COMPOUNDS THAT CAN BE USED FOR STRUCTURING FUNCTIONAL LAYERS OF ORGANIC ELECTROLUMINESCENT DEVICES

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.-27. (canceled)

28. A method comprising structuring at least one functional layer of an organic electronic device, with a compound, characterized in that the compound comprises at least one fluorinated alkyl radical having at least two carbon atoms.

29. The method according to claim 28, characterized in that the fluorinated alkyl radical comprises at least 2 fluorine atoms.

30. The method according to claim 28, characterized in that the fluorinated alkyl radical has a numerical ratio of fluorine atoms to carbon atoms of at least 0.5.

31. The method according to claim 28, characterized in that the fluorinated alkyl radical has a block structure where some of the carbon atoms have bonds to at least two hydrogen atoms and some of carbon atoms have bonds to at least two fluorine atoms, where the fluorinated alkyl radical has a structure of the formulae FA-1 to FA-16 ##STR00165## where the dotted line represents the site of attachment of the fluorinated alkyl radical, and in addition: A is a group of the formula —(C.sub.xH.sub.2x)—, —(C.sub.xH.sub.xD.sub.x)—, —(C.sub.xD.sub.2x)—, where x is an integer in the range from 1 to 6 where A is; B is a group of the formula —(C.sub.yF.sub.2y)—, —(C.sub.yF.sub.yH.sub.y)—, —(C.sub.yF.sub.yD.sub.y)—, where y is an integer in the range from 1 to 6; E is selected from H, D or F, preferably F; a is an integer in the range from 1 to 6; b is an integer in the range from 1 to 6; where the structures of the formulae (FA-9) to (FA-16) may form a ring, and are connected at two sites to further groups in the compound.

32. The method according to claim 28, characterized in that the compound comprises at least one structuring element of the formula (SE-I), (SE-II) and/or (SE-III) ##STR00166## where the FA group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, the dotted bond represents the bonding site, and in addition: 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 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 form a ring system with one another or a further group; 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 bridge by 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 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 bridge by 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.

33. The method according to claim 32, characterized in that the FA group of the structuring element of formula (SE-I), (SE-II) and/or (SE-III) comprises, at least one of the structures of the formulae (FA-1) to (FA-16) ##STR00167## where the dotted line represents the site of attachment of the fluorinated alkyl radical, and in addition: A is a group of the formula —(C.sub.xH.sub.2x)—, —(C.sub.xH.sub.xD.sub.x)—, —(C.sub.xD.sub.2x)—, where x is an integer in the range from 1 to 6; B is a group of the formula —(C.sub.yF.sub.2y)—, —(C.sub.yF.sub.yH.sub.y)—, —(C.sub.yF.sub.yD.sub.y)—, where y is an integer in the range from 1 to 6; E is selected from H, D or F, preferably F; a is an integer in the range from 1 to 6 b is an integer in the range from 1 to 6 where the structures of the formulae (FA-9) to (FA-16) may form a ring, and are connected at two sites to further groups in the compound.

34. The method according to claim 32, characterized in that the structuring element of the formula (SE-I), (SE-II) and/or (SE-III) can be represented by a formula (SE-1) to (SE-21) ##STR00168## ##STR00169## ##STR00170## ##STR00171## where the symbol X has the definition given in claim 32, and the further symbols are as follows: E is selected from H, D or F; Y.sup.1 is the same or different at each instance and is a bond, O, S, NR.sup.3 or C(═O); 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 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, the R.sup.3 radical may form a ring system together with an adjacent R or R.sup.1 radical, where the R.sup.2 and Ar″ radicals have the definition given in claim 32; the index a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index c is 2, 3, 4, 5, 6, 7, 8, 9 or 10; the index x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

35. The method according to claim 32, characterized in that the structuring element of the formula (SE-I), (SE-II) and/or (SE-III) can be represented by a formula (SE-1a) to (SE-21a) ##STR00172## ##STR00173## ##STR00174## ##STR00175## where the symbols are as follows: 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 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 form a ring system with one another or a further group; E is selected from H, D or F; Y.sup.1 is the same or different at each instance and is a bond, O, S, NR.sup.3 or C(═O), the index a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index c is 2, 3, 4, 5, 6, 7, 8, 9 or 10; the index x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; the index y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4; v is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4.

36. The method according to claim 28, characterized in that the compound comprises at least one aromatic or heteroaromatic ring system having at least two fused aromatic or heteroaromatic rings.

37. The method according to claim 36, 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) ##STR00176## ##STR00177## ##STR00178## 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 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 form a ring system with one another or a further group, for example with one or more of the R or R.sup.1 radicals, where the symbols R.sup.1 and Ar′ are defined as follows: 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 bridge by 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.

38. A compound comprising at least one structure of the formula (I), suitable for the method according to claim 28, ##STR00179## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, and the symbols are as follows: 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′, 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′, 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 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 form a ring system with one another or a further group; 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, aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, where the symbol 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; 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′, 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 each case be 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 form a ring system with one another or a further group, for example with one or more of the R.sup.c radicals, where the symbols R.sup.1 and Ar′ are defined as follows: 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 bridge by 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; 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 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, 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 form a ring system with one another or a further group, for example with one or more of the R.sup.b radicals, where the symbols R.sup.1 and Ar′ are defined as follows: 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 bridge by 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.

39. A compound comprising at least one structure of the formula (I-1) to (I-7), suitable for the method according to claim 28, ##STR00180## 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, 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 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—, 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; E is selected from H, D or F; Y.sup.2 is the same or different at each instance and is a bond, O, S, NR.sup.4 or C(═O); R.sup.4 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, the R.sup.4 radical may form a ring system with a further part of the compound, where the symbol 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, adjacent substituents R.sup.2 together may form a ring system; a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; c is 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 2, 3, 4, 5 or 6; x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

40. A compound comprising at least one structure of the formula (II), preferably a compound of formula (II), suitable for the method according to claim 28, ##STR00181## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, where the symbols are as follows: 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 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 form a ring system with one another or a further group; 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, 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 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.

41. A compound comprising at least one structure of the formulae (II-1) to (II-7), suitable for the method according to claim 28, ##STR00182## 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, 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 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; E is selected from H, D or F; Y.sup.2 is the same or different at each instance and is a bond, O, S, NR.sup.4 or C(═O); a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; c is 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 2, 3, 4, 5 or 6; x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

42. A compound comprising at least one structure of the formula (III), suitable for the method according to claim 28, ##STR00183## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, where the symbols are as follows: 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 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, 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 form a ring system with one another or a further group; L.sup.2 is a linking group, 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 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; 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.

43. A compound comprising at least one structure of the formulae (III-1) to (III-7), suitable for the method according to claim 28, ##STR00184## ##STR00185## where the symbols are as follows: L.sup.2 is a linking group, 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 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; 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; E is selected from H, D or F; Y.sup.2 is the same or different at each instance and is a bond, O, S, NR.sup.4 or C(═O); a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; c is 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 2, 3, 4, 5 or 6; x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

44. A compound comprising at least one structure of the formula (IV), suitable for the method according to claim 28, ##STR00186## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, where the symbols are as follows: 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 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 form a ring system with one another or a further group; L.sup.2 is a linking group, 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 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; 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.

45. A compound comprising at least one structure of the formulae (IV-1) to (IV-7), suitable for the method according to claim 28, ##STR00187## ##STR00188## where the symbols are as follows: L.sup.2 is a linking group, 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 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; 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; E is selected from H, D or F, H or F; Y.sup.2 is the same or different at each instance and is a bond, O, S, NR.sup.4 or C(═O); a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; c is 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 2, 3, 4, 5 or 6; x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

46. A compound comprising at least one structure of the formula (V), preferably a compound of formula (V), suitable for use according to claim 28, ##STR00189## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, but is preferably unsubstituted, where the symbols are as follows: 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 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 form a ring system with one another or a further group; L.sup.2 is a linking group, 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 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; 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.

47. A compound comprising at least one structure of the formulae (V-1) to (V-7), suitable for the method according to claim 28, ##STR00190## ##STR00191## where the symbols are as follows: L.sup.2 is a linking group, 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 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).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; 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; E is selected from H, D or F; Y.sup.2 is the same or different at each instance and is a bond, O, S, NR.sup.4 or C(═O); a is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; b is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; c is 2, 3, 4, 5, 6, 7, 8, 9 or 10; x is the same or different at each instance and is 1, 2, 3, 4, 5 or 6; y is the same or different at each instance and is 1, 2, 3, 4, 5 or 6.

48. A compound comprising at least one structure of the formula (VI), suitable for use according to claim 28, ##STR00192## where the FA′ group is a fluorinated alkyl radical which has at least two carbon atoms and may be substituted by one or more R radicals, where the symbols are as follows: 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 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 form a ring system with one another or a further group; L.sup.2 is a linking group, 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 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; 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.

Description

WORKING EXAMPLES

[0259] 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.

Synthesis of the Compounds

Example 1

[0260] ##STR00084##

[0261] A mixture of 32.2 g (100 mmol) of 4,4,5,5-tetramethyl-2-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]-1,3,2-dioxaborolane [2088974-50-7] (boronic ester 51), 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: 30.6 g (68 mmol), 68%; purity: >99.5% by HPLC.

[0262] The following compounds can be prepared analogously:

TABLE-US-00002 Ex.. Reactants Product Yield  2 [00085] [00086] 60% [00087]  3 [00088] [00089] 63% [00090]  4 [00091] [00092] 49% [00093]  5 [00094] [00095] 70% [00096]  6 [00097] [00098] 58% [00099]  7 [00100] [00101] 65% [00102]  8 [00103] [00104] 66% [00105]  9 [00106] [00107] 71% [00108] 10 [00109] [00110] 70% [00111] 11 [00112] [00113] 61% [00114] 12 [00115] [00116] 76% [00117] 13 [00118] [00119] 73% [00120] 14 [00121] [00122] 69% [00123] 15 [00124] [00125] 66% [00126] 16 [00127] [00128] 58% [00129] 17 [00130] [00131] 54% [00132] 18 [00133] [00134] 75% [00135] 19 [00136] [00137] 68% [00138] 20 [00139] [00140] 63% [00141] 21 [00142] [00143] 65% [00144] 22 [00145] [00146] 68% [00147] 23 [00148] [00149] 63% [00150] 24 [00151] [00152] 76% [00153]

Structuring of Metal Layers:

[0263] The examples that follow present the results for structuring of metals and metal mixtures (alloys).

[0264] 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%).

[0265] 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 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.

[0266] 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 (for thickness see table). 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.

[0267] 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.

[0268] 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-00003 TABLE 1 Compound of Transmittance Transmittance the invention [%] [%] Ex. Thickness Region 2 Region 4 ETM1 Magnesium, 2 A/s for 1000 s = 200 nm TRef.1 Ref.1/30 nm 0 98 TRef.2 Ref.2/30 nm 0 98 TRef.3 Ref.3/30 nm 0 99 TRef.4 Ref.1/10 nm 0 45 TRef.5 Ref.2/10 nm 0 67 TRef.6 Ref.3/10 nm 0 51 T1 1/30 nm 0 97 T2 2/30 nm 0 98 T3 3/30 nm 0 100 T4 1/10 nm 0 90 T5 2/10 nm 0 92 T6 3/10 nm 0 99 ETM1 Magnesium, 10 A/s for 200 s = 200 nm TRef.1 Ref.1/30 nm 0 8 TRef.2 Ref.2/30 nm 0 55 TRef.3 Ref.3/30 nm 0 38 T100 1/30 nm 0 88 T101 2/30 nm 0 96 T102 3/30 nm 0 99 T103 4/30 nm 0 95 T104 5/30 nm 0 97 T105 6/30 nm 0 98 T106 7/30 nm 0 94 T107 8/30 nm 0 96 T108 9/30 nm 0 95 T109 10/30 nm  0 95 T110 11/30 nm  0 99 T111 12/30 nm  0 96 T112 13/30 nm  0 95 T113 14/30 nm  0 94 T114 15/20 nm  0 97 T115 16/30 nm  0 100 T116 17/30 nm  0 100 T117 18/30 nm  0 100 T118 19/30 nm  0 96 T119 20/20 nm  0 97 T120 21/30 nm  0 92 T121 22/30 nm  0 94 T122 23/30 nm  0 93 T123 24/20 nm  0 100 ETM2 Aluminium, 10 A/s for 200 s = 200 nm T200 13/30 nm  0 96 T201 [1616514-34-1]- 0 97 S6/30 nm T202 [2351281-21-3]- 0 95 S12/30 nm ETM3 Aluminium, 10 A/s for 200 s = 200 nm T300 [1062556-32-4]- 0 96 S2/20 nm T301 [400607-04-7]- 0 99 S7/20 nm ETM4 (50% by wt.)/ETM8 (50% by wt.) Aluminium, 10 A/s for 200 s = 200 nm T400 3/20 nm 0 99 T401 [845457-53-6]- 0 97 S8/20 nm T402 [1182175-15-0]- 0 96 S12/20 nm 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 [944801-21-2]- 0 90 S3/10 nm T501 [1273319-86-0]- 0 92 S13/10 nm ETM6 Magnesium, 10 A/s for 200 s = 200 nm T600 [15810-15-8]- 0 97 S14/30 nm T601 [1732-26-9]- 0 98 S16/30 nm ETM7 Silver, 10 A/s for 200 s = 200 nm T700 [1714-29-0]- 0 94 S19/15 nm T701 [109465-97-6]- 0 91 S15/10 nm

[0269] Compounds [1616514-34-1]-S6, [2351281-21-3]-S12, [1062556-32-4]-S2, [400607-04-7]-S7, [845457-53-6]-S8, [1182175-15-0]-S12, [944801-21-2]-S3, [1273319-86-0]-S13, [15810-15-8]-S14, [1732-26-9]-S16, [1714-29-0]-S19, [109465-97-6]-S15 are obtained in yields of about 50-90% by reacting the compounds having CAS numbers [1616514-34-1], [2351281-21-3], [1062556-32-4], [400607-04-7], [845457-53-6], [1182175-15-0], [944801-21-2], [1273319-86-0], [15810-15-8], [1732-26-9], [1714-29-0], [109465-97-6], etc. with the above-detailed synthons S2, S3, S6, S7, S8, S12, S13, S14, S15, S16, S19 etc., and analogously to the above-detailed method of preparing compounds 1 to 24, where the regiochemistry of the C—C coupling is fixed unambiguously by the position of the aryl bromide and arylboronic acid coupling partners.

[0270] If the aryl bromides are di-, tri-, tetrabromides etc., the stoichiometry is adjusted correspondingly such that all Br functions react under C—C coupling.

[0271] The expression [1616514-341]-S6″ represents the product that is obtained by reacting compound CAS No. 1616514-341 with the aforementioned boronic ester S6. The same applies to the other products specified in the above table.

TABLE-US-00004 TABLE 2 Structural formulae of the materials used [00154] [00155] [00156] [00157] [00158] [00159] [00160] [00161] [00162] [00163] [00164]