IP Library Granted Patent US 9,260,658
Granted Patent B2
US 9,260,658 · App. 13/585,981 · Granted Feb 16, 2016

Organic electroluminescence element, lighting device and display device

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Quick Facts
Patent No.
US 9,260,658
App. No.
13/585,981
Granted
Feb 16, 2016
Kind
B2
Abstract

Provided is an organic electroluminescence element containing an anode, a cathode and a plurality of organic layers including a light emitting layer sandwiched between the anode and the cathode, wherein at least one of the organic layers contains: a blue phosphorescence organic metal complex which is coordinated with a ligand having a structure represented by Formula (1); and a compound represented by Formula (H1), provided that Formula (H1) includes a structure represented by Formula (H2),

Claims (47)

1. An organic electroluminescence element comprising an anode, a cathode and a plurality of organic layers including a light emitting layer sandwiched between the anode and the cathode,

wherein at least one of the plurality of organic layers contains:

a blue phosphorescence organic metal complex represented by Formula (2-1); and

a compound represented by Formula (H1),

wherein, Ar represents an aromatic hydrocarbon ring, an aromatic heterocycle, a non-aromatic hydrocarbon ring, or a non-aromatic heterocycle; R 1 and R 2 each respectively represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group, or a non aromatic heterocyclic group, provided that these groups may have a substituent, and that at least one of R 1 and R 2 is an alkyl group having 2 or more carbon atoms or a cycloalkyl group; R a , R b and R c , each respectively represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, provided that these groups may have a substituent; na and nc each respectively represent an integer of 1 or 2; and nb represents an integer of 1 to 4; L′ represents a monoanionic bidentate ligand which is coordinated to M; M represents Ir; m′ represents an integer of 0 to 2, n′ represents an integer of 1 to 3, provided that m′+n′ is equal to 3,

Q m -L n   Formula (H1)

wherein, L is a condensed aromatic heterocycle which may have a substituent; Q is an aromatic hydrocarbon ring or aromatic heterocycle which may have a substituent; n and m each respectively represent an integer of 1 to 3, provided that when n is 2 or more, a plurality of Ls may be the same or different with each other, when m is 2 or more, a plurality of Qs may be the same or different with each other, provided that the compound represented by Formula (H1) includes a structure represented by

wherein, A represents an oxygen atom, a sulfur atom, NR′, or CR″═CR″; A 12 to A 23 each respectively represent a nitrogen atom or CR″, R′ and R″ each respectively represent a linking position, a hydrogen atom, or a substituent, provided that when there are a plurality of CR″s, each CR″ may be the same or different, and the plurality of CR″s may be joined to form a ring.

2. The organic electroluminescence element of claim 1 , wherein, Formula (H1) is further represented by any one of Formulas (H3) to (H102),

3. The organic electroluminescence element of claim 1 ,

wherein, A in Formula (H2) represents an oxygen atom, a sulfur atom, or NR′.

4. The organic electroluminescence element of claim 1 ,

wherein, L in Formula (H1) is further represented by Formula (H2′),

wherein, A′ represents an oxygen atom, a sulfur atom, or NR′″; A′ 11 to A′ 18 each respectively represent a nitrogen atom or CR″″, R′″ and R″″ each respectively represent a linking position, a hydrogen atom, or a substituent, provided that when there are a plurality of CR″″s, each CR″″ may be the same or different, and the plurality of CR″″s may be joined to form a ring.

5. The organic electroluminescence element of claim 4 ,

wherein all of A′ 11 to A′ 18 in Formula (H2′) represent CR″″.

6. The organic electroluminescence element of claim 1 ,

wherein, R 1 and R 2 in Formula (1) represents an alkyl group having 2 or more carbon atoms or a cycloalkyl group.

7. The organic electroluminescence element of claim 1 ,

wherein, at least one of R 1 and R 2 in Formula (1) represents a branched alkyl group having 3 or more carbon atoms.

8. The organic electroluminescence element of claim 1 ,

wherein, both R 1 and R 2 in Formula (1) represent a branched alkyl group having 3 or more carbon atoms.

9. The organic electroluminescence element of claim 1 ,

wherein, Ar in Formula (1) represents a benzene ring.

