Connections for electronic devices

Abstract

Combination of the formula (1-1) where the symbols appearing are defined as follows: X 1 is a divalent group NR 1 ; X 2 , X 3 are, in each occurrence, a divalent group, selected equally or differently from C(R) 1 )2, NR 1 , O and S; Z is selected from CR in each occurrence, either the same or different. 1 and N; R 1 is the same or different in each occurrence H, D, F, Cl, Br, I, B(OR 3 )2, CHO, C(O)R 3 , CR 3 =C(R 3 )2, CN, COOR 3 , CON(R 3 )2, Si(R 3 )3, N(R 3 )2, NO2, P(=O)(R 3 )2, OSO2R 3 , OH, S(=O)R 3 , S(=O)2R 3, a straight-chain alkyl, alkoxy or thioalkyl group with 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group with 3 to 40 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, each with one or more R groups 3 It can be substituted, with one or more CH2 groups being 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 , -COO-, -CONR 3 -, NR 3 , P(=O)(R 3 ), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is replaced by one or more R groups 3may be substituted, or an aryloxy, heteroaryloxy, aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, separated by one or more R groups 3 may be substituted, or a combination of these systems; R 3 is the same or different in each occurrence H, D, F, Cl, Br, I, B(OR 4 )2, CHO, C(O)R 4 , CR 4 =C(R 4 )2, CN, COOR 4 , CON(R 4 )2, Si(R 4 )3, N(R 4 )2, NO2, P(=O)(R 4 )2, OSO2R 4 , OH, S(=O)R 4 , S(=O)2R 4 , a straight-chain alkyl, alkoxy or thioalkyl group with 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group with 3 to 40 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, each with one or more R groups 4 It can be substituted, with one or more CH2 groups being 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 , -COO-, -CONR 4 -, NR 4 , P(=O)(R 4 ), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is replaced by one or more R groups 4 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 4 may be substituted, or a combination of these systems; R 4 is the same or different in each occurrence H, D, F or an aliphatic, aromatic and / or heteroaromatic organic residue with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F.

Claims

[1] Compound of formula (1-1)where the symbols appearing are defined as follows: X 1 is a divalent group NR 1 ; X 2 , X 3 are at each occurrence a divalent group, identically or differently selected from C(R 1 )2, NR 1 , O and S; Z is the same or different at each occurrence selected from CR 1 and N; R 1 is the same or different at each occurrence: H, D, F, Cl, Br, I, B(OR 3 )2, CHO, C(O)R 3 , CR 3 =C(R 3 )2, CN, COOR 3 , CON(R 3 )2, Si(R 3 )3, N(R 3 )2, NO2, P(=O)(R 3 )2, OSO2R 3 , OH, S(=O)R 3 , S(=O)2R 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, each of which is substituted by one or more radicals R 3 may be substituted, with one or more CH2 groups being 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 , -COO-, -CONR 3 -, NR 3 , P(=O)(R 3 ), -O-, -S-, SO or SO2 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each substituted by one or more radicals R 3may be substituted, or an aryloxy, heteroaryloxy, aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R 3 may be substituted, or a combination of these systems; R 3 is the same or different at each occurrence: H, D, F, Cl, Br, I, B(OR 4 )2, CHO, C(O)R 4 , CR 4 =C(R 4 )2, CN, COOR 4 , CON(R 4 )2, Si(R 4 )3, N(R 4 )2, NO2, P(=O)(R 4 )2, OSO2R 4 , OH, S(=O)R 4 , S(=O)2R 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, each of which is substituted by one or more radicals R 4 may be substituted, with one or more CH2 groups being 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 , -COO-, -CONR 4 -, NR 4 , P(=O)(R 4 ), -O-, -S-, SO or SO2 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each substituted by one or more radicals R 4 may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 4 may be substituted, or a combination of these systems; 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 one or more H atoms may be replaced by D or F. [2] A compound according to claim 1, characterized bythat no more than three Z groups per aromatic ring are N and the remaining Z groups are CR 1 are. [3] A process for preparing a compound according to formula (I) according to claim 1, characterized by that the reactions take place according to the following reaction scheme,where in a first step, a halogen-substituted carbazole derivative is reacted with an anthranilic acid derivative in a Ullmann coupling, and in a subsequent second step, the coupling product resulting from the Ullmann coupling is reacted with an alkyllithium compound and then treated with acid, whereby a ring closure occurs, and in a subsequent third step, the product from the second step is arylated in a Hartwig-Buchwald coupling at the NH group, where Hal represents a halogen atom, R represents an organic radical within the definition of claim 1, and Ar represents an aromatic or heteroaromatic ring system within the definition of claim 1. [4] Use of a compound according to claim 1 or 2 in an electronic device. [5] Use according to claim 4, characterized by that the electronic device is an organic electroluminescent device. [6] Use of a compound according to claim 1 or 2 as matrix material in combination with one or more further matrix materials in an emitting layer of an electronic device.