Isomer-mixture metal complex composition, organic electroluminescent element, illuminator, and display device

Patent metadata

Field	Value
Publication number	US-2016056396-A1
Application number	US-201414780253-A
Country	US
Kind code	A1
Filing date	Mar 20, 2014
Priority date	Mar 29, 2013
Publication date	Feb 25, 2016
Grant date	—

Abstract

An isomer-mixture metal complex composition that includes a plurality of atropisomers is described. This isomer-mixture metal complex composition is a metal complex composition which is a mixture of isomers each comprising a metal atom and a plurality of ligands, and is characterized by containing a plurality of atropisomers because at least one of the ligands has an aromatic ring as a substituent and the free rotation of the axis of the bonding between the aromatic ring and the ligand is inhibited by the formation of a complex of the metal atom with other ligand(s). An organic EL element using the isomer-mixture metal complex composition as a material for organic EL element is also described. Further, an illuminator and a display device which are obtained using the organic EL element are described.

First claim

1 . A mixed isomeric metal complex composition comprising atropisomers, wherein
each of the atropisomers comprises a metal atom and multiple ligands, at least one of the ligands has an aromatic ring as a substituent, and the atropisomers are present due to hindered free rotation of a bond axis between the aromatic ring and the at least one ligand after formation of a complex with the metal atom and the ligands.

2 . The mixed isomeric metal complex composition according to claim 1 , wherein the atropisomers are present due to hindered free rotation of the bond axis between the aromatic ring and the at least one ligand by another ligand in the complex.

3 . An organic electroluminescent metal complex composition comprising the mixed isomeric metal complex composition comprising atropisomers according to claim 1 , wherein the mixed isomeric metal complex composition is a phosphorescent material for organic electroluminescent elements.

4 . The organic electroluminescent metal complex composition according to claim 3 , the atropisomers being represented by Formula (1):

where rings Am, An, Bm, and Bn each represent a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle, and optionally have a substituent; Xm 1 , Xm 2 , Xm 1 , Xm 4 , Xm 5 , Xn 1 , Xn 2 , Xn 1 , Xn 4 , and Xn 5 in the rings Am, Bm, An, and Bn each represent a carbon atom or a nitrogen atom;
if Xm 1 and M and Xn 1 and M form coordination bonds, Xm 4 and M and Xn 4 and M form covalent bonds;
if Xm 1 and M and Xn 1 and M form covalent bonds, Xm 4 and M and Xn 4 and M form coordination bonds; and
Ar m and Ar n each represent an aromatic hydrocarbon ring or an aromatic heterocyclic group having no symmetrical axis in a bond axis to the ring Bm or Bn, and optionally have a substituent; M represents iridium or platinum; m and n each represent an integer of 0 to 3; m+n represents 2 or 3.

5 . The organic electroluminescent metal complex composition according to claim 4 , wherein the ring Bm, Bn, Am, or An in Formula (1) represents an imidazole or pyrazole ring.

6 . The organic electroluminescent metal complex composition according to claim 4 , wherein a ligand formed through bonding of the rings An and Bn or a ligand formed through the rings Am and Bm in Formula (1) is represented by Formula (2), (3), (5), or (6):

where R 5a1 and R 5a2 each independently represent 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 aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group, and optionally have a substituent; p represents an integer of 0 to 4;
R 5b1 , R 5b2 , and R 5c1 represent an alkyl group, an aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group, and optionally have a substituent; X 5a and X 5b each independently represent ═C(R 5e )— or ═N—; R 5e represents an alkyl group, an aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group;
Ar 51 and Ar 52 each independently represent an aromatic hydrocarbon ring represented by Formula (4):

where R 81 to R 85 each independently represent 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, or a non-aromatic heterocyclic group, and optionally have a substituent; two adjacent groups of R 81 to R 85 may bond to each other to form a ring; R 81 ═R 85 is incompatible with R 82 ═R 84 ;
* represents a bonding site to a metal atom;

where R 6a1 and R 6a2 each independently represent 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 aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group, and optionally have a substituent; q represents an integer of 0 to 4;
R 6b1 , R 6c1 , R 6b2 , R 6c2 , and R 6d2 each independently represent a hydrogen atom, an alkyl group, an aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group, and optionally have a substituent; X 6a and X 6b each independently represent ═C(R 6e )— or ═N—; R 6e represents an alkyl group, an aromatic hydrocarbon ring, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring, or a non-aromatic heterocyclic group;
Ar 61 and Ar 62 are the same as Ar 51 and Ar 52 in Formulae (2) and (3), and each represent an aromatic hydrocarbon group represented by Formula (4); and
* represents a bonding site to a metal atom.

7 . The organic electroluminescent metal complex composition according to claim 4 , wherein M represents an iridium atom.

8 . An organic electroluminescent element including a pair of electrodes, and one or more organic layers disposed between the pair of electrodes, wherein one of the organic layers contains the organic electroluminescent metal complex composition according to claim 3 .

9 . The organic electroluminescent element according to claim 8 , wherein the one organic layer contains a mixture of the organic electroluminescent metal complex composition and a host compound having a freely rotating biaryl structure.

10 . The organic electroluminescent element according to claim 9 , wherein the host compound having a freely rotating biaryl structure has a dibenzofuran structure.

11 . The organic electroluminescent element according to claim 9 , wherein the host compound having a freely rotating biaryl structure has a carbazole structure.

12 . The organic electroluminescent element according to claim 9 , wherein the host compound having a freely rotating biaryl structure has an unsubstituted phenyl group.

13 . An illuminator including the organic electroluminescent element according to claim 8 .

14 . A display including the organic electroluminescent element according to claim 8 .

Assignees

• Konica Minolta Inc

Inventors

• Sugino Motoaki
• Kita Hiroshi

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title