10. An organic electroluminescence element comprising an anode, a cathode, and a plurality of organic layers including a light emitting layer sandwiched between the anode and the cathode,

wherein at least one of the plurality of organic layers contains:

a blue phosphorescence organic metal complex represented by Formula (2-1); and

a compound represented by Formula (H1),

wherein, Ar represents an aromatic hydrocarbon ring, an aromatic heterocycle, a non-aromatic hydrocarbon ring, or a non-aromatic heterocycle; R 1 and R 2 each respectively represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group; provided that these groups may have a substituent, and that at least one of R 1 and R 2 is an alkyl group having 2 or more carbon atoms or a cycloalkyl group; Ra, Rb and Rc each respectively represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, a non- aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, provided that these groups may have a substituent; na and nc each respectively represent an integer of 1 or 2; and nb represents an integer of 1 to 4; L′represents a monoanionic bidentate ligand which is coordinated to M; M represents Ir; m′represents an integer of 0 to 2, n′ represents an integer of 1 to 3, provided that m′+n′ is equal to 3,

Q m -L n   Formula (H1)

wherein, L is a condensed aromatic heterocycle which may have a substituent, at least one of Ls represents a carbazole ring; Q is an aromatic hydrocarbon ring or aromatic heterocycle which may have a substituent; n represent an integer of 2 or 3, and m represent an integer of 1 to 3, a plurality of Ls may be the same or different with each other, provided that when m is 2 or more, a plurality of Qs may be the same or different with each other, provided that the compound represented by Formula (H1) includes a structure represented by Formula (H2),

wherein, A represents an oxygen atom, a sulfur atom, NR″, or CR″═CR″; A 11 to A 23 each respectively represent a nitrogen atom or CR″, R′ and R″ each respectively represent a linking position, a hydrogen atom, or a substituent, provided that when there are a plurality of CR″s, each CR″ may be the same or different, and the plurality of CR″s may be joined to form a ring.

11. The organic electroluminescence element of claim 10 , wherein, Formula (H1) is further represented by any one of Formulas (H3) to (H102),

12. The organic electroluminescence element of claim 10 ,

wherein, A in Formula (H2) represents an oxygen atom, a sulfur atom, or NR′.

13. The organic electroluminescence element of claim 10 , wherein, L in Formula (H1) is further represented by Formula (H2′),

wherein, A′ represents an oxygen atom, a sulfur atom, or NR″′; A′ 11 to A′ 18 each respectively represent a nitrogen atom or CR″″, R′″ and R″″ each respectively represent a linking position, a hydrogen atom, or a substituent, provided that when there are a plurality of CR″″s, each CR″″ may be the same or different, and the plurality of CR″″s may be joined to form a ring.

14. The organic electroluminescence element of claim 13 ,

wherein all of A′ 11 to A′ 18 in Formula (H2′) represent CR″″.

15. The organic electroluminescence element of claim 10 ,

wherein, R 1 and R 2 in Formula (1) represents an alkyl group having 2 or more carbon atoms or a cycloalkyl group.

16. The organic electroluminescence element of claim 10 ,

wherein, at least one of R 1 and R 2 in Formula (1) represents a branched alkyl group having 3 or more carbon atoms.

17. The organic electroluminescence element of claim 10 ,

wherein, both R 1 and R 2 in Formula (1) represent a branched alkyl group having 3 or more carbon atoms.

18. The organic electroluminescence element of claim 10 ,

wherein, Ar in Formula (1) represents a benzene ring.

Assignments (5)
NUNC PRO TUNC ASSIGNMENT Recorded Feb 10, 2026
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 073741/0073 →
NUNC PRO TUNC ASSIGNMENT Recorded Oct 7, 2021
From: KONICA MINOLTA INC
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 057748/0075 →
NUNC PRO TUNC ASSIGNMENT Recorded Oct 7, 2021
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 057748/0146 →
MERGER Recorded Dec 15, 2015
From: KONICA MINOLTA HOLDINGS, INC.
To: KONICA MINOLTA, INC.
Reel/Frame 037290/0234 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2012
From: KATAKURA, RIE; TAKA, HIDEO
To: KONICA MINOLTA HOLDINGS, INC.
Reel/Frame 028789/0001 →