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US 8,710,284 B2Granted
Materials for organic electroluminescent devices containing substituted 10-benzo[c]phenanthrenes
AssigneeMerck Patent GmbH
InventorsAmir Hossain Parham, Arne Buesing, Holger Heil, Philipp Stoessel
Life of this patent
Estimating the term…
Abstract
The present invention relates to substituted benzo[c]phenanthrene derivatives and to the production and to the use thereof in electronic devices, and to the electronic devices themselves. The present invention relates in particular to benzo[c]phenanthrene derivatives of, e.g., formula (I) or (XV) substituted with at least one aromatic unit or at least one diarylamino unit.
Claims9
A compound of formula (I)
- wherein
- R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11
- are selected, independently of one another, from the group consisting of Ar, N(Ar)2, H, D, F, Cl, Br, CHO, N(R13)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR13═CR13Ar, CN, NO2, Si(R13)3, B(OR13)2, OSO2R13, straight-chain alkyl, alkenyl, alkoxy and thioalkoxy groups having 1 to 40 C atoms and branched, mono- or polycyclic alkyl, alkenyl, alkoxy and thioalkoxy groups having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R13, where one or more non-adjacent CH2 groups are optionally replaced by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R13, and aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R13, and a combination of these systems;
- with the proviso that at least one group of R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 is selected from the group consisting of Ar and N(Ar)2;
- Ar is on each occurrence, identically or differently, one or more unit(s) selected from the group consisting of naphthyl, anthracene, phenanthrene, 1,3,5-triazine, benzimidazole, phenothiazine, fluorene, carbazole, spirobifluorene, and combinations thereof, which are optionally substituted by one or more radicals R13, where, in the case where two Ar are bonded to the same N or P atom, the two Ar may be linked to one another by a single covalent bond or a divalent group selected from the group consisting of BR13, C(R13)2, Si(R13)2, C═O, C═NR13, C═C(R13)2, O, S, S═O, SO2, NR13, PR13 and P(═O)R13;
- R1 and R12
- are H or D atoms;
- R13 is identical or different on each occurrence and is selected from the group consisting of H, D, F, Cl, Br, I, CHO, N(R14)2, CN, NO2, Si(R14)3, B(OR14)2, OSO2R14, straight-chain alkyl, alkenyl, alkoxy and thioalkoxy groups having 1 to 40 C atoms and branched, mono- or polycyclic alkyl, alkenyl, alkoxy and thioalkoxy groups having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R14, where one or more non-adjacent CH2 groups are optionally replaced by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, and aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R14, and aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R14, and a corn bination of these systems;
- R14 is identical or different on each occurrence and is selected from the group consisting of H and an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, where one or more H atoms of the aliphatic hydrocarbon radical are optionally replaced by F.
6 more elements
A compound of formula (XV)
- wherein
- R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11
- are selected, independently of one another, from the group consisting of Ar, N(Ar)2, H, D, F, Cl, Br, I, CHO, N(R13)2, C(═O)Ar, P(═O)(Ar)2, S(═O)Ar, S(═O)2Ar, CR13═CR13Ar, CN, NO2, Si(R13)3, B(OR13)2, OSO2R13, straight-chain alkyl, alkenyl, alkoxy and thioalkoxy groups having 1 to 40 C atoms and branched, mono- or polycyclic alkyl, alkenyl, alkoxy and thioalkoxy groups having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R13, where one or more non-adjacent CH2 groups are optionally replaced by R13C═CR13, C≡C, Si(R13)2, Ge(R13)2, Sn(R13)2, C═O, C═S, C═Se, C═NR13, P(═O)(R13), SO, SO2, NR13, O, S or CONR13 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, and aromatic or heteroaromatic ring systems having 5 to 4 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R13, and aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R13, and a combination of these systems;
- Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R13, where, in the case where two Ar are bonded to the same N or P atom, the two Ar may be linked to one another by a single covalent bond or a divalent group selected from the group consisting of BR13, C(R13)2, Si(R13)2, C═O, C═NR13, C═C(R13)2, O, S, S═O, SO2, NR13, PR13 and P(═O)R13;
- with the proviso that Ar, if it is bonded directly to the aromatic skeleton of the formula (I), is different from triarylamine;
- R1 and R12
- are H or D atoms;
- R13 is identical or different on each occurrence and is selected from the group consisting of H, D, F, Cl, Br, I, CHO, N(R14)2, CN, NO2, Si(R14)3, B(OR14)2, OSO2R14, straight-chain alkyl, alkenyl, alkoxy and thioalkoxy groups having 1 to 40 C atoms and branched, mono- or polycyclic alkyl, alkenyl, alkoxy and thioalkoxy groups having 3 to 40 C atoms, each of which are optionally substituted by one or more radicals R14, where one or more non-adjacent CH2 groups are optionally replaced by R14C═CR14, C≡C, Si(R14)2, Ge(R14)2, Sn(R14)2, C═O, C═S, C═Se, C═NR14, P(═O)(R14), SO, SO2, NR14, O, S or CONR14 and where one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2, and aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R14, and aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R14, and a corn bination of these systems;
- and
- R14 is identical or different on each occurrence and is selected from the group consisting of H and an aliphatic hydrocarbon radical having 1 to 20 carbon atoms, where one or more H atoms of the aliphatic hydrocarbon radical are optionally replaced by F;
- with the proviso that at least one of the radicals R2, R3, R4, R5, R6, R7, R8, R9, R10 and R11 is B(OR13)2.
8 more elements
Dependencies are inferred from the claim text.