Transition metal complexes with carbene ligands and the use thereof in OLEDs
The present invention relates to iridium and platinum carbene complexes of the general formula (I), to OLEDs (Organic Light-Emitting Diodes) which comprise such complexes, to a device selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a metal-carbene complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge or exciton blocker.
1. A metal-carbene complex of the general formula
wherein
M is Ir or Pt,
R 1 and R 2 are independently of each other a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 ring atoms,
A 1 , A 2 , A 3 and A 4 are independently from each other CR 3 or N;
each R 3 is independently of each other H, a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 ring atoms; or a group with donor or acceptor action;
K and L are independently from each other a bidentate monoanionic ligand;
for M is Ir, o is 1, 2 or 3, m is 0, 1, or 2, n is 0, 1, or 2 and m+n+o=3 and
for M is Pt, o is 1, or 2, m is 0, or 1, n is 0, or 1 and m+n+o=2.
2. The metal-carbene complex according to claim 1 , which is a metal-carbene complex of the general formula
wherein
A 1 is N, or CR 4 ,
R 4 , R 5 , R 6 and R 7 are independently of each other H, a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 18 ring atoms; or a group with donor or acceptor action and
R 1 , R 2 , M, L, n, m and o are as defined in claim 1 .
3. The metal complex according to claim 2 , which is a metal-carbene complex of the general formula
wherein
K is a bidentate monoanionic ligand of formula
in which R 74 and R 74′ are in each case independently a linear or branched alkyl radical having 1 to 6 carbons atoms optionally bearing at least one functional group; substituted or unsubstituted cycloalkyl radical having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 20 carbon atoms; substituted or unsubstituted heteroaryl radical having a total of 5 to 18 ring atoms, and
R 75 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 20 carbon atoms;
A 1 is N, or CR 4 ,
R 4 , R 5 , R 6 and R 7 are independently of each other H, a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 12 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 15 ring atoms; or a group with donor or acceptor action, selected from halogen radicals, SiMe 3 , SiPh 3 , OMe, NO 2 , CN, NCO, NCS, CF 3 , and
R 1 and R 2 are independently of each other a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally beating at least one functional group and having 3 to 12 carbon atoms, substituted or unsubstituted aryl radical, optionally bearing at least one functional group and having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 15 carbon atoms.
4. The metal complex according to claim 2 , which is a metal-carbene complex of the general formula
wherein
o is 1, 2, or 3,
L is a bidentate monoanionic ligand of formula
in which R 74 and R 74′ are in each case independently a linear or branched alkyl radical having 1 to 6 carbons atoms optionally bearing at least one functional group; substituted or unsubstituted cycloalkyl radical having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 20 carbon atoms; substituted or unsubstituted heteroaryl radical having a total of 5 to 18 ring atoms, and
R 75 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 20 carbon atoms; or
L is a bidentate monoanionic ligand of formula
A 1 is N, or CR 4 ,
R 4 , R 5 , R 6 and R 7 are independently of each other H, a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 12 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 15 ring atoms; or a group with donor or acceptor action, selected from halogen radicals, SiMe 3 , SiPh 3 , OMe, NO 2 , CN, NCO, NCS, CF 3 , and
R 1 and R 2 are independently of each other a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally beating at least one functional group and having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 12 carbon atoms, substituted or unsubstituted aryl radical, optionally bearing at least one functional group and having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having a total of 5 to 15 ring atoms.
5. The metal complex according to claim 4 , which is a metal-carbene complex of the general formula
wherein
R 1 , R 2 , R 5 , R 6 , R 7 , and A 1 are as defined in claim 4 .
6. The metal complex according to claim 2 , wherein R 7 is hydrogen.
7. The metal complex according to claim 2 , wherein
A 1 is CR 4 , wherein R 4 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 15 carbon atoms, or a group with donor or acceptor action selected from CN, CF 3 , SiMe 3 , halogen radicals.
8. The metal complex according to claim 2 , wherein
R 5 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 15 carbon atoms, or a group with donor or acceptor action selected from CN, CF 3 , SiMe 3 , halogen radicals.
