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COMPOUNDS FOR STRUCTURING FUNCTIONAL LAYERS OF ORGANIC ELECTROLUMINESCENT DEVICES

20230380267 · 2023-11-23

    Inventors

    Cpc classification

    International classification

    Abstract

    The present invention relates to the use of compounds for structuring of at least one functional layer of an organic electronic device. The present invention further relates to preferred compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.

    Claims

    1.-26. (canceled)

    27. A method comprising structuring at least one functional layer of an organic electronic device with a compound comprising at least one structuring element of the formula (SE-I) ##STR00240## where the ring Cy represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted with one or more R radicals, the dashed bond is the bonding site and furthermore: X is CR, N or C if a group binds to X; R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar′).sub.2, N(R.sup.1).sub.2, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, C(═O)Ar′, C(═O)R.sup.1, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.1C═CR.sup.1, C≡C, Si(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, SO or SO.sub.2 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 R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, two R radicals may also together or with a further group form a ring system; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, it is possible for two Ar′ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent R.sup.1 radicals together may form a ring system; at the same time, one or more R.sup.1 radicals may form a ring system with a further part of the compound; Ar″ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a single bond or a bridge selected from B(R.sup.2), C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, C═C(R.sup.2).sub.2, O, S, S═O, SO.sub.2, N(R.sup.2), P(R.sup.2) and P(═O)R.sup.2; R.sup.2 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R.sup.2 together may form a ring system.

    28. The method to claim 27, characterized in that the ring Cy in a structuring element of formula (SE-I) may be represented by one of the following formulae (Cy-1) to (Cy-10) ##STR00241## where R.sup.1 and R.sup.2 have the definitions given in claim 27, the dotted bonds signify the linkage of the two carbon atoms in the structuring element of the formula (SE-I) and in addition: Z.sup.1, Z.sup.3 is the same or different at each instance and is C(R.sup.3).sub.2, O, S, NR.sup.3 or C(═O); Z.sup.2 is C(R.sup.1).sub.2, O, S, NR.sup.1 or C(═O), where two adjacent groups Z.sup.2 may represent —CR.sup.1═CR.sup.1— or an ortho-bonded arylene or heteroarylene group having 5 to 14 aromatic ring atoms which may be substituted by one or more R.sup.1 radicals; G is an alkylene group which has 1, 2 or 3 carbon atoms and may be substituted by one or more R.sup.1 radicals, —CR.sup.1═CR.sup.1— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; R.sup.3 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two R.sup.3 radicals which are bonded to the same carbon atom together may form an aliphatic or aromatic ring system and thus form a spiro system; furthermore, R.sup.3 may form an aliphatic ring system with an adjacent R or R.sup.1 radical; with the proviso that no two heteroatoms in these groups are bonded directly to one another and no two C═O groups are bonded directly to one another.

    29. The method to claim 27, characterized in that the structuring element of the formula (SE-I) may be represented by a formula (SE-1) to (SE-60), ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## where: G is an alkylene group which has 1, 2 or 3 carbon atoms and may be substituted by one or more R.sup.1 radicals, —CR.sup.1═CR.sup.1— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; R.sup.3 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two R.sup.3 radicals which are bonded to the same carbon atom together may form an aliphatic or aromatic ring system and thus form a spiro system; furthermore, R.sup.3 may form an aliphatic ring system with an adjacent R or R.sup.1 radical; Y.sup.1, Y.sup.3 are the same or different at each instance and are O, S, NR.sup.3 or C(═O); Y.sup.2 is the same or different at each instance and is O, S, NR.sup.1 or C(═O); the index m is 0, 1, 2, 3 or 4; the index s is 0, 1, 2, 3, 4, 5 or 6; the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

    30. The method to claim 27, characterized in that the structuring element of the formula (SE-I) can be represented by a formula (SE-1a) to (SE-60a) ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## where: G is an alkylene group which has 1, 2 or 3 carbon atoms and may be substituted by one or more R.sup.1 radicals, —CR.sup.1═CR.sup.1— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; R.sup.3 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two R.sup.3 radicals which are bonded to the same carbon atom together may form an aliphatic or aromatic ring system and thus form a spiro system; furthermore, R.sup.3 may form an aliphatic ring system with an adjacent R or R.sup.1 radical; n is 0, 1, 2 or 3; m is 0, 1, 2, 3 or 4; the index s is 0, 1, 2, 3, 4, 5 or 6; the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9

    31. The method to claim 27, characterized in that the compound comprises at least one aromatic or heteroaromatic ring system having at least two fused aromatic or heteroaromatic rings.

