Mixtures of organic emissive semiconductors and matrix materials, their use and electronic components comprising said materials

Abstract

The present invention relates to new types of material mixtures composed of at least two substances, one serving as a matrix material and the other being an emission material capable of emission and containing at least one element of atomic number greater than 20, and for their use in organic electronic components such as electroluminescent elements and displays.

1 - 21 . (canceled) 
     
     
         22 . A compound of the formula (40), (41a), (42) 
       
         
           
           
               
               
           
         
         where the symbols L, M, R 1 , R 3 , p and Z are each as defined as follows: 
         L is the same or different at each instance and is P, As, Sb or Bi; 
         M is the same or different at each instance and is S, Se or Te; 
         R 1  is the same or different at each instance and are each H, F, Cl, Br, I, CN, NO 2 , N(R 3 ) 2 , a straight-chain, branched or mono-, oligo- or polycyclic alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, in which one or more nonadjacent CH 2  groups may be replaced by —R 4 C═CR 4 —, Si(R 4 ) 2 , Ge(R 5 ) 2 , Sn(R 6 ) 2 , NR 7 , C═O, C═S, C═Se, C═NR 8 , —O—, —S—, —NR 9 — or —CONR 10 —, and in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , or an aromatic or heteroaromatic ring system having from 1 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , and which may be substituted by one or more nonaromatic R 3  radicals, where a plurality of substituents R 1  together may form a further mono- or polycyclic, aliphatic or aromatic ring system; 
         R 3  is the same or different at each instance and is a straight-chain or branched or mono-, oligo- or polycyclic alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, in which one or more nonadjacent CH 2  groups may be replaced by —R 4 C═CR 4 —, —C═C—, Si(R 4 ) 2 , Ge(R 5 ) 2 , Sn(R 6 ) 2 , NR 7 , C═O, C═S, C═Se, C═NR 8 , —O—, —S—, —NR 9 — or —CONR 10 —, and in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , or an aromatic or heteroaromatic ring system having from 1 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , and which may be substituted by one or morenonaromatic R 1  radicals, where a plurality of substituents R 1  together may form a further mono- or polycyclic, aliphatic or aromatic ring system, and where R 3  with R 1  may form a mono- or polycyclic, aliphatic or aromatic ring system; 
         R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  are the same or different at each instance and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms; 
         Z is the same or different at each instance and is CR 1  or N; and 
         p is the same or different at each instance and is 0 or 1; and 
         Ar is the same or different at each instance and is a mono- or bivalent, aromatic or heteroaromatic ring system having from 2 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, and which may be substituted by one or more nonaromatic R 1  radicals, and where a plurality of substituents R 1 , either on the same ring or on different rings, together may in turn form a further mono- or polycyclic, aliphatic or aromatic ring system. 
       
     
     
         23 . An electronic component comprising at least one compound as claimed in  claim 22 . 
     
     
         24 . The electronic component as claimed in  claim 23 , wherein the electronic component is an organic light-emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin-film transistor, an organic solar cell, an organic optical detector, an organic photoreceptor in electrophotography or an organic laser diode. 
     
     
         25 . The electronic component of  claim 23 , wherein the compound directly adjoins an electron transport layer without use of a separate hole blocking layer. 
     
     
         26 . The electronic component of  claim 23 , wherein the compound directly adjoins an electron injection layer or a cathode without use of a separate hole blocking layer and of a separate electron transport layer. 
     
     
         27 . The electronic component of  claim 23 , wherein the electronic component is an organic light-emitting diode which comprises at least one hole blocking layer and/or at least one electron transport layer and/or at least one electron injection layer and/or a further layer. 
     
     
         28 . A mixture comprising
 at least one matrix material A, comprising at least one compound of the formula (38) or (39),   
       
         
           
           
               
               
           
