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

• US 9,718,764 B2
• Filed: 02/24/2014
• Issued: 08/01/2017
• Est. Priority Date: 03/22/2013
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Stoessel, Philipp, Parham, Amir Hossain, Jatsch, Anja
• Primary Examiner(s): Jackson, Shawquia
• Application Number:
  US14/778,783
• Publication Number:
  US 20160046563A1
• Time in Patent Office: 1,254 Days
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C07C 253/14 by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
• CPC Class Codes: C07C 253/20 by dehydration of carboxylic acid amides
• CPC Class Codes: C07C 253/30 by reactions not involving the formation of cyano groups
• CPC Class Codes: C07C 255/51 containing at least two cyano groups bound to the carbon skeleton
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2602/10 the other ring being six-membered, e.g. tetraline
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 2603/24 Anthracenes; Hydrogenated anthracenes
• CPC Class Codes: C07C 2603/26 Phenanthrenes; Hydrogenated phenanthrenes
• CPC Class Codes: C07C 2603/42 containing only six-membered rings
• CPC Class Codes: C07C 2603/97 containing five-membered rings
• CPC Class Codes: C07C 51/16 by oxidation C07C51/145 takes precedence
• CPC Class Codes: C07C 51/60 by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
• CPC Class Codes: C07D 209/80 [b, c]- or [b, d]-condensed
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 235/18 with aryl radicals directly attached in position 2
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C07D 307/91 : Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 : Dibenzothiophenes
• CPC Class Codes: C07D 403/10 : linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems

Abstract

The present invention relates to compounds which are suitable as synthesis precursors for the production of electronically active materials for use in organic electroluminescence devices.

Claims

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

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),

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

6. The compound according to claim 1, wherein R is selected on each occurrence, identically or differently, from the group consisting of H, NAr₂, C(═

O)Ar, C(═

O)R¹, P(═

O)Ar₂, PAr₂, Si(R¹)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 R¹, where in each case one or more non-adjacent CH₂ groups may be replaced by R¹C═

CR¹ 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 R¹;

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 R¹.

7. The compound according to claim 1, wherein none of the radicals R, R¹ or R² 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 R¹.

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 R¹, or at least one substituent R stands for —

NAr₂, where the two groups Ar may also be bridged to one another by a group selected from NR¹, O, S, C(R¹)₂, Si(R¹)₂ or BR¹.

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 R¹.

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 R¹, or in that at least one substituent R is selected from one of the groups of the formulae (7) to (18)

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),