Materials for electronic devices
The invention relates to propellane compounds according to defined formula, to the use of said compounds in electronic devices, and to electronic devices containing one or more of the known propellane compounds. The invention also relates to methods for producing the known propellane compounds.
1 . A compound of Formula (I),
where the variables that occur are as follows:
Z is CR 1 ;
Y is not present;
n is 0;
R 1 is the same or different at each instance and are selected from H, D, F, CN, Si(R 3 ) 3 , straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; where the alkyl groups and the aromatic ring system mentioned may each be substituted by one or more R 3 radicals; and
with the proviso that two or more R 1 radicals may not be joined to one another and may not form a ring;
R 3 is the same or different at each instance and is selected from H, D, F, CN, Si(R 4 ) 3 , straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; where two or more R 3 radicals may be joined to one another and may form a ring; where the alkyl groups mentioned and the aromatic ring systems mentioned may each be substituted by one or more R 4 radicals;
R 4 is the same or different at each instance and is selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; where two or more R 4 radicals may be joined to one another and may form a ring; and where the alkyl groups and the aromatic ring systems mentioned may be substituted by F or CN;
characterized in that only one R 1 group per formula (I) is replaced by a group of Formula (A) or a group of Formula (H)
where:
L 1 is the same or different at each instance and is an aromatic ring system having 6 to 24 aromatic ring atoms or a heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more R 5 radicals;
k is 0, 1, 2 or 3;
Ar 1 is the same or different at each instance and is an aromatic ring system having 6 to 24 aromatic ring atoms or a heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more R 5 radicals;
Ar 2 is a triazinyl group which may be substituted by one or more R 5 radicals;
R 5 is the same or different at each instance and is selected from H, D, F, CN, Si(R 6 ) 3 , straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ring system mentioned may each be substituted by one or more R 6 radicals;
R 6 is the same or different at each instance and is selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by F or CN;
where the group of the Formula (A) or the group of the Formula (H) is bonded via the bond marked *.
2 . A compound as claimed in claim 1 , characterized in that Formula (I) is represented by one of Formulae (I-H-1) to (I-H-4) and (I-A-1) to (I-A-4)
where the groups that occur are as defined in claim 1 , and where “Formula (A)” is a group of the Formula (A) as defined in claim 1 , and where “Formula (H)” is a group of the Formula (H) as defined in claim 1 .
3 . The compound as claimed in claim 1 , wherein R 1 is the same or different at each instance and is selected from H, D, straight-chain or branched alkyl groups having up to 12 carbon atoms, and aromatic ring systems having 6 to 24 aromatic ring atoms; where the alkyl groups mentioned and the aromatic ring systems mentioned may each be substituted by one or more R 3 radicals.
4 . The compound as claimed in claim 1 , wherein R 3 is the same or different at each instance and is selected from H, D, F, CN, straight-chain alkyl groups having 1 to 12 carbon atoms, branched or cyclic alkyl groups having 3 to 12 carbon atoms, and aromatic ring systems having 6 to 24 aromatic ring atoms; where the alkyl groups mentioned and the aromatic ring systems mentioned may each be substituted by one or more R 4 radicals.
5 . The compound as claimed in claim 1 , wherein R 4 is the same or different at each instance and is selected from H, D, F, CN, straight-chain alkyl groups having 1 to 12 carbon atoms, branched or cyclic alkyl groups having 3 to 12 carbon atoms, and aromatic ring systems having 6 to 24 aromatic ring atoms; where the alkyl groups mentioned and the aromatic ring systems mentioned may be substituted by F or CN.
6 . The compound as claimed in claim 1 , wherein only one R 1 group per Formula (I) is replaced by a group of Formula (A).
7 . The compound as claimed in claim 1 , wherein L 1 is a divalent group selected from phenylene, biphenylene, terphenylene, naphthylene, dibenzofuran, dibenzothiophene, carbazole and fluorene, where the divalent group may be substituted by one or more R 5 radicals.
8 . The compound as claimed in claim 1 , wherein Ar 1 is the same or different at each instance and is selected from phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, spirobifluorenyl, pyridyl, pyrimidyl, triazinyl, dibenzofuranyl, benzofused dibenzofuranyl, dibenzothiophenyl, benzofused dibenzothiophenyl, carbazolyl, and benzofused carbazolyl, and combinations of two, three or four of these groups, where the groups mentioned may each be substituted by one or more R 5 radicals.
9 . A process for preparing the compound as claimed in claim 1 which comprises first preparing the alkoxy-substituted base skeleton and then converting the alkoxy-substituted base skeleton in a further step to a reactive compound, preferably to a triflate derivative, which is converted in a further step by transition metal-catalyzed coupling reaction.
10 . An oligomer, polymer or dendrimer containing one or more compounds as claimed in claim 1 , wherein the bond(s) to the polymer, oligomer or dendrimer may be localized at any desired positions substituted by R 1 or R 5 .
11 . A formulation comprising one or more compounds as claimed claim 1 and at least one solvent.
12 . An electronic device selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs), comprising at least one compound as claimed in claim 1 .
13 . The device as claimed in claim 12 , wherein the device is an electroluminescent device comprising anode, cathode and at least one organic layer, wherein the compound is present in a hole-transporting layer, as matrix material in an emitting layer, or in an electron-transporting layer.
14 . The compound as claimed in claim 1 , wherein R 1 is selected, identically or differently, from H and D.
15 . The compound as claimed in claim 1 , wherein only one R 1 group in Formula (I) is replaced by a group of the Formula (H).
16 . The compound as claimed in claim 1 , characterized in that only one R 1 group in Formula (I) is replaced by a group of the Formula (A), and further characterized in that index k=0, and further characterized in that R 1 is selected, identically or differently, from H and D.
17 . The compound as claimed in claim 1 , characterized in that Formula (I) is represented by one of the Formulae (I-H-1), (I-H-3), (I-H-4), (I-A-1), (I-A-3) and (I-A-4)
where the groups that occur are as defined in claim 1 , and where “Formula (A)” is a group of the Formula (A) as defined in claim 1 , and where “Formula (H)” is a group of the Formula (H) as defined in claim 1 , and wherein R 1 is selected, identically or differently, from H and D.
18 . The compound as claimed in claim 1 , characterized in that Formula (I) is represented by one of Formulae (I-H-1), (I-H-3) and (I-H-4),
where index k is 0, and wherein R 1 is selected, identically or differently, from H and D.