# US 11,444,254 B2 · Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs

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- Number: US 11,444,254 B2
- Document ID: US11444254B2
- Status: Granted
- Kind: B2
- Application number: 17/132,829
- Filed: 2020-12-23
- Published: 2021-04-29
- Granted: 2022-09-13
- Earliest claimed: 2009-12-14
- Assignees: UDC Ireland Limited
- Applicants: Udc Ireland Limited
- Inventors: Oliver Molt; Nicolle Langer; Evelyn Fuchs; Korinna Dormann; Christian Schildknecht; Soichi Watanabe; Gerhard Wagenblast; Christian Lennartz; Thomas Schaefer; Heinz Wolleb; Teresa Marina Figueira Duarte; Stefan Metz; Peter Murer
- Web page: https://patentgrep.com/patent/US11444254B2

## CPC

- C07F 15/0086: {Platinum compounds}
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 405/14: containing three or more hetero rings
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/30: Coordination compounds
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 50/14: Carrier transporting layers
- H10K 50/155: comprising dopants
- H10K 50/16: Electron transporting layers
- H10K 50/165: comprising dopants
- H10K 50/18: Carrier blocking layers
- H10K 85/653: {comprising only oxygen as heteroatom}
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to metal-carbene complexes comprising a central atom selected from iridium and platinum, and diazabenzimidazolocarbene ligands, to organic light diodes which comprise such complexes, to light-emitting layers comprising at least one such metal-carbene complex, to a device selected from the group comprising illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED and 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.

## Claims

### Claim 1

A metal-carbene complex of the general formula (I):
wherein:
M is Ir or Pt,
n is an integer selected from 1, 2 and 3,
Y is NR1, O, S or C(R10)2,
A2, A3, A4, A5 are each independently N or C, where 2 A=nitrogen atoms and at least one carbon atom is present between two nitrogen atoms in the ring,
R1 is 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, 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 carbon atoms and/or heteroatoms,
R2, R3, R4, R5 are each, if A2, A3, A4 and/or A5 is N, a free electron pair, or, if A2, A3, A4 and/or A5 is C, each independently hydrogen, 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, 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or
R3 and R4 together with A3 and A4 form an optionally substituted, unsaturated ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, wherein R3 and R4 together with A3 and A4 do not form a phenyl ring,
R6, R7, R8, R9 are each independently hydrogen, 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or
R6 and R7, R7 and R8 or R8 and R9, together with the carbon atoms to which they are bonded, form a saturated, unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,
and/or
if A5 is C, R5 and R6 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, an aromatic unit, heteroaromatic unit and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which is optionally fused a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms,
R10 is independently 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, 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 carbon atoms and/or heteroatoms,
K is an uncharged mono- or bidentate ligand,
L is a mono- or dianionic ligand,
m is 0, 1 or 2, where, when m is 2, the K ligands may be the same or different, and
o is 0, 1 or 2, where, when o is 2, the L ligands may be the same or different.

### Claim 2 (depends on 1)

The metal-carbene complex according to claim 1, wherein:
M is Ir,
n is 1, 2 or 3,
Y is NR1,
A2, A3, A4, A5 are each independently N or C, where 2 A=nitrogen atoms and at least one carbon atom is present between two nitrogen atoms in the ring,
R1 is a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms,
R2, R3, R4, R5 are each, if A2, A3, A4 and/or A5 is N, a free electron pair, or, if A2, A3, A4 and/or A5 is C, each independently hydrogen, linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical having a total of 5 to 18 carbon atoms and/or heteroatoms,
or
R3 and R4 together with A3 and A4 form an optionally substituted, unsaturated ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, wherein R3 and R4 together with A3 and A4 do not form a phenyl ring,
R6, R7, R8, are each independently hydrogen, 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 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 carbon atoms and/or heteroatoms,
L is a monoanionic bidentate ligand,
m is 0, and
o is 0, 1 or 2.

