ORGANIC ELECTROLUMINESCENCE DEVICE

• US 20090267500A1
• Filed: 04/23/2009
• Published: 10/29/2009
• Est. Priority Date: 04/24/2008
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: YAGI, Kazunari, MURAKAMI, Takeshi, FUKUZAKI, Eiji, TAKEDA, Akira, ISE, Toshihiro, KINOSHITA, Ikuo
• Granted Patent: US 8,153,278 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic electroluminescence device, includes: a pair of electrodes; and at least one organic layer including a light emitting layer, the light emitting layer being provided between the pair of electrodes, wherein at least one layer of the at least one organic layer contains a compound represented by formula (I) as defined in the specification.

Claims

1. An organic electroluminescence device, comprising:

a pair of electrodes; and

at least one organic layer including a light emitting layer, the light emitting layer being provided between the pair of electrodes,

wherein at least one layer of the at least one organic layer contains a compound represented by formula (I);

wherein each of X¹, X², X³, X⁴, X⁵, X⁶, X⁷, X⁸, X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ independently represents an atom selected from the group consisting of carbon and nitrogen;

one or more of X¹, X², X³, X⁴, X⁵, X⁶, X⁷ and X⁸ represents a nitrogen atom;

when each of X¹, X², X³, X⁴, X⁵, X⁶, X⁷, X⁸, X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ can be further substituted, each of X¹, X², X³, X⁴, X⁵, X⁶, X⁷, X⁸, X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ may independently have a substituent;

M represents a divalent metal;

L¹ represents a divalent connecting group;

a broken line expressing a bond between the metal and a nitrogen atom represents a coordinate bond; and

a solid line expressing a bond between the metal and a carbon atom represents a covalent bond.

2. The organic electroluminescence device according to claim 1,

wherein the compound represented by formula (I) is a compound represented by formula (II):

wherein each of X²¹, X²², X²³, X²⁴, X²⁵, X²⁶, X²⁷, X²⁸, X³¹, X³², X³³, X³⁴ and X³⁵ independently represents an atom selected from the group consisting of carbon and nitrogen;

one or more of X²¹, X²², X²³, X²⁴, X²⁵, X²⁶, X²⁷ and X²⁸ represents a nitrogen atom;

when each of X²¹, X²², X²³, X²⁴, X²⁵, X²⁶, X²⁷, X²⁸, X³¹, X³², X³³, X³⁴ and X³⁵ can be further substituted, each of X²¹, X²², X²³, X²⁴, X²⁵, X²⁶, X²⁷, X²⁸, X³¹, X³², X³³, X³⁴ and X³⁵ may independently have a substituent;

L² represents a divalent connecting group;

a broken line expressing a bond between the platinum atom and a nitrogen atom represents a coordinate bond; and

a solid line expressing a bond between the platinum atom and a carbon atom represents a covalent bond.

3. The organic electroluminescence device according to claim 2,

wherein the compound represented by formula (II) is a compound represented by formula (III):

wherein each of X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵, X⁴⁶, X⁴⁷, X⁴⁸, X⁵¹, X⁵², X⁵³, X⁵⁴ and X⁵⁵ independently represents an atom selected from the group consisting of carbon and nitrogen;

one or more of X⁴¹, X⁴², X⁴³ and X⁴⁴ represents a nitrogen atom;

when each of X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵, X⁴⁶, X⁴⁷, X⁴⁸, X⁵¹, X⁵², X⁵³, X⁵⁴ and X⁵⁵ can be further substituted, each of X⁴¹, X⁴², X⁴³, X⁴⁴, X⁴⁵, X⁴⁶, X⁴⁷, X⁴⁸, X⁵¹, X⁵², X⁵³, X⁵⁴ and X⁵⁵ may independently have a substituent;

L³ represents a divalent connecting group;

a broken line expressing a bond between the platinum atom and a nitrogen atom represents a coordinate bond; and

a solid line expressing a bond between the platinum atom and a carbon atom represents a covalent bond.

4. The organic electroluminescence device according to claim 3,

wherein the compound represented by formula (III) is a compound represented by formula (IV):

wherein each of X⁶¹, X⁶², X⁶³, X⁶⁴, X⁶⁵, X⁶⁶, X⁶⁷ and X⁶⁸ independently represents an atom selected from the group consisting of carbon and nitrogen;

one or more of X⁶¹, X⁶², X⁶³ and X⁶⁴ represents a nitrogen atom;

when each of X⁶¹, X⁶², X⁶³, X⁶⁴, X⁶⁵, X⁶⁶, X⁶⁷ and X⁶⁸ can be further substituted, each of X⁶¹, X⁶², X⁶³, X⁶⁴, X⁶⁵, X⁶⁶, X⁶⁷ and X⁶⁸ may independently have a substituent;

each of R⁶¹, R⁶², R⁶³, R⁶⁴ and R⁶⁵ independently represents a hydrogen atom or a substituent;

L⁴ represents a divalent connecting group;

a broken line expressing a bond between the platinum atom and a nitrogen atom represents a coordinate bond; and

a solid line expressing a bond between the platinum atom and a carbon atom represents a covalent bond.

5. The organic electroluminescence device according to claim 4,

wherein the compound represented by formula (IV) is a compound represented by formula (V):

wherein each of X⁷¹, X⁷³, X⁷⁴, X⁷⁵, X⁷⁶, X⁷⁷ and X⁷⁸ independently represents an atom selected from the group consisting of carbon and nitrogen;

when each of X⁷¹, X⁷³, X⁷⁴, X⁷⁵, X⁷⁶, X⁷⁷ and X⁷⁸ can be further substituted, each of X⁷¹, X⁷³, X⁷⁴, X⁷⁵, X⁷⁶, X⁷⁷ and X⁷⁸ may independently have a substituent;

each of R⁷¹, R⁷², R⁷³, R⁷⁴ and R⁷⁵ independently represents a hydrogen atom or a substituent;

L⁵ represents a divalent connecting group;

a broken line expressing a bond between the platinum atom and a nitrogen atom represents a coordinate bond; and

a solid line expressing a bond between the platinum atom and a carbon atom represents a covalent bond.

6. The organic electroluminescence device according to claim 1,

wherein at least one layer of the at least one organic layer contains a material having at least one deuterium atom.

7. The organic electroluminescence device according to claim 1,

wherein the light emitting layer contains a material having at least one deuterium atom.

8. The organic electroluminescence device according to claim 6,

wherein the material having at least one deuterium atom is a material containing any one of a carbazole structure and an indole structure each having at least one deuterium atom.

9. The organic electroluminescence device according to claim 1,

wherein the light emitting layer contains at least one member of a compound represented by formula (a):

wherein each of R₁ to R₄ independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group, an acyl group, an acyloxy group, an amino group, a nitro group, a cyano group, an ester group, an amide group, a halogen atom, a perfluoroalkyl group or a silyl group;

at least one of R₁ to R₄ is a group having a double bond or a triple bond; and

each of X₁ to X₁₂ independently represents a hydrogen group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group, an acyl group, an acyloxy group, an amino group, a nitro group, a cyano group, an ester group, an amide group, a halogen group, a perfluoroalkyl group or a silyl group.