure except for a nitrogen-containing five-membered ring structure, and

the first and second luminescent materials are different metal complexes.

2. The organic electroluminescence device of claim 1 , wherein

the first and second host materials are different from each other.

3. The organic electroluminescence device according to claim 1 , wherein

the first host material is an amine derivative.

4. The organic electroluminescence device of claim 3 , wherein

the amine derivative comprises a compound of at least one formula selected from the group consisting of formulae (1), (2), (3), (4), (5), (6), and (7):

wherein in formula (1), Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;

in formulae (2) to (7), Ar 5 to Ar 16 are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms, a substituted or unsubstituted aryl group having 8 to 40 carbon atoms bonded with an aromatic amino group, or a substituted or unsubstituted aryl group having 8 to 40 carbon atoms bonded with an aromatic heterocyclic group;

in formulae (1) to (7), each of Ar 1 to Ar 16 is independently optionally a ladder-type furan;

in formulae (1) to (7), Ar 1 , Ar 3 , Ar 5 , Ar 8 , Ar 10 , Ar 12 , and Ar 15 are each independently optionally respectively bonded to Ar 2 , Ar 4 , Ar 6 , Ar 9 , Ar 11 , Ar 13 , and Ar 16 to form a ring;

in formulae (2), (4), (6), and (7), L 1 to L 7 are each independently a direct bond or a bonding group having 1 to 30 carbon atoms;

in formulae (1) to (7), R 1 to R 23 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted non-fused aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted fused aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted aryl group of both fused and non-fused rings having 12 to 40 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkyl amino group having 1 to 40 carbon atoms, a substituted or unsubstituted aralkyl amino group having 7 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted aralkylsilyl group having 8 to 40 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 40 carbon atoms; and

in formulae (4), (6), and (7), X 1 to X 6 are each independently a sulfur atom, an oxygen atom, or a nitrogen atom substituted by a monoaryl group.

5. The device of claim 4 , wherein the amine derivative comprises a compound of formula (1), and wherein Ar 2 , Ar 3 , or both are a naphthyl group.

6. The organic electroluminescence device of claim 1 , wherein

the second host material comprises a carbazole skeleton.

7. The organic electroluminescence device of claim 6 , wherein

the second host material comprises a compound of at least one formula selected from the group consisting of formulae (8), (9), (10), (11), and (12):

wherein: in formulae (8) to (11), Ar 101 to Ar 104 are each indepedently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms;

in formulae (8) to (11), R 110 to R 111 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted non-fused aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted fused aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted aryl group of both fused and non-fused rings having 12 to 40 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkyl amino group having 1 to 40 carbon atoms, a substituted or unsubstituted aralkyl amino group having 7 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted aralkylsilyl group having 8 to 40 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 40 carbon atoms;

in formulae (8) to (11), n is an integer of from 1 to 4, m is an integer of from 1 to 4, and a sum (n+m) of n and m satisfies a relationship of 2≦(n+m)≦5;

in formula (12), R 121 to R 128 each are independently a hydrogen atom, an aryl group, or an alkyl group, or are bonded with a skeleton of formula (12A);

in formulae (12) and (12A), each X is independently N or CH, with the proviso that from 1 to 4 of groups X are N;

when R 121 to R 128 are bonded with the skeleton of formula (12A), at least one combination selected from the group consisting of R 121 and R 122 , R 122 and R 123 , R 123 and R 124 , R 125 and R 126 , R 126 and R 127 , and R 127 and R 128 is bonded with the skeleton of formula (12A); and

in formula (12A), R 129 is a hydrogen atom, an aryl group, or an alkyl group.

8. The organic electroluminescence device of claim 6 , wherein

the second host material comprises a compound of at least one formula selected from the group consisting of formulae (8A), (9A), (10A), and (11A):

wherein Ar 101 to Ar 104 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 60 carbon atoms, with the proviso that Ar 101 to Ar 103 are not all hydrogen atoms in formulae (8A), (9A), and (11A), and Ar 101 to Ar 104 are not all hydrogen atoms in formula (10A);

R 110 to R 112 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted non-fused aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted fused aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted aryl group of both fused and non-fused rings having 12 to 40 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkyl amino group having 1 to 40 carbon atoms, a substituted or unsubstituted aralkyl amino group having 7 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted aralkylsilyl group having 8 to 40 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 40 carbon atoms; and

n is an integer of from 1 to 4, m is an integer of from 1 to 4, and a sum (n+m) of n and m satisfies a relationship of 2≦(n+m)≦5.

9. The organic electroluminescence device of claim 6 , wherein

the second host material comprises a compound of formula (13):

wherein in formula (13), A 1 is a substituted or unsubstituted nitrogen-containing heterocyclic group having 1 to 30 ring carbon atoms, with the proviso that A 1 does not comprise a carbazolyl group or an indolyl group;

A 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted nitrogen-containing heterocyclic group having 1 to 30 ring carbon atoms;

X 1 and X 2 are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted fused aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms;

Y 1 to Y 4 are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted fused aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms, or a substituted or unsubstituted fused aromatic heterocyclic group having 2 to 30 ring carbon atoms, with the proviso that at least two adjacent groups selected from the group consisting of Y 1 to Y 4 are optionally bonded to each other to form a cyclic structure;

p and q each are independently an integer of from 1 to 4, and r and s each are independently an integer of from 1 to 3;

when p, q, r, and s each are greater than 1, Y 1 to Y 4 are optionally the same or different; and

at least one group selected from the group consisting of A 1 , A 2 , X 1 , X 2 , Y 1 , Y 2 , Y 3 , and Y 4 is a group derived from a monoazine derivative, a diazine derivative, or a triazine derivative.