    32. The method to claim 31, characterized in that the aromatic or heteroaromatic ring system having two fused aromatic or heteroaromatic rings is selected from the groups of the formulae (Ar-1) to (Ar-18) ##STR00262## ##STR00263## ##STR00264## where X′ is N or CR.sup.a, L.sup.1 represents a bond or an aromatic or heteroaromatic ring system which has 5 to 40, aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, where the dotted bond marks the position of attachment, and in addition: R.sup.a is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar′).sub.2, N(R.sup.1).sub.2, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, C(═O)Ar′, C(═O)R.sup.1, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.1C═CR.sup.1, C≡C, Si(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, SO or SO.sub.2 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 R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, two R.sup.a radicals may also together or with a further group, for example with one or more of the R radicals, form a ring system, where the symbols R.sup.1 and Ar′ have the following definitions: Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, it is possible for two Ar′ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a single bond or a bridge selected from B(R.sup.1), C(R.sup.1).sub.2, Si(R.sup.1).sub.2, C═O, C═NR.sup.1, C═C(R.sup.1).sub.2, O, S, S═O, SO.sub.2, N(R.sup.1), P(R.sup.1) and P(═O)R.sup.1; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent R.sup.1 radicals together may form a ring system; at the same time, one or more R.sup.1 radicals may form a ring system with a further part of the compound.

    33. Compound comprising at least one structure of the formula (I), suitable for the method to claim 27, ##STR00265## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals, where the symbol R has the definition given in claim 27 and the further symbols are as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; R.sup.b is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar′).sub.2, N(R.sup.1).sub.2, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, C(═O)Ar′, C(═O)R.sup.1, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R′, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.1C═CR.sup.1, C≡C, Si(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, SO or SO.sub.2 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 R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, two R.sup.b radicals may also together or with a further group, for example with one or more of the R.sup.c radicals, form a ring system, where the symbols R.sup.1 and Ar′ have the definitions given in claim 27 above; R.sup.c is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO.sub.2, N(Ar′).sub.2, N(R.sup.1).sub.2, C(═O)N(Ar′).sub.2, C(═O)N(R.sup.1).sub.2, C(Ar′).sub.3, C(R.sup.1).sub.3, Si(Ar′).sub.3, Si(R.sup.1).sub.3, B(Ar′).sub.2, B(R.sup.1).sub.2, C(═O)Ar′, C(═O)R.sup.1, P(═O)(Ar′).sub.2, P(═O)(R.sup.1).sub.2, P(Ar′).sub.2, P(R.sup.1).sub.2, S(═O)Ar′, S(═O)R.sup.1, S(═O).sub.2Ar′, S(═O).sub.2R.sup.1, OSO.sub.2Ar′, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.1C═CR.sup.1, C≡C, Si(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, —C(═O)O—, —C(═O)NR.sup.1—, NR.sup.1, P(═O)(R.sup.1), —O—, —S—, SO or SO.sub.2 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 R.sup.1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, two R.sup.c radicals may also together or with a further group, for example with one or more of the R.sup.b radicals, form a ring system, where the symbols R.sup.1 and Ar′ have the definitions given in claim 27 above; characterized in that the ring Cy′ has at least one, substituents R comprising at least one, fluorine atom.

    34. Compound comprising at least one structure of the formulae (I-1) to (I-21), suitable for the method to claim 27, ##STR00266## ##STR00267## ##STR00268## ##STR00269## where the symbols are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one radical R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    35. Compound comprising at least one structure of the formula (II), suitable for the method to claim 27, ##STR00270## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals, and the symbols L.sup.2, X.sup.1 and X.sup.2 are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group, characterized in that the ring Cy′ has at least one, substituent R comprising at least one, fluorine atom.

