Materials for electronic devices

Abstract

The present application relates to a material comprising a monoarylamine of a defined formula and a p-dopant of a defined formula. The present application further relates to the use of said material in an organic layer of an electronic device, the device preferably being an organic electroluminescent device (OLED).

1 - 21 . (canceled) 
     
     
         22 . A material comprising a compound P which is a complex of bismuth and a compound A of a formula (A-I), (A-IV), (A-V), (A-VII) or (A-IX) 
       
         
           
           
               
               
           
         
         where one or more R 1  radicals may be bonded to any of the unsubstituted positions shown, and the variables that occur are as follows: 
         Z is the same or different at each instance and is CR 1 ; 
         X is the same or different at each instance and is a single bond, O, S, C(R 1 ) 2 , Si(R 1 ) 2 , PR 1 , C(R 1 ) 2 —C(R 1 ) 2 , or CR 1 ═CR 1 ; 
         Y is the same or different at each instance and is O, S, C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , C(R 1 ) 2 —C(R 1 ) 2 , or CR 1 ═CR 1 ; 
         Ar 1  is the same or different at each instance and is an aromatic ring system which has 6 to 60 aromatic ring atoms and may be substituted by one or more R 1  radicals, or a heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1  radicals; 
         Ar 2  is an aromatic ring system which has 6 to 20 aromatic ring atoms and may be substituted by one or more R 1  radicals, or a heteroaromatic ring system which has 5 to 20 aromatic ring atoms and may be substituted by one or more R 1  radicals; 
         n, p, q are the same or different and are each 0 or 1; where the sum of the value of the indices p and q is 1; 
         R 1  is the same or different at each instance and is selected from H, D, F, C(═O)R 2 , CN, Si(R 2 ) 3 , P(═O)(R 2 ) 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , 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 having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned may each be substituted by one or more R 2  radicals; and where one or more CH 2  groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, P(═O)(R 2 ), —O—, —S—, SO or SO 2 ; 
         R 2  is the same or different at each instance and is selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; and where the alkyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by F or CN. 
       
     
     
         23 . The material according to  claim 22 , wherein the compound A has a single amino group. 
     
     
         24 . The material according to  claim 22 , wherein the compound A does not contain a fused aryl group having more than 10 aromatic ring atoms nor a fused heteroaryl group having more than 14 aromatic ring atoms. 
     
     
         25 . The material according to  claim 22 , wherein in the compound A, the Ar 1  group is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and may be substituted by one or more R 1  radicals, or a heteroaromatic ring system which has 5 to 40 ring atoms and may be substituted by one or more R 1  radicals. 
     
     
         26 . The material according to  claim 22 , wherein, in the compound A, the Ar 1  group is a group which is optionally substituted by one or more R 1  radicals and is selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluoranthenyl, fluorenyl, indenofluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridyl and phenanthridyl. 
     
     
         27 . The material according to  claim 22 , wherein in the compound A, group X is the same or different at each instance and is a single bond or O. 
     
     
         28 . The material according to  claim 22 , wherein in the compound A, group Y is C(R 1 ) 2 . 
     
     
         29 . The material according to  claim 22 , wherein the compound A conforms to a formula (A-I), and groups Ar 1  are selected, identically or differently, from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl, each of which is optionally substituted by one or more R 1  radicals. 
     
     
         30 . The material according to  claim 22 , wherein the compound A conforms to a formula (A-IV), and one of groups X is a single bond, and the other one of groups X is O. 
     
     
         31 . The material according to  claim 22 , wherein the compound A conforms to a formula (A-V), and group X is a single bond. 
     
     
         32 . The material according to  claim 22 , wherein groups Ar 1  are selected, identically or differently, from the following groups 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         each of which may be substituted by one or more R 1  radicals at any of the unsubstituted positions shown. 
       
     
     
         33 . The material according to  claim 22 , wherein groups Ar 2  are selected, identically or differently, from the following groups 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         each of which may be substituted by one or more R 1  radicals at any of the unsubstituted positions shown. 
       
     
     
         34 . The material according to one  claim 22 , wherein the compound P is a complex of bismuth in the (III) oxidation state. 
     
     
         35 . The material according to  claim 22 , wherein the compound P is a complex of bismuth having at least one ligand L which is an organic compound. 
     
     
         36 . The material according to  claim 35 , wherein the ligand L is singly negatively charged. 
     
     
         37 . The material according to  claim 35 , wherein the group in the ligand L that binds to the bismuth atom is selected from carboxylic acid groups, thiocarboxylic acid groups, carboxamide groups and carboximide groups. 
     
     
         38 . The material according to  claim 35 , wherein the ligand L is selected from fluorinated benzoic acid derivatives, fluorinated or non-fluorinated phenylacetic acid derivatives and fluorinated or non-fluorinated acetic acid derivatives. 
     
     
         39 . The material according to  claim 22 , wherein the compound P is present in the material as a dopant in a concentration of 0.1% to 20%. 
     
     
         40 . A layer comprising the material according to  claim 22 . 
     
     
         41 . A formulation comprising the material according to  claim 22  and at least one solvent. 
     
     
         42 . A process for producing the layer according to  claim 40 , wherein compound A and compound P are applied together from the gas phase, or in that a formulation comprising the material of the invention is applied from the liquid phase. 
     
     
         44 . Electronic device selected from organic electroluminescent devices, 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 and organic laser diodes, comprising the material according to  claim 22 . 
     
     
         45 . An organic electroluminescent device comprising the material according to  claim 22 , wherein the device includes the material in a hole-transporting layer disposed between anode and emitting layer, with one or more further layers present between the layer comprising the material and the emitting layer. 
     
     
         46 . The organic electroluminescent device according to  claim 45 , wherein the HOMO levels of the hole-transporting layer (HTL) and the one layer between hole-transporting layer and emitting layer (EBL) meet the following condition:
   HOMO(HTL)<=HOMO(EBL).   
     
     
         47 . The organic electroluminescent device according to  claim 45 , wherein the one or more further layers disposed between the layer comprising the material and the emitting layer comprise one or more identical or different compounds of the formula (A). 
     
     
         48 . The organic electroluminescent device according to  claim 45 , wherein the device comprises the material in a layer directly adjoining the anode.