9. The metal complex according to claim 2 , wherein
R 6 is hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 15 carbon atoms, or a group with donor or acceptor action selected from CN, CF 3 , SiMe 3 , halogen radicals.
10. The metal-carbene complex according to claim 1 , wherein
R 1 is a linear or branched alkyl radical having 1 to 6 carbon atoms, a substituted or unsubstituted aryl radical having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl radical having a total of 5 to 18 ring atoms.
11. The metal-carbene complex according to claim 1 , wherein
R 2 is a linear or branched alkyl radical having 1 to 6 carbons atoms, or a unsubstituted aryl radical having 6 to 15 carbon atoms.
12. The metal-carbene complex according to claim 1 , which is a compound of formula
Compound
R 1
R 2
R 6
EM-1
CH 3
H
EM-2
CH 3
H
EM-3
CH(CH 3 ) 2
H
EM-4
CH(CH 3 ) 2
H
EM-5
CH(CH 3 ) 2
H
EM-6
CH(CH 3 ) 2
H
EM-7
CH(CH 3 ) 2
H
EM-8
CH(CH 3 ) 2
H
EM-9
CH 3
H
EM-10
CH 3
H
EM-11
CH 3
H
EM-12
CH 3
H
EM-13
H
EM-14
H
EM-15
H
EM-16
H
EM-17
H
EM-18
H
EM-19
CH(CH 3 ) 2
F
EM-20
CH(CH 3 ) 2
F
EM-21
CH(CH 3 ) 2
F
EM-22
CH(CH 3 ) 2
F
EM-23
CH(CH 3 ) 2
F
EM-24
CH(CH 3 ) 2
F
EM-25
CH 3
F
EM-26
CH 3
F
EM-27
CH 3
F
EM-28
CH 3
F
EM-29
CH 3
F
EM-30
CH 3
F
EM-31
F
EM-32
F
EM-33
F
EM-34
F
EM-35
F
EM-36
F
EM-37
CH(CH 3 ) 2
CF 3
EM-38
CH(CH 3 ) 2
CF 3
EM-39
CH(CH 3 ) 2
CF 3
EM-40
CH(CH 3 ) 2
CF 3
EM-41
CH(CH 3 ) 2
CF 3
EM-42
CH(CH 3 ) 2
CF 3
EM-43
CH 3
CF 3
EM-44
CH 3
CF 3
EM-45
CH 3
CF 3
EM-46
CH 3
CF 3
EM-47
CH 3
CF 3
EM-48
CH 3
CF 3
EM-49
CF 3
EM-50
CF 3
EM-51
CF 3
EM-52
CF 3
EM-53
CF 3
EM-54
CF 3 .
13. An organic electronic device, comprising at least one metal-carbene complex according to claim 1 .
14. The organic electronic device according to claim 13 , wherein the organic electronic device is selected from organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic field-effect transistors (OFETs) and light-emitting electrochemical cells (LEECs).
15. A light-emitting layer comprising at least one metal-carbene complex according to claim 1 .
16. The light-emitting layer according to claim 15 , further comprising a host material.
17. An apparatus selected from the group consisting of stationary visual display units, illuminations, information panels, and mobile visual display units, illumination units; keyboards; items of clothing; furniture and wallpaper, comprising the organic electronic device according to claim 13 .
18. A method of using the metal-carbene complex according to claim 1 , comprising:
adding the metal-carbene complex to electrophotographic photoreceptors, photoelectric converters, organic solar cells (organic photovoltaics), switching elements, organic light emitting field effect transistors (OLEFETs), image sensors, dye lasers and electroluminescent devices.
19. A process for preparing a metal-carbene complex according to claim 1 by contacting a suitable compound comprising M with a compound of the general formula
wherein
A 1 , A 2 , A 3 , A 4 , R 1 , R 2 and M are as defined in claim 1 , and
X is F, CA, Br, I, PF 6 , or BF 4 .
20. An apparatus selected from the group consisting of stationary visual display units, illuminations, information panels, and mobile visual display units, illumination units; keyboards; items of clothing; furniture and wallpaper, comprising the light-emitting layer according to claim 15 .