    36. Compound comprising at least one structure of the formulae (II-1) to (II-21), suitable for the method to claim 27, ##STR00271## ##STR00272## ##STR00273## ##STR00274## where the symbols are as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group, preferably a bond or an aromatic or heteroaromatic ring system which has 5 to 40, aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, where the symbol R.sup.1 has the definition set out in claim 27 above; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one radical R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms. at least one radicals R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    37. Compound comprising at least one structure of the formula (III), suitable for the method to claim 27, ##STR00275## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals, where the symbol R has the definition given in claim 27, and the symbols L.sup.2, X.sup.1 and X.sup.2 are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group characterized in that the ring Cy′ has at least one, substituent R comprising at least one, fluorine atom.

    38. Compound comprising at least one structure of the formulae (III-1) to (III-21), suitable for the method to claim 27, ##STR00276## ##STR00277## ##STR00278## ##STR00279## where the symbols are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one, radicals R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    39. Compound comprising at least one structure of the formula (IV), suitable for the method to claim 27, ##STR00280## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals, and the symbols L.sup.2, X.sup.1 and X.sup.2 have the following definitions: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; characterized in that the ring Cy′ has at least one, substituent R comprising at least one, fluorine atoms.

    40. Compound comprising at least one structure of the formulae (IV-1) to (IV-21), suitable for the method to claim 27, ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## where the symbols are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one, radical R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    41. Compound comprising at least one structure of the formula (V), suitable for the method to claim 27, ##STR00286## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals and the symbols L.sup.2, X.sup.1 and X.sup.2 are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; characterized in that the ring Cy′ has at least one, substituent R comprising at least one, fluorine atom.

    42. Compound comprising at least one structure of the formulae (V-1) to (V-21) suitable for the method to claim 27, ##STR00287## ##STR00288## ##STR00289## ##STR00290## where the symbols are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one radical R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    43. Compound comprising at least one structure of the formula (VI), suitable for the method to claim 27, ##STR00291## where the ring Cy′ represents a non-aromatic or non-heteroaromatic ring having 5 to 60 ring atoms which may be substituted by one or more R radicals, and the symbols L.sup.2, X.sup.1 and X.sup.2 are defined as follows: X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; characterized in that the ring Cy′ has at least one, substituents R comprising at least one, fluorine atom.

    44. Compound comprising at least one structure of the formulae (VI-1) to (VI-21), suitable for the method to claim 27, ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## where the symbols are defined as follows, X.sup.1 is CR.sup.b if the L.sup.2 group binds to X.sup.1, or N or C; X.sup.2 is CR.sup.c if the L.sup.2 group binds to X.sup.2, or N or C; L.sup.2 is a linking group; G′ is an alkylene group having 1, 2 or 3 carbon atoms, which may be substituted by one or more R.sup.4 radicals, —CR.sup.4═CR.sup.4— or an ortho-bonded arylene or heteroarylene group which has 5 to 14 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; Y.sup.4, Y.sup.6 are the same or different at each instance and are O, S, NR.sup.5 or C(═O); Y.sup.5 is the same or different at each instance and is O, S, NR.sup.4 or C(═O); R.sup.4, R.sup.5 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar″).sub.2, N(R.sup.2).sub.2, C(═O)Ar″, C(═O)R.sup.2, P(═O)(Ar″).sub.2, P(Ar″).sub.2, B(Ar″).sub.2, B(R.sup.2).sub.2, C(Ar″).sub.3, C(R.sup.2).sub.3, Si(Ar″).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a combination of these systems; at the same time, two or more adjacent radicals R.sup.4, R.sup.5 together may form a ring system; at the same time, one or more of the radicals R.sup.4, R.sup.5 may form a ring system with a further part of the compound, characterized in that at least one radical R.sup.4, R.sup.5 is/are selected from F or a fluorinated alkyl radical having 1 to 20 carbon atoms.

    45. Oligomers, polymers or dendrimers comprising one or more compounds according to claim 33, wherein, rather than a hydrogen atom or a substituent, one or more bonds to the respective constitutional isomer in the mixture are present to form the polymer, oligomer or dendrimer.

    46. Electronic device comprising at least one compound, as defined in claim 27 wherein the electronic device is selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells or organic laser diodes.

    Description

    EXAMPLES

    [0242] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective figures in square brackets or the numbers quoted for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds that can have multiple enantiomeric, diastereomeric or tautomeric forms, one form is shown in a representative manner.

