Organometallic complex, organic EL element and organic EL display

• US 20050244673A1
• Filed: 02/25/2005
• Published: 11/03/2005
• Est. Priority Date: 08/27/2002
• Status: Abandoned Application

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujitsu Limited
• Inventors: Sawatari, Norio, Miyatake, Tetsuya, Satoh, Tasuku, Sotoyama, Wataru
• Application Number:
  US11/066,315
• Publication Number:
  US 20050244673A1
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 13/00 Compounds containing elements of Groups 7 or 17 of the Periodic Table
• CPC Class Codes: C07F 13/005 Compounds without a metal-carbon linkage
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/10 Non-macromolecular compounds
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: C09K 2211/187 of the iron group metals, i.e. Fe, Co or Ni
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• 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: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 59/38 comprising colour filters or colour changing media [CCM]
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/341 : Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/346 : comprising platinum
• CPC Class Codes: H10K 85/60 : Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/631 : Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/649 : Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/6565 : Oxadiazole compounds

Abstract

An organic EL element includes an organometallic complex including a rhenium atom; one ligand which has a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium atom, and has at least one π conjugation part; and the other ligand coordinated with the rhenium atom in such a way that the ligand saturates the coordination number of the rhenium atom and the charge of the whole organometallic complex is neutral.

Claims

1. An organic EL element comprising:

a positive electrode;

a negative electrode; and

an organic thin film layer disposed between the positive electrode and the negative electrode,

wherein the organic thin film layer comprises an organometallic complex,

wherein the organometallic complex comprises;

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral.

2. An organic EL element according to claim 1, wherein the organometallic complex is represented by the following formula (1):

wherein, in the formula (1), R¹ and R² may be the same or different, and each represent a hydrogen atom or a substituent group;

“

i” and

“

j”

are integers;

Cy¹ represents one ring structure containing a coordinated nitrogen atom which is coordinated with a rhenium (Re) atom, and two carbon atoms which are bonded to the nitrogen atom and are shared with Cy²;

Cy² represents the other ring structure which is bonded to the oxygen atom bonded to a rhenium (Re) atom and contains the two carbon atoms shared with Cy¹;

“

n”

is 1, 2, or 3, representing a coordination number of the one ligand coordinated with the rhenium (Re) atom bidentately, the one ligand comprising Cy¹ and Cy²;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

3. An organic EL element according to claim 1, wherein the organometallic complex is represented by the following formula (2):

wherein, in the formula (2), R³ and R⁴ may be the same or different, and each represent a hydrogen atom or a substituent group;

“

i” and

“

j”

are integers;

Cy³ represents one ring structure containing a coordinated nitrogen atom which is coordinated with a rhenium (Re) atom, and a carbon atom which is bonded to the nitrogen atom and to a carbon atom in Cy⁴;

Cy⁴ represents the other ring structure containing a carbon atom which is bonded to the oxygen atom bonded to a rhenium (Re) atom and a carbon atom which is bonded to a carbon atom in Cy³;

“

n”

is 1, 2, or 3, representing a coordination number of the one ligand coordinated with the rhenium (Re) atom bidentately, the one ligand comprising Cy¹ and Cy²;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

4. An organic EL element according to claim 1, wherein the organometallic complex is represented by the following formula (3):

wherein, in the formula (3), R¹ to R⁴ may be the same or different, and each represent a hydrogen atom or a substituent group. “

i”

, “

j”

, “

k” and

“

l”

are integers;

Cy¹ represents one ring structure containing a coordinated nitrogen atom which is coordinated with a rhenium (Re) atom, and two carbon atoms which are bonded to the nitrogen atom and are shared with Cy²;

Cy² represents the other ring structure which is bonded to the oxygen atom bonded to a rhenium (Re) atom and contains the two carbon atoms shared with Cy¹;

Cy³ represents one ring structure containing a coordinated nitrogen atom which is coordinated with a rhenium (Re) atom, and a carbon atom which is bonded to the nitrogen atom and to a carbon atom in Cy⁴;

Cy⁴ represents the other ring structure containing a carbon atom which is bonded to the oxygen atom bonded to a rhenium (Re) atom and a carbon atom which is bonded to a carbon atom in Cy³;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents 1 or 2.

24. An organic EL element according to claim 1, which is used for lighting units.

5. An organic EL element comprising:

a positive electrode;

a negative electrode; and

an organic thin film layer disposed between the positive electrode and the negative electrode,

wherein the organic thin film layer comprises an organometallic complex,

wherein the organometallic complex comprises a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated carbon atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral.

6. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (8):

wherein, in the formula (8), R¹ and R² may be the same or different, and each represent a hydrogen atom or a substituent group;

“

i” and

“

j”

are integers;

Cy¹ represents one ring structure having a coordinated nitrogen atom which is coordinated with a rhenium (Re) atom, and a carbon atom which is bonded to a carbon atom in Cy²;

Cy² represents the other ring structure having a coordinated carbon atom which is bonded to a rhenium (Re) atom, and a carbon atom which is bonded to is bonded to the carbon atom a carbon atom in Cy¹;

“

n”

is 1, 2, or 3, representing a coordination number of the one ligand coordinated with the rhenium (Re) atom bidentately, the one ligand comprising Cy¹ and Cy²;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

7. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (9) and the one ligand comprises 7,8-benzoquinoline skeleton:

wherein, in the formula (9), R³ to R¹⁰ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

8. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (10) and the one ligand comprises 2-phenylpyridine skeleton:

wherein, in the formula (10), R³ to R¹⁰ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

9. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (11) and the one ligand comprises 2-phenyloxazoline skeleton:

wherein, in the formula (11), R³ to R⁸ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

10. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (12) and the one ligand comprises 2-phenylthiozoline skeleton:

wherein, in the formula (12), R³ to R⁸ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of o to 4.

11. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (13) and the one ligand comprises 2-(2′

-thienyl)pyridine skeleton;

wherein, in the formula (13), R³ to R⁸ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

12. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (14) and the one ligand comprises 2-(2′

-thienyl)thiozoline skeleton;

wherein, in the formula (14), R³ to R⁸ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

13. An organic EL element according to claim 5, wherein the organometallic complex is represented by the following formula (15) and the one ligand comprises 3-(2′

-thiozolyl)-2H-pyran-2-one skeleton;

wherein, in the formula (15), R³ to R⁶ may be the same or different, each representing a hydrogen atom or a substituent group which may optionally be substituted, wherein an adjacent pair thereof may join together to form an aromatic ring which contains one of a nitrogen atom, a sulphur atom and an oxygen atom;

“

n”

represents an integer of 1 to 3;

the letter “

L”

represents the other ligand which saturates the coordination number of the rhenium (Re) atom, and neutralizes the charge of the whole complex; and

“

m”

represents an integer of 0 to 4.

14. An organic EL element comprising:

a positive electrode;

a negative electrode; and

an organic thin film layer disposed between the positive electrode and the negative electrode,

wherein the organic thin film layer comprises an organometallic complex,

wherein the organometallic complex comprises;

at least one of Group 8 metal atoms selected from Group 8 metal element;

one ligand which contains at least one π

conjugation part and is coordinated with the Group 8 metal atom; and

a dithiolate ligand which is selected from an aliphatic dithiolate ligand and a heteroaromatic dithiolate ligand, and is coordinated with the Group 8 metal atom.

15. An organic EL element according to claim 14, wherein the organometallic complex is represented by the following formula (17):

wherein, in the formula (17), “

M”

represents a Group 8 metal atom;

the letter “

L”

represents a ligand which is coordinated with the Group 8 metal atom one of unidentately and bidentately or more and comprises at least one π

conjugation part;

“

n”

represents an integer of 1 to 6; and

R¹ represents a divalent aliphatic organic group or a divalent heteroaromatic organic group.

16. An organic EL element according to claim 14, wherein the organometallic complex is represented by the following formula (18):

wherein, in the formula (18), “

M”

represents a Group 8 metal atom;

a ligand which is bonded to the M and contains a nitrogen atom, represents a ligand containing at least one π

conjugation part and is coordinated with the M one of unidentately and bidentately or more;

in the ligand containing at least one π

conjugation part, R³ represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, an amino group, an alkyl group, an alkyl acetate group, a cycloalkyl group, a nitrogen atom, an aryl group, or an aryloxy group, these themselves may be substituted with substituent groups, and “

q”

represents an integer of 0 to 8;

“

n”

represents an integer of 1 to 4;

a ligand which is bonded to the M and contains a sulfur atom represents a dithiolate ligand selected from an aliphatic dithiolate ligand and heteroaromatic dithiolate ligand; and

in the dithiolate ligand selected from an aliphatic dithiolate ligand and heteroaromatic dithiolate ligand, R¹ represents a divalent aliphatic organic group or divalent heteroaromatic organic group.

17. An organic EL element according to claim 14, wherein the organometallic complex is represented by the following formula (19).

wherein, in the formula (19), R¹ and R² may be the same or different, and each represent a hydrogen atom or a substituent group;

Cy¹ represents one ring structure having a coordinated nitrogen atom which is coordinated with a platinum (Pt) atom, and a carbon atom which is bonded to the nitrogen atom and a carbon atom in Cy²;

Cy² represents the other ring structure having a coordinated carbon atom which is bonded to a platinum (Pt) atom, and a carbon atom which is bonded to the carbon atom and to a carbon atom in Cy¹;

a ligand which is bonded to the Pt and contains a sulfur atom represents a dithiolate ligand selected from an aliphatic dithiolate ligand and heteroaromatic dithiolate ligand; and

in the dithiolate ligand, R³ represents a divalent aliphatic organic group or a divalent heteroaromatic organic group.