### Claim 3 (depends on 1)

The metal-carbene complex according to claim 1, wherein:
M is Ir,
n is 2 or 3,
Y is NR1,
A2 and A5 are each N and A3 and A4 are each C
or
A2 and A4 are each N and A3 and A5 are each C
or
A3 and A5 are each N and A2 and A4 are each C,
R1 is a linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted phenyl radical, substituted or unsubstituted heteroaryl radical having a total of 6 to 18 carbon atoms and/or heteroatoms,
R2, R3, R4, R5 are each, if A2, A3, A4 and/or A5 is N, a free electron pair or, if A2, A3, A4 and/or A5 is C, each independently hydrogen, linear or branched alkyl radical having 1 to 6 carbon atoms, substituted or unsubstituted phenyl radical,
R3 and R4 together with A3 and A4 form an optionally substituted, monounsaturated ring having a total of 5 to 7 carbon atoms,
R6, R7, R8, R9 are each independently hydrogen, linear or branched alkyl radical having 1 to 20 carbon atoms, o,o′-dialkylated aryl radical having 6 to 30 carbon atoms,
L is a monoanionic bidentate ligand,
m is 0, and
o is 0 or 1.

### Claim 4 (depends on 1)

The metal-carbene complex of claim 1, wherein, in the general formula (I), L is a carbene ligand of the general formula (II):
wherein:
A6, A7 are each independently C or N,
R11 is 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms,
R12, R13 are each independently, when A is N, a free electron pair, or, when A is C, hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carton atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
R14, R15, R16, R17 are each independently hydrogen, 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carton atoms and/or heteroatoms, group with donor or acceptor action,
or
R12 and R13, R14 and R15, R15 and R16 or R16 and R17 form, together with A or the carbon atoms to which they are bonded, an unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,
and/or
if A6 is C, R13 and R14 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which is optionally fused a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms.

### Claim 5 (depends on 1)

The metal-carbene complex of claim 1, wherein L in the general formula (I) is a heterocyclic noncarbene ligand of the general formula (III):
wherein:
D are each independently CR18 or N;
W is C, N;
E are each independently CR19, N, or NR20;
G is CR21, N, NR22, S, or O;
R18, R19, R21 are each independently hydrogen, 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or in each case two R18, R19 and R21 radicals, together with the carbon atoms to which they are bonded, form a saturated, unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,
R20, R22 are each independently 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
the solid curved line is an optional bridge between one of the D groups and the G group, and the optional bridge is selected from the group consisting of alkylene, arylene, heteroarylene, alkynylene, alkenylene, NR23, O, S, SiR24R25 and (CR25R27)d, where one or more nonadjacent (CR26R27) groups may be replaced by NR23, O, SiR24R25, where
d is 2 to 10;
and
R24, R25, R26, R27 independently represent H, alkyl, aryl, heteroaryl, alkenyl, or alkynyl.

### Claim 6 (depends on 1)

A process for preparing the metal-carbene of claim 1, the process comprising contacting at least one compound comprising M with at least one ligand or ligand precursor.

### Claim 7 (depends on 6)

The process according to claim 6, comprising contacting the at least one compound with at least one ligand precursor, wherein the ligand precursor is a Ag-carbene complex.

### Claim 8 (depends on 6)

The process according to claim 6, comprising contacting the at least one compound with at least one ligand precursor, wherein the ligand precursor is a compound of the general formula (IV):
wherein:
Y is NR1, O, S or C(R10)2,
A2, A3, A4, A5 are each independently N or C, where 2 A=nitrogen atoms and at least one carbon atom is present between two nitrogen atoms in the ring,
R2, R3, R4, R5 are each, if A2, A3, A4 and/or A5 is N, a free electron pair, or, if A2, A3, A4 and/or A5 is C, each independently hydrogen, 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, 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or
R3 and R4 together with A3 and A4 form an optionally substituted, unsaturated ring optionally interrupted by at least one further heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms, wherein R3 and R4 together with A3 and A4 do not form a phenyl ring,
R6, R7, R8, R9 are each independently hydrogen, 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, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, cycloheteroalkyl 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 carbon atoms and/or heteroatoms, group with donor or acceptor action,
or
R6 and R7, R7 and R8 or R8 and R9, together with the carbon atoms to which they are bonded, form a saturated, unsaturated or aromatic, optionally substituted ring optionally interrupted by at least one heteroatom and having a total of 5 to 18 carbon atoms and/or heteroatoms,
and/or
if A5 is C, R5 and R6 together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, an aromatic unit, heteroaromatic unit and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which is optionally fused a substituted or unsubstituted, five- to eight-membered ring comprising carbon atoms and/or heteroatoms,
R28 is independently SiR29R30R31, aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, and
R29, R30, R31 are each independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl.

