Compounds for electronic devices
The present invention relates to compounds of the formula (I) and to the use thereof in organic electronic devices, and to organic electronic devices which comprise compounds of the formula (I), preferably as hole-transport materials and/or as matrix materials, in particular in combination with a further matrix material.
1. A compound of the formula (II)
where the following applies to the symbols and indices occurring:
Y is on each occurrence, identically or differently, a single bond or C(R 2 ) and
precisely one group Y represents a single bond and precisely one further group Y is C(R 2 ) 2 ;
T 2 is a single bond;
Ph is a phenyl group, which is optionally substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, 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, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 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 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, where two or more radicals R 1 and/or R 2 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, 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, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 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 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, where two or more radicals R 1 and/or R 2 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═ 0 ) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , OH, 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, each of which is optionally substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 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 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 4 , or a combination of these systems, where two or more radicals R 3 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 4 is on each occurrence, identically or differently, 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 identical or different substituents R 4 here may also be linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
n is on each occurrence, identically or differently, 0 or 1, where the sum of the values of n is equal to 1 and where, for n=0, a group R′ is bonded instead of a group Y;
m2 is 0 or 1, where, for m2=0, a group R 1 is bonded instead of a group T 2 ;
where the following structures are excluded:
and where not more than one group R 1 which represents a group of the formula —N(R 3 ) 2 , where R 3 is an aryl group, is optionally bonded to a single triarylamine group in formula (I).
2. The compound according to claim 1 , wherein R 1 is selected on each occurrence, identically or differently, from H, D, F, CN, Si(R 3 ) 3 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more adjacent or non-adjacent CH 2 groups is optionally replaced by —C≡C—, R 3 C═CR 3 , Si(R 3 ) 2 , C═O, C═NR 3 , NR 3 , O, S, COO or CONR 3 , or an aryl or group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 .
3. The compound according to claim 1 , wherein R 2 is selected on each occurrence, identically or differently, from H, D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms or an aryl group having 6 to 18 carbon atoms, where the said groups may each be substituted by one or more groups R 3 .
4. The compound according to claim 1 , wherein at least one group R 2 which represents an aryl group having 6 to 10 carbon atoms which is substituted by one or more radicals R 3 must be present.
5. The compound according to claim 1 , wherein the group Ph conforms to one of the formulae (Ph-1) and (Ph-2):
where the bonds to the two nitrogen atoms are represented by the dashed lines, and the symbols # mark the position of the bond to a group Y, if present, and where the structures is optionally substituted in all free positions by radicals R 1 as defined in claim 1 .
6. A compound which conforms to one of the following (I-1), (I-2), (I-3), (I-11), (I-12) or (I-13):
where
L is selected on each occurrence, identically or differently, from C(R 2 ) 2 and
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, 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, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 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 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, where two or more radicals R 1 and/or R 2 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, 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, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 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 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 , or a combination of these systems, where two or more radicals R 1 and/or R 2 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , OH, 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, each of which is optionally substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 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 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 4 , or a combination of these systems, where two or more radicals R 3 is optionally linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system; and
R 4 is on each occurrence, identically or differently, 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 identical or different substituents R 4 here may also be linked to one another and may form a mono- or polycyclic, aliphatic or aromatic ring system.
7. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any positions substituted by R 1 or R 2 in formula (I).
8. A formulation comprising at least one compound according to claim 1 and at least one solvent.
9. A formulation comprising at least polymer, oligomer or dendrimer according to claim 7 and at least one solvent.
10. A process for the preparation of a compound according to claim 1 , which comprises carrying out at least one ring-closure reaction for the introduction of a bridging group Y, T 2 or L.
11. An electronic device comprising the compound according to claim 1 .
12. An electronic device comprising the polymer, oligomer or dendrimer according to claim 7 .
13. The Electronic device according to claim 11 , wherein the device is an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser) or an organic electroluminescent devices (OLED).
14. An organic electroluminescent device which comprises the compound according to claim 1 as hole-transport material in a hole-transport layer or hole-injection layer and/or as matrix material in an emitting layer.
15. An organic electroluminescent device which comprises the compound according to claim 1 as hole-transport material in a hole-transport layer or hole-injection layer and/or as matrix material, in combination with one or more further matrix materials, in an emitting layer.
16. An organic electroluminescent device which comprises the polymer, oligomer or dendrimer according to claim 7 as hole-transport material in a hole-transport layer or hole-injection layer and/or as matrix material in an emitting layer.
17. An organic electroluminescent device which comprises the polymer, oligomer or dendrimer according to claim 7 as hole-transport material in a hole-transport layer or hole-injection layer and/or as matrix material, in combination with one or more further matrix materials, in an emitting layer.