10. The organic electroluminescence device of claim 6 , wherein

the second host material comprises a compound of formula (14) or (15):

wherein each X is independently CH or N, with the proviso that at least one of X is N;

Ar 21 to Ar 23 each independently are a substituted or unsubstituted non-fused aromatic hydrocarbon group or aromatic heterocyclic group; and

Ar 22 and Ar 23 each optionally forms a fused ring with a ring including X.

11. The organic electroluminescence device of claim 6 , wherein

the second host material comprises a compound of formula (16), (17), or both:

wherein in formula (16), Ar 23 is a divalent bonding group comprising a substituted or unsubstituted non-fused aromatic hydrocarbon group or aromatic heterocyclic group;

R 217 and R 220 are each independently a hydrogen atom, a substituted or unsubstituted non-fused aromatic hydrocarbon group, or an aromatic heterocyclic group;

R 222 and R 223 are each independently a substituted or unsubstituted non-fused aromatic hydrocarbon group or aromatic heterocyclic group; and

R 216 , R 218 , R 219 and R 221 are a hydrogen atom, alkyl group, aralkyl group, alkynyl group, cyano group, dialkylamino group, diarylamino group, diaralkylamino group, amino group, nitro group, acyl group, alkoxycarbonyl group, carboxyl group, alkoxyl group, alkylsulfonyl group, haloalkyl group, hydroxyl group, amido group, substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group;

at least one group selected from the group consisting of Ar 23 , R 216 , R 217 , R 218 , R 219 , R 220 , R 221 , R 222 , and R 223 is a group derived from a monoazine derivative, a diazine derivative or a triazine derivative,

in formulae (17) and (17A), rings F and F′ are each independently a heterocyclic ring fused to an adjacent ring;

F and F′ are each independently of a formula (17A);

Ar 24 is a divalent bonding group including a substituted or unsubstituted non-fused aromatic hydrocarbon group or aromatic heterocyclic group;

R 230 to R 232 each independently are a substituted or unsubstituted non-fused aromatic hydrocarbon group or aromatic heterocyclic group;

R 224 to R 229 each independently are a hydrogen atom, alkyl group, aralkyl group, alkenyl group, alkynyl group, cyano group, dialkylamino group, diarylamino group, diaralkylamino group, amino group, nitro group, acyl group, alkoxycarbonyl group, carboxyl group, alkoxyl group, alkylsulfonyl group, haloalkyl group, hydroxyl group, amido group, substituted or unsubstituted aromatic hydrocarbon group, or substituted or unsubstituted aromatic heterocyclic group;

at least one group selected from the group consisting of Ar 24 , R 224 , R 225 , R 226 , R 227 , R 228 , R 229 , R 230 , R 231 , and R 232 is a group derived from a monoazine derivative, a diazine derivative, or a triazine derivative.

12. The organic electroluminescence device of claim 1 , wherein

the second host material has a higher affinity level than the first host material.

13. The organic electroluminescence device of claim 1 , wherein

the second host material has a higher ionization potential than the first host material.

14. The organic electroluminescence device of claim 1 , wherein

the first and second luminescent materials each independently comprise iridium (Ir), palladium (Pd), platinum (Pt), or a combination thereof.

15. The organic electroluminescence device of claim 14 , wherein

each of the first and second luminescent materials is independently an ortho-metalated complex of formula (20),

wherein A 31 is a ring bonded to A 32 and Q, and is a substituted or unsubstituted aromatic hydrocarbon ring group or a substituted or unsubstituted aromatic heterocyclic ring;

A 32 is an aromatic heterocyclic group bonded to A 31 and is a substituted or unsubstituted aromatic heterocyclic group comprising nitrogen in an aromatic hetero ring,

a ring comprising A 31 and a ring comprising A 32 are optionally bonded to each other at portions other than A 31 and A 32 to form a fused ring or an unsaturated ring;

Q is palladium (Pd), iridium (Ir), or platinum (Pt);

L is a bidentate ligand; and

m and n are each an integer, wherein, when Q is a divalent metal, n=2 and m=0, and when Q is a trivalent metal, n=3 and m=0, or n=2 and m=1.

16. The organic electroluminescence device of claim 1 , wherein

the first luminescent material has a luminescence peak of a wavelength of 570 nm or more, and

the second luminescent material has a luminescence peak of a wavelength of 565 nm or less.

17. The device of claim 1 , wherein a triplet energy gap (Eg(T)) of the first host material is 2.4 eV or more.

18. The device of claim 1 , wherein an ionization potential difference between the first host material and a material of the hole transporting layer is 0.2 eV or less.

19. The device of claim 1 , wherein a hole mobility of the first host material is larger than a hole mobility of the second host material.

20. The device of claim 1 , wherein the second host material comprises a compound of at least one formula selected from the group consisting of formulae (21), (22), (23), (24), (25), and (26):

wherein R 101 to R 105 are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or an alkyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2012
From: NISHIMURA, KAZUKI; OGIWARA, TOSHINARI; KUMA, HITOSHI; FUKUOKA, KENICHI; HOSOKAWA, CHISHIO; JINDE, YUKITOSHI
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 027597/0806 →
Priority Claims (3)
JP 2010-118160 · May 24, 2010 · national
JP 2010-234926 · Oct 19, 2010 · national
JP 2011-096087 · Apr 22, 2011 · national
Continuity (1)
Related Publication 20120119197A1 · May 17, 2012