IP Library Granted Patent US 9,960,356
Granted Patent B2
US 9,960,356 · App. 13/899,029 · Granted May 1, 2018

Organic electroluminescence device, lighting equipment and display device

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Quick Facts
Patent No.
US 9,960,356
App. No.
13/899,029
Granted
May 1, 2018
Kind
B2
Abstract

Provided are an organic electroluminescence device which has a high luminous efficiency, a low operating voltage and a long life and which is low in a voltage rise in operation and excellent in an ageing stability and has an aptitude in production by the wet process, and a lighting equipment and a display device which are prepared by using the same. The above organic electroluminescence device is constituted from organic layers including at least a light-emitting layer which are interposed between an anode and a cathode, wherein at least one layer of the above organic layers contains a blue phosphorescent organic metal complex having a structure represented by the following Formula (1) and a compound represented by the following Formula (H1):

Claims (44)

1. An organic electroluminescence device in which organic layers including at least a light-emitting layer are interposed between an anode and a cathode, wherein at least one layer of the organic layers contains a blue phosphorescent organic metal complex having a structure represented by the following Formula (1) and a compound represented by the following Formula (H1):

wherein m represents an integer of 1 to 2, and n represents an integer of 1 to 2; and m+n is 3; a ring Am, a ring An, a ring Bm and a ring Bn represent a five-membered or six-membered aromatic hydrocarbon ring or aromatic heterocycle; Ar represents an aromatic hydrocarbon ring or an aromatic heterocycle; R1m, R2m, R1n and R2n each represent independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and they may have substituents; Ra, Rb and Rc each represent independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy 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, and they may have substituents; Ra may form a ring with Ar; na and nc represent 1 or 2, and nb represents an integer of 1 to 4; and

wherein X represents an oxygen atom or a sulfur atom; L represents a single bond or a linkage group derived from an aromatic hydrocarbon ring or an aromatic heterocycle; Aro and Ar′ each represent independently an aromatic hydrocarbon ring or an aromatic heterocycle; l represents an integer of 0 to 3, and l′ represents an integer of 0 to 4,

wherein in Formula (H1), l is 0,

wherein Formula (H1) is represented by the following Formula (H2):

wherein X represents an oxygen atom or a sulfur atom; Aro and Ar′ each represent independently an aromatic hydrocarbon ring or an aromatic heterocycle; and l′ represents an integer of 0 to 4,

wherein in Formula (H2), l′ is 1,

wherein Formula (H2) is represented by the following Formula (H3):

wherein X represents an oxygen atom or a sulfur atom; Aro and Ar″ each represent independently an aromatic hydrocarbon ring or an aromatic heterocycle; and l″ represents an integer of 0 to 5.

2. The organic electroluminescence device as described in claim 1 , wherein all of R1m, R2m, R1n and 2n are an alkyl group or a cycloalkyl group having 2 or more carbon atoms.

3. The organic electroluminescence device as described in claim 1 , wherein all of R1m, R2m, R1n and 2n are a branched alkyl group having 3 or more carbon atoms.

4. The organic electroluminescence device as described in claim 1 , wherein in Formula (1), m is 2, and n is 1.

5. The organic electroluminescence device as described in claim 1 , wherein the ring Bm and the ring Bn in Formula (1) are a benzene ring.

6. The organic electroluminescence device as described claim 1 , wherein Ar in Formula (1) is a benzene ring.

7. The organic electroluminescence device as described in claim 1 , wherein Formula (1) is represented by the following Formula (2):

wherein m represents an integer of 1 to 2, and n represents an integer of 1 to 2; and m+n is 3; Ar represents an aromatic hydrocarbon ring or an aromatic heterocycle; R1m, R2m, R1n and R2n each represent independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and they may have substituents; Ra, Rb and Rc each represent independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy 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, and they may have substituents; Ra may form a ring with Ar; na and nc represent 1 or 2, and nb represents an integer of 1 to 4.

8. The organic electroluminescence device as described in claim 1 , wherein a luminescent color is white.

9. A lighting equipment comprising the organic electroluminescence device as described in claim 1 .

10. A display device comprising the organic electroluminescence device as described in claim 1 .

11. The organic electroluminescence device as described in claim 1 , wherein in Formula (1), Ar represents an aromatic hydrocarbon ring or an aromatic heterocycle selected from a benzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, an anthracene ring, a phenanthrene ring, a chrysene ring, a naphthacene ring, a triphenylene ring, an o-terphenyl ring, a m-terphenyl ring, a p-terphenyl ring, an acenaphthene ring, a coronene ring, a fluorene ring, a fluoranthrene ring, a naphthacene ring, a pentacene ring, a perylene ring, a pentaphene ring, a picene ring, a pyrene ring, a pyranthrene ring, an anthranthrene ring, a silole ring, a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an indole ring, a benzimidazole ring, a benzthiazole ring, a benzoxazole ring, a quinoxaline ring, a quinazoline ring, a phthalazine ring, a thienothiophene ring, a carbazole ring, an azacarbazole ring (represents a ring obtained by substituting at least one of optional carbon atoms constituting a carbazole ring with a nitrogen atom), a dibenzosilole ring, a dibenzofuran ring, a dibenzothiophene ring, rings obtained by substituting at least one of optional carbon atoms constituting a benzothiophene ring and a benzofuran ring with a nitrogen atom, a benzodifuran ring, a benzodithiophene ring, an acridine ring, a benzoquinoline ring, a phenazine ring, a phenanzhridine ring, a phenanthroline ring, a cyclazine ring, a quindoline ring, a tepenidine ring, a quinindoline ring, a triphenodithiazine ring, a triphenodioxazine ring, a phenanthrazine ring, an anthrazine ring, a perimidine ring, a naphthofuran ring, a naphthothiophene ring, a naphthodifuran ring, a naphthodithiophene ring, an anthrafuran ring, an anthradifuran ring, an anthrathiophene ring, an anthradithiophene ring, a thianthrene ring, a phenoxatiin ring, a dibenzocarbazole ring, an indolocarbazole ring, a dithienobenzene ring, or an indoloindole ring.