    A: Synthesis of the Synthons

    Example S1

    [0243] ##STR00147##

    [0244] A mixture of 26.1 g (100 mmol) of 5-chloro-1,1,2,2,3,3-hexafluoro-2,3-dihydro-1H-indane [97586-28-2], 27.9 g (110 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) [73183-34-3], 29.5 g (300 mmol) of potassium acetate, anhydrous [127-08-2], 1.64 g (4 mmol) of SPhos [657408-07-6], 449 mg (2 mmol) of palladium(II) acetate, 50 g of glass spheres (3 mm diameter) and 400 ml of dioxane is stirred at 90° C. for 16 h. The mixture is subjected to hot filtration with suction through a celite bed pre-slurried with dioxane, the filtrate is concentrated to dryness, the crude product is subjected to extraction by stirring with 150 ml of methanol and recrystallized from acetonitrile. Alternatively, the residue of the filtrate concentrated to dryness may be subjected to an extractive workup (ethyl acetate/water). Yield: 28.7 g (81 mmol) 81%; purity: about 97% by .sup.1H NMR.

    [0245] The following compounds can be prepared analogously

    TABLE-US-00002 Ex Reactants Product Yield S2 [00148]embedded image [00149]embedded image 47% 52267-75-1 S3 [00150]embedded image [00151]embedded image 53% 124862-99-3 S4 [00152]embedded image   1780648-78-3 [00153]embedded image 77% S5 [00154]embedded image   114851-24-0 [00155]embedded image 68% S6 [00156]embedded image   33070-32-5 [00157]embedded image   70% 1562418-39-6 S7 [00158]embedded image   [00159]embedded image 75% 2304436-82-4 S8 [00160]embedded image   [00161]embedded image 67% 1782843-22-4 S9 [00162]embedded image   1783554-73-3 [00163]embedded image 73% S10 [00164]embedded image   1782512-81-5 [00165]embedded image 68% S11 [00166]embedded image   1421634-71-0 [00167]embedded image 70% S12 [00168]embedded image   [00169]embedded image 81% 60123-60-6 S13 [00170]embedded image   [00171]embedded image 79% 72046-35-6 S14 — [00172]embedded image — 1562418-25-0 S15 [00173]embedded image   [00174]embedded image 70% 666732-28-1 1154741-10-2 S16 — [00175]embedded image — 1312464-73-5 S17 — [00176]embedded image — 1562418-16-9 S18 — [00177]embedded image — 1912467-76-5 S19 —  [00178]embedded image — 1562418-51-2 S20 — [00179]embedded image — 1562418-31-8 S21 — [00180]embedded image — 853998-14-8 S22 — [00181]embedded image — 1010385-53-1 S23 — [00182]embedded image — 1801624-61-2 S24 — [00183]embedded image — 1801624-63-4

    B: Synthesis of the Compounds

    [0246] ##STR00184##

    [0247] A mixture of 35.2 g (100 mmol) of S1, 33.3 g (100 mmol) of 4-bromo-1,1′-binaphthalene [49610-33-5], 31.8 g (300 mmol) of sodium carbonate [497-19-8], 1.48 g (2 mmol) of bis(tricyclohexylphosphine)palladium(II) chloride [29934-17-6], 5 drops of hydrazine hydrate [7803-57-8], 300 ml of toluene, 100 ml of isopropanol and 300 ml of water is stirred at 80° C. for 16 h. After cooling, the solids are filtered off with suction, and the filtrate is washed twice with 200 ml each time of water and twice with 100 ml each time of methanol, and dried under reduced pressure. The solids are taken up in 300 ml of dichloromethane and filtered through a silica gel bed in the form of a DCM slurry, 200 ml of methanol is added to the filtrate, and the mixture is concentrated to a volume of about 100 ml under reduced pressure. The crystallized product is filtered off with suction and dried under reduced pressure. Purification is effected via hot extraction crystallization three times from acetonitrile, or by chromatography on silica gel and subsequent fractional sublimation. Yield: 34.6 g (72 mmol), 72%; purity: >99.5% by HPLC.

