Heterocyclic compounds

A compound of the general formula (1)

• where the symbols used are as follows:
• Q is the same or different at each instance and is X═X, O, NR, S, SO, SO2, PR, POR or BR, where at least one Q is X═X;
• X1 is CR or N;
• X is the same or different at each instance and is N or CR;
• Y is the same or different at each instance and is CR;
• R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R1)2, CN, NO2, OH, COOH, C(═O)N(R1)2, Si(R1)3, B(OR1)2, C(═O)R1, P(═O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, each of which may be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C═CR1, C≡C, Si(R1)2, C═O, NR1, O, S or CONR1 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R1 radicals;
• at the same time, two adjacent R radicals together may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
• R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, C≡C, Si(R2)2, C═O, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals;
• at the same time, two or more adjacent R1 radicals together, or R1 together with R, may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
• R2 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
• at the same time, two or more R2 substituents together may also form a mono- or polycyclic aliphatic ring system;
• which is characterized in that
• the respective R radicals of the two Y groups together with the carbon atoms of the heteroaromatic ring form a ring of the following formulae:
• where
• A1, A3 is the same or different at each instance and is C(R3)2, O, S, NR3 or C(═O);
• A2 is C(R1)2, O, S, NR3 or C(═O);
• G is a bivalent group selected from O, S, N(R2), B(R2), Si(R2)2, C═O, C═NR2, C═C(R2)2, S═O, SO2, P(R2) and P(═O)R2, an alkylene group which has 1, 2 or 3 carbon atoms and may be substituted by one or more R2 radicals, —CR2═CR2- or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R2 radicals;
• and where the carbon-carbon double bond shown in the formulae (5) to (11) corresponds to an aromatic double bond from the heteroaromatic ring to which the groups of the formulae (5) to (11) bind;
• R3 is the same or different at each instance and is F, a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, C≡C, Si(R2)2, C═O, NR2, O, S or CONR2, and where one or more hydrogen atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 24 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 24 aromatic ring atoms and may be substituted by one or more R2 radicals;
• at the same time, two R3 radicals bonded to the same carbon atom together may form an aliphatic or aromatic ring system and thus form a Spiro system;
• in addition, R3 with an adjacent R or R1 radical may form an aliphatic ring system;
• with the proviso that no two identical heteroatoms in the aforementioned groups are bonded directly to one another and no two C═O groups are bonded directly to one another, and, in addition,
• if the two Y groups together are a ring structure of the formulae (12) or (13)
• the X1 radical is not a group of the formula (14)
• in which X is as defined above and the dotted lines represent the bonds of the carbon atom of the X1 radical to two further carbon atoms of the ring including the X1 radical of formula (1);
• wherein, in the ring structures of one of the formulae (5), (6), (7), (8), (9), (10), and/or (11), not more than one of the A1, A2, and A3 groups is O, S or NR3.