12. The organic electroluminescence device as described in claim 1 , wherein in Formula (H1), Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle selected from a benzene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a pyridine ring, a pyrazine ring, or a triazine ring.

13. The organic electroluminescence device as described in claim 1 , wherein in Formula (H1), Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle selected from a benzene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

14. An organic electroluminescence device in which organic layers including at least a light-emitting layer are interposed between an anode and a cathode, wherein at least one layer of the organic layers contains a blue phosphorescent organic metal complex having a structure represented by the following Formula (1-1) and a compound represented by the following Formula (H1-1):

wherein m represents an integer of 3, and n represents an integer of 0; a ring Am and a ring Bm each represents a five-membered or six-membered aromatic hydrocarbon ring or an aromatic heterocycle; Ar represents an aromatic hydrocarbon ring or an aromatic heterocycle; R1m and R2m represent independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and they may have substituents; Ra, Rb and Rc each represents independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy 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, and they may have substituents; Ra may form a ring with Ar; na and nc represent 1 or 2, and nb represents an integer of 1 to 4; and

wherein X represents an oxygen atom or a sulfur atom; L represents a single bond or a linkage group derived from an aromatic hydrocarbon ring or an aromatic heterocycle; Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle; Ar′ represents an aromatic hydrocarbon ring; l represents an integer of 0 or 1, and l′ represents an integer of 0 to 4,

wherein in Formula (H1-1), l is 0,

wherein Formula (H1-1) is represented by the following Formula (H2-1):

wherein X represents an oxygen atom or a sulfur atom; Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle; Ar′ represents an aromatic hydrocarbon ring; and l′ represents an integer of 0 to 4,

wherein in Formula (H2-1), l′ is 1,

wherein Formula (H2-1) is represented by the following Formula (H3-1):

wherein X represents an oxygen atom or a sulfur atom; Aro and Ar″ each represents independently an aromatic hydrocarbon ring or an aromatic heterocycle; and l″ represents an integer of 0 to 5.

15. The organic electroluminescence device as described in claim 14 , wherein R1m and R2m are an alkyl group or a cycloalkyl group having 2 or more carbon atoms.

16. The organic electroluminescence device as described in claim 14 , wherein R1m and R2m are a branched alkyl group having 3 or more carbon atoms.

17. The organic electroluminescence device as described in claim 14 , wherein the ring Bm in Formula (1-1) is a benzene ring.

18. The organic electroluminescence device as described claim 14 , wherein Ar in Formula (1-1) is a benzene ring.

19. The organic electroluminescence device as described in claim 14 , wherein Formula (1-1) is represented by the following Formula (2-1):

wherein m represents an integer of 3, and n represents an integer of 0; Ar represents an aromatic hydrocarbon ring, or an aromatic heterocycle; R1m and R2m each represents independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and they may have substituents; Ra, Rb and Rc each represents independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy 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, and they may have substituents; Ra may form a ring with Ar; na and nc represent 1 or 2, and nb represents an integer of 1 to 4.

20. The organic electroluminescence device as described in claim 14 , wherein in Formula (H1-1), Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle selected from a benzene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a pyridine ring, a pyrazine ring, or a triazine ring.

21. The organic electroluminescence device as described in claim 14 , wherein in Formula (H1-1), Aro represents an aromatic hydrocarbon ring or an aromatic heterocycle selected from a benzene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring.

22. The organic electroluminescence device as described in claim 1 , wherein in Formula (1), m is 1, and n is 2.

23. The organic electroluminescence device as described in claim 1 , wherein in Formula (H3), l″ represents an integer of 1 to 5.

24. The organic electroluminescence device as described in claim 1 , wherein in Formula (1), R1m, R2m, R1n and R2n each represents independently a non-aromatic hydrocarbon ring or a non-aromatic heterocycle and may have substituents.

25. The organic electroluminescence device as described in claim 14 , wherein in Formula (H3-1), l″ represents an integer of 1 to 5.

26. The organic electroluminescence device as described in claim 14 , wherein in Formula (1-1), R1m and R2m each represents independently a non-aromatic hydrocarbon ring or a non-aromatic heterocycle and may have substituents.

Assignments (4)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2013
From: HIKIME, MAYUKA; ISHIGE, OSAMU; OSHIYAMA, TOMOHIRO; KATAKURA, RIE
To: KONICA MINOLTA, INC.
Reel/Frame 030459/0001 →