### Claim 9 (depends on 1)

An organic electronic component, comprising at least one metal-carbene complex of claim 1.

### Claim 10 (depends on 9)

The organic electronic component according to claim 9, which is an organic light-emitting diode (OLED), organic photovoltaic cell (OPV), organic field-effect transistor (OFET) or light-emitting electrochemical cell (LEEC).

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 11)

An OLED comprising the light-emitting layer of claim 11.

### Claim 13 (depends on 1)

An OLED comprising at least one metal-carbene complex according to claim 1 and at least one compound of the formula (X):
wherein:
T is NR57, S, O or PR57;
R57 is aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl;
Q′ is —NR58R59, —P(O)R60R61, —PR62R63, —S(O)2R64, —S(O)R65, —SR66 or —OR67,
R55 and R56 are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, SiR70R71R72, a Q′ group or a group with donor or acceptor action;
a″ is 0, 1, 2, 3 or 4;
b′ is 0, 1, 2 or 3;
R58, R59 form, together with the nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action, and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, where the fused radicals may be unsubstituted or substituted by one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action;
R70, R71, R72, R60, R61, R62, R63, R64, R65,R66, R67 are each independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl,
or
two units of the general formula (X) are bridged to one another through a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom, through a bond or through O.

### Claim 14 (depends on 13)

The OLED according to claim 13, comprising at least one compound of the formula (XI) or (XI*):
wherein:
T is NR57, S, O or PR57;
R57 is aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl;
Q′ is —NR58R59, —P(O)R60R61, —PR62R63, —S(O)2R64, —S(O)R65, —SR66 or —OR67;
R70, R71, R72 are each independently aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, where at least one of the R70, R71, R72 radicals comprises at least two carbon atoms, or OR73,
R55, R56 are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a Q′ group or a group with donor or acceptor action;
a′, b′ for the compound of the formula (XI): are each independently 0, 1, 2, 3; for the compound of the formula (XI*), a′ is 0, 1, 2 and b′ is 0, 1, 2, 3, 4;
R58, R59 form, together with the nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, where the fused radicals may be unsubstituted or substituted by one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action;
R73 are each independently SiR74R75R76, aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, optionally substituted by an OR77 group,
R77 are each independently SiR74R75R78, aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl,
R60, R61, R62, R63, R64, R65, R66, R67, R74, R75, R76 are each independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl,
or
two units of the general formulae (XI) and/or (XI*) are bridged to one another through a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom or through O, where this bridge in the general formulae (XI) and/or (XI*) is in each case attached to the silicon atoms in place of R71.

### Claim 15 (depends on 14)

The OLED according to claim 14, wherein R70 and/or R71 and/or R72 in the compounds of the general formula (XI) or (XI*) are aromatic units of the general formulae (XIi) and/or (XIi*):
wherein:
T is NR57, S, O or PR57;
Q′ is —NR58R59, —P(O)R60R61, —PR62R63, —S(O)2R64, —S(O)R65, —SR66 or —OR67;
R55R56 are each independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a Q′ group or a group with donor or acceptor action; and
a′, b′ for the compound of the formula (XIi): are each independently 0, 1, 2, 3; for the compound of the formula (XIi*), a′ is 0, 1, 2 and b′ is 0, 1, 2, 3, 4.

### Claim 16 (depends on 11)

The light-emitting layer of claim 11, further at least one matrix material.

### Claim 17 (depends on 12)

The OLED according to claim 12, comprising an electron-transporting layer comprising at least two different materials, of which at least one material is electron-conducting.

### Claim 18 (depends on 17)

The OLED according to claim 17, wherein the electron-transporting layer comprises at least one phenanthroline derivative, at least one pyridine derivative, or at least one alkali metal hydroxyquinolate complex.

### Claim 19 (depends on 12)

A device comprising at least one OLED according to claim 12, wherein the device is at least one selected from the group consisting of a stationary visual display unit, a mobile visual display unit, and an illumination unit.

### Claim 20 (depends on 1)

An OLED comprising the metal-carbene complex according to claim 1, wherein the metal-carbene complex is at least one selected from the group consisting of an emitter, a matrix material, a charge transport material and a charge blocker.