Organic molecules for optoelectronic devices

Abstract

The invention relates to an organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule is represented by a plurality of units, wherein each unit includes or consists of a structure represented by Formula Iwhereinn=0 or 1; andX is at each occurrence independently selected from the group consisting of a direct bond, CR3R4, C═CR3R4, C═O, C═NR3, NR3, O, SiR3R4, S, S(O) and S(O)2.

1 - 15 . (canceled) 
     
     
         16 . An organic molecule, comprising a structure represented by Formula I: 
       
         
           
           
               
               
           
         
       
       and
 wherein 
 n=0 or 1; 
 X is at each occurrence independently selected from the group consisting of a direct bond, CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 ; 
 R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV  and R V  are each independently selected from the group consisting of: 
 hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I; 
 C 1 -C 40 -alkyl, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 1 -C 40 -alkoxy, which is optionally substituted with one or more substituents R 5  and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 1 -C 40 -thioalkoxy, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 2 -C 40 -alkenyl, 
 which is optionally substituted with one or more substituents R 5  and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 2 -C 40 -alkynyl, 
 which is optionally substituted with one or more substituents R 5  and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 6 -C 60 -aryl, 
 which is optionally substituted with one or more substituents R 5 ; and 
 C 2 -C 57 -heteroaryl, 
 which is optionally substituted with one or more substituents R 5 ; 
 R d  and R e  are independently selected from the group consisting of: 
 hydrogen, deuterium, CF 3 , CN, F, Br, I; 
 which is optionally substituted with one or more substituents R a  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 6 -C 60 -aryl, 
 which is optionally substituted with one or more substituents R a ; and 
 C 2 -C 57 -heteroaryl, 
 which is optionally substituted with one or more substituents R a ; 
 R a  is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I; 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 1 -C 40 -alkoxy, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 1 -C 40 -thioalkoxy, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 2 -C 40 -alkenyl, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 2 -C 40 -alkynyl, 
 which is optionally substituted with one or more substituents R 5  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ; 
 C 6 -C 60 -aryl, 
 which is optionally substituted with one or more substituents R 5 ; and 
 C 2 -C 57 -heteroaryl, 
 which is optionally substituted with one or more substituents R 5 ; 
 R 5  is at each occurrence independently from one another selected from the group consisting of: 
 hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , B(R 6 ) 2 , OSO 2 R 6 , CF 3 , CN, F, Br, I; 
 C 1 -C 40 -alkyl, 
 which is optionally substituted with one or more substituents R 6  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; 
 C 1 -C 40 -alkoxy, 
 which is optionally substituted with one or more substituents R 6  and wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; 
 C 1 -C 40 -thioalkoxy, 
 which is optionally substituted with one or more substituents R 6  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; 
 C 2 -C 40 -alkenyl, 
 which is optionally substituted with one or more substituents R 6  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; 
 C 2 -C 40 -alkynyl, 
 which is optionally substituted with one or more substituents R 6  and 
 wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, C═NR 6 , P(═O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 ; 
 C 6 -C 60 -aryl, 
 which is optionally substituted with one or more substituents R 6 ; and 
 C 2 -C 57 -heteroaryl, 
 which is optionally substituted with one or more substituents R 6 ; 
 R 6  is at each occurrence independently from one another selected from the group consisting of: 
 hydrogen, deuterium, OPh, CF 3 , CN, F; 
 C 1 -C 5 -alkyl, 
 wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; 
 C 1 -C 5 -alkoxy, 
 wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; 
 C 1 -C 5 -thioalkoxy, 
 wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; 
 C 2 -C 5 -alkenyl, 
 wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; 
 C 2 -C 5 -alkynyl, 
 wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF 3 , or F; 
 C 6 -C 18 -aryl, 
 which is optionally substituted with one or more C 1 -C 5 -alkyl substituents; 
 C 2 -C 1 7 -heteroaryl, 
 which is optionally substituted with one or more C 1 -C 5 -alkyl substituents; 
 N(C 6 -C 18 -aryl) 2 ; 
 N(C 2 -C 17 -heteroaryl) 2 ; and 
 N(C 2 -C 17 -heteroaryl)(C 6 -C 18 -aryl); 
 wherein optionally, one or more of the substituents R a , R d , R e , and R 5 , each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R a , R d , R e , and R 5 ; and 
 wherein optionally, one or more of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV , and R V , each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV , and R V . 
 
