IP Library › Granted Patent US 10,396,299
Granted Patent B2
US 10,396,299 · App. 15/825,566 · Granted Aug 27, 2019

Organic electroluminescent devices and metal complex compounds

Inventors: Kazumi Nii (Kanagawa-ken, JP); Kousuke Watanabe (Kanagawa-ken, JP); Tatsuya Igarashi (Kanagawa-ken, JP); Seiji Ichijima (Kanagawa-ken, JP); Toshihiro Ise (Kanagawa-ken, JP)
Assignee: UDC IRELAND LIMITED
H01L51/0087C07C251/24C07D213/22C07D213/53C07F15/0033C07F15/0086C07F15/0093C09K11/06H01L51/0085H01L51/5012H01L51/5016H01L51/5203H05B33/14C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/182C09K2211/185Y10S428/917
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Quick Facts
Patent No.
US 10,396,299
App. No.
15/825,566
Granted
Aug 27, 2019
Kind
B2
Abstract

An organic electroluminescent device, which has a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes, wherein at least one layer between the pair of electrodes comprises at least one metal complex having a tridentate- or higher polydentate-chain structure ligand.

Claims (60)

1. An organic electroluminescent device, comprising:

a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes,

wherein at least one layer between the pair of electrodes comprises at least one metal complex represented by formula (6) having a tetradentate or higher polydentate chain structure ligand:

wherein M 61 represents a metal ion;

Q 61 and Q 62 each represent a group to form a ring;

the ring formed by Q 61 or Q 62 may bond to Z 61 or Z 68 respectively via a linking bond, to form a ring;

Y 61 represents a linking group, a single bond or a double bond;

Y 62 and Y 63 each represent a linking group or a single bond;

L 65 represents a ligand to coordinate to M 61 ;

Z 61 , Z 62 , Z 63 , Z 64 , Z 65 , Z 66 , Z 67 , and Z 68 each represent a substituted or unsubstituted carbon atom or a nitrogen atom;

Z 61 and Z 62 , Z 62 and Z 63 , Z 63 and Z 64 , Z 65 and Z 66 , Z 66 and Z 67 , Z 67 and Z 68 each may bond to each other via a linking group, to form a condensed ring; and

n 61 represents 0 to 4.

2. The organic electroluminescent device of claim 1 , wherein in the complex represented by formula (6), at least one ring formed with Q 61 or Q 62 is a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring, or a condensed ring thereof.

3. The organic electroluminescent device of claim 1 , wherein in the complex represented by formula (6), Y 62 and Y 63 each independently represent a single bond, a carbonyl-linking group, an alkylene linking group, or an alkenylene group.

4. The organic electroluminescent device of claim 1 , wherein in the complex represented by formula (6), Y 61 is a single bond or an alkylene group.

5. The organic electroluminescent device of claim 1 , wherein the organic layer comprises at least one luminescent layer and a hole transporting layer, and the organic layer further comprises at least one layer selected from the group consisting of an exciton-blocking layer, a hole injection layer, a hole-blocking layer and an electron-transporting layer.

6. The organic electroluminescent device of claim 1 , wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is selected from the group consisting of an amine compound, a metal chelate oxynoid compound in which the metal is aluminum, zinc or a transition metal, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound.

7. The organic electroluminescent device of claim 1 , wherein the organic layer comprises at least one electron-transporting layer in which an electron-transporting material is selected from the group consisting of a metal chelate oxynoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound.

8. An organic electroluminescent device, comprising:

a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes,

wherein at least one layer between the pair of electrodes comprises at least one metal complex represented by formula (7) having a tetradentate or higher polydentate chain structure ligand:

wherein M 71 represents a metal ion;

Y 71 , Y 72 , and Y 73 each represent a linking group or a single bond;

L 75 represents a ligand to coordinate to M 71 ;

Z 71 , Z 72 , Z 73 , Z 74 , Z 75 , and Z 76 each represent a substituted or unsubstituted carbon atom or a nitrogen atom;

Z 71 and Z 72 , and Z 73 and Z 74 each may bond to each other via a linking group to form a condensed ring;

R 71 , R 72 , R 73 , and R 74 each represent a hydrogen atom or a substituent; and

n 71 represents 0 to 4.

9. The organic electroluminescent device of claim 8 , wherein in the complex represented by formula (7), R 71 , R 72 , R 73 , and R 74 are each an alkyl group, an aryl group, or a group that forms a condensed ring by forming a bond between R 71 and R 72 , or between R 73 and R 74 .

