Materials for organic electroluminescent devices
View Patent ↗The present invention relates to transition-metal complexes of the general formula I or II, in particular as emitter molecules in organic electronic devices, to a layer and to an electronic device which comprise the compounds according to the invention, and to a process for the preparation of the compounds according to the invention.
1. A compound of formula II
wherein
M is Pt 2+ ,
Ar is, identically or differently on each occurrence, an aromatic ring system having 5 to 10 aromatic ring atoms, which may be substituted by a plurality of radicals R,
Y is, identically or differently on each occurrence, C or N, with the proviso that always two C atoms are part of Ar and two N atoms are always bonded to the metal,
X is, identically or differently on each occurrence, a divalent group selected from
or combinations thereof, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms selected from
which is optionally substituted by one or more radicals R, or combinations thereof,
R is, identically or differently on each occurrence, N(Ar 1 ) 2 , CN, a straight-chain alkyl group having 1 to 3 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 1 is, identically or differently on each occurrence, H, D, CN, an alkyl group having 1 to 10 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 2 is, identically or differently on each occurrence, H, F, CN or an aliphatic aromatic and/or heteroaromatic hydrocarbon radical having 1 to 10 C atoms, where two or more substituents R 2 may also form a mono- or polycyclic aliphatic or aromatic ring system with one another, and
Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R,
n is on each occurrence, identically or differently, 0 or 1, where, for n=0, a hydrogen or a radical R or Ar is bonded instead of the X concerned.
2. A compound of formula II
wherein
M is Pt 2+ ,
Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may be substituted by a plurality of radicals R,
Y is, identically or differently on each occurrence, C or N, with the proviso that always either two C atoms and two N atoms are always bonded to the metal,
X is, identically or differently on each occurrence, a divalent group selected from
or combinations thereof, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, selected from
which is optionally substituted by one or more radicals R, or combinations thereof,
R is, identically or differently on each occurrence, N(Ar 1 ) 2 , CN, a straight-chain alkyl group having 1 to 3 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 1 is, identically or differently on each occurrence, H, D, CN, an alkyl group having 1 to 10 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 2 is, identically or differently on each occurrence, H, F, CN or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 10 C atoms, where two or more substituents R 2 may also form a mono- or polycyclic aliphatic or aromatic ring system with one another, and
Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R,
n is on each occurrence, identically or differently, 0 or 1, with the proviso that at least one n=1, and where, for n=0, a hydrogen or a radical R or Ar is bonded instead of the X concerned.
3. The compound of 2 , wherein the group Ar is selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine pyridazine, quinoline, isoquinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene and indole.
4. The compound of 2 , wherein said compound is a compound of formula IV:
wherein
Z is, identically or differently on each occurrence, CR or N.
5. The compound of claim 4 , wherein Z is CR.
6. An oligomer, polymer or dendrimer comprising one or more compounds of 2 , wherein one or more bonds are present from the compounds of the formula II to the polymer, oligomer or dendrimer.
7. A process for preparing the compound of claim 2 , comprising the step of reacting free ligand with a corresponding metal salt to give the complex.
8. A layer comprising at least one compound of 2 .
9. An organic electronic device comprising one or more compounds of 2.
10. The organic electronic device of claim 9 , wherein said organic electronic device is an organic electroluminescence device and the compound of formula II is employed as emitting compound in an emitting layer or as charge-transport compound in a charge-transport layer or charge injection layer.
11. The organic electronic device of claim 9 , wherein said organic electronic device is a organic electroluminescent device, a polymeric electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, or a organic laser diode.
12. A compound of formula I
wherein
M is Pt 2+ ,
Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may be substituted by a plurality of radicals R,
Y is, identically or differently on each occurrence, C or N, with the proviso that always either two C atoms and two N atoms are always bonded to the metal,
X is, identically or differently on each occurrence, a divalent group selected from
or combinations thereof, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, selected from
which is optionally substituted by one or more radicals R, or combinations thereof,
R is, identically or differently on each occurrence, N(Ar 1 ) 2 , CN, a straight-chain alkyl group having 1 to 3 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 1 is, identically or differently on each occurrence, H, D, CN, an alkyl group having 1 to 10 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ,
R 2 is, identically or differently on each occurrence, H, F, CN or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 10 C atoms, where two or more substituents R 2 may also form a mono- or polycyclic aliphatic or aromatic ring system with one another, and
Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R,
n is on each occurrence, identically or differently, 0 or 1, with the proviso that exactly one n=1, and where, for n=0, a hydrogen or a radical R or Ar is bonded instead of the X concerned.
13. The compound of 12 , wherein the group Ar is selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene and indole.
14. The compound of 12 , wherein said compound is a compound of formula III:
wherein
Z is identically or differently on each occurrence, CR or N.
15. The compound of claim 14 , wherein Z is CR.
16. An oligomer, polymer or dendrimer comprising one or more compounds of 12 , wherein one or more bonds are present from the compounds of the formula I to the polymer, oligomer or dendrimer.
17. A process for preparing the compound of claim 12 , comprising the step of reacting free ligand with a corresponding metal salt to give the complex.
18. A layer comprising at least one compound of 12 .
19. An organic electronic device comprising one or more compounds of 12 .
20. The organic electronic device of claim 19 , wherein said organic electronic device is an organic electroluminescence device and the compound of formula I is employed as emitting compound in an emitting layer or as charge-transport compound in a charge-transport layer or charge injection layer.
21. The organic electronic device of claim 19 , wherein said organic electronic device is a organic electroluminescent device, a polymeric electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, or a organic laser diode.