Materials for electronic devices
The present invention relates to compounds of the formula (I), to the use of compounds of the formula (I) in electronic devices and electronic devices comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compounds of the formula (I) and to formulations comprising one or more compounds of the formula (I).
1. A compound of the formulae (Ia-1)-(Ia-10), (Ib-5)-(Ib-8), (Ib-11)-(Ib-19) or (Ib-20)
where the following applies to the symbols and indices occurring:
Z is on each occurrence, identically or differently, CR 2 or N, where not more than two adjacent groups Z may simultaneously be equal to N;
R 1 is on each occurrence, identically or differently, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , C(═O)OR 3 , C(═O)NR 3 2 , P(═O)(R 3 ) 2 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R 3 , or a combination of these systems, where two or more radicals R 1 are optionally linked to one another and may form an aliphatic or aromatic ring;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)NR 3 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OS(═O) 2 R 3 , OH, S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more non-adjacent CH 2 groups in the above-mentioned groups is optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, S═O or S(═O) 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of these systems, where two or more radicals R 2 are optionally linked to one another and may form an aliphatic or a condensed aryl or heteroaryl group;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, B(OR 4 ) 2 , CHO, C(═O)R 4 , CR 4 ═C(R 4 ) 2 , CN, C(═O)OR 4 , C(═O)NR 4 2 , Si(R 4 ) 3 , N(R 4 ) 2 , NO 2 , P(═O)(R 4 ) 2 , OS(═O) 2 R 4 , OH, S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 4 and where one or more non-adjacent CH 2 groups in the above-mentioned groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, S═O or S(═O) 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or a combination of these systems, where two or more radicals R 3 are optionally linked to one another and may form an aliphatic or aromatic ring; and
R 4 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R 4 here may also be linked to one another and form an aliphatic or aromatic ring.
2. The compound according to claim 1 , wherein 0, 1 or 2 groups Z per aromatic or heteroaromatic six-membered ring are equal to N.
3. The compound according to claim 1 , wherein R 1 represents on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R 3 .
4. The compound according to claim 1 , wherein at least one group is present as substituent R 1 or R 2 which is selected from electron-deficient heteroaryl groups, aromatic or heteroaromatic ring systems having 10 to 30 aromatic ring atoms and from arylamine groups, each of which is optionally substituted by one or more radicals as defined in claim 1 .
5. A process for the preparation of the compound of the formulae (Ia-1)-(Ia-10), according to claim 1 , which comprises ring-closure reacting one or more condensed heteroaromatic five-membered rings.
6. An oligomer, polymer or dendrimer comprising one or more compounds of the formulae (Ia-1)-(Ia-10), according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any position in formulae (Ia-1)-(Ia-10), substituted by R 1 or R 2 .
7. A formulation comprising at least one compound of the formulae (Ia-1)-(Ia-10), according to claim 1 and at least one solvent.
8. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 6 and at least one solvent.
9. An electronic device comprising the compound according to claim 1 .
10. An electronic device comprising the polymer, oligomer or dendrimer according to claim 6 .
11. An organic electroluminescent device (OLED) comprising the compound according to claim 1 .
12. The Electronic device according to claim 9 , wherein in the device is 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, an organic laser diode or an organic electroluminescent device.
13. An organic electroluminescent device which comprises the compound according to claim 1 is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or is employed as matrix material in an emitting layer and/or as electron-transport material in an electron-transport layer.
14. An organic electroluminescent device which comprises the polymer, oligomer or dendrimer according to claim 6 is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or is employed as matrix material in an emitting layer and/or as electron-transport material in an electron-transport layer.
15. The compound according to claim 1 , wherein two or more radicals R 2 are linked to one another and form an aliphatic ring or a condensed aryl or heteroaryl group.
16. The compound according to claim 15 , wherein two or more radicals R 2 are linked to one another and form a heteroaryl group which has 4 to 8 aromatic ring atoms.