10. The organic electroluminescent device of claim 8 , wherein in the complex represented by formula (7), Y 72 and Y 73 each independently represent a single bond, a carbonyl-linking group, an alkylene linking group, or an alkenylene group.

11. The organic electroluminescent device of claim 8 , wherein in the complex represented by formula (7), Y 71 is a single bond or an alkylene group.

12. The organic electroluminescent device of claim 8 , wherein the organic layer comprises at least one luminescent layer and a hole transporting layer, and the organic layer further comprises at least one layer selected from the group consisting of an exciton-blocking layer, a hole injection layer, a hole-blocking layer and an electron-transporting layer.

13. The organic electroluminescent device of claim 8 , wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is selected from the group consisting of an amine compound, a metal chelate oxynoid compound in which the metal is aluminum, zinc or a transition metal, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound.

14. The organic electroluminescent device of claim 8 , wherein the organic layer comprises at least one electron-transporting layer in which an electron-transporting material is selected from the group consisting of a metal chelate oxynoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound.

15. The organic electroluminescent device of claim 8 , wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is composed of at least two compounds.

16. A metal complex represented by formula (6) having a tetradentate or higher polydentate chain structure ligand:

wherein M 61 represents a metal ion;

Q 61 and Q 62 each represent a group to form a ring;

the ring formed by Q 61 or Q 62 may bond to Z 61 or Z 68 respectively via a linking bond, to form a ring;

Y 61 represents a linking group, a single bond or a double bond;

Y 62 and Y 63 each represent a linking group or a single bond;

L 65 represents a ligand to coordinate to M 61 ;

Z 61 , Z 62 , Z 63 , Z 64 , Z 65 , Z 66 , Z 67 , and Z 68 each represent a substituted or unsubstituted carbon atom or a nitrogen atom;

Z 61 and Z 62 , Z 62 and Z 63 , Z 63 and Z 64 , Z 65 and Z 66 , Z 66 and Z 67 , Z 67 and Z 68 each may bond to each other via a linking group, to form a condensed ring; and

n 61 represents 0 to 4.

17. The metal complex of claim 16 , wherein in the complex represented by formula (6), at least one ring formed with Q 61 or Q 62 is a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring, or a condensed ring thereof.

18. The metal complex of claim 16 , wherein in the complex represented by formula (6), Y 62 and Y 63 each independently represent a single bond, a carbonyl-linking group, an alkylene linking group, or an alkenylene group.

19. The metal complex of claim 16 , wherein in the complex represented by formula (6), Y 61 is a single bond or an alkylene group.

20. A metal complex represented by formula (7):

Formula (7) having a tetradentate or higher polydentate chain structure ligand:

wherein M 71 represents a metal ion;

Y 71 , Y 72 , and Y 73 each represent a linking group or a single bond;

L 75 represents a ligand to coordinate to M 71 ;

Z 71 , Z 72 , Z 73 , Z 74 , Z 75 , and Z 76 each represent a substituted or unsubstituted carbon atom or a nitrogen atom;

Z 71 and Z 72 , and Z 73 and Z 74 each may bond to each other via a linking group to form a condensed ring;

R 71 , R 72 , R 73 , and R 74 each represent a hydrogen atom or a substituent; and

n 71 represents 0 to 4.

21. The metal complex of claim 20 , wherein in the complex represented by formula (7), R 71 , R 72 , R 73 , and R 74 are each an alkyl group, an aryl group, or a group that forms a condensed ring by forming a bond between R 71 and R 72 , or between R 73 and R 74 .

22. The metal complex of claim 20 , wherein in the complex represented by formula (7), Y 72 and Y 73 each independently represent a single bond, a carbonyl-linking group, an alkylene linking group, or an alkenylene group.

23. The metal complex of claim 20 , wherein in the complex represented by formula (7), Y 71 is a single bond or an alkylene group.

Priority Claims (2)
JP 2003-157006 · Jun 2, 2003 · national
JP 2004-092274 · Mar 26, 2004 · national
Continuity (5)
Continuation 14554725 · Nov 26, 2014
Continuation 13420289 · Mar 14, 2012
Division 12395358 · Feb 27, 2009
Division 10551653
Related Publication 20180083208A1 · Mar 22, 2018
Cited By (1)
US 12,745,558