Materials for electronic devices

Abstract

The invention relates to compounds comprising functional substituents in a specific spatial arrangement, devices containing same, and the preparation and use thereof.

1 .- 21 . (canceled) 
     
     
         22 . A compound of the general formula (1) 
       
         
           
           
               
               
           
         
         where the symbols and indices used are as follows: 
         A and A′ are the same or different and are an aromatic or heteroaromatic ring which has 5 or 6 ring atoms and is optionally substituted by one or more R 1  radicals which is optionally independent of one another; 
         G 1  is an organic electron-transporting group (ETG) of the formula E-9 or E-10 
       
       
         
           
           
               
               
           
         
         Q′ is the same or different at each instance and is CR 1  or N, and
 where the dotted bond indicates the binding positions to the Ar 1  group or carbon atom of the A group; 
 
         G 2  is an electron-rich organic group selected from the a group of the formula (L-18)-(L-30) and L(34)-L(36): 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where dotted bonds indicate the binding positions to the Ar 2  group or carbon atom of the A′ group, which may be substituted by one or more independent R 2  radicals; 
         Ar 1  is a bivalent aromatic ring or ring system having 6 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the ETG; 
         Ar 2  is, when G 2  is an electron-transporting group, a bivalent aromatic ring or ring system having 6 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the ETG,
 or, when G 2  is a hole-transporting group, an aromatic ring or ring system having 5 to 60 ring atoms, where the ring or ring system is bridged neither with the ring system comprising the A and A′ rings nor with the LTG; 
 
         V is O; 
         W is a single bond, C═O, C(R 1 ) 2 , NR 1 , where, in the case of a single bond, the carbon atoms of the A and A′ rings are joined directly to one another by a single bond, C(R 1 ) 2 , NR 1 , O and S; 
         m is either 0 or 1; 
         n is either 0 or 1,
 where m=n; 
 
         p is either 0 or 1; 
         q is either 0 or 1, where p+q is either 1 or 2; 
         R 1  is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, which is optionally substituted by one or more R 2  radicals; where one or more nonadjacent CH 2  groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2  and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms which is optionally substituted by one or more R 2  radicals; or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms which is optionally substituted by one or more R 2  radicals; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms which is optionally substituted by one or more R 2  radicals, or a combination of two or more of these groups or a crosslinkable Q group; 
         R 2  is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, which is optionally substituted by one or more R 3  radicals, where one or more nonadjacent CH 2  groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3  and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 ; or an aromatic ring system which has 6 to 60 aromatic ring atoms which is optionally substituted by one or more R 3  radicals; or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms which is optionally substituted by one or more R 3  radicals; or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms which is optionally substituted by one or more R 3  radicals; or a combination of two or more of these groups; at the same time, two or more adjacent R 2  radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system; 
         R 3  is the same or different at each instance and is H, D, F or an aliphatic, or aromatic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; at the same time, two or more R 3  substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system; 
         with the proviso that not more than one R 1  substituent in the A ring and not more than one R 1  substituent in the A′ ring contains an aromatic or heteroaromatic group having 5 to 30 ring atoms. 
       
     
     
         23 . The compound as claimed in  claim 22 , wherein the compound is of the general formula (2) 
       
         
           
           
               
               
           
         
         where the symbols additionally used are as follows: 
         X is the same or different at each instance and is N or CR 1 ; 
         Q is the same or different at each instance and is X═X, S, O or NR 1 . 
       
     
     
         24 . The compound as claimed in  claim 22 , wherein the compound is of one of the following general formulae (3) or (4): 
       
         
           
           
               
               
           
         
       
     
     
         25 . The compound as claimed in  claim 24 , wherein the compound is of the general formula (4). 
     
     
         26 . The compound as claimed in  claim 24 , wherein the compound is of the general formula (4) where X is CR 1  and m is 1. 
       
         
           
           
               
               
           
         
       
     
     
         27 . The compound as claimed in  claim 24 , wherein the compound is of the general formula (4) where X is CR 1 , m is 1, p is 0 and q is 1. 
     
     
         28 . The compound as claimed in  claim 22 , wherein the compound is of the general formula (13) 
       
         
           
           
               
               
           
         
         where V is O and where the aromatic rings each have not more than one R 1  substituent, s is 0 or 1 and t is 0 or 1, where s+t is 0, 1 or 2. 
       
     
     
         29 . The compound as claimed in  claim 22 , wherein the compound is of the general formula (15) 
       
         
           
           
               
               
           
         
         wherein s is 0 or 1 and t is 0 or 1, where s+t is 0, 1 or 2. 
       
     
     
         30 . The compound as claimed in  claim 22 , wherein the compound is of the general formula (16) 
       
         
           
           
               
               
           
         
         wherein s is 0 or 1 and t is 0 or 1, where s+t is 0, 1 or 2. 
       
     
     
         31 . The compound as claimed in  claim 22 , wherein the compound is of the general formula (16a). 
       
         
           
           
               
               
           
         
       
     
     
         32 . A composition comprising at least one additional compound as claimed in  claim 22  and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials. 
     
     
         33 . The composition as claimed in  claim 32 , wherein the additional compound is a host or matrix material. 
     
     
         34 . The composition as claimed in  claim 32 , wherein the additional compound has a band gap of 2.5 eV or more. 
     
     
         35 . A formulation comprising at least one compound as claimed in  claim 22  and at least one solvent. 
     
     
         36 . An electronic device comprising at least one compound as claimed in  claim 22 . 
     
     
         37 . An electronic device comprising at least one compound as claimed in  claim 22  in an emission layer (EML), electron transport layer (ETL) or in a hole blocker layer (HBL). 
     
     
         38 . The electronic device as claimed in  claim 36 , wherein the device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device (OLED), an organic light-emitting electrochemical cell (OLEC, LEEC, LEC), an organic solar cell (OSC), an organic optical detector, or an organic photoreceptor. 
     
     
         39 . The electronic device as claimed in  claim 37 , wherein the device is an organic electroluminescent device which is selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs). 
     
     
         40 . A process for producing an electronic device as claimed in  claim 36 , which comprises applying at least one organic layer by gas phase deposition or from solution. 
     
     
         41 . The electronic device as claimed in  claim 40  for use in medicine for phototherapy. 
     
     
         42 . The compound as claimed in  claim 22 , wherein the compound is of the general formulae (3): 
       
         
           
           
               
               
           
         
       
     
     
         43 . The compound as claimed in  claim 22 , wherein the compound is of one of the following general formulae (5) to (11): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         44 . The compound as claimed in  claim 22 , wherein each R 1  is independently selected from the group consisting of H and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more R 2  radicals. 
     
     
         45 . The compound as claimed in  claim 22 , wherein G 1  is an organic electron-transporting group (ETG) of the formula E-10. 
     
     
         46 . The compound as claimed in  claim 22 , wherein G 1  is selected from the group consisting of quinolines, isoquinolines, and quinoxalines, which are optionally substituted by one or more R 1 . 
     
     
         47 . The compound as claimed in  claim 22 , wherein G 1  is a quinoxaline, which is optionally substituted by one or more R 1 . 
     
     
         48 . The compound as claimed in  claim 43 , wherein the compound is of general formula (8).