Transition metal complexes comprising carbene ligands serving as emitters for organic light-emitting diodes (OLED's)

Patent metadata

Field	Value
Publication number	US-9748498-B2
Application number	US-90161010-A
Country	US
Kind code	B2
Filing date	Oct 11, 2010
Priority date	Aug 19, 2003
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

Use of transition metal complexes of the formula (I) in organic light-emitting diodes

where:
M 1 is a metal atom;
carbene is a carbene ligand;
L is a monoanionic or dianionic ligand;
K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a π complex with M 1 ;
n is the number of carbene ligands and is at least 1;
m is the number of ligands L, where m can be 0 or ≧1;
o is the number of ligands K, where o can be 0 or ≧1;
where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also

an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific transition metal complexes comprising at least two carbene ligands.

First claim

We claim:

1. An organic light-emitting diode comprising at least one uncharged transition metal complexes of the formula (IB)

wherein the symbols have the following meanings:
M 1 is a metal atom selected from the group consisting of Rh, Nb, Pd, Pt, Fe, Ru, Os, Mo, W, Mn, Tc, Re, Ag and Au in any oxidation state possible for the respective metal atom;
L is a monoanionic or dianionic ligand, which may be monodentate or bidentate;
K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; phosphonates and derivatives thereof, arsenates and derivatives thereof; phosphites; CO; pyridines; nitriles and conjugated dienes which form a π complex with M 1 ;
n is the number of carbene ligands, wherein n is at least 1 and when n>1 the carbene ligands in the complex of the formula IB can be identical or different;
m is the number of ligands L, wherein m can be 0 or ≧1 and when m>1 the ligands L can be identical or different;
o is the number of ligands K, wherein o can be 0 or ≧1 and when o>1 the ligands K can be identical or different;
wherein the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1,
Do 1 is a donor atom selected from the group consisting of C, P, N, O and S;
r is 2 when Do 1 is C, is 1 when Do 1 is N or P and is 0 when Do 1 is O or S;
p is 0;
q is 0;
Y 1 and Y 2 together form a bridge between the donor atom Do 1 and the nitrogen atom N which has two atoms of which one is a carbon atom, and the other is a carbon or nitrogen atom,
Y 3 is hydrogen or an alkyl, aryl, heteroaryl or alkenyl radical; or

where Do 2 ′, q′, s′, R 3 ′, R 1 ′, R 2 ′, X′ and p′ are each, independently of one another, as defined for Do 2 , q, s, R 3 , R 1 , R 2 , X and p; and
R 1 and R 2 together form a bridge having a total of from three to five atoms of which one or two atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group

forms a five- to seven-membered, ring which may contain, in addition to the existing double bond, one further double bond or in the case of a six- or seven-membered ring two further double bonds and may be substituted by alkyl or aryl groups and may contain at least one heteroatom.

2. The organic light-emitting diode as claimed in claim 1 , wherein the uncharged transition metal complexes are employed as emitter molecules.

3. The organic light-emitting diode as claimed in claim 1 , wherein the carbene ligand or ligands is/are monoanionic.

4. The organic light-emitting diode as claimed in claim 1 , wherein the group

is selected from the group consisting of

wherein the symbols have the following meanings:
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 are each hydrogen, alkyl, aryl, heteroaryl or alkenyl or a substituent which acts as a donor or acceptor;
R 10 is alkyl, aryl, heteroaryl or alkenyl or 2 radicals R 10 together form a fused-on ring, or R 10 is a radical which acts as a donor or acceptor;
v is from 0 to 4 and when v is 0 the four carbon atoms of the aryl radical in the formula c which may be substituted by R 10 bear hydrogen atoms;
Y 3 is a hydrogen atom or an alkyl, aryl, heteroaryl or alkenyl radical; or

wherein Do 2 ′, q′, s′, R 3 ′, R 1 ′, R 2 ′, X′ and p′ are defined, independently of one another, as for Do 2 , q, s, R 3 , R 1 , R 2 , X and p.

5. The organic light-emitting diode as claimed in claim 1 , wherein the group

denotes the structure

wherein the symbols have the following meanings:
Z is CH or N and can be located in the o, m or p position relative to the point of linkage of the group to the carbene ligand;
R 12 is an alkyl, aryl, heteroaryl or alkenyl radical, or 2 radicals R 12 together form a fused-on ring which may contain one or more heteroatoms, or R 12 is a radical which acts as a donor or acceptor; and
t is 0 to 3 and when t>1 the radicals R 12 can be identical or different.

6. The organic light-emitting diode as claimed in claim 1 , wherein the following portion II of formula IB:

wherein the symbols have the following meanings:
Z, Z′ are identical or different and are each CH or N;
R 12 , R 12 ′ are identical or different and are each an alkyl, aryl, heteroaryl or alkenyl radical, or 2 radicals R 12 or R 12 ′ together form a fused-on ring which may contain at least one heteroatom, or R 12 or R 12 ′ is a radical which acts as a donor or acceptor;
t and t′ are identical or different and are each from 0 to 3, and when t or t′>1 the radicals R 12 or R 12 ′ can be identical or different;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 are each hydrogen, alkyl, aryl, heteroaryl or alkenyl or a radical which acts as a donor or acceptor;
R 10 is alkyl, aryl, heteroaryl or alkenyl or 2 radicals R 10 together form a fused-on ring which may contain at least one heteroatom, or R 10 is a radical which acts as a donor or acceptor; and
v is from 0 to 4 and when v is 0 the four carbon atoms of the aryl radical in the formula c which may be substituted by R 10 bear hydrogen atoms.

7. An uncharged transition metal complex of the formula IC

wherein the symbols have the following meanings:
M 1 is Ru, Rh, Pt in any oxidation state possible for the respective metal atom;
L is a monoanionic or dianionic ligand, which may be monodentate or bidentate;
K is an uncharged monodentate or bidentate ligand;
n is the number of carbene ligands, wherein n is at least 2 and the carbene ligands in the transition metal complex can be identical or different;
m is the number of ligands L, wherein m can be 0 or ≧1 and when m>1 the ligands L can be identical or different;
o is the number of ligands K, wherein o can be 0 or ≧1 and in the case of o>1 the ligands K can be identical or different;
wherein the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom used and the denticity of the ligands and also on the charge on the ligands, with the proviso that n is at least 2;
p is 0;
q is 0;
Y 3 is hydrogen or an alkyl, aryl, heteroaryl or alkenyl radical; or

wherein Do 2 ′, q′, s′, R 3 ′, R 1 ′, R 2 ′, X′ and p′ are each, independently of one ano

Assignees

• Bold Markus
• Lennartz Christian
• Prinz Martina
• Schmidt Hans-Werner
• Thelakkat Mukundan
• Baete Markus
• Neuber Christian
• Kowalsky Wolfgang
• Schildknecht Christian
• Johannes Hans-Hermann
• Udc Ireland Ltd

Inventors

• Bold Markus
• Lennartz Christian
• Prinz Martina
• Schmidt Hans-Werner
• Thelakkat Mukundan
• Baete Markus
• Neuber Christian
• Kowalsky Wolfgang
• Schildknecht Christian
• Johannes Hans-Hermann

Classifications

• B01J2531/827

  Iridium · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• B01J2531/16

  Copper · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F15/0033

  Iridium compounds · CPC title