18. An organic EL element according to claim 14, wherein the heteroaromatic dithiolate ligand is an aromatic dithiolate ligand represented by any one of the following formulae (20) to (23).

wherein, in the formulae (20) to (23), R⁴ represents a halogen atom, a cyano group, an alkoxy group, an amino group, an alkyl group, an alkyl acetate group, a cycloalkyl group, a nitrogen atom, an aryl group, or an aryloxy group, these themselves may be substituted with substituent groups;

and “

m”

represents an integer of 0 to 5.

19. An organic EL element according to claim 14, wherein the aliphatic dithiolate ligand is an aliphatic dithiolate ligand represented by one of the following formulae (24) and (25).

wherein, in the formulae (24) and (25), R⁵ and R⁶ may be the same or different, represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, an amino group, an alkyl group, an alkyl acetate group, a cycloalkyl group, a nitrogen atom, an aryl group, or an aryloxy group, and these themselves may be substituted with substituent groups.

20. An organic EL element comprising a color conversion layer,

wherein the color conversion layer is capable of emitting phosphorescence and is capable of converting incident light into light having a wavelength longer than the wavelength thereof by 100 nm or more.

21. An organic EL element according to claim 20, wherein the color conversion layer is capable of converting incident light into light having a wavelength longer than the wavelength thereof by 150 nm or more.

22. An organic EL element according to claim 20, wherein the color conversion layer is capable of converting light in the wavelength range of ultraviolet light to blue light into red light.

23. An organic EL element according to claim 20, wherein the color conversion layer comprises at least one selected from (1) an organometallic complex which comprises a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, (2) an organometallic complex which comprises an rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom, a coordinated carbon atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturate the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, and (3) an organometallic complex which comprises at least one of Group 8 metal atoms selected from Group 8 metal element;

one ligand which comprises at least one π

conjugation part and is coordinated with the Group 8 metal atom; and

a dithiolate ligand which is selected from an aliphatic dithiolate ligand and a heteroaromatic dithiolate ligand, and is coordinated with the Group 8 metal atom.

25. An organometallic complex comprising:

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, and

which organometallic complex is used for an organic EL element.

28. An organometallic complex according to claim 25, which is used as at least one of a luminescent material and a color conversion material.

26. An organometallic complex comprising:

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated carbon atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, and

which organometallic complex is used for an organic EL element.

27. An organometallic complex comprising:

at least one of Group 8 metal atoms selected from Group 8 metal element;

one ligand which comprises at least one π

conjugation part and is coordinated with the Group 8 metal atom; and

a dithiolate ligand which is selected from an aliphatic dithiolate ligand and a heteroaromatic dithiolate ligand, and is coordinated with the Group 8 metal atom, and

which organometallic complex is used for an organic EL element.

29. An organic EL display, comprising an organic EL element, wherein the organic EL element comprises:

a positive electrode;

a negative electrode; and

an organic thin film layer disposed between the positive electrode and the negative electrode,

wherein the organic thin film layer comprises an organometallic complex,

wherein the organometallic complex comprises;

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral.

30. An organic EL display according to claim 29, further comprising:

a pair of electrodes;

an organic thin film layer disposed between the pair of electrodes, which is capable of emitting EL light; and

a color conversion layer,

wherein at least one of the pair of electrodes is transparent and at least one of the pair of electrodes corresponds to pixels,

wherein the color conversion layer is arranged on at least a green pixel and a red pixel in the pixels.

31. An organic EL display according to claim 29, further comprising:

a color conversion layer arranged on a green pixel; and

a color conversion layer arranged on a red pixel,

wherein light-emitting light due to EL luminescence is white light,

wherein the color conversion layer arranged on a red pixel comprises an organometallic complex, wherein the organometallic complex comprises;

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, and

which organometallic complex is used for an organic EL element.

32. An organic EL display according to claim 29, further comprising:

a color conversion layer arranged on a red pixel; and

wherein light-emitting light due to EL luminescence is blue light,

wherein the color conversion layer arranged on a red pixel comprises an organometallic complex, wherein the organometallic complex comprises;

a rhenium (Re) atom;

one ligand which comprises a coordinated nitrogen atom and a coordinated oxygen atom, each coordinated with the rhenium (Re) atom, and comprises at least one π

conjugation part; and

the other ligand coordinated with the rhenium (Re) atom in such a way that the ligand saturates the coordination number of the rhenium (Re) atom and the charge of the whole organometallic complex is neutral, and

which organometallic complex is used for an organic EL element.