Materials for electronic devices

Abstract

The invention relates to phenanthrene compounds comprising one or more arylamino groups. Said compounds can be used in electronic devices, in particular OLED's.

1 .- 20 . (canceled) 
     
     
         21 . A compound of one of formulae (I-3) to (I-8) 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where the symbols that occur are as follows: 
       
       R‘ R’ is the same or different at each instance and is selected from H, D, F, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals, where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may each be substituted by one or more R 6  radicals and
 where one or more CH 2  groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 6 C═CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ; 
 R 2 , R 3  are the same or different at each instance and are selected from H, D, F, C(═O)R 6 , CN, Si(R 6 ) 3 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals,
 where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may each be substituted by one or more R 6  radicals, and 
 where one or more CH 2  groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by 
 —R 6 C—CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 ; 
 
 R 6  is the same or different at each instance and is selected from H, D, F, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 7  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 7  radicals,
 where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may each be substituted by one or more R 7  radicals, 
 where one or more CH 2  groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by 
 —R 7 C—CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 , and 
 where two or more R 6  substituents may be joined to one another and may form a ring; 
 
 R 7  is the same or different at each instance and is selected from H, D, F, CN and aliphatic, aromatic or heteroaromatic organic radicals having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D, F or CN; 
 Ar 1  is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 4  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 4  radicals; 
 Ar 2  is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 4  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 4  radicals; 
 R 4  is the same or different at each instance and is selected from H, D, F, C(═O)R 6 , CN, Si(R 6 ) 3 , N(R 6 ) 2 , P(═O)(R 6 ) 2 , OR 6 , S(═O)R 6 , S(═O) 2 R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems which have 6 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may be substituted by one or more R 6  radicals,
 where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may each be substituted by one or more R 6  radicals, 
 where one or more CH 2  groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by 
 —R 6 C—CR 6 —, —C≡C—, Si(R 6 ) 2 , C═O, C═NR 6 , —C(═O)O—, —C(═O)NR 6 —, NR 6 , P(═O)(R 6 ), —O—, —S—, SO or SO 2 , and 
 where two or more R 4  substituents may be joined to one another and may form a ring; 
 
 
     
     
         22 . The compound as claimed in  claim 21 , wherein Ar 1  is the same or different at each instance and is selected from aromatic ring systems which have 12 to 24 aromatic ring atoms and optionally substituted by one or more R 4  radicals. 
     
     
         23 . The compound as claimed in  claim 21 , wherein two Ar 1  groups bonded to the same nitrogen atom are not the same. 
     
     
         24 . The compound as claimed in  claim 21 , wherein the Ar 1  groups each contain at least one group selected from benzene, naphthalene, phenanthrene, fluoranthene, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzimidazole, pyrimidine, pyrazine or triazine, each optionally substituted by one or more R 4  radicals. 
     
     
         25 . The compound as claimed in  claim 21 , wherein Ar 2  is the same or different at each instance and is selected from aromatic ring systems which have 6 to 13 aromatic ring atoms and optionally substituted by one or more R 4  radicals. 
     
     
         26 . The compound as claimed in  claim 21 , wherein R 4  are the same or different at each instance and are selected from H, D, F, CN, Si(R 6 ) 3 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems which have 6 to 24 aromatic ring atoms and optionally substituted by one or more R 6  radicals, and heteroaromatic ring systems which have 5 to 24 aromatic ring atoms and optionally substituted by one or more R 6  radicals,
 where the alkyl and alkoxy groups mentioned may each be substituted by one or more R 6  radicals and where one or more CH 2  groups in the alkyl and alkoxy groups mentioned may be replaced by —C≡C—, —R 6 C—CR 6 —, Si(R 6 ) 2 , C═O, C═NR 6 , —NR 6 —, —O—, —S—, —C(═O)O— or —C(═O)NR 6 —.   
     
     
         27 . The compound as claimed in  claim 21 , wherein R 6  is the same or different at each instance and is selected from H, D, F, CN, Si(R 7 ) 3 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems which have 6 to 24 aromatic ring atoms and optionally substituted by one or more R 7  radicals, and heteroaromatic ring systems which have 5 to 24 aromatic ring atoms and optionally substituted by one or more R 7  radicals,
 where the alkyl and alkoxy groups mentioned may each be substituted by one or more R 7  radicals and where one or more CH 2  groups in the alkyl and alkoxy groups mentioned may be replaced by —C≡C—, —R 7 C—CR 7 —, Si(R 7 ) 2 , C═O, C═NR 7 , —NR 7 —, —O—, —S—, —C(═O)O— or —C(═O)NR 7 —.   
     
     
         28 . A process for preparing the compound as claimed in  claim 21 , wherein a phenanthrene compound substituted by a leaving group in the 1 and/or 4 position is reacted in a coupling reaction with a diarylamino compound or with a triarylamino compound substituted by a leaving group. 
     
     
         29 . An oligomer, polymer or dendrimer containing one or more compounds as claimed in  claim 21 , wherein the bond(s) to the polymer, oligomer or dendrimer may be localized at any desired positions substituted by R 1 , R 2 , R 3 , R 4 , R 6  or R 7  in formulae (I-3) to (I-8). 
     
     
         30 . A formulation comprising at least one compound as claimed in  claim 21 , and at least one solvent. 
     
     
         31 . An electronic device selected from the group consisting of 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, organic light-emitting electrochemical cells, organic laser diodes and organic electroluminescent devices, comprising at least one compound as claimed in  claim 21 . 
     
     
         32 . The electronic device as claimed in  claim 31 , wherein the device is an organic electroluminescent devices comprising cathode, anode and at least one organic layer comprising at least one compound as claimed in  claim 21 . 
     
     
         33 . The electronic device as claimed in  claim 32 , wherein the compound is present as hole transport material in a hole transport layer, an electron blocker layer or a hole injection layer, or as an emitting compound in an emitting layer, or as matrix compound together with one or more emitting compounds in an emitting layer.