    [0248] The following compounds can be prepared analogously:

    TABLE-US-00003 The following compunds can be prepared analogously: Ex. Reactants Product Yield  2 S2 or alternatively   [00185]embedded image   in THF, anhydrous, triethylamine base   [00186]embedded image [00187]embedded image 68% 23674-17-1  3 S3   [00188]embedded image   1158227-46-3 [00189]embedded image 70%  4 S4   [00190]embedded image   2421137-98-4 [00191]embedded image 65%  5 S5   [00192]embedded image   1062556-32-4 [00193]embedded image 60%  6 S6   [00194]embedded image   1647103-06-7 [00195]embedded image 52%  7 S7   [00196]embedded image   1450898-43-7 [00197]embedded image 68%  8 S8   [00198]embedded image   1846602-60-5 [00199]embedded image 65%  9 S9   [00200]embedded image   2112854-24-5 [00201]embedded image 76% 10 S10   [00202]embedded image   2176471-19-3/50 mmol [00203]embedded image 55% 11 S11   [00204]embedded image   1304130-05-9 [00205]embedded image 67% 12 S12   [00206]embedded image   15810-15-8/50 mmol [00207]embedded image 72% 13 S13   [00208]embedded image   74897-21-5 [00209]embedded image 70% 14 S14   [00210]embedded image [00211]embedded image 69% 1714-29-0 15 S15   [00212]embedded image   1273319-86-0 [00213]embedded image 74% 16 S16   [00214]embedded image   2251815-62-8 [00215]embedded image 54% 17 S17   [00216]embedded image   2446780-51-2 [00217]embedded image 79% 18 S18   [00218]embedded image   1448535-09-8 [00219]embedded image 83% 19 S19   [00220]embedded image   1616514-34-1 [00221]embedded image 67% 20 S20   [00222]embedded image   522616-11-1 [00223]embedded image 70% 21 S21   [00224]embedded image   1673545-11-3 [00225]embedded image 77% 22 S22   [00226]embedded image   23683-68-3 [00227]embedded image 75% 23 S23   [00228]embedded image   2036123-44-9 [00229]embedded image 61% 24 S24   [00230]embedded image   1579998-22-3/50 mmol [00231]embedded image 78%

    Structuring of Metal Layers:

    [0249] The examples that follow present the results for structuring of metals and metal mixtures (alloys).

    [0250] For this purpose, suitable components—as described below—are first produced and then subjected to a measurement of transmittance differential. In the regions in which the compounds of the invention have prevented metal deposition, i.e. structuring has been effected, transmittance is high (>90%).

    [0251] Cleaned substrates (quartz glass plates, 40×40 mm, cleaning in Miele laboratory glass cleaner, Merck Extran detergent) are pre-treated with UV ozone for 25 minutes (PR-100 UV ozone generator, from UVP). The full area is subjected to vapour deposition under high vacuum (˜10.sup.−5-˜10.sup.−7 mbar) of a layer of the electron conductor ETM1, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)phenyl-1H-benzo[D]imidazole [561064-11-7], thickness 30 nm. Alternatively, it is possible to apply other electron conductors or mixtures of electron conductors that are applied by coevaporation, and to use other organic functional materials (see table). The layer thicknesses are monitored here by means of a referenced (tooled) crystal oscillator as usual in the prior art in OLED construction.

    [0252] A shadowmask is used to shadow two quarters, namely region 1=transmittance reference 1 and region 2 of the substrate area. The unshadowed regions 3=transmittance reference 2 and region 4 are each subjected to vapour deposition of layers of the compounds of the invention (thickness 30 nm). Then regions 1 and 3 are shadowed and 2 and 4 are exposed, and a metal or metal mixture (alloy) is applied by vapour deposition (for deposition rate and thickness see table). The metal mixtures are produced by coevaporation from two separate sources.

    [0253] The metal deposition is characterized by means of a relative transmittance measurement with light of wavelength 500-550 nm. The transmittance of region 1=transmittance reference 1 serves to correct the transmittance of region 2, i.e. of the glass and the ETM1 layer, and is set to transmittance=100%. The transmittance of region 3=transmittance reference 2 serves to correct the transmittance of region 4, i.e. of the glass, the ETM1 and the layer of the compound of the invention, and is set to transmittance=100%. Then transmittance in regions 2 and 4 is measured and each set relative to references 1 and 3.