     
     
         17 . The organic molecule according to  claim 16 , wherein R 1 , R 2 , R 3 , R 4 , R I , R II , R III , R IV , and R V  are each independently from one another selected from the group consisting of:
 hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, halogen;   C 1 -C 18 -alkyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 1 -C 18 -alkoxy,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 1 -C 18 -thioalkoxy,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 2 -C 18 -alkenyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 2 -C 18 -alkynyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 6 -C 18 -aryl,   which is optionally substituted with one or more substituents R 5 ; and C 2 -C 17 -heteroaryl,   which is optionally substituted with one or more substituents R 5      wherein optionally, one or more of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV , and R V , each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV , and R V .   
     
     
         18 . The organic molecule according to  claim 16 , comprising a structure of Formula III: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula III, R 1 , R 2 , R a , R I , R II , R III , R IV , R V , and X are the same as respectively defined in connection with Formula I. 
 
     
     
         19 . The organic molecule according to  claim 16 , wherein X is selected from the group consisting of: a direct bond, NR 3  and O. 
     
     
         20 . The organic molecule according to  claim 16 , comprising a structure of Formula III-2: 
       
         
           
           
               
               
           
         
       
       and
 wherein R 3  is a C 6 -C 18 -aryl, which is optionally substituted with one or more substituents R 5 , and 
 wherein R 1 , R 2 , R a , R I , R II , R III , R IV , and R V  are the same as respectively defined in connection with Formula I. 
 
     
     
         21 . The organic molecule according to  claim 16 , wherein R V  is selected from the group consisting of:
 N(R 5 ) 2 ;   OR 5 ;   C 1 -C 18 -alkyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 6 -C 18 -aryl,   which is optionally substituted with one or more substituents R 5 ; and   C 2 -C 17 -heteroaryl,   wherein the substituent R V  optionally forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 2  and R IV , which is optionally substituted with one or more C 1 -C 5 -alkyl substituents, deuterium, halogen, CN or CF 3 .   
     
     
         22 . The organic molecule according to  claim 16 , wherein, when X is NR 3  and R d  and R e  are connected to each other to form an aromatic ring system, R V  is N(R 5 ) 2  and/or forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 2 , R 3 , R 5 , and R IV . 
     
     
         23 . The organic molecule according to  claim 16 , wherein R a  is independently selected from the group consisting of:
 hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , B(R 5 ) 2 , OSO 2 R 5 , CF 3 , CN, halogen;   C 1 -C 18 -alkyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 1 -C 18 -alkoxy,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 1 -C 18 -thioalkoxy,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 2 -C 18 -alkenyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   C 2 -C 18 -alkynyl,   which is optionally substituted with one or more substituents R 5  and   wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;   which is optionally substituted with one or more substituents R 5 ; and   C 2 -C 17 -heteroaryl,   which is optionally substituted with one or more substituents R 5 .   
     
     
         24 . The organic molecule according to  claim 16 , wherein at least one substituent selected from the group consisting of R 1 , R 2 , R I , R II , R III , R IV , and R V  forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R 1 , R 2 , R 3 , R 4 , R 5 , R I , R II , R III , R IV , and R V . 
     
     
         25 . An optoelectronic device comprising the organic molecule according to  claim 16  as a luminescent emitter. 
     
     
         26 . The optoelectronic device according to  claim 25 , wherein the optoelectronic device is selected from the group consisting of:
 organic light-emitting diodes (OLEDs),   light-emitting electrochemical cells,   OLED-sensors,   organic diodes,   organic solar cells,   organic transistors,   organic field-effect transistors,   organic lasers, and   down-conversion elements.   
     
     
         27 . A composition, comprising:
 (a) the organic molecule according to  claim 16 , as an emitter and/or a host, and   (b) an emitter and/or a host material, which differs from the organic molecule, and   (c) optionally, a dye and/or a solvent.   
     
     
         28 . An optoelectronic device, comprising the organic molecule according to  claim 16 ,
 wherein the device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.   
     
     
         29 . The optoelectronic device according to  claim 28 , comprising:
 a substrate,   an anode, and   a cathode, wherein the anode or the cathode is disposed on the substrate, and   a light-emitting layer between the anode and the cathode, and comprising the organic molecule.   
     
     
         30 . A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to  claim 16  by a vacuum evaporation method or from a solution. 
     
     
         31 . An optoelectronic device, comprising the composition according to  claim 27 ,
 wherein the device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.   
     
     
         32 . The optoelectronic device according to  claim 31 , comprising:
 a substrate,   an anode, and   a cathode, wherein the anode or the cathode is disposed on the substrate, and   a light-emitting layer between the anode and the cathode, and comprising the composition.   
     
     
         33 . A method for producing an optoelectronic device, the method comprising depositing the composition according to  claim 27  by a vacuum evaporation method or from a solution.