ORGANIC ELECTROLUMINESCENCE DEVICE, NOVEL PLATINUM COMPLEX COMPOUND AND NOVEL COMPOUND CAPABLE OF BEING A LIGAND THEREOF

• US 20090261721A1
• Filed: 04/21/2009
• Published: 10/22/2009
• Est. Priority Date: 04/22/2008
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Murakami, Takeshi, Ise, Toshihiro, Kinoshita, Ikuo, Takizawa, Hiroo, Takada, Saki, Takeda, Akira
• Granted Patent: US 8,216,698 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: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• 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 (1) 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 (1);

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of X⁵, X⁶, X⁷, X⁸, X⁹ and X¹⁰ independently represents a carbon atom or a nitrogen atom;

each of X¹¹ and X¹² independently represents a carbon atom or a nitrogen atom;

each of X¹³, X¹⁴ and X¹⁵ independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom;

the number of the nitrogen atom contained in a 5-membered ring structure represented by X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ is not more than 2;

each of Z¹ and Z² independently represents a nitrogen atom or a phosphorus atom;

L represents a single bond or a divalent connecting group; and

M represents a divalent metal ion.

2. The organic electroluminescence device according to claim 1,

wherein the compound represented by formula (1) is a compound represented by formula (2):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of X⁵, X⁶, X⁷, X⁸, X⁹ and X¹⁰ independently represents a carbon atom or a nitrogen atom;

each of X¹¹ and X¹² independently represents a carbon atom or a nitrogen atom;

each of X¹³, X¹⁴ and X¹⁵ independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom;

the number of the nitrogen atom contained in a 5-membered ring structure represented by X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ is not more than 2;

L represents a single bond or a divalent connecting group; and

M represents a divalent metal ion.

3. The organic electroluminescence device according to claim 2,

wherein the compound represented by formula (2) is a compound represented by formula (3):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of X⁵, X⁶, X⁷, X⁸, X⁹ and X¹⁰ independently represents a carbon atom or a nitrogen atom;

each of X¹¹ and X¹² independently represents a carbon atom or a nitrogen atom;

each of X¹³, X¹⁴ and X¹⁵ independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom;

the number of the nitrogen atom contained in a 5-membered ring structure represented by X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ is not more than 2; and

L represents a single bond or a divalent connecting group.

4. The organic electroluminescence device according to claim 3,

wherein the compound represented by formula (3) is a compound represented by formula (4):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X¹¹ and X¹² independently represents a carbon atom or a nitrogen atom;

each of X¹³, X¹⁴ and X¹⁵ independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom;

the number of the nitrogen atom contained in a 5-membered ring structure represented by X¹¹, X¹², X¹³, X¹⁴ and X¹⁵ is not more than 2; and

L represents a single bond or a divalent connecting group.

5. The organic electroluminescence device according to claim 4,

wherein the compound represented by formula (4) is a compound represented by formula (4a-1):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X⁵³, X⁵⁴ and X⁵⁵ independently represents a carbon atom or a nitrogen atom;

the number of the nitrogen atom contained in a 5-membered ring structure containing X⁵³, X⁵⁴ and X⁵⁵ is 1 or 2; and

L represents a single bond or a divalent connecting group.

6. The organic electroluminescence device according to claim 5,

wherein the compound represented by formula (4a-1) is a compound represented by formula (4a-2):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X⁵³ and X⁵⁴ independently represents a carbon atom or a nitrogen atom;

the number of the nitrogen atom contained in a 5-membered ring structure containing X⁵³ and X⁵⁴ is 1 or 2;

R⁷⁵ represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.

7. The organic electroluminescence device according to claim 6,

wherein the compound represented by formula (4a-2) is a compound represented by formula (4a-3):

wherein each of X¹, X² and X⁴ independently represents a carbon atom or a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X⁵³ and X⁵⁴ independently represents a carbon atom or a nitrogen atom;

the number of the nitrogen atom contained in a 5-membered ring structure containing X⁵³ and X⁵⁴ is 1 or 2;

R⁷⁵ represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.

8. The organic electroluminescence device according to claim 4,

wherein the compound represented by formula (4) is a compound represented by formula (4b-1):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

X⁶¹ represents a carbon atom or a nitrogen atom;

each of X¹³, X¹⁴ and X¹⁵ independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom;

the number of the nitrogen atom contained in a 5-membered ring structure represented by X⁶¹, the carbon atom, X¹³, X¹⁴ and X¹⁵ is not more than 2; and

L represents a single bond or a divalent connecting group.

9. The organic electroluminescence device according to claim 8,

wherein the compound represented by formula (4b-1) is a compound represented by formula (4b-2):

wherein each of X¹, X², X³ and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X², X³ and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X⁹⁴ and X⁹⁵ independently represents a carbon atom or a nitrogen atom;

at least one of X⁹⁴ and X⁹⁵ represents a carbon atom;

R⁹³ represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.

10. The organic electroluminescence device according to claim 9,

wherein the compound represented by formula (4b-2) is a compound represented by formula (4b-3):

wherein each of X¹, X² and X⁴ independently represents a carbon atom or a nitrogen atom;

one or more of X¹, X² and X⁴ represent a nitrogen atom;

each of R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵ and R⁴⁶ independently represents a hydrogen atom or a substituent;

each of X⁹⁴ and X⁹⁵ independently represents a carbon atom or a nitrogen atom;

at least one of X⁹⁴ and X⁹⁵ represents a carbon atom;

R⁹³ represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.

11. The organic electroluminescence device according to claim 1,

wherein the light emitting layer contains at least one member of the compound represented by formula (1).

12. 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.

13. The organic electroluminescence device according to claim 12,

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.

14. A compound represented by formula (4a-4):

wherein each of R¹, R², R⁴, R⁶, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁷⁴ and R⁷⁵ independently represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.

15. A compound represented by the following formula (4a-4′

);

wherein each of R¹, R², R⁴, R⁶, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁷¹, R⁷⁴ and R⁷⁵ independently represents a hydrogen atom or a substituent; and

L represents a single bond or a divalent connecting group.