    [0254] In regions in which a metal layer has been deposited, transmittance will be very low or zero, in regions in which very little or no metal layer has been deposited, transmittance will be >90% or more.

    TABLE-US-00004 TABLE 1 Compound of Transmittance [%] Transmittance [%] Ex. the invention Region 2 region 4 ETM1 Magnesium, 2 A/s for 1000 s = 200 nm T1 1 0 100 T2 2 0 100 T3 3 0 99 T4 4 0 97 T5 5 0 99 T6 6 0 98 T7 7 0 97 T8 8 0 100 T9 9 0 95 T10 10 0 99 T11 11 0 95 T12 12 0 97 T13 13 0 98 T14 14 0 100 T15 15 0 100 T16 16 0 95 T17 17 0 96 T18 18 0 99 T19 19 0 97 T20 20 0 97 T21 21 0 97 T22 22 0 95 T23 23 0 89 T24 24 0 100 T25 [2096506-54-4]-S1 0 100 ETM1 Magnesium, 10 A/s for 200 s = 200 nm T100 1 0 100 T101 2 0 100 T102 3 0 97 T103 12 0 95 T104 24 0 96 ETM2 Aluminium, 2 A/s for 1000 s = 200 nm T200 1 0 100 T201 [122048-53-7]-S1 0 99 T202 [2351281-21-3]-S4 0 97 ETM3 Aluminium, 2 A/s for 1000 s = 200 nm T300 [122048-53-7]-S19 0 97 T301 [1616514-34-1]-S2 0 100 ETM4 (50% by wt.)/ETM8 (50% by wt.) Aluminium, 2 A/s for 1000 s = 200 nm T400 3 0 99 T401 [1616514-39-6]-S2 0 98 T402 [910255-27-8]-S8 0 97 ETM5 (50% by wt.)/ETM8 (50% by wt.) Magnesium (10% by wt.)/silver (90% by wt.), 2 A/s for 1000 s = 200 nm T500 [1384281-78-0]-S14 0 97 T501 [1182175-15-0]-S12 0 93 ETM6 Magnesium, 2 A/s for 1000 s = 200 nm T600 [1314653-19-4]-S18 0 99 T601 [122048-53-7]-S2 0 98 ETM7 Silver, 2 A/s for 1000 s = 200 nm T700 [1384281-78-0]-S10 0 100 T701 [1616514-39-6]-S22 0 95

    [0255] The compounds [2096506-54-4]-S1, [122048-53-7]-S1, [2351281-21-3]-S4, [122048-53-7]-S19, [1616514-34-1]-S2, [1616514-39-6]-S2, [910255-27-8]-S8, [1384281-78-0]-S14, [1182175-15-0]-S12, [1314653-19-4]-S18, [122048-53-7]-S2, [1384281-78-0]-S10, [1616514-39-6]-S22 are obtained by reaction of the compounds having CAS numbers [2096506-54-4], [122048-53-7], [2351281-21-3], [122048-53-7], [1616514-34-1], [1616514-39-6], [910255-27-8], [1384281-78-0], [1182175-15-0], [1314653-19-4], [122048-53-7], [1384281-78-0], [1616514-39-6] etc. with the abovementioned synthons S1, S2, S4, S8, S10, S12, S14, S18, S22 analogously to the abovementioned procedure for preparing the compounds 1 to 24 in yields of about 50-90%, where the regiochemistry of the C—C coupling is unambiguously fixed by the position of the aryl bromide and arylboronic acid coupling partners. If the aryl bromides are di-, tri-, tetrabromides etc., the stoichiometry is adjusted correspondingly such that all Br functions react under C—C coupling.

    [0256] The expression “[2096506-54-4]-S1” represents the product that is obtained by reacting the compound CAS No. 2096506-54-4 with the aforementioned boronic ester S1. The same applies to the other products specified in the above table.

    TABLE-US-00005 TABLE 2 Structural formulae of the materials used [00232]embedded image ETM1 561064-11-7 [00233]embedded image ETM2 192198-85-9 [00234]embedded image ETM3 925425-96-3 [00235]embedded image ETM4 1201800-83-0 [00236]embedded image ETM5 1819335-36-8 [00237]embedded image ETM6 1685267-97-3 [00238]embedded image ETM7 1615703-29-1 [00239]embedded image ETM8 25387-93-3