Metal complexes

Patent metadata

Field	Value
Publication number	US-10700295-B2
Application number	US-201615760037-A
Country	US
Kind code	B2
Filing date	Sep 9, 2016
Priority date	Sep 14, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The present invention provides complexes of the formula (L)M(X), in which M is a metal atom selected from copper, silver and gold; L is a carbene ligand; and X is a monoanionic ligand. The complexes are useful as light emitters in the emissive zone of light-emitting devices such as OLEDs. The present invention also provides organometallic complexes which exhibit RASI photoemission, and the use of the same in light-emitting devices such as OLEDs.

First claim

The invention claimed is:

1. A complex of the following Formula I:
(L)M(X),  (I)

in which
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic amide ligand having the formula
R′—N—R″ or N

in which R′ and R″ are selected from hydrogen and organic groups, which when both organic groups may be the same or different;
and represents a cyclic organic group which may contain one or more rings;
excluding the compound Ad L-Au-NTf 2 in which Ad L is

and Tf is CF 3 —SO 2 —.

2. A complex according to claim 1 , wherein the complex has a neutral overall charge.

3. A complex according to claim 1 , wherein the CAAC ligand L is selected from:
A. a compound of Formula IIIa:

wherein R a , R b , R c and R d are CH 3 groups, and Ar represents a substituted phenyl group;

B. a compound of Formula IIIb:

wherein R a and R b are CH 3 groups and Ar represents a substituted phenyl group; and

C. the following group of compounds:

where R n represents a variable number n of 1-4 substituents, each of which is independently selected from the group comprising hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amino, aryl and heteroaryl.

4. A complex according to claim 1 , wherein the ligand X is selected from: arylamide and diarylamide; carbazolate; di-tert-butylcarbazolate; phenazine; N-methylphenazine; phenothiazine; 3,7-dinitrophenothiazine; acridone; dibenzazepine; and 10,11-dihydrodibenzazepine.

5. A complex according to claim 1 , wherein the ligand X is selected from NHPh and NH(3,5-bis(trifluoromethyl)phenyl), NPh 2 , where Ph=phenyl; carbazolate; 3,6-di-tert-butylcarbazolate; phenazine; N-methylphenazine; phenothiazine; 3,7-dinitrophenothiazine; acridone; dibenzazepine; and 10,11-dihydrodibenzazepine.

6. A light-emitting device comprising an emissive zone capable of emitting light in response to introduced energy, wherein the emissive zone capable of emitting light comprises at least one organometallic complex of Formula I:
(L)M(X),  (I)

in which
A.
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic amide ligand having the formula
R′—N—R″ or N

in which R′ and R″ are selected from hydrogen and organic groups, which when both organic groups may be the same or different;
and represents a cyclic organic group which may contain one or more rings;
B.
M is a metal atom selected from copper and silver;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic ligand;
C.
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic amide ligand having the formula
R′—N—R″ or N

in which R′ and R″ are selected from hydrogen and organic groups, which when both organic groups may be the same or different;
and represents a cyclic organic group which may contain one or more rings;
wherein in both options B and C the ligand L is a cyclic compound of Formula III:

in which
R′ is selected from an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;
d=e=f=1 and g=0 so that G has no meaning;
D=>CR d R d , where R d =methyl;
E=>CH 2 ; and
F is >CR f R ff , in which wherein R f and R ff together with the carbon atom C to which they are linked form an unsubstituted adamantylidene group;
D.
M is a metal atom selected from copper and silver;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic ligand which is a compound of Formula IV
[E-Ar] −   (IV)

wherein Ar is an optionally substituted aryl or optionally substituted heteroaryl group, and
E- is selected from C(R 1 )(R 2 )—, O—, S—, Se—, Te—, N(R)—, P(R)—, As(R)— and Sb(R)—,
in which R, R 1 and R 2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted allyl, optionally substituted aryl and optionally substituted heteroaryl; and R, R 1 and R 2 groups, when present, may optionally be directly linked to the Ar moiety by one or more linker species as well as via the said C, N, P, As or Sb atom
E.
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic ligand which is a compound of Formula IV
[E-Ar] −   (IV)

wherein Ar is an optionally substituted aryl or optionally substituted heteroaryl group, and
E- is N(R)—, in which R is chosen from hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted allyl, optionally substituted aryl and optionally substituted heteroaryl; and an R group may optionally be directly linked to the Ar moiety by one or more linker species as well as via the said N atom; and
excluding the compound Ad L-Au-NTf 2 in which Ad L is

and Tf is CF 3 —SO 2 —.

7. A method of preparing complexes of Formula I:
(L)M(X),  (I)

in which
A.
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic amide ligand having the formula
R′—N—R″ or N

in which R′ and R″ are selected from hydrogen and organic groups, which when both organic groups may be the same or different;
and represents a cyclic organic group which may contain one or more rings;
B.
M is a copper atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic ligand;
C.
M is a gold atom;
L is a cyclic alkyl amino carbene (CAAC) ligand having a saturated cyclic structure in which the atoms of the ring which includes the carbene site consist of carbon atoms and one nitrogen atom; and
X is a monoanionic amide ligand having the formula
R′—N—R″ or N

in which R′ and R″ are selected from hyd

Assignees

• Uea Enterprises Ltd
• Cambridge Entpr Ltd

Inventors

• Bochmann Manfred
• Romanov Alexander Sergeyevich
• Credgington Daniel John Nicholas
• Di Dawei
• Yang Le

Classifications

• H10K85/371 Primary

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K2101/10

  Triplet emission · CPC title

• C07F1/08 Primary

  Copper compounds · CPC title

• C07F1/12

  Gold compounds · CPC title