Synthetic building blocks for the production of materials for organic electroluminescence devices

1. A compound of the formula (1), formula (2) or formula (3),

where the following applies to the symbols and indices used:

L stands for a single bond, NR, BR, P(═O)R, a straight-chain alkylene or alkylidene group having 1 to 10 C atoms or a branched or cyclic alkylene or alkylidene group having 3 to 10 C atoms, which may be substituted by in each case substituted by one or more radicals R, where one or more non-adjacent CH 2 groups may be replaced by —RC═CR—, —C≡C—, Si(R) 2 , C═O, —O—, —S— or —CONR— and where one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R;

R is selected on each occurrence, identically or differently, from the group consisting of H, D, Cl, Br, I, NAr 2 , N(R 1 ) 2 , where R 1 is not equal to H, C(═O)Ar, C(═O)R 1 , BR 1 , P(═O)Ar 2 , PAr 2 , OAr, SAr, S(═O)Ar, S(═O) 2 Ar, Si(R 1 ) 3 , a straight-chain alkyl or alkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 1 , where in each case one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═NR 1 , P(═O)(R 1 ), NR 1 , O, S or CONR 1 and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 ; two or more adjacent substituents R here may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R 1 ;

Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; two radicals Ar here which are bonded to the same N atom or P atom may also be bridged to one another by a single bond or a bridge selected from N(R 1 ), C(R 1 ) 2 , O, S or BR 1 ;

R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(R 2 ) 2 , P(═O)(R 2 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms may be replaced by D, F, Cl, Br, I or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ; two or more adjacent substituents R 1 here may optionally form a monocyclic or polycyclic, aliphatic ring system, which may be substituted by one or more radicals R 2 ;

R 2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R 2 may form a mono- or polycyclic, aliphatic ring system with one another;

n is 0, 1, 2, 3, 4 or 5, with the proviso that L is not present if n=0 and furthermore with the proviso that, for n≧1, L is in each case bonded to the benzene skeleton instead of a radical R and the corresponding group R is thus not present;

with the proviso that the following compounds are excluded from the invention:

2. The compound according to claim 1 , wherein n=0, 1, 2 or 3.

3. The compound according to claim 1 , wherein n=0, 1 or 2.

4. The compound according to claim 1 , selected from the compounds of the formulae (1a) to (1h), (2a) to (2l) and (3a) to (3f),

where the symbols used has the meanings given in claim 1 .

5. The compound according to claim 1 , wherein two adjacent radicals R form a ring of the formula (4) with one another,

where R 1 has the meanings given above, the dashed bonds indicate the linking of the group to the benzene skeleton and furthermore:

E is selected from the group consisting of C(R 1 ) 2 , NR 1 , O, S, BR 1 or Si(R 1 ) 2 .

6. The compound according to claim 1 , wherein R is selected on each occurrence, identically or differently, from the group consisting of H, NAr 2 , C(═O)Ar, C(═O)R 1 , P(═O)Ar 2 , PAr 2 , Si(R 1 ) 3 , a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, each of which may be substituted by one or more radicals R 1 , where in each case one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 or O and where one or more H atoms may be replaced by F, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 ; two or more adjacent substituents R here may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R 1 .

7. The compound according to claim 1 , wherein none of the radicals R, R 1 or R 2 contains condensed aryl or heteroaryl groups in which six-membered rings are condensed directly onto one another.

8. The compound according to claim 1 , wherein at least one radical R is selected from the group consisting of an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 1 .

9. The compound according to claim 1 , wherein at least one radical R is selected from the group consisting of triarylamine, carbazole, indenocarbazole, indolocarbazole, azacarbazole, indole, furan, benzofuran, dibenzofuran, thiophene, benzothiophene or dibenzothiophene, each of which may be substituted by one or more radicals R 1 , or at least one substituent R stands for —NAr 2 , where the two groups Ar may also be bridged to one another by a group selected from NR 1 , O, S, C(R 1 ) 2 , Si(R 1 ) 2 or BR 1 .

10. A process for the preparation of the compound according to claim 1 , comprising the reaction steps:

a) oxidation of a fluoro-meta-xylene to give the carboxylic acid; and

b) conversion of the carboxylic acid functionalities into nitrile groups.

11. A process for the preparation of a compound according to claim 1 which comprises reacting a fluoro-meta-dihalobenzene with Zn(CN) 2 and Zn in the presence of a catalyst.

12. A starting material in a nucleophilic aromatic substitution reaction which comprises the compound according to claim 1 .

13. The compound according to claim 1 , wherein at least one radical R is selected from the group consisting of benzene, biphenyl, terphenyl, quaterphenyl, 1-spirobifluorene, 2-spirobifluorene, 3-spirobifluorene, 4-spirobifluorene, 1-fluorene, 2-fluorene, 3-fluorene, 4-fluorene, 1-naphthyl, 2-naphthyl, pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazole, benzimidazole, pyrazole, thiazole, oxazole, oxadiazole, triazole, phenanthrene, triphenylene or combinations of two or three of these groups, each of which may be substituted by one or more radicals R 1 .

14. The compound according to claim 1 , wherein at least one radical R is selected from the group consisting of benzene, ortho-biphenyl, meta-biphenyl, para-biphenyl, ortho-terphenyl, meta-terphenyl, para-terphenyl, branched terphenyl, ortho-quaterphenyl, meta-quaterphenyl, para-quaterphenyl, branched quaterphenyl, 1-spirobifluorene, 2-spirobifluorene, 3-spirobifluorene, 4-spirobifluorene, 1-fluorene, 2-fluorene, 3-fluorene, 4-fluorene, 1-naphthyl, 2-naphthyl, pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazole, benzimidazole, pyrazole, thiazole, oxazole, oxadiazole, triazole, phenanthrene, triphenylene or combinations of two or three of these groups, each of which is optionally substituted by one or more radicals R 1 , or in that at least one substituent R is selected from one of the groups of the formulae (7) to (18)

where the symbols used have the meanings given in claim 1 , * indicates the position of the bonding of the group and furthermore:

A is on each occurrence, identically or differently, CR 1 or N, with the proviso that one, two or three groups A stand for N;

Ar 1 is, identically or differently on each occurrence, a divalent aromatic or heteroaromatic ring system having 5 to 16 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;

m is 0 or 1.

15. The compound according to claim 1 , wherein at least one radical R is selected from the group consisting of the formulae (19) to (33),

where the symbols used have the meanings given in claim 1 and furthermore:

G is selected from the group consisting of NR 1 , O or S;

where in each case one or two groups CR 1 may be replaced by N.