Heteroleptic transition metal-carbene complexes and their use in organic light-emitting diodes (OLEDS)

Patent metadata

Field	Value
Publication number	US-10385263-B2
Application number	US-29611207-A
Country	US
Kind code	B2
Filing date	Apr 3, 2007
Priority date	Apr 5, 2006
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

The present invention relates to heteroleptic carbene complexes comprising at least two different carbene ligands, to a process for preparing the heteroleptic carbene complexes, to the use of the heteroleptic carbene complexes in organic light-emitting diodes, to organic light-emitting diodes comprising at least one inventive heteroleptic carbene complex, to a light-emitting layer comprising at least one inventive heteroleptic carbene complex, to organic light-emitting diodes comprising at least one inventive light-emitting layer, and to devices which comprise at least one inventive organic light-emitting diode.

First claim

The invention claimed is:

1. A heteroleptic carbene complex of the general formula (Ii) comprising two different carbene ligands (IIa) and (IIb),

wherein the ligand (IIa)

is

and
wherein, in the carbene ligand (IIb)

Do 1 is a donor atom selected from the group consisting of C, P, N and Si;
Do 2 is a donor atom selected from the group consisting of C, N, P, O and S;
r is 2 when Do 1 is C or Si, is 1 when Do 1 is N or P;
s is 2 when Do 2 is C, 1 when Do 2 is N or P, and are each 0 when Do 2 is O or S;
X is a spacer selected from the group consisting of silylene, alkylene, arylene, heteroarylene, alkynylene, alkenylene, NR 13 , PR 14 , BR 15 , O, S, SO, SO 2 , CO, CO—O, O—CO and (CR 16 R 17 ) w , where one or more nonadjacent (CR 16 R 17 ) groups may be replaced by NR 13 , PR 14 , BR 15 , O, S, SO, SO 2 , CO, CO—O, or O—CO;
w is from 2 to 10;
R 13 , R 14 , R 15 , R 16 , and R 17 are each independently selected from the group consisting of H, alkyl, aryl, heteroaryl, alkenyl, and alkynyl;
p is 0 or 1;
q is 0 or 1;
p′ is 0;
q′ is 0;
Y 1 and Y 2 are each independently hydrogen, a carbon group selected from the group consisting of alkyl, aryl, heteroaryl, alkynyl and alkenyl groups, or together form a bridge between the donor atom Do 1 and the nitrogen atom N which has at least two atoms, of which at least one is a carbon atom;
R 1 and R 2 are each independently hydrogen, an alkyl, an aryl, a heteroaryl, an alkynyl, an alkenyl, or R 1 and R 2 together form a bridge having a total of from three to five atoms, of which 1 to 5 atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group

forms a five- to seven-membered ring which optionally—in addition to the double bond already present—may have one further double bond or—in the case of a six- or seven-membered ring—two further double bonds, and may optionally be substituted by alkyl or aryl groups and/or groups with donor or acceptor action, and may optionally comprise at least one heteroatom, and the five- to seven-membered ring may optionally be fused to one or more further rings;
Y 1 and R 1 or Y 2 and R 1′ may be bonded to one another via a bridge where the bridge is a group selected from the group consisting of alkylene, arylene, heteroarylene, alkynylene, alkenylene, NR 18 , PR 19 , BR 20 , O, S, SO, SO 2 , SiR 30 R 31 , CO, CO—O, O—CO and (CR 21 R 22 ) x , where one or more nonadjacent (CR 21 R 22 ) groups may be replaced by NR 18 , PR 19 , BR 20 , O, S, SO, SO 2 , SiR 30 R 31 , CO, CO—O, or O—CO, where
x is from 2 to 10, and
R 18 , R 19 , R 20 , R 21 , R 22 , R 30 and R 31 are each independently selected from the group consisting of H, alkyl, aryl, heteroaryl, alkenyl, and alkynyl;
R 3 is selected from the group consisting of hydrogen, an alkyl, aryl, heteroaryl, alkynyl and alkenyl radical;
Y 3 is a hydrogen, an alkyl, alkynyl, or alkenyl radical; and

in the carbene ligand (IIb) has the structure

wherein one occurrence of Z′ in an o-position relative to the bonding site with Do 1 is CH, the other occurrence of Z′ in an o-position relative to the bonding site with Do 1 is CR 12′ , each occurrence of Z′ in an m- or p-position relative to the bonding site with Do 1 is independently CR 12′ or N, provided 0 or only 1 Z′ is N, and
R 12′ in the Z′ groups are each independently selected from the group consisting of H, an alkyl, aryl, heteroaryl, alkynyl, alkenyl radical and a radical with donor or acceptor action, where 2 R 12′ radicals optionally form a fused ring, wherein the fused ring may optionally comprise at least one heteroatom;
wherein, the aromatic base of the structure

or one of the R 12′ radicals is optionally bonded to Y 2 via a bridge,
wherein the bridge is selected from the group consisting of alkylene, arylene, heteroarylene, alkynylene, alkenylene, NR 18 , PR 19 , BR 20 , O, S, SO, SO 2 , SiR 30 R 31 , CO, CO—O, O—CO and (CR 21 R 22 ) x , where one or more nonadjacent (CR 21 R 22 ) groups may be replaced by NR 18 , PR 19 , BR 20 , O, S, SO, SO 2 , SiR 30 R 31 , CO, CO—O, or O—CO, where
x is from 2 to 10, and
R 18 , R 19 , R 20 , R 21 , R 22 , R 30 , R 31 are each independently selected from the group consisting of H, alkyl, aryl, heteroaryl, alkenyl, and alkynyl.

2. An organic light-emitting diode comprising at least one heteroleptic carbene complex according to claim 1 .

3. A device selected from the group consisting of stationary visual display units and mobile visual display units comprising at least one organic light-emitting diode according to claim 2 .

4. A light-emitting layer comprising at least one heteroleptic carbene complex according to claim 1 .

5. An organic light-emitting diode comprising an anode and a cathode and at least one light-emitting layer according to claim 4 between the anode and the cathode.

6. A device selected from the group consisting of stationary visual display units and mobile visual display units comprising at least one organic light-emitting diode according to claim 5 .

7. The organic light-emitting diode according to claim 5 , wherein the organic light-emitting diode further comprises a hole transporting layer between the anode and the light-emitting layer, wherein the hole transporting layer comprises a carbene complex.

8. The organic light-emitting diode according to claim 7 , wherein the carbene complex is a homoleptic carbene complex.

9. An organic light-emitting diode comprising an anode and a cathode and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises

and at least one heteroleptic carbene complex of the general formula (Ii) comprising two different carbene ligands (IIa) and (IIb),

wherein, in the ligand (IIa)

Do 1 is a donor atom selected from the group consisting of C, P, N, O, S and Si;
Do 2 is a donor atom selected from the group consisting of C, N, P, O and S;
r is 2 when Do 1 is C or Si, is 1 when Do 1 is N or P, and is 0 when Do 1 is O or S;
s is 2 when Do 2 is C, 1 when Do 2 is N or P, and is 0 when Do 2 is O or S;
X is a spacer selected from the group consisting of silylene, alkylene, arylene, heteroarylene, alkynylene, alkenylene, NR 13 , PR 14 , BR 15 , O, S, SO, SO 2 , CO, CO—O, O—CO and (CR 16 R 17 ) w , where one or more nonadjacent (CR 16 R 17 ) groups may be replaced by NR 13 , PR 14 , BR 15 , O, S,

Assignees

• Fuchs Evelyn
• Egen Martina
• Kahle Klaus
• Lennartz Christian
• Molt Oliver
• Nord Simon
• Kowalsky Wolfgang
• Schildknecht Christian
• Johannes Hans Hermann
• Udc Ireland Ltd

Inventors

• Fuchs Evelyn
• Egen Martina
• Kahle Klaus
• Lennartz Christian
• Molt Oliver
• Nord Simon
• Kowalsky Wolfgang
• Schildknecht Christian
• Johannes Hans-Hermann

Classifications

• H05B33/14

  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 title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title