         
         where the symbols and indices are defined as follows: 
         o is from 5 to 5 000 000; 
         m is 1, 2, 3, 4, 5 or 6; 
         R 1  is the same or different at each instance and are each H, F, Cl, Br, I, CN, NO 2 , N(R 3 ) 2 , a straight-chain, branched or mono-, oligo- or polycyclic alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, in which one or more nonadjacent CH 2  groups may be replaced by —R 4 C═CR 4 —, Si(R 4 ) 2 , Ge(R 5 ) 2 , Sn(R 6 ) 2 , NR 7 , C═O, C═S, C═Se, C═NR 8 , —O—, —S—, —NR 9 — or —CONR 10 —, and in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , or an aromatic or heteroaromatic ring system having from 1 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , and which may be substituted by one or more nonaromatic R 3  radicals, where a plurality of substituents R 1  together may form a further mono- or polycyclic, aliphatic or aromatic ring system; 
         R 3  is the same or different at each instance and is a straight-chain or branched or mono-, oligo- or polycyclic alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms, in which one or more nonadjacent CH 2  groups may be replaced —R 4 C═CR 4 —, Si(R 4 ) 2 , Ge(R 5 ) 2 , Sn(R 6 ) 2 , NR 7 , C═O, C═S, C═Se, C═NR 8 , —O—, —S—, —NR 9 — or —CONR 10 —, and in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , or an aromatic or heteroaromatic ring system having from 1 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, CN, NO 2 , and which may be substituted by one or more nonaromatic R 1  radicals, where a plurality of substituents R 1  together may form a further mono- or polycyclic, aliphatic or aromatic ring system, and where R 3  with R 1  may form a mono- or polycyclic, aliphatic or aromatic ring system; 
         R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  are the same or different at each instance and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms, and 
         at least one emission material B which is capable of emission and is a compound which emits light upon suitable excitation and contains at least one element of atomic number greater than 20. 
       
     
     
         29 . The mixture of  claim 28 , comprising, as the emitter B, at least one compound, wherein the element of atomic number greater than 56 and less than 80 is molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium. 
     
     
         30 . The mixture of  claim 28 , comprising, as the emitter B, least one emission material B comprising at least one compound of the formula (49) to (52) 
       
         
           
           
               
               
           
         
         where the symbols used are: 
         DCy is the same or different at each instance and is a cyclic group which contains at least one nitrogen or phosphorus atom via which the cyclic group DCy is bonded to the metal and, further wherein the group DCy is optionally substituted with one or more substituents R 11 ; 
         CCy is the same or different at each instance and is a cyclic group which contains a carbon atom via which the cyclic group CCy is bonded to the metal and, further wherein the groups CCy is optionally substituted with one or more substituents R 11 ; wherein the DCy and CCy groups are bonded to one another via a covalent bond; 
         R 11  is the same or different at each instance and is H, F, Cl, Br, I, NO 2 , CN, a straight-chain, branched or cyclic alkyl or alkoxy group having from 1 to 40 carbon atoms, in which one or more nonadjacent CH 2  groups may be replaced by C═O, C═S, C═Se, C═NR 4 , —O—, —S—, —NR 5 — or —CONR 6 —, and in which one or more hydrogen atoms may be replaced by F, or an aromatic or heteroaromatic ring system which has from 4 to 14 carbon atoms and may be substituted by one or more nonaromatic R 11  radicals, in which a plurality of substituents R 11 , either on the same ring or on the two different rings, together may in turn form a further mono- or polycyclic ring system; 
         A is the same or different at each instance and is a bidentate chelating ligand; 
         R 4 , R 5  and R 6  are the same or different at each instance and is H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms. 
       
     
     
         31 . An electronic component comprising at least one mixture as claimed in  claim 28 . 
     
     
         32 . The electronic component of  claim 31 , wherein the electronic component is an organic light-emitting diode, an organic integrated circuit, an organic field effect transistor, an organic thin-film transistor, an organic solar cell, an organic optical detector, an organic photoreceptor in electrophotography or an organic laser diode. 
     
     
         33 . The electronic component of  claim 31 , wherein the mixture directly adjoins an electron transport layer without use of a separate hole blocking layer. 
     
     
         34 . The electronic component of  claim 31 , wherein the mixture directly adjoins an electron injection layer or a cathode without use of a separate hole blocking layer and of a separate electron transport layer. 
     
     
         35 . The electronic component of  claim 31 , wherein the electronic component is an organic light-emitting diode which comprises at least one hole blocking layer and/or at least one electron transport layer and/or at least one electron injection layer and/or further layer. 
     
     
         36 . The mixture of  claim 28 , wherein
 R 1  and R 3  are the same or different at each instance and are each CH 3 , CF 3 , —HC═CH— or an aromatic or heteroaromatic ring system having from 1 to 40 carbon atoms, in which one or more hydrogen atoms may be replaced by F, Cl, Br, I, and which may be substituted by one or more nonaromatic R 1  radicals, where a plurality of substituents R 1  together may form a further mono- or polycyclic, aliphatic or aromatic ring system, and where R 1  and R 3  may together form a mono- or polycyclic, aliphatic or aromatic ring system; and   m